Sissy Teen Stories

16,707 results
Orientation
Length
Source
Infinite Scroll

Money Shot Pt. 02

by GavinIsaNuisance on Jul 27, 2020
Transgender & Crossdressers

This story is entirely fictitious. Any similarities to persons or things living or dead is purely coincidental and completely unintentional. All persons depicted in a naked/sexual nature are 18 and up. Tanya introduces a newly sissified Danny into the world of erotic photography which gets them into a hot offer they can't refuse. Author's Note: So, I establ...

Eve Quest Pt. 02

by JJ Neal on Sep 19, 2017
Transsexuals & Crossdressers

Chapter 6 I tossed and turned all night sleeping for short periods, but afraid I would oversleep or that the clock wouldn’t go off. About 4:30 I got up. I reasoned I’d need some extra time anyway so I got started. I sat on the toilet thinking about my douche. Somehow a douche seemed so much more acceptable than an enema. I tossed my gown on the bed and fill...

Keith's Caught in a Costume Pt. 02

by gaildaniels84 on Dec 24, 2019
Transgender & Crossdressers

Keith steered his car into the parking lot of Northmark Mall and into a parking spot. Then, his hands returned, zombie-like, to the steering wheel, and he stared off into the distance. He couldn't believe what had happened. He'd got caught, rubbing his dick, dressed in a cheer-squad uniform, by the hottest teacher at his school. She'd humiliated him, made hi...

The Perfect Age Ch. 05

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

"Look at you. You're beautiful, honey." She sits on the couch and stares at me, a big smile on her face. "You're the daughter I never had." She laughs, looks adoringly at me. I'm wearing a short soft tight-knit pink off-shoulder dress. White short stack heel summer shoes with ankle straps that show off my pink toenails. And under it all white satin pantie...

Panty Posers Ch. 03

by EROTICbearscribe on Sep 14, 2020
Transgender & Crossdressers

It was early on Sunday morning. I awoke needing to pee and slipped out of bed, doing my best not to wake Daphne. I could hear him breathing deeply next to me most of the covers on his side as usual. My roomie was lying on his stomach, his head under his pillow. He looked so sexy lying there. I felt the warm rays of the sun on my back as I breathed in his cu...

Lois Lane's Night Out

by exxxidor456 on Aug 13, 2017
Fan Fiction

As with all my stories, I welcome other authors to add chapters! Remember to like and bookmark your favorite chapters! Regular chapters with 5+ likes get a sequel, chapters with 10+ likes get two. End chapters get an epilogue with 10+ likes. Chapters with the most likes & bookmarks get updated first! All characters in this story are at least 18 years old...

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Sicily's Lesbian Son Pt. 02

by SubtleDeviance on Jan 29, 2020
Transgender & Crossdressers

Story contains themes of crossdressing, feminization, incest, and anal play Dante awoke with a little tent in his white lace panties, excited about the day to come. He smiled to himself and stretched across the clean white sheets, wearing one of the babydolls his mother bought for him, sheer, white and sexy. His bed had been the only place he could safely...

Panty Posers Ch. 05

by EROTICbearscribe on Oct 5, 2020
Transgender & Crossdressers

I certainly wasn't in Kansas. I was dressed as a private school girl tease and standing in front of an adult bookstore superstore. What did my sissy sister have in mind? I tried to find some sort of hint but his poker face offered no clues. We were certainly dressed for more than just shopping for DVD's. So I didn't think we were there for the sales. We ha...

Ian's New Job Ch. 02

by SatinSlip on Dec 10, 2018
Fetish

Authors note- this story includes non-consensual, rough, and coerced sex. As well as straight and bi-sexual sex, crossdressing, and humiliation. ********** Wendy wore the shortest skirt she owned. A blue, pleated thing that stopped a few inches short of her knees. Underneath she wore red lace panties Ian had bought her for valentines a couple years ago, an...

The Ice Queen

by The_Technician on May 15, 2019
Transgender & Crossdressers

A wimpy young man finds his place in life when he is invited to go on Spring Break with the Ice Queen. This is a gay / trans story involving Female domination, Female-male sex, male-male sex, and male-Female oral sex. = = = = = = = = = = = = = = = = = = = = WARNING! All of my writing is intended for adults over the age of 18 ONLY. Stories may contain stron...