Gender Swap Sissy Story Caption Stories

148,696 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

X-Change

by Noah_Peal on May 15, 2015
Miscellaneous

Pills Pink pills change males to females. Blue pills change females to males. Purple pills (X-Trans) change males or females into transgenders, can be combined with pink or blue. X-Change (Formula subject to change) Acquired from unlicensed "street" vendors. Changed (defective/in testing) formula. Cheapest. High pregnancy risk. Can lead to mental a...

Open in Reader

Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...

Kissing Crossdressers Pt. 01

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

It started when Carla, my hot sexy wife went away on a spa break a few days with some of her girlfriends. Carla is 40 (I'm 48), has blonde hair, blue eyes, 34DD tits and a curvaceous ass. She works long hours in a busy office as a manager, I work in a local library and my job is far less stressful than hers. And her job has definitely taken its toll on our s...

Mastering the Multiverse

by google2020 on Apr 29, 2025

Percy White was many things according to her peers, a nerd, geek, unpopular…… and a genius. It took her several years, but she finally managed to figure out how to create fully functional teleportation device. She had been working day and night, hoping to revolutionize the world around with it, and become an amazing scientist. At least that’s what she hoped...

Open in Reader

Unlimited Online

by Lake_Nine on Dec 5, 2017
Science Fiction

Humans, we are explorers, we yearn deep inside to go where no one has gone before. To tame new lands, to face new challenges, to discover new wonders. Inside each of us is an adventurer. In the real world there are no new mountains, but in UO there is more than you could dream of. New lands, new races, new sights sounds and smells. It doesn't matter who you...

Open in Reader

"Sissified": 12 Days of Sissy-mas

by silkstockingslover on Jan 7, 2019
Transgender & Crossdressers

Summary: Straight man is turned into a submissive sissy by.... Note 1: This is my 400th story release. To mark the occasion, I thought I would try something longer... mixing many of my themes into one long, complex story. Thus be warned that with over 40,000 words, this story is a marathon not a sprint, and it includes a variety of themes including: cross d...

Tales of The Great Shift.

by joshman110 on Aug 2, 2019
Fantasy

On a other-wise average day on planet Earth, a strange **** of energy passed through the planet. This **** was The Great Shift, A supernatural that shifted the minds of 90% of the worlds population into different, random bodies. Say, an 80 year old man is shifted into the hot college co-ed down the street and his old body now has the mind of a twelve year bo...

Open in Reader

Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

Masculinity Lost

by GoldenCone on Apr 22, 2025

One strange day in the midst of the 20th century, a pink star lit up the night sky. From then on, the out-and-out Man has been a fading breed. The star's so-called 'gender-rays' disrupted the natural sex and sexuality of the human race, and some generations on the terms 'man' and 'male' are practically gone from the English language. Nowadays, young boys gro...

Open in Reader

Virus S

by thisisnttaken8 on Jan 17, 2021
Bisexual

"FUCK ME YOU STUD!" the slender new trap screamed in agonizing bliss as the muscular stud pounded him from behind. Connor could see the brute's body changing by the second. He arms grew more muscular and his jaw grew more angular, but even stranger was his cock. It seemed to be growing thicker and larger as he plowed the twink's ass. The bull wasn'...

Open in Reader