Crossdressers Stories

12,121 results
Orientation
Length
Source
Infinite Scroll

My Journey to Heaven

by Corina84 on Sep 14, 2017
Transsexuals & Crossdressers

How did I end up here? I couldn't believe what just happened! I was in a daze from what I just did. I was neither sickened or disgusted by it, I was just surprised that I had come so far. Here I was, on my knees with cum drizzling down my face. Something that I have fantasized about for years, but was never able to gather enough bravery to step out and try...

A Night Drive Pt. 02

by 13feathers on Jan 22, 2019
Transgender & Crossdressers

The rest of the drive to the station was tedious and not at all erotic. Once my arresting officer had parked, and cut the rope connecting my bound wrists and feet and untied my ankles, he escorted me out and up the stairs. They were painful to climb with how limited my movement was, but I managed. Entering the building I found the main hall was mostly a coll...

A Night Drive

by 13feathers on Oct 3, 2018
Transsexuals & Crossdressers

My heart was pounding; my parents had finally, finally, left. On date night, they might be out of the house for four hours, maybe more. It was more than enough time for what I had planned. They were standing by the curb, smiling as I waved to them from the veranda. As they took off and drove, my body quivered with the thought of what I'd do next. The secon...

I Adore Crossdressers Pt. 04

by Ab9095 on Dec 3, 2018
Transgender & Crossdressers

Day 3 When she left last night she was a very happy girl. I have her clean up. Redo her makeup. Get her pretty. And then she has to leave like that. She makes me promise she will see me tomorrow. I actually have a hard time sleeping that night. She's running through my mind and I'm thinking about tomorrow. I send her a text in the morning telling her to...

Transsexual Sisters Ch. 07

by SplitLicker69 on Sep 14, 2017
Transsexuals & Crossdressers

Part 7: A career decision NOTE: The 7th and final story of Michelle and Nicole. Michelle started a conversation. "What does one do if she wants to become and escort?" "Are both of you considering this?" Misty asked. "So far we have just tossed the idea around. We are young, healthy, adventuress and, if you can believe it, cannot get enough sex. Did David...

Pink Panties

by DrLuverotica on Mar 27, 2019
Transgender & Crossdressers

It all started with a pair of pink panties. It was sometime after midnight when Jo arrived home from being on-call at the local hospital. She'd received a phone call several hours earlier about a bleeder and had to rush in. Recently her workload had become almost unbearable, but we needed the money so she was working her sexy curvaceous ass off. By the ti...

Undercover Angel Ch. 01

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

When Mike Harris stole two point seven million dollars in cash from his employer, he knew that his life had changed forever. It's one thing to steal that amount of money from your bosses' safe; it's quiet another to steal it from a ruthless gangster who is heavily involved in narcotics, prostitution, gambling and murder. Mike was Tony Leonardo's bookkeeper,...

Crossdressing, Piss and Sex

by Lovinhose on Apr 14, 2020
Transgender & Crossdressers

This is a work of fiction, a fantasy that I would love to come true. It also contains 'pissing' (aka 'watersports'), crossdressing, and a crossdressers sex with men, so if you are not into these subjects, this story might not be for you, you have been warned. Also, comments are welcome, but please note, I'm NOT a professional writer, if I was, I wouldn't be...

Chablis' Panties Ch. 01

by earnestwinter on Sep 16, 2017
Transsexuals & Crossdressers

Alexandra popped my cock out of her mouth, and slid my panties back over it, holding them down firmly, while she supported herself on my hips, thinking out loud. "Who would you most like to have a threesome with? You know, if it's somewhat achievable?" My heart was racing, and I was rock hard. I sat up on the bed, and turned the computer screen away from th...

Magic Dress - Serena

by SlightlyRude on Dec 3, 2019
Transgender & Crossdressers

Note: The early part of this story can be found in Cream and Lace. ***** CHAPTER 1 It was the biggest surprise I had ever had on a birthday, and it turned out to be the best birthday present of my life. My darling wife Samantha bought a dress for me. To some extent it should not have been such a surprise. My brother Frank was staying with us, and he like...