Bully Roommate Sissy Stories

23,222 results
Orientation
Length
Source
Infinite Scroll

Futa: The Emergence

by Smithjohnsonian on Dec 13, 2018
Fantasy

Earth witnessed a massive meteor shower in 1950 which brought along with it extraterrestrial life, albeit as unicellular organisms, several of which crashed as meteorites in Central Asian, East Asian and South Asian countries with a few of them landing in the North and the South Americas. These single-celled organisms had a lot of similarities with viruses o...

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Darling Nikki

by Latexsissy69 on Sep 25, 2017
Transsexuals & Crossdressers

Chapter 1 - The Setup "I'm going to catch him!" Samantha thought to herself as she looked at her disheveled panty drawer. She now had proof that her roommate, Nick, had been wearing her clothes, but had to catch him in the act. She did a search online for ideas on how to catch him. She looked at cameras, tape recorders, etc... but she knew it wouldn't hold...

If I Tell The Truth

by MTMiles on Oct 8, 2019
Transgender & Crossdressers

It would be at least another three days before Rebecca would talk to me. I could guarantee that. Yes, last night had been embarrassing for her. I'd gone off at her in public, but she'd deserved it. She's a pretty girl and is constantly flirting with younger men. I've grown tired of issuing her with warnings about such behaviour. Now she'd thrown a tantrum a...

Letter from Iddlesleigh Harbor

by justincbenedict on Sep 9, 2019
BDSM

Dear Shoeblossom-- I am a townie bitch from a crappy beach village, and I snared a rich little piglet, and I just recorded one of our more pitiful conversations! Stephanie "Stalki" Sendack "I don't think you did that badly, Crates. You actually seem to howl more when I cane you, you know." "Stalki, it feels so marvelous when you stroke...oh it's so nice...

Also

by PTBzzzz on Sep 16, 2017
Loving Wives

There are places in this story where the same person is referred to as Missy, Mrs. Smith or Also. Please understand the names are to give the perspective of the person viewing her. There is no overt sex. If you are looking for a cheap thrill you will not find it in my stories. Hank Williams Jr stated once that he writes songs about subjects he knows. I wri...

Virus S

by thisisnttaken8 on Jan 17, 2021
Bisexual

"FUCK ME YOU STUD!" the slender new trap screamed in agonizing bliss as the muscular stud pounded him from behind. Connor could see the brute's body changing by the second. He arms grew more muscular and his jaw grew more angular, but even stranger was his cock. It seemed to be growing thicker and larger as he plowed the twink's ass. The bull wasn'...

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Coed Love Story Ch. 01

by Lil_kitty on Sep 25, 2018
Erotic Couplings

*Many thanks to Jill for being my inspiration for this story* ***** Chapter I - The Bully Combing her hair in the morning, she looked at herself in the bathroom mirror. In her opinion, her shoulder-length strawberry blonde hair was ordinary, her blue eyes were ordinary, even the freckles on her nose were ordinary. "I don't know what Peter sees in me," she...

Young Sissy Ch. 02

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

I was walking in a field, the cool grass crushed softly between my toes, the sun warm on my skin, the smells of spring were in the air and every deep breath I took filled my lungs with the promise of a fresh start and new hope. The sky was a flawless blue and looked clear enough to take a swim in. Everywhere I turned, all I could see was endless rows of roll...

Gothic Sissy Snowbunny

by Satanicsissybitch on Mar 2, 2020
Transgender & Crossdressers

Don't ask me why but I've recently decided to come clean. To the world, my readers, my friends and most importantly, to myself. I can't hide or pretend anymore and I've decided to just put it all out there for the world to see and, believe me, it's extremely difficult for me to tell the story I am about to tell you. First, I think it's probably important t...

Splint's Humiliation

by justincbenedict on Dec 31, 2018
BDSM

Vince looked doubtfully at Splint, kneeling naked in the corner of his own living room. Then Vince turned his head back at Sparky, who smiled at him. God, watch her toss that ice blonde hair. When Splint began seeing Sparky, the whole crowd had been taken aback. Sparky was overweight in kind of a sexy way--big boobs, big hair all that kind of thing. Most o...