Crossdressers Chastity Stories

18,166 results
Orientation
Length
Source
Infinite Scroll

The Sissy and The Gardener

by snorn on Sep 16, 2017
Transsexuals & Crossdressers

As I sit in my office, I am wearing my pink sissy uniform, watching the hired gardener dig up the weeds out front. I'm not supposed to expose myself to others, but my sissy rules state that I must be in uniform when nobody else is inside the house. I'm doing work, but all I can really concentrate on is the idea that I should be on my knees sucking cock, or b...

The Pantysissy Diaries Ch. 02

by JPantyboyVSL on Jun 5, 2018
Transsexuals & 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 Chapter 1 before reading chapter 2. *** The Amtrak train Jaymie was onboard with his new Mistress, Sydney had just pulled into NYC. Jaymie had to get...

Mamma Mia - Forced Femme

by ppeaks42 on Sep 16, 2017
Transsexuals & Crossdressers

"We need a little more feminine energy around here." The words hung in the air as Tommy's devoted licking of Mia's ass slowed to a stop. "You mean another woman?" Mia hooked her legs behind Tommy's head and pulled his face back into her ass. "No, I mean you, you dumb sissy bitch." Once Tommy finished with pleasuring Mia, she led him into her closet. She...

An Ever Changing Life Ch. 03

by Helenthemaid on Sep 16, 2017
Transsexuals & Crossdressers

Previously.... After several years, I was completely in their command, and when feeling particularly cruel they would invite several of their female friends around and introduce me as Jennifer, a cousin visiting for the weekend. Very soon I was getting invited to lots of girlie parties and events. Julie and Janet made sure I accepted every invite. I was alw...

Sissy Slave Fantasy

by tinkerslut on Sep 13, 2017
Transsexuals & Crossdressers

A fantasy written to my mistress.. Sissy kneels before you, her eyes down, waiting on your pleasure. Sissy is wearing frilly panties with a matching bra, thigh high black lace stockings encase my legs. The red dress barely covers her smooth bottom. The high heel shoes, locked on my ankles, crossed behind me. I can't speak because of the ball gag in my mouth...

My Secret Revealed Ch. 05

by jealouscuck on May 30, 2018
Transsexuals & Crossdressers

The trip to New York was indeed the watershed moment in our relationship. Karen was showing me off as her submissive husband. I could have been resentful of the way she had me come out, but I was enjoying the excitement too much to complain. She had made such a show of chastising me when she found out about my fetish because we were not to have secrets from...

PVC Sissy Whore

by Dostoyevshe on Sep 16, 2017
Transsexuals & Crossdressers

One day I was bored and horny so decided to cruise around a local adult store and find some action. I squirted a good amount of lube into my ass, slipped in my favourite 3 ball butt plug and put a pink chastity cage on my tiny cock. I wore hot pink lacy panties and bra, a tight PVC miniskirt, high heels, a pink jacket and heavy makeup like a whore, complete...

Being Chris's Slut... Pt. 01

by usemetoday1962 on Jun 25, 2019
Transgender & Crossdressers

Chris had now decided that when we played he wanted me to be his slut. He had inherited some money and decided to purchase a small home. He knew i could help him do work in it so the house he brought had an unfinished basement. First thing he wanted was a wall splitting it in two so one side could be a play area and the other a mancave. But instead of a door...

His Sissy Bitch Ch. 03

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

"You've come a long way, baby." He smiles at me, watches me as I cross my legs. I'm sitting across from him. I can tell the effect I have on him, every time he visits, sees me dressed fem for him, he's hard, rock hard when I meet him at the door. And I know what outfits turn him on the most. I know he fantasizes about me when he's fucking his wife. She doesn...

Slow Descent into Sissy-Hood... Ch. 02

by Slipperylock on May 11, 2020
Transgender & Crossdressers

I started pretty slow. I'd wear it for at first hours, then a day, and then finally overnight. That one had been the hardest, no pun intended. I would wake up multiple times a night, locked in sweet torture between the inevitably erotic thoughts in my head and the bittersweet tightness between my legs. The first time I'd tried it, I'd made it till 2 a.m. bef...