Sissy Teen Stories

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Das Leben als süßer Sissy Sklave

by Captain Simpel on Oct 30, 2020
Miscellaneous

Justus war ein durchschnittlicher Junge mit etwas längeren schwarzen Harren, der gerade zu übers Wochenende zu Marie wollte. Die beiden waren schon seit der fünften beste Freunde und unzertrennlich. Etwas beneidete er sie für den Reichtum ihrer Eltern, die ihr mit 18 ein Leben in einer eigenen Wohnung ermöglichten, obwohl sie im Moment nie viel verdiente. Al...

Neighbourhood Sissy

by Abusedbyfuta on Feb 7, 2019
Fetish

Your a young man in his late teens. Average build, average height, brown hair, green eyes. You know the type never stood out in a crowd for your good looks but never scared children when you went to the store either. Having just finished high school ou decide to start doing odd jobs around the neighbourhood to raise some money. Maybe it was college, maybe it...

Big Black Cock: A Sissy Surprise

by silkstockingslover on Feb 13, 2018
Illustrated

Summary: A wife joins her husband as a slut for a teen BBC. Note: This is a 2018 Valentine's Day story so please vote. Note 2: Thanks to Tex Beethoven, thor_p, Robert and Wayne for editing this story. WARNING: If you hate gay stories, interracial submission, sissification (not a word I know) or cuckolding please don't read. If you do like those themes.....

Sissy Plays the Game of Thrones

by SissyKelly on Dec 1, 2017
Celebrities & Fan Fiction

Kelly Waters, fucking Waters I thought to myself as I shook my head. I think the worst part of being a bastard is knowing you could choose any last name, but having it dictated still by birth. I knew not who my parents were, in fact I only knew I was Kelly Waters thanks to the man who raised me, Lord Petyr Baelish. I was born in his house, his whore house,...

Sissy Secret Exposed Ch. 01

by LtBroccoli on Jun 5, 2018
Loving Wives

Leaning across the bed to kiss her husband goodbye, Amy noticed her own naughty scent still clinging to his chin. "How lazy," she thought, "I really need to teach Mike how to clean up after sex." Fortunately for him, there was no time for admonishment this morning. She had a big meeting with the CEO in less than an hour and a crucial dinner with clients toni...

An Aussie Teen Romance

by cbrguy on Jul 14, 2020
Romance

Declan O'Reilly's teen years had always been miserable, with bullies seeming to line up to taunt him. Sure he never liked sports or "blokey" stuff like most other boys did but no-one else seemed to cop as much shit as Declan did. Even one of his former high-school teachers had called him a sissy, not once but twice. Declan was a grimly shy 15-year-old boy w...

Town of Hidden Desires

by Birbfinchy on Oct 27, 2020
Fetish

A U-Haul van pulls up outside a beautiful blue house in the suburbs of Setgow. Skylar, just turned 18, steps out of the van and relishes the cool breeze on his face as he stretches' his thin legs after being trapped in the car for the past 4 hours, the wind pushes his neck-length dirty blonde hair past his bright blue eyes which he gently brushes aside back...

A Sissy Cuckold to another Sissy

by Gemsissy on Sep 26, 2017
Fetish

"Christ, Bob!" snaps Julie. You just sigh as you feel your skinny cock throb and spurt into the condom next to her bottom. "What about me?" "I'm sorry, honey. You're just too sexy! I came so fast!" you say, blushing in embarrassment that you couldn't fuck your own wife for more than 30 seconds. "Are you some fucking teenager dweeb?!" She spits as she glare...

Julie is a Whore Ch. 05

by Pretty_Sissy_Julie on Jul 14, 2020
Fetish

Ch. 5 I am a sissy cross dresser that has been living as a woman in Madame's brothel for about 3 years now. During that time I have perfected my skills as a cock sucker and a top notch prostitute. I have my own room in the brothel where I live and entertain clients in other parts of the House. My sister, Becca, does not live in the brothel, but whenever she...

Sissy Powers Ch. 08

by ClarasBestFriend on Sep 29, 2020
Sci-Fi & Fantasy

I froze, holding 3 plates of food, and nearly dropped them. Clara looked pretty upset, and Heather looked mortified. "Uh, hey girls..." she said, sounding pretty nervous. "This is, uh, Connor, my boyfriend... He wanted to come along tonight to meet you both..." Clara and I just looked at each other, and I set the plates down before turning to face them. "U...