Tricked Into Sissy Stories

348,985 results
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Infinite Scroll

How I Became a BBC Sissy Slut

by Satanicsissybitch on Feb 12, 2019
Transgender & Crossdressers

I wasn't always a black-owned little slut if you can believe it! Can you believe, at one point in my life, I actually refused to sleep with black men? I can't even wrap my head around it honestly. These days I belong to a number of hung black guys who use me whenever they want and now I refuse to sleep with white guys altogether! If it's not a black cock I d...

A Photo Session, My First

by keptsissy on Sep 18, 2017
Transsexuals & Crossdressers

When he called and said "We're going to something special today, sissy boy." I got instantly wet in my panties. He arrived at my house and stripped out of his clothing almost before I had a chance to close the door. I feel his large hand cup my penis and balls. He covers them completely and easily. I'm small, less than 3" erect, baby-like. I feel my little...

Finding Claire

by Sissyhalo on Nov 26, 2017
Transsexuals & Crossdressers

*Before... I get cleaned up and instead a drink I have a big mug of coffee and a long, long shower. Thinking on all of it a lot. Then I check my bank accounts twice online. I go outside after slipping into sweats and walk around my house and the yard and the garage, the big barn one out back. It's my second house here actually with Roxanne getting the f...

The Dragon Ring Ch. 07

by Beatnic_jazzman on Sep 25, 2017
Sci-Fi & Fantasy

I saw place names and looked to find mine; it was on the left front. On the right front where I expected to find Sissy's was the coat of arms of the S'snoyme kingdom with the legend of 'Giver of the Bride'. I was horrified. I grabbed the marker and rushed double time to the reception room. I spotted Antic and rudely took his arm. "This is an abomination!"...

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...

A Freshman's Summer Class Ch. 07

by CapnSteelBoy on Jun 1, 2020
Transgender & Crossdressers

A Freshman's Summer Class **All characters are of legal age for adult content.** We Continue from where we left off with our brave hero, as his adventure continues during his summer of higher education learning! This is a continuing series I'll be releasing as my busy editor(s) help me clean up my keystrokes of mess.. Much thanks goes out to them, as th...

On Your Knees Ch. 09

by JinkiesFarie on Sep 16, 2017
BDSM

*Note to readers: Changed Victor's last name to Frost* Victor awoke groggily on a cold, hard floor. His memory was a blur to yesterday's events, when he first came to he thought he was on Nicole's floor being punished. The air was stained heavily of piss and booze. His body ached all over, his head throbbed in particular. He struggled to sit up, only man...

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...

Sexy Slut Fantasy Ch. 04

by pdavis616 on Sep 15, 2017
Transsexuals & Crossdressers

The story continues with Sasha and Nicole heading to the sex shop As I sat in the car waiting for Sasha to start driving I pulled the mirror down to take a look at my face. As I glanced in the mirror I saw the strange beautiful woman staring out at me. I licked my lips and gave her a sly smile and I was really surprised to see how good it looked. God I can'...

Caught by the Past Ch. 03

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 3 - Friends United Previously - When you dressed as a sexy tart for James he showed two sides to his character. Bent over his knee, stuffed with a butt plug and forced to suck his cock. What more could he possibly do?... Read on After sucking his cock you sit on the sofa supported by a fluffy white cushion, shoes kicked off, legs curled under your...