And now I feel like I’m on fire haha. I never thought this would be my life, I grew up just thinking I was a straight guy but an unexpected encounter changed my life and my entire way of thinking. Now here I am on Reddit, venting about my girly horny feels .
I was 18 years old when my sister gave me the Christmas present that would change my life.
A copy of her drivers license.
She had turned 21, and I was insanely jealous of her ability to go out to clubs and bars. And now she was mocking me with that access. With her social life and sex life, of which I had none. And she was likely mocking my thin frame, lack of facial hair, and resemblance to her.
Whatever.
When I got back to school, I tossed it in a sock drawer and forgot about it.
Periodically I’d see it when rummaging around and grumble or pick it up briefly before putting it back. Until one time, one time I decided I would show her.
I started studying up on YouTube. My algorithm switched from how to pick up girls to makeup and fashion tips for cross dressers. I practiced on myself when my roommate wasn’t home, working on subtle, believable makeup styles and my gait in heels. I laughed about how much I looked like my sister, how much this would backfire for her.
Finally, with my clothes and accessories purchased and my skills honed, I decided to take the leap. My roommate was going back home for the weekend, and I would have the place to myself. I stripped down naked and shaved my body smooth. I lathered myself in scented lotion and perfume before sliding into underwear, hose, and finally, a tight little red dress. I did my makeup, a subtle lipstick and eye shadow combo, and attached a wig of medium length dark hair to match my sister’s. I looked in the mirror. She looked back. She smiled…I mean, I smiled.
I snuck out of my apartment complex and hopped on a train. I inwardly still felt like myself, and would find myself forgetting that outwardly I looked femme. Until a breeze blew up my skirt or I walked and remembered I was wearing stilettos.
The train stopped downtown and I got off. I approached the club I had set my eye on. The neon sign glowed, matching the color of the accent lighting inside. Moment of truth. I approached the velvet rope and handed the large bouncer my ID.
He eyed me carefully due to “my” age, going over the details. It felt like an eternity before he spoke.
“There’s no way you’re 5’3”
Fuck. What do I do. Before I could think of what to do, he spoke again.
“Those are some big-ass heels.” Then he stamped my hand and opened the rope. Wow. I was in. All 5’6” of me.
I walked in, admiring the neon glow and hum of music. The throbbing bass and the loud conversations. The laughs and the dancing. I was finally here.
I found a quiet corner of the bar and ordered a vodka tonic. I decided I would people watch and get comfortable with this. Soak it in and enjoy it. And hopefully, I’d find a way to do it again. I was young and straight, but open-minded enough that I didn’t mind cosplaying as Sarah if it meant enjoying adult nightlife. I think.
After a few sips, nature called. I walked down the hallway and realized my predicament. I looked at both doors and decided to enter the ladies room to maintain cover. I felt like I had entered a forbidden oasis, but I did my best to keep my cool as I saw beautiful women everywhere, adjusting themselves and fixing their makeup. I went into a stall, and, realizing I don’t want to be found out. I sat down on the toilet. I felt a bizarre rush of femininity with my skirt hiked up, panties around my ankles and my tinkle being lady-style. I blushed at this realization and washed up and went back to my seat.
It wasn’t long after that when a man sat down next to me and introduced himself. He was older, probably in his 40s, and very conventionally handsome.
“Hey, I’m Darren” he said. “Nice to meet you”
I fumbled on introducing myself, realizing i don’t really have a name. Not today, at least. He kept making small talk and I got a little panicked.
“Hey, so, I’m not a girl” I said awkwardly
He didn’t miss a beat. “Oh, you’re trans? Good for you.” And he went right back to chatting me up. Fuck.
He bought me a drink and I accepted. I admittedly was enjoying the attention. He asked me to dance, and placed his hands on my hips as we moved about the room. I blushed as he looked deep in my eyes.
“You’re what, 21? How long have you been transitioning?”
I giggled a tipsy giggle. I confessed it all. The ID, the plan. He would now know I’m just a boy, a straight boy, and this would all be over. I was turning my carriage into a pumpkin.
He laughed.
“So you got back at your sister by learning how to transform into a woman so you can go to the club?”
I nodded.
“That’s incredible. And I win this deal, because you’re a very beautiful woman”.
What the fuck. I blushed and felt a tingle in my body. I bit my lip.
He kissed me.
A man kissed me. And I kissed back.
Our dancing became more sensual, closer, my body against his. I felt so small, so secure, so…girly.
We made out a little and he put his hand on my ass. This was all feeling like a dream when he asked me if I took the train. I nodded and told him my station.
“We could take the 10:30. I’m West 3rd. Just a couple stations down. Come with me?”
I nodded. We hopped the train and took the quick trip to his stop. We got off, and he took my hand to walk me over the gap. I blushed again. We walked to a beautiful luxury high rise. Darren greeted the doorman as we walked in. I felt like celebrity arm candy, I was overwhelmed.
We took the elevator and he kissed me the whole way up. I smiled and sighed contentedly.
We reached his room, a luxury penthouse the likes of which I’d never seen before. It was large, plush, and the wall facing the balcony was all glass, giving a view of the city skyline. On the balcony was a hot tub. I was blown away.
“Pretty cool, huh?” He asked casually as I sat on the couch.
“Um…I’ll say”
“It’s a nice warm night. Wanna dip in the hot tub?”
“I…sure. But…” I looked down at my dress. He tossed me something. I caught it.
“Should fit you” he said as he took his shirt off
It was a light blue bikini. I blushed at the idea of me in a women’s swimsuit. He leaned in and kissed me before giving my wig a light pull.
“I bet you’re still beautiful without this” he said with a smirk.
I took it off, revealing my hair which was the same color but short.
“Pixie cut, I dig it” we both smiled.
I walked down the hallway to the bathroom and slid the tight dress off my body. I stood in the mirror in just my black thong, matching bralette, and hose. I turned 360 degrees. In a moment of vanity, I understood why he was into me.
I was a pretty hot girl.
I slid off the hose, then the bralette, and finally the thong.
I looked in the mirror.
Without my clothes, I felt stuck somewhere between reality and fantasy. The beautiful bathroom and my makeup kept me in dreamland. My thin, flat-chested body with my male genitalia pulled me back towards everyday life.
I tied on the bikini top to bring back dreamland.
I slid into the scrunchy bottoms which showed a great deal of my ass.
I wrapped myself in a towel and walked out to the balcony, where Darren was already seated in the hot tub.
I walked past him, and stood facing the skyline, soaking in the view. I let the towel drop, giving him a view of my perky backside in the skimpy swimsuit. After a moment, I turned.
“Incredible. But hey, what are we going to call you?”
I smiled and gave a thoughtful expression.
“Tonight? You can call me whatever you want.”
After a moment of consideration Darren said
“I’ve always had a thing for Rachel”
I stood proudly “then let it be so. Tonight I am Rachel”
“Hop in, Rachel”
I slid into the warm, bubbling water, feeling my bikini cling to my body. Darren put an arm around me and kissed me. We made small talk. I learned that he is a record executive and a widower. He has two small children who were visiting their grandparents out of state.
“Don’t worry, the swimsuit isn’t hers.” He said with a laugh.
We made out, his hands rubbing my chest and giving my ass a squeeze. I felt his muscular chest, and my hand wandered…until it found something very memorable. I gave it a rub.