Transgender & Crossdressers Stories

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My Naughty Bunny Night

by Bobbigirl19 on Nov 18, 2019
Transgender & Crossdressers

When I started college I explored. I started transitioning as a teenager and I had quasi-regular sex by the time I graduated, but I was still pretty reserved in high school. My experience was three months-long high school boyfriends, two high school friends and a college writer type, and one party hookup with a friend's uncle. College brought me to a small...

A Day Alone with My Inner Sissy

by Abitinsecure on Jan 21, 2020
Transgender & Crossdressers

It started off like any other of the rare days I have the house to myself. I woke up early at sunrise and slipped out of bed and headed for the shower to cleanse myself for the fun I was preparing myself for, something I always make sure to do as my mind starts flooding with my sissy fantasies and curiosity. I would consider myself a straight guy, work a la...

Hotel Gangbang Ch. 01

by Gabbytv on Jul 6, 2020
Transgender & Crossdressers

I am a whore. No cancel that. I am a slut. I love to wear the most depraved sexually appealing outfits. The more quickly I can bring a man to an aroused state the faster I can be on my knees savoring something greater than any drug I've had, cock. Whether I'm dressed as a Catholic schoolgirl and sucking shaft or dressed like a hooker in spandex and tights a...

Quarantined by Nature

by Aestheticprosthetic on Oct 6, 2020
Transgender & Crossdressers

Content warnings: homophobia, cisgender anatomical terms, dubcon/noncon, breeding. Quarantined by Nature We were assigned together to quarantine lockdown, two guys, reluctant male roommates for the duration. Such a small space to share, a tiny studio apartment with open bunks. Locked in. Duration of quarantine? Uncertain. Neither of us feels ill; this is p...

Birth of a Slut Pt. 01

by Njcdslutgina on Oct 6, 2020
Transgender & Crossdressers

Recently I decided to share my story of how I became a cross dressing slut. While always turned on by stockings and heels my first real chance came after I turned 18 and went to my first adult costume party. A little more about myself. At 18 I was 5'11", 175. I had long hair which was the style of the day cut in a shag. My cock is small, 5 inches but I have...

Birth of a Slut Pt. 04

by Njcdslutgina on Oct 6, 2020
Transgender & Crossdressers

Since no one was home I decided to be brave. Still dressed I practiced walking in my new heels and shaking my butt. I was drinking a beer and decided to try out the butt plug but first an enema. This time just soap and water. I took 3 and the last came out clean. I put some of the anal eeze in my ass then the plug. I placed it on a chair and sat on it. I wan...

The Club of Fools Ch. 09

by sublocked on Sep 19, 2017
Transsexuals & Crossdressers

Author's Notes: (1) This is fiction, just a story; (2) One should never start a book at chapter 9. This story as a whole is way longer than I anticipated when I started, too long for those who hate it, not long enough for those who like it...apologies to the latter group; (3) Jason is not being exploited by anyone except himself, and shouldn't we all expl...

Transgender Avis's Incredible Power

by justincbenedict on Jul 4, 2018
Transsexuals & Crossdressers

Skokie, Illinois, 2009 Aiken Aycock was sad to be losing her brother Aiden to the operation. He was a great guy, but he gave Aiken the beatings and torture she needed. But he'd finally gotten the money to do the big change. Aiken had really enjoyed supporting Aiden, letting him live in her apartment...stripping naked when she got home, and taking a few fro...

The Perils of Young Guys

by Etaindarcy on Aug 7, 2019
Transgender & Crossdressers

Young guys are pretty; but not always so fun. I've only been with one guy younger than me, so maybe I don't know what I'm taking about - but here it is. If you've read my previous stories then you know about my first time with Jack and Kyle and about my special friend Missy and her teenage brother Caleb. If not, let me catch you up. I met Jack and Kyle in...

Minimum Security Prison Bitch

by JonThomas_ on Dec 19, 2018
Transgender & Crossdressers

Greetings all; in my stories my characters exist in my head, but there might be real life inspirations for some of them. Who knows? As my regular readers are aware, I enjoy writing about the transgender experience from different perspectives. Here I write about a transgender woman whose experiences in prison were quite different than she expected them to...