Teen Sissy Stories

16,707 results
Orientation
Length
Source
Infinite Scroll

Sissy Prince: Origin Ch. 03

by SatinSlip on Feb 13, 2018
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** Olivia pulled off his scratchy wool tunic. It had covered him to just below his cute girly ass. It was uncomfortable to wear, made by Orcs. Yet for some reason it turned him on. His tiny sissy bump was now revealed to the world. It was erect, yet not quite two inches long. He...

Benns Feminisierung

by Racsomann on Apr 6, 2020
Amateur

So richtig Lust hatte Benn nicht auf den Geburtstag seiner besten Freundin. Sonnst waren nur Mädchen eingeladen. Aber er mochte Lisa, also ging der 18 Jährige am Freitagabend auf die Übernachtungsparty.What's next? Die Charaktere Aller Anfang ist Schwer What's next? Die Charaktere Aller Anfang ist Schwer...

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On Line and Linda

by vinceh23 on Sep 16, 2017
Romance

Linda and I had met through one of those ubiquitous on line dating sites. When I saw her photo it grabbed my attention. We all have certain characteristics in face shape, eyes, kips, those things we can't necessarily define but when we see them we know immediately that we like that face. And she was tall, 5'9", and though not slender she was not overweight....

A King's Touch Ch. 00

by dragontatto on Sep 19, 2017
Sci-Fi & Fantasy

Thanks to all of those who have been patient with me and the delay for returning to Venus and these wonderful characters. I hope you enjoy and wish me the best during the Nanowrimo contest, which is what I'm writing this story for. * Sandova, Venus, 2108 "Come out child." Clara's gaze was steady on the spot where she was certain she had a little spectator...

Joel Gets Caught by His Wife

by Downforeverything on Sep 18, 2017
Transsexuals & Crossdressers

This is a fictional story written for a fan about their sex life. If anyone else has a story they'd like written for them about fact or fictional events feel free to message me. As always please leave comments or constructive criticism so I can make your pleasure better! * It was Monday afternoon. Joel had taken the day as an opportunity to work from home...

My Sissification

by sissy171 on Jul 6, 2020
Transgender & Crossdressers

Chapter 1 Summer after High school I was a sexual submissive with my very first girlfriend, Mary Jean. Mary Jean had an aura of sexuality; sensual and seductive. All her summer clothes were tight and revealing, and I was drawn to her like a moth to flame. We hung out a lot, and sex was all I wanted to talk about. She implied that she wouldn't fuck me, b...

House Rules Pt. 02

by GavinNuisance on Mar 16, 2020
Transgender & Crossdressers

Terry laid naked on Lana's couch, face down with his ass sticking up. Her cum had dried. Drowsy, and still a bit tired, Terry began to move, and stretched as he adjusted his eyes to light. He noticed the sun was setting and he was clearly there for at least a few hours. He rubbed his eyes, but noticed a peculiar feeling in his backside. "What the fuck?" He...

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...

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Bukakke Sissy/Angel

by hyperpress on Sep 14, 2017
Fetish

He's wearing his favorite outfit. A nylon/spandex blended thong that encased his fullness, shaved and smooth in a delightful caress. A bustier girdle with four straps (he wanted six but the cost was exponentially increased for those two extra straps), and wolford thigh high stockings, his legs and bottom were completely shaved...he was delighted with how fem...

Robin and Jimmy Olsen - Sissies Ch. 01

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

Note that this story stands separate from other stories I have posted. * "If you hunky men will excuse us for the moment, we girls have to go... powder our noses!" Robin said as she scootched around on the cushions of the private booth. Jamie rose and joined her. Their dates watched the two girls' rounded asses sway back and forth as the two sissies walked...