Boys Become Sissy Sex Toys Stories Stories

286,457 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Sammi Starts Camming

by Sissy_Sammi_ on Dec 3, 2017
Transsexuals & Crossdressers

Sam had always been rather small and feminine. As a guy puberty seemed to have missed him which left him in the rather uncomfortable position of being very girly. He was only about 5'8" with a womanly rounded face, smaller waist, and slightly larger hips. He had brunette hair, which for a guy was on the longer end. His lightly tanned white skin pieced with...

Introspection

by Sissy_Sammi_ on Jun 19, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. *** *All characters are 18+ years old ***** Jimmy was born into a small family in Colorado. His mother was a beautiful woman named Dianne, and his father was a gruff working man named Thomas. If only kids could have been given a choice to be born, Jimmy would have chosen otherwise. He...

Panty Posers Ch. 02

by EROTICbearscribe on Jul 6, 2020
Transgender & Crossdressers

NOTE: This is a work of fiction. The characters appearing in this series are consenting adults over the age of 18. Any reference to past experiences by any character appearing in this story are intended to define that character. * It was almost 3 when I woke up in my roommate's double bed. Sunlight streamed between the broken slats of his plastic blinds...

The Locker Room Glory Hole

by Sissy_Sammi_ on May 30, 2018
Transsexuals & Crossdressers

*All characters are 18+ ***** The bell rang, rousing all of the students out of their seats. The students stuffed their books, binders, and pencils back into their bags before quickly rushing out the door to get to their next class. It was going into seventh period, the last period of the day for everyone without an after school class. Most students quickl...

Secret Makes Him a Cuckold Bitch

by Subkoksukr4u on Jul 29, 2019
Fetish

Getting caught doing something kinky or sexual for some people is a turn on, for others it's humiliating. There's lots of different variations. Like when you get caught doing something with another person or get caught doing something by yourself. Anyway way you slice it, getting caught can be embarrassing to some degree. This story is about someone finding...

Wesworld: Candy's Interview

by gaildaniels84 on Dec 25, 2019
Transgender & Crossdressers

This story is inspired by a series of captions done by Wes Mantooth over on his blog. Wes has been gone for several years and I'm a huge fan of his work so my intent is to use several of his stories and characters as jumping off places to create a larger world. *** Cameron once again ran his hands down the front of his pants, trying surreptitiously to wipe...

A Busy Day Pt. 01: An Oral Surprise

by nadia603000 on Oct 6, 2020
BDSM

Author's Note: Mistress Pepper and Sophie are "anonymized" versions of me and my slave-girl. The real me. All of my stories are (or should I say will be) my memories of a session with a sub. Thus, they are true stories. Only in this version details have been changed to protect the sub. I do live in Mobile about 10 months of the year (the remaining two I spe...

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...

Big U Pride Ch. 03: The Squad Forms

by latinarita4 on Jul 27, 2020
Transgender & Crossdressers

Remember to check on parts 1 and 2 before you read this! Also, please rate and review my stories! I love hearing feedback from readers! If you have suggestions, just send them right along! Maybe your suggestion will be featured in a future chapter... ________________ Most days at the campus health center were typically light affairs. Usually it's the rout...

He Changed Me

by Sissyhalo1 on Dec 23, 2019
Transgender & Crossdressers

I know a lot of these stories are about some guy that watched porn or read it and got hooked or were some short femmy guy that got tricked into getting boned but that's not me. I'm Sam and yeah it's Samantha most of the time now. But before that it was just Sam and I was in my last year in college and to save money to fix my car I moved into a rental house...