Sissy Crossdresser Stories

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Infinite Scroll

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...

My Brother, My Sister Ch. 01

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

I wrote this story originally under the title "Be Careful In the Park" about an older crossdresser who meets a street gang in a park and gets more than she bargained for. There was no incest in the original version. I like this version better as it includes all my peccadillos: incest, crossdressing, nylon fetish, and forced sex. A warning to those who find t...

From a Husband to a Dutiful Sissy Ch. 18

by Sissy_Chantel on Sep 25, 2017
Transsexuals & Crossdressers

Chapter Eighteen: A Honeymoon To Remember "Good Morning Hun." as I kiss Mikel, the morning after our most wonderful night. "Good Morning Chan." Mikel says as he plays with my hair. I say, "Last night was...well so wonderful, you made me feel like a woman." Mikel says, "You are a woman and last night was the best for me too babe." Mikel rolls out of bed,...

Humiliated at an Outlet Mall

by willow619 on Sep 25, 2017
Transsexuals & Crossdressers

A month before my birthday my wife Mel (short for Melanie) hinted she had a special surprise planned. I dislike having a fuss made about my birthday, and even though it was my 30th I expected nothing more than a dinner at a nice restaurant. Instead, on my birthday my wife and I headed to an outlet mall, a regular activity for us. But this time we drove to a...

Darling Nikki

by Latexsissy69 on Sep 25, 2017
Transsexuals & Crossdressers

Chapter 1 - The Setup "I'm going to catch him!" Samantha thought to herself as she looked at her disheveled panty drawer. She now had proof that her roommate, Nick, had been wearing her clothes, but had to catch him in the act. She did a search online for ideas on how to catch him. She looked at cameras, tape recorders, etc... but she knew it wouldn't hold...

Meating Terry

by andyorlando on Sep 16, 2017
Transsexuals & Crossdressers

It all began about 12 years ago. I'd broken up with my latest girlfriend and I was on the prowl for another lady friend. I'd met some prospects, even been out on a couple of "dates" but nothing was really taking off at that point.. Then came Terry, and Terry was a guy, but to be honest not at all a masculine kind of guy. I would see him around the apartmen...

Being My Wife's Bff Ch. 00: Prologue

by MyUncensoredSelf on Sep 13, 2017
Transsexuals & Crossdressers

When I walked in my wife was sound asleep in the bed. The covers had come off her and she was only wearing a pair of underpants because of the heat. I stared at her for a while, her large breasts hanging down, her shoulder length red hair falling across her face, her big butt. She was so sexy, I wanted her ... but my cock wouldn't stir. It's an issue I have...

Master's Degree in Crossdressing Ch. 02

by wifetoy on Sep 16, 2017
Transsexuals & Crossdressers

This confession is the second chapter of a follow up series to my earlier series "College Crossdressing Confessions." My wife forced me to make those confessions detailing my shameful addiction to wearing panties, pantyhose, and other girly intimates, and my panty pilfering ways in college. While I was making those confessions to the public for the first tim...

Sarah had a Surprise Visitor

by SarahCD on Mar 26, 2019
Transgender & Crossdressers

A few years ago I was working in Hamburg, Germany, and living in a nice, all expenses paid, downtown apartment. Visitors had to be 'buzzed' into the building and so I believed that I could never be surprised by a visitor. I could either ignore them or put on a dressing gown before they got to my door. This was good since I love to dress as a girl whenever I...

Fetish Factory

by shawnavinyltv on Feb 25, 2019
Transgender & Crossdressers

I feel this story needs a quick intro. This was inspired by one of the first pieces of erotic fiction I ever read, The Factory by Tr_Veller. It's a similar story, but it's with a genetic girl and not as much sex, still it was an amazing piece. I tried reaching out for permission to basically borrow the idea and take a trans spin on it, but haven't heard back...