My First Night: Erotic CD Lingerie Story

As promised, I bring you the full erotic CD story by Michelle Williams. It’s a sexy story & interesting to read a man experience a bit of what women do… (Oh, and this is hetero erotica — one man dressed as a woman with a woman!)

I’m a cross dresser, though not gay. However, like many men I have discovered the pleasure of having my ass tickled and penetrated during sex, and like many TV’s I have wondered what it would be like to experience sex as a woman.

I was going to have the opportunity to find out.

First, I had to find a willing partner, and that was Alex. She’s beautiful, single and quite uninhibited. Perhaps it was her casual remark that her two big weaknesses were shoes and lingerie; that I recalled very clearly.

“Let’s try it,” Alex said at once, when I’d shyly told her of my fantasy. “I’m not gay either, but lots of us girls have fantasized making love to a woman as well. If you were dressed as one, and we made some ..adjustments, we could try it out.”

I wasn’t sure what she meant by adjustments, but I was game to try. So we met one evening in Miami, and our adventure began.

I had brought my Michelle wardrobe for the evening, a sensuous chiffon dress under which I wore a full slip and bustier to preserve some dignity (dignity, ha; underneath Michelle’s reserve I was a slut waiting to get out). It was a soft yellow and orange pattern, and I had all the accessories to match.

Alex was to meet me at my hotel at 8, so I had to get ready. I began by shaving carefully, twice over in some places to get rid of my shadow. Then I stroked a gentle moisturizer into my skin to soften it up. Finally I took a long, sensuous bubble bath, immersing myself not only into the water but also into my Michelle personality.

I had ordered a glass of champagne for my room, which I sipped as the preparations progressed.

Stepping out, I patted myself dry with a huge fluffy towel, feeling how soft my skin had become in the bath; I was feeling quite feminine. Then I put on my basic foundation, carefully blending into my face and neck to provide a smooth appearance. It looked great!

I followed that with my eye make-up, being creative with colours until my eyes shone. Some lip liner, lipstick and blush completed the picture. I closed my eyes, quickly put on my blonde wig and opened stood smiling back at Michelle’s reflection in the mirror.

“Wow, Michelle, we’re going to have some fun tonight.” I noticed that my voice had unconsciously slipped into Michelle’s softer, more lilting tone. “Now, darling, let’s get dressed.”

I slipped on my lacy orange panties, feeling the cool nylon encase my thighs and then my bum. One thing about dressing like a woman: I had learned to appreciate the softness and silkiness of materials around my body, and get a thrill all over my body. I wasn’t just dependent on having my prick stimulated, as a man is. I’ve learned to enjoy all-over body feelings.

Next I clipped on my matching suspender belt. I’ve always preferred stockings and suspenders to pantyhose, because of the look and because of the feel of those naked three inches on my thighs. Only when I must wear hose, as with a slim dress or skirt, do I opt for them.

Passing my suspender straps through the panties, and re-adjusting that garment lovingly afterwards, I sat down to put on my stockings. They were wonderful – smooth, slippery and coffee-coloured with back seams, which I carefully straightened on the way up. Lastly I clipped the tops of the stockings in place and stood.

I love the feeling of women’s clothes; the fuss, the differences. I’ve never understood why they want things to be more comfortable, more like men’s. I guess it’s because I don’t have to live in them.

Anyway, as I stood and felt the pull of the stockings against the suspender straps, it reminded me to mince my steps and behave like a gentle lady, not like a crass young man. Taking smaller steps, I went over to pick up my ultra-lacy, matching yellow bustier with balconette bra. It was a beauty, self-patterned in softest ivory, and it always made me stop in admiration before putting it on.

I carefully put my arms through it, leaned forward and fastened it behind my back, just like a woman, then adjusted my budding breast inside. I remembered the days when I had to put it on backwards to fit the hook-and-eye clasps together, then pull it around my body. To complete my bust, I fitted the B/C breast forms into my bra cups.

Standing up straight, I sneaked another quick peek at the looking-glass, and there was Michelle, pretty in her matching underthings, smiling broadly back. “you naughty, beautiful thing, you,” I whispered to the vision.

Now, my shoes. I always liked to put these on before my full slip, to get the full effect later. My shoes were yellow slippers with 4″ heels, just high enough to change my gait without much danger of falling over.

I slipped them on, making my feet as comfy as possible in them before buckling the ankle straps. I knew that, no matter how snug they felt at the start of the evening, by later on I would be only too glad to kick them off. I would never again criticize women for that gesture, having endured the pain myself on many occasions!

Now Michelle was ready for the final elements; her slip and her dress. I picked up the white full slip, held it against my body and nearly swooned in pleasure. There is nothing, nothing, for me like the smooth feel of a nylon slip. It reaches me somewhere at the unconscious level, somewhere nothing else can reach.

Then I put on over my head, gathered the bodice prettily over my bra, and wriggled it slowly down around my body. The slip cascaded softly down, whispering past my satin-clad waist, butt and legs, to settle in its place. Wow. What an entrance a slip makes. I dreamed I stopped traffic in my Maidenform slip….

I almost lost control and swooned again when my hand brushed the smooth nexus of the slip over my pantied-butt. Such a feeling of smoothness, of nylon upon nylon, of sheer wonder, I never felt anywhere else. Don’t ask me to explain it; it’s just there, and it’s incredibly powerful.

I took a long look in the mirror, just to admire Michelle, slimmer now in her tight bustier, smoothed shape accentuated by the low and drape of the full slip, her crowning glory of blonde tresses falling around her ears, and her high heels completing the image.

I felt weak for a moment. I was Michelle.

Finally, after the last sip of champagne, I almost reluctantly pulled the chiffon dress over my head and tugged it down around my hips. I can’t describe the sound the chiffon made, sliding over my slip, without becoming emotional. It’s a feeling of peace, of wonder, of happiness which I’ve never felt elsewhere. And after adjusting the dress, I took one last look at myself, because right then there was a light knocking on the door. Alex.

But just for a moment I was entranced again. Michelle stood there, in her yellow chiffon dress and matching shoes, perfectly-proportioned body and slender legs.

She was me. I was her. Wow oh wow.

I quickly spritzed some perfume behind my ears, around my wrists and opened the door. Alex stood there. She was a knockout.

She was wearing a short black cocktail dress with a full skirt and a slim bodice. Matching shoes, jewelry and hair completed the picture. She look fabulous, and despite my Michelle person I had to check my first impulse, because I could feel my erection starting to happen. I concentrated rapidly on keeping my prick soft, and stood aside to let this vision into my room.

But she wasn’t moving. She was standing there, jaw slightly dropped, looking confused and embarrassed. Finally she got some words out.

“Sorry, I was looking for someone else. I’ve got the wrong room. Sorry.” And she began to turn away.

“Alex!” I said urgently, trying not to break out of my Michelle voice. “It’s me, Alex; it’s Michelle … you know, er, Larry.” She stopped. She turned her head to one side, and then a whole different look crossed her face. It was one of amazement. “No!” She cried. “Lar…er.. Michelle! I can’t believe…. You look, well you look fabulous!”

“So do you my dear sweet girl,” I managed to get out. “Now come on in.” Alex bounded through the door and into my arms and we hugged like two excited schoolgirls. “We’re going to have so much fun!” she squealed.

“Yes we are, and a lot more besides,” I breathed, holding her tenderly at arms’ length. Then I kissed her tenderly, to avoid mussing our makeup.

So out we went, two girls having a ball on the town. We went to dinner, where we flirted shamelessly with every guy, then dancing. We danced with others and even danced together; it was in one of those relaxed bars where no-one minds if two chicks dance together, But then Alex put her painted lips next to my ear. “I know the right place to end tonight at,” she whispered. “It’s a lesbian bar. Let’s go.”

It was wonderful there. We walked in, hand in hand, and nobody batted a false eyelash. In fact, we were par for the course. So we danced close, kissed hungrily on the floor, and shamelessly groped each other in the dark corner. I even saw two patrons nudge each other and smile at our obvious passion.

Being touched in dress was a fantastic experience. Wearing a dress, I always feel so vulnerable, with my legs exposed, and my dress threatening to fly up or ride up and expose my panties and suspenders. I really understand how women feel out on a windy day.

Alex’s hands were everywhere on me – and I suppose, so were mine on her. The feel of her hands through my dress and slip was soothing, then interesting, then urgent. Later, as we sat together in the gloom, she reached playfully under my dress, and it became electric.

I was amazed at how quickly she was able to find the naked skin of my thighs, and what a jolt that was. It was like being undressed in an instant. Her fingers flicked at my penis, then slid over to threaten my puckered butt, while I gasped at the sensation and kissed her neck and ears.

“See how it feels for girls yet, Michelle?” she asked playfully. “Oh yes, yes,” I sighed in reply. “I might faint with pleasure, and you haven’t even touched me properly yet.”

“That’s why girls get annoyed when men go too fast, darling. We can enjoy so much for so long, at so many levels, that we want to take it slow. I hope you see that now. Slow hands, remember. “

“Yes, yes, I do. Now I can fully understand.”

“Keep enjoying it; keep relaxing, because the big stuff is still to come – and I mean that literally. Why don’t we have one more dance and then go?”

The music was slow and sexy, and we clung to each other as we danced. Interestingly, I was concentrating so hard on keeping my prick soft, that it seemed to work, to an extent, that is. I was Michelle for the evening, I kept saying to myself, and girls don’t get hard-ons. Girls operate on many more stimuli than that.

So we danced, and rubbed on each other, my dress and slip sliding across her body, our bodies and breasts pressing hungrily, then brushing, separating, and coming together again. I could feel my stockings slipping against hers, and I thought I was close to heaven. Could this be an angel’s feeling, I thought.

After the song was over, we went to the ladies room and touched up our makeup, frizzed out our hair, and left. We were going back to my hotel room.

Letting ourselves in, we stood for a long moment at the door, in each other’s arms, admiring each other and what we’d already done that night. Then Alex came up to me, putting her arms around my neck and kissed me deeply, hungrily. I responded, letting the moment take me away, feeling myself falling into her arms, falling into love – and least into gentle, easy lust.

“Now let’s get these dresses off,” she said. “I know you want to keep your undies on.” She began to help me remove my chiffon dress, now damp with the evening’s sweet perspiration. In a moment I stood before her, clad only in my slip and lingerie. “Me next'” she said.

I slowly undid Alex’s bodice, unveiling her tender breasts, for she wore no bra, which I kissed and caressed slowly as she sighed into my ear. “You really do make love like a woman,” she whispered. “So soft, so gentle; not like a rough man.” It was a wonderful compliment. I got her dress off, then her shoes, leaving her in her black satin panties.

“Let’s go to bed, I have the stuff for you,” she said. As I walked over to the bed, she was reaching into her handbag. She produced a medium-sized strap-on dildo and some lube. “Now let’s see if we can give you the full feminine experience.”

We kissed, we cuddled, she moistened my butt, then slowly entered me as she kissed me some more. It was an electrifying experience; the size of the dildo meant little or no pain, which anyway turned to pleasure as she pumped me in and out. Soon I was moaning and so was she.

“Alex, I have to come,” I stammered. “I’ve been holding it back all night.”

“All right, sweetheart, let yourself go, I’m coming too.” And we climaxed long and lovingly together.

Then, just like a woman, I lay quietly in her arms for an hour, until we both felt good enough to do it all over again.

All in all, my first night as a woman was a resounding success. I can’t wait for my next.

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