Crossdressing School Stories

105,936 results
Orientation
Length
Source
Infinite Scroll

Fine Line Ch. 01

by raven10101 on Sep 12, 2017
Erotic Couplings

Eve: I met Michael in elementary. My parents moved me into the school district, and I had no friends and a serious attitude. He tried to play me for a fool in various unimaginative ways, but I was almost always able to avoid the fallout. He only got in trouble about half the time, but he still blamed me. As we grew up, our emerging personalities clashed and...

Getting to Know You

by mistyfdfa on Sep 15, 2017
Sci-Fi & Fantasy

Frank's knee bounced nervously as he sat on the park bench waiting for his date. He hoped Justin would look something like his photo on the AugNET dating app so he could pick him out of the milling crowd. He equally hoped he noticed his tall and thin beanpole-like build in the sea of people out for the afternoon on the Jersey boardwalk. At the very least, he...

Something For a Rainy Day

by RichardGerald on Sep 12, 2017
Non-Erotic

A little wicked story. Sorry no sex and no editor. I hope you enjoy. The economic storm that enveloped J.W. Parker & Associates that bright spring morning came without warning clouds or distant thunder. Ellen Walker came into work as usual and found the storm well advanced. The men in dark suits had descended into every corner of the office; they were well...

Captain's Woes Ch. 09

by superpeanut on Sep 14, 2017
Erotic Couplings

The next day at school certainly could have been awkward for Dan, if he had allowed himself to notice any of the girls he had slept with in the past week. Jane, of course, was pissed at him and wouldn't even look at Dan. Miss Kline kept trying to get his attention, but he remained absorbed in his work. Casey was feeling both neglected and horny, and kept com...

The Homeless

by brunorivera on Sep 17, 2017
Mature

I am Ivonne. My parents got married when they were too young and they got divorced when I reached my adolescence. My mother remarried a man of bad character, and both became alcoholics. At first, my stepfather didn't sympathize with me, because he scolded me without reason. When I turned sixteen years old, his attitude changed, becoming more affectionate. Bu...

Pass the Pussy Ch. 3

by MNBSUJO on Aug 31, 2017
Fetish

"Will I see you tonight?" Mike asked as he pulled his shirt on. "No I'm going to hang out with Julie at her house and then I've got a paper to finish." "Then what about tomorrow night?" he asked now putting on his shoes and socks. "Yeah, but not 'til after nine." "Alright. I'm gonna be late. See ya tomorrow night." And with that he left. Mike had been my b...

Field Trip Fun

by lottyboo on Sep 13, 2017
First Time

The school I went to was a catholic girl's school. Don't navigate away; this isn't one of those 'convent girl gone bad' stories. This the true story of my first orgasm. I was 18 years old, and hopelessly innocent. Of course, I thought I was street wise. I was one of those that gives it all the gob, tales of all the boys I'd kissed, flirting shamelessly wit...

Unraveling Ch. 02

by Myalyn on Sep 16, 2017
Romance

Brandon McCaul looked at the woman in front of him, the grown up version of the girl he used to know years ago in high school. She was so sure of herself back then, so smart and caring. How could she have gotten herself into a situation like this? She must have had some issues, but they never showed back in school. He remembered her on stage, acting in the p...

Something About The Way He Moved

by starfromheaven on Sep 12, 2017
First Time

**THE FOLLOWING IS A TRUE STORY** BRACE YOURSELF Every day of chemistry we made perfect eye contact. Something about the way he looked at me made me feel as though he saw me in a different light than he did my peers. It was undeniable that i wanted him badly, and I think he could tell. He is the type of man that you can't help but stare at. His beautifully...

Lynne & Brad Ch. 01

by SKyoto on Sep 11, 2017
First Time

Author's notes: This is my first real attempt at writing erotica; feedback is most appreciated. If people like what I've done, I'll write some more! All characters in this story are in their last few years of education, and are all over eighteen. Lynne slipped round the bike shed, into the gloom created by the overhanging trees from the hillside behind....