Chastity Crossdressers Stories

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Sucking My First Tranny Cock

by SamTravis on Sep 16, 2017
Transsexuals & Crossdressers

I'd been in chastity for 5 days, and my thoughts are not really focused on anything but sex (my lack of it) and sex (my desire for it). Princess Melissa plans on keeping me in chastity for a long time. She says Sunday (4 days away), but I suspect she may be teasing me. She told me I needed to suck cock and swallow some come - TODAY. So while I was at work...

An Obsession

by Marcus_Cicero on Jul 30, 2019
Transgender & Crossdressers

It would have been after that documentary. The one with a feature on online dominance-submission relationships on Fetlife. Because before that moment in time life had been so vanilla. Marcus had been queer and had had a boyfriend or two... or three since turning 18. Well, hell, he'd been to the bathhouses since turning 20. He'd even gone as far as to create...

My Sissy Life

by snorn on Nov 26, 2017
Transsexuals & Crossdressers

I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it. I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...

Oh Boy

by justincbenedict on Sep 16, 2017
Transsexuals & Crossdressers

He'd had to take the job to pay child support for Davina and Dakota...what could be worse than being a probation officer...and then it happened-scandal! How had Norville ended up dating one of his probationers? Norville remembered when the pretty ash blonde with green eyes had come into his office, one long list of priors...forgery, credit card fraud, burg...

Lace and Love Ch. 03

by vaultdweller111 on Sep 19, 2017
Transsexuals & Crossdressers

Jake Orlov grabbed his duffle bag and rifle case out of the cab of his F-250. He had some other gear in the truck, but he decided to get the rest later. He was exhausted from driving back from Kentucky, training the Blackwell county sheriff's department's SWAT team for the past week. Jake was disgusted at how these guys managed to graduate the police academ...

Mistress Aminata Kanu's Dungeon

by Samuelx on Feb 7, 2018
Transsexuals & Crossdressers

As Salaam Alaikum, to any kinky fellow Muslim reading this. Salutations and greetings, ladies and gentlemen. I am Aminata Kanu, also known as Mistress Ka, an expert on BDSM and Black sexuality. I'm a young Black Muslim woman living in the City of Santa Barbara, California. Before we go any further, I must warn you that I'm into some truly extreme shit, and I...

Taken Too Far Pt. 01

by SwitchSissy on Jul 2, 2018
Transsexuals & Crossdressers

I had maybe taken it a little too far. It had started as it always does, a little light crossdressing at home. Then toys as well. Then wearing something a little extra under my boy clothes when I was grocery shopping. Then when I was at work. And that leads me to my current situation. On the outside, jeans, t-shirt – normal enough. Underneath though... It w...

The Pantysissy Diaries Ch. 03

by JPantyboyVSL on Apr 23, 2019
Transgender & Crossdressers

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. To better follow this story read The Pantysissy Diaries Chapters 1 and 2 before reading chapter 3. ***** It was nighttime in NYC, and Jaymie and her 6 Mistresses had just left their apartment to head to Vic...

A Trip to Remember Ch. 03

by marykay9 on Sep 16, 2017
Transsexuals & Crossdressers

Around a half hour later I was on my knees and I was wearing a blindfold. My hands were placed against a full length mirror and my suction cup dildo was attached to the mirror at mouth height. I heard a knock on the door and Judy said to me "Okay, get ready" which meant that I was to begin sucking on the dildo. The door was opened and a man entered the room...

(Cross) Dressing for a Latex Party Pt. 01

by latexlegs on Sep 25, 2017
Transsexuals & Crossdressers

We had been planning the outfit for months, and finally the day was upon us. The outfit was for me, not my wife. I have been a latex fetishist for years and I have slowly been able to bring my wife round to my way of thinking, although she is not as out there as me. We live in South Africa, where latex is scarce and expensive and really hard core fetish...