Ladyboy Fuck Guy Stories

265,399 results
Orientation
Length
Source
Infinite Scroll

The Chief Pt. 02

by Aunt_Joanne on Sep 16, 2017
Transsexuals & Crossdressers

I awoke the next morning to the aroma of bacon frying. I was alone in a strange bed, and for a moment, I couldn't remember where I was. Then it all came back to me. It hadn't been some vivid erotic dream. I was lying in another man's bed, naked except for a pair of pink nylon panties. My stockings and garter belt were discarded on the floor, and my male clot...

Craigslist Encounters Ch. 01: Craigslist Cumslut

by xploring96 on Feb 5, 2018
Transsexuals & Crossdressers

The following story includes transgender characters, Domination/submission, and denigrating terms used to humiliate. If this offends you please do not read any further. Feedback on my stories is always appreciated. There maybe additional chapters to this story depending on how this is one is received. If you would like to see a second chapter let me know b...

His Female Client is Really a Man

by walterio on Sep 16, 2017
Transsexuals & Crossdressers

Tim had just finished cutting the lawn and it was time to collect from Michelle Andrews. He always loved collecting from her as she always gave him the most incredible blow jobs. She didn't just suck his cock she made love to it. Sometimes she would make him last for 30 minutes before he unleashed a volcanic like ejaculation and sprayed his seed all over her...

Seduced and Hoodwinked Ch. 04

by walterio on Jan 7, 2018
Transsexuals & Crossdressers

SHOPPING, MASSAGES AND SEX On Tuesday morning Darin and the ladyboys passed on sex and after breakfast they went shopping. They picked up supplies first and then went to a boutique and picked up some new clothes and accessories. They stopped for lunch afterward and at the restaurant many eyes were on the three beauties. Darin was sure that people were wonde...

Recruited Ch. 01

by Rstyusameg on Sep 2, 2017
Transsexuals & Crossdressers

All characters are fictional, except me, everyone in the story is over 21. My stories will involve, male/male sex, cross-dressing, and bad language, so if this offends you please don't bother reading. I stare at myself in the bathroom mirror, carefully applying finishing touches to my pink lipstick, I'm ready. I walk downstairs to fix myself a drink, exu...

An Obsession

by Marcus_Cicero on Jul 30, 2019
Transgender & Crossdressers

It would have been after that documentary. The one with a feature on online dominance-submission relationships on Fetlife. Because before that moment in time life had been so vanilla. Marcus had been queer and had had a boyfriend or two... or three since turning 18. Well, hell, he'd been to the bathhouses since turning 20. He'd even gone as far as to create...

Anal Anywhere, Anytime Ch. 01

by walterio on Jan 22, 2020
Anal

PRELUDE It was the first time that Charlotte had ever come to my place. We had fantastic anal sex on Friday night and we were up for more on Saturday morning. It was a rainy summer day and we were in no rush to get out of bed. She had ridden my cock until she orgasmed and now it was time for me to take that scrumptious ass again. I caressed her ass and tea...

Learning About Kathoeys

by walterio on Dec 2, 2019
Transgender & Crossdressers

PRELUDE Andy Morris was waking up slowly and as he stirred, he felt the presence of another body in bed. He rolled to his side and saw the lovely Jasmine who had stayed the night. She was on her side facing away from him and he took in her naked beauty. He recalled the night before and the marvelous sex they had together. As he looked at her incredible ass,...

My First Ladyboy

by TheSevenSeas on Apr 20, 2020
Transgender & Crossdressers

She was my first. Before I tell you more about her and how I ended up in bed with this gorgeous creature, I should probably make a couple of things clear. First, I am a straight, alpha male. Ex-military, been through a few wars, worked in Africa for a while, have been married and never even looked at another male in a sexual way. Still don't, as there is no...

Promiscuous Parents and Sons

by walterio on Sep 14, 2017
Novels and Novellas

PRELUDE While Pete, Kurt's dad was spending the day with Sandy's mother Lisa, the two twenty somethings were involved with passionate sex. Sandy was sitting on Kurt's body with a thick cock buried in his ass. As Sandy rode his muscular neighbor, Kurt reached up with both hands and fondled the effeminate blonde's cute titties and tweaked the sensitive nipple...