Sissy Roommate Stories

20,331 results
Orientation
Length
Source
Infinite Scroll

A Warrior's Tale Ch. 1

by Sell-Sword on Sep 12, 2017
Erotic Couplings

I have a strange hobby - definitely not the sort of thing you tell your co-workers about at the water cooler. Nothing illegal - it's just that they wouldn't understand... My hobby takes up lots of time, it involves unusual costumes and leather and iron, and hitting people with sticks for fun. I'm a medieval re-enactor. I do the Renaissance Faires and craft...

Julia's Sexual Awakening

by Terrafic on Aug 16, 2017
Exhibitionist & Voyeur

For as long as I can remember, I had been a quiet girl, who kept to herself. Through all four years of high school, I was the girl that no one wanted to talk to. The popular girls were all off dating and partying, while I stayed inside and read books. Blondes seemed to be the top pick for all of the guys, especially with the girls that developed early. Their...

My New Castle Ch. 5

by captivate on Sep 14, 2017
Erotic Couplings

Christmas morning, David got up early and hurried downstairs. He lit the fire, prepared cocoa and cinnamon rolls and made sure that all the gifts from Santa were displayed. Then he went to wake his Rebecca. As he neared their bed, he paused, watching her sleep, amazed again at her sweetness and warmth. He almost couldn't remember the days, months and years h...

Side Effects

by TasteofHome on Sep 16, 2017
Sci-Fi & Fantasy

9:00 Friday Night The pain raced behind her eyeballs like lightening bolts dancing across the sky. Each flash was brilliant in its presence and ever so immobilizing. Gritting her molars, Natasha tried to ignore the pain and the gathering thunderclouds in the sky as she half-halfheartedly reaches the medicine cabinet hoping for relief. Her reflection in the...

The Roommate Ch. 01

by SukiJane on Aug 30, 2017
Exhibitionist & Voyeur

CHAPTER ONE Siene was his roommate's girlfriend so she was off-limits. But Caden had wanted her ever since he'd moved in several months ago. He'd tried to put her out of his mind but things had only gotten worse. A month ago he walked in on her in the bathroom as she was stepping out of the shower. "Oh!" She jumped with surprise and grabbed for a towel, b...

Calendar Girl(s)

by Foxwood20 on Sep 1, 2017
Exhibitionist & Voyeur

Kelly and her old college roommate Holly were the best of friends. Kelly was 25, 5'10" with natural blonde hair, sparking blue eyes and an impressive pair of still perky breasts. She was long-legged with an athletic build, she had played some volleyball in college just a few years earlier. Holly was a little shorter, with auburn shaded hair (and carpet mat...

Your Ex-Lover is Dead

by miserybusiness on Sep 14, 2017
Interracial Love

Dr. Morris crossed her sexy legs and pulled her skirt down to make sure her cooter wasn't showing, Sharon Stone style. She picked up an ice-filled tumbler from the table and reached over, handing to me. I grabbed it with quivering hands. "Thanks." After a few sips of water, I decided it wasn't enough. In my bag was a flask of whiskey. After adding the secre...

Emily Ch. 03

by totalrandom on Sep 26, 2017
Romance

"Oh, that's great!" Michael said, grinning. "I knew you'd get a job soon enough. I wish I had either your charm or experience, I might be as lucky." Emily smiled. "Don't worry, you'll get one soon. It's hard getting into anywhere at the moment unless you've already had 2 years experience doing exactly that." "You can say that again." "Yeah, but I've forg...

Spring Break Party

by jnny on Sep 13, 2017
Group Sex

Christina, Chuck and Jeff had been friends since elementary school. Now in college, they thought nothing of sharing an apartment. Others didn't see it that way, though, with Chuck and Jeff frequently asked by other guys if they shared Christina too. "She's just a roommate and childhood friend," Chuck and Jeff would tell them, smiling. A week before spring...

Kollege Kredit Pt. 02

by dandygent on Sep 12, 2017
Erotic Couplings

Chapter Three Kristine walked into the lobby of her dorm at 5:58 and saw Kurt sitting across the room reading a magazine. She walked toward him, hoping he would look up. He did. He grinned as he stood. "Well, hi. Haven't seen you in a while." She smiled and took his hand. They walked across the lobby and out the door to Kurt's aging but well-running car....