Sissy Roommate Stories

20,331 results
Orientation
Length
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Infinite Scroll

Kiss My Scars Away

by LithiumMidnight on Sep 14, 2017
Erotic Couplings

My mind was racing with all the things that had gone wrong. I was lying in bed trying to read a Nicholas Sparks novel. That was not helping a damn thing. All the romance just made me wanna curl up in a ball and die. This shit never happened. And even if you caught a glimpse of it, something would come along to fuck it up. My roommate opened my bedroom do...

What Dark Corners Are Made For

by butterfly_lies on Sep 14, 2017
Exhibitionist & Voyeur

A while ago, I stumbled out of bed in a daze. I slipped into my chair, my body shivering and started scribbling a letter to my boyfriend. T'was the dead of winter, but in a steam mood that made me feel nothing but tropical passion. My fingers trembled around the pen, and my thighs squirmed around the thin knot of fabric wedged against my slit. I felt so wet....

Bella's College Experience Ch. 01

by christalena27 on Sep 12, 2017
Toys & Masturbation

Bella stared down at the pages underneath her hands, watching as the words slowly began to blend together. She had been studying for this exam for hours, and by now any knowledge that was to be imprinted on her brain had already done so. So why did she still have the book open? Truthfully, it was because she had nothing better to do. Entering college had bee...

Not So Boring Afternoon Ch. 04

by agpatch2 on Aug 30, 2017
Group Sex

So for the next few weeks I was Ed's bitch. I got him off pretty much everyday. Sometimes I would suck him off in a public bathroom. Sometimes, when his roommate was away, we'd have marathon sex sessions at his place. He really worked on me during those times at his place. He was really into stretching my asshole. He'd shove butt plugs up there and then try...

Cum Fetish

by hotchat on Aug 18, 2017
Fetish

Over the years I have had many sexual encounters. My first ones were pretty normal with several different girls that introduced me to the world of sex. The early encounters were basic finger jobs and hand jobs in the car at the drive-in. In those days most girls would jerk you off and let you finger fuck them till they came, but wouldn't do much more. I alwa...

Crown of Thorns

by TheVelvetEdge on Aug 18, 2017
Fetish

"I'm really excited about this class -- I want to learn all I can about needle play," S said. I sat behind the wheel next to a woman I barely knew. We were driving back to my place from a night out. I listened carefully as she told me about drawing blood from a consenting masochist, the details bringing a flush to my face I hoped the darkness concealed. I...

Fidelity

by IsoldeLovesTristan on Sep 14, 2017
Toys & Masturbation

"Okay, I'll be back in about half an hour." "Awesome...hey, get some more ice while you're out." "Yeah, right, as if there'll be any left." Ryan closed the door to the apartment behind him. Lana stood up and crossed the room to adjust one of the large fans that sat beneath the window. Satisfied with the new angle, she flopped back onto the couch, opposite...

How It Should Have Happened

by MyPenIsMighty on Aug 18, 2017
First Time

Dom grinned, slouched in a taxi. His head was spinning and it didn't sound like the driver was speaking English, but someone's hand was in his and he had vague memories of grabbing an ass at the club with no negative consequences. Flashes of accidental bumps swirled in the still-ringing bass notes underneath his brain, and a flirtatious hat theft. The cab st...

A Video Guest

by WyKkEdAnGeL on Sep 1, 2017
Group Sex

Lacy crawled out of bed and slipped on a shirt to go to the bathroom. She was tip-toeing down the hall trying not to wake anyone, when she heard moaning coming from her friend Kelly’s room. Closing the door to the bathroom, she thought to herself “wonder who she has in there this time?” Then she rolled her eyes and went on about her business. After she fini...

A Stuffy Doctors’ Conference Ch. 04

by marla_gillis on Sep 16, 2017
Group Sex

The drive back to the hotel didn't take long, and I was showered and downstairs again by 10. I was sitting in a lecture, barely able to stay awake, and possibly nodding off. I came back to my senses when I had people enter the row I was in from either side. As I glanced up, I realized it was Victoria and Joshua. It seems they had both gone to my room to knoc...