Teen Sissy Stories

16,707 results
Orientation
Length
Source
Infinite Scroll

Panty Posers Ch. 04

by EROTICbearscribe on Sep 21, 2020
Transgender & Crossdressers

I must tell you of an experience Daphne and I had one Saturday night. I know, I know. You're dying to find out if I ever finally met Daddy. All good come things to those who wait. I really am a sissy tease. Aren't I? I think you'll enjoy this side trip though. *** It was a lazy Sunday morning. Daphne and I were sipping coffee and nibbling on some danis...

Outed and Married Ch. 03

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

When I entered the room with their drinks on the tray I was carrying I thought I would be pleasing to my husband. I made sure that my skirt was properly adjusted the way he likes me to wear skirts in the house. He insists that my rear not be covered below my tight little hole, insists that he have instant access to it if he wants to use it for his pleasure....

Moving to the Sexworld

by Shendude on Dec 19, 2010
Science Fiction

Imagine an alternate universe where casual & free sex, sexuality, & nudity are everywhere, where all people are at least bi, where there are almost no sexual taboos, where everyone's a nympho or satyriac, and where almost all interpersonal interactions have some form of sexual content, and it has ALWAYS been this way. Now, imagine that this world com...

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The Sissy Models

by neverless on Mar 12, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** "It's not something I've ever done," Daddy said, with a frown though the fact he hadn't laughed it out of hand meant I knew I had a good chance of persuading him. "There's a first time for everything," I answered. "What if someone recognises us, Ricki?" he asked. "They won't"...

Getting What You Want

by lowtouch on Apr 5, 2021
Transsexual

You don't know why they always pick on you, the guys who live in your building. You never give them any trouble when you pass by on your way out the front, where they like to stand in their sweats, either working out or hanging out, but they never let you go without something. Usually it's a just a comment, or blocking your path and making you shuffle around...

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The Photographers Assistant Pt. 01

by panty_wearing_sissy on Feb 5, 2018
Transsexuals & Crossdressers

If you are under 18, please stop reading and delete this document immediately. This story is pure fantasy. It does not relate to any real events, either past, present or future, and only suitable for persons over the age of 18, mature enough to understand and distinguish the difference between fantasy fiction and real-life. All character in the story are ove...

Property of Master Ajax Ch. 01

by TightandWhite on Sep 19, 2017
Transsexuals & Crossdressers

I headed down to the community swimming pool glancing furtively left and right to make sure no-one was around. It was midnight on a Tuesday so there shouldn't be, but I wanted to be sure. I clutched my bag tightly as I reached the changing rooms. To the left, the lady's and to the right, the men's. After glancing over my shoulder one last time and taking a d...

Getting to Know Me Pt. 02

by eviltwin52 on Oct 5, 2020
Transgender & Crossdressers

I was still excited about what had happened yesterday and was so looking forward to meeting Butch again today at noon. The clock seemed to be stuck between 10:30 and 11:00. The morning passed so darn slowly. Remembering my instructions, it didn't matter what I wore as long as I wore some of my sexy underpants. I selected a maroon pair of the full backed bik...

Black Cock Transformation

by Ewriter111 on May 1, 2018
Interracial Love

I turned 18 in the summer just prior to my senior year of high. Although this put me slightly behind others in my class, it made me eligible for the schools summer work program which paid well compared to other teen jobs. The job entailed light maintenance and some grounds keeping which was very easy and best of all the full time maintenance man was recommen...

Property of the Master Ch. 01

by BrightTightandWhite on Sep 26, 2017
Transsexuals & Crossdressers

I submitted this story a while ago under the name TightandWhite however I have forgotten both the password and email address I used to create that account. So this is not plagiarism I'm just resubmitting it. ***** I headed down to the community swimming pool glancing furtively left and right to make sure no-one was around. It was midnight on a Tuesday so t...