Sissy High School Stories

209,604 results
Orientation
Length
Source
Infinite Scroll

Judy: Prom Night

by caprine on Sep 1, 2017
First Time

[This is a work of fiction. It is an unadulterated and unabashed attempt to tickle male fantasies, and as such, may or may not be entirely realistic. With the exception of The Fab 4, the characters, settings, and events of this story are fictitious and any resemblance to actual persons, living or dead, is purely coincidental.] ***** Hi, remember me? I'm H...

Family Isn't Blood - Fred's Life Ch. 01

by wieliczka on Sep 15, 2017
Romance

Please read http://www.literotica.com/s/family-is-not-blood-ch-01 It will aid in understanding this story. Recently, a friend of mine from California called and said he was getting married again. His previous wife of over 34 years, whom he was honestly devoted to, had died in a freak auto accident over 9 months ago. She had physical and emotional problems...

Vicki's Desires

by Joancdnj on Sep 15, 2017
Illustrated

"What are you wearing Vicki?" Kevin's commanding voice always caused Vicki's subordinate desires to quickly take control of her mind. Even though his voice came out of her laptop computer speakers from her internet phone connection, today was no exception. "Just what you told me to," Vicki obediently replied to Kevin's question. Their relationship had sta...

Graduation and... Ch. 09

by D.C. Roi on Sep 16, 2017
Novels and Novellas

Heidi Tate sat alone in the living room of her home, feeling extremely depressed. Her life was in chaos. Her marriage was falling apart and would likely end in divorce before too much longer, but that wasn't the worst of Heidi's troubles. A few days earlier, under the sway of emotions she still couldn't understand, she had seduced a young man named Bobby Dra...

Guardian Devil

by fgmntfmgnshn on Sep 13, 2017
NonHuman

Edited by: nancyharpman17... Thank you as your additions are what kept this from being mindless drivel. * Faith. Intuition. The comforting feeling that a higher power is offering a helping hand to navigate life. These phenomena lend credence to the truth that we all have guardian angels assigned by Destiny to watch over us in times of need. But what we ne...

Au Naturel

by leto423 on Sep 14, 2017
Erotic Couplings

Definition of "au naturel:" adj. or adv. 1. in the natural state; outdoors. 2. naked; nude. Recently, I was reminded of my love of the outdoors and, of course, my fondness for engaging in sex in that setting. Why? My first thought is the feeling of freedom one has outdoors. It's a sensuous setting sanctioning sexual sharing free from stifling the sounds of...

"I bet..."

by Jake_Knight on Sep 19, 2017
Erotic Couplings

I admit I'm not the sharpest tool in the box. I can't say I was surprised when I got to Ed's house at 8 when he had said 9, and I'm not in a good mood when I'm awakened early. Finding that my buddy wasn't home worsened my mood. "I bet that guy is a hello kitty fan." "Fuck off, Bree," I mumbled, "this stopped being fun when I was in high school." "No, no,...

Molly the Hooker

by fiscalcelery1 on Jun 19, 2019
Erotic Couplings

10,000 Euros. The sum seemed extraordinary, but that's what Molly needed to get back home. Molly Xiu was an attractive, bright, co-ed attending Houston University. Barely 19, she had a petite, yet sexy figure. She was 5'0 flat, and had a modest chest, as most Asian women did, but a plump, ripe ass that was to die for, toned by many years playing Frisbee. S...

High School Again? Ugh! Ch. 03

by JoeDreamer on Apr 3, 2019
Novels and Novellas

"Hey John, nice game," Pamela Stevens said as I passed her in the hallway. "Thanks," I smiled. "Yeah, way to go!" some guy added. "It was a team effort," I said, and it was the truth, but it was nice to be appreciated, especially after yesterday. Pop had heaped the chores on me for getting in late Saturday night after the game. I spent all day Sunday wo...

Why, Of Course You Can!!

by stfloyd56 on Sep 12, 2017
Erotic Couplings

It was a small town, so small that my new job there became something of a topic of conversation at Nan's Café, the Federated Bank, and the Quick Trip, which was pretty much the extent of downtown Fair Oaks. I wasn't altogether comfortable with that kind of attention, but from what one of my new colleagues was about to tell me, the reviews were overwhelmingl...