Sissy High School Stories

209,604 results
Orientation
Length
Source
Infinite Scroll

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...

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Sissy_World 02

by JDBones on Sep 14, 2017
Transsexuals & Crossdressers

John Maxwell hummed under his breath as he wiped down the counter tops of the kitchen, cleaning up before his Husband got home. Dinner was ready and waiting on the stove for her whenever she got home from work. He was petite, standing at four foot five, and slender though lightly toned. He had long ash blond hair that fell past his well rounded, juicy ass a...

Find the Cheerleader, Save the World

by Sissyhalo on Sep 16, 2017
Transsexuals & Crossdressers

It started with my brother Holt. A year younger than me he's...he's turned into a fucking cuck sissy faggot. I'm serious and I'm not just spouting off. Holt's always been a dense guy but this...he starts hanging with this loser from high school and I mean a loser. AV club, geek stuff, nothing in Holt's yearbook that said anything but loser, geek and loser...

Allyson the Sissy Whore Ch. 01

by sissymaidallyson on Sep 12, 2017
Transsexuals & Crossdressers

Kevin was your prototypical mid 20s guy. He had a decent job and lived on his own. He had good friends and whilst he was single he didn't find any problems getting what -- or who -- he wanted in the bedroom. However he had long been fascinated by glory holes and by being serviced in them but by being the one servicing. He was convinced he was straight and l...

The Hardest Kind To Be Ch. 01

by Joe Wordsworth on Sep 16, 2017
First Time

In the offhand chance that you don't find the setting clear on the issue, all characters are eighteen and legal. This is also a madly different story genre than I'm used to writing, so be kind. . . .. ... ..... She hated her. Hated... though strong and dramatic, it was the only word that summed up their relationship. Nobody would have guessed it, but i...

The Last Range War

by Egmont0409 on Aug 31, 2017
Humor & Satire

A SATIRE, perhaps historically incorrect in places. INTRODUCTION In 1912 a rancher's son Lee Stanton, aged twenty-two who was heading home after failing final exams to qualify as a pastor, unintentionally started an escalating feud between the Stanton and Murphy families that probably was the last of the range wars. You won't find it in history books beca...

Simon Sissy Slave Ch. 04

by Timewarp10 on Aug 20, 2019
BDSM

Simon staggered in for work the day after the slave auction, his body stiff and sore. Mr Berne and the others in the post room were shocked to see the sissy's bruised and lacerated buttocks. Barry's stiff cock betrayed his feelings; whipping and torture excited him. His sadistic nature relished the thought of thrashing Sissy senseless. Sissy was his fuck t...

Blackmail by Choice

by Sissy_Sammi_ on Mar 6, 2018
Transsexuals & Crossdressers

Christopher was twenty six and had gotten his degree from a prestigious university in southern California. He had worked for the best grades possible all through high school, and all through college to get his degree. It worked out because in his field he was already getting job offerings before he had graduated even. So when he did graduate, he already had...

Black Cuckolding Dreams

by Samuelx on Sep 11, 2017
Group Sex

Sometimes what you're looking for is closer than you think. Take my fiancé and I for example. My name is Stacey Walton and I'm a young Black woman living in Milton, Massachusetts. I studied business administration at Bay State College and earned my MBA at the University of Massachusetts at Amherst. Presently I work for a real estate company in Brighton. I me...

Yet Another Story

by neoview on Nov 26, 2017
Transsexuals & Crossdressers

You're back? I guess my previous story was a hit. The comments stroked my ego enough to write this bullshit. Before I begin, shout out to: Anonymous user, Anonymous user and xploring96 for the feedback. If it wasn't for you guys I probably wouldn't even bother to continue this... I guess I should make it a series... Naaahhhh. Too confusing. Super narrator p...