Tricked Into Sissy Stories

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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...

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...

Family Chastity Story Ch. 04

by antares34 on Aug 13, 2019
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. ***** My girlfriend Christina has been staying with me for the past sev...

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...

The Neighbours Situation Ch. 03

by Missclo on Oct 8, 2019
Transgender & Crossdressers

I tugged at the bow and it fell lightly to either side of the large box. I slowly removed the lid, terrified of the contents, which felt ridiculous but based on previous events I knew I wouldn't be keen on whatever was inside. There were multiple bags with pink numbers written on them. I opened number one and found a note which I grabbed and began to read....

My Teasing Hotwife Ch. 04

by footslave85 on Mar 25, 2019
Fetish

Part four -- the evening out I look down and see a small dainty gold chain with a little item hanging off it. I wince as I see that it's not the key to my chastity cage but a symbol, the ace of spades, which signifies her status as a hot wife who enjoys the company of black men while her husband is caged in chastity. She can barely hide the giggle from her...

Mistress Commands Me in the Office Pt. 04

by Tracy69 on Dec 3, 2019
Transgender & Crossdressers

Continuing Cast of characters: Bob, or Robert, or Dick (or whatever Mistress decides to call me): Me Rick: My boss Brad: An office co-worker, loves to get on my case Sharon: A pretty co-worker Jim: another co-worker, very cocky and arrogant David: another co-worker, pretty suave, the women all like him Rod: Office co-worker in an adjacent cubical, ver...

Sissy for Mommy's Nipple Cream Ch. 04

by ppeaks42 on Feb 11, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Jaime clasped a hand over her mouth in horror, but it was too late and she knew it. Chills ran down her spine as Julia sauntered over with a wicked smile, then opened the door to reveal her sissy daughter sitting there wearing nothing but her lacy panties and her steel clitty cage...

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...