Sissy Roommate Stories

20,331 results
Orientation
Length
Source
Infinite Scroll

Kaylissa's Conquest Ch. 01

by OcelotTreats on Sep 15, 2017
Romance

"How about him?" Sarah pointed at a student sitting on the edge of the fountain in the courtyard, busily studying notes for a class. I ignored her for a minute as I enjoyed the cool fall air as we both sat under our favorite tree, the usual spot, spending our mornings people watching and studying. It's Sarah's last year at Harvard and I couldn't be more pro...

Chimera Isle Ch. 03

by curiousErres on Sep 13, 2017
Novels and Novellas

Chimera Isle was as perfect as it sounded. The ocean a deep blue, the trees full, with intense green leaves, the air warm and intoxicating. Cambry gazed around in awe as she gathered her luggage from the employee van. Looking around, she knew this was going to be a hell of a summer. "Are you ready?" asked Keeli excitedly. She hadn't stopped talking about it...

My Pool Experience

by ddsfantacy on Sep 13, 2017
Group Sex

It was a nice warm sunny day. Everyone was off doing his or her own thing and I was alone in the house. I decided to go out by the pool and lay in the sun naked. No one was around and I knew they would not be home for sometime so I felt very safe in doing this. Well I got my towel and the sunscreen and went out back to the pool. I sat in the lounge chair and...

Encounter on the Beach

by minnie179 on Sep 2, 2017
Erotic Couplings

"I hate my life sometimes," I thought to myself. Here I am, an independent well-educated woman with my life on track and yet, I cannot find someone to share the simplest things with. And in my more frustrated moments, the horniest things with. Who sits on a beach, in a romantic getaway, alone for vacation? Well that would be me. I had to get away from the...

Law of the Heart Ch. 02

by Headhuntertales on Sep 12, 2017
Loving Wives

No sex in this chapter! * I burst out laughing. "Go ahead and laugh.... what' da say you are called." "Jake," I responded still chucking. "This is the best free afternoon show in town, Jake. Those pretty ladies get on these boats in the tropical sun and before you know it they are going native." "Native?" "You know, topless... sometimes naked as jay-b...

A Night with Stacy

by sohowanderer on Sep 13, 2017
Group Sex

My wife Kathy was always the reserved type. She is truly beautiful but has always been insecure about her looks, her body and sexual grip on men. She is 5’6” with blonde hair, blue eyes and beautiful sensitive breasts that nicely fill a 36D cup. Even when her college roommate used to point out that men would ogle when she wore her miniskirt, she still didn’t...

Tony Ch. 1

by Rebecca on Sep 13, 2017
Erotic Couplings

I'll make the history of things brief. I was a 42 year-old woman trapped in a marriage for appearance only. My husband, a 62 year-old man had told me after our marriage that he was gay, not just gay but he had a hardy appetite for young men. He was wealthy and I guess after my first failed marriage and after struggling with no money for so many years I accep...

Unexpected Tits

by clampealer on Sep 2, 2017
First Time

"Dammit is it hot out here," I would think to myself, but I have to pay for my tuition somehow. "Going to that fucking University sure isn't cheap." I was on my summer break from college trying to earn enough, doing odd jobs, for another semester. I didn't do any skilled work, nobody would hire me for anything like that. I only contracted small jobs of cutt...

The Sorority Ch. 01

by Psycho08 on Sep 14, 2017
Sci-Fi & Fantasy

Hello my first time posting a story so please be kind. All characters are above the age of 18. ***** Amber stood in front of the Sorority house Beta Sigma Psi, which she hopes to pledge, not because she wanted to stay there but because she was hoping to confirm and write about the rumours that surround the house. See the 5'0 blonde was a journalism major a...

Christy Ch. 02

by zaaz on Sep 25, 2017
Group Sex

The Learning Curve Car doors slammed and the engine revved to life. Headlights washed across the room as the car backed out of the driveway. "They’re gone!" Tina sighed. " I’ve been dying. So what the hell did you get up to over there in The Hague?" It seemed like weeks, not days ago that Christy returned from an internship at the World Court. Her dowdy si...