Teen Sissy Stories

16,707 results
Orientation
Length
Source
Infinite Scroll

Rise of the legondery sissy

by monkey17 on Sep 1, 2018
Fan Fiction

Jamie Sonozaki awoke to the sound of hs alarm clcok. Standing at a hight of 5'2" with an hower glass shaped figuer. His messy blond here in a poni tiale and doe green eyes set into a hart shpaed face, maid him look like quit the fukcalbe girl. ONly he was not a gilr. The lack of boobs and a pussy prothed this. thoe to be fere his dick was only 3 inchis...

Open in Reader

Finding My Genie Ch. 03

by jealouscuck on Sep 16, 2017
Transsexuals & Crossdressers

After Genie convinced me to get rid of all my male underwear, she made every effort to compliment me on my panties. She frequently told me how good my ass looked in sheer panties or how great my cock and balls looked encased in feminine underwear. I never felt unmanly or sissified with her. She would buy me some new panties every few months. What she really...

Caught by My Bully and Exgf Ch. 01

by CindyTightass on Sep 15, 2017
Transsexuals & Crossdressers

Dear readers, this my first erotic story, all of protagonists here are fictional consenting adults, I hope you enjoy reading it! ***** I was 21 year old student with part-time job, living in a small flat in big city when this all happened. I broke up with my girlfriend Michelle, after seven month long relationship with her, because I received a video from...

Big Booty Goth BF

by Furry-god69 on Dec 7, 2020
Transsexual

You are Damien Smith a 18 year old high school senior who's really into goth culture, your parents say it's just a phase, but you don't think so. you look like a regular teen save for you're dark hair, and very feminine figure. For as long as you could remember you always a very girly frame, which many people made fun of, except for, Avery, the love of your...

Open in Reader

Futa: The Emergence

by Smithjohnsonian on Dec 13, 2018
Fantasy

Earth witnessed a massive meteor shower in 1950 which brought along with it extraterrestrial life, albeit as unicellular organisms, several of which crashed as meteorites in Central Asian, East Asian and South Asian countries with a few of them landing in the North and the South Americas. These single-celled organisms had a lot of similarities with viruses o...

Open in Reader

Unleashed

by puzziboi on Sep 16, 2017
Transsexuals & Crossdressers

Ray stood up from the chair in the New Millennium African Braiding salon and checked his fresh cornrows in the lengthy wall mirror. He folded off three twenty dollar bills and told the attractive dark-skinned stylist from Ghana to keep the change. She had attempted on occasion to get the six-foot-four-inch, two hundred forty pound brother to get inside her p...

TS Princess Ch. 01: Fucked by My Warden

by TSPRINCESS on Sep 16, 2017
Transsexuals & Crossdressers

It had been several weeks since I left home with my cousin brother for my breast-enhancement surgery. All our family knew was that I was going to some cram-school to get coaching for Pre-Medical Exam (AIPMT). My cousin brother had been supportive of me not only since he cared for me; it was due to his own advantage of having a full-formed girl at his disposa...

The Dog Sitter

by Tosshhh_ on Sep 23, 2019
Erotic Couplings

A few months ago myself and my long term submissive celebrated our 3 year anniversary. We have evolved past our original Dom sub dynamic and are now more or less a couple. For our 3 year anniversary we decided to go away so we got a dog sitter. That was the first time we met Tina. Tina was 18 years old. She was a petite thing with almost no tits. She was b...

The Hardest Kind To Be Ch. 01

by Joe Wordsworth on Sep 16, 2017
First Time

In the offhand chance that you don't find the setting clear on the issue, all characters are eighteen and legal. This is also a madly different story genre than I'm used to writing, so be kind. . . .. ... ..... She hated her. Hated... though strong and dramatic, it was the only word that summed up their relationship. Nobody would have guessed it, but i...

Slow Descent into Sissy-Hood... Ch. 01

by Slipperylock on Oct 31, 2018
Transgender & Crossdressers

Beta boy beginnings. It started when I was online, lonely and drunk. I'd been at University for maybe three months at that point, struggling along with a Masters degree in Economics. Unlike my undergraduate years, I had decided to live alone in a one bedroom flat - I thought that with more privacy would come more focus. What I hadn't counted on was that wi...