My friend’s parents were out of town during college Christmas break so she invited some people over.

The word spread and what started as just a few of us sitting around grew until we had a party on our hands.

Liz was already known as one of the hottest freshman girls, a blue-eyed brunette who showed off her big tits and round ass with the tightest possible jeans and sweaters. She was my newest crush, though we’d never said more than “Hey” to each other, so when I saw her come through the door my stomach got all tingly. But Liz didn’t seem interested in me and quickly disappeared. 

I sat down with some girls I knew from school. They were tipsy and trying to think up fun things to do when one of them said, “Hey, let’s dress Jeff up like a girl!” This was hilarious to them because, while I’m not a macho jock or anything, I’m over six feet tall, stocky through the middle, and have an Adam’s apple like a fist. At first I refused, but when three cute college girls drag you upstairs into a bedroom and say, “Get undressed!” it’s hard to say no.

First they did my makeup: eye shadow, mascara, blush, and the reddest lipstick they could find. Then they put barrettes in my hair, had me put on a pearl necklace, a big black bra, and matching pantyhose. I tried on a few dresses till I found one that fit: a black taffeta gown that looked like a prom dress. Voila! I was transformed.

She slid her hand up my dress, found my cock inside the pantyhose, and rubbed it through the nylon.

I went back downstairs. All my friends were laughing and taking pictures as I wobbled around in high heels. Pretty much everyone agreed I made a very ugly woman — except for Liz. Once the novelty wore off and people’s attention moved on, she came and sat next to me, stroked my dress, helped me fix my lipstick, and told me how cute I looked. Pretty soon we were making out, her tongue in my mouth, her hands all over me.

“Let’s go somewhere private,” she said, and we slipped upstairs to an empty bedroom.

As soon as we sat down on the bed she slid her hand up my dress, found my cock inside the pantyhose, and rubbed it through the nylon. My dick was stretching the fabric way out. Liz lowered the dress’s shoulder straps, pushed up my bra, and licked my nipples while stroking my cock, occasionally adding a second hand to caress my balls. I made a move to get on top of her but she didn’t want that, and she wouldn’t let me take off my new clothes. Eventually, I was able to slide her tight jeans off. I slipped a finger inside her tight pussy and moved my other hand to her amazing tits.

Pushing me back on the bed in the dimly lit room, Liz kept working my cock. I think it turned her on to touch a dick and a taffeta dress at the same time. Just when I thought my balls would explode, she yanked the pantyhose down below my knees and got on top and started fucking me like mad. She even slapped my face a few times as she rode me.

I slid my hands up under her bra, kneading her perfect tits, and then her hands were in my bra, rubbing my nipples. Her pussy was so hot and tight and dripping wet, the only thing that kept me from immediately blowing my load was looking down at the absurd vision of my feet in high heels and my hairy legs in nylons.

When I finally said “I’m gonna come,” she rode me even faster. I came loud and hard but Liz didn’t stop, fucking me until I heard her gasp and tremble.
Later on, when I came out of the bathroom, all cleaned up and dressed as myself again, Liz was back downstairs with her friends. I could see her putting her coat on and telling them to hurry up. I waved good-bye to her but she ignored me. Now that I was just a regular dude again, she wanted nothing to do with me.

Check out the Full Gallery