College Sissy Stories

78,474 results
Orientation
Length
Source
Infinite Scroll

Explore the Inner Woman In You

by Tomsparty on Sep 14, 2017
Transsexuals & Crossdressers

I fancied the arse off a girl at school called Sharon. The problem was most of my year did. She was beautiful with long blonde hair, willowy legs, a butt to die for and stunning pert tits. She was way out of my league but quite amazingly we did get on and began to make slow but steady headway. My dizzy ambition was to ask her to the end of year college dance...

Caught by My Bully and Exgf Ch. 02

by CindyTightass on Sep 15, 2017
Transsexuals & Crossdressers

This is second chapter of story about young crossdresser who is discovered by his ex girlfriend and masculine bully from high school. All protagonists of this story are consenting adults. ***** "Your face is a one big mess Cindy," said Michelle giggling, "let's go to the bathroom and clean you up!" She helped me to get up from my shaky knees and led me to...

Sammi Goes to College

by Sissy_Sammi_ on Dec 10, 2017
Transsexuals & Crossdressers

4th part to Sammi's story. After Sam graduated from high school, and knowing he'd be moving to college by the end of the summer meant he was just killing time until then. He worked for most of the summer at a restaurant as a server, and at night Sammi worked as a cam whore. He made some extremely good money by the end of the summer, and he was extremely pro...

Discovered At the Gym Ch. 01

by richysissy34 on Sep 13, 2017
Transsexuals & Crossdressers

A quick backstory, I am an 21 year old college kid, about 5 foot 6, who just recently joined a gym to try and overcome my smaller frame and slim feminine body. I have a secret love for wearing women's clothes, especially lingerie under my male clothes as much as possible. I have no issues with getting women, the occasional hook up and girlfriend from time to...

The Locksmith Pt. 02

by cdbrittany4bbc on Mar 31, 2020
Transgender & Crossdressers

The Locksmith Shop This is a continuation of my previous story, the Locksmith, where I am trapped in a metal chastity cage by a broken lock. We called the local locksmith, but instead of helping me out of my predicament, he unlocked both my wife's and my sexuality. Amy and I had a sleepless night. After Amy sobered up we talked nearly all night. It seemed...

My Wife Erica And Our Friend Jack

by Cute Little Thing on Sep 25, 2017
Fetish

This is the most basic story you can get. A guy decides to give in to his wife's fantasy of seeing him with another guy, and soon learns that its his fantasy too. As with other stories posted in here, it can get extremely racy at times. If issues of sexuality bother or disturb you, then don't read this. I guess like a lot of guys my college years were mark...

Alex, The Closet Sissy

by Areallysissyboy on Feb 11, 2019
Transgender & Crossdressers

My name is Alex, a closet crossdresser. 18 years old, never had a date. Too skinny, too weird, too feminine. I wore my hair long but not a hair on my body tho, not very athletic. Just a 5'3" skinny 125lb pale white boy with long black hair. Who loves dressing like a girl every since my older sister, Sam, moved out 1 years ago which left her old room unsuperv...

Lexi's Interview

by Jemina004 on Mar 17, 2020
Transgender & Crossdressers

October 5th, 2063 Lexi reached for his purse and took out his compact mirror. Mostly out of nervousness, he had to check his appearance again. Alexandra St. Claire was sitting in the waiting room for Carter Logistics on the 56th floor of the MacArthur Building in Chicago, trying to get one of the most coveted jobs available for white bois these days. Being...

Online Fantasy Leads to Real

by puzziboi on Jan 20, 2020
Transgender & Crossdressers

Gabrielle McBeth had a good life. She and her husband, Antonio, were 28 years old and had been married for six years. They had an eight year-old son named Aiden Antonio and a five year-old daughter named Ava Gabrielle. Her husband was an industrious fellow who flipped houses for a living earning just over six figures a year. She was able to be a stay-at-home...

Kyle, The Party Dog

by Mixedwritings1993 on Sep 17, 2017
BDSM

After calling his little brother by his name, Brandon got a little pissed off when no one responded, "Damn, that boy is sleeping once again, man, can't he even stay awake for few hours at a stress?" He stomped on the floor hard on entering his little brother's room and was amazed to see even the loud stomping noise didn't wake up his brother, Kyle. Brandon...