Ladyboy Fuck Guy Stories

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Business to Improve Sex Lives Ch. 05

by walterio on Oct 23, 2018
Novels and Novellas

MORE EROTIC TRAINING ON THE AGENDA Trace and Brittany woke up in a spoon position with his morning erection pressed into her curvy bottom. His hands encircled her upper body and fondled her lovely breasts. If they didn't have a client that day they would have made passionate love as they always enjoyed each other so much. "I really love your body and cares...

Thai Travels Ch. 06

by S_Queen on Jan 4, 2018
Transsexuals & Crossdressers

Welcome back, readers, for the final chapter of my story. If you've been with me since the beginning, you will have accompanied me on a taboo shattering journey, both geographical and sexual. I discovered a flair for public sex, I engaged in group sex and threesomes with lesbians, I fucked gays up the arse and received expert blowjobs from them, I played wit...

Jamie's Descent Pt. 01

by nikkiesilk on Sep 18, 2017
Transsexuals & Crossdressers

Chapter 1 What did we do before social media? How did we manage to get through the day without that endless stream of dirty jokes, funny photographs, gossip and links to dodgy websites that now fill our lives? Yeah, yeah, I can hear you grumble. Get on with it, I can hear you say. Well, dear reader, it was one of those links that started me down the road to...

The Reunion Ch. 02: Thai Massage

by Valtikka on Jul 15, 2020
Anal

"Krissy! Long time no see! It's so good to see you. You look great girl!" As soon as I get out of the Uber, Micky comes walking to me with wide open arms and gives me a big hug. "Come let me help you with your bags. You're the first one to arrive so you have first pick on the rooms. The rest of the gang will arrive tomorrow." Instead of the overalls I'm use...

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...

Dark Angel Ch. 01: The Meeting

by ReiverToo on Sep 12, 2017
Transsexuals & Crossdressers

It was after 10:30 pm when my Japanese business associates had finally had enough sake and karaoke to call it a night. Maybe they were just off to see if they could score some company for the rest of the evening. Who knew? They were all on huge expense accounts, so buying a girl (or boy) for the night was not a financial problem. Some had even offered to inc...

Transsexual Journey 03

by walterio on Sep 19, 2017
Transsexuals & Crossdressers

ONLY TWO DAYS LEFT BEFORE ARRIVING IN BARCELONA Jay had never in his life that he would have hooked up with a ladyboy. He also never expected that he would enjoy the brief affair as much as he did. He had to admit that Caridad was as beautiful and shapely as any woman he had dated. The fact that only he knew that she was a ladyboy was also a turn-on for him...

Agnes Dourville Ch. 12

by ValoryG on Sep 16, 2017
Transsexuals & Crossdressers

When the massive shovel at the bottom of the open-pit mine drops its load into my oversized dump truck, I shudder along with the entire vehicle. In fact, the earth itself shudders. I'm being loaded with taconite by one of the largest hydraulic earth-shovels in the world. Wearing panties while doing so gives me such a perverse pleasure.... I gun the diesel e...

Addicted to Pream's Cream

by Vodka_Jim on Sep 26, 2017
Transsexuals & Crossdressers

It didn't take long after my divorce to settle into a routine. I had my kids the first, third, and fifth weekend of every month. That left me with a lot of free time on the second and fourth weekend. I wasn't inclined to date much at that point and had no real interest in hooking up through Tinder or other dating apps. So my routine on those Fridays was to g...

Encounter of the First Kind

by gendidi on Sep 16, 2017
Transsexuals & Crossdressers

I'm a married man in my mid forties. I have an older disabled wife. We don't have any children. We have been married for a decade. Ever since she was disabled, we stopped having sex. She gets depressed occasionally and has been taking happy pills for years. Maybe that's why she lost her sex drive and I don't blame her. We never discussed about sex. I assum...