Crossdressing School Stories

105,936 results
Orientation
Length
Source
Infinite Scroll

An influential Dare

by femboyslut122 on Apr 20, 2015
Fetish

As a college student most of Kyle's time was spent in class or doing work for class. He knew that others found a better balance, or lack thereof, between class work and a social life. Because of this Kyle always looked forward to the last Saturday of each month. He and his friends would get together once a month to catch up and dick around while playing tabl...

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Recruiting of a Sissy Maid Ch. 01

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

[Welcome to my next story. This story has become a little different in how I planned to write it as compared to my previous stories. It has been fully written up already, as of this first uploaded chapter. Doing it this way allows me to better proof read and adjust for future chapters before uploading each. I will submit uploads on a regular basis for my rea...

Prom Night with a twist

by MissAshleyJ on Apr 1, 2019
Humor & Satire

BUZZ BUZZ BUZZ… “Ugh…” Sam groaned as he pulled himself out of bed. “SAM! Breakfast!” He heard his father calling up as he rubbed the sand from his eyes “Coming” he yelled down as he slumped his way out of his room. He entered the kitchen and plopped himself on a chair. His father dropped a stack of pancakes on the table as his mother looked up from the news...

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To Be, or not To Be; Fucked

by JakeInalake on May 29, 2020
Fetish

Gabrielle was far from below the average highschool boy standards of excellence. For starters, he was way shorter than any boy he knew, he was a stout 4 foot eleven inches, making him even below or barley on par with women. He was very curvy and feminine growing up as well, attempting many sports like track or swim had only decreased his hope in attempting t...

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Laboratory Fun

by Hypnoticus on Sep 26, 2017
Science Fiction

You stand on a street-corner in your home town. The sky is overcast and there's a rumble of thunder in the distance that reverberates off the buildings. You reach in your pocket and pull out enough cash to cover the cost of lunch, shove it into the hands of the street vendor, and begin to make your way back to the office. You would hate to be caught in yet a...

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A Transvestite Odyssey

by lynntg0444 on Mar 18, 2020
Transgender & Crossdressers

I like playing a girl, but it's complicated. I have always been more attracted to women than men, and had many relationships with women including two marriages. As a young man I had several sexual experiences where I played a feminine role. Wearing girly things was a real turn-on for me, and it seemed to make it less queer for us both. I would later learn th...

The Transition Ch. 01

by Quantarx on Jun 8, 2020
Transgender & Crossdressers

Greetings and thank you so much for choosing to read my story. This is intended to be a multi part series so bare with me as I try to develop the characters and lay down the backstories. As always, Your feedback is always essential in the development of the story going forward. Please leave a comment down below * I Had been Married for about eight years w...

Bullied

by Testytesterton on Sep 12, 2020
BDSM

You are an 18 year old boy surrounded by bullies everywhere you turn. Your high school has apparently elected you the mascot of the losers and wimps and selected you to receive the lion's share of attention from the bully boys while simultaneously being ignored at best by the girls you lust after. At home, your family is cruel and controlling or coddling and...

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Several Stories from Somewhere Else

by Freyasbearn on Mar 11, 2018
Fantasy

This is the landing page that will take you to the several stories re-archiving here. I am also using this section for new stories with the same themes as my other stories. That way I don't have twenty different stories all over the place that cover the same stuff. You can get it here. If you want to add on, or take a story a different way-- please, please d...

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Fulfilling all My Fantasies Ch. 01

by classmate1119 on Apr 23, 2019
Transgender & Crossdressers

"Last chance to change your mind, Cristi," Jalen said. "It's probably the most outrageous one so far! Not that I'm worried, of course, but you never know what else might happen... " I reapplied my lipstick in the reflection of the club's glass entrance. "Hey, we spent too much time preparing for this. Don't back out on me now, Jalen!" I threw him a coy smi...