Sissy Roommate Stories

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Orientation
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Topped from the Bottom Ch. 06

by cutebabysadie on Sep 14, 2017
Fetish

Topped from the Bottom - Chapter 6 Summary of previous chapters: Chapter 1: Todd, college football quarterback and alpha jock make a bet with his short nerdy vocal music roommate, Mark. The bet was that Mark could fuck Samantha, Todd's girlfriend, better than Todd. To be more specific in just 10 minutes she would be orgasming and screaming Mark's name. It...

My First Session with Her

by humbleslave on Sep 17, 2017
BDSM

Let me start out by describing who I was. I am 24 years old, 5'6" about 150 pounds, fair skin and short hair. I'd been cross-dressing for about seven years, and had quite a collection. I was living with a roommate, Jane, who had no idea about my hobby. In fact, I'm pretty sure she'd have been freaked out if she found out, so I'd kept it secret. I consider my...

A Surprising Change

by chrissycockslut on Jul 10, 2018
Transsexuals & Crossdressers

This all started several years ago, as I finally turned 18 years old. That was when I discovered it, and it completely turned my life around. I had graduated high school the previous spring and my birthday was the first weekend after I moved into college. Now it's safe to say I wasn't the most popular kid in my high school. Fuck, I don't think anyone anywhe...

Sex Change for a Cursed Exchange Ch. 02

by sucuminx on Sep 19, 2017
Transsexuals & Crossdressers

Brandon, my roommate in the dorm, was a good friend of mine when I first moved in. He and I go way back when we were freshman in college and spending time with each other daily trying to go out partying every chance we get. But things were about to change between us. He wasn't too bad looking for I would check him out at times, but he wasn't like football...

The Pantysissy Diaries Ch. 01

by JPantyboyVSL on Sep 2, 2017
Fetish

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. ***** Jay was on his way back to New York from a weeklong work conference in Chicago. He decided to take Amtrak back to NYC. He got on the train in Chicago and noticed a hot young blonde woman in her 20s s...

A Sissy's Forced Gangbang Pt. 03

by sissy77 on Jan 12, 2018
Transsexuals & Crossdressers

This is the final part of the 'A Sissy's Forced Gangbang' series. I received a lot of positive feedback for the first and second parts and I am very grateful for the same. As for those who requested the next set of events, I would like to apologize for the delay in writing this piece as I was preoccupied with a few other things including a few sissy encounte...

Savannah's Hypnotic Socks Pt. 20

by Fibaro on Dec 2, 2019
BDSM

Chapter 24 Savannah eventually pushed her roommate away and looked down under the table. She just stared at her roommate for a bit before asking. "What moisturiser do you use Roxy cause your skin simply shines." She loved how her roommate face turned red at her joke. She didn't really expect an answer either. She just did it because she loved messing with...

The Exploits of Cockslut Kelly 03

by CSK on Sep 11, 2017
Transsexuals & Crossdressers

Welcome back my glorious deviants. I've missed you. Do you have your cocks in your hands yet (or in your dripping cunts for you beautiful, radiant ladies out there as well)? Today's chapter delves more into the confidence building of my nerdy college roommate. He gets to show off his big dick and dominant man skills in front of two hot co-eds which will in t...

Yet Another Story

by neoview on Nov 26, 2017
Transsexuals & Crossdressers

You're back? I guess my previous story was a hit. The comments stroked my ego enough to write this bullshit. Before I begin, shout out to: Anonymous user, Anonymous user and xploring96 for the feedback. If it wasn't for you guys I probably wouldn't even bother to continue this... I guess I should make it a series... Naaahhhh. Too confusing. Super narrator p...

The Hardest Kind To Be Ch. 04

by Joe Wordsworth on Sep 17, 2017
Exhibitionist & Voyeur

Hopefully, you've read the previous parts--as some of this won't make too much sense if you haven't. Either way, the cast is eighteen and I thrive on your love and affection. Vote me well, mon ami... vote me well. . . .. ... ..... The next morning was a hazy shade of warm beery tastes lingering in the back of Ginnie's mouth. She woke with a grumpy headache...