Abstract from: Passing on a Date: A Crossdressing Adventure

Below are two chapters from Alan’s Book. They are pages 21-30 of a 120-page book that is available on Amazon in kindle and paperback editions.

As the book opens we learn that Cheryl Ann “Cassie” Sanders has been dressing since childhood and has long been able to pass as a woman at restaurants, in department store fitting rooms, in hotel bars and the like. But never before for more than a few hours at a time.

She has been planning this greatest adventure for months: a three day weekend in Chicago as a woman. She expected shopping, museums, nice dinners out.

What she didn’t expect was on the train ride to Chicago being seated in the dining car with a handsome man. What she didn’t expect was successfully lingering over a three-hour lunch with him on the train. What she didn’t expect was that he would ask her out to dinner while she was in Chicago. What she didn’t expect was the first date–and the second date–and the incredible, amazing things that would happen to her on those dates and elsewhere that weekend. What she didn’t expect was romance. What she didn’t expect was passion.

Here, she starts getting ready by the first date.

Getting Ready for the First Date

I followed the bellman into the hotel and checked in. I had long had a credit card in my girl name, and as an experienced Photoshopper, I had, a year earlier, created and laminated an altered Indiana driver’s license out of a scan of my own driver’s license, changing only the photo and the name. The clerk didn’t notice a thing, and I checked in, signing Cheryl Ann Sanders for the first time in my life.

My weekend had just begun.

My room was light and airy and surprisingly large. A big double bed. A dresser in antique white. An overstuffed couch with a cocktail table in front of it. A pink bathroom and separate small dressing room with a giant mirror and good lighting over an expansive vanity, a red plush seat before it.

I unpacked my skirts and dresses and lingerie and other totally girly things. Girly things were the only things I had with me. I undressed and used depilatory on my face and body again, then showered. I threw on my darling, if a bit frilly, Geisha robe and rested on the couch for a while. But I was too anxious to relax, so I soon began getting ready for my first date with a man.

First, I took a long bubble bath, a leisurely laze in warm, soapy water laced with fragrant, skin softening bath oils. Gentle patting with a large fluffy bath towel came next and then a liberal dusting with sweet smelling after bath powder all over my body, the pink puff tickling my skin.

A few minutes of relaxation on the bed after my bath, and I began to dress. Moving slowly, sensuously, gracefully, I reformed my female body as I had that morning. I changed the color of my toenail polish to dusty pink and put on and polished new fingernails to match. I wore sheer pantyhose.

I did my face next, once again paying special attention to highlight the apples of my cheeks. I wore much more dramatic eye makeup. Three shades of grey eye shadow blended from darker at my lash line to almost invisible at my brow line. Brow powder made my brows darker and arched. Unlike that morning, I used black eyeliner, not only at my top and bottom lash lines, but also just a bit cat-like at the outer corners of my eyes. Heavy, black mascara on both my top and bottom lashes completed a dark sultry look to my eyes. I put cheek color under my cheekbones and blended all the way back to my ears. I shaped my lips with brushes, the filled them in with a dusty pink to match my nails. A gloss helped make my lips look full and moist. I pursed them into a kissing shape and smiled at how they looked in the mirror.

My face was done. In my pretty underwear and pantyhose, I padded over to the closet and took out one of my favorite dresses. Black, sleeveless, tight to my full breasts and slim body down to my hips, it then flared out into a short A-line skirt that came only to several inches above my knees. It left my arms and shoulders and most of my legs uncovered. Below my shaved armpits, the arm holes scooped down low, almost to the side straps of my black bra, making the top look almost like a tight tank top. The overall impression was mostly of a lot of smooth, pale skin emerging from a little black dress.

I put on dressy high heels, thin silver straps crossed at my toes and slung behind my heels. The thin heels were higher than medium, but not dramatically spiky, just as evening fashion dictated. Most of my jewelry and my little clutch bag with chain handle strap would be silver also.

I took the thin white gold chain of my delicate necklace by its ends and reached back to fix the clasp. A single diamond drop hung from its center, twinkling against the hollow at the base of my neck. Several loose silver chains and silver bead bracelets went on my left arm, sliding up and down to my wrist or back onto my forearm with the motion of my right hand. On my right arm, I wore a favorite bracelet made of alternating fine crystal and silver beads. It also tended to slip back to my forearm when my hand was raised. I wore several rings of cast silver with carved flower motifs, and, on the ring finger of my left hand, a ring that featured a carved flower in red carnelian. As a boy, I wore a little gold bead stud in one earlobe, but both lobes were pierced, and, for my date, I put in my diamond studs. I loved the way they sparkled!

I wore the same wig as I had all day but teased it to make it very full and feathery around my face. I had to keep brushing back a couple of little tendrils that fell around my eyes but liked that feeling of having to brush them back occasionally.

Although my heels were high, after years of practice, I walked easily on them over to the full length mirror, moving my right hand ever so slightly forward with my left foot, my left hand forward with my right foot, both hands several inches away from my body, my fingers in a relaxed curve, swinging comfortably and naturally with my gait.

A pretty girl looked back at me from my mirror, a girl beaming in excitement, her smile enlivening her whole face. In the mirror was a girl ready to go out on a date: a Chicago spring evening on the town with a man. Slim, graceful, extremely feminine in her little black dress, I had to look down at myself, at my body, down at my breasts and dress tight to my torso, passed the short, flared skirt, down past my hem to my legs, to my pink toenails in my strappy high heels. I had to look down directly at myself to know to the depth of my soul that I was that girl in that dress in that mirror.

The First Date

I was that girl, and I was ready to be her on that date with all my heart.

The phone rang. Kenneth was downstairs in the lobby waiting for me. My heart was racing. A date, as a woman, going out with a man. I put on some perfume, picked up my room key and bag and walked slowly to the door, thinking about the way my hips were moving with each step, keeping it minimal, natural. I hesitated for just a moment before opening the door and walking out. I took the elevator and hit the lobby button.

When I got off the elevator, I immediately saw Kenneth across the lobby. He saw me too and took bold strides through the lobby crowd towards me. My left hand clutched my bag tightly to my body just below my left breast. My right hand fingered the material of my skirt nervously.

I could hardly breath. My eyes flicked nervously around the room. I could see several people in the lobby watching a handsome man walk over to his date.

Kenneth reached me, took my free hand in his, and stood back a step. I watched his eyes move over me, my face, my hair, my bare shoulders, my breasts and body, my clothes. As his eyes moved down my legs, I snuck a nervous swallow. I still could hardly breathe. He looked up into my eyes and smiled.

“Your dress is beautiful,” he said. “You look wonderful.”

“Thank you. You’ll make me blush,” I answered softly. “You look pretty swell all dressed up yourself.”

I meant what I said. He was stunning in his black blazer, fitted white shirt, and silver tie. His grey slacks had knife-sharp creases and his black shoes a bright shine. I noticed again his pale blue electric eyes as a contrast to his tanned skin. I had to remember to ask him how he could have so much a tan so early in the spring.

His hand felt big and slightly rough holding mine. It made my own hand with my long pink fingernails feel small and soft in his. I had to tilt my head back to look up into his eyes.

As we turned, I saw us full length in the closed, mirrored elevators doors and froze for a moment. I reached and brushed a tendril of my hair out of my eyes, not because it really needed it, but because I had to internalize again that the girl of that couple in the mirror was me. I smiled at what I saw, and the face of the young woman in the pretty sleeveless cocktail dress came alive.

“I hope you don’t mind walking. The evening is beautiful, and the restaurant is only a few blocks from here. I’ve already put my car in a lot.”

“No, not at all. I’d love a walk.”

Several people in the lobby smiled at us as we crossed the lobby. I could smell my perfume. I could feel my breasts jiggle just slightly. I could feel the nylon stretched over the insides of my thighs brush against each other as we walked. I remembered that old trick: to walk like I was proud of my breasts; it helped me to remember to keep my posture, to keep my shoulders back, to walk from my hips, not my shoulders. Keeping my feet close to an imaginary center line in front of me with each step, I let my hips shift slightly with my gait and could feel the skirt of my little black dress sway back and forth on my legs.

As Kenneth put his hand on my back to help guide me through the lobby crowd, I looked back up at him and smiled happily. He smiled back, and I felt more feminine than I had ever felt in my life. I kept my posture, proud of my breasts, of my shape, of my striking dress, of my smile, of being a girl on her way out to dinner with a man. I felt desirable. I felt that every man in that lobby wished that he were Kenneth. I felt wonderful!

When we reached the door, Kenneth, in a smooth, practiced motion, reached out ahead and held it open for me. My high heel shoe stepped over the threshold and clicked distinctly on the sidewalk. I stepped out into the warm evening with Kenneth beside me. I was on a date as a woman with a man.

Many other couples were walking in the warm Friday evening. My date was as handsome as any man I saw. And I could sense that he was proud to have me walking beside him.

Kenneth took my hand as we were walking. I still could hardly believe it: I was walking down the street in a pretty dress with a man holding my hand. The slight breeze ruffled my hair so that it tickled my bare white shoulders. As we waited for one light to change, I shifted my hip, placing all my weight on my left foot, crossing my right foot behind my left foot, my legs close together, my right foot light in my shoe for several seconds with only the toe part barely touching the sidewalk. Then as the light was to change, I brought it back to be next to my left and evened my weight as we stepped off the curb. At another light, I looked down at our feet as we stood next to each other, Kenneth in his heavy black dress shoes, me in my stockings and high heels with thin straps that barely covered my feet and showed off my long toes with their dusty pink nails.

Kenneth and I talked easily the whole time. One time, Kenneth refused a vendor trying to sell some tacky flowers, “for the pretty lady.” Another time, another couple stopped us to ask directions; and as Kenneth told him how to go, the man stood sideways to Kenneth, listening to him, but looking entirely at me the whole time. The walk was delightful and gave me even more confidence.

The restaurant was small, elegant, and French. The Captain held my chair for me as I sat, smoothing my skirt under me, keeping my knees together as I turned into the table. I wasn’t sure what to order, and Kenneth helped me decide. Just the simple experience of hearing him refer to me with feminine pronouns seemed especially nice somehow: “The lady will have…” “Give her…” “I think she’ll like…”

Without effort, I found myself being graceful with my knife and fork, as I reached for my wine glass, as I gestured and talked, as I cocked my head and smiled at a small compliment.

Everything was delicious, but I didn’t eat an awfully lot. Kenneth seemed not to notice that all my plates were taken away half full. Similarly, I only sipped at the delicious wine. I was already giddy with the excitement of the evening and where I was and what I was doing; and I was being careful not to drink too much.

The conversation was lively and less personal even than it had been over lunch earlier. Instead we talked about politics, books, music, movies, New York City, even sports teams. It turned out that we had voted for the same man for President and for pretty much the same reason. We disagreed vehemently about one book and argued some more over one movie but were generally in more accord. I found that my perspective on several subjects was in some ways different than my usual … and realized that I was totally talking and thinking as a young woman without effort, with even realizing it at first … and that, in fact, my perspective on some things was different as a woman.

At one point, talking about a female character who had been jilted cruelly in a movie that we had both seen, I found myself saying, “Oh, you just can’t understand what she was feeling at that moment the same way I can.” I blushed at the thought of what I had just said, but Kenneth had already moved on to something else and hadn’t noticed.

At another point, after we finished our main courses and awaited dessert, I let him hold forth for a long time on the importance of print journalism to society. I had my elbows on the table, my folded fingers abutting, my chin resting on my knuckles; I was just looking at him, so handsome, listening to him, so impassioned. I couldn’t suppress my smile. I couldn’t suppress what I was feeling about him, about me, about me and him.

Over dessert and coffee, Kenneth reached across the table and took my hands in his. “What a wonderful dinner this has been,” he said. “I don’t want the evening to end yet. Are you up to a bit more walking? It’s not 11:00 yet.”

“Sure,” I said. “Just let me freshen up in the Ladies’ Room.”

I went there while Kenneth paid the check. I smiled to myself as I walked through the door with the black silhouette of a woman in a Marie Antoinette dress. I sat at a lovely vanity in the ornate outer room freshening my face. Women came in and out, lifting skirts to straighten slips, sitting all around me working on their hair and faces. No one paid me any special attention.

Kenneth met me as I came out of the Women’s Room and escorted me from the restaurant as I thanked him for dinner. The Captain gave us a smile and wished us a pleasant evening as we left.

We walked for over half an hour. For much of the time, I held my little silver bag by its chain bunched in my hand, swinging it rhythmically against my hem as we walked and talked. For much of the time, Kenneth held my other hand in his. When I looked down at our hands, I could just see my long pink fingernails poking out from Kenneth’s much larger, enveloping hand gently holding mine.

Several times as we waited for a light at an intersection to change, Kenneth let go of my hand and draped his arm across the back of my mostly bare shoulders, holding my far shoulder in his hand, pulling me in closer to him against the air that was turning colder. As a girl, being that close to a man felt only natural. Once even, as we waited for a light in that way, I hesitated and then leaned my head down against his shoulder, looking up sideways and a bit shyly through my lashes. He smiled down at me and kissed my forehead. I was suddenly living what was a fairytale world of make-believe for me, but that was, in fact, happening to me.

As we circled back towards the hotel, we passed a small dance club. He asked if I would like to go in for a last drink and a dance before going back. I was unsure because I had never danced as a girl, but I didn’t want the evening to end … ever!

He ordered a scotch and soda. I had an Aperol Spritzer. We sat at our little table, drinking our drinks, holding our left hands across the table and watching the dancers. I studied how the girls moved and was confident that I could do it as well.

We danced. We were much more formally dressed than most of the patrons, but Kenneth soon had his tie and jacket off and his shirt unbuttoned down a few buttons. I soon kicked off my heels and danced in my stockings.

My breasts bounced and moved under my dress. My hips swayed to the music. My skirt twirled and swung around my thighs. My hair brushed my neck and shoulders. I felt myself to be just like, just another of the girls on that dance floor. The lights and the music and my soul vibrated in excitement, in pure joy.

Suddenly, in the middle of the dance floor Kenneth clasped his hands around the small of my back. Instinctively, I immediately reached up and clasped my hands behind his neck, forcing me to arch my back a bit. I tilted my head back to look up at him until our eyes locked. We swayed to the music, my body closer than it had ever been to a man.

Kenneth leaned over and kissed me gently on my lips. It startled me as I realized what was happening. But I didn’t pull away. It wasn’t simply something that happened, something that I had let happen; it was more considered than that: I knew I had chosen to let it happen. It was as if I were experimenting–experimenting with myself–testing, learning for myself, what my feelings would be.

He kissed me again. Then again. And yet again lightly, as if tasting my lips. And then longer and firmer, with the first inkling of his tongue beginning to explore my lips and starting to push through them.

I had never been kissed by a man before, never been kissed as a woman. I couldn’t breathe with my confused feelings. It felt strange, but nice. No, okay–almost immediately it felt natural, wonderful, exciting, right. By that time that night, I had felt so much a girl anyway. A girl on a date with a man. It felt only that it was natural, normal, that I be kissed by Kenneth. And I liked it.

Like any woman, I found myself arching my back more, pressing my soft body against his as we slowly moved to the music and kissed. I felt my breasts pressed flat against the thin white material of his shirt, against his chest, loving the way my two breasts felt caught between us, how they felt pressed against Kenneth’s muscular body. Then–at my belly–I felt– I knew what I was feeling. It was the ridge of Kenneth’s penis growing erect under his slacks as he pressed against me, becoming partially erect caught between us–against me, against my own body in my pretty dress and underwear, against me, the girl in his arms. It was me. I was making that happen to him. I was the girl in his arms.

Still in beat to the music, our lips, our mouths locked in a serious kiss, people dancing all around us, I let my belly slide back and forth over the ridge I could feel against me. Unbidden, my mind imagined it, pictured his erect penis hidden down there in his pants, his erection caught between us. I found myself thinking about it, this thing that I was doing to him, thinking that, that it would be cool to see his erection, just one time–to see with my own eyes what I’ve done to him–just for a moment or two, no longer-or even, maybe, to touch it for a second, to discover with my fingertips what it would feel like, this thing that I have done to him.

The song ended. The kiss broke. We stumbled back to our table together. We sat and looked at each other with what seemed to be a little mutual embarrassment.

“We got a little carried away out there,” I said to break the ice.

“Umhhh,” he hummed and smiled.

I was in anguish with the understanding that I couldn’t let things go any further at all and said, “Perhaps we’d better go.”

“But can’t I see you again? I can’t just let it end like this.”

He went on, “Listen, my company is having a formal dinner-dance tomorrow evening that I must attend. Won’t you come as my date? I’d be so proud to have you there with me.”

“Another date? Another date!” filled my mind. I was hesitant, afraid of pushing my luck. But I knew, I had to admit to myself, how much I wanted to see Kenneth again and do this again before this weekend was over.

It was a very short pause before I said, “This has been so much fine, so nice tonight being out with you. Okay, sure, let’s do it. I’d be delighted to go with you tomorrow, Kenneth.

“How should I dress? When should I be ready?”

Kenneth told me the time he would have to pick me up and that it was a black-tie affair and let me figure out what I should wear from there. He never let go of my hand all the way back to the hotel. He walked me to my elevator, gave me a soft kiss on the lips, said goodnight, and walked away.

I had to lean against the wall of the elevator I was so drained by the day and the evening. The feeling of Kenneth’s kiss lingered on my lips, and I hugged my own female body. As soon as I walked into my room, I went directly to the full-length mirror and just stood there staring at myself. I had done it. I had passed on a date.

I knew I was a boy. I knew my breasts were false. I knew I had a penis hidden down there under my womanly parts. But there was absolutely nothing in the mirror to hint at it. And nothing in the evening. In the mirror, the slim legs, the tight dress, the bare shoulders, the tiny waist, the round mounds of breasts, the shoes, the face, the hair all said “girl.”

I stood with my arms down at my sides looking at myself in the mirror, looking at an attractive young woman in the mirror, a young woman that had learned, that now knew she could be passionate, that now knew how passionate she could be as a woman, a young woman who on that dance floor had wanted Kenneth like any woman would, who dreamed of Kenneth’s body locked with hers, with mine, with me.

“Stop! That, of course, is an impossibility,” I thought. “Can’t have that. But, what can she, what can I, have?”

Passing on a Date: A Crossdressing Adventure is available through Amazon.

Tags: crossdressing, featured, fiction

Category: Fiction