Crossdressing School Stories

105,936 results
Orientation
Length
Source
Infinite Scroll

Schoolgirls and Schoolboys

by JDBDS on Sep 16, 2017
Transsexuals & Crossdressers

(Disclaimer: This is a true story.) This is a story about myself, my girlfriend Shannon, and one really, really hot crossdressing dude. Or girl. A note--I would describe myself as a straight guy, while she would describe herself as 75% straight or so. The story begins back in December or so. Shannon and I are both in our early twenties, we've been dating f...

Geis

by kotochaos on Sep 27, 2020
Cheating Spouses

Trigger Warning: This story contains some sexual and emotional violence. This is nota healthy representation of a relationship, nor should it be something to strive for in your own life. This is a work of fiction, and the actions taken in this story are taboo for a reason. Be good to each other. School let out for the summer, leaving Kendall and Jackson with...

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Becoming Mindy

by mindyrose on Sep 18, 2017
Transsexuals & Crossdressers

Hi. This is my story from an unsure, shy, awkward boy that was pretty feminine to a proud, confident and comfortable transgendered girl. If you're not into reading about transgendered people and their stories, as well as their sex lives, then please move on. I know I made some foolish decisions, but I am a completely healthy person today and those decisions,...

Jeff Crossdresses More & More

by TurningintoCD on Sep 12, 2017
Transsexuals & Crossdressers

My name is Jeff. I date girls every now and then but I always masturbate about dressing up as a hot chick and seducing a hunky guy. My biggest turn on is putting on women's clothes and makeup. I never really had a chance to explore it much when I was growing up. In college I had a secret stash of 1 stick of lipstick, and when I felt really dangerous, I wou...

Escapism: The Modern Man

by chasingrisque on Sep 13, 2017
Transsexuals & Crossdressers

*Synopsis: 25, in and out of relationships and one-night-stands. In debt, slightly overweight, unfulfilled at work and in life. Sick of his friends and routine, Alex accidentally reawakens feelings he has not had for a long time. Think Trainspotting for sissies - American Psycho without the violence and lot more lace, lip-gloss and high heels.* ESCAPISM:...

Passion over Lust

by sarahchica96 on Sep 5, 2018
Transsexuals & Crossdressers

Introduction I' am living the dream, the dream of maintaining the balance as a regular straight guy and my bisexual crossdressing side Sarah. The 4 years of hard work at University started paying dividends, I landed a job as a legal advisor for one of the top businessmen in London Mr Hayat. My job paid well which enabled me to buy a studio apartment via a...

Staying Together

by komrad1156 on Sep 12, 2017
Transsexuals & Crossdressers

"I'm not sure further sessions will be of much use to either of you. After seeing both of you twice of week for two months, neither of you is any closer to resolving your concerns than we were when you first came to me." Dr. Nelson was good. She had the ability to examine a problem, bound it, and then dissect it into smaller pieces. She'd done that with bot...

Caught For the Last Time Ch. 07

by TGJamie on Sep 15, 2017
Transsexuals & Crossdressers

We awoke in the morning almost identical to how we both fell asleep. I was still in the babydoll nightie she had given me and she was still in her palazzo pants, heels and pony tail, and no top. "That was quite a night," she said as she sat up and unstrapped her heels. "When was the last time I woke up with heels on?" We both laughed as I shook my head. Th...

Sissy Maid to Be... Ch. 01

by missjennymaid on Sep 5, 2018
Transsexuals & Crossdressers

Prolog I have always had the desire to dress like a girl. It started at a young age when my mother used to have me try on dresses to "see if they would fit my cousin." As I got older I still had the desire and it got strong enough that I started going out in public in college. I was lucky enough to meet and marry a woman who was accepting of my "hobby". Liz...

Sexual Scenarios

by zig322 on Dec 7, 2019
Fan Fiction

What we have here is a series of sexual scenarios from anime, cartoons, comics, tv shows, video games, movies, and even some original ideas. These scenarios will involve: spanking, ENF, forced feminization and crossdressing, foot fetish, tickling, LGBTQ, mind control, incest, any other perverted thing anyone can think of, and of course sex (consent or non-co...

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