Transsexuals+&+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...

A Showman Ch. 1

by SavageGenius on Sep 12, 2017
Exhibitionist & Voyeur

The window opened on the desktop and Stan adjusted the webcam. The profile screen appeared. Stan considered the things he wanted to reveal to his Wild Web World audience. Name? Mr. Average. Location? At home in Raleigh. Age? 28. Height? 6’2”. Weight? Above Average. He decided that if you were going to be seen on a webcam, you couldn’t really hide the truth,...

The Hitchhiker

by hydrangealawrence on Oct 8, 2019
Transgender & Crossdressers

I shade my eyes and scan the road. It's been at least half an hour since the last car. The heat radiates off the asphalt. I lick my parched lips. I'm almost out of water. I spot a vehicle approaching through the shimmer. I jut my hip, stick out my thumb, and hope. A rusted Ford pickup rolls to a stop in front of me. A man in tinted aviators and a sleeveles...

Anal Tonight

by AlinaX on Mar 2, 2020
Transgender & Crossdressers

Mark looked at me quizzically as he closed the front door and shrugged out of his coat, draping it over the banister. "There's something different about you," he said. "Have you been to the salon? And is that... Are you wearing a push-up bra?" "Do you like what you see?" I asked, trying to sound seductive and not terrified. He nodded, his lips curling into...

A Beautiful Nightgown Made of Silk

by lynntg0444 on Mar 18, 2020
Transgender & Crossdressers

For as long as I can remember, I always wanted to wear girls clothes and would indulge that desire whenever possible. I would always sneak to try on my girlfriend's lingerie, which was usually very boring cotton stuff. One weekend during spring break from college, I was staying at my uncle's vacation home on a lake, and met some neighbors. They invited me to...

Anal Training Ch. 02

by Catchandrea2397 on Jan 20, 2020
Transgender & Crossdressers

Are you ready to be a good obedient sissy pet? Well shall we begin day 2 of training. Have you got everything I asked for last time? Good. Today you'll need: - Bra and panties - Lube - Butt Plug - Vibrator Get these things and lay them out on the bed. Go shower. I want you nice and clean. Clean now? Good. Now I want you to crawl naked to the...

My Sexy Changes Ch. 05

by TaraJaden on Apr 21, 2020
Transgender & Crossdressers

I wore a white dress that came down to mid thigh and had frilly shoulders that barely held onto me, the neckline exposed my chest showing the little bit of cleavage I could form. I matched my dress with white low heeled shoes and once again curled my hair so it would just touch my cheeks. When I arrived at Alex's house he answered the door and invited me in...