Transgender & Crossdressers Stories

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Face Down Ass Up

by Junglist187 on Jun 1, 2020
Transgender & Crossdressers

A few years ago whilst living in Manila in the Philippines I met and formed a very strong friendship with Leslie. Leslie was a very petite ladyboy I had met online on one of the dating apps, we had chatted for a few days and then we planned on meeting each other face to face. I had already told her that I'd only ever met one ladyboy before and had really...

Second Date

by Liethra on Jan 22, 2020
Transgender & Crossdressers

That day at work was the longest of my life. An eternal trial where my soul was tormented by an unending stream of teasing photos and messages from my new playmate. The best kind of suffering. While I was trying to work, she kept sending me every kind of lewd thing she could imagine. And let me tell you, it's not easy explaining logistical efficiency to a n...

Sandy's First Time Ch. 01

by MadisonWillow on Feb 4, 2020
Transgender & Crossdressers

"Fuck, I look sexy," Sandy thought to herself as she stared at her reflection in the mirror of her hotel suite's bathroom. She had just finished getting dressed, and the butterflies were circling around in her flat, firm stomach. This would be the first time "Sandy" would reveal herself to another gurl. Well, aside from when she would cam with other like-min...

Birth of a Slut Pt. 05

by Njcdslutgina on Oct 6, 2020
Transgender & Crossdressers

I went to bed that night confused. I had gotten fucked but also licked my aunt's cunt clean. The next morning when I got up Denny had already gone to work. Eileen was sitting having coffee in her robe. She looked at me and smiled, "Have a good time last night? Now start explaining to me what is going on." I told her the story of me catching her sucking Denny...

Blackmailed into Submission

by tzleaze123 on Feb 25, 2019
Transgender & Crossdressers

I was content with my life and my playtime of closet cross dressing. I worked a regular 8 hour a day job and upon arriving home I would shower and dress up in one of my sexy dresses and have a good playtime session with myself. No one knew any better. Here I was all dressed including make-up and wig also with some rather nice fake breast molds glued to my c...

College Boy Buys a Thong

by Applebottom1 on Jan 23, 2019
Transgender & Crossdressers

So, this is a memory of my introduction into cross dressing and sissy life that I wanted to share. I was a college freshman and it was the last 90s. I was in my second semester I was doing great in school. However it was not doing great with getting any girls to go out with me or anything else for that matter. This was also the magical period of time when...

8mm Queen

by dedimm on May 22, 2019
Transgender & Crossdressers

(This was written after viewing Lilith's video. She is a very, very sexy shemale. The way the video is shot it looks like an 8mm film you would see in the old-time smut booths of a dirty bookstore. Porn in the 40's 50's 60's 70's was not easily accessed like today with the internet. The fact you risked being seen entering an adult bookstore coupled with the...

Making of Alice

by sissyassslut on Dec 12, 2018
Transgender & Crossdressers

Once Mistress Vixan had decided that after months of training and trips that she had broken Alice it was time to remake him into the image She had of him. She took him out to a tattoo artist in town and explained to him what She wanted. The artist shaved the upper front of Alice's thigh and from a picture Mistress presented proceeded to tattoo a large BDSM s...

Working Out Issues Ch. 01

by blake1 on Feb 26, 2019
Transgender & Crossdressers

IMPORTANT ETHICAL NOTE: I am 100% pro-body positivity and fat acceptance! I encourage everyone to work out and eat healthy, because being fit feels GREAT. But you should never be ashamed of the way you look. IMPORTANT JERKING OFF NOTE: This whole first chapter is just set up. Sorry hoes! ***** "Adam!" I moaned. Adam poked his head out from the kitchen,...

A Long-Distance Relationship Ch. 05

by allourdesires on Sep 24, 2019
Transgender & Crossdressers

While I waited, talking quietly with Karen in the living room we were left in no doubt, whatsoever, as to what was going on in the bedroom across the hall. Karen never said anything but it was clear that there were at least two men in Anne's room; different voices cajoling and using the foulest of language to demean and humiliate my girlfriend as they took t...