Tranny Stories

1,390 results
Orientation
Length
Source
Infinite Scroll

Being Holly

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

Okay like right off I want to make it clear it's Holly now and forever. Holt's fucking dead and I'm killing anything that's left. And that's a damned good thing. See Holt was an asshole, I...he...that person I was...I was raised by an asshole. My dad and he wasn't a nice guy. He was a jock, he was a mean jock raised by worse my grand dad. Holt was part...

Training of Melissa Ch. 01

by SEVERUSMAX on Sep 17, 2017
BDSM

Melissa punched in as usual for her day job, yawning in spite of the energy drinks that she guzzled to stay alert. Her other profession was an open secret, but as long as it didn't interfere with her performance at this one, none of her supervisors would take any notice of it. She was popular with many of her colleagues, after all. There were exceptions, of...

The Nightshift Girl

by BmthAdmirer on Sep 16, 2017
Transsexuals & Crossdressers

As work had been short of late I had been into town and signed up with a hand full of recruitment agencies offering temporary contracts to basically anyone who wanted work and wasn't bothered about what it was or where it was. Unfortunately after wandering round town for hours I finally got fed up of dealing with the consultants and answering the same questi...

Hard Day at the Office

by red_fruit on Sep 15, 2017
Transsexuals & Crossdressers

I suppose that working in a female dominated job like this should have been a clear enough sign, but I had managed to keep it all a secret for this long. Sure there were little tells, but I if I kept my head down and maintain a pretty low profile at work it was all OK. And so here I was, four years working as an administrator (glorified pool secretary!) with...

Two Way Display Ch. 02

by seams_straight2me on Jul 15, 2020
Transgender & Crossdressers

Tia: After Zoe had cum over my tits, we cleaned ourselves up. We had a shower, but not together, as we both wanted to just be Tia and Zoe in front of each other for now. With my stockings and lingerie a bit of a sticky mess, Zoe offered to wash those for me, and I could pick an outfit from her wardrobe. Zoe did admit she also offered to wash my stuff to h...

Tom, Aaron & T-Girl Alexa have Fun

by THoward95th on Dec 23, 2019
Transgender & Crossdressers

This is part of an ongoing story over multiple Categories with common characters. ************ Alexa rolled into town and texted me as soon as she did. Ding! Alexa -- Hi Tom! I'm here. Me -- Great, glad to see you made it safe. What you need from me sweetie?" Her -- I'm going to check out Piranha's first then would love a shower. Me -- Cool. I have t...

Jennifer's New Adventure Ch. 03

by JenniferTaylorTV on Feb 10, 2020
Transgender & Crossdressers

Jayne started easing her dress up over her thighs. They were tanned and muscular but in a very feminine way. With her dress resting on her hips, she reached out and grabbed Jennifer's lead from the fat woman. "Come here Jennifer. I want to see if you like the taste of pussy." And she forced Jennifer's head between her legs. Jennifer could see Jayne was turne...

Jennifer's New Adventure Ch. 02

by JenniferTaylorTV on Feb 10, 2020
Transgender & Crossdressers

Jennifer stood in front of the mirror and admired the glorious image before her. There she was, a gorgeous bunny girl in a tight, high cut black costume which gave her a wonderful curvy figure. Her fake boobs looked real and gave her an awesome cleavage. Her superb bubble butt had a kinky little fluffy tail and three-inch heels made her legs, encased in blac...

Sub Rosa Ch. 02

by Margotcul on Oct 6, 2020
Transgender & Crossdressers

3. Needless to say my night was -- again -- troubled. I removed and cleaned the vibrator before I went to bed, but the cage remained in its place. I woke up numerous times during the night to painful erection attempts. After my second night with little sleep, I was in ruins. I got out of the bed and left my bedroom. There was no sign of Mael yet. I did my...

A Pair of Objects Walk into a Bar

by YKN4949 on Sep 16, 2017
Transsexuals & Crossdressers

"She wouldn't even have to bend over or get on her knees!" One of the bros giggled to his friend. The other guy was nodding wildly. "Usually they have those like...weird shaped foreheads and huge shoulders and shit. But she's..." the other guy responded, not exactly on point with the initial comment. "She's fucking hot," the first guy finished for him. I...