Tricked Into Sissy Stories

348,985 results
Orientation
Length
Source
Infinite Scroll

From Her Ex-Boss to her Bitch Pt. 03

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

This story contains extreme fantasies of Fem Domme, watersports, cock sucking, forced bi, if these aspects are likely to upset you please do not read on. ***** Pete had been taken in by Rachel, encouraged along the way, with a little titillation and confessions of her bisexuality. For a married man he had admitted too much and allowed himself to be taken f...

Playing Pregnant

by theonewhowas on Sep 16, 2017
Transsexuals & Crossdressers

I'm a sissy. I used to be a femboi, then I was a crossdresser, and now I'm a sissy. The main difference between the crossdresser and sissy phases was the attitude; before I was a guy doing this for fun and to be admired, sexually – to confuse straight and gay boys alike. But now, as a sissy, I was devoted firstly to my master and love, Noah, and secondly to...

Feminizing First Step Ch. 04

by antares34 on Dec 10, 2019
Transgender & Crossdressers

(All characters are age 18+) It has been months since my mom and therapist started my sissy transformation. So many changes have happened! Shortly after placing me in a chastity device, they revealed to me that the "male hormones" I thought I had been taking were in fact just the opposite -progestogen and testosterone blockers to be specific. To be honest...

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...

Chatroom Trick Ch. 03

by ukmaleslave on Sep 15, 2017
Transsexuals & Crossdressers

For those of you first reading this let me fill you in on a Friday that that opened my eyes. I am a 26-year-old normal guy who had for sometime been flirting and playing with an older woman named Mary via an Internet chat room. She was about 41 a firm fit body and gorgeous red hair, perfect, better than that she didn’t live too far away. Our chats didn’t rea...

We Were All Fucked Up By Feminism

by PrinceThelo on Sep 16, 2017
Reviews & Essays

It was such a great idea: equal rights for men and women. Where did it all go so horribly wrong? The problem is that while feminist rhetoric was all about freedom, feminist reality has turned out to be all about oppression. Instead of ridding us of stereotypical gender roles, feminism has forced us all into another set of stereotypical roles that no ordinar...

The Auction Pt. 01

by phoenixcinders on Jun 5, 2019
Transgender & Crossdressers

Sorry I haven't posted in a while. I fell into a slump, but I'm back with a brand new story. All characters involved in sex are 18 or older. This story contains feminization, slavery, anal sex, transgender, sissy, blow job, cum swallowing and vampires. You have been warned. If you don't like the tags, don't read it and move on. Other than that, feel free to...

You're Like a Little Boy at Times Ch. 02

by Myneed on Sep 13, 2017
Fetish

This is the continuation of a slightly twisted femdom love story that make most sense if the chapters are read in order. The characters don't seem to want to engage in safe sex, but in the real world we should. Enjoy. All characters are over 18. ***** It was a long week for me. I wasn't surprised when Mel didn't call. It made sense that we needed some t...

A New Life Ch. 05

by sissycinnamonswirl on Sep 18, 2017
Transsexuals & Crossdressers

I remember that night I drove myself home from work after getting her phone call filled with humiliating demands and insinuations. I was in an absolute panic. I had no idea if Mistress Sally was serious about all of this, or if she was just playing elaborate games with me. But I honestly feared the worst, and my fears were realized as I pulled into my drivew...

Haven the Sissy Slut Ch. 02

by CSK on Sep 11, 2017
Transsexuals & Crossdressers

As the water poured over me, washing away the remaining cum and pee from my young, nubile body, I stood up and removed my drenched clothes placing them on the floor of the shower. I grabbed the girly body wash and lathered my body down, making sure every inch of my man-pleasing body was squeaky clean especially my "pussy" as I was positive it was going to be...