Marc Alone

This is a continuation of my story, the third chapter of what started with "An Unexpected Friday" and continued with "Saturday Morning". It is more introspective, as Marc explores his own femininity and feelings. I believe it is essential to the broader arc of my tale. Please enjoy it, and know that there are more racy bits to come.

It had been several months since I had met Diana, and life had resumed its normal course. The weekdays were filled with work, and I spent my weekends as we all do, varying my leisure activities- riding my bike for exercise and relaxing at home, with the basic chores we all have to do: laundry, the grocery store, etc. Life flowed along, and Diana and I had kept in touch, but her work schedule required her to travel quite a bit, and a large project at my company had occupied a lot of my time.

We spoke on the phone and sent emails back and forth, and it was in this communication that I told her more about my crossdressing. For me, there were two aspects to dressing. I couldn't deny that there was a huge sexual component to it-my desire to dress would ebb and flow over time, and sessions would usually end up with me masturbating to orgasm and then quickly removing my clothes and resuming a male persona. Examining this I realized that the shame I had felt at these desires when younger still lingered. Once I had satisfied my sexual desire, the clothes were put away, to be taken out again when the need arose.

But there was another side as well. Often upon returning home from work, I would slip into what were for me "comfort clothes"- generally just some leggings and an oversize sweatshirt. Although these evenings usually if not always ended up with me masturbating to release, there were other feelings involved- that of deep comfort and relaxation. An escape from the stress of everyday life, of being me. Of course I knew I wasn't unique in this- the research I could do on the internet taught me that many straight men felt this way. And I considered myself to be straight - it was women who I was sexually attracted to- or men dressed as women. So maybe not entirely straight- but whatever it was, I was comfortable where I was. One thing that growing older had done was to make me more comfortable with the realization that my sexuality was deep and complicated. But I had no deep burning desire to dress up and pick up a man. Or really, until that evening with her, a man dressed as a woman.

All this I poured out to Diana, in a series of emails and conversations. For her part, she listened, and supported what I had to say. Aside the sexual bond I felt with her, (for what a time it had been), I felt a growing sense of closeness as I confided in her things I had never spoken to another. At the best of times I simply stopped questioning myself, and enjoyed that she had become part of my life.

Since meeting her I had become somewhat critical of myself when it came to dressing- Diana was so elegant and skilled in her fashion choices and her ability to pass- whereas for all that it felt good, I still just saw myself as a guy wearing girls' clothes. Why I did so came from a variety of emotions. I only dressed in the privacy of my apartment. Diana presented herself boldly to world, and moved freely through it. I admired her for this, and told her so.

Diana was curious about my own dressing habits, and eager to see me en femme. But I held back. The clothes I owned were limited. I had a collection of panties, of course, and a few bras. Several pairs of leggings and a few sweaters. I did own one dress that I felt fit me well, and a stretchy skirt that I loved. A few pairs of tights- and that was pretty much it. I felt unable to live up to the image Diana presented. It was while I was trying to express these feelings to her on the phone one night that Diana interrupted.

"Marc," she said."I've taken the liberty of ordering some things for you. I hope you are ok with that. I think I've gotten the sizes right, but let me know if we need to send anything back."

"Oh" I replied "you didn't need to-"

"Now don't object" she interrupted. "I make a good salary, and I wanted to give you a present. A token of appreciation for all you've done for me. You make me feel young again. And, I admit, I'm curious to see what a cute woman you make. I may have a few lesbian fantasies lurking around in my subconscious..." her voice trailed off, and my stomach gave a little leap. The thought of being dressed while with her turned me on as well.

"That sounds like something I can get on board with," I said casually. In truth, one of my deepest fantasies began with dressing up with a fellow cross dresser and ended in a night filled with passion....Until I had met Diana, I had never considered the possibility that my fantasy might become real.

"Marc, I don't mind telling you I'm getting hard just thinking about it." Diana whispered over the phone.

"Me too." I murmured back.

"So, anyway," Diana chuckled, lightening the mood. "Expect something in the mail soon. Oh, and I've managed to arrange my work schedule so that I'll be coming into your town the weekend after next. For some "me" time. So I'll see you soon, sweetie."

"I can't wait."

"Let me know how the clothes work out."

"Good night, Diana."

The fact that Diana had sent me a present filled me with a thrill of anticipation. But I also did some deep thinking. I was sure that she had picked out some fashionable items, and I felt I needed to prepare, to be more worthy of them. These weren't just some clothes I could put on to indulge my desire to dress, this was something that she would want to see me in. So

I had some work to do on my end. I needed to, and wanted to, commit.

After work the next day I stopped at the local Target. My heart pounding, I made a few purchases. Pretending to consult a list, I bought (as if for my wife) a few lipsticks- one in pink, and another in a deep red. A small pallet of eyeshadow, and some mascara. A bottle of nail

polish, and remover. I already had a variety of skin care products, but I tossed into the cart some moisturizer and also a shampoo and conditioner that was marketed to women. Suddenly more comfortable with what I was doing, I made my way over to the women's clothing selection, allowing myself to linger in the footwear section. I was lucky that I had small feet, a men's 8. My heart was pounding as I found myself looking at a pair of black pumps with a peekaboo toe. Looking at the boxes, I saw that they had them in a 10. That should fit me. I grabbed them, placed them into the basket, and headed for the checkout. Going through the self checkout line, I thought to myself how great technology was. Placing my purchases in a bag I headed for my car, and went home. I was light headed. I felt proud of myself, and of course I couldn't wait to try on the shoes.

Outside the door to my apartment were a couple of Amazon boxes. Diana's gifts had arrived. Gathering them up I made my way in and closed the door.

Relaxing in the privacy of my own place, I opened a bottle of wine and poured myself a glass, relishing my anticipation. What had she bought me? The boxes were on the table, ready to be opened.

I opened the first, smaller box. Inside were two C cup breast forms. I drew my breath as I lifted them out, feeling their weight in my hands. I had always wanted something like these, but had never had the courage to buy them for myself, even online. I usually filling my bra with socks or rice filled balloons. These were far more realistic, with small pink nipples. Diana had even matched my skin tone.

Cupping one in my hand I brought it up to my chest. They seemed the perfect size and proportion for my chest. The anticipation of opening my gifts had already made me rock hard, and I touched myself through my clothes.

Placing the forms to the side I drew out of the box a satin underwire bra in white, along with matching panties, and a pair of white thigh stockings. They were the stay up variety, with a delicate lace pattern around the top. My breathing quickened as I held the package.

Turning to the larger box I cut it open. Inside were several items. A knee length black skirt, a shorter brown skirt with a bit of a flare to it. A purple blouse in a soft cotton jersey material, with low cut scoop neck, the fabric gathered in pleats under the 3/4 sleeves. There was a white silk blouse, styled like a men's dress shirt, but with full cut sleeves. The silk was thick and soft. I drew my breath as I realized that Diana had spent quite a bit of money on these garments. Under these was the item that again made me realize how hard I was: a soft wool sweaterdress. I caught my breath as I felt it under my fingertips. It was a beautiful shade of dusty green, with a high neck and long sleeves. It would match my eyes. Holding it up I saw that it would probably fall to just above my knees. I couldn't wait to try it on. Diana, ever perceptive, must have guessed at my sweater dress fetish that last morning in the hotel, when I had smoothed her dress back down over her thighs after sucking her off.

I couldn't help it- I felt myself beginning to come, just from my thoughts about the dress and my memories of her small smooth cock. Quickly reaching down I undid my pants and brought out my pulsing cock, already releasing pre-cum. Giving it a few strokes it exploded in my hand. I couldn't believe how just the thought of wearing these clothes that Diana had given me had done this to me. I panted, somewhat disappointed in myself for not being able to control what had happened. Usually after I orgasmed while dressed, I would take my clothes off. This evening needed to be different. I wanted it to be special.

I determined that I would go beyond where I had been before. I wouldn't allow myself to feel shame, or whatever it was that compelled me back into maleness. Leaving my new clothes where they lay I grabbed the Target bag and walked to the bathroom. I cleaned my now soft cock, got into the shower. I washed my body well. I forced myself to slowly soap myself between the legs, under the arms. Taking a disposable razor I began to shave my legs, something that I had never done before. It was a surprising amount of work, but I felt that I did a pretty good job. Once they were smooth, I went further, shaving the hair off my chest. Getting out of the shower I stood before the mirror and continued to remove as much of my body hair as I could. My armpits, which I also had never done before. Luckily I didn't have much arm hair- that I left. I had to be a boy again, I couldn't go too far. I felt myself slipping back into the mood of before.

I looked at myself in the mirror. Now I had stepped beyond where I had ever gone before. Putting down the razor I took the moisturizer, and applied it to my body. I ran my hands down my legs, over my butt, up my chest, feeling my nipples. I could feel myself beginning to get aroused, but this was different. I had the feeling I was stepping into a new skin, moving past simply being a man who enjoyed (for whatever reason) dressing in women's clothing. I felt a relaxed euphoria as I ran my hand over my cock, feeling it's incipient hardness, but staying soft. I reached between my legs, rubbing moisturizer onto my taint, imagining myself feeling the soft wet warmth of womanhood there. Closing my eyes I willed myself back into fantasy.

This felt good, felt right. Grabbing a towel I wrapped it around myself, covering my breasts. Taking a brush I ran it through my hair, trying to form it into something resembling a feminine style.

Leaving the bathroom I walked swaying my hips, towards the clothes I had left on the table. I moved slowly, enjoying the feeling of my now hairless thighs rubbing each other. I removed the towel and took the panties Diana had bought for me, and eased them up my legs. They fit me well, snug. I was aroused, but not hard. Closing my eyes I reached down and tucked my boy parts back between my legs. I reached and picked up the matching bra, first fitting it backwards to do the clasps, then turning it around my torso and slipping my arms through the straps. Again with my eyes closed, I took the forms off the table and slipped them into the bra. Felt their weight. Looking down and opening my eyes I saw the flatness of my crotch framed by the white cups of the bra, the forms filling them out.

Next I put on the brown skirt, and then the purple top she had sent. It pulled tight over my breasts, and then draped loosely down. The soft cotton fabric felt wonderful, as did the skirt, which fell to just above my knees. I turned and moved towards the full length mirror mounted on the wall, looking at myself critically, head to one side. I felt cute, and looking back at me, I felt, was more than just a guy wearing women's clothes. The scoop neck of the top flattered my hairless chest, the breasts that Diana had given me were well proportioned to my size. The legs below the skirt were shapely and hairless. My hair was short, but had a certain feminine style, and fell down over one eye. I thought I looked pretty good.

Walking back to the bath, I grabbed the cosmetics I had bought, as well as the shoes, walked again the the mirror in the hallway. Trying on the shoes, they fit me well. The lift of the heels made my calves taunt, adding shape to my legs. But they didn't really match the outfit, I thought. They were too formal for this cute ensemble. I needed something more casual. Opening the hall closet I found a pair of western style cowboy boots. They were men's shoes, but as I slipped them on and looked, I realized that they completed the outfit. They came to mid calf. Again I felt a thrill as I looked at myself, and felt my cock, which had moved from between my legs, begin to get hard. I fought the urge to touch myself. I had to carry this moment to the end. Feeling girly, I indulged in a twirl. I felt the hem of my skirt brush over my thighs.

I slipped out the lipsticks I had bought, considering the colors against the hue of my blouse. The deep red, I thought, opening it and apply it to my lips, which took on a feminine shape, fuller under their color. I wasn't totally at sea here: I had played with cosmetics before, and had watched tutorials online. A light eyeshadow in a purple. I accentuated the curve of my eyes with a bit of eyeliner. Nothing too heavy. Then the mascara, which amplified my naturally long lashes. I was lucky there. Looking again I saw a pretty woman. No young girl-that was impossible. But a reasonably attractive woman in her late 30's, in a pretty and playful outfit.

I breathed deeply at the new me I saw there, feeling her in myself. My cock had softened again, which somehow deepened the erotic feeling of comfort I felt inside. I felt whole in this new skin of mine. Comfortable. I sipped at the forgotten glass of wine, saw the mark my lipstick left on the rim. Picked up my phone.

"Marc!" Diana answered her phone "How are you?"

I hesitated. "Actually this is Samantha," I said, my voice soft. "Thank you for the gifts."

"Oh...hello Samantha," her voice softened. "And did I guess right? Do they fit well? Tell me, what are you wearing?"

"They fit well" I breathed " I'm wearing the underwear, of course, and the purple top and brown skirt. I feel...wonderful..."

"Well Samantha, I'm so glad you like them. I just can't wait to see you in them. I bet you are beautiful. But not the sweater dress? I figured that would be the first thing you tried on." Diana's voice was playful, flirtatious.

"I think I'll save that for when we meet," I said. "Oh Diana, thank you so much. I feel so good in your gifts right now. You really have wonderful taste. I've never felt quite like this before." My heart beat strongly as I gushed. Allowing myself to express emotion, this was part of it too.

"Mmm....just the thought of you in them is turning me on." Diana said, moving the conversation in another direction. My cock stirred at the sound of her voice. I wanted to go there, but not yet.

"Be careful, Diana, I don't want to get my new panties all wet so soon." I flirted back in this new persona.

She laughed. "Well, I remember how quickly you came when I was in your mouth- I better be careful or yes...." she trailed off.

"Mmmm" I said, thinking of that moment. "Yes." I laughed self consciously. "Well..."

We spoke for a short while after that, discussing the practical details of her imminent arrival. She again said how much she looked forward to seeing me. We said goodnight and hung up.

I lounged a bit, feeling good. I focused on the sensation of my clothing- the tightness of the bra around my back, the softness of the panties as they encased my cock. I reached up, caressing my breasts, feeling the soft cotton of the top sliding over the satin of the bra, the the cups full with the heaviness of the forms. Leaning back on the couch, I let my hands softly caress my hairless thighs, climbing higher under my skirt, touching myself through the panties. I tasted the lipstick I was wearing. Slowly I began to climb towards the edge, feeling my oncoming orgasm as it built up in me. Opening my eyes I gazed at the soft curves of my chest. Considered Diana, the fullness of her under the sweater dress she had worn...

I forced myself to stop. Put my hands to my side, breathing gently, concentrating on control. My cock pulsed in my panties, desperate for release. Standing up from the couch, I relaxed. I didn't want to cum, didn't want this warm and glorious feeling to subside. I knew that if I allowed myself to orgasm I would feel compelled to remove my clothing, and that the moment would be gone. I was convinced that I would be able to fight off that feeling, but I didn't want to, right now. Here was another step I had never taken. I wanted to live this womanhood for a while longer.

Moving to the table I looked again at my new clothes, touching the soft fabrics, imagining myself in them. The soft femininity of the sweater dress overwhelmed me. I longed to feel it hugging my new, smooth and soft body. Overwhelmed with this warm feeling of sexuality I felt rising in me I slipped out of the skirt and top, stood there in my panties and bra. My cock strained for release, pulsing again, pushing out against the satin, poking its head over the waistband of the panties. Looking down I saw a wet shine of precum. Again my fingers trailed down the dress on the table. I was trembling. A part of my rational mind marveled at the strength of my feelings. I was exploring depths of myself I had never experienced.....

Coming back to the present, I saw myself in the mirror. Breathing deeply I looked again at the woman I saw there. I shook my head, wishing I could feel the swish of long hair over my shoulders. Something for the future, I thought. Another level I could reach. I walked into the bedroom, and opening my dresser picked out a pair of yoga pants, slipped them on up my hairless legs and over the panties. An oversized long sleeve tee shirt followed, and draped over my breasts. Back in clothes I was more familiar with my lust subsided. I would sleep like this, I thought. I'd slip off into unconsciousness and wake to feel the clothes hugging my body. Wake as a woman.

I moved into the bathroom, removed my makeup. Even the process of removal made me feel more feminine. I applied moisturizer slowly, enjoying the self indulgence. All tempered by this feeling of relaxation and comfort, underpinned by sensuality. It was time for bed.