tagTranssexuals & CrossdressersA New York City Romance

A New York City Romance



Friday afternoon, I finished my last class, grabbed my backpack, and ran for the bus. It pulled up as I reached the stop. "Return ticket to the city," I said, paid, and took a seat near the back of the bus. Two hours later the bus was heading under the Lincoln Tunnel. The first view of the New York skyline was always a thrill, and as the road pitched up and we exited the tunnel, I had the sensation of my life opening up again.

Not that this was going to be such an exciting evening, but, hey, it was surely better than another night at home in far western New Jersey. I was in the city for my big sister's twenty-fifth birthday party. Her friends had hired a club downtown for the party, and although they were all very nice, they were mostly medical students and doctors. Maybe I'm misremembering, but Sharon seemed to have been more fun before she went to medical school. Still, looking at it from society's perspective, I suppose it's a good thing that doctors aren't so wild and crazy.

I was going to stay with Susie, Sharon's best friend from high school. Susie wasn't going to be a doctor. Nor a lawyer, nor an MBA, nor anything mainstream. She taught dance at a school in Manhattan and wrote funny novels about dance and sex. She lived in an apartment on the west side with a couch for a guest to sleep on. I loved her apartment, but that's because I loved her. Susie and I had a history. She was the first girl to touch my cock, and hers was the first pussy I had licked. That's all we had done. Anything more would be inappropriate, she said, because she was my sister's best friend and so much older than me. "Only six years!" I would always protest. "Yes, and that means you're still a baby," she would respond. But I didn't mind too much because she could do amazing things with her fingers and I loved running my tongue slowly along the length of her pussy and hearing her moan.

But ours was a secret history. Not even my sister -- especially not my sister! -- knew about us. And since Susie had moved to the city I didn't see her so often, even though we texted and emailed almost every day. I was closer to her than Sharon. I would never have asked Sharon for advice about girls, but Susie was always full of wisdom and commentary.

It was getting dark as I walked from the bus station to her apartment. She opened the door, and kissed me on the cheek as I walked in. "How are you, sweetie?" she asked. "Good," I said, looking around her neat and tidy apartment. "So are you ready to party?" she asked. I rolled my eyes. "Yes, I know what you mean," she said. "Still, we're going for Sharon, so we've got to pretend that we're having the time of our lives. And maybe you can meet a cute medical student," she added.

"Are there such things?" I asked.

"I met one once," she said. "Sharon set me up with him. He was cute. Boring but cute. I used to fuck him just to get him to shut up about medical school."

"That I doubt," I said.

"Ok, you know me too well. I fucked him because he had a great body and a beautiful cock. How about that?"

"Sounds more likely," I said, returning her smile.

"I figured we'd head down to the party at about nine," she said. "Ant later and they'll all be heading home. So let's have a drink and then we can change into our party clothes."

Uh oh! I thought. Susie saw the look on my face. "Is there a problem, baby boy?" she asked.

"I forgot my bag," I said.

She looked at the bag I had dropped on the couch. She pointed at it. "It's there."

"No, the one with my clothes. I left it in the locker at college and forgot it in my rush for the bus."

"Problemo," she said, looking at my rumpled t-shirt and worn jeans. "Sharon will be mightily pissed if you turn up like that."

I shrugged my shoulders. "So what can I do?"

"Don't know," she said. "Let's have a drink. I'm more creative when I've had a drink."

She poured two glasses of white wine and we sat at each end of the couch facing each other. "Do you have any of your boyfriends' clothes around?"

"No. Nothing suitable for a party at a club, anyway."

I was getting desperate, imagining my sister's anger. "How about you then. Do you have any slacks or pants that I could wear?"

She laughed. "Have you ever seen me in slacks?" She pronounced the word as though it described something obscene. "All I have are jeans and workout clothes. How about some dance tights? That's it! Go as a dancer and tell Sharon you thought it was a fancy dress party."

"You're not helping," I said glumly.

Susie took another mouthful of wine. "So how about this then? If you want to borrow my clothes, let me dress you up like I used to. Some makeup, a cute white blouse and a short skirt, you'll be a sensation."

I haven't mentioned our dress up games. Maybe it's because Susie didn't have any sisters of her own, but there was a time when the only game she wanted to play with me was dressing me up. I didn't mind because what came before dressing up was undressing, and there was little I liked more than being naked in front of her, and our games usually ended with her hand on my cock and my mouth on her pussy. It didn't much matter to me that while that was happening I was wearing dress and girl's underwear and had my face and hair made up, and that she called me Stephanie rather than Stefan.

"No," I said. "I'm not going to Sharon's party as Stephanie."

"But Stephanie is so pretty. You'll have so much fun."

The fact is that she did make me look very pretty. I used to marvel at how she transformed me from a teenage boy to an attractive girl. But even so, it wasn't going to happen tonight.

We sat on the couch looking at each other, not speaking.

Susie poured some more wine for us, and we continued sitting silently.

"Please," she said.

"No," I replied.

"Please," she repeated.


"But please!" she said, drawing out the pleeaase to a long thin whine.

This is always how it went. Susie got an idea in her head and would ask and ask and ask until she wore me down.

"Why not," she asked.

"Because my sister will hate me," I said.

"But I'll explain," she said. "She'll blame it on me. And you'll look so cute, she'll be surprised and not angry."


"But it'll be so much fun?"

"Everyone will think I'm crazy."

"But they're medical students! They'll love that! You'll be the star of the party."


"Ok, then. I'll suck your cock if you do it."

That made a difference, very definitely. I wasn't a total innocent, but if truth be told I hadn't had many girlfriends, and my success rate at persuading them to touch my cock was pretty low. And none had accepted my invitation to suck it.

Susie noticed the change in my expression. "So, baby boy, how about it? Your cock sucked for the very first time and I dress you for the party. Do we have a deal?"

"You'll tell everyone that me dressing up was your idea?"


"And that I didn't want to do it, but had no other option?"


"And that you got me a little drunk before I agreed?"

"Totally plastered, if you want."

"Ok," I said.

"Ok, what?" she asked.

"Ok, we've got a deal. You dress me up and you'll suck my cock."

"Deal," she said. "Now get naked."

That's the bit I liked of course. I kicked off my sneakers, pulled my t-shirt over my head, and undid my belt and let my pants fall to my feet. Susie sat on the couch looking at me. "Baby boy, you have such a lovely body," she said. She leaned forward and cupped her hand around my balls, and my cock stirred in response.

"And I love your cock. It's so pretty, so cute, so delicate." She took my cock in her other hand, and gently pulled me towards her. She leaned forward and took my cock in her mouth. It hardened as she sucked it, gently caressing it with her tongue. Her hand stroked my shaft, masturbating me as she sucked. My eyes closed with the intensity of the pleasure. So this was what it was like to have my cock sucked. It was heaven. Beyond heaven. I was lost to her touch. I imagined her mouth drawing up my cum from deep inside me, coaxing it into my cock, slowly raising it until it was ready to spurt out through her lips into her mouth. I wanted so much to fill her mouth, to show her how much cum I could produce for her as though that were a measure of my gratitude.

I came, shooting hard into Susie's mouth. She sucked me gently and stroked my shaft as the tension in my body relaxed. Then she drew me down on top of her on the couch, and she held me close to her, my head cradled in her shoulder, and she stroked my hair, and kissed me softly. "Was that as good as you imagined, baby?" she asked.

"Yes," I said. "It was incredible. It was so intense."

"I'm so glad I was the first to do it you, my baby brother."

"Me too. I'm so happy it was you."

We lay together for a long time, me so happy and content in her arms. Then, after long minutes, she asked softly, "Are you ready for me to dress you?"

"You can do anything you want to me."

She kissed me again, and stood up. She pulled me to my feet. "Come. Into my bedroom, little boy."

After the job Susie's mouth did on my cock, and after the couple of glasses of wine, I was no longer very concerned about Sharon's party. So what if I turned up as Stephanie? So what if Sharon is angry? So what if everyone there thinks I'm weird? I can live with all that because Susie just sucked my cock!

She stood looking at her closet. "So what might my little Stephanie wear tonight?" she asked.

"Nothing too slutty," I said, remembering some of the outfits she had dressed me in before.

"What's wrong with slutty?" she asked. "You've just had your cock sucked by your surrogate older sister. Don't you feel a little bit slutty?"

"Maybe. But only a little bit," I said. "Maybe you should suck me some more to make me feel more slutty."

"Good try, baby brother, but the deal was one time only."

"But it was sooo good," I pleaded.

"Yes, and that's why I can now dress you as I want. Lie on the bed."

I lay down. Susie took some white cotton panties from her closet and placed them over my cock. Then a black leather miniskirt, and placed that over my legs as though I were wearing it. Then she placed a white camisole and a white silk blouse over my chest. "That's pretty," she said. "Classic, but the leather gives a hint of sluttiness. Sit up," she instructed.

I sat on the edge of the bed and Susie made up my face. She was truly an artist with makeup. After a few minutes she took a step back and looked at me. "That looks right," she said, and took my hand and led me to the mirror. The effect was remarkable. She had swept my long blond hair back over my ears and held it back with a clasp. She had applied eye liner and mascara so that my eyes became the prominent feature of my face. She had applied blush to my cheeks, and a subtle pink to my lips. I looked like a girl made up for her prom. "That is amazing," I said.

"Ok. Try on the clothes," she said.

I pulled on Susie's panties. "They fit ok," she said, "but you can't have this sticking out." She tucked my cock into the panties. "Now the skirt," she said. It was tight, but I could get it over my hips. She stepped back and looked at me. "I don't know," she said. "It's very cute, but it's quite revealing. If you get hard, it will be obvious to everyone."

"They're medical students," I said. "How hard am I likely to get?"

"Good point," she replied. "But if for any odd reason you start getting hard, sit down quickly."

Then the camisole and the blouse. "So how many buttons do we leave undone?" she asked? "Too many, and it's apparent you don't have any boobs. Too few, and it looks as though you're frigid."

"Let's do frigid," I said, and she buttoned all but one of them.

"So my dearest Stephanie, we're done," she said, leading me to the mirror again. I stood there entranced. The skirt reached half way down my thighs and the blouse pulled tightly around my slim waist. Susie stood behind me. "And the best of all," she said, "is this." She touched my ass. I turned my head around to see the reflection of my ass in the mirror. The leather enfolded it tightly, accentuating its curve. "No-one seeing that ass will have any doubts that you're a girl," she said.

"Now get out," Susie said. "I have to change."

"But I want to watch," I pleaded.

"And get hard? And start dribbling cum in your panties and down your legs? No. Out."

"You're no fun," I said.

"That's not what you said when I was sucking your cock," she replied.

"Well, ok, but it's not fair to suck a boy's cock then deny him the pleasure of seeing you undress."


I left. Susie came out a few minutes later in a short white close-fitting dress. "What do you think?" she asked. "Amazing," I said, and I meant it. Susie was beautiful, and the dress accentuated her delicious body.

"Shoes," she said. "I've forgotten shoes." She went back into her bedroom and came out with some sandals. "Not perfect," she said, handing them to me, "but all my other shoes will be too small." I put them on, and they felt comfortable enough, and we went down to the street to flag a cab.


Standing on the curb waiting for a cab felt like one of those dreams where you're walking down the street naked. I felt the cool breeze on my bare legs, and I imagined that everyone was looking at me, knowing I was really a boy. Susie sensed my anxiety, and put her arm through mine. "You look so feminine, sweetie. No-one could guess that you've got a pretty little cock under that skirt."

She laughed as my skirt lifted up when I sat down in the back of the cab. "Two things to remember," she said. "First, when you sit down, smooth your skirt over your ass so it doesn't hike up like that. Second, keep your knees together when you sit."

I closed my legs. When the cab arrived at the club, I copied how Susie exited. Back on the street, I breathed deeply, anticipating my sister's explosion at seeing me. "Why don't I go in and explain it to her first?" Susie said. "What, and leave me alone on the street?" I asked, looking around nervously. So we went in together. It was dark inside, and the music was loud, and no-one paid any attention to me as we walked in. A few friends greeted Susie, but even people I knew didn't seem to notice me.

Susie pointed to where Sharon was dancing with her boyfriend. "Wait here," she said. She walked over to Sharon, and kissed her cheek in greeting, then spoke something in her ear. I could see Sharon turn to Susie with an incredulous expression and her mouth form a loud "What!" in Susie's ear. Susie said some more, then pointed in my direction. Sharon looked to where I was standing and Susie took her arm to lead her to me.

Sharon stood looking at me with an odd expression on her face, anger mixed with bemusement. "Stefan?" she asked. I nodded, unable to meet her eyes. "I'm sorry," I murmured, I forgot my . . ." My voice trailed off in my embarrassment.

"You look so beautiful!" she said, her expression softening. "I wouldn't have recognized you at all." She leaned forward and kissed my cheek. "It's just as if I have a little sister. How wonderful!"

She took my hand. "Come and see my friends. They'll be amazed." She led me to the table where she had been sitting with some of her friends. I recognized most of them as I walked up to the table. We stood by the table: Sharon, Susie and me. "I want you to meet my little sister, Stephanie," she announced. They all looked at me, surprised. "Your sister?" one asked. "When did you get a sister?"

"Just recently," Sharon said. "Isn't she cute?"

Then one of her friends cottoned on. "Stefan!" she said. "That's Stefan!"

Sharon nodded. I blushed. "That's amazing," her friend said. "He does look like your sister."

"You can thank Susie for that," Sharon said. "He forgot his party clothes and Susie dressed him up as my sister."

Her friends seemed to accept that as a reasonable explanation of why I was dressed as a girl, or perhaps were too polite to ask more. Either way I didn't much mind. I sat down at the table next to Susie with a sigh of relief.

A steady stream of Sharon's friends came over to the table to wish her a happy birthday. One of them noticed Susie at the table, and she stood up to kiss him as a greeting. He was tall and slim, and even in the semi-darkness I could see he was good-looking. Susie turned towards me. "Daniel," she said, "this is Stephanie, Sharon's little sister."

"Hi Daniel," I said quietly.

"Hi Stephanie," he said. "I didn't know that Sharon had a sister."

"Stephanie doesn't come into the city very often," Susie said.

"I'm glad you decided to come in for the party, then," he said. Then he added, somewhat hesitantly, "perhaps you'd like to dance?"

I must have seemed half-witted because I felt my face became quite blank. But Susie and the others were keen that I accept. "Yes, Stephanie. Go dance," Susie said to general agreement. I managed to pull myself together as far as to shake my head, and my mouth managed to form the word "no," even though no sound came out. "Yes, go on," someone said. "She's very shy," Susie said to Daniel to explain my reluctance. "Come on Stephanie," she said to me, taking my hand and pulling me up from my chair. "It'll be fun."

I should have resisted and tried to explain the joke to Daniel, but rather than embarrass him, I let her pull me up. I stood next to Daniel, at a loss as to what I was to do next. "Go on, go dance," Susie said, patting me gently on the ass to move me towards the dance floor. I followed Daniel, hearing the enthusiastic cheers from the table behind.

We started dancing. At least, that's what I was pretending to do. I had no idea how to dance like a girl. Daniel must have regretted asking me, for I was moving like I was being jerked by puppet strings, with an expression of panic on my face, quite unable to look him in the face. I could sense that the cheers from the table had turned into laughs. And that made me angry. Not for myself, but for Daniel. He seemed like a nice guy, and I didn't want the joke to go any further than it had to. Maybe I can get away with it, I thought. Have this dance, then thank him, and go sit down, and he would never know that I wasn't what he thought I was.

My plan, as desperate as it was, made me relax a little, and my movements became less uncoordinated. I moved away from the table, into the crowd of dancers, so we couldn't be seen. I looked around to see how other girls were dancing, and tried to mimic them. And I even managed to catch Daniel's eye and return his smile. He leaned forward so I could hear him. "You dance so well," he said. I laughed, half wanting to reply "You can't have danced with many girls, then," but thought better of it.

So we continued dancing, and as we did I felt the tension leaving, and started enjoying it. It wasn't so hard dancing like a girl, after all, as the difference mainly seemed to come down to a lot more movement of chest and ass. In fact, it was kind of fun, I thought. Maybe this is how boys would move if they weren't so uptight, rather than shuffling from one foot to the other as though they were treading water. And the movement of my clothes against my skin with these more expansive moves was also fun, and I found myself experimenting with how far I could move without my skirt lifting up so far that I would show off my ass.

The excitement of my dancing radiated through me as though emanating from the dance floor, up my bare legs, through my groin, to my chest and arms. I should have stopped then, but, no, I thought, let me play this out more. This was new a new and different thrill. This was the adventure I came to the city to find. My cock started to stir and my ass and groin became a bigger part of my dance. As I moved, my cock rubbed against the fabric of the panties and against the leather of the skirt, the leather caressing it and making it grow. It felt so wonderful. I wanted the dance to continue, the music to get louder and the dancing more frenzied until my excitement grew and grew until it reached its climax.

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byDani-Amande© 10 comments/ 51703 views/ 43 favorites

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