Chastity Feminized Stories

7,367 results
Orientation
Length
Source
Infinite Scroll

My Friend Ashley Ch. 05

by jealouscuck on Jul 29, 2019
Transgender & Crossdressers

Things were no longer in the experimental stage. Gretchen had set me on a path to feminization and Ashley was following her lead. Ashley had already broken one of her restrictions. She had allowed Gretchen to perform oral sex on her. The distinction that I was performing oral sex on the women while dressed as a female. When Gretchen ate Ashley's pussy, Ashle...

Wife and Bull Conversation

by CuckoldGuy on Apr 10, 2019
Fetish

"Met your husband Saturday. He was getting gas when I pulled up to the pump next to him. I didn't realize it was him until I got out of my car, so I had to say hello." "Oh, what did you guys talk about?" "Just the price of gasoline but let me ask you something? Does he know about us?" "Why do you ask?" "Well, I never liked him. When we were in high schoo...

Crossdresser Evolution Ch. 03

by pantyhigh on Jun 12, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing I was becoming addicted to masturbating while wearing panties, though there was still a feeling of shame surrounding it. I saw myself in these cum soaked pink panties. I could feel some sense of arousal but at the same time was ashamed that I was standing there wearing my wife's pantie...

The Perfect Pair Pt. 07

by ChangeYourPassword on Sep 14, 2020
Fetish

The Perfect Pair, Part 7 (fetish, chastity, consensual, cross dressing) By ChangeYourPassword Author's Note: This is a work of fiction. It is a story of sexual fantasies and fetishes. These sexual practices are not for everyone, but those of us who delve into them understand the allure. The characters in the story certainly do. If you enjoy this story and...

Sissy Escape

by Haley_Hazel on Sep 26, 2017
Fetish

You are John Doe An average man, not too young, not too old. You have zero money, no car, no girlfriend... Basically a real loser. You live in a dive apartment downtown. It's not a great place to live, but it's home. Everything you need is right nearby. Groceries, Bar, Restaurants, it's near a park, and there's even a porno shop down the road. Because it's d...

Open in Reader

The Perfect Pair Pt. 08

by ChangeYourPassword on Oct 6, 2020
Fetish

The Perfect Pair, Part 8 (fetish, chastity, consensual, cross dressing) By ChangeYourPassword Author's Note: This is a work of fiction. It is a story of sexual fantasies and fetishes. These sexual practices are not for everyone, but those of us who delve into them understand the allure. The characters in the story certainly do. If you enjoy this story and...

An Afternoon Tea

by suzette_la_soubrette on Sep 13, 2017
Transsexuals & Crossdressers

Scene One: Backstage "Ah, there you are my pretty pet! All nice and comfy on your pretty perch, are we?" I hear Miss Debra's cheerful voice from behind me. I scan the large, ornate, gold-framed mirror hanging on the wall before me, straining my corseted neck to determine her whereabouts. I quickly spot the reflection of her pretty face, as she playfully...

House Rules Pt. 02

by GavinNuisance on Mar 16, 2020
Transgender & Crossdressers

Terry laid naked on Lana's couch, face down with his ass sticking up. Her cum had dried. Drowsy, and still a bit tired, Terry began to move, and stretched as he adjusted his eyes to light. He noticed the sun was setting and he was clearly there for at least a few hours. He rubbed his eyes, but noticed a peculiar feeling in his backside. "What the fuck?" He...

My Saturday Night

by honey28 on Sep 26, 2017
Transsexuals & Crossdressers

Dear Readers: Another true story, the weekend following "My Friday Night." Hope you like it... *** After my shower, I dig through my bag for my stockings, glad to see that the garter straps are attached and none have gone missing. I toss them on the bed with my bustier, pick out a pair of black lace panties, and get dressed. Two years ago, I never would...

Sindys Undoing

by SindySuxALot on Sep 26, 2017
Transsexuals & Crossdressers

Lucy had been following Dr. Cornelius for months now. He had been one of the 20 endocrinologists in Orlando on her list when she started this quest, and he seemed to her to be the most likely candidate to help her with her goal. She had ruled out almost all of the others after delving into their backgrounds. From what she could tell in her research, Dr. Corn...