A Familiar's Fate Ch. 04

Chapter 4

When I awoke the next morning, I faced the same decisions as yesterday. How to prepare myself? What to wear?

Yet this time, I was well rested. I felt quite peaceful in the pink nightie I had worn to bed. So when I was in the shower, I didn't think anything of it when I used the pink razor to clean up some slight body hair. I rather enjoyed the scented body wash and shampoo. And there was no question that I would be styling my hair to look nice and show off its length and body.

In the bedroom, I once again looked within the drawers and the closet. I reached into the panty drawer and found a white cotton pair with pink hearts. They were cute, I put them on immediately.

Looking through the sock drawer, there were lots of pretty colours and designs, but I was hoping for something more elegant. And that was when I found the pantyhose. Yes, sheer pantyhose. I selected a new pair and rolled them up. They also had the added advantage of keeping my penis snug, so there was virtually no indication of a bulge in my panties. Perfect.

In the closet, I perused the various skirts and blouses. But then I saw it. The most gorgeous magenta summer dress. Cotton with lace trimming, and a long v-neckline.

It was the epitome of femininity. Yesterday, I had done my best to minimize this at all costs. Yet this morning for some reason, I wanted to emphasize it. Karen was happy when I was feminine. And I wanted Karen to be happy. It was as simple as that. And I thought it was pretty, and I wanted to wear it.

I slipped it on, and playfully rolled my hips to see the hem of my dress sway. I giggled at the light and pretty fabric, and how wonderful it made me feel.

There was still something missing. I looked again at the closet and dresser, pondering what accessories I could use.

And once more I had an unusual idea. I could wear shoes. Like everything else, they would fit me. And she certainly wouldn't expect me to know how to walk in heels. She'll love it. I found a pair which matched the dress, and the heel wasn't too extreme. Only about 2-1/2 inches.

I was practically giggling as I walked down the stairs. It had been sometime since I had worn heels, but it came back to me. The stairs were the scariest part. Once I reached the ground floor, I was more at ease.

It was late in the morning, which was unusual for me to sleep so comfortably. Still, I had awakened before her this time.

So, I decided to surprise her by making breakfast. I could hear some noise upstairs which suggested she was awake and having her shower.

By the time she made it downstairs, breakfast was prepared and laid out on the dining table.

She gasped when she saw me in the dress. Rushing up to me, and embracing me she practically squealed with delight. "Christine you look lovely."

I was so delighted by her response. And it was wonderful to be held in her arms, her bosom pressed into me.

She stepped back to look at me, examining the dress. Her fingers dangled along the trim belt. She loved the flare of the dress helm, given my hips a wider curve shape. The hem of the dress was just above the knee.

My legs looked fantastic in hose, she said. I was blushing with pride, and felt so beautiful.

By contrast, she was wearing slacks and a button-up, collared shirt.

I did a slow twirl before her, allowing her to see all sides. And once again the open air excited me as my dress swayed over my thighs.

She gasped, "oh my..." Her hand was over her mouth in shock. "You're wearing heels."

At first, I wondered if I had committed a faux pas by wearing them. Perhaps it was too soon? Perhaps I shouldn't wear them in the house?

Yet the beaming smile on her face set any worries aside. "You can walk in heels. And they match your dress."

I was blushing. My face likely had the same rosy colour as the dress and shoes. I looked down sheepishly. "Yes, well growing up with my mother and my sister, I experimented a little."

This wasn't the whole truth. Yet being a closeted sissy seemed to be a believable line.

"I haven't worn heels in years." That was the truth.

She laughed with delight. "Well I'm glad. You look gorgeous."

I directed her to the dining table. Leading the way, I noted that the heels made my hips sway with each step. I certainly loved to watch women walk in heels, and now it was my ass and legs on display. It felt sexy.

She sat down, and took a bite. "You truly are a great cook. You belong in the kitchen." She was savouring every bite.

I smiled in return, pleased that my work was appreciated. And it was enjoyable to work in a full kitchen, rather than the cramped counter at my place.

I was enjoying the food as well.

After breakfast, I cleaned up while she stood to the side watching me. She asked me who taught me to cook, and seemed genuinely pleased when I told her it was Alex, my mother's 'housekeeper'.

We chatted about our plans for the day. Then, a variety of casual things. It seemed that I was at last able to talk with a beautiful woman, now that any man-woman sexual tension was eliminated.

The entire time, I felt her eyes upon me, scanning my body. I had spent countless hours staring at her, admiring her beauty. It felt strange, but also exciting, to now be on the receiving end of lustful stares.

Karen informed me that she had a dinner meeting with an old friend and colleague, but most of her day was free.

I didn't really have any plans.

Looking me over in the dress, she was getting some wild ideas.

"How about we go for a mani-pedi? We could do your nails a nice pink or red?"

I shook my head. How would I explain that tomorrow at work?

"We could get our hair done. I think you'd look amazing with a perm. You have such great hair. This would really make it pop."

I had to think about that for a moment. Spending an hour or two with the ladies in the salon sounded like fun. "No, I don't think so. My hair is already too long. I don't want it to 'pop', when I'm at work, or on the street."

She paused to consider pressing me on this topic, but decided to relent for now.

"How about we stay in?" I interjected hopefully. "I could make it worth your while."

The implication was clear. I wanted to be on my knees, tasting her sweet nector.

She smiled. The offer did have its appeal. However, she shook her head. "How about just going out to the mall? I want to show off my pretty sissy."

Precisely what I didn't want. I shook my head vigorously. "Oh no, I'm not ready for that."

My choice of words revealing. Ready. It suggested even I knew it was inevitable.

She gave me one of her piercing stares, doing her best to unnerve me. It always did.

I nervously fidgeted with the hem of my dress. Perhaps this had been a mistake. My earlier exhilaration had now turned to a nervous dread.

She relented. "Well, if we stay in, can I at least see my sissy in makeup, and style her hair?"

'My sissy'. Those words said so much. She took pleasure in emasculating me. However, I was hers. How could I possibly refuse?

"I guess that's fair." My nonchalance hiding some lingering fear, but also some arousal.

"Excellent, let's go." She took me by the hand, and led me upstairs. Her excitement was contagious.

Why did she derive such pleasure from seeing me as a woman? I only knew that it did.

I expected to finally be admitted entry to her bedroom. Yet, alas, it was not to be. She led us once again into the pink bedroom, my room.

"Let's see how we can accessorize!" Now that I was the subject, she was sounding very feminine, like a daytime talk show host, and her model about to be transformed.

At first, she scanned my outfit to determine if any changes were necessary. She smiled. "The pantyhose were a good choice. They should ensure there will be no unsightly bulges "

My cock, now straining against said hose, would be an unsightly bulge? At this moment, wearing a dress, she was right.

I was directed to sit down in front of the vanity mirror.

"I'll be right back." She walked out, leaving me staring uncomfortably at my reflection. Who was this androgynous figure, with long straggly hair, a pale face, and wearing a dress.

She quickly returned with a few items in hand. "Consider these your starter kit. You can use them anytime you come over."

I was completely tongue-tied. Having my own makeup kit? This was beyond playing dress up one afternoon. On the other hand, it was an open invitation to return to her home.

"First of all, I know you don't want anything permanent done with your hair, but I want to see your hair styled a bit."

I nodded. "Just for today though, right?"

"Yeah, yeah. I'm not cutting it, or adding extensions. Nothing you can't undo."

Her tone was far from convincing. Regardless, I nodded my consent.

She started by straightening my hair with a comb, which I had mainly done before. Yet, I was nervous as she proceeded to use a flat iron, and methodically worked strand by strand. It was a completely novel experience for me. I watched silently in the mirror, not knowing what to expect. I thought some of the twisting of the iron was giving my hair some slight curls, but what did I know.

The final effect was jarring. I knew my long hair could be perceived as feminine. Yet, to see it with some lift, gave it a whole new dimension.

I did not know how I would undo this overtly feminine hairstyle before tomorrow. Yet, before I could object, she was moving on to make-up.

Karen began to apply some foundation, hovering over me. The subtle touch of her body against mine, and her lovely scent, distracted me.

"I wish your first time applying makeup was in a salon." She appeared hesitant on how to proceed.

"You have done this before, haven't you?" Her sudden lack of confidence unnerved me.

"I've never done another person's makeup. I've only done mine, but I was never much into fashion, modeling, and all that stuff." Indeed, she was not wearing any makeup now. "So, I'm hoping my routine for an evening out is enough."

At least she wasn't in the habit of feminizing men. I wasn't sure if being singled out made me special, or a freak.

"No makeup, along with this pretty dress and heels, looks strange."

It would be strange for me to NOT wear makeup? She didn't think I looked strange when she first saw me in the dress?

The giddy spirit which had inspired me to wear a bright magenta dress still had a hold of me, so I welcomed the sensation of being further feminized.

I felt it was no longer an 'if', but 'when', that I would go out in public wearing a dress. Karen had offered me a reprieve, but we couldn't hide at her home forever. When that day comes, I wanted to 'pass'. There could be nothing more humiliating than being seen as a guy in a dress.

"Fortunately, we appear to have the same skin tone," Karen observed. "... and you have great skin. My makeup should work great."

She looked closely at my face, ensuring that she had applied the foundation evenly and checking for blemishes.

I blushed, unaccustomed to this level of scrutiny of my facial features. Part of me wanted to lean forward and kiss her.

Moving on, she lightly applied some powder, and then blush. Despite her earlier protestations, she was working with a well-practiced hand.

Next came the eyes. She instructed me how to apply the eyeshadow, which she carefully touched up. Mascara and eyeliner were then applied.

She was taking her time, clearly having fun. I had to trust that she wouldn't make me look as foolish as I felt.

It all felt strange, and even ticklish at points. Women do all this routinely?

Last, but not least, came the lips. A really pretty combination of light pink lipstick and coral gloss.

The transformation was complete, and the effect was remarkable. With just a simple makeup routine, I had the delicate features and rosy complexion of an attractive young woman. It was hard to believe I was actually a man.

Karen was equally pleased by the result.

There was one thing outstanding though. She held my ear and looked closely, as if confirming her observation. "Christine, why aren't you wearing studs or something? I can see that your ears are pierced, but you're not wearing anything."

Damn, she noticed that. "Oh yeah, I used to think it would be cool to wear earrings. I guess I just grew out of that phase."

Considering the piercing hadn't closed back up, I had clearly worn earrings much more recently. She simply gave a knowing smile. Obviously, her sissy was far more familiar with women's dress than he was letting on.

"Well, I think I have a few pairs which will suit you. It's good that you're already pierced."

She rummaged through a nearby drawer, and reappeared with a pair of amethyst stud earrings.

"Wow, Karen, aren't they a bit elaborate, or expensive?"

It was all I could think to say. Now that she was pressuring me to leave the confines of the house, I was increasingly self-conscious of my feminine appearance. I was in the deep end, but afraid to swim.

"No, I think they'll match nicely with your dress." She handed them to me.

Reluctantly, I took them and put them on. I was really having second thoughts about this. I had not expected to look this good as a woman. Hell, I was gorgeous. The geek was now a babe.

With my transformation complete: dress, shoes, hair, earrings and makeup; I headed back downstairs as a new woman.

Karen looked at me with a lustful gaze that was completely unfamiliar to me. It made me exhilarated, proud, and somewhat nervous.

"Look at you, all dressed up with no place to go. Are you sure we can't go for an afternoon stroll? Don't you want to show off your new look?"

I suppose women did dress up for an evening out, and they wanted to be seen. I could somewhat understand that now. Yet still, that prospect terrified me. I shook my head.

"Suit yourself, but I think you're missing a golden opportunity. You could really turn some heads."

It donned on me that she was probably right. Men would gaze at me, and find me sexy. They may even flirt with me.

Sure, women may appreciate my look and style, but they wouldn't be attracted to me. I was now an attractive woman, who would likely gain the attention of men.

That thought terrified me. I'm not gay.

She looked at her watch. "Wow, it's almost 2:00. Time flies when you're having fun."

We had doing my makeover for over 2 hours. I had no idea it had been so long. I was utterly lost in the moment.

Rather than turning men's heads, I hoped that I had excited her. And when she looked at me, she seemed genuinely happy. Even, attracted to me?

Her attention fed my ego. Perhaps I wasn't the consummate loser? Perhaps, this time, I get the girl? So what if she was only attracted to me as a completely feminized sissy, if I earned her attraction?

This heady feeling was dizzying. At least that is what I would tell myself later.

I leaned forward and kissed her. A deep passionate kiss.

She backed away, startled. "What are you doing?!"

Her harsh tone, an undeniable rebuke. "I.. I... I don't know. I just thought..." I stammered.

"Did I give you permission?"

"No, I just thought..." Her anger caught me by surprise. I thought she had given me 'the look'. I've never received a look of desire, so what did I know. She had kissed me last night. "I just thought you liked me."

I looked down with shame and despair.

She relented a bit. Her tone softening, and she smiled. "Oh, I do like you sweetie." Her hand caressed my cheek as she stared into my eyes. "It's just... kissing me like that.. assertive. That's something a man would do."

But, I am a man. Even I had difficulty believing that now. "Don't you want to?..." Kiss, make love, have sex, fuck?

The desire unspoken, but obvious.

She shook her head. "I told you. I'm never going to have sex with you."

I looked down, crestfallen. She did say that, but then she gave me the look.

"What about, you know, last night?"

She grinned. "Oh, we'll definitely be doing that again. But..." She looked away, searching for the right words. "Men typically only do that as foreplay. I thought you were different."

Was I? My desire for her was undeniable. And yes, I did fantasize about losing my virginity with her. Yet, I have always been terrified that I would never measure up. Could I truly accept that it would never happen? That I would forever be a virgin.

"I'm sorry. I just want to be with you." I simply wanted to reset, and get back to her regarding me with pleasure.

"Ok," she nodded. However, I don't think she really believed me.

She looked at her watch. "Wow. Where did the time go. I need to get ready for my dinner engagement."

I was crestfallen. No more play for us today. I think she was avoiding me. I had refused to go out in public dressed as a woman, defying her. Now, I had to endure her disappointment.

I stood in the living room, stunned as she dashed upstairs. It was like the temperature of the room had changed within minutes from steaming hot to ice cold.

She re-emerged with her hair brushed back, and a business-casual look. Her white blouse, slacks, and jacket looked sharp. Yet, it was a direct contrast to the evening dress, and full makeup, which I was wearing.

She was also holding a small travel bag, dragging it behind her on its wheels. It seemed odd to bring this to a dinner. Yet, she said she was meeting an old friend, so who knows what she was bringing. At the moment, it was the least of my concerns.

"Let me drop you off at home. Your laptop, wallet and keys, I believe are down here. Perhaps I should giive you a purse as well, so you can carry what you need."

I looked down at what I was wearing.

"OK, I should change." Although, it was not clear what I could change into, since my pants were destroyed.

"Sorry, we don't have time. You're not really in a rush to go back to your drab, and ill-fitting men's clothes are you?"

The glare from her brokered no argument. So like always, I relented.

I was getting flustered and nervous. Where to start? Going home, wearing a dress. I didn't know my neighbours. But still, what if they saw me?

Where did the time go? Had we really spent an afternoon doing my makeover?

A purse? I wasn't going out in public. Why would I have a purse?

More than anything, there was a sadness that my adventurous weekend with the woman of my fantasies was coming to a close.

I silently pondered all these things as we headed out to the car, and Karen began driving. Finally breaking the silence 10 minutes into our journey.

"Karen, how am I going to remove all this makeup, and change my hair style back? I thought you just liked to play at your home, and you said this wasn't permanent."

What I really wanted to ask, but couldn't, was why I was being summarily dismissed.

She gently brushed my face with her hand. A quick glance before her attention returned to the road. "Oh Christine. I thought you liked being pretty."

I did, or at least I think I did. A real man would not want to be called pretty. Did I have to wear women's clothing to please her? How far was I prepared to go?

"I do. But, I want to be with you, at your home, in private."

"Oh that's sweet. But this is more than a sexual game. You really should normally dress in a more feminine way. You really look pretty."

She really believed I was pretty? I didn't know what to think of that. I wanted Karen to find me attractive. Yet 'pretty' is hardly an attribute men aspire to.

For the next few minutes, I guided her to my place. Once we were parked in the guest parking area of my dingy apartment building, she turned to look at me.

"This weekend was really, uhmm, pleasurable."

For a moment, I thought back to last evening, licking her pussy. I nodded in agreement.

"See how much better it is when you stop pretending to be a man?"

Pretending? I am a man. Yet perhaps that argument lost some weight when you are wearing a dress.

"I can't wear this at work." I was referring to the dress, the makeup, the hair... everything.

"Perhaps it is a bit sudden. Yet try your best."

She stepped out, opened her trunk to retrieve her travel bag, and handed it to me. "To make up for the pants I ruined with the wine, I grabbed a couple pair. I think they will fit. I also packed some tops, undergarments, and your makeup kit."

I hadn't really paid attention to the bag before now. Yet I was quite certain it contained ladies' slacks and blouses. And of course, 'my' makeup kit.

Before I could react, Karen leaned forward and kissed me. To any outside observer, we would appear to be a lesbian couple. Yet for me, I was too lost in the moment to worry about others. She had kissed me. A deep, intimate kiss.

Kissing permitted when she took the initiative apparently. I certainly wasn't going to object.

She stroked my hair. "My pretty sissy."

A sissy? But I was hers. What else mattered? Except maybe that I was wearing a dress and she clearly preferred me emasculated.

"I love you Karen."

She continued to stroke my hair and kissed me again. "I know."

I retrieved the bag, along with my laptop, and entered the building.

Settings the bag in the bedroom, I opened it to confirm what I already suspected, women's clothes. Granted, they were far more subdued than the dress I was currently wearing, but still. I debated attempting to hide them, but what was the point? No one had ever been to my apartment. And the woman that I loved, yes loved, wanted me to be feminized.

I relived the excitement of the weekend in my mind, deciding to remain in the dress and makeup for the evening.

And once again, I had a sleepless night. What was I going to wear in the morning?