262 Votes
A Very Naughty Night
Cari goes out dressed as a sexy woman to a night club and becomes a woman in the arms of a very masculine man!
Topics: Anal Sex, Crossdressing, Rimming, Big Dick, Transgender, Oral & Blowjobs
GayDemon's Stories: On this page you can find erotic fiction where you can read about men dressing up as women and gay sex with transvestites and crossdressers listed by date.
Cari goes out dressed as a sexy woman to a night club and becomes a woman in the arms of a very masculine man!
Topics: Anal Sex, Crossdressing, Rimming, Big Dick, Transgender, Oral & Blowjobs
A cross dresses journey
Topics: Black Men, Anal Sex, Crossdressing
A cross dressers Journey
Topics: Black Men, Anal Sex, Crossdressing, DP, Big Dick, Fisting, Group Sex, Oral & Blowjobs
My association with the most fantastic guy I've ever met, who is now my employee. Also I see my first live sex show in a theater.
Topics: Latin Men, Crossdressing, Brazilian, Twink
"YOU BITCH!!!!" she screamed. "YOU DAMNED, FILTHY BITCH!!!' Tears were streaming down her face as she softly cried, "I trusted you! How could you?"
Topics: Anal Sex, Crossdressing, Big Dick, Transgender, Oral & Blowjobs
Hired to Play Romeo to cross-dressed Juliet
Topics: Anal Sex, Crossdressing, Transgender
A cute young cross dresser submits to the wants of a "Daddy".
Topics: Crossdressing, Spanking, Transgender, Daddy, Breeding, Role Play, Oral & Blowjobs
For years I'd frequented adult bookstores. I would look around the shop a little pretending to be interested in buying something from the store. After what I felt was a sufficient amount of time browsing I would get tokens from the clerk, always hesitating to look directly at him so as not acknowledge what I was about to do.
Topics: Crossdressing, Big Dick, Bisexual, Gloryhole, Bookstore, Oral & Blowjobs
Stuck in GM land between nowhere and nowhere else
Topics: Anal Sex, Crossdressing, Hairy men, Transgender
Life for a young skinny gay teen can be tough, for Allen, he wants to spice things up by inviting a man to his own house while his parents are on a trip, he may find more what he was looking for.
Topics: Anal Sex, Crossdressing, Twink
Power top NYPD vice cop Mike Kavanagh hunts blonds and a serial killer of blonds in New Orleans
Topics: Anal Sex, Crossdressing, Cop, Bareback, Mystery & Crime, Oral & Blowjobs, Blond
Everyone gains and loses from a poker party.
Topics: Black Men, Anal Sex, Crossdressing, Big Dick, Spanking, Fisting, Bareback, Oral & Blowjobs
"You know.....there's a lots of men here who'd probably love to have you suck them. And, maybe, they'd like to fuck your pretty bottom."
Topics: Anal Sex, Crossdressing, Transgender, Bookstore, Oral & Blowjobs
"I wonder what your parents would think? I wonder if they know their little boy was a cross-dressing, cock sucking slut?"
Topics: Anal Sex, Crossdressing, Rimming, Transgender, Slut, Oral & Blowjobs
Besides discovering the joys of sucking dicks I've reconnected with Linda and old girlfriend and briefly moved in with her in her mobile home in Kennedale. This had a double pay off. Besides living with Linda, it put me less than fifteen minutes from the adult bookstores with the viewing booths.
Topics: Crossdressing, Humiliation, Feet, Gloryhole, Cum, Bookstore, Oral & Blowjobs, Master & Slave
I pay my admission get my locker put my clothes in it, shower dry off and lube my ass up just in case, but also love having a finger stuck in me.
Topics: Anal Sex, Crossdressing, Poppers, Dildo, Leather, Bisexual, Gloryhole
This story is how my alter ego, Ana Le Babe, came into being. This and following stories relate the encounters she has had (both sexual and general), and are all true. In writing this, I hope to help others in a similar situation deal with their feelings and stimulate those that are interested in our way of life.
Topics: Crossdressing, England, Oral & Blowjobs
Fun with a wife and her cross-dressing husband
Topics: Crossdressing, Rimming, Transgender
fun at the truck stop
Topics: Black Men, Anal Sex, Crossdressing, Big Dick, Sloppy Hole, Trucker, Ass Play
Fun at the truckstop
Topics: Black Men, Anal Sex, Crossdressing, Big Dick, Small Cock, Trucker
Alright, so I decided it was unfair to end this series on a cliffhanger. If you read this and want more, say something.
Topics: Anal Sex, Crossdressing, Bareback
A true story of my first BBC and being his crossdressing slut
Topics: Black Men, Anal Sex, Crossdressing, Dildo, Big Dick, Spanking, Sloppy Hole, Slut, BBC, True Story, Throat Fucking
My first crossdressing story
Topics: Anal Sex, Crossdressing, Oral & Blowjobs
American college student traveling South Seas on winter holiday hooks up with Australian street musician in Sydney
Topics: Anal Sex, Crossdressing, Hairy men, College, Travel, Oral & Blowjobs
Small town Ohio café waiter Casey dreams of escaping and finding sexual adventure.
Topics: Muscle, Crossdressing, SM
Why would a tennis pro base in Bangkok?
Topics: Asian Men, Crossdressing, Transgender, Sportsmen
Justin is slowly transformed into a sissy by his new daddy
Topics: Crossdressing, Spanking, Daddy, Sissy
A fantasy of becoming a black mans sissy slut but hope it cums true someday
Topics: Black Men, Anal Sex, Crossdressing, Dildo, Big Dick, Slut, Sissy
This straight acting boy/guy has a sissy hidden inside him and is found out about by a friend who transforms him into the true sissy he wants to be.
Topics: Anal Sex, Crossdressing, Sissy, Oral & Blowjobs
glory hole suck
Topics: Crossdressing, Big Dick, Gloryhole