Sissy Roommate Stories

20,331 results
Orientation
Length
Source
Infinite Scroll

Perfect Roommate Pt. 03

by fbblvr37 on Aug 30, 2017
Fetish

Perfect roommate part 3 By Fbblvr37. Luke finds a roommate who shares his muscle fetish and transforms her body into the girl of his dreams. ***** Part 3 ** Chapter 10 ** For the first time she wondered what Luke would think since she didn't come home last night. Should she have given him a message to let him know she was alright. Would he be worried. R...

Side Bet Bluff Ch. 03

by statsultan on Sep 14, 2017
BDSM

Part 3 – Sunday Morning (Jan 18) I slowly awakened to a very pleasant sensation on my cock. Jaycee was no longer curled up next to me but had instead scooted down to my lower half. "Oooh, does Billie's willie want to be sucked?" asked Jaycee quietly. I opened my eyes slightly and gazed down at her. She was on her side looking intently at my dick, which she...

Caught in the Act

by AnnHoytRedlass on Sep 12, 2017
Erotic Couplings

Sitting on a stained and well-worn maroon chair on the third floor of the library, Jeremy was working diligently on his laptop to finish up the remaining slides of a presentation for one of his classes. The afternoon sunlight bathed the room in rich natural light through windows that surrounded the sitting area he was working in. This was his favorite place...

Down the Long Empty Nights

by Colleen Thomas on Sep 25, 2017
NonHuman

Down through the dark ages of time I have come, the embodiment of Jung's collective memory. Freed long ago of mortal constraints, I have impassively watched civilizations rise and fall. Alexander, Caesar, Cleopatra. Dusty names applied to almost mythical figures, yet to me, living memories. The glory that was Rome, mighty Carthage, mysterious Byzantium,...

Rumors Just Might Be True

by primetime73 on Sep 19, 2017
Erotic Couplings

Becton University required students to live on campus in the dorms for the first two years of school but I didn't mind. I was somewhat lucky in that my roommate flunked out halfway through first semester of my sophomore year leaving me with a room to myself at least until the end of the semester. It was great having a room to myself, not having to share or w...

Breaking the Curse

by Scorpio44 on Sep 13, 2017
Group Sex

[This story contains oral sex, MF, MFF, FF sex. No anal, no bondage, no cheating, no BDSM, and no animals were hurt or injured in the writing of this story. No religions are defamed or mentioned. If you are looking for any of the things that aren't in this story you will be disappointed. If you might like a story about people meeting and beginning something...

BMOC: The Innocent Ch. 01

by TripleL on Sep 12, 2017
First Time

This is a stroke story. It's ridiculous and unrealistic. No one is worried about STDs, sizes are exaggerated, everyone is bi (or at least the women are) and people can fuck for hours without chafing. This story has decidedly sacrilegious content—not so much in this chapter, but in the ones to come—so if you don't like that, look elsewhere. ----- "I can't s...

Marilyn's Adventures in School Ch. 03

by walterio on Sep 26, 2017
Group Sex

MARILYN RECEIVES A SPECIAL ASSIGNMENT Marilyn was in Jim Carlson's classroom at the end of the school day. The door was locked and they were both naked except for Marilyn's knee high socks. Jim would normally be satisfied with a student bent over his desk with her panties off and her skirt flipped up over her back. However with Marilyn's incredible body, he...

"Pick A Card, Any Card..."

by JimBob44 on Sep 13, 2017
Group Sex

*Author's Note: Any and all persons engaging in any sexual activity are at least eighteen years of age. ***** Because of the heavy pounding October rain, there were few customers for the five food trailers in the U.L.D. campus quadrangle. The University of Louisiana at DeGarde cafeteria was packed with students and faculty alike. "Tracy! Emily! Over here!...

How to Date a Superhero Ch. 04

by frozenhero1 on Sep 19, 2017
Sci-Fi & Fantasy

The late night darkness was suddenly dispelled by a singular flash of brilliance. The light sizzled and expanded into a large sphere before exploding soundlessly and leaving two figures standing in the dewy grass of an endless and rolling meadow. Mega-Girl was in her red one-piece costume, wavy blonde hair falling to the middle of her back mingling with a pl...