Teen Sissy Stories

16,707 results
Orientation
Length
Source
Infinite Scroll

A Look Into My Mind: Uncle Sissyboy Ch. 03

by rickiee_2002 on Sep 25, 2017
Fetish

Shortly after I drifted off to sleep, I was awakened by the feeling of something hot and wet hit my body. I looked up and noticed one of the male subbies had just squirted his cum on my body. My negligee had ridden up and the cum was on my side and dripping off my side and onto my stomach. I looked up at him and he just got up and walked out of the room. Lau...

Mother Dear Pt. 09

by keptsissy on Sep 13, 2017
Fetish

"I love this place, baby boy. Every time we dine here I think back to that one fateful dinner, the dinner where this all began. The dinner after I came to your home unannounced innocently enough, wanting to take you out to eat only to find you dressed like a girl and on your knees doing what we bad girls do, delightful." She winks at me over her wine glas...

March Madness Ch. 09b

by jbirdman on Sep 13, 2017
Transsexuals & Crossdressers

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), teasing & denial, chastity training, mild bondage, creampies, cuckolding cross-dressing and a few other fantasies of mine. I hope you find it entertaining, but if you might be offe...

Sissy Auction

by davine on Sep 26, 2017
Transsexuals & Crossdressers

Authors note: this story is a fill in while I get over a block with the fifty shades part three. I also need to revise part two of sissy downfall as Literotica rightly pulled it due to excessive violence. I wish this story was autobiographical. It's not but has some elements of truth in it. I hope you enjoy reading it. I love feedback; even negative. All cha...

Teen Cocktease Babysitter

by CharlotteUnicorn on Jan 22, 2020
Fetish

What a day! Project meetings all day long, from 9am to 9pm, with really intense demo testing, barely half an hour for lunch, and I was on point for the whole day as the lead system analyst. I was sooo tired when I got home. Opening the door, I hoped my kids were asleep and there would be no crises to deal with. I couldn't hear a sound. Yay! April had co...

Cyber Sissy Ch. 05

by missvicky53 on Sep 25, 2017
Fetish

A fantasy by Miss Vicky Part 5 (The Last One) The rest of the evening passed with the two of us cuddling on the couch, each with a glass of wine. Megan had changed into a black floor length nightgown with a lace inset running diagonally across the front. This meant that with each movement of her body, I would catch a glimpse of various parts of her body. T...

Sissy Prince: Origin Ch. 01

by SatinSlip on Feb 6, 2018
Fetish

Prince Oliver skipped through the castle garden. He loved the green and the flowers. He was nineteen and yet to be married. In truth his parents had coddled him as a boy. He knew his numbers and letters. He knew how to run a castle and a kingdom. On paper anyway. But he would never be a warlord. Never be a brave leader of men on the battlefield. His gold...

Caught in Her Panties Ch. 02

by Knightofround on Sep 16, 2017
Transsexuals & Crossdressers

This is a fictional story as was part one. The content of this story may not appeal to everyone. It includes female domination, crossdressing, strapon, lesbian, gay, and such. Just keep in mind that it is fictional and should not be taken seriously. Otherwise just enjoy the read. ***** It has been almost a month since my wife Mary discovered my secret. She...

Sissy Prodigy Ch. 01

by daisyboi_sissy on Sep 15, 2017
Transsexuals & Crossdressers

If you are offended by sexual content please leave now. This is a work of fiction. Everyone in this story is above the age of 18. Thanks for your comments and ideas for future content. * "I have no idea what you are doing, and I don't want to know Kel. All I know is that something is going on while I am not here and I ought to call the school to have his...

The Perfect Age Ch. 01

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

I'd just turned 18 and it was high school graduation. Most of my graduating class was at the raging pool party at my best friend's house. I lived next door to him and his parent's house was the place to be that day and most hot summer days. I didn't think much about the fact that his dad kept talking to me about 'the future' or that he seemed to be around wh...