Sissy Teen Stories

16,707 results
Orientation
Length
Source
Infinite Scroll

Dominating Ken Pt. 01-04

by oneguy4fun on Sep 26, 2017
BDSM

Part 1: The Online Encounter Story Overview A thread of e-mails quickly blossoms into an erotic relationship of domination and humiliation between Ken and Karena. Karena develops a growing need for power and control while Ken finds himself drawn into a state of submission and inferiority. * Ken anxiously opened his e-mail to see if Karena had responded...

Letter from New Piedmont

by justincbenedict on Feb 7, 2018
BDSM

Dear Shoeblossom, I can still remember Rebecca's first comment: "You sure you want to do this, kid?" A full-figured ash blonde with brightly glossed lips...pure Jersey girl. "You really want to move in with me...the sessions aren't enough?" Sometimes the sessions were way too much, but I was lost without Mistress Rebecca. 46 to my twenty-three, she'd bee...

Strawberry Milk Pt. 05

by Sissyhalo1 on Nov 2, 2020
Transgender & Crossdressers

Only Billy was not at the gym. He was in the apartment building next door and I met him using our laundry room. And Billy was right up my alley as it were he hit all my sexy guy buttons. Tall, like really tall six foot six, big and muscled. And a big dick. A dick big enough that as soon as I saw it through his sweats as we did laundry one day I wanted it i...

Twenty-Two More Questions

by silkstockingslover on Jan 20, 2020
Reviews & Essays

Twenty-Two More Questions Summary: 22 questions asked by readers answered. NOTE: Thanks to Tex Beethoven and Robert for editing. I wrote the essay Twenty Questions in December 2017 and Twenty-one More Questions in 2018. I answered the following questions, in case you want to read them. 1. Are you really a teacher? 2. How often do you wear nylons? 3. Wh...

On a Scale of 1 to 10

by His_fag_wife on Apr 17, 2019
Transgender & Crossdressers

He couldn't help himself, it was a new office environment for him and she truly was stunning. Even her little sister Claudia was delightful and sexy, but in a more understated way. The fact that she worked for Georgia her sister, set the hierarchy, but even more so, Georgia towered over her younger sister, and then there was Georgia's innate sense of style a...

Anklet Adventure Pt. 02

by dometoo on Oct 29, 2018
Interracial Love

Day two of our cruise started with the sun shining through the open balcony slider and a slight, warm breeze dancing over our naked bodies. The rhythmic sound of waves breaking against the hull was memorizing, almost hypnotic. My beautiful wife of 20 years and I lay exhausted on the cum stained sheets she and her bull made without me last night. We were both...

Teen Boy Becomes a Girl for his BFF Pt. 03

by SissyKelly on Dec 5, 2017
Transsexuals & Crossdressers

I was fucking stressed. After fucking me in the ass and filling me with cum at his house, then cumming all over my face at the tree, me and Ryan hadn't had another chance to hook up in weeks. Sure, we still texted and exchanged photos and jerked off to each other like crazy, but since my parents divorce that was harder to do as my mum gave me little privac...

A Sissy's New Daddy Ch. 03

by sissyneko on Oct 8, 2019
Transgender & Crossdressers

I hope you enjoy this third chapter of "A Sissy's New Daddy" I hit a bit of a speed bump with this chapter, I wasn't sure where I wanted to go with it. I think I have that settled now. I am foreseeing this as a 9 chapter piece with the next three chapters jumping ahead a bit in time. I hope you enjoy this chapter, and if you haven't already please give the f...

Pretty in Pink Ch. 03

by jealouscuck on Sep 18, 2017
Transsexuals & Crossdressers

After our trip out of town, Jessica and I had an even better sex life, if that was even possible. One night we ate out as man and wife and she made me stop at a dark, lover's lane type place. I had not really noticed before, but she had dressed rather conservatively. I just assumed that it was some of her new work clothes. When we got parked, she said, "Oh,...

Sissy Plays the Game of Thrones

by SissyKelly on Dec 1, 2017
Celebrities & Fan Fiction

Kelly Waters, fucking Waters I thought to myself as I shook my head. I think the worst part of being a bastard is knowing you could choose any last name, but having it dictated still by birth. I knew not who my parents were, in fact I only knew I was Kelly Waters thanks to the man who raised me, Lord Petyr Baelish. I was born in his house, his whore house,...