My Winning Streak

MY WINNING STREAK

By Katharine Sexkitten

"Kid," he said, "if it wasn't for bad luck, you'd have no luck at all."

And he was right.

Not about the 'kid' part, since I was thirty-two at the time, but he was my boss, and older, and he'd always called me that. And he was indeed old, not so much in age, just in the wearisome worn-down way some people can get to. But he was right about luck. That part of the observation was spot on.

My whole life, I could never catch a break.

In middle school, my classmates gave me the nickname 'sad-sack', which was entirely deserved. From day one, it seemed like my entire existence was destined to be one of losing.

I was the kid that always got rained on.

I was the kid that always lost at games. Card games, board games, video games, action games, it didn't matter. I'd have fun playing, but I always lost.

I was the kid who tried hard and never accomplished much.

If a dozen people were gathered together, I'd be the one that the bird flying over shat on. Guaranteed.

If I was going for a bike ride with other kids, I'd be the one who'd get the flat tire.

I was the kid whose pen exploded in his pocket, totally ruining his shirt. I was the kid who was never picked for sports because I wasn't athletic enough to even catch a ball without it hitting me and bouncing off, leaving a bruise or three.

As we got older, I was the teenager who had horrible acne, and the one and only girl in high school I asked out to the movies took one look at my face and ran in the other direction, giving me my answer. I was the only one in my age group whose growth spurt was more like a trickle, and a short one at that.

I was the one who couldn't get a date if my life depended on it.

My life had been a never-ending series of unfortunate events. I'd been in car accidents, minor things that happen to everybody, but I'd be the only one even in a car full of people to get broken bones or whiplash. I watched my peers going through life with the normal joys, making friends, having sex, partying, getting degrees in higher education resulting in good jobs, meeting their presumptive life-mates, getting married, having kids, making the big bucks, knowing none of those things were ever going to happen to me.

I shuffled along by myself, from one boring and low-paying job to another, and while everyone I knew growing up became successful adults, I just stagnated.

Not much money, a crappy apartment I could barely afford, no romance and no prospects.

I was the only guy I knew who got audited for tax evasion, even though I barely made enough money to pay taxes in the first place, and even though I didn't do anything wrongly as far as I could tell, the monetary fine they gave me for some bizarre infraction that nobody without an MBA would ever understand was almost crippling.

Sad-sack. That was me.

But every day, I put a smile on my face.

Every day.

Because even though the world always gave me a punch in the mouth, I still felt happy to be alive.

Hope springs eternal, as my Nana used to say, and I had that hope thing in spades.

One day, I kept promising myself, good things will happen.

One day.

But I never thought that it would be one day soon.

Despite my total lack of luck, every year I would buy at least one ticket on the huge lottery that the local Children's Hospital put on. There were thousands of prizes, from the big-time expensive show homes to new cars to boats and jet skis all the way down to the cheaper stuff, like sunglasses or gift cards from retailers.

And every year, I would scan the printed results in the paper, comparing the hundreds of numbers drawn to mine, hopeful at first, but always losing.

Some years when I had a few extra bucks I'd splurge.

Each ticket was a hundred dollars, but they also had options to buy three tickets for only two hundred and fifty bucks, and the money was going to a really great cause, so even though I never won anything, every year I was always happy to contribute. I kept telling myself that I was a good citizen, and, besides, one day my luck might change.

Last year, I poured over the numbers expecting nothing and to my utter shock I saw one of mine!

I'd never been more excited!

Finally! Things were starting to turn around! My luck had changed!

I took a day off work, for which I would not get paid, and when I got to the hotel ballroom along with a thousand other people, I waited in line to cash in, not knowing what I'd won but thrilled to be there anyway, waiting in line for hours only to be told that there'd been a printing error by the newspaper and the ticket I owned that I thought was a winner turned out to be a mistake.

I was a loser.

Sad-sack.

I walked out empty-handed, and poorer.

Still, I kept up a positive attitude, and smiled.

What else could I do?

I told my boss all about it the next day, and that's when he said what he said.

If it wasn't for bad luck, I'd have no luck at all.

The next year, alone as always with nothing on the horizon in either my social life or my working life, I had actually more or less decided to not buy a ticket. I mean, I liked the idea of helping out the kids and the hospital, but things were tight for me, financially, and I had some serious worries about paying my rent. But at the last minute, I looked at what was in my bank account and thought, well, what the hell, it's for a good cause.

I bought the three-ticket package.

Having been shafted once before, a couple of weeks later I read the winning numbers in the paper with a huge amount of skepticism. I wasn't going to get my hopes up too high.

The really big ticket winners were people who got phoned personally, and I wasn't one of them. All the rest of the prizes, you had to find out what you got when you showed up to collect.

Sitting in my ratty house coat, in my crappy apartment, with a cup of coffee, I scanned the numbers.

Halfway down the list, my heart started racing.

THERE'S ONE OF MY NUMBERS!

HOLY HELL!

A little further down the list, and I practically shouted at the top of my lungs.

DOUBLE HOLY HELL!!

Two numbers!

Practically dancing with joy, since I presumed they couldn't make more than one printing error, odds were, I kept thinking, at least one of them must be right!

I scanned the rest of the list quickly, because there was no way I'd ever be lucky enough to have all three numbers, but to my utter shock and amazement right towards the end, there it was!!!

MY THIRD NUMBER!

ALL THREE OF MY TICKETS WERE WINNERS!!!

I kept pinching myself, literally, thinking there must be something wrong, that I was dreaming or hallucinating, but repeated checks and re-checks kept giving me the same results.

I looked out the window, to see if pigs were flying.

Three winning tickets!

TRIPLE HOLY HELL.

On the appointed day, I showed up super early to the hotel, hoping to get in and out quickly, so I could go back to work at least for some of the day and maybe make a little bit of money, only to discover that the other thousand or so people had done the same thing.

I waited and waited in line.

Finally, after two hours, I got to a table.

A bored middle-aged woman with dyed hair and a really big nose took my first ticket from me and punched in the number to her computer, and moments later I heard a 'ding' and she looked at what the result was and then walked away to the other end of the ballroom, coming back with a thin and long metallic case before handing it to me and saying in a bland non-committal voice, "congratulations".

I'd won a set of shiny new barbeque tools.

Sadly, I didn't have a barbeque.

We weren't allowed such things where I lived. It was a decrepit old wooden building and barbeques were too much of a fire risk.

She looked at me like I should go away and then past to the person in line behind me and said, "NEXT!"

I waved at her.

"I have another winning ticket," I meekly pointed out, and she acted surprised, because how many people get more than one winner, right? But, she plugged the numbers in and we both heard the 'ding' and she looked surprised and then walked away and came back with an envelope.

"It's a gift card," she said, handing it to me and giving me the same look as before, leaning her head to her right, as if she was looking at the person behind me.

"NEXT!"

I leaned my head to my left, mirroring her.

"I've got one more winner, actually."

Her face changed in an instant to outrageous disbelief, and serious incredulity, like, c'mon, seriously? You have three winning tickets?

But we both heard the 'ding' after she keyed in the numbers.

Off she went, coming back with a bigger envelope than before.

"Three winning tickets! That's practically unheard of. So this really is your lucky day," she said, loudly, so other people could hear, "congratulations," and then she said, with what sounded like genuine glee, "you've won a cruise!"

I stood there, my mouth open, in absolute shock and amazement at my fortune.

THREE WINNING TICKETS!

A set of barbeque tools I'd have to give to someone else, and a gift card for something, and a cruise!

I'd never been on a cruise.

I'd never been anywhere.

Sitting on the bus, I held my backpack with the envelopes in it and my thin metallic case in my lap like they were the Holy Grail and there was no way I'd let someone steal them, which is the kind of thing that can happen to unlucky guys like me. I decided almost instantly that if it came right down to it, I could easily give up the barbeque tools and hope I didn't have to give up my backpack as well.

I was itching to open the envelopes, though, dying to read the details, and it made me antsy, percolating with energy, little tics and tremors appearing willy-nilly everywhere, all up and down my body, making me jumpy, and at one point I was almost shocked to realize that I had a throbbing erection.

I was as hard as a rock, and getting those little signals all up and down my body that an orgasm was close-by. Maybe not imminent, but right around the corner, and it wouldn't take much to climb to the top of that ladder, which would be a disaster, sitting on public transit.

Getting off the bus, I had to awkwardly hold the backpack in front of my crotch so people wouldn't see how erect I was.

Safely at home, I dumped the barbeque tools on the floor and ripped open the first envelope.

My eyes went straight to the numbers.

A thousand dollars!

The store name, though, meant nothing to me, so I googled it.

Rose Wind.

Then I saw their page come up.

According to their website, they offered 'the finest women's apparel', including everything from dresses and gowns to 'intimates', meaning lingerie.

Close to ninety percent of the mind-boggling joy I was feeling evaporated, instantly.

What the hell was I going to do with a thousand bucks worth of women's clothes?

A little dejected, I threw it on the pile of bricks I used as a coffee table and then ripped the bigger envelope open, and most of my elation returned, instantly.

Overdosing on glee I read all the printed material. A four-night cruise, starting in San Francisco and ending up in Los Angeles, after stops on Catalina Island and then San Diego and a town in Mexico that I'd never heard of, on the cruise line known to be 'the party ships', the airfare to get there and all the transportation connections arranged, an inside stateroom without a window, exotic ports-of-call, at least to me, and a huge booklet describing all the different excursions available at each stop, many of which made my heart race, all of them exciting adventures that had me floating on air.

That is, until I read the fine print on the prize and found out that none of those things were paid for.

Nothing was paid for, except for getting me there and back and the room and food for seven days.

Everything else was on me to pay for, and my heart sunk when I realized I probably couldn't afford much of anything, even with a few months to save money. Little or no booze, no fancy day-time trips, no on-board spa treatments or massages, nothing.

But still, I won a cruise!

The next day I gave my boss the barbeque tools, and he nodded his thanks, giving me the look like I should accept his minor gratitude and leave his office, and go back to work, which is when I explained that I'd also won a cruise.

I skipped right over winning a thousand dollars of women's clothes.

He looked at me like I'd asked him to eat his own flesh.

"YOU?" he snorted, "SERIOUSLY? You won a cruise?"

After showing him the paperwork, he still had a hard time believing it, having known me and my bad luck for a few years. I asked him which weeks were still open for employee vacations, since I didn't have much seniority and had to let other people pick before me, and he looked at a file on his computer and said, "one week in March and one in August."

Later that day, after work, I spent a long time on the phone and booked my cruise, for March, a scant two-and-a-half months away. The nice lady on the phone kept trying to upsell me on everything, from the seats on the planes to the room on the ship, but she more or less figured out after a while that I wasn't biting on any of the other options she had to offer, because I couldn't afford them, and once we got to that point of understanding the rest was easy.

"Enjoy your trip," she said, with some real glee in her voice, after we'd confirmed everything.

For a couple of days I was floating on air, but there was one thing pulling me down, like a little bit of weight on me. The thought of travelling to these exotic places without any spending money kept nagging at me, but I realistically had no way of making my financial situation better.

I didn't even own anything of value I could sell.

But then I had an idea.

The next day, a Saturday, I took two buses to get to the store. Rose Wind was a fancy shop in the fancy part of town, so I'd never been in it or even near it, and from the outside it looked huge and cold.

But walking in, I felt totally different within seconds.

The soft music playing was delightful without being distracting, and put me at ease almost immediately. A serene kind of feeling fell over me, inspired by the beautiful and warm colors of the interior of the store, which were truly calming, creating an atmosphere of instant and genuine welcome.

Just as instantly, I was completely and immediately overwhelmed emotionally by the raging softness and femininity of everything in sight. As if exploding all around me, from every direction, the colors and fabrics bombarded me, capturing me and smothering me with display after display of clothes that just screamed out the word 'WOMAN!'. Racks, tables, and cabinets were filled to overflowing with garments that defined 'feminine', and as a life-long adorer of everything having to do with 'feminine', I felt like a kid in a candy store, except the goodies on display weren't actually meant for me.

There were mannequins carefully placed throughout the store draped with the textbook definitions of alluring and sensual, dresses designed to make the women who wore them as beautiful as they could be, regardless of their size and shape, and for not the first time in my life I was struck by the power of beauty, the power that women had, whether they used it or not, the power to literally manipulate their world and the people around them merely by how they deport themselves and what they wear.

A woman in her forties, by my guess, maybe late forties, with perfectly-coiffed hair and carrying a bit more weight on her than she'd probably like approached me, with a smile as wide as a river.

"Good morning," she said, her voice soft and a little husky, "and welcome to Rose Wind. My name is Leslie. Is there something in particular I can show you, or would you prefer to just browse on your own?"

The nametag over her left breast announced she was the store manager.

I stood in awe of her, and the power of feminine beauty that she displayed.

Wearing a deep wine-colored blazer over a silky-smooth almost see-through white blouse, the lines of her bra showing intermittently on the material as she breathed in and out, and a dark form-fitting skirt, stopping teasingly at her mid-thighs, and tight around her generous hips and rear end, she wore dark gauzy hose on her legs, supported on three or four inch wine-colored heels.

She was iconic.

She was a walking talking example of everything I'd always adored and been attracted to, the feminine qualities of deportment and style and allure that, to my mind, were the pillars of everything beautiful in the world. As someone who'd spent his whole life, thirty-three years, admiring women and their innate graces, tenderness, sensitivity, sensuality, gentleness, sexuality, and delicate loveliness, all the things I wished I got to enjoy every second of every day but hardly ever did, Leslie epitomized there and then an ideal, the best ideal anyone could possibly imagine.

I was star-struck.

Taking a few moments longer than I should, I finally came out of my little fog and introduced myself, explaining to her that I'd won a gift card, in the lottery, pulling it out of my pocket to prove it, and her smile of genuine happiness for me lit up the room.

"Congratulations!" she almost-giggled.

So I said thank you, and then, a little sheepishly, explained that I had no use for the card, for obvious reasons, and I had no one to give the card to, or the clothes, and that I was hoping that I could just get the cash equivalent.

Leslie tilted her head slightly, with a look of care washing over her face, and she asked, quietly, "there's no one special in your life?"

Once again, I had to sheepishly shake my head.

We stood in an awkward silence for a few seconds, and I could have sworn she was coming to a decision that showed she understood my request.

But I should have known better. I didn't have such luck.

"I'm so sorry," she said, "I know that it's not the answer you were hoping for, but the gift card is for merchandise only, for product only, and not for the actual money. That's the store's policy. I hope you can understand our position?"

And just like most everything that had happened for my whole life, my hopes for something good were dashed, and the first thing that went through my mind was, 'oh well, business as usual'.

The barbeque tools were useless to me and now the card was as well, so two out of three of my tickets were write-offs, which made me sad, and I sighed.

"Okay," I said, dejectedly, "well, then," and I struggled to find something to say, "well then, thank you for your time."

I turned to leave.

"Wait," Leslie said, and when I turned back to look at her, she tilted her head again, in that matronly caring way.

"Are you sure there's not something here that you might enjoy?"

The word 'ludicrous' rose up in my head, but before I could voice it, she'd stepped towards me and gently laid her fingers on my arm, touching me softly, the bright red of her polish shining from the subdued overhead lighting.

"Can I tell you a little secret?" she asked, and before I could answer she said, "there are men, more than a few men actually, maybe more than you'd imagine, who enjoy some of the clothes we have here. And some of them become regular customers."

I looked at her with confusion.

"There are?"

She nodded.

"Yes, there are," and then she smiled at me, "there are men who appreciate the feel of the clothes, the fabrics used in women's clothes, our clothes so much softer and silkier than yours. Some men love the way they touch your skin, the way they caress your skin. For many men, it has absolutely nothing to do with, um, well, how do I say it politely? It has nothing to do with the delicate subject of sexuality. It's all about the sensuality."

She said that word slowly.

S-e-n-s-u-a-l-i-t-y.

She almost purred it.

My head spun as if it was on a pole, and I took an inventory of the raging femininity spread out around me, awash in surprise and shocks to my sensibilities, at the idea of men wearing any of what I saw.

The two bus rides home were weird, owing to the gigantic juxtaposition consuming my thoughts.

Battling hard, the absurdity of buying women's clothes and all the negative reactions inferred from that was strong, and yet I couldn't deny that equally strong was the pulsing tender erection in my pants, a throbbing excitement that had me on the edge of orgasm, seconds away from release, one or two rubs away from an explosion I just somehow knew would be cataclysmic.

Especially on public transit.

My hopes of receiving money gone, I fell back down from my emotional highs and landed hard on the ground. But at least I had something to pick me back up again!

I was going on a cruise!

Every day that followed I was on pins and needles, all the time, churning with anticipation at my vacation. At work, at home, running errands, all I could do was daydream, and imagine different upcoming scenarios.

Lying around the pool, drinking something cold and sweet.

Dinner at huge tables with charming companions.

The disco, the lounges, the live entertainment in rooms full of buzzing partying people.

Poking my head into little shops in every port, even if I couldn't afford to buy anything.

Surprisingly, as time went along, a new wrinkle in those scenarios emerged, one I wasn't prepared for and therefore felt completely shaken by.

The theme was simple.

All the events and activities I was imagining that might happen on my sea-bound adventure were all suddenly colored with women's clothing.

Strangest of all, I was soon enough day-dreaming me being the person wearing them.

Me, wearing short shorts and tiny tank tops, bra and panties underneath.

Me, wearing the skimpiest bikini, or thong, around the pool, or treating myself in a hot tub.

Me, wearing dresses, or skirts and blouses, the finest lingerie underneath, always with heels, exquisite and thought-provoking.

Me, with makeup on, and jewelry, my hair soft and styled.

Me, someone who'd always adored everything to do with women and how they dressed, how they presented themselves, now suddenly emulating them, joining them in their delicious environ, paying homage to them, yet more importantly savoring their delight, their spirits, their demeanors, their gentility and softness, and perhaps even recognizing that there might be some femininity in me, as part of the natural duality of life.

I'd spent a lifetime, thirty-three years, in love with femininity. The allure of it, the softness of it, the daring of it, the boldness of it. Just the idea that a person can drape themselves with silky and satiny material, a delight to the skin and the senses, in every culture, that in itself made me spacey, so radically different from my experience with men's clothes and their industrial roughness and their total lack of style, boring utilitarian products only, none of it sensual or sexual, and it didn't matter if I was at home or at work, those day-dreams made me excited.

Those day-dreams made everything ripple inside me, as if I'd plugged myself in to some sort of brand-new power supply, and I was miraculously energized with a kind of propulsion I couldn't have even realized existed before.

My heart was thumping, my skin was pulsing, my spine was straighter, my body was vibrating, my hips moved of their own volition, slightly and gently rocking my groin back and forth, whether I was sitting or standing.

Almost all the time!

In no time at all I spent all of my awake moments having those day-dreams, somehow managing to get through life without killing myself or anybody else, so little attention was I paying to reality.

It shocked me one day at work to come out of my stupor and realize that that particular day-dream had been of me, in an gloriously-feminine evening gown, at a fancy formal ball, being spun around the dance floor by a tall man whose features I couldn't quite make out but made me think he was handsome, who I just knew couldn't take his eyes off me, and ended with the two of us in a bedroom, the last images burned into my soul was of kneeling down, with my eyes staring up at him, telling him non-verbally that I wanted it and was going to take what I want, while my fingers with their long painted nails pulled down his zipper, his formal pants falling to the ground, his impressive manhood bobbing in front of my mouth, long and thick and veiny, my lips quivering with anticipation, a pool of saliva resting on my tongue.

Never mind the fact I'd been wearing the ultimate in feminine clothes in the dream, and behaving like a woman would, being treated like a beautiful woman would, which was wild enough, but the entire idea of doing anything romantically or sexually with another man was a complete hair-raising out-of-left-field moment, surprising me to my core, more than stunning me with the audacity of it, and I had to stop myself afterwards and tell myself that it was just a silly dream, it wasn't real, and there was no way I'd ever do anything like that in the first place, because I wasn't gay.

Every day I'd look at that gift card, and wonder.

Could I?

Should I?

As the days and weeks passed, I found it harder and harder to find an argument for why I couldn't, or why I shouldn't.

One of the many voices in my soul yelled out often that there was no harm in just trying, and that's ultimately what made the decision for me.

If I didn't like it, no harm done, right?

Always the optimist.

Always with a smile on my face.

When I walked into Rose Wind the second time Leslie was once again there and she lit up with a huge smile, her red lips open, her teeth white, and she walked towards me, working her hips in that natural way women do when they're wearing heels, that has always defined for me one of the foundations of attraction and playfulness.

"Hello for the second time," she said, this time reaching out her right hand, so I reached mine out and we held each other, her skin warm and soft and smooth and almost delicate, such a delightful difference from touching a man, "it's lovely to see you again."

I held her hand way longer than I'd ever shaken any man's hand.

"It's, uh, really nice to see you too," I answered, realizing that I meant it more than just about anything, because she was a lovely sight to behold.

Her blazer was a dark green this time, but underneath she'd opted for a bright yellowy-orange form-hugging silky dress, stopping at the middle of her thighs. With a deep-v neckline, the valley created by her more-than-ample breasts was as sexy as any image in the world, and with generous hips and what looked like a more-than-modest rear end, her dress was tight and clingy in all the right places. And with hose in a sheer ash-grey on her legs, leading down to black pointy-tipped heels, all the tremors and thrills that were now a part of my daily life got louder and throbbed harder.

"So how can I help you today?" she asked, with just the right amount of playful curiosity in her voice to let me know she was open to any kind of discussion.

"Well," I began, and then recited the little speech I'd rehearsed mentally on the bus rides over, "I've been thinking about what you said," and then I gave her a moment to recollect our last conversation, "about how there are some men who, you know, who buy and wear some of your clothes."

For a second she just smiled at me.

"Not your clothes, personally, of course" I stammered out, "I mean the clothes in your store."

She nodded, like it was a perfectly normal and rational conversation that adults can have, and it made me realize that it was. It was okay to talk about it.

"I just thought that it would be a shame to let so much money on the card go to waste. So, I've been considering what you said, about the feel of the fabrics, and I thought that maybe, you know, maybe I should be more, I don't know, open-minded about things, and maybe give it a try."

My voice went up a little bit on the word 'try', as if it might be a question.

"Of course," she said, her smile getting warmer, "I think that's a wonderful idea. So tell me, have you thought at all about what kinds of garments you might like to try, or where to begin?"

I hadn't, and she sensed it right away.

"How about we start over here," she said, gesturing to her right, leading me to walk with her, "we have some lovely blouses that might be a good place to kick things off. They're shirts, after all, the same as what you men wear, what you've worn your entire life, but I think you'll be surprised at the lovely differences in how our shirts are made, the differences in how they're cut, the materials used, and how they'd feel on your skin."

In front of a stand with arms in four directions there were blouses on high-end wooden hangars of a variety of styles, subtle differences in collars and necklines and cuffs noticeable, and in a rainbow of colors that were decidedly soft, muted purples and periwinkle blues and scarlet reds and bone whites.

Encouraging me to try, I gently took the material of a blouse and touched it, on my palm and on my fingers and on the outside of my hand, and shivered with a racing excitement, which I realized Leslie had to have seen.

And a second later I realized that I wasn't embarrassed or ashamed at all.

SHE WAS RIGHT!

These clothes DO feel amazing on my skin.

I was happy, almost elated, at sharing my new exciting endeavor with someone, someone who I knew was sharing with me in what seemed like a real heartfelt desire to help.

"Don't they feel divine?" she asked, and we both knew the answer, "and again, they're shirts, if you want to call them that, and you could wear them in your daily life, if you dared."

Just the idea of walking around in public wearing a woman's blouse sent blood flowing to my groin, and my nipples, making them swell just a little.

I nodded, in understanding.

"Yes, absolutely," I whispered, "I think you're right, that would be an excellent place for me to start."

Price-wise they weren't too bad, so I picked three. One red, one white, and one blue.

Leslie slowly and methodically guided me through the rest of the store, pointing out things that some men like to wear, such as trousers, the difference in design a not-so-subtle change from the kinds of pants I'd ever worn, through skirts and dresses, minis and midis and maxis and flowing gowns, and I walked in awe and admiration of almost everything she showed me. Their shapes, their colors, their softness, their languorous femininity, they all mesmerized me, and once again I was rock-hard and throbbing.

"One of the big things that many men truly enjoy is our hosiery," she said, pointing to a wall display with a variety of pantyhose and stockings, as well as a modest selection of garter belts, "have you ever worn anything like these before?"

I shook my head no, feeling a tinge of regret in admitting it, as if I'd perhaps walked through life missing out on something truly blissful.

Leslie put her hands together as if she was praying.

"Well, then, you can't imagine how they feel, the silkiness tight on your skin. I've talked with more than a few men who discovered the sensuous pleasures of hosiery, and I can tell you from a lifetime of personal experience that there is nothing in this world quite like smooth silk on smooth skin."

I thought about the hair on my legs, and how they therefore weren't as smooth as hers, and mentally subtracted some of the pleasure she was hinting at, and I still came up with what promised to be a huge amount.

Leslie leaned in closer to me, and her voice got softer.

"Some people consider it a chore," she admitted, "having to do it every day, but for me there's nothing except joy in the act of shaving my legs. Sure, it's a little bit of work every morning, a few minutes in the shower, getting rid of stubble, but you'll adore the result. Sliding stockings onto smooth skin is a feeling I think every person should experience, because it's so satisfying."

She said those two words slowly.

S-o and then s-a-t-i-s-f-y-i-n-g.

She almost purred them.

I was at that stage again, hard in my pants, close to exploding, and I had to calm myself down a little bit, and after showing me various styles and weaves and designs, I added four pairs of thigh-high stockings and two sets of stockings with their necessary matching garter belt to what I was buying.

Approaching the sales counter at the back of the store, we passed several tables of panties, and the delicate sensual sexuality of them shone to me like a supernova in the sky.

They were the textbook definition of 'woman' to me.

Bikini panties, boy shorts and boxer panties, Brazilian panties, brief panties, high-waisted panties, French cut panties, hipster panties, thong panties, tanga panties, g-string panties. The selection of styles and colors was overwhelming, like the most plentiful non-threatening addictive drug in the world.

Leslie saw me eyeing them and slowed us to a halt.

"I see you've spotted our biggest seller to men," she whispered, and when I looked surprised she nodded, "without question," and ran her dark blood-red nails teasingly over a stack of them on a table, "and what men have told me is that the combination of the softness of the material and how they hold your, um, your man parts, so tenderly, as opposed to how men's underwear just smothers things, those are the reasons why so many men love wearing panties."

My second visit to Rose Wind knocked a quarter of my available funds off the card.

For two bus rides home I sat and twitched again, tics and tremors of nervous energy exploding in little booms inside of me, my hips doing the vibrating thing once more, my bum sliding ever so slightly back and forth on the molded plastic seat, the expensive white shopping bag with the words 'Rose Wind' emblazoned on it perched on my lap, covering up the small but serious lump in my pants, almost-painfully erect, and I could practically hear the blouses and the stockings and the panties talking to me, teasing me with their guarantees of delight, making me silently scream at the bus drivers to go faster, so I could get home sooner.

I had to hold the shopping bag awkwardly in front of me when I got off the buses, so people didn't see my erection.

The first pair of panties I slid on, after getting naked, was a G-string, with a gauzy lace triangular front panel that was see-through and teasingly showed my erection and my balls, which excited me, although the attached thicket of pubic hair made the sight look a little scruffy, the thin thread of the straps around my hips and up through my bum cheeks tight like ropes, exotic-feeling, and only a miraculously quick grab at my hard-on, squeezing it with all the grip I had saved me from ruining those brand new panties right off the bat, by absolutely soaking them in my cum.

Because that's what would have happened.

Rolling the stockings up my legs, slowly, feeling every pore of my skin chilling as they touched the sheer fabric, even with the hair on my legs, almost sent me over the edge again, and after I snapped them both on to my upper thighs, I looked down at myself and fell in love.

That's the only way to describe it.

I fell in love.

I was wrapped in delicious!

These clothes were not just touching me, not just laying on me, they were actually caressing me!

They were stroking me, and holding me, and massaging me, and pleasuring me!

Women's clothes were making love to me!

Walking around my apartment, the string of my panties almost felt like it was pulling me up, by the bum, so I was moving differently, pointing my toes as they swept forward, making me lead with my groin, which naturally just inspired my hips to turn and rotate in a way I'd never walked before.

Slipping into a blouse, the blue one, sapphire and shiny in the light, doing up the cuffs and then the buttons, all the way to the top, sent continuous rivers of tingles through me, from every cell of skin they touched, wispy, and covering the naked half of my body with thrill after thrill, in repeating waves, broken only by a slight tightness in my chest area, and it only took one look in the mirror to understand why.

My nipples were rock hard, and swollen.

I'd never seen them or felt them so taut, and so tender.

Suddenly inspired, I tucked my chin in and looked down and blew a blast of cool air at my left nipple, and less than a second later my entire body was shivering, lurching to and fro, and that nipple became even MORE swollen.

I spent hours wallowing in the delirious sensations of the clothes, trying on different panties and switching blouses from time to time, until I finally let myself go, masturbating harder and stronger than I'd ever done before, really working my erection, frantic and furious, panting like an athlete and watching seeps of pre-cum oozing out of my pee-hole, when it was exposed by my foreskin being pulled back.

My orgasm was the most intense, prolonged, and body-thundering event in all my thirty-three years.

It was probably more intense and prolonged than ALL the events of my life put together.

For the next week, I wore panties and stockings under my office clothes every second of the day, and at every moment of the day I was alert and bouncing, those tics and tremors created by the lingerie making me more productive and turning a boring bureaucratic life into one of mild enjoyment.

Every night I was at home, wearing lingerie and blouses, leading to hours of titillating delight and then thunderous exhausting masturbation sessions.

All of which doubled or tripled in intensity after one day I spent almost two hours with a razor, making every square inch of me below my head as smooth as glass, as I discovered that Leslie had been right again, perhaps even had been underwhelming in her words, when she described the absolute joy of smooth silk on smooth skin.

That first time I slipped panties and stockings and a blouse on my skin, hairless and tender, I came so hard I had to lay down and rest, and right then and there I promised myself I'd never be hairy again, no matter how much time it took me every day in the shower to shave all over.

I even shaved my man parts, which takes a steady hand and nerves of steel, because nicking one's own testicles is unbelievably painful. But the end result was as beautiful as beauty can be.

The next Saturday, I was at the door of Rose Wind before they opened up for business.

Leslie gave me a hug, and a knowing smile, like she'd predicted to herself that I'd be back soon and she'd been proven totally right.

When she asked me what I was interested in looking at this time, I answered with enthusiasm, and loudly barked out one word.

"MORE!"

More of the softness. More of the silkiness.

More of the sensual pleasures I'd been going through every second of every day for a week, explaining to her with unabashed glee how I worked and slept with panties on, at the bare minimum, and how wearing them made my day go better and my nights go crazy, and how just wearing women's clothes was actually affecting not just my waking moments but were also radically influencing my dreams, my nights now full of wildly arousing action, so unlike my entire existence before.

She smiled like she knew exactly what I was saying, as if she'd lived it herself, or had other men besides me explain it to her.

"You're discovering what it's like to treat yourself with softness, and how that touches every aspect of living."

In no rush, Leslie lazily took me through the store again, showing me some new arrivals to add to the clothes I'd already seen, explaining matter-of-factly how certain items went well with other things, color-wise and style-wise, and while for the most part she kept to things that a man could wear under his normal clothes, which she knew was my situation, she never stopped encouraging me to at least consider some of the other things women wear that I could try, even if I had no realistic chance of ever wearing them outside of the safety of my apartment.

The dresses and skirts, for instance.

Obviously I couldn't wear those outside, she agreed, but she once again rationalized that I might consider buying some because the way they would make me feel, even trapped in my own apartment, was, in her words, "a game-changer".

"Trust me," she said, "I've had lots of men over the years tell me how much more sensually alive they feel wearing a dress, how much more peaceful and aroused they can get, how all their senses get to go wild," pointing at various clothes, "and again, these are men who, for the most part, are normal men. Um, I mean straight men, of course. Heterosexual men. Because" she added, quietly, "it's not a 'gay' thing, it's not a 'transvestite thing', or a 'cross-dressing' thing, it's not about that at all. It's about the fabric of the clothes, the feel of the clothes on your skin, and the sensuality."

She said that word slowly.

S-e-n-s-u-a-l-i-t-y.

This time she did purr it.

Just for fun, and since it was slow in the store and there were no other customers, she offered me the chance to try a dress on.

"Any dress", she said, waving her arms around her, covering all the directions inside her store, "as long as we have one in your size."

I hemmed and hawed, but eventually she wore my resistance down, which to be honest didn't take much effort, and after using a bendable tape measure to get my 'numbers', writing down my chest and hips and height measurements, she smiled at me with real pleasure and said I was probably a size six, which meant nothing to me, until she 'tsked' a little bit and assured me that many of her female customers would give up their eye teeth to be able to fit into a size six anything.

"You're a little less than the average for men in terms of height, and weight too probably," she remarked, "but like all men, your shoulders are what's going to determine your dress size," which made no kind of sense to me at all, until she explained that men's shoulders tend to be wider and larger than women's, and the last thing anyone wanted was to have the garment be tight or restrictive at the top.

After much prodding, and me slowly gazing around the store, I picked a particular dress to try.

It was a dress that had stood out to me in all three of my visits, somehow attracting my eye even more than all the other feminine clothes, which was saying something.

As golden as straw on a summers day, and sleeveless, the dress looked as light as a feather, and my mind had already decided that it would feel that way on me, almost as if I wouldn't be wearing anything at all. The neckline was about halfway between prim and slutty, the middle of it not as wide as the top, the bottom of it flaring out in pleats that seemed to float, and would come down to just barely under my crotch.

Just looking at it, it screamed out the word, 'FEMININE!'

As I stepped into the spacious change room, Leslie asked me if I wanted to see the results by myself, with privacy, or if I would allow her to be there with me, and I was touched by her offer, once again sensing that she was doing everything she could to make this experience the most enjoyable for me, and I told her honestly that I valued her thoughts, and was relying on her opinion, so I couldn't imagine doing it without her.

The look that came on her face was as intimate and gentle as I could ever imagine, and she silently thanked me.

Naked except for my panties and stockings, I held the dress in front of me inside the dressing room, facing the mirror, shivering anew at the idea of being so daring and naughty and so unlike me, until the anticipation became a burden and I carefully gathered the dress up and slid it over my shoulders and let it drop.

Once again, I had to move like a rocket and clamp onto my erection, for fear of lurching out an orgasm and ruining a dress I didn't even own. If the panties got soaked in my cum, I could deal with that, because I'd already had that happen a couple of times, but if I ruined a dress I'd have to buy it.

Squeezing for over a full minute, the impending release subsided, and I was finally able to breathe calmly again, and take a full look at myself.

If I ignored my head, with my normal masculine haircut and face, plain and undecorated, from the neck down I saw something that made my heart race, that made it gallop.

I saw me.

I saw a feminine me.

I saw me wearing clothes that I wasn't born to wear, clothes that most people in the world would scoff at me for donning, and yet clothes that made my insides sing with a seriously huge delight and pleasure.

"How are we doing?" Leslie asked, from outside the door, and for a moment the idea of walking out and showing this lovely woman the radically new me, in lingerie and a dress, it seemed ridiculous, and in one horrible second some part of my brain decided I'd gone too far, and should stop this nonsense right away.

But that suggestion got vetoed by all the other parts of my brain. They kicked the shit out of it.

Stepping out, I watched Leslie's reaction, which was a genuine and real support, honestly, nothing but acceptance on her face, and she looked me up and down, turning her head from side to side and getting me to spin slowly, on the balls of my stockinged feet.

Finally, she stood behind me and turned me with her hands on my shoulders to a full-length mirror, showing us both a full-frontal look at me, with her head over my right shoulder.

"How does it feel?" she asked, a knowing smile on her face.

The words came easily.

"It feels like heaven," I answered, unable to initially process all the different words for the wonderful feelings I was going through. "It's just so soft, and so airy," I said, "so luxurious, so, oh my god, so tight and yet so light!"

Leslie nodded enthusiastically.

"Walk around," she suggested, "it gets better."

Padding in small circles, I instantly understood what she was getting at. The air in the room roiling and sliding up under the dress and caressing my thighs and my groin, most of it just skin, since my thong panties didn't cover much, was like being on a mountaintop, coolness and deliciousness touching everything!

I saw an idea form in her mind, and she sashayed away, her heels once again making her work her hips, creating that mesmerizing walk that women have that is one of the cornerstones of allure and beauty, shortly returning with something in her hand.

I must have had a questioning look on my face.

She grinned, almost sheepishly.

"For some men," she explained, "and again, it's not a sexual thing, but for some men the experience isn't complete without wearing a bra."

She saw my reaction, which was a mixture of skepticism and surprise and questioning.

"There's no point in trying a dress on if you're not wearing the appropriate undergarments, something that creates curves, even when there isn't a lot," she reasoned, "the dress just wouldn't hang correctly, it wouldn't fit you properly."

She handed me a small bundle.

"It's up to you, of course," she whispered, "I just thought that since you've come this far, why not go all the way? After all, there's no harm in trying, right?"

I couldn't help but nod.

I looked at the bra she'd selected for me.

It was black, and lacy everywhere, and I was struck by how small and almost insignificant in size it was and yet how utterly huge and potentially world-shattering it would be to wear it.

I didn't have breasts. I didn't need support in that way, although I will admit my pecs had developed a tiny little bit of sag in them, owing to my age and a life of sitting behind a desk. But still, the incongruity of the image in my head of me wearing a bra seemed to flare and then fade away quickly.

So maybe there was more to wearing a bra than simply support? Maybe Leslie was right? Maybe it was all about helping to accentuate shape, or emphasizing curves.

I took the bra from her hands and stepped into the dressing room, unzipping the dress and carefully taking it off again, delicately hanging it on the hangar, making sure it wasn't bunched or caught up, potentially ruining the lines of it, and then I held the bra in my hands and tried to figure out how to put it on.

I slid my arms into the holes, and put the cups up against my chest, just under my pecs, but then I tried to reach behind me with both arms and hook the back strap, feeling ridiculous that I couldn't even get the two sides close to each other, let alone connect them, no matter how much contortion I put myself through.

Finally, after several tries, I had to admit defeat.

Cracking the door open, I saw Leslie's warm smile again, and while it was slightly embarrassing admitting it, I asked her how to put the damn thing on, and she almost giggled, and then waved me out of the dressing room, into the viewing area, in just my panties and stockings, and then showed me.

It turns out you put it on the wrong way, with the cups on your back, hooking up the back straps on your front, where you can see them and hook them, and then slide the whole thing around you, one-hundred-eighty degrees, until the arms holes were available, and then slide the whole thing up and over the boobs, or in my case, 'moobs', as she called them, and then smooth out the straps, which are bound to twist at some point.

Then, like it occurred to her out of the blue, her face got a glow to it, and she asked me what my shoe size was.

"Eight," I answered, realizing where she was going with things, "I'd need a size eight shoe."

Leslie shook her head.

"We use different sizes," she explained, "so a man's eight would be about a woman's nine or ten, or maybe eleven."

While she strutted off, I went back into the dressing room and put the bra on, and as soon as I had the two hooks done up and felt the constriction of the straps, my whole body stiffened. I took a huge sharp breath in as an automatic response, nature prepping me for whatever might happen that I wasn't expecting, just in case.

After the slide, and the shift up, and the fitting around my flesh, and my arms through the holes and the straps all untwisted, I could feel my blood coursing through my veins, and my nostrils were flared, I was taking in so much air and heaving it out again in such a hurry, like a racehorse.

Never had I felt so bound.

Never had I felt so tied.

Never had I felt such constriction.

Never had I felt so secure.

Never had I felt so supported, as if the arms of the strongest human in the world were around me, keeping me out of harms reach, protecting me, like wearing armor, safely contained and wrapped in strength.

I stood, open-mouthed, and gazed at the short mirror at me, the new me, wearing panties and stockings and now a bra, and realized I was one second away from a bone-rattling orgasm, and again I had to do the full-bore squeeze.

The front of my thong panties was wet, in an obvious roundish stain, and it made me realize I'd been seeping out pre-cum the whole time I'd been preparing for wearing a dress, everything about the experience exciting me to degrees I'd never found in the normal world, in my boring past.

Leslie knocked on the door, bringing me out of my delirium, and when I barely got it open her extended hand came through the gap holding a pair of shoes.

They were stunningly simple, and stunningly beautiful.

Also a golden color, to match the dress, they had tiny little tapered heels that had to measure at least four inches high, maybe five, and a curved sole that pointed the toes almost straight downwards, and one broad simple strap across the top, to hold them on.

A part of me couldn't believe I was about to try on women's shoes.

All the rest of the parts of me couldn't wait to do it.

I slid the dress back on, with my back to the mirror. On a whim, I decided I wanted to see the full effect in the larger mirror in the viewing room, instead of just some of me in the smaller dressing room mirror, so I slipped on the shoes, teetering and wobbling at first, worrying about how I'd manage to walk in them without breaking an ankle, until with a few tentative steps in the dressing room I couldn't wait to show myself how it all turned out and I slowly stepped out.

I realized I also wanted Leslie to see the full effect too.

Her smile was gigantic, and she clasped her hands together in front of her chest, just above her breasts.

The gap in her blazer let me see that her nipples were about twice the size of mine.

"You look lovely," she said, quietly, and with reverence.

I felt lovely.

For the first time in my life, I felt lovely.

For the first time in my life, I felt like I actually understood what the word 'lovely' meant, and how everything in my past that I'd considered 'lovely' at the time completely paled in comparison. They didn't even rate.

In the mirror, I saw reflecting back at me so many of the aesthetic and emotional qualities of the femininity that I'd always adored, sending every cell of my body soaring with glee. I stood with my hands behind my back, the shoes making me rest my pelvis differently, with my rear end stuck out more than usual, which in turn made me hold my spine straighter, which resulted in me sticking my chest out a little more than normal.

Sticking my breasts out.

Any fool could see them. I had curves, exactly shaped like breasts. The cups of the bra were pushing my pecs up and in, holding me in place, and the gentle curves would be noticeable to a blind person.

From the neck down, I looked EXACTLY like a small-breasted woman.

I realized that if I'd seen me walking down the street I'd be attracted to me, especially with the hip slide that wearing heels made me do, in order to keep my center of gravity low, down in my rear end. Just a few short steps, back and forth so I could see myself from every angle, made me realize that the high-heeled walk I'd always admired and found attractive in women and found so sexy was mine to have, if I wanted it!

AND BOY, DID I WANT IT!

The dress was almost a hundred and fifty dollars, and while Leslie gave me a discount on the shoes they were still almost a hundred, and the dozen more panties I grabbed and the three bras I grabbed and the half-dozen camisoles I grabbed made the bill go even higher, and at the end of my visit I had less than four hundred dollars left to spend.

"See you next Saturday?" Leslie asked, as I was getting ready to go, back in my drab man clothes, and I couldn't nod fast enough.

Every day at work I wore panties and stockings under my office suits. And on two of those days, because it was cold outside and the heating system in our building isn't great, I was perfectly comfortable wearing a sweater to work, like most everybody else, but that meant I also got to wear a camisole underneath, safely hidden, and the touch of the material against my skin, now hairless and as smooth as glass, it was exquisite, and exciting, and kept me on the edge of orgasm all day long.

One of those two days I actually dared to put a bra on as well, preparing to go to the office and get through the day wrapped in the tightness and shaping of the cups, but at the last second I chickened out, worrying that today might be the day someone decided to slap me on the back or hug me or something physical, in which case my naughty little secret would get exposed.

At night I was home, every second in lingerie, and most of the time in my dress.

My orgasms, after hours of fierce masturbation, were always explosive. They'd consume my whole body, every muscle and tendon wracked with shearing and shaking exertion, as if my entire body was orgasming, and not just my penis.

The next Saturday Leslie had coffee and muffins ready for me when I arrived, and we spent a few minutes just chatting, about life and about the future and about each other.

I found out that she was married, to a man who did not share in her love of wearing soft feminine clothes, but who did get VERY excited when she did, which she assured me with a huge grin that she did, every day, and left me with the impression that she and her husband were still as frisky as all get out and regularly had sex, neither of them having lost the energy of their youth in that regard.

"No lie," she bragged, "some men will lose their shit when they see a corset or a basque on their partner," and she smiled, a knowing proud grin, "never mind the panties and the stockings or a sexy dress."

With no embarrassment or discomfort at all, I nodded, because I understood what she was saying on a basic level, being one of those men who would lose his shit.

But strangely I now also understood what she was saying from a second level, an additional level, as someone who was actually wearing those kinds of clothes that can drive men crazy, living on a second-by-second basis the thrills and chills of sensuous eroticism that had always bypassed me.

I was struck by one thought.

If Leslie was right, and I knew deep down that she was, that meant there would be men in the world who would go crazy, or 'lose their shit', seeing someone like me in my lingerie and my dress.

After all, since I'd arrived on day one at Rose Wind I had been going on and on in my head about how wonderful they felt and how I was wearing them every day, under my male clothes, and how they'd literally changed my life, altering my very existence, creating in me and for me a brand-new level of minute-by-minute enjoyment, making each day sunnier, no matter what was happening around me, and therefore the reaction of other men might be to be attracted to that.

I'd never really had anybody attracted to me.

It hit me hard.

I was a winner!

"So what would you like to try on today?" Leslie asked me, and my head spun around, taking in everything in the store.

The shimmering little black cocktail dress with the plunging neckline on a mannequin was almost calling out, shouting, 'PICK ME! PICK ME!'

Smiling, her suspicions confirmed, she said, "Oh yes, I know you're going to be thrilled at how that dress feels on your body, how the material touches you. You're going to be amazed at how different you'll feel moving around, and how the dress moves with you. It's a different feeling altogether from wearing pants."

And she had one in a size six.

"See you next Saturday?" she asked, knowingly, after my three-hour visit, and I'm sure my smile gave her the answer. I was almost hurting my cheeks, my grin so wide and honest and unreserved.

That next week flew by like the wind, my days productive and yet instantly forgettable, almost all of my conscious mind focussed on my upcoming cruise and how I'd be wearing as much lingerie as I could while travelling, even though I'd have to wear men's clothes on the outside.

There was no way, I knew, that I'd be able to wear a dress, or a skirt and blouse, not that I owned a skirt, or heels, while outside my stateroom.

But I was imagining hours of wearing either of my two dresses while inside my room. I'd already decided that was how my vacation was going to be.

Masculine on the outside, and feminine on the inside.

With just under two hundred dollars left on my gift card, and with my cruise starting the following week, I was carrying a little bit of sad when I walked into Rose Wind, realizing that it might very well be my last visit, but Leslie's smile and hug were more than enough to make me elated anew, while reminding me that I was a winner, even if I never saw her again or got to buy her wonderful clothes again, because I couldn't afford them.

But I was a winner, because I had her in my life, regardless of future meetings or not, and more importantly I had the life-changing results of having known her, and having had her help as I was discovering myself.

When I excitedly told her about the cruise, and how it started in just a few days, she let out a shrill scream of delight, and hugged me again, pressing her large breasts into my chest, and I wrapped my arms around her and felt her body, soaking in her softness and refinement and her delightful perfume, in her frilly mint-green blouse and dark-green skirt, and her usual tall high heels, reminding me again about the absolute pinnacle of allure and attraction that women have, and that I was beginning to feel in my own existence, my sweet and eager surrender to all things feminine.

"You'll need a swimsuit, for the pool!" she announced, all of a sudden, and wriggled out of our hug, practically running to the other side of the store, coming back with a fistful of choices, three bikinis and a few panties, plus a couple of sexy onesies, that some daring women wear, one of which was a salmony-pink color and made me fall in love the second I spied it.

But.

She saw something in my expression, and stopped in her tracks, and looked at me quizzically.

"What is it?" she asked, a little bit of worry in her voice.

"I'll be in public," I admitted, "so, um, I don't think..."

Her gleeful smile reappeared.

"It's the twenty-first century, for god's sake," she said, almost admonishing me, "and there's lots of styles of swimsuits that are unisex. That means they can be worn by both men and women. And lots of people, which includes you men, by the way, they wear them in public already, on beaches and at swimming pools, and, yes, even on cruise ships. You'll be fine."

I got the fire-engine red panty swimsuit. It wasn't quite as tiny as a G-string but it was close, and yet if I had to I could explain it away as just a speedo. At the same time, I added the pink onesie, because it made my tics and tremors ramp up a little, and with the remainder of the balance I bought some more panties, as well as a silver bralette that I could almost explain away as a tank top that had shrunk in the dryer, and lastly had enough funds to add an extraordinary pair of dark black fishnet thigh-high stockings, which were so sexy and so feminine and made me almost groan in pleasure at the thought of wearing them.

At the end, when Leslie handed me my bag, full and a little heavy, she looked at me with her softly-painted eyes and I watched a tear build up.

"I'm going to miss seeing you on Saturday mornings," she whispered, "I've really enjoyed getting to share these times with you."

I nodded my thanks, because I was tearing up inside and I didn't want to make an emotional fool of myself, until I realized that doing so would be a very feminine thing to do, something women share with each other and with the lucky men who get to be around them, so I tore down the wall I'd built up in my soul, the one that men are trained to build, and I let a tear roll down my cheek as well.

I could barely find a voice.

"I'll come back in two weeks and tell you all about my cruise," I whispered, "I promise."

She grabbed me and pulled me into her body, once again thrilling me with her breasts squished against my chest, and as I ran my hands gently up and down her back I could feel her bra straps, which, combined with her softness and the clothes she was wearing and her perfume, just everything about her reminded me of the beauty of the feminine, and how it was only with her help that I was getting to experience those joys, and how I owed her a great debt.

We parted with tears running down our cheeks.

"You better have the best time of your life," she said, her voice a little cracky, "and you better come back here again and tell me all about it," she whispered, "or I'll be mad at you."

People on the bus noticed my tears, which wouldn't stop, one old lady in the seat next to me asking me quietly if I was okay, and I nodded and tried to smile and told her I'd just said goodbye to a dear friend and I wouldn't see her for a while, and I thanked her for her concern.

That week flew by like mud.

Even in panties every second of the day and night, those tics and tremors that pulsed through me a constant joy, a never-ending pleasure, the time still dragged.

I spent every night that week packing and re-packing my suitcase. The male clothes I was taking took up about half of my suitcase, which left me room for my treasures. I brought enough panties for two a day, stockings to wear under my long pants when I was wearing them, three camisoles, two bras, and both of my dresses.

The only worry I had was that someone would x-ray my bag before they loaded it on the airplane, and they might see that a man was bringing along a pair of high heeled shoes, golden in color.

It was a risk I had to take.

Finally, the day came.

Getting on the plane was easy, and I'd been assigned a window seat. Scanning politely around as the other folks loaded on, I saw all sorts of humans. Old ones, young ones, couples, singles, a small group, some tall, some not, some thin and some sadly the opposite, some black but most white, and a few Asians. Seated next to me was an older gentleman, perhaps in his late fifties or early sixties, who was tall and thin and was dressed nicely, and who smiled at me politely as he sat down, his eyes warm behind his thick-rimmed glasses. He reminded me of a chemistry teacher I'd had in high school, who'd always impressed me with his gentle good nature.

I spent the whole flight in a titter, and not just because I was going on a trip.

The G-string panties I had on were holding me so tightly that the almost-constant chubby I was sprouting was straining to find any kind of release, either positive or negative, but neither was being given, unless I got up and went to the bathroom mid-flight to adjust, which I didn't dare do because everybody down the aisle would see my excitement.

So I spent hours on a heightened state of arousal.

At the airport, a driver was waiting with a sign for me, and a few others, in a shuttle bus, my smile getting bigger when I realized my seat mate was also aboard, as was a young couple that had been seated three rows ahead on the plane, obviously excited. She was wearing just a halter top and some denim shorts, with long thick wavy brown hair, and every man on the plane had ogled her at least once.

She had the biggest nipples I'd ever seen poking through her top.

A couple of single men got on the shuttle bus as well, and all of us rode to the cruise ship terminal. I spent the whole time wondering who might be on my ship, since I knew there were three others in port at the same time.

Getting onto a cruise ship, though, takes time. There's literally thousands of people all trying to check in, shuffling into a huge barn, and then clear customs, and even though they make it as easy as possible, assigning aisles based on the first letter of last names, it's still a momentous task herding thousands of people into the right chutes.

I stood in line with my big suitcase and my carry-on bag for over an hour. I had plenty of time to scan everywhere, watching people, and being drowned in the boisterous cacophony of humans making noise. It was like being at a rock concert, without the pyrotechnics.

A few lines over I saw the couple again, their heads and shoulders, and I could see most men and some of the women around them giving them sideways glances, and who wouldn't? She was gorgeous and sexy as hell and he was a solid-looking guy with a good tan and a lantern jaw and not horrible to look at either.

My seatmate was three lines over.

One of the single guys was in my line, seven behind me, the other nowhere I could find.

I was two people away from getting to start the boarding process when a loud angry voice could be heard up ahead of me. There was a man who was agitated, standing next to a woman who seemed confused, waving his arms a little in frustration at the person behind the counter, and obviously upset about something, but there was so much noise in the big hall that I could only make out a few of his words, one of which, 'wrong', he said a few times, in a heated voice, and then I heard him say, 'nobody told us!', and then a couple of big guys with security uniforms came in and things calmed down again.

When it came my time to step forward to the counter, I saw a stand-up sign to the left of the ticket agent.

The sign said, 'COME ABOARD! WE WARMLY WELCOME ALL OUR LGBTQ+ FRIENDS!"

While the woman in the tight skirt uniform was typing on her computer keyboard, I hemmed and hawed out of curiosity, thinking that maybe I understood why the couple ahead of me had been arguing, and finally found the voice to ask, "Um, is this a gay cruise?"

Without looking away from the monitor in front of her, the woman put on a well-practiced smile.

"No sir," she said, softly, "but we are proud supporters of that community."

Then she looked up at me.

"We proudly support all communities, of course," she explained, worrying perhaps that she'd insulted me somehow, "but don't be too surprised, you'll see some guests on this trip who are, you know, from that community."

I nodded, like it was okay with me.

Because it was.

I watched her think back to just a few moments ago, with the angry man, who obviously didn't know of the cruise lines policy, wondering.

"You were aware of our policy?" she asked, hopeful, probably not wanting another confrontation, so I just smiled and shook my head.

"It's okay by me."

Because it was.

Walking up the gangplank to the massive ship, I could see people hanging over railings, already in their staterooms, waving at people on the concourse, and my heart was beating at a mile a minute, I was so excited.

I'm going on a cruise!

I was given my room card, which was also my credit card for anything I bought during the cruise, the bill to be settled on the last day, and wandering down staircases I eventually I found my door.

Inside, it was smaller than I'd imagined, almost cramped, but then I realized that I was a winner, and it didn't matter. They'd already advised us that our suitcases wouldn't be delivered immediately, which was too bad because it was hotter than what I'd dressed for, almost stifling hot, and I was wearing slacks with stockings underneath, and would have loved to change into some short pants, but I wasn't going to let anything get me down, remembering how lucky I was to be wearing thigh-highs in the first place. I dropped my carry-on bag and almost ran out, ready to explore.

As I came out of my room, locking the door behind me, going for a walkabout, I looked down the hall, and one of the single guys from the flight was about ten rooms away, maybe a dozen, just going into his door, but he glanced my way and stopped, and then smiled, and nodded, and I waved a little wave and grinned.

I couldn't get over the size of the ship, and the amount of spaces inside. And I couldn't get over how every fifteen feet or so, on every deck, there was a hand-sanitizer dispenser, remembering that someone at work had cautioned me that cruise ships were just floating germ factories, that person advising me that I should use the dispenser every time I walked by one.

So I did.

With eyes as wide as saucers I took an elevator and started my exploration at the very top.

There were already dozens of people on the deck. I could see waiters in their formal jackets ferrying trays of drinks to various groups and individuals, folks flashing their cards to pay, laughter and raucous conversations everywhere, some folks in lounge chairs soaking up sun, several in a gigantic hot tub, and about twenty or so in the pool, men and women, all of them wearing the skimpiest bathing suits ever made, even if they didn't really have the body for it.

The woman from the plane was there, in the pool with some other young hot women, wearing what looked like two pieces of string, and that's it. Her body was, on a scale of one to ten, about a fourteen. She was built perfectly, once again reminding me of the power of the female form, the overwhelming power of beauty, and my non-stop half-erection started pulsing and threatening to go full-bore, so I turned to go somewhere else and continue my discovery, and walked straight into a man.

We both 'oomphed', and then I looked up to apologize.

The drink he was holding sloshed around and spilled a little on the deck.

He was maybe an inch taller than me and about a hundred pounds heavier, with thick glasses and a round puffy face and balding, and he was wearing an unbuttoned red and yellow Hawaiian shirt that showed his flabby hairy belly, so large it hung low and almost covered his groin, which was barely covered itself in a lime-green speedo that looked smaller than some of my G-string panties.

"I'm so sorry!" I blurted out, "I'll get you another drink!"

He shook his head at me and shrugged.

"There's plenty more where that came from," he said, almost bragging, and then seriously eyed me, up and down, ogling me, making me feel like I was suddenly in a blazing hot spotlight, a smile that bordered on threatening coming slowly and creepily onto his face, "but feel free to bump into me all you want on the dance floor in the disco tonight."

I couldn't think of a thing to say, and just stood there.

"Pretty little thing like you," he grinned, "we could have a real good time."

He said the word 'real' slowly.

R-e-a-l.

He almost purred it.

As I walked away, I saw the male companion of the woman from the plane and he was sitting in the hot tub, shoulder to shoulder on both sides with other men, all of them tanned and built and rugged-looking, all of them laughing and chatting.

By the time I made it back to my stateroom, I'd walked past the spa and the gym and the shops and the art gallery and the various little nooks and crannies where music was played at times, by real musicians and performers. I'd seen all the food outlets, some of which were open twenty-four hours a day that I planned to abuse with regularity. I'd scanned the gigantic dining hall, where I was booked on the late seating, at seven p. m. I'd seen the casino and the photo studio and several lounges and the library and the huge main showroom where the big entertainment happened every night. I'd found the medical clinic and the pharmacy too, by accident, but realized it couldn't hurt to know those things.

Sitting on the bed in my stateroom, I should have been walking on air, seeing all the facets of a floating city, knowing that I was going to get to enjoy them for four days, living like a king.

And I was walking on air, but not entirely in the way I was expecting.

Not totally.

Mostly my spirits were soaring in the strangest kind of glee and concern fused together.

Pretty little thing.

The man had called me that.

A pretty little thing.

For almost an hour I sat and stared at a wall with a glazed look on my face and kept asking myself the same question, over and over again.

Was I?

Was I a pretty little thing?

And okay, it was easy to say no, I wasn't, because I'm a man, with a plain kind of face. I'm nothing remarkable. So I couldn't possibly be pretty.

What worried me was a sudden and nagging thought.

Has wearing lingerie and blouses and dresses and high-heeled shoes somehow changed me in some way that other people might be able to notice?

Has exploring femininity and the sensual thrills of women's clothes somehow given me some sort of different persona? Am I carrying around a 'pretty' aura now? Am I glowing with previously-unrealized non-masculine light? Is that even possible?

At the required muster drill, before leaving port, I joined a crowd of passengers on the outside deck, one floor up from my stateroom, with my floatation device properly secured on my body, and listened to the little speech from the crew member about what to do if there's an emergency.

When she was finished, the huge shoulder-to-shoulder crowd all tried to get in through the same doors at the same time, and I ended up hanging back a little bit, just to avoid the crush, finally joining about a hundred people in the elevator lobby, six different cars ferrying people up and down, when I heard a voice from behind me.

"Hello again," said my airplane seat-mate, his bulky life vest making his head look a little small on his tall frame, "have you seen all of the ship yet?"

So we chatted briefly about the amenities, both of us almost giggling at the opulence of things, and then he stuck out his right hand.

"I'm Perry, by the way," and I put my hand in his and we shook, and I introduced myself.

"Justin."

His hand was warm, and surprisingly soft. Not Leslie level, but close. I liked it.

We held hands for a little bit longer than most people would consider appropriate.

I found out he was, like me, doing dinner at seven, and he explained that the first night was a sit anywhere process, as opposed to all the other nights where seating was assigned, things casual today because of the last minute rush of arrivals just before the ship left port, so I offered to look for him and Perry smiled and said he'd do the same.

My suitcase was in my room when I got back, and that, I knew, was the final stick of dynamite in the bomb of my life, and I was set to explode.

Life was about to get exciting!

I was on a cruise!

I hung my clothes carefully in the small closet in my room. I made sure my two dresses were properly aligned on the hangar, with no bunching or wrinkles, and hidden as much as possible by my men's clothes, just in case the cleaning staff looked inside during the days. I filled the four drawers carefully, making sure none of my lingerie would wrinkle, not giving a hoot about my man clothes.

I took a long shower, in a very cramped space, and shaved every inch of my flesh, from the eyebrows down, and I flashed back to that day in Rose Wind, with Leslie telling me how she adored the few minutes it took, and once again I thanked my lucky stars for having met her and for her encouragement and wisdom to help me find the new path of femininity that I was on.

Sliding a truly sexy pair of silky off-white panties on was divine, equally matched by the thigh-high stockings sliding up, those joys only diminishing a teeny bit with the addition of men's pants, but with a silk blouse that I could say was a man's shirt if I had to caressing my skin everything kicked back into high gear, and with a dare I decided to not wear socks, the hem of my pants long enough to cover my ankles above my shoes, so no one could see my bravery.

I wanted to slip a camisole under my button-up shirt, but at the last second decided to play things safe.

I was already quivering with tics and tremors in every direction, on a cruise ship wearing lingerie! There was no need to risk getting caught, and nothing but delicious thrills ahead of me anyway.

At the stroke of seven I walked through the doors of the gigantic dining hall, and scanned for Perry. The Maitre'D smiled warmly at me and asked if I was with any particular party, and as I began to explain that I was hoping to see someone I knew while scanning all around the vast room I spotted him, so I pointed and walked to the table.

Perry stood up to shake my hand, and said it was good to see me again, and I felt like I'd also won a very nice new friend, on top of winning the cruise, but then he wouldn't sit again until I was sat, even offering to help push in my chair, a new moment in my life experience, and I almost flushed with color and heat at the idea of it. My parents had raised me to follow all the masculine protocols, of course, so I was supposed to be the one who opened doors for women and gave up my seat on the bus for women and pushed in chairs for them, and had done my whole life.

Having it done for me, though, felt foreign, and yet totally and utterly and giddily delightful.

We fell into an easy conversation about how interesting it was that we were both on the same plane and the same cruise ship and obviously from the same city, and we talked about neighborhoods and local things for quite a while.

Perry lived in a quiet area, next to a municipal golf course, while I barely existed in a dump.

Then he asked me about myself, so I gave him the short version, with the loose background, not mentioning the exact location of my apartment, embarrassed about it, and then I got excited as I talked about my winning streak, the barbeque tools and the cruise, although I left out the gift card and all the clothes.

He gave me the short version of his background. Fifty-eight, almost retired after a long career as a paramedic supervisor after years of being on the streets as an actual paramedic, with two children and four grandchildren.

There was a genuine warmth in his voice as he talked about his kids, a pride that beamed like the sun.

Then he mentioned that he was treating himself on this cruise, and he'd booked an outside stateroom with a veranda.

"You're obviously travelling by yourself?" he asked, and after I nodded I asked the same question of him, and he nodded, slowly.

"My wife passed away, eight months ago," he said.

"OH NO!" I almost yelled, "I'm so sorry to hear that."

He put a forced grin on his face and held up his hand, as if to say things were fine.

"Thank you," he breathed out, "it's been getting easier and easier, I'd like to think. We were married almost forty years. We'd talked lots of times over the years about doing a cruise together, but with work and the kids and grandkids we always found an excuse not to go. So after she passed," he said, and then paused, for a big breath, as if he was getting emotional, or getting ready to say something he didn't want to say, or admit, "well, it was one of a couple of reasons why I booked the trip. For the most part, I'm fulfilling a promise I made to her, something we'd always said we'd do, even though she's not here. I thought starting out with a four-night cruise would be a good test run, a short trip, to see if I like it. If I do enjoy the overall experience, then I'll seriously think about booking another cruise I have in mind that I might do next year."

"To where?" I asked.

Perry smiled, almost bragging.

"Seven days in the Caribbean."

There was no way I could ever afford that, but I imagined it must be wonderful, and said so.

"What was the other reason?" I asked.

"Other reason?"

"You said your wife passing was one of the reasons you booked this cruise. I was just wondering what the other reason was."

For a few moments, I worried that I had been too nosy, gone too far, and had offended him, based on the silence and the look on his face.

"I'm sorry," I blurted out, "that's none of my business."

His smile to me was warm and apologetic, and I saw him come to some sort of a decision.

"No, it's fine," he said, in an almost-comforting tone, "the other reason is something I've dealt with now for many years."

Then he gave a little chuckle.

"Or haven't, actually."

He seemed as if he was measuring his words, in a respectful way.

"I hope that this doesn't offend you, or lessen your opinion of me," he said, slowly, "but after almost forty years of marriage to a woman, I finally found the courage to face up to what I am. To who I am. I took all my sorrow and grief and used it to find the courage to acknowledge what I really want, in my life. What I've always wanted in my life, but never had."

After a few moments, I had to ask.

"And what is it that you want?"

Perry took a deep breath, and then sighed, and fixed his eyes on me, seriously.

"I was born and have always been a homosexual."

By this point we were both enjoying our appetizers, and I stopped chewing, for a second longer that was standard.

Continuing, Perry said, "I've always known that I was attracted to men, certain men, romantically and sexually, from my very first recollection. But in my generation that just wasn't done. Don't get me wrong, I'm not foolish, there were gay men around, of course, there always has been, but they were hidden. And in my world, my family, my upbringing, my profession, my community, there wasn't any possibility for me to pursue what I really felt inside, what I truly yearned for. So, like so many other men the whole world over, I stayed hidden, in that horrible closet, and lived a completely heterosexual life, happy enough I suppose, but always with a lurking sadness. I did what I had to do, what the rules said I had to do. Marriage to a woman, a house, kids, a mortgage, the works."

I thought about the sign on the counter when I was checking in, and how the cruise line was LGBTQ+ friendly, wondering if he chose this particular trip for that reason.

"I doubt very much I would have ever found the guts to come out of that closet, if my wife hadn't passed," he admitted, his eyes flicking on and off mine, trying to gauge my reaction without putting any pressure on me to react one way or the other, "but, as they say, with every door closing there's a new one that opens up."

I asked the first question that came into my mind.

"Are you meeting someone, here on the ship?"

Perry shook his head.

"No, no, nothing like that," he replied, and then looked wistfully off into the distance, "but I wouldn't be upset in the least if it happens."

Then he stared at me, as our entrees were being served.

"And you?" he asked, the subject of the question obvious.

"Me?" I asked, surprised that someone would want to know anything about my personal life.

Perry waited for an answer.

"I don't know what to say," I admitted, "I'm not, you know, I'm not... well, I've never been married, like you were... I've never even been involved like that with someone, well, a woman, other than a couple of short relationships here and there."

His focus on me got stronger.

"Really?" Perry asked, "I must say I'm surprised."

And that surprised me.

"Why?" I asked.

"Well," he began, and then hesitated while he thought of what he wanted to say, "you're a very nice young man, very polite, and pleasant to look at. And even though we've only just met, I get the sense that you're also a kind, thoughtful person. Those are all attractive qualities."

I nodded my thanks, and with surprise in my voice, I asked, "you think I'm pleasant to look at?"

He studied me with a kind of gentle glow for more than a few seconds of silence.

"I think you're a very nice-looking man," he said, his voice quieter than conversation level, "very attractive, and please don't think of me as rude, but I would even go so far as to use the word 'lovely', in some ways. In certain lights."

The tics and tremors were making my rear end do the slidey thing again, in my chair, and I could feel myself get erect instantly, constrained in the most exquisite way by my panties, and I didn't need to look down to know my nipples were pebbly-hard, and probably showing through my button-up shirt.

"I hope I haven't offended you," he added.

Without thinking about it, I shook my head.

"No," I said, my voice also a little quieter, "of course not, not at all. I'm flattered."

Perry and I gazed at each other, silently, for several minutes, as we ate our food, the both of us only breaking our stare to take forkfuls of the seafood pasta.

I watched his lips form into a smile at his first taste.

"Mmmm," he hummed, and about a second later I felt the delicious combinations of tastes and spices and sauce hit my taste buds and I hummed as well.

We ate in silence, surrounded by the din of hundreds of people talking and clanking silverware on china, waiters and servers whizzing past us non-stop, occasionally flicking our eyes beyond the other, mostly when somebody around us laughed loudly or made some sort of raucous comment, but we mostly gazed at each other.

I sat, twitching in my panties, looking at a man who struck me as gentle, a real gentle man, and was happy to silently communicate with him while we ate.

To my extraordinary surprise, I was silently communicating that if I ever did have a relationship with a man, something I'd never considered until just recently, then I'd be grateful if it was with someone like him, someone older and perhaps more experienced, someone kind and well-mannered and respectful.

"I chose this ship," he said, after almost all of his dinner was gone, "because it is LGBTQ+ friendly, as all the signs in the terminal say" and then he smiled, "and, please, correct me if I'm wrong, but I feel safe in assuming that you were unaware of that policy? You didn't choose this ship or this trip based on that consideration? Would that be fair to say?"

I nodded, slowly.

"Yes, that's fair, because it's true," and then I added, "but, I'm not against it like that guy in line, not at all. Quite the opposite. I'm all for it. I've always believed that people should, you know, be who they are. They shouldn't have to hide anything, or be ashamed of anything."

Perry's smile got warmer and bigger.

"I'm glad to hear that."

"And, the thing is," I continued, "I've never, you know, I'm not gay, so it's not something that I've dealt with in the past, not being part of that community," using the word the check-in lady had used, "which makes it interesting, being new to dealing with it today, and maybe the old me might have reacted negatively, but", and I paused, "and, it's funny," and I leaned a little closer, wanting what I said to be more intimate, "this afternoon I was up on the pool deck and I accidentally bumped into a man and sloshed his drink, so I offered to buy him a new one and he said no, but then he invited me to bump into him on the dance floor in the disco."

Perry smiled.

"He said we would have a r-e-a-l good time," I added, "and I'll admit I was surprised, of course, startled even," and then I decided to go for broke and said what was in my heart, "as a matter of fact, he called me a 'pretty little thing', which I'd never heard before and, honestly, has been in my head ever since, but the thing is, I wasn't shocked at the idea of bumping into another man on a dance floor, in that kind of way I'm sure he was suggesting, no. I mean, don't get me wrong, I've never done that before, ever. I've never been, you know, in any kind of relationship with another man."

"No?"

I shook my head.

"No. But, well, here's the, well, the irony, I guess you'd call it," and then I realized that the best words were the most honest ones, "lately, the last few weeks actually, I've gone through some, well, some changes, I guess you'd call them, some significant changes in my life and in my outlook on things, and so the idea of it, the idea of, uh, let's call it 'interactions' with other men, that idea has gone from 'never-ever-thought-about-it' to 'definitely-thought-about-it'. If I'm being totally honest."

Perry gazed at me, with a soft smile.

"But no word of a lie, I was gobsmacked that he was, you know, hitting on me in the first place. I've never had that happen before, or even considered that a man would find me, you know, worth being interested in, so that was a totally new freaky kind of experience."

"And?" Perry asked, almost playfully.

"And what?" I asked.

His gaze got warmer.

"If I go to the disco tonight," he began, "am I going to see you bumping into him?"

I had no filters that kicked in.

"No way," I said, perhaps little harshly, and saw Perry's eyes react, as if he'd been expecting a different answer.

"Oh," he said, a little disappointedly, "so these changes you mentioned," and he paused, "I'm sorry, I just assumed, based on what you were saying, that you were now perhaps intrigued with..."

I interrupted him.

"Oh, I am intrigued," I admitted, out loud, for the first time ever, to an almost complete stranger, "don't get me wrong. I'm interested. I mean, I'm nervous beyond imagination at the thought of it, but I'm not going to lie. My life has had some changes in it, so the idea of doing something with another man is new and a little scary, that's all. If it happens, okay, I'll learn and deal with that. But not with him," and then I added, after a long pause, "he's way too fat and hairy and ugly for my liking."

For a second or five, we just stared at each other, and then at the exact same time we both burst into laughter.

As we sipped our after-dinner coffees, Perry looked to me like he wanted to ask something, but was hesitating, so I asked him what he was thinking.

"I was just wondering," he said, "what kind of man you would be interested in, if you're at that point."

Humming an 'mmm' with the last of my dark rich coffee, I looked at him and smiled.

"I'm not saying anything would happen," I replied, considering my words carefully, "it's all so new to me, and I have no experience and might not even know what to do. But if it did happen, if I was going to bump into someone on the dance floor for those reasons, ideally I suppose it would be someone more experienced, someone who is older, someone who has patience, someone charming, and, most definitely someone who doesn't look like a hairy ape."

After a long silence, in no way awkward, Perry folded up his napkin and placed it gently on the table.

"Justin, I can't thank you enough for sharing your dinner with me. I had assumed that I'd be dining alone, to be honest, or worst case paired up with someone I didn't find any connection with, but this has been most enjoyable."

I nodded my agreement.

"I still have some unpacking to do," he said, with a small amount of finality, and he pushed his chair back and rose to his feet, "but I'll be out and about after that, so I'm sure we'll run into each other again."

"I hope so," I said, quickly.

Perry raised his eyebrows and smiled.

"Perhaps we'll bump into each other in the disco?" he asked, rhetorically, before saying, "enjoy your evening, Justin."

The tics and tremors were galloping through my skin, from head to toe, and I realized that I was once again as erect as I'd ever been, so I sat at the table and gazed out the window at the Pacific Ocean with the sun setting off to my right, until the lump in my pants became less obvious.

Back in my stateroom, I practically raced at light speed to put a bra on and my golden dress and heels, and spent probably over an hour just walking back and forth in the cramped space, sliding my hips to and fro, really working a strut, which excited me for so long until the point where I was finally unable to delay the inevitable, so I took the dress and the bra off so they wouldn't get stained and lay on the bed and masturbated myself with a frenzy, furiously peeling my foreskin back with every pull, almost to the point of pain, sparking rivulets of pre-cum to ooze out of my pee-hole, creating a small lake on my smooth hairless tummy, thinking of Perry, or someone like him, imagining being held and kissed and made love to, the new feminine me reveling in a euphoria of lust, until I let myself go, emotionally and physically, blasting a veritable puddle of my own semen all over my chest, the first shot actually pooling on my neck before sliding down and away, an explosion so fierce and tumultuous that I more-or-less passed out for a few seconds, and left me groggy with delirium.

For close to the full next hour, after another shower and shave, I ran a raging battle in my mind about what to wear to the disco.

The majority of my practical mind knew that I should wear men's pants and shirt, with some panties and thigh-highs underneath, but the recently-born feminine side of my brain kept saying things like, 'it's an LGBTQ+-friendly ship, so it's okay to be more open, more flamboyant, and more daring! Wear the dress! With your heels!'

My practical mind won out.

Even in March the weather was warm off the California coast so I took a long walk outside around the ship on two different levels, enjoying the fresh air, smiling and nodding and saying 'hello' to everyone I passed by, at one point seeing the single guy from the plane whose stateroom was down the long hall from me, as he walked with another man, their casual conversation made with what looked like glee and joy, and why wouldn't they?

Like me, they were being treated like royalty!

I spent about an hour just people-watching, on a variety of decks, and poked my head into a lounge where I could hear someone playing a piano and singing, quietly, which turned out to be a small room with space for maybe only twenty people or so, which was three-quarters full, couples and singles and small groups, most of them grey-haired and none of them even giving me a second glance.

By the time I got to the disco, it was jumping.

Wall-to-wall people were partying, the whoops and laughter of the crowd almost as loud as the thumping disco music, bodies crammed onto the dance floor, a dazzling display of colored lights above them changing as fast as the music, and on an inner level I could feel the energy in the room, the intense combination of disparate humans gathered together in search of excitement, most of them affected to some degree by alcohol, and the unmistakable vibes of lust and the laws of attraction and the manufactured sense of anonymity that a cruise ship offered all melding into one big gigantic aura of fun.

I didn't see Perry.

I didn't see the man from the pool deck.

I did see the woman from the plane again, wearing the tiniest and sexiest little black dress in the world, braless and probably pantie-less, dancing with a small group of other women in a group, the way women do sometimes, all equally presented, all of them dressed to kill, all of them in close quarters, bodies bumping and touching, as they bounced and laughed and caroused.

For the most part the dance floor was full of the traditional man/woman partnerships, but to my great delight there were a few scattered same-sex pairs, men obviously dancing with men, and some individual ladies doing the same.

The spinning disco ball on the ceiling was casting the familiar moving spectacle of lights on every human there, including the waitresses and waiters who were carefully squeezing between people with their trays of drinks, experienced moves learned over time, in order to not spill anything or waste the ships supplies, so I stopped a smaller man with the nametag of 'Boodi', and asked him for a Pina Colada, mentally deducting the cost from the small amount of available money I'd saved and put on my credit card before the trip, reminding myself that I'd planned on two drinks an evening, maximum, so I'd work extra hard at enjoying the drink.

When the DJ played YMCA the boisterous crowd on the tiny dance floor got bigger, way more people than was necessary literally crammed together, bodies jumping and shaking and touching, and while I hadn't planned on dancing I was swept up in the rush of people weaving through the tables and chairs and basically pushed onto the floor, holding my drink with one hand and only spelling out half of each letter when it came time to do it, and I found myself surrounded by men and women, everyone loud and uninhibited and surrendering their propriety.

It was only for a few seconds, but through gaps in-between people's moving heads and bodies I saw the woman from the plane wrap her arms around an equally-gorgeous woman, with long black silky hair, another fourteen on the scale, and the two of them kissed, with closed eyes and for more time than would be considered normal, and just before I lost sight of them I saw their eyes open as they stared at each other, the most profound glazed look on their faces, totally enraptured with each other.

My constant partial erection went full-bore.

Whipping my head around I looked for her man, but didn't see him in the crowd, although there were so many people I might not have seen him even if he was standing less than a few feet from me, but for a few seconds I had a bunch of thoughts blaze through my mind.

Maybe they weren't a husband and wife or girlfriend and boyfriend. Maybe they were just friends, with no commitments to each other.

Or, maybe they were partners of some sort and they had permission to enjoy whatever came their way. Maybe she was bisexual, or had leanings that way, and this was her chance to explore? Then I remembered him from earlier in the day, sitting tightly shoulder-to-shoulder with men in the hot tub, and wondered briefly if maybe they both weren't on an LGBTQ+ cruise line for the same reason.

I danced with the crowd for a bunch of songs, the old standard disco hits that everybody knows, and bumped up against men and women both. But other than the heat of the moment, I didn't feel anyone was touching me for any specific reason, and with a sheen of gentle perspiration on my forehead I finally wandered away to catch my breath and finish my drink.

When the waiter asked me if I wanted another one, I declined.

The excitement of the day, the long flight and all the new moments I'd been going through, made me realize that I was dog-tired, and it was getting late, and I'd be waking up in a new port soon enough, and I didn't want to sleep in and miss any of it, so after a casual walk around three of the decks again, seeing hundreds of people but no one I recognized, including Perry, some dressed up and some not, I eventually retired to my stateroom, delaying my sleep long enough to hurriedly masturbate again, with ferocity, on the bed, staining one of the cups of a bra I'd thrown on with a big blorb of my own cum, unable to control the strength of my explosion or the quantity.

I fought sleep long enough to wash the bra gently, and hang it to dry on the slim door of the tiny shower.

My dreams were exotic, and while I couldn't remember much of the details waking up, I somehow knew that they were heavily laced with lingerie and women's clothes and me wearing them.

After breakfast, I lined up with hundreds of other people to get onto a tender, which is a small vessel that carries about twenty people or so, maybe a little more, to the actual pier of Catalina Island, since the cruise ship was too big to dock. I had on a golf shirt and some man's short pants and sandals, though underneath I was wearing panties, of course.

The harbour was filled with boats, some of them huge yachts that all looked tiny compared to the cruise ship, and there was a long main drag filled with little stores and shops and restaurants, with the round domed former casino building at the far end. Strangely enough, there were no cars anywhere, only golf carts, except for a few small buses by the pier, which I assumed were for people doing excursions. The sun was shining and there were people literally everywhere, which made the going slow, but that was just fine with me.

I poked my head into every door along the strip. I couldn't afford to buy anything that anybody was selling, but it was enormous fun to be a looky-loo and dream. And of course most of the retail shops were filled with touristy-kind of goods, sweatshirts and t-shirts and hats and knick-knacks all emblazoned with the word, 'Catalina', on them.

Until.

I came to a full-stop in front of a window, causing someone behind on the crowded sidewalk to bump into me, which was not their fault, so I apologized and shuffled a little closer to the store-front to get out of people's way, hypnotized by what I saw.

On a mannequin lay a dress that stunned me with its femininity and design. Shimmering like sunlight sparkling off of water, the plum-colored wrap-around gorgeous material looked as light as air, and I coursed with tics and tremors imagining the material on my smooth skin, and how it would be heavenly to wear.

I stood for a long time, as if there was no one else and nothing else on the planet, my mind racing with different scenarios, all of them involving me wearing the dress, and most of them including interested male companionship.

Finally, my brain inner-slapped me and reminded me that I was in public, and I was just about to move off and continue my walk, when I heard a familiar voice from behind me.

"It's a pretty dress, isn't it?"

Turning in surprise, I saw Perry, not more than a foot away.

Suddenly worried about my lack of discretion, and getting caught doing something 'normal' men weren't supposed to, I stammered and stuttered a reply.

"Y-y-yes, I guess it is."

Behind dark sunglasses, I could almost see his eyes light up.

"I'd wager folding money that you would look beautiful in it."

My eyes must have opened as wide as garbage can lids, which made Perry react as well.

"I'm sorry," he said, his voice quiet, "I don't mean to embarrass you," and he slipped his sunglasses off, his warm hazel eyes fixing on me, "it's just, well, last night, when I was pushing in your chair, I looked down and noticed that you were wearing hosiery, not socks, either pantyhose or stockings, and that, combined with what you mentioned about the changes you've been going through, and then seeing you standing there staring in awe at that dress, I put two and two together, and I hope I haven't added up to five."

I couldn't look away from him, but I couldn't think of anything to say. I wanted to admit to him that he was right in his presumptions, for a second admiring his perceptive abilities, but at the same time the old standard rules of the road and how I'd been raised rose up, those conflicting pressures of biases I lived with, and while last evening I'd been brave enough to publicly admit that the idea of a different kind of lifestyle and sexuality was something I might be interested in pursuing, going the next step and admitting out loud to my new life-consuming addiction to cross-dressing was an even bigger step, and one I didn't want to be ashamed of, in any way.

But truth won out, in the end.

I looked from him to the dress and back again, seeing nothing but support in his face.

"No," I said, "you didn't come up with five."

Perry's smile got a little bit wider.

"So why don't you buy it?" he asked.

Suddenly, I was filled with a different kind of shame, or embarrassment, and I felt the skin on my face flush with red.

"Well, the truth is," I said, "I can't really afford something like that."

He nodded slowly, as if he understood.

So I explained, that I didn't make a lot of money in my job and could never have paid for the cruise, and if it wasn't for the winning ticket I wouldn't be there at all, and then I said, "but you're right, I have been, um, exploring things, including wearing clothes like that, because I also won a gift card to a store that sells women's clothes," and I talked a little bit about meeting Leslie and initially trying some items, just for the feel of the fabric, finding the backbone enough to admit that the effect of the garments went way beyond just feel, and how they'd been the catalyst for my other changes of attitudes, new desires appearing where they hadn't existed before, or at least hadn't surfaced before.

Perry was about to say something, when he stopped and quickly checked his wristwatch, and then apologized and said he was on an excursion and had to run to catch the bus, but that he hoped to see me again later, and I assured him that I would like nothing more.

Looking back at the dress, I shrugged to myself and thought, 'oh well, maybe someday'.

Even walking slowly and stopping in every shop, it still only took me a couple of hours to explore the main drag and the few little side-streets behind it, and once I'd exhausted everything to look at I caught the next tender back to the ship, and spent the rest of the day either in my stateroom prancing around in a dress and heels and masturbating to an enormous climax, or wandering the different levels of the ship back in male mode, smiling at all the different faces I saw, reminding myself that I was a winner, and being treated like a king.

There was an old movie playing in the ballroom, and a few dozen people watching, but I'd seen it before and didn't feel like sitting.

On the pool deck, I paid for another cocktail, since I'd only bought one last night, and lay on a lounge chair, soaking up the sun and people-watching. Humans of every shape and size were on display, themselves revelling in their own enjoyment of the luxury, and while I didn't see anybody I knew, even a little, I did see some familiar faces, people who'd been in the lines with me at receiving or people I'd passed whilst walking around the ship.

A small group of women, some old and some younger, were off to one side of the deck, all with mats on the flooring and all of them doing yoga, all of them in activity-appropriate tight clingy clothes, in some positions stretching their bodies to extents that allowed me to ogle their femininity discretely, breasts thrust proudly forward, and crotches openly displayed, which, added to the steady stream of men wearing almost nothing, just boards shorts or tight swimsuits, hopping in and out of the pool or hot tub or just walking by, some of them with gym-built bodies and some not, some of them with seriously-large lumps in their suits, and for over two hours I sat with a pulsing half-erection in my panties.

I had another glorious masturbation session before dinner.              

Sadly, even though he was in the same seating as I was, Perry was not at my table. I scanned the vast room and didn't see where he was, but there was so much to see and so much movement of staff that it didn't surprise me. My dinner companions were a mix of people, couples and singles, and the conversations were pleasant enough.

One of them was a travel agent, she and her husband on their twenty-sixth cruise, and when she found out it was my first she cheerfully explained that I should feel extra-specially lucky, since, in her words, this wasn't a 'normal' cruise, explaining that because it was a repositioning trip it wasn't fully sold, and instead of the normal load of over two thousand guests there was actually only just over half of that, but still with a full complement of staff, meaning there was a crew member for almost every guest, which meant less lines and better service.

"Don't think it's like this every time," she said, "most of them are w-a-y more crowded."

It wasn't formal dinner night, so once again I was in a casual button-up shirt and slacks, and once again I'd dared to wear stockings and no socks, just in case I saw Perry, not wanting to disappoint him, since he knew my secret and didn't seem to object to it in any way.

After dinner, and more than an hour in my stateroom, fully dressed and strutting in heels and once again masturbating to a body-stiffening orgasm, I showered and shaved and got back into man clothes and went for a walk, where I saw something that made me go instantly erect in my panties and forced me to do a quick grab at myself again, for fear of having an accident on deck.

Two men, complete strangers to me, probably in their late twenties or early thirties, were on an outside deck, casually walking and chatting with each other, when they got to a point where there was less light, some of the bulkheads sticking out and forming a short stretch of semi-darkness, and one of them felt inspired enough to look quickly around, scanning for any nearby potential witnesses, obviously not seeing me, before he stopped and slid his arms around the other man, who eagerly accepted the hug, the two of them gazing into each other's eyes for a moment and then kissing.

KISSING!

I stood there in abject awe, hard as granite in my panties, a tent in my trousers, after slipping into my own little dark area twenty feet away, pretending to be gazing at the ocean, but concentrating on the most erotic sight I'd ever witnessed, or could have imagined.

It wasn't a little peck, either.

They were lip to lip, firmly and yet gently, eyes closed, slowly pursing and moving from side to side, until after a minute or two I could see their mouths open, just a little, tongue tips emerging and meeting.

The tics and tremors I was walking around with on a minute-by-minute basis went nuclear and my whole body shuddered, and again I had to grab onto my erection through my pants, gripping with all my might, just to abort the rising blast within me.

When they broke their kiss, even from a distance, I could see that they would be making love soon. It was an easy bet, a lock, that they were going to be having sex with each other. You could just tell. They both had that lust-filled glassy expression, the easy grins, the wet lips, and the rosy cheeks.              

Later, I heard a woman's lovely voice accompanied by a piano on an upper deck, and stopped in to enjoy the music, paying for another Pina Colada, which I sipped slowly while she finished her set, and then carrying it with me as I walked around, smiling at people and slowly making my way to the main showroom, where there was a variety performance scheduled, based on the hits of Motown. There were very few seats left, so I slipped into one at the back just as the lights went down and the band struck up.

Just over an hour later we all streamed out, after a great show, a couple of hundred people laughing and shouting and celebrating just how lucky we all were to be living like kings, some folks heading to their rooms but most spreading out to various other places, any one of the lounges or the disco or the food deck.

For some reason the idea of bumping into someone, anyone, but especially another man, at the disco, was uppermost on my mind, and made my choice the easiest I've ever made.

I had no idea if it would even happen, and absolutely no idea how I'd actually react if it did happen, but hope springs eternal, and I was travelling on that road feeling languid, and feminine, panties and stockings on.

I'd almost arrived when I saw Perry.

"How was your excursion?" I asked, and he smiled and happily told me about seeing most of the island, including the huge mansion built by the Wrigley family, who owned the island for a time, before asking me how the rest of my day was, and I couldn't find enough good words to describe how I'd felt then, and still was feeling, just being lucky enough to be on the vessel.

"Oh," he said, as if he'd just thought of something, "I have a surprise for you," and then made me promise that I'd stay right where I was while he went to get something, which he'd promised to only be a few minutes but which turned out to be closer to fifteen, which I spent people-watching, the partiers, the passers-by, the staff hustling here and there, still amazed and awed that I was lucky enough to be there in the first place.

When Perry came walking back towards me down the long hallway, he had something in his hands. As he got closer I could see details.

It was a rectangular white box.

It had a silk bow around it, baby blue and flowery.

Even upside down, and partially covered by the bow, I could still read two words.

The name of the shop on Catalina Island.

As he handed me the box, Perry smiled brighter than all the other smiles I'd seen from him so far.

I gasped out loud. It suddenly struck me what he'd done.

"Is that...?" I stuttered out.

"For you," he said, "the dress you were staring at. I hope you enjoy it. I had to guess at the size, but there was a young woman inside who was quite helpful. I estimated your height and weight and she came up with a size six."

I looked at him with shock.

"You shouldn't have, you really shouldn't have," and then I remembered how much it cost, gasping out, "it was s-o-o expensive!"

Perry leaned closer to me.

"I've done well, over the years," he almost-whispered, "and to me it wasn't expensive at all."

For the longest time I just stood there and held the box in both hands, feeling the gorgeous feminine aura of the dress seeping out through osmosis and then spiraling through my veins, like a drug, a sensual narcotic sending my non-stop tics and tremors into a tizzy.

"I don't know what to say," I breathed out.

"Say that you'll wear it," Perry replied.

I almost sprained my neck, I was nodding so hard and fast.

"And perhaps," he whispered, "if it pleases you in any way, perhaps you'd allow me the pleasure of seeing it on you?"

I just stared at him, mouth slightly open.

"I'm not pressuring you," he added, holding out both hands in the surrender pose, "please don't misunderstand me. There is no quid pro quo here. I don't expect anything, or demand anything. It's a gift, from me to you. That's all. Without obligations."

I just stared at him more.

"But I confess I wouldn't pass up the opportunity to see the end result," and then he paused, "because I suspect you would be lovely to look at."

I continued staring, desperately searching for words, but only the right words, conflicting thoughts and images battling out in my head.

"Justin, I know that you are going through changes, as you mentioned, as regards your lifestyle and your choice of clothes, and perhaps your sexuality," and then his voice got quieter, "and I'm not naïve, it's entirely possible you have no interest in any sort of a relationship with someone like me, someone as old as me, but..."

"YES!" I said, loudly.

Perry's head rocked back a little, at my abruptness.

"Yes?" he asked, tentatively.

"Yes!" I confirmed, "I mean, if you actually want to see me wearing it, if that's something that you'd like, then I'd be happy to show you. Of course."

He looked at me with what I felt was an enormous amount of affection.

"I'd be nervous as hell and shaking like a leaf, probably," I admitted, "but if I'm the kind of person," and then I shook that off, "the kind of man, if I'm the kind of man that you're attracted to then yes. Yes. I'd love to."

His eyes seemed to burn with a fire.

After more than a minute of just staring at each other, people passing us by, most loud and boisterous but some not, Perry asked me what I liked to drink, and then told me his stateroom number.

It was on one of the upper decks.

The expensive ones.

Even though I'd recently had a shower, I asked him for enough time to clean up and get ready, so we agreed I'd visit him in forty-five minutes.

Back in my little stateroom, I threw off my man clothes and ripped the box open and slipped the dress on faster than anything in the Guinness Book of World Records, grabbing at my erection with both hands to stave off the impending gut wrenching cum I was about to have, and felt the material against my skin, as light as a feather, satiny and gentle, and yet with a heft and weight that transcended reality, turning my previous thirty-three years of bad luck into nothing but joy.

Sad sack?

UH-UH!

Not anymore!

As much as I'd wanted to, I couldn't wear the dress in the elevator, or down the halls. I didn't have quite that much nerve. But after a shower and another shave, because, just like Leslie had taught me, there aren't words to describe the feelings of soft silk on smooth skin, I'd changed into my sexiest bra, panty, garter belt and stockings, silky soft, black as coal, with lace everywhere, and I didn't care if other people noticed any impressions of straps under my golf shirt and chinos as I carried the box with my high-heels carefully placed inside to Perry's room, taking me through the ship, including on an crammed elevator.

The way I was feeling, excited and desirous and anticipating what might be the most thrilling moment of my life, combined with the fact that the cruise was on a gay-friendly trip, and everyone, including me, had to have seen at least some same-sex behavior on-board, men hugging and kissing and celebrating with other men and some women doing the same with other women, in the rainbow of varieties and deviations that exist, I decided that people seeing a man who was obviously wearing women's lingerie under his normal clothes wouldn't be anything overly shocking.

I also didn't care even if it was shocking to some.

I didn't care if they noticed my erection either, which I know a couple of people did. I watched their eyes.

They knew.

When I knocked on his door, Perry welcomed me in, and I saw his eyes notice the obvious lines under my shirt, the bra straps, and a flicker of something shot across his face.

I got the distinct impression it was a very welcomed flicker.

He had a much bigger stateroom than mine. Never mind the sliding glass-door leading to the balcony, he actually had wide room to walk around, and he had a small love seat and easy chair and coffee table, an actual space to relax other than lying on the bed, and the television monitor was huge compared to mine.

After offering me a drink, his mini-bar fridge also bigger than mine, he nervously asked me if I wanted to change my clothes right away, or if I wanted to wait, and before I could answer he blurted out that there was no pressure to even do it, that if I'd changed my mind or was not comfortable anymore with the idea that he'd totally understand.

My heart answered for me.

"No," I said, softly, "I would really like to wear the dress for you."

He offered the bathroom, his slightly bigger than the ones on lower decks, or he could go out on the balcony and watch the ocean roll by and I could use the main room, and I chose the bathroom, and with non-stop pulses of nervous electricity jarring like earthquakes through me, I quickly shed my boring man clothes, never happier to get rid of them, and, after staring at myself in his mirror, my lingerie silky and as feminine as I could dream of, my imagination running wild with what might happen later, I carefully opened the box and took the shoes out and then the dress, last-minute checking for any tags that might still be on it and happy to find none, silently thanking the sales woman he'd mentioned for her attention to detail, before taking the deepest breathe I've ever taken and closing my eyes and then slipping the dress on, feeling the femininity of it wash over me as it slid down my smooth skin, like a slow-moving waterfall of wonderful, the material divine, a precious cool against my excited hot skin, the wrap-around shape of it holding me in a grip of sensual pleasure.

Two seconds later I had to grab my penis, as rigid as a short stubby iron bar, using all my strength to avert a total disaster, an explosion of majestic size averted at the entirely last second, keeping me from the ultimate embarrassment of staining the most beautiful gift I'd ever received before I could even show it to the man who'd bought it for me.

I realized that it was the only beautiful gift I'd ever received.

And this one from a man! What a turn of events!

A man who I knew to be gay, after spending his life pretending to be straight, a man who was older than me and had impressed me from our first meeting with his respect and his charm and his gentle looks and demeanor.

My nipples got rock-hard in my bra, to match my penis in my panties, and despite not having any experience and the firestorm of nerves that come along with that, I was burbling with the need to show him how I looked, and how I felt, and how much I wanted to be this new me exclusively for him.

For just a second or two I thought about the joy I'd have telling Leslie what I was going through and what I presumed was going to happen, and how I was sure she'd be pleased as punch, giving myself the mental task of remembering every little detail, even if nothing came of it except some conversation, so she got the whole story.

Perry had his back to me as my heels made thud noises in the carpeting of his suite, and he turned slowly, and I watched his eyes meet mine, and then head south.

Slowly, he gazed at every part of me, as if he was visually devouring me, lingering more on my chest and then my groin, where my excitement was more than obvious, but spending a lot of time on my legs as well, the stockings making them as sexy and feminine a sight as there was in this world.

I was a man. It was obvious and there was no getting around it. Nobody on the planet was going to be fooled, or somehow get the impression that I was maybe just a slightly-masculine female.

Perry wasn't staring at a real woman.

But I was a man who was now swimming entirely in the feminine end of the gigantic pool of life, which meant Perry was staring at my version of womanly, my personal rendition of girly, and not just on the outside.

This wasn't a costume party.

I was allowing the softness and sensuality of the clothing to literally seep into every cell of my flesh, infusing me with their sensibilities and sensitivities, and for the first time in my life I felt complete.

I felt desirable.

I felt attractive.

I felt proud.

I was proud of me, regardless of Perry's reaction.

I suddenly realized I was doing it, right that second. I was doing it!

I was living the power of the feminine that I'd admired more than everything for my entire life. I could see my power, reflected in his eyes, and the lump that appeared in his trousers.

Finally looking back up to my eyes, he smiled.

"Champagne?" he asked, pointing to a bottle and two glasses.

I couldn't nod fast enough.

Once poured, he held up his glass, offering to clink it with mine, in a toast.

"To new beginnings," he said, and I realized it was possible that he wasn't just referring to me. He himself was newly into his honest and true sexuality, just barely eight months after the death of his wife and mother of his children, and I realized that I actually didn't know if he'd acted yet on his life-long gay feelings or not.

Was I to be his first as well?

That is, presuming anything happens at all, I realized. Perhaps he had no interest in those kinds of things, I considered. Maybe he just wants feminine company, which of course would thrill me and not leave me disappointed in the least. Or perhaps we might cuddle, or kiss, maybe, or do some petting? It was, after all, a first date, and there was always the chance that he wouldn't want to go too far too quickly, like many people acted on first dates. Maybe he didn't want to rush into anything.

Maybe he was just a nice man who'd spent a small fortune on a dress for me, just to be kind.

Maybe I was just being presumptuous.

Except that one more look into his eyes let me know that I wasn't.

Perry pointed to the balcony, and asked, "would you like to talk outside and enjoy the ocean view?"

I took a quick gaze through the sliding glass door, for just a second, and could see that there were waist-high walls separating his balcony from the ones on either side, but that anyone in those adjoining suites who might be outside would definitely be able to see me, this new me, this feminine me, in a sexy dress and lingerie and heels.

A man, dressed like a woman certainly, wearing a woman's clothes, but without makeup or wig or anything to hide the fact that I was indeed a male.

The old me would have balked at the idea of taking the risk of being seen this way, probably turning tail and hoofing it away as fast as I could.

I placed my free hand in Perry's palm, as he gently guided me over the sill and into a slight breeze, the moon high off to our left and casting it's light down across us, and we stood at the railings, and clinked our glasses together, silently, smiles on our faces.

"You look beautiful, Justin," he eventually said, quietly, "truly beautiful."

I felt my cheeks flush with red.

"Thank you. I feel beautiful, which is a totally new experience for me."

"That gown seems to suit you," he continued, "from my perspective. You look, well, you look radiant. You're practically glowing."

I looked at him with dreamy eyes.

"I feel radiant," I said, honestly, "I feel, I don't know, I feel alive. I feel, like, this is the first time in my life when I've actually been alive. It's as if the last thirty-three years of my life were nothing, that I barely qualified as existing, and it always felt, I don't know, wrong, somehow. But ever since I won that gift card and Leslie talked me into trying women's clothes, I've finally felt alive! And now, with this beautiful dress," and I turned to face him, "this most lovely gift from you," and I stood on my tip-toes and put my face close to his, "now I feel like I'm almost complete, like I'm this close to being perfectly right, in every way."

Even in the evening dark, I could see him blush, just a little.

"It was nothing," he said, trying to be gallant and off-handed.

"No! You're wrong, Perry," I replied, "it's everything to me. Your generosity has allowed me to see my future, a life to be lived in this feminine way. And no matter how long I live, I'll forever be like this, dressed like this, and feeling inside the way I do right now. And for that, I don't know how I could ever repay you."

I could feel his breathe on my face.

My eyes told him what I was going to do, and his eyes told me he was more than fine with it.

Closing the gap between our heads, I did something I'd never done before and had never even contemplated in the realm of possibilities before.

I kissed another man.

On his lips.

They were warm, and soft, and pillowy.

I held it for second after second, my eyes closed, squeaking one lid open enough for just a quick peek, to see that his eyes were shut as well.

Perry snaked his free hand slowly and softly around my lower back, resting just above my buttocks, and with a gentle welcome pull our bodies met, just barely softly touching, while my free hand slid up his chest and neck and up around to the back of his head, snaking my fingers through his hair.

When, after minute after minute of soft kisses started to get more intense, I felt him part his lips, and the tip of his tongue tapped on my lower lip once and then twice, it was the most natural thing in the world to open my lips, and let him inside.

It was the most natural and needed thing in the world to let him take me, to let him lead. In my rare moments of love-making with women, I'd always felt a pressure to be the captain of the ship, to steer the course, to move things along, even though I really didn't ever know what I was doing, always failing to succeed with much of anything.

The sad-sack.

But with Perry holding me, the obvious masculine of the two of us, it just seemed perfectly right and natural to let him lead, to throw off that burden and emotional weight of being 'the man' and instead be guided, a natural less-aggressive gentle acquiescence, perhaps in some ways submissive to his strength and his will.

I could be what I truly was.

The feminine one. The counterpart, equal and yet different. The night to his day, the black to his white, the yin to his yang.

We caressed each other, his hand slightly stronger and firmer than mine, as we slowly and sensuously progressed to all-out tongue-kissing, swapping spit playfully, neither of us holding anything back, two souls in an endless universe, with nothing but time and nothing but lust as our energy.

He broke the kiss, after I don't know how long, and I was breathless and panting, as he was, and I could feel his erection pressed up against me, as he could feel mine, his thicker and longer than mine, and after squeezing my right buttock long and hard, he stepped back and held my hand and he escorted me back into the suite.

We left our half-drunken glasses of champagne on the coffee table.

We stood by the foot of the bed, and his hands came up to cradle my face, his eyes barely a few inches from mine.

"Are you sure, Justin?"

I nodded. A lot. Quickly. Which, I realized, perhaps made me look unnerved, or reticent.

"I'm just nervous, that's all. You know I've never done this," I admitted, "so I'm nervous about what to do, because I don't know."

Perry smiled at me warmly.

"I've only done this a few times, just to be clear, and all of them after my wife passed, so I'm not exactly an expert," he whispered, "but I promise you you don't have to be nervous."

"I'm trying not to be."

Just before his lips met mine again, he whispered to me, something that I later realized was profound.

"You already know what to do. As little or as much as you want, of course. And all of it will be easy, because it will be your natural feelings coming out. You'll act from your heart, and not your brain. No thinking, just being. You'll feel it. It's inside of you."

Standing with the mattress behind my knees, we made out again, this time with nothing in our hands except each other. With no rush, he explored my body and I explored his, touching and caressing and rubbing and stimulating.

He found my left nipple, even through the dress and the bra, and began twisting it, ever so slightly, a whole fusillade of fireworks going off inside me, and I moaned into his mouth, so he moaned back, a prideful one, letting me know he was happy as hell to be making me feel so good, so I slid my right hand from his back and around and teasingly down his belly and onto his groin, rubbing my palm down the length of his cock, which was standing up straight and tall and felt warm, even through his pants and underwear, and he moaned into my mouth, so I moaned back my reply, satisfaction dripping with the promise of more.

I WAS TOUCHING ANOTHER MAN'S ERECTION!

I don't know if it was my subconscious brain working or whether I was so overcome with elation that I couldn't stand up anymore, but either way I broke our kiss by sitting down on the mattress, with a plop, my head now about belly high to him, so I gazed up as my trembling fingers began unzipping his pants, my eagerness overcoming my inexperience, and he helped me along by unbuckling his belt and snap, the two of us staring at each other and listening to his pants hit the floor.

His boxer briefs soon followed.

As he undid his button-up shirt, I couldn't keep looking into his eyes.

I had to see it.

I had to take all the visual aspects in.

I had to commit to memory every detail.

Length, thickness, skin color, hair, the thick pinkish bag with two oval lumps hanging down.

I had to memorize each square cell of his erection.

I was going to take it into my body, so I needed to absorb in my brain every last spec, so I could picture that part of him exactly as it was when it was inside of me.

His cock was a nice size, bigger than mine, but not porn star big. It was maybe seven inches long, maybe slightly less, and had a slight bend to it, to his left and my right, and he was circumcised. An almost-purple helmet sat atop his shaft, flared and curved and rounded, similar to mine but yet somehow much more majestic, much more impressive. There were four bluish veins running haphazardly up his length, and one thick tube running up the underside.

The bulbous head was shiny wet.

Instantly, my mouth watered, a huge pool, and I almost swallowed it all, but at the last second some inner natural piece of gray matter in my head told me that I was going to need it very very soon.

I had to have his cock in my mouth. I had to taste his juice. Something inside me demanded it. Something in my genetic structure was leading me, and there was no room for compromise, no possibility of negotiation or backtracking. I wouldn't be a whole person, I wouldn't be complete, without my taste buds getting to feast on his pre-cum.

The new feminine me, I realized, right then and there, was stronger and more powerful than the old masculine me.

When I touched the tip of my tongue to him, he groaned out a long slow sound, and the tang of his syrup went 'KABOOM!' in my mouth, so I swallowed his entire helmet between my lips, like taking a huge apple or plum in whole, feeling his expanse, squeezed between my tongue and the roof of my mouth, the biggest piece of meat I'd ever tried to eat, and some uncontrolled mechanism in my brain went to work and commanded me to start getting it wet, working it with my tongue back and forth on the underside to make it easier to slide into my throat.

This meat, however, wouldn't make it to my stomach, that much I knew.

But his cum would.

As if I'd been doing it forever, as if it was my God-given talent and my most natural ability, I began sucking his cock, hungrily, with no fear or shame, all my inhibitions gone, slowly grabbing and releasing him with my mouth, further and further down his throbbing shaft, making squishy sounds and frantic gasps that rocked through my cranium and seemed to fill the room and drown out the sounds of the engines and the waves hitting the ship outside the open sliding door, and Perry put his hands gently on my shoulders, and sighed out my name.

J-u-s-t-i-n.

He purred it out.

Like a bolt of lightning, I took his cock out of my mouth, and gasped up at him.

"I've always loved the name Katrina."

Perry smiled down at me.

"Katrina."

I smiled up at him, but only for a second, because the next second his cock was back in my mouth, and I closed my eyes and lost myself in the moment, sucking and licking as my mood took me, proving him right when he'd earlier said I'd know what to do because the knowledge was inside me.

It was profound.

Perhaps, I thought, it came naturally to me because I had one of those penises myself, even if mine was shorter and thinner and uncircumcised. It seemed a logical premise to explain why I was succeeding, so obvious to both of us, just based on the noises we were making, his moans and mine mixing in harmony like an orchestra playing the most erotic classical piece ever composed.

Or maybe, it occurred to me as my mouth was savoring his constant flow of pre-cum, slightly oily and slightly salty, that my thirty-three years of presumed heterosexuality was all a total fraud, an innocent mistake, a colossal waste of my time, a diversion, because as unsuccessful as I'd been with women in romance and sex, this was the exact opposite!

Being my first time, my lips began to feel just a little bit sore after only a couple of minutes, unused to this kind of a work-out, but that didn't stop me from sucking him, it wouldn't deter me from what my soul wanted, it couldn't have cut short my first fellatio, the first one in what I instantly knew would be a lifetime of giving oral sex to men, the thought of not ever again having a living breathing pulsing rod of masculine meat in my mouth simply ridiculous to even consider.

I knew it from that exact moment.

I would be sucking cock forever.

My winning streak seemed to keep going, because as my lips got sorer, Perry's groin started rocking a little bit, in and out and in and out, respectful but insistent, letting me know he was close, so I just amped up my efforts, despite the slight discomfort, because as much as I was loving having his cock in my mouth, the thought of finishing him, of getting my reward, the wonderful bounty of his seed, it became an all-consuming need.

A minute later, if that, he growled out something unintelligible, like a beast in the forest, and instantly my mouth began filling with a salty liquid that was thick in parts and runny in parts and other-worldly delicious to the last drop!

AND THERE WAS S-O-O MUCH OF IT!

None of the three women who had sucked my cock had ever swallowed my cum. They all spat it out, making noises to show me that they were offended in some way or other, as if it was a burden they didn't want to assume.

I felt sorry for them, there in that moment.

They had no idea of the abject spiritual nirvana of literally taking a man's essence into their bodies, his seed, the very life-giving power of a man's ejaculation swallowed and to be used as fuel, like the richest most potent food in the universe.

Perry's load was so prodigious that I had to swallow in three huge gulps, never allowing even one single drop to escape my lips, letting his cock go at the very last second so I could tilt my head up, crane my neck, stare him in the eyes, show him the last pool of his white cum in my mouth, before swallowing it down in one long delightful gulp, and finally smacking my lips and beaming.

"MMMMMM!"

His legs were shaking, just a little, as if I'd almost sucked the energy needed to stand up right out of him, through his cock.

AND NOW I KNEW WHAT IT FELT LIKE!

THE POWER OF FEMININITY!

I WANTED TO LIVE IT, EVERY SECOND OF EVERY DAY!

FOREVER!

It took him more than a few seconds to re-establish his connection with reality, so I nuzzled his hairy balls with my nose and kissed his inner thighs and softly caressed his belly with my hands, keeping my eyes on his, waiting him out, because I knew what he was going through, having had my own debilitating orgasms lately.

When his body stood back to attention, he snapped his eyes open, a look of enormous seriousness covering his face, and with determination he threw off his glasses, missing the soft landing of the love seat, instead hitting the floor, but luckily not breaking, and reached down and pulled me up, back on my feet, and his mouth descended on mine and his tongue forced it's way inside me, and our arms wrapped around each other and we hugged hard, crushing ourselves into the other, a brief flicker of amazement crossing my lust-drunken mind that I could feel him against my belly and he was already getting hard again!

THE POWER OF FEMININITY!

I was making him hard again, just by what I was wearing and the accompanying change in my life-force, all the attributes of femininity washing through me, coloring my emotions and my behaviors.

There was a female in me, taking over, pushing the masculine away, in how I acted and reacted and how I thought and how I operated, at the most basic and intrinsic levels.

I am now Katrina!

His kiss was strong, and left no doubt about how he was feeling. The masculinity in him was raging for the next act in the play.

Like the mightiest lion in the jungle Perry was in heat, his inner driving force guiding him to his natural position, on top of a woman, and he was going to sate himself, by mounting his lioness.

Me.

"Let's get this dress off you," he breathed out, after he broke our kiss, so I reached down and pulled it from the bottom up and over my head, his eyes going as wide as dinner plates at the sight of me in my bra and panties and garter belt and stockings, and my golden high heels.

"My god," he whispered, admiring me, before his mouth came back down on mine in an inspired flash, arms clutching around my body, before he just fell forward, making me go backward, and we landed on the mattress, his weight on me, crushing me into the softness, my arms around his back and my legs wrapping themselves to his rear end, my ankles locking together, subconsciously telling us both that I wouldn't let him go anywhere even if he wanted to, and our kiss was off-the-charts fervent and spirited.

We were furious and there was nothing holding either of us back.

The innate animalistic passion that seems to reside in all men rose to the surface and exploded outward, for both of us, and juxtaposed with my new-found femininity created a kind of double-headed creature inside of me, the softness equal to the testosterone, the always-horny male and the soft giving female as partners, no inhibitions present, like there always seemed to be for me when I'd been intimate with women.

His hips started grinding his cock against my body, back to full erection, every few strokes with a firmness that rubbed up against my trembling hard-on and brought me to the edge of explosion, the tics and tremors I'd been feeling for weeks now gone, replaced by tsunamis and earthquakes, a life-time of sexual disappointment now destroyed, gone forever and forgotten, say goodbye, the eternal joys of heaven now merely one simple step away.

I slid my lips off of his and breathlessly gasped the solitary thought resonating through my soul.

"PLEASE BE INSIDE ME! PLEASE, PERRY!"

His right arm shot out to the bedside table, and we went back to kissing while I heard the sounds of something clicking, like the top of a jar or a squeeze-tube, and then the next thing I knew a wet slick oily finger slid between my bum cheeks and stabbed right at my hole, meeting no resistance at all and sliding in to the second knuckle.

The scream that came out of my lungs would have been noticeable by the people two decks above and below if it wasn't for the fact that his mouth was totally covering mine, so the sound got muffled and quickly deadened, but it made him grunt in a kind of smug satisfaction before the finger slipped out of me and there was another faint wet squelching sound and then two thick slick fingers found my hole and rammed in, all the way, my insides stretching and squirming and shaking, a few nerve endings raising objections but the rest registering nothing but the strangest and most welcome pressure.

Adding to the life-affirming amazement of everything else I was going through, I was surprised to discover that I wasn't fighting the intrusion. I'd expected anything connected to my anus would be painful, because I'd never done anything like that before or even considered it as a possibility. I was, after all, not gay, for all those years. So I assumed there would be resistance to anything that tried to breach that forbidden territory.

And yet I was taking his long thin digits in with absolutely no hesitation, with no pushback, which I realized was just more proof that not only did I want him inside my most sacred opening, but I needed him there.

I was born for him to be there.

Two more squishy sounds and insertions later, I heard a final extended squelch, and then instead of being pierced by fingers I heard some slick sibilant rubbing sounds, which even through the heaven of his kiss made me realize he was making his cock wet, and I knew instinctively what happened next.

THIS IS IT!

I'M ABOUT TO HAVE GAY SEX!

WILLINGLY!

A MAN IS ABOUT TO SPREAD ME OPEN AND ENTER ME WITH HIS COCK, LIKE MEN HAVE BEEN DOING TO WOMEN SINCE FOREVER!

HE'S GOING TO FILL ME WITH HIS FLESH!

MY LIFETIME OF FAILED MASCULINITY WILL DISAPPEAR IN A MICROSECOND, TO BE FORGOTTEN IN THE RUBBLE OF HISTORY, AND INSTEAD OF BEING THE ONE INSERTING INTO SOMEONE ELSE, INSTEAD OF BEING THE MAN, THE PENETRATOR, THE TOP, NOW I WOULD BE THE ONE TAKING THE INSERTION, NOW I'D BE THE PENETRATED, THE BOTTOM, THE TARGET OF A MAN'S LUST, JUST THE WAY THAT NATURE WANTED FOR ME, BUT FOR SOME REASON HAD NEVER TOLD ME ABOUT!

It's amazing, how in the space of a second or two at most there can be literally hundreds, if not thousands of thoughts go through your mind.

Sad-sack. No luck except bad luck. Horrible acne and failures with women. Years and years, decades of loneliness. Dead-end jobs. Crappy apartment. No prospects.

But then.

A sudden shift of fortune. Winning tickets. Rose Wind. Leslie. The power of the feminine. Unimagined sensual discoveries, of soft and silk and sexual satisfactions. Exotic locales. Perry. The staggering desires of the masculine running headlong like a runaway train hurtling straight at me. Living the feminine part of me, discovered and set free, true happiness finally coming to fruition.

When the tip of him wedged into the concave entrance to my body, teasingly touching my winking hole, Perry stopped the kiss, separating our mouths, and his eyes opened up to see mine opening, our foreheads touching, and he wordlessly told me that nothing was going to stop our joining, even if the third world war started or our own sun suddenly went supernova and we were about to be blown out of the sky and destroyed as a planet.

I wordlessly told him there was nothing I wanted more than him taking me.

With one final moment to silently allow me to change my mind, an impressive last second control of his obvious yearnings, yet sensing no retreat was wanted, he tucked his chin in and his head quickly bent and ducked and the next thing I knew his teeth had found my left nipple, hard and swollen and nubbly, even through the lace cup of the bra, and he bit down on me!

My back arched upward in reaction, my body's natural attempt at throwing off the sharp pain actually failing spectacularly, the result of my reaction being pushing my nipple even further into his chomp, and I yelped out a lung-clearing high-pitched squeal that his neighbors couldn't NOT have heard, even through thick bulkheads. and he used that moment of my mind's distraction to rock his hips in one lunge, and his entire erection slid into me, in a staggering and monumental push, until his pelvis thumped into mine, rocking the both of us.

There are millions, if not billions, of nerve endings in our bodies.

Every single one of them inside me exploded in one cataclysmic eruption.

"NOOOOOO!" I screamed, at the top of my lungs, raging pain and discomfort rocketing from my ass all the way up to my cranium, tens of thousands of little white stars suddenly appearing in my vision, exactly like the one and only time in my life I'd ever suffered a concussion, when I walked around a corner at work and accidentally hit an open door at full speed with my forehead, winning me a ride in an ambulance and an unpaid week off.

But this hit was nowhere near my face.

Perry's body froze on me, the echo of my scream still bouncing around his suite, and he must have instantly assumed that he was hurting me, or that I'd changed my mind now that I was actually finding out about the consequences of being entered, and being the kind and considerate man he was, someone who didn't want to cause me pain, he began to pull out of me, almost all the way, and suddenly all the stress and strain and shocking discomfort and actual pain inside me changed dramatically.

His withdrawal was allowing the flesh inside me to go back to their natural shape, their normal configuration, and that slide felt foreign, new to me, but breathtakingly beautiful, as if I was suffering the most delicious kind of agony, so I screamed again.

"NOOOO! DON'T STOP!"

Perry's head came down beside mine, so his mouth was right next to my ear.

"I'm hurting you," he grunted, genuine heartfelt worry in his voice.

"DON'T STOP! KEEP DOING IT! KEEP DOING ME!"

He lifted his head, and I stared at him through my watery eyes.

"But I'm hurting you," he said again.

My interlocked ankles let me pull at his body with my legs.

A tear ran out of both of my eyes, simultaneously, and headed down my cheeks towards the mattress.

"IT'S THE BEST KIND OF HURT I'VE EVER HAD!"

It was.

He gave me a look, like, 'are you sure?'

"DO ME! DO ME! I LOVE THE HURT!"

I did.

Shoving himself back in, fully, but with tenderness, shaking my whole body and rattling my bones, the hurt reared up again, and I grimaced, gritting my teeth, but just before my self-preservation response kicked in where I'd scream out for him to stop, pushing him from the inside and outside to get out of me, like heavenly magic that hurt suddenly changed into the most amazingly pleasurable fullness, an overwhelming intensity of pressure inside me, unlike any other feeling in the world, a million billion on a scale of one to ten in raw physical exertion, the seriously most strenuous ordeal, and for the first time in my life something that just felt right.

THIS IS IT!

THIS IS HOW SEX SHOULD FEEL!

I was a winner.

"MORE!" I cried out, and Perry moved his head and bit my nipple again, and I screamed out it out again.

"M-O-R-E!"

He pulled out slowly, letting me revel in the cycle of difficult into delightful, before grunting in my ear and pushing hard, lunging into my guts, making the backs of my thighs ripple and the breathe get forced out of my lungs.

I was gone.

The thinking part of my brain switched off.

There was only feeling.

There was only the riding of waves, like lying on your back in the ocean.

I had no control, over anything, not my body or my mind.

I was a very willing participant in an arduous journey, just along for the ride, absorbing the tumultuous shocks to my skeleton with every thrust into me, the absolute no-question without a doubt hardest physical activity I'd ever done, and coming to the realization that I didn't want it to ever end.

By ceding all my critical and analytical mind and just being in the moment, living for only what I was going through and nothing else, I was finally free.

Free.

Free to soar on these wild winds I'd sailed into.

Free to fly, in a part of the sky few others ever aspire to.

Free to glide on that razors edge between pain and pleasure, and how they each make the other insanely better.

Perry began slowly picking up the speed of his thrusts, and my back arched every time, without me thinking about it, as if my ass and insides knew what they wanted and were making the decisions for me, gripping at his cock to get it back inside me again and again, doubling the impact when he pushed inside and quadrupling the sweet agony.

For minute after minute, I bounced between grimaces and grins, between pain and pleasure, as we banged our bodies together, my arms around him pulling at him harder and harder, and every time he thudded into me he'd let out a grunt, his animalistic lusts similar to mine, surrendered to them, in the moment.

No rules.

Just lust, and passion, and strenuous physical exertion.

The best things in life are free.

At one point, whether he meant to or not, Perry changed the angle of his thrust, perhaps moving his pelvis slightly differently, and as his cock slipped through my fibrous channel askew he rubbed against something inside of me, and the insertion felt like a slow-motion red-hot flame-thrower, which started a fire amongst all of my insides, and every muscle and tendon and ligament in my body seized in one giant lurch, as I launched into an enormous orgasm, out of control, gigantic lunges of my wet cum rocketing out of me, my glazed eyes seeing nothing but white stars.

The sweet birth of the feminine me made me the luckiest man alive.

After pausing for a few brief moments while I thrashed around under him Perry went back to pounding me, spending his lust in me and on me and through me, he himself without thought or control, just feelings, the preternatural need to rut so primal and buried in us all, with only some of us actually tapping into it.

Those of us who are free.

I lived, I rode, I followed, I moved with him, I went with the flow.

I predicted nothing and therefore everything was vibrant and new, the way love-making should be.

I was lost in the ether, higher than a kite could ever dream of rising to. We banged and bucked and rocked and slammed and it just kept getting faster and faster, shaking my whole body like I was being brutally pummelled, which in some ways I was, realizing again that I WANTED it, until Perry bit down on my earlobe, a strong nibble, and I gasped and he gasped and then he rammed into me one more time, harder and stronger and more fierce than all the others, his whole body frozen in place, my hips and pelvis absorbing the shock one last strenuous time, a pile-drive slamming us further into the mattress, and he came inside me in long slow spurts.

He came so hard and for so long that he completely collapsed on me, whatever weight he'd been carrying with his knees and his elbows suddenly gone, spent, exhausted, and I oomphed out all my air and realized that I was crying, almost to the point of sobbing, the stillness of his cock inside me making me stuffed, almost to the point of not wanting it, and yet not wanting it to ever go away.

And just like the feminine creature I'd become, I held him to me, as I imagined a loving woman would, caressing him, murmuring little moans to him as I came down from the heavens, the rigors over, thanking him through my gentle touch for the huge unparalleled gift he'd given to me, the act of love-making he'd bestowed to me that had not just pleased me, but freed me, heart and soul.

We slept together in his bed, all night long. We were both wiped.

During the night I roused in that minor way people do a few times in the darkness, at first surprise registering at being in a strange room, but then pure and utter joy and gratitude flooding my senses at what had happened, and every time, no matter what position I'd been sleeping in, I was over-the-moon happy to see I was always connected to him, wrapped in his arms!

And I was always holding his penis, cradling it lovingly in my palm.

Perry got to wake up in what I imagine is the single best way possible for him, with a feminine man wearing lingerie sucking his cock back to rigidity, and when I finally opened my eyes and realized he'd opened his, and was aware of what I was doing, I took him out of my wet mouth and, after saying the sweetest "good morning" to him, which he softly returned, I asked him if he wouldn't mind making love to me again.

"K-a-t-r-i-n-a," he said, "I can't think of a better way to start the day."

He said my name slowly.

He almost purred it.

With nature guiding us, once again I was wrapped in a man's arms, and buried under his protective body, in the missionary position, nose-to-nose, panties and heels off, legs spread and wrapped around his behind, as he slowly slid himself into my body again, his shaft once again lubed and making my channel wet with every forward motion, and the intensity and pressure and physical exertions returned, to the extreme.

Like an old friend, I welcomed every staggering strenuous second, every difficult dimension, every burning burst inside me, because the trailing ecstasy that always followed made those moments of hardship disappear, rendering those difficult parts as meaningless, just a necessary evil in order to get to the good stuff.

Making love like this wasn't a hardship.

Getting slammed one thrust after the other made my teeth gnash and my skin shudder and my flesh strain, inside and out, as if I was in a life or death battle, in fierce body-to-body combat, except in this kind of war there were no losers.

Both sides got to declare victory!

Making love as Katrina, the feminine man that had lurked inside me forever and finally bloomed, wasn't any kind of a burden, or a hardship.

It was as natural and welcomed as breathing!

Perry had an excursion booked in our little Mexican town, and he offered to pay for me to join him, but I was, in the best of ways, exhausted, so I gave him a gentle kiss and made my way back to my stateroom, sadly once again in boy clothes.

My walk was purposeful, and proud. Any of the other passengers or staff who saw me would have known, on some primal level, just from the look on my face, that I was a sexually-satisfied human being, that I was tripping on the afterglow of having had the best sexual night of my life.

They also would have seen my erection, which was steely and barely-contained in my panties and poking an obvious tent into my trousers.

A walk of shame?

HAH!

Mine was a walk of soaring contentment.

But I was exhausted.

Parts of me were sore. Parts of me had been put under enormous stress, and they were letting me know. My legs, particularly my thighs and my buttocks, felt like I'd run a marathon, which I'd never actually done but I knew had to be a kind of torture, my exertion and exhaustion joyfully not from running, but from being spread for so long and bent backwards towards my body for so long.

My legs had gone through the best work-out in the natural world.

These were the kinds of sore I'd gladly go through every day, if it meant Katrina got to be alive.

I spent a couple of hours up on the pool deck, laying on a lounge chair, watching people and soaking up sun, and having two Pina Coladas, since I'd only had one the night before and I could afford it. The whole time, through the wafting and competing voices of dozens, if not hundreds of people, including the passers-by, the laughter and the boisterous talk and the occasional giddy gleeful eeks of women in the pool, I played the mental memory tape of the night before over and over and over again, on a loop, my smile as big as the erection I had in my swimsuit, the red woman's suit that Leslie had sold me, not caring one bit that people could see it, if they looked my way.

I had to stop myself from shouting out how I felt, at the top of my lungs, for everyone on board.

I GOT LAID LAST NIGHT!

I HAD GAY SEX!

I TOOK A MAN'S COCK INSIDE ME!

FINALLY, AFTER THIRTY-THREE YEARS, KATRINA IS ALIVE!

A bunch of times I thought about getting up and walking around, or going for a swim, or just moving on deck, letting people see me in my tiny swimsuit with my smooth skin and my obvious erection, because my soul was full of raging energy, the furnace glowing red-hot inside me, fed on burning lust and memories of Katrina's first night, and first sex.

Katrina's first man, inside her, taking her, using her as his outlet of passion, the target of his power, battering her body with his lust like a boxer does to a punching bag, and, most amazingly, her displaying her own power, her feminine power, loving every rigorous second of it, giving back to him, using his manhood to get to her own paradise.

Back in my stateroom I dozed for a couple of hours in the afternoon, before washing and shaving my whole body in the cramped shower, and made it to dinner just on time, in my boring man clothes on the outside, the bubbling cauldron of femininity inside being temporarily satisfied by the thong panties and thigh-high stockings I had on underneath.

Everyone at the table talked about their day, and what they did in port, and I listened half-heartedly, most of my concentration on replaying every sensory memory of Katrina's love life, now numbering two incredible screwings.

The travel agent lady asked me how my day was, and I happily told her I'd spent the day on the ship, relaxing, never even getting off the boat, which, based on her look, she found odd, but then she shrugged it off and started talking about the next day, when we would be in San Diego, and all the things to do there, and I nodded like I agreed to the idea of going to those places and doing those things, but I couldn't afford them, so I was already planning on just walking around the part of the city closest to where we were docked.

After dinner, I waited in the foyer outside the dining hall for Perry, and everything inside me leapt in joy when I finally caught his eye as he made his way out through the crowd, and he grinned, warmly, so we walked up the giant staircase two floors and found an outside deck to stroll on and take in the fresh sea air and the beautiful sunset off to the west.

"How are you?" he asked, and I knew he meant more than just the standard common courtesy.

"I'm great," I said, hurriedly, "I'm so great. I've never been this great, I've never felt so, well, so completely wonderful."

He nodded his agreement.

"Me too. It was a very special night, wasn't it?"

His voice was quiet, and reverential.

"Thank you," I whispered.

"No," he replied, "it's me who must thank you, for the pleasure of your beautiful company, and giving this old man the most memorable night he can remember."

Walking abreast, I stepped closer to his right side, casually, so our bodies could touch.

"You're not old," I said, in a slightly scoffing way, "old isn't an age, it's an attitude. It's a mindset. And," I paused, "just based on what happened last night, and then again this morning, there's no way I would ever think of you as old."

He smiled, delighted.

"No?"

I shook my head, playfully.

"Uh-uh," I giggled, "the way you acted, the way you took me, the way you pounded me, that wasn't how an old guy acts. That's how a vigorous man acts, with the fury of youth."

I watched concern flow slowly onto his face.

"Was it too much? Did I hurt you?"

I stopped, so he stopped, and we waited for a few other people to slowly walk by us.

"No, and no."

His good nature and care made him want to make sure, but before he could ask I gave him the look.

"I wouldn't change a single moment," I breathed out, "not one. Both times, last night and this morning, as tough as it is, as much raw work as it is for me, they were the greatest points of my life, bar none, no question, nothing else even comes close, and I'm going to be eternally grateful and thankful to you, for helping Katrina be finally born."

I could feel my eyes getting wet.

Perry stared at me and his eyes behind his glasses got a little wet as well.

"So what happens now?" he asked, tentatively.

I didn't have to consider my words.

"Well, unless you have something else planned for the evening, what happens now is you go back to your stateroom and get ready for your second date with Katrina."

Then I looked at him, nothing but honesty on my face.

"If that's something you'd enjoy doing again."

The old me would have lost, and Perry would have said no, he had better ways to spend his time, or a specific other person he wanted to be with, or something to do.

Justin would have gone home empty-handed, and empty inside.

Perry took a deep breath, and blew it out.

"How soon can you be there?"

We stood on the balcony, watching the ocean zip by and feeling the wind through our hair, and talked for a couple of hours, about our lives and experiences. We told stories of things that had happened to us, him more than me since he'd lived longer and had more events to relate, and on the face of it we were simply two adult men learning about each other, new friends becoming buds, the way men have bonded since time immemorial.

Two men.

Two men, but only one who was masculine looking and acting. There was only one who looked like a man.

The other man, me, was the exact opposite, in both demeanour and dress.

The gorgeous dress he'd bought for me.

And unlike when most men get together, we kissed, from time to time. Soft sweet pecks, and longer lingering lip massages. The both of us seemed perfectly happy to not rush into bed, thoroughly enjoying each other's company.

Eventually, though, the ardor rose in the both of us, coming to a slow boil, until the desires grew enough to overpower the friendship we'd established, and I walked him to the bed, in just panties and thigh-highs, shedding my bra after the dress hit the floor because I wanted him to have open and free access to my nipples, which had surprisingly become two major erogenous zones in my life, and I lay down on my back and shuffled up so my head was on a pillow at the headboard and I gazed at him dreamily.

"Make love to me," I breathed out.

Perry shook his head a little.

"Make love with you," he corrected, saying the word slowly.

W-i-t-h.

He almost purred it.

And yes, of course, I realized he was right.

It was a partnership.

This battle took two competitors, the both of us giving as hard as we get, free of restraints, no rules, just pure brain-switched-off exertion, letting our natural energies and desires guide us.

Perry started slowly, just the way I like it, allowing me time to get used to him again, buried inside me, the cycle of our joining beginning anew, discomfort to delight, winces to wriggling, perilous to perfection.

Between sorrowful grunts and frantic yelps and hard wild kisses I kept murmuring words, 'more!' and 'harder!' and 'YES!', Perry obeying my every demand, sweat building on the skin of his face and his upper back and shoulders the further we got into it, the more and more pounding we were giving each other, shaking the whole bed, and rattling me inside and out, the top of my head banging into the headboard with each slam of his cock into my ass, the full weight of his pelvis hurtling forward with every thrust, a constant stream of tears running out of my eyes, and I'm sure, to any prospective passers-by, looking like someone who was being assaulted and wanted it to stop, but they'd be wrong.

I never wanted it to stop. The agony or the ecstasy.

Just like the night before, at one point he perhaps inadvertently changed the angle of his thrust and his shaft rubbed up against something in my depths that burned in intense flaring that sent a buzz-saw of vibrations through me, fast and furious, just a few rubs later sparking my gut-wrenching release, multiple lurches of cum spurting out of me, so fast and under such pressure that it made my penis hurt, my whole body seizing with every pulse, like Frankenstein's monster during the electrical storm.

And just like the night before, my explosion became Perry's motivator, and he switched into a higher gear and began truly slamming his cock into me, strokes that were brutal and hard and with fury, the gentle man suddenly a wild animal, just the way I wanted him to be, the way we all were, when the world was young, before we became civilized, when morals and values started being enforced.

We were two humans, locked together in the dance of wild passionate love, balls-out, with only one goal to be reached.

Total ecstasy.

Total physical and spiritual exhaustion and release.

The next morning we woke up in San Diego, and I accepted his offer to pay for me to go on the excursion bus to the zoo and Balboa Park.

And to thank him for his generosity, I sucked his cock like a demon possessed, just inside his stateroom door, and he gave me a quick mouthful of creamy semen, before we went to breakfast.

The world-famous zoo was spectacular, of course, and we could have spent several days there, but only having a few hours before we had to be back on the ship the two of us kept a brisk pace and saw a good portion of it before heading over to the many museums and attractions in the rest of the park.

It was the most comfortable day of my life.

We were two men, new friends, sharing the exploration of art and culture together, and anyone watching would have seen camaraderie and respect, just two guys wandering aisles and taking in the sights.

They would have seen two men gazing occasionally and enthusiastically at some of the women around us, those that seemed to dress up a little, the ones in skirts or dresses, the ones with makeup on and heels. There were more than a few of them, and while Perry's attraction was physical, mine was that PLUS emotional, because I wanted to wear what they were wearing, and live surrounded by that sensual softness every second of the day.

Anyone watching would have never guessed that we were also lovers.

They'd never have guessed we were two gay men, one masculine and one feminine, bonding on levels beyond simple acquaintanceship.

Several times during the day, seemingly innocently, Perry reminded me that tonight was the last night of the cruise, and that the disco was holding a celebration, a 'come-as-you-are-costume-ball', with music and prizes and guaranteed to be the highlight of the trip, at least according to the daily ship newsletter that gets slipped under your stateroom door while you sleep, and I'd smile at him, because I knew what he was inferring.

He was hoping I'd go as Katrina.

From the neck down, a feminine sight to behold.

From the neck up, an obvious man, so it fell under the category of costume.

But if I was going to actually be seen in public, I momentarily worried, shouldn't I try to finish the job and go fully as my impression of a woman? I began thinking about make-up, and a wig, knowing I had no way of getting them now, on the ship, at sea, but wondering if I wanted to add those things to my world, my new feminine world, and if they'd somehow make what was already earth-shattering glee get even bigger, and a part of me seemed interested.

But another part of my mind didn't, at least not for tonight.

That part said to me, no, you're not a full-on transvestite tonight, even if you wanted to be.

I was a man, and proud to be one, proud to be a feminine man, that's all, one who enjoyed the clothes and how they made me feel, how they made me shine, inside and out, bringing Katrina out of her shell, and as we were getting back onto the ship I turned to Perry and told him I'd love to go to the ball as me, as Katrina, and he could pick me up at my stateroom at exactly nine o'clock.

The formal dinner meant throwing on my suit jacket and tie and wearing my office shoes, but underneath I was of course adorned with lingerie.

Once I'd wolfed down dessert, I fairly ran to my stateroom, to get ready.

Drab and dreary man clothes off, I leapt onto my bed and rolled onto my back and began masturbating, something I'd been wanting to do all day, slicking my foreskin up and down and watching it curl over the wet head of my erection, seeing the pre-cum seep out before coating a fingertip and licking it clean, again and again.

A weird thought struck me.

How many other ways can a human give themselves some sort of pleasure AND get a tasty treat at the same time?

In the few minutes I had to wait for Perry, once ready, I stood by the bed, wearing my Rose Wind little black dress, hugging me like a second skin, especially my pushed-out rear end, thank you high-heels, and realized that I was, in fact, ready.

I was ready to walk out of this private room into the world, in front of other people, hundreds if not thousands of them, without embarrassment or shame or hesitation.

I was ready to hold the hand of another man, my date for the evening, as he escorts me to dancing and drinking and a crowd of partiers.

I was more than ready to let everyone know that I was a changed man, a new man, a feminine man, and yes, a sexual man, with other men.

I was ready to be who I am.

Katrina.

Lovely, and feminine, and gay.

At exactly nine o'clock, there were four raps on my door, and when I opened it I saw Perry's costume.

He was wearing silk pajamas, dark blue stripes on a light baby blue background, with slippers on his feet and a tobacco pipe clenched between his teeth.

"I'm Hugh Hefner," he boasted.

"Does that make me your bunny for the evening?" I asked, stepping out into the hall and closing my door before taking his offered arm and curling mine inside, like I saw my Mom do with my Dad for years.

Perry looked down and his face got serious.

"Katrina, you are the only bunny I could ever want, any evening."

I felt my heart almost stop, as I came to a halt, so Perry had to immediately stop, and I could see worry cross his face, that he'd said something wrong, or gone too far.

"I'm sorry," he stammered, "I didn't mean..."

I shushed him, and waved my free hand with the 'it's nothing' sign.

"I love being with you too, Perry, and I don't want it to end either."

Some of the worry came off his face.

"And," I added, "mister," pausing a bit, "if that's some sort of line you men give to your dates because you think it'll help you get some sex," and I paused again, before smiling, "then, let me tell you, it worked, because you are going to get the absolute best sex of your life tonight!"

He smiled at me.

"I'm not sure it could get better than last night," he whispered.

Pulling his arm to get us walking again, I grinned with satisfaction, hearing my lover say that love-making with me was so impactful on his life.

"But I'm not a cheap date," I said, "and you better have your card in those pajamas, because this lady wants a couple of drinks before she puts out!"

On our walk up the entertainment deck level, with me swaying my hips and strutting, we saw lots of people, and they saw us, with the whole gamut of reactions, from grins and smiles to wide-open eyes to gasps to startled sounds. And to my surprise, there were more than just a few people in actual costumes.

There were action heroes, and damsels, and cartoon characters, and pirates, and one guy dressed as Colonel Sanders. There were men, young and old, showing upper bodies, in shorts or tight pants but topless. There were women in next-to-nothing slinky fabrics, and two different Elvira's.

One of those women in next-to-nothing was the sexy woman from the airplane, and as she walked towards Perry and I, braless, her areolas and nipples visible under the sheer top she had on, we could see her gazing around, just randomly looking here and there, until she focussed on us and saw two faces she'd seen before, and you could almost hear the gears going as she searched her memory, taking a few seconds before things twigged, and she smiled as got close to us, and then she stopped.

"You guys were on the same plane as me, right?"

We both nodded.

"Where's your man friend?" I asked.

She looked slightly confused.

"Man friend?"

"Yeah, the guy you travelled with."

It took her a couple of seconds to think.

"Oh that's Sean," she said, "he's not my man friend, he's my brother. And he's around here somewhere," she said, looking left and then right in a circle, "probably trying to find a cock to suck."

Neither Perry nor I could contain our snorts of surprise, that someone would say that out loud, in public.

She looked at us, defensively.

"What? Like you two would be offended by that? Give me a break!" Then she pointed at Perry. "The way he's making googly-eyes at you," and then she moved her finger towards me, "and the way you're dressed? C'mon!"

Then she smiled, and it lit up the whole hallway.

The power of beauty.

Perry and I looked at each other and then nodded, so we nodded at her too, to admit she was right.

So she nodded proudly, like she'd just been the first person in the history of the world to say a basic truism known to all mankind.

"And you," she said, still pointing my way, "you need some makeup," and before I could say anything she'd grabbed me by the arm and pulled me down the hall to a bank of washrooms, in a hurry, her way more experienced in walking fast in heels than me, past three hand sanitizer stations, and then made me close my eyes while she brushed the lids and then open my eyes while she brushed the lashes and then make the kissey-face while she brushed my lips, and then she showed me in the mirror the results, and I had to use all my stomach muscles and abs to grab at things inside to stop the orgasm train which was barrelling down the tracks.

I had smokey eyes, with actual long thick lashes.

I had pink lips, dark almost to the point of purple, and they shone in the light, glistening, looking wet and luscious.

"I can't do anything with your hair," she said, casually, before throwing her tools back in her little clutch purse and opening the door to leave.

"Now you go have fun, do some drinking and some dancing, and then take your man back to your room and get laid," she said, grinning, "I'm gonna find a pussy or two to lick."

Perry's eyes just about bulged out of his head when he saw me, strutting up the aisle, the music thumping and throbbing out of the ballroom already, and his pajamas bulged in front, so as I walked into his arms, I slid my hand down his front, cooing at the silk of the material, before palming his cock enticingly.

"Later!" I whispered into his ear, before grabbing his hand and pulling him into the party.

We had two drinks each, while we stood and watched at times, always hugging or holding hands, and sometimes danced, wading into the crowd, bumping into bodies left and right, men and women, no one upset and everyone celebratory and happy.

When the costume judging began, we faded to the back of the room, even after Perry softly suggested I could enter the contest, but I had no interest in that, happy enough and preferring just to be with him, arm-in-arm, and then we spent another hour or so after the music kicked back up enjoying the atmosphere, the revelry and the freedom.

Back in his stateroom we both realized that it was our last night at sea, but the tinge of sadness of things ending was more than overcome by the deluge of joys we'd made, the both of us honestly wanting there to be more, and we talked briefly about continuing things after we got back home, and when Perry whispered that he would be "as right as rain" if I wanted to move in with him and live as Katrina all the time, I burst into a sobbing spate before kissing him again and again and saying, "YES!" in between, until both of our kettles came to a boil and Perry pulled up my dress to above my waist before almost ripping my G-string panties off, giving me one quick thrust of two-fingered lubing, before pushing me face-down onto the mattress, trapping my arms under me, quickly knee-walking himself into position, his legs outside of mine, laying his whole body forward and onto my back, putting his head behind mine and to the right, his mouth close to my ear, and with his hands on my shoulders to use as a grip, he slid his cock straight into me.

I screamed out, muffled by the mattress, a sixty-forty mix of sheer raw thrill over nerve-searing agony, white stars in my closed eyes, waiting for the exquisite ecstasy that always followed, and sure enough it showed itself quickly, quicker than usual, and my second scream, still muffled, was one hundred percent enthusiastic.

"D-O-O-O-O M-E-E-E-E!"

Perry's ragged voice breathed into my ear.

"K-A-T-R-I-N-A!"

He purred it.

Then he fucked me.

There's no other way to describe it, no genteel euphemism for the act.

He fucked me.

Far more furious than our previous love-making, Perry launched at my ass with his cock, again and again and again, slamming his body into me like a pile-driver, forcing the air out of my lungs with every stroke, claiming me, my whole body wincing with every slam, shock travelling through my muscles and bones in every direction, the most vigorous physical struggle of my life.

AND I LOVED IT!

I loved every brutal second of it, every apocalyptic wave of sheer ecstasy. I loved the serious physical endurance, being the human sexual version of the punching bag, and I never wanted it to stop. The longer the better, I kept hoping.

When Perry ramped up to his final ferocious level, I had one second to flash on one thought.

I hadn't cum.

For my entire existence, thirty-three years, the idea of having sex and not cumming was absurd to me, it was ridiculous. Cumming, I used to think, was the whole point!

But that was the sad-sack talking. The loser. The old me.

Katrina was on a winning streak.

The whole point, I knew, intrinsically down to my DNA, was the doing of it.

As he literally slammed into me for his final dozen thrusts, savagely, with the strength of a man, a lion, I saw white stars in my closed eyes and I screamed out one long shriek, as Perry screamed into my ear one long ferocious growl.

We rested, arms wrapped around each other, and it was only then that I realized that while I hadn't had a gigantic orgasm, I had, in fact, had several smaller ones, because the mattress under where my crotch had been was soaked. I'd spewed out little streams instead of big explosions, as he'd pounded himself into me.

On the plane home, we asked if we could be seated together but it didn't happen, so he was three rows up from me, so we couldn't really even see each other. Just before they closed the door, the last two people ran on.

The woman who did my makeup, and her brother.

As they made their way down the aisle, she saw me as she was glancing ahead, and gave me a smile, and then a look, like, did you get laid or not?

I grinned and nodded.

Then her head nodded backwards once and to the right, almost behind her, pointing at her brother, and as she walked by me she leaned over a little, putting those magnificent breasts almost in my face, and said, "he got himself some dick too, same as you."

Her brother looked exhausted.

Perry waited patiently in the taxi we took from the airport while I ran up to my apartment and filled three huge black garbage bags with all the rest of my lingerie, and enough men's clothes to get by for a few days, when I had to wear them. But I was hoping I wouldn't have to.

The sensual life I'd discovered wearing women's clothes led to the sexual life I'd discovered with another man, and while I had no idea what the future actually held, I did know that for the time being I wanted to live large, full-time, as the real me, the honest me, as Katrina, a gay feminine cross-dressing man.

Leslie cried tears of joy for me on Saturday morning. I spent almost four hours there, telling her everything, every little detail of my trip, and what I did and how I dressed and how I felt. With her encouragement, I talked about the sex too, the love-making, the celebration of physical pleasure that two people can have, and should have, every time, if they let go of their civility and just behave like the animals that we are.

Giggling, Leslie confessed that when they're making love she is almost always begging her husband to do her harder too, knowing and understanding that he was hesitant about hurting her and appreciating his care, even after all their years together, but constantly amazed at her level of intensity versus his.

"The way I look at it," she said, seriously, "making love is fine, it's wonderful, of course. But sometimes," and she paused, smiling, "sometimes we just want to get absolutely fucked senseless, don't we?"

If the subject arises in general conversation and people ask me if I still buy lottery tickets, I say yes, the one for the Children's Hospital, because it's a good cause, but I can honestly say that I've stopped buying the regular ones, the weekly ones, or the scratch-n-wins.

Why would I?

I've already won the jackpot of life.

Katrina.

THE END