Senior Finally Feels Alive

Once again a big thank you to Tania Tulle for her guidance and editing skills. I don't know what I would do without my friend and mentor.

If you haven't read any of her great stories, get going! You won't regret it, they are all fantastic!

I've spent most of my life hiding a secret fetish--or should I say, an obsession. I'm not complaining; my life has been fine. I had a decent job, a lovely wife, and two great kids.

My obsession did mess up my family life, but maybe that was for the best. Ever since I was a teenager, I've had a love for anything nylon--especially lingerie, stockings, panties, and pantyhose. I was even tempted to try wearing them, but I never got up the nerve.

I've always loved the look of stockings on a nice pair of legs--the sheen, the sound they make when legs are crossed, and especially the feel of nylon. I've had many dreams of wearing them myself.

I figured that once I got married, I'd forget about the temptation. But it turned out to be the exact opposite.

I used to buy my wife sexy items, and in the early days of our marriage, she would wear them for me. I loved running my hands over any part of her body covered in nylon, especially her legs. One of my favorite things was having sex while she wore a garter belt and stockings.

I'll never forget the first time she agreed to wear them. She had me take off my clothes, get in bed, and promise not to open my eyes until she said to. When she finally said "okay," she stood beside me wearing nothing but a garter belt and nude sheer stockings.

My cock immediately started to rise to the occasion. She crawled up to me and put her pussy in my face. As I was licking her clit, I rubbed my hands over her legs feeling the smooth gossamer fabric pulled tight on her thighs. She had an orgasm much quicker than normal.

I just loved looking at the glimmering sheen on her legs. It turned me on even more when I started fucking her and she wrapped her legs around me.

That phase lasted a few years, but gradually, she wore the things I bought her less and less.

Finally, one day, she admitted she was tired of playing "dress-up" for me. In fact, she said she was going to give everything to Goodwill.

I was disappointed but offered to take the bag she'd filled. I put it in the trunk of my car and waited for a time when she wasn't home. That day, I moved the bag into my workshop behind the house. I found a good hiding place and started thinking about how to move forward.

That was the beginning of my journey toward transformation.

At first, I only snuck a few articles from the bag into my travel case when I went away on business. My heart pounded every time I did it--but it was worth it.

I had never enjoyed business trips until that one. All I packed was a pair of pantyhose and a négligée.

When I arrived at the hotel room, I stripped immediately. I tried to copy everything I'd seen about putting on pantyhose. I did a decent job--and just the feel of them being pulled up my legs gave me incredible excitement and pleasure. The négligée only added to the experience.

I started walking around the bedroom, feeling a mix of nerves and excitement. I kept thinking about what I was doing. I'd waited a long time, always expecting to change my mind or talk myself out of it. But there was no way that was happening--not with how deep my love of nylons ran.

Just crossing my legs and rubbing them together felt amazing. I ran my hands all over my chest, my body--especially my legs.

I couldn't understand why any woman wouldn't want to dress this way. Who needed pants, when dresses, slips, and stockings existed?

I got on top of the bed and started running my hands all over my body. I pinched my nipples through the nylon and ran my hands up and down my legs. The more I did it, the harder my cock got. I quickly undressed before I made a mess--I didn't want to stain my new favorite clothes.. It wasn't much longer before it all got too much and I was shooting ropes of cum unto my stomach.

I cleaned up and put on my sexy clothes again to sleep in. I hated having to take them off the next morning, but I had meetings all day.

I repeated the ritual the following night--and on many business trips that followed.

Each trip reinforced my feeling that I was born to wear sexy nylon fabric. I couldn't get enough of the sensation. It was becoming an addiction.

But nothing lasts forever. With a promotion at work, my role changed. I was needed in the home office, and the traveling stopped.

I behaved myself for about two months, keeping the clothes hidden and trying not to think about how they felt on my skin.

Eventually, I gave in to temptation and started dressing again when I knew my wife would be away for a while. This new arrangement was better than nothing--but it was nerve-wracking. I began to long for a time when I could dress however I wanted, whenever I wanted.

You probably know the old saying--be careful what you wish for. Sure enough, after a couple of years sneaking around the house in lingerie and pantyhose, I got caught.

I was watching TV when my wife told me she was going out for the night with the girls. I immediately went to get my clothes and change. I put on pantyhose, a silky slip, and a soft nylon dress I loved. I was already feeling aroused.

I was just about to sit down and start my usual leg-crossing routine when I heard a key in the front door. I ran for the stairs, but I had no chance. The scream I heard behind me confirmed what I feared--she had caught me in the act.

I'll spare you the yelling, the name-calling, and the finger-pointing that followed over the next few days. Eventually, we both calmed down and apologized to each other. We came to the conclusion that we had just drifted apart. Her shock discovery the moment we both needed to realise how different we had become. We agreed to end our 30-year marriage but to do it fairly.

Before the divorce was finalized, we decided on how to divide our assets. We had been fortunate over the years and saved well. We'd both inherited money from our parents, and the house was paid off.

Since I was close to early retirement and had a generous pension, I didn't mind signing over the house. And the fact that I was walking away with over two million dollars made that decision easier.

I found an apartment with a short-term lease and moved in. Surprisingly, my wife and I parted as friends--which was nice.

I spent the next ten months dressing as a woman every day. I dressed all day on weekends and at night during the work week. I wore panties under my clothes to work every day. Now it was my legs with the sheen I loved.

At this point, I couldn't even regret the divorce. The freedom to live how I wanted, the feeling of wearing a dress over stockings was incredible, and I wanted it to be part of my everyday life.

Just walking around the apartment with my legs in nylon and hearing the sound of them rubbing together drove me wild. I had already shaved my entire body, but I knew I'd need to do more in the future.

I slowly added to my wardrobe--only soft, feminine lingerie: panties, dresses, garter belts, stockings, and of course, pantyhose. No pantsuits for this girl!

I decided I would use my wife's name, Jennifer, as my femme name. After all, part of the wardrobe had been hers anyway. This new Jennifer would appreciate dressing like a sexy woman!

I also picked up a couple of pairs of heels--very low heels, a sort of "starter set." I doubted I'd ever graduate to stilettos. I practiced walking around my apartment every day and eventually got the hang of it.

My next step was learning how to apply makeup. I watched countless tutorials, which helped, but it still took a long time to achieve even a decent look. How do women do it so effortlessly? I was jealous of their skills.

Eventually, I bought two wigs--one blonde and one brunette. I figured I'd try both and switch between them.

My wife and I had talked at length about what we wanted to do when we retired. Her dream was to tour Europe--London, Paris, Rome, and more.

I didn't hate the idea, but I was more inclined to take a cross-country car trip. When I mentioned wanting to see some of the baseball stadiums I'd always dreamed of visiting, she met it with complete silence.

But now I was free to take that trip--and as a huge bonus, I could dress how I'd always dreamed.

I promised myself I would take only two suitcases. As I packed, I found myself filling one of them with female clothing and cutting back to the bare minimum of male clothes. What the fuck was I doing?

Too late to change my mind now--so I set out on my adventure. I had always wanted to see Wrigley Field. Not because of the Cubs, but to see the ballpark. So I headed west toward Chicago.

I decided to drive to Pittsburgh on the first day, about a six-hour trip. I planned to stay at least three nights and maybe visit the Pirates' stadium. I found a nice motel nearby and had dinner at a local restaurant.

That first night was fantastic.

I had picked up some hair remover and rubbed it all over my body before taking a shower. It did a pretty good job, but I knew I'd probably need another application.

Not that it mattered--because when I pulled the stockings up my legs and attached them to the garter belt, I got an instant erection, even before adding the panties, bra, slip, dress, and wig.

As good as pantyhose felt, this was even better.

I looked in the mirror and saw an attractive older woman--maybe a "cougar." I was slim, with nice long legs. My face not too masculine. I was thrilled and excited by the transformation. I loved the feel of dressing like a woman, complete with makeup and a wig.

I must have spent two hours walking around the motel room in heels. I even turned on the radio and started dancing--swaying my hips to the music, feeling very feminine and getting increasingly tempted to go out dressed.

This whole process brought up some of my deepest, darkest secrets. For years, I had wondered what it would be like to be with another man. I would fantasize about what it would be like to pleasure a cock. To feel it inside of me. To feel a complete woman.

But I was ashamed of the feeling--I was a married man, for crissakes. Still, the desire had never truly gone away. And now, dressed as a woman, that urge to serve a man was stronger than ever. The shame I once felt had begun to fade, replaced by something deeper, more undeniable.

That night, I got out some sex toys I'd found hidden in my wife's closet and had brought with me on a whim. I guess she used them when I was away on business. I wasn't judging--just curious how they would feel.

I stopped dancing around and knelt down next to a chair and held a good-sized dildo.

I had always been curious how it felt to suck a cock, so I closed my eyes and started. I swirled my tongue around the head, just like I would like it. Then I moved my tongue up and down the shaft. As I started taking the dildo in my mouth, slowly going deeper, I felt myself getting hard.

I probably should have been questioning my sexual preferences at this point. However, I was just feeling like a woman taking care of her man!

After my fake blow job, I thought I'd might as well continue with my fantasy. I took off my dress and panties and got a towel from the bathroom. I put that on the bed hoping to not make a mess. I had purchased lube for the trip like a good little slut. I took my time getting my ass ready, slowly inserting a single finger, then two and finally three.

I knew I needed to see what it felt like to get fucked and this was the closest I could come, for now.

I lubed up the dildo and slowly started to push it into my ass. It was hurting, but I was determined to continue. Slowly the pain started to subside, pleasure took over.

I pushed the dildo all the way in.

I tried to imitate intercourse as best I could, pushing and pulling the dildo in and out of my ass. My legs were twitching and I was moaning like a woman enjoying getting fucked. My arousal grew and grew.

Without warning my cock erupted shooting cum all over my stomach. One of the best orgasms I had ever felt.

As I drifted off into a satisfied sleep wearing my new négligée, I had a good idea of where this would lead me.

A quick trip out for breakfast the next morning with a lot to think Back at the motel, I did some research and treated myself to another round of hair removal. I wanted my skin to be as smooth as possible. After showering off the gel, I dried off and applied lotion all over my body.

Feeling very feminine, I slipped into a négligée and pulled out my phone to search for an LGBTQ-friendly bar. I found a place called P Town Bar not far away--it looked promising.

I won't lie--just the thought of going there filled me with terror. I went back and forth, debating whether to go at all. But in the end, my new feminine side won out.

Fuck it. Jennifer is going out tonight.

With plenty of time to prepare, I spent the afternoon painting my nails, trying on both wigs, and settling on the brunette for the evening.

Then it was time to get ready.

I dressed in a lacy padded bra, garter belt, and sheer black stockings. I added silk panties, a full black slip, and a little black dress. I looked in the mirror and felt satisfied--I was sure the bulge in front would stay hidden. I chose two-inch heels, since I wasn't ready for anything higher yet. I took my time with my makeup and ordered an Uber.

I stopped to look at myself. I wasn't some twenty-year-old glamour puss, but I looked good. My makeup skills were coming along, the outfit fit well and flattered my figure, and my long legs looked especially alluring in the black, glossy hose.

I caught my reflection and let out a little giggle. "I'd pick me up," I thought.

Just walking outside to the car made me nervous--but also excited. I noticed the driver glance at my legs as my dress rode up while getting in. I liked that. A lot.

But the nerves I felt walking to the car were nothing compared to what hit me when I stepped into the club.

Almost instantly, I got attention that completely surprised me. Before I even made it to the bar, two guys offered to buy me a drink. I politely declined, saying I needed to settle in first and try and calm my nerves.

I found a seat in the corner where I could see most of the action--people chatting, some dancing, and plenty of drinking. There were many crossdressers; some looked better than I did, but honestly, quite a few didn't even come close. I couldn't help but feel proud of how I presented myself.

I ordered a scotch on the rocks to steady my nerves. I was halfway through my second drink when a guy came over and asked if he could sit next to me. Caught off guard, I just nodded.

I gulped down the rest of my drink, still trying to calm myself. He bought me another one, and we talked for a while. He seemed genuinely interested in my crossdressing, and I told him I was very new to it.

As I was finishing my third drink, he placed his hand on my stocking-covered leg. I'll admit--it felt amazing. But it also made me panic. I practically leapt off the stool and told him I had to go.

He immediately started to apologize, but I stopped him.

"Please understand," I said. "This is all still so new to me. I just need more time to process. I'll try to come back tomorrow night and give it another try."

On the ride back to the hotel, I wasn't sure if I was ready to return. That night, I slept fitfully--shame and excitement stirred together, keeping me restless.

And thinking about having his cock in my mouth certainly didn't help with REM sleep.

Still, the next morning, I woke up determined. I hadn't been exposed or humiliated, and that gave me confidence. I dressed in a blouse, pencil skirt, and pantyhose and went out again--blonde wig this time, just for variety. I grabbed something to eat and did some shopping. Every stop gave me a little more belief that I could pass.

It was a great feeling. I even bought a pair of three-inch heels.

Look at Jen go.

Back at the hotel, I rested and built up more confidence. I decided to wear the same outfit that evening, hoping I'd see the guy from the night before.

Another Uber, back to P Town.

My same seat at the bar was open. I scanned the room, hoping to spot the guy--but no luck.

Then I saw another man across the bar smiling at me. He started walking in my direction.

He looked a little younger than me, but I couldn't be sure. What I was sure of was that he was good-looking--and he made me a little excited.

As he sat next to me, he smiled and said, "I'm Frank. And I have to say--it's refreshing to see someone who actually tries to look like a woman. Not just some guy in a dress with over-the-top makeup."

I smiled and replied, "I'm Jennifer. And don't be so hard on the others--it's not easy to transform."

He chuckled and smiled again. "Well, I still think you're beautiful," he said, and kissed me on the cheek.

I couldn't help but wonder what a kiss on the lips would feel like.

He was easy to talk to. He told me more about P Town and why he liked it. He occasionally enjoyed the drag shows, but more importantly, this was the place to meet "chicks with dicks."

That line made me giggle--and he seemed to like that.

I told Frank I was eventually heading to Chicago to see Wrigley Field. That sparked a conversation about our shared love for sports, and time flew by. The drinks kept coming--not that I'm using alcohol as an excuse for what happened next.

At some point, his stool was practically touching mine, and his hand was resting on my leg. This time, I didn't move it. I kept chatting, sipping my drink, letting the moment linger.

I glanced at the clock behind the bar--it was 12:30.

More than three hours had passed. I turned to Frank and said, "I should probably get going."

He gently grabbed my hand. "Please, Jennifer. I don't want this night to end yet. Let me call an Uber--we can go to my place for a bit."

I didn't even hesitate. I smiled and nodded.

The ride wasn't long. When we got to his apartment, he pulled me close and kissed me--softly at first. I was already hooked. Feeling his strong arms around me, holding me tight, his tongue gently exploring mine--I felt more like a woman than I ever had before.

And I wanted to please him.

I started to think about having his cock in my mouth and couldn't get the thought out of my head. Could this be the guy? The right time?

He moved us over to the couch and we made out for at least 20 minutes straight. At this point I was extremely excited. I dropped to my knees in front of him and he murmured I didn't have to do anything.

I said, " there's nothing else I want to do more right now, but just know it's my first time." I haven't seen many cocks in my life but the moment I saw his, I thought it was beautiful.

Since I really didn't know what I was doing, I decided to just do the things that I liked when my wife did them to me. I started by swirling my tongue over the head of his cock several times and then licking down the shaft. I went back and forth licking both balls and underneath. Then back up the shaft to the head several times.

From the beginning, I loved the feeling of his hard penis on my lips and tongue. Far better than a plastic dildo for sure. I was a little worried about the taste but found that I actually liked it.

I could hear from the sounds from Frank that he was getting very excited. My hard cock in my panties was a good indication that I was as well.

I really was into sucking him now and began bobbing up and down as fast as I could. All of a sudden, he grabbed my head and pushed his cock deeper.

I shocked myself that I didn't gag as he erupted down my throat. A slight salty taste for sure but again I found that I simply loved the taste and everything about giving a man a blowjob.

As we were both recovering, I cuddled next to Frank, thinking this was what I was meant to be. As we were lying there, he gave me his plan that he hoped I would agree to.

He had to go on a business trip for 10 days and then he had two weeks off. He suggested that I continue to Chicago and see Wrigley Field, but that I promise to come back to Pittsburgh.

He wanted me to stay with him in his apartment.

I agreed to come back, but said I would have to think about staying with him.

Then I told him I needed to go back to my hotel. Frank wanted me to stay but I needed time to think. This was a lot and as much as I'd enjoyed myself, it was a big step.

Like the gentleman he had been all night, he got me an Uber.

As I headed back to my hotel I reviewed my night with Frank. Foremost in my thoughts was how he treated me as a woman and not some guy in a dress.

Our conversation was great, his touch turned me on and his kisses changed my world. Moving on to his beautiful cock and how I loved my role to take care of his needs.

Every step just reinforced my moving towards full time Jennifer. As I drifted off to sleep, there was no doubt I would be returning to Pittsburgh in 10 days.

To be continued....