Tricked Into Sissy Stories

348,985 results
Orientation
Length
Source
Infinite Scroll

Sissy's Journey: The Cocktail Party

by IndianaSissySub on Jun 8, 2020
Transgender & Crossdressers

Brett was an attractive boy with a swimmer's build in his late twenties with short dirty blonde hair, clean cut in appearance with soft features and a chiseled, toned but slender body. He had been busting his ass since high school trying to make a name for himself as a musician, but as more time had passed without landing that elusive record deal, he began t...

She has a dick!

by AdamAK on Apr 3, 2018
Transsexual

I'm John. just an 18 years old typical guy. I go work out from time to time, which keeps me fit, but I'm still no where near bulky. You can actually say that I'm skinny. I never thought about dicks. Thinking about it now is simply weird. I don't know. I just love women. Although I'm a virgin. It's kinda shameful when I think about it. Although I had a couple...

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Beta Male Slave Academy Ch. 01

by Tazokm on Jul 13, 2020
Fetish

My head was still spinning. I kind of heard what was going on, but not really. "Right, Patrick?" my girlfriend asked me. I had completely zoned out. After an hour long car ride to a large compound in the middle of nowhere, I had time to contemplate what was going on. Still, my girlfriend telling me she wanted to have me trained to become a slave was very pu...

Runt of the Litter

by grimbous on Oct 9, 2017
Transsexual

(This story involves a lot of humiliation of the main character, futa on male action, incest, and other fringe fetishes. If these aren't your thing turn back now. I also wanted to give credit and thanks to the artist Mafen for the above picture which helped inspire this story.) The hall is quiet. You were pretty sure nobody was at home. You creep carefully d...

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The Writer's Secret Ch. 07-08

by AnnMichelle on Sep 16, 2017
Transsexuals & Crossdressers

Synopsis: Loren had no idea what he was getting into when his agent suggested he write transvestite fiction. Nor did he realize how eagerly his wife Stephanie would embrace the idea of feminizing her husband. How far would they go? Chapter 7: Laura Buys Shoes. . . Lots of Shoes Loren rolled out of bed the following morning. He yawned. Despite having sex w...

Her Mother's Place

by onlyforher on Sep 17, 2017
BDSM

It was a typical overnight trip to my old co-worker's house. She had invited our family up to spend a night at her home in the northeast. She asked if it would be ok if we shared the weekend visit with her daughter Missy from out of state. We were excited about the weekend and the prospect of spending time together. A few things about Missy. Like us she has...

Ride of My Life

by Tomsparty on Sep 13, 2017
Transsexuals & Crossdressers

As a student at college I wanted a bicycle for Christmas. I hadn't past my driving test and even if I had, I couldn't afford to run one with my Saturday job wages. My parents didn't have much money so I didn't ask for an expensive model by name, anything would do. I didn't think they could go far wrong or could they? They did attempt to wrap it with some f...

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 Visitor Ch. 09

by Leanne_sissy on Sep 26, 2017
Transsexuals & Crossdressers

This is the continuation of the story of my foolish submission to an online Master, who actually became my visitor and all the things that happened as a result. It describes how I slid further and further under his control, by his use of drugs, heavy persuasion and as he is a doctor, the changes he made to my body to prevent my escape from him. This particu...

Young Master Ch. 05

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

I was running through the mansion, being chased by something so horrifying that I didn't dare to turn around and see what it was. I tried to find my room, but the once familiar hallways were now disjointed and strange, as if the building had be rearranged and some pieces had been replaced with imitations that had a sinisterly artificial look to them. My purs...