Sissy College Stories

78,474 results
Orientation
Length
Source
Infinite Scroll

Just Another Story

by neoview on Oct 15, 2017
Transsexuals & Crossdressers

Once upon a time... "Wait, wait, wait! We're not actually starting the story like this, are we?" Said the short fat kid in his mid-twenties. "I'm neither short nor fat." He said while swallowing his stomach and lifting himself on his toes. "I'm not doing any of that. STOP GIVING THE READERS FALSE INFORMATION!!" The angry non-short, non-fat kid yelled. "H...

The Hardest Kind To Be Ch. 01

by Joe Wordsworth on Sep 16, 2017
First Time

In the offhand chance that you don't find the setting clear on the issue, all characters are eighteen and legal. This is also a madly different story genre than I'm used to writing, so be kind. . . .. ... ..... She hated her. Hated... though strong and dramatic, it was the only word that summed up their relationship. Nobody would have guessed it, but i...

Ultimate Sissy Weekend Ch. 07

by SissyTwinkleToes on Mar 10, 2020
Transgender & Crossdressers

Ruby is sat flicking through a magazine. Mid-twenties, she's been working in the tattoo parlor since college and is soooo bored. So her face lights up when two sissy dumplings mince into the tattoo parlor. She gasps at their ridiculously effeminate outfits that no woman would be caught dead in. She can't believe they've handcuffed themselves together and loc...

A Tale of Two Bitches

by Lordheed on Sep 12, 2017
BDSM

"Game Over", a deep voice pronounced from the television. Johnny threw down the controller in frustration. 'Can't even win at video games, let alone anything else', he thought to himself in disgust, 'What a way to start winter break'. He'd been home now for 3 days; already missed campus, his dorm room, and the constant business of schoolwork that could keep...

How Nathan became Natalie Ch. 01

by saintlycd on Nov 22, 2017
Transsexuals & Crossdressers

My name is Natalie but that was not the name I was born with; rather it's the name my wife gave me when she made me her "sister" and her cuckold sissy not long after we were married. My real name is Nathan but that's a name I would prefer never to use again because I enjoy being Natalie much more than I ever enjoyed being Nathan. This is a story of how my wi...

Attack of the Yellow Convertible

by 4glory6 on Sep 1, 2017
Group Sex

Gail nudged Sam's body off her stomach and to the side. He was lost to the world. She had about ten minutes she figured before he started to snore and she'd be forced to get up and go to the guest room. The mention of "guest room" got her off on the cryptic e-mail message she'd gotten from her cousin, Faye, earlier in the day: "Landed in PBurg. Docking soon...

My Sissification Ch. 02

by sissy171 on Aug 31, 2020
BDSM

I had always planned to go to college, but I was already fairly secure in my business, so I entered college with no scholastic trepidation. My way bigger fear was that I was still sporting a bikini tan, which kept me conflicted; fearful of being discovered, constantly on a sexual edge, and woefully missing Beth. The bikini bra outline was her "brand" upon...

Ian's New Job

by SatinSlip on Nov 26, 2018
Fetish

Authors note- this story includes non-consensual, rough, and coerced sex. As well as straight and bi-sexual sex. ************ Wendy moaned as her husband slowly licked around her pussy. She grabbed the sheets in her ecstasy. An orgasm rising excruciatingly slowly in her. Ian was great at cunnilingus. He practiced often on his wife. Delighting in the way...

Luke's Field Trip

by LucyAnn51 on Sep 16, 2017
Transsexuals & Crossdressers

All characters in this story are over 18 years old. This is a work of fiction and any similarity to other works or real people is simply coincidental. Hope you enjoy, love you dolls! Xoxo ------------------------------------------------- Luke was a sissy. The kids at school called him mean names and threw things at him. They played keepaway with his book...

OMG My Daddy’s a Sissy (Prequel)

by fittexanman on Aug 22, 2018
Fetish

All characters are purely fictional and of legal age (over 18). * I met Deidre during my first year in college. We were neighbors on the 1st floor of Elliot Dorm. She was an art student, and I was a business major. It didn't take us long to realize that we weren't like the others at this school. As it was located in the Southern part of the country, our co...