Sissy College Stories

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Orientation
Length
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Infinite Scroll

College Misery Ch. 01

by newauthor19 on Sep 16, 2017
Fetish

Ever since words got out that James has some femboy porn hidden in his laptop it has been a nightmare for the 19 year old poor boy standing 5'8" and weighs merely 122lbs. His classmates have totally lost all respect for him. He was admired before for his friendly attire and kind hearted nature but now he is admired for his feminine body. He lives in a boy's...

Kinky Adele Mummy Fucker Ch. 02

by Sissy Adele Howells on Sep 17, 2017
Fetish

I had no idea what a dominant, perverted women Adele Howells could be. She wanted me to take her eighteen year old daughter's virginity, but at a price. Everything would be on her terms. She now had complete control over her husband Tony. I was made to sit naked on her bed, as I watched her put her lipstick and clothes on. My cock was as solid as a rock, as...

Bike Shed Rendezvous

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

You're hopelessly under her spell, captivated by her beauty, your little cocks been taken over. With no mind of your own you long to be put in her knickers and be her girl. Beg dog beg! She's got you by a psychological lead attached to your balls and is leading you to whatever and wherever she desires. 'Please, please!' you plead. 'Emasculate me.' Sound fa...

Black On Black Cuckolding : Hell

by Samuelx on Apr 3, 2019
Group Sex

Officially, we don't exist. That's what conventional wisdom tells us. If you were to type the words "Black Cuckolds" on Google, all you'd get are references to the standard-issue Cuckolding, which typically involves a big Black guy fucking a White woman while her husband or boyfriend, also White, watches. Nothing wrong with that if that's what moves you. My...

Momdom a sissy son's wish

by Viking973 on Jun 20, 2020
Transsexual

Intro: You never had much luck with the girls in high school. You had a few girlfriends early in high school but the last 2 years before college was rough. It had come and gone, you enjoyed it, you weren't an outsider and had many friend groups but you never went out to parties or out of school to meet up with friends. You enjoyed video games and porn too mu...

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Barbie's BBC Beginning

by jacki697 on Jun 9, 2020
Transgender & Crossdressers

I had always been curious about men. I had always wanted to experiment but alas I was way too scared of being "gay" to ever follow through on any of my urges. Chalk that one up to 18 years of living in a conservative Christian community. Instead I left my sexual urges to the alone time I had to indulge in my other fantasy of crossdressing. I loved the thrill...

Power of Panties - The Beginning

by satinmarabana on Sep 12, 2017
Transsexuals & Crossdressers

When I was growing up, underwear was just one of those details of life. Always wear a clean pair in case you get in an accident! Sure it was nice to get sexy pairs as I got older. I still remember my first satin bra and panty set from Victoria's Secret, a gift from my older sister who delighted in showing me the ways of the world. But I never understood wha...

Holly's New Start

by Sissyhalo on Nov 26, 2017
Transsexuals & Crossdressers

I love Jamie so much it hurts. I mean there's a lot of things that would have people freaking out over this relationship of ours especially how I am and how we started. Jamie loves me despite my past. And like he really, really only has a sort of little picture of just how bad I was as Holt. Only he found reasons why Holt ended up so broken. No, no excu...

Mindy's Moving Day - CFNM Ch. 02

by BuckyDuckman on Sep 25, 2017
Interracial Love

Author's note: I think this works as a stand-alone. I get my lily white ass reamed by a big black bull in front of my wife, her friend and my swim team. Delicious humiliation! Mindy's moving day signaled a huge change in her life and the relationship I have with my wife, Debbie. That was the day we put on a real life show of me offering up my sissy ass wh...

Ride of My Life

by Tomsparty on Sep 13, 2017
Transsexuals & Crossdressers

As a student at college I wanted a bicycle for Christmas. I hadn't past my driving test and even if I had, I couldn't afford to run one with my Saturday job wages. My parents didn't have much money so I didn't ask for an expensive model by name, anything would do. I didn't think they could go far wrong or could they? They did attempt to wrap it with some f...