Tricked Into Sissy Stories

1,000 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com

It?s Either Break Up Or Make Up

by felicia_rene on Sep 12, 2017
Transsexuals & Crossdressers

PART 1 Synopsis: I always was put off by the unsuspecting stupid love sick, pussy whipped guy is transformed against his will because the will wants to run off and have an affair, I never understood why they don't just pack and leave. The underlying theme is transformation and sexual punishment of the main character with anti gay womanizing feeling for hi...

Afro Stress Relief Ch. 05

by llts1970 on Aug 1, 2018
Transsexuals & Crossdressers

My alarm went off the next day, my mouth and asshole ached, it was going to be a long day I thought. I had put plenty of grease up my asshole just to ease the soreness but it still felt pretty stretched. I started to remember last night, I couldn't believe I'd taken Baba G's fat black penis in my mouth, or that I'd spoken to the police officer like that! I w...

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...

April Fool Office Sissy

by lululuvsblack on Apr 10, 2018
Transsexuals & Crossdressers

"Dear Colleagues This week, in order to help with our efforts to raise money for charitable causes, we have decided to mix up our usual policy of dress down Fridays. This Friday we are instead instigating a "dress up Friday" in which staff are strongly encouraged to come to the office dressed in the office attire of the opposite gender (that's suits and tie...

Sissified by Hypnosis

by Subkoksukr4u on Jul 16, 2019
Fetish

Reaching with just his tongue he licked the Big Black Cock in front of him. She was behind him, watching and fingering her moist pussy, reveling in his submission. He tasted the salty precum and let it linger on his tastebuds. It was his first cock of the night and he wanted to please his mistress. Being submissive did not come naturally for Matt or as he...

Tricked Into Love

by bluegiraffe on Sep 14, 2017
Erotic Couplings

I was looking through the internet personals to pass the time, although deep inside, I was actually desperate for a date. My name is Mike, and I was a 21 year old guy in college studying sociology. I wasn't bad looking or anything but just a little shy. Usually, the personals were just full of kids putting fake postings or unattractive women who couldn't ge...

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...

Mistress de Sade's Sissy School

by spitzharder on Sep 16, 2017
Transsexuals & Crossdressers

My whole body hurt, everything, both inside and out, the pain had brought me agonisingly awake. I could feel the bars of the cold cage I had been thrown into, it had been my home for several months but the beating was new. The other sissies had turned on me, they might be 'girly' but they were cruel, Mistress Kayne had warned me that to disobey one last ord...

The Photographers Assistant Pt. 02

by panty_wearing_sissy on Nov 13, 2017
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 is only suitable for persons over the age of 18 mature enough to understand, and distinguish the difference between fantasy fiction and real-life. ***** Jake didn't remember e...

Lust Thy Enemy

by Lady_Blackhawk on Sep 14, 2017
Sci-Fi & Fantasy

It had been hours since Callia slipped into the lodge that was the residence of her clan brother, Amakiir. Bearing no close blood ties, she felt no remorse for what she planned to do. Revenge for the hell he had subjected her through during her youth coursed hotly through her veins. Recalling the stealth lessons learned from the rogues, she crept into the s...