114 Votes
Chis(topher) & Chris(tina) (ch. 2)
Chapter 2. - Chris and I meet the grandparents
Topics: Crossdressing, Transgender, Sissy, Sex, Boyfriends
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.
Chapter 2. - Chris and I meet the grandparents
Topics: Crossdressing, Transgender, Sissy, Sex, Boyfriends
I would go to the park at night letting guys blow me until the fat old man turned me into the cocksucking cumloving slut at the park and at my mom's house.
Topics: Crossdressing, Big Dick, Daddy, Slut, Park
I met and fell for a crossdresser, explore chapter 1 introducing us, and future chapters meeting family and friends
Topics: Anal Sex, Crossdressing, Transgender, Cum Swapping, Sissy, Oral & Blowjobs, Nipple Play, Boyfriends
A shy, submissive guy hits me up to dress like his wife and Domme him. I actually liked it more than I thought I would!
Topics: Crossdressing, Bondage, Domination, Submission
It took while, but my transformation is complete
Topics: Anal Sex, Crossdressing, Straight Men, Sissy, Bareback
I forgot and wore some panties to my check-up. The doc was surprised. But he responded differently than I expected.
Topics: Crossdressing, Doctor, Medical, Lingerie, Panties
Joe was always pretty much a Dom. But he seemed to figure out I'd do pretty much anything to suck him off. So he just keeps pushing. Now I have to go out and buy some items he requested. And that is a whole other story!
Topics: Crossdressing, Rough Sex, Spanking, Oral & Blowjobs, Lingerie, Panties, Fucking
I had spent all of my time getting indoctrinated in gay sex by Tom G. I forgot about my first man to pop my anal cherry Mark.
Topics: Anal Sex, Crossdressing, Sissy
I went to work and tried not to run into Jerry, but that was hard, seemed like Jerry kept looking over at me and would walk by me giving me a look. When no one was around, he would come up to me and show me a picture of me on his phone of me in one of the positions that I was in.
Topics: Crossdressing, Coercion, Blackmail, Domination
The best looking girl in the bar was a guy and I love her.
Topics: Crossdressing, Transgender, Boypussy, Oral & Blowjobs, Shaved, Sixty Nine
My wife installed one of those nanny cams. She wanted to see what the dog was doing when we were at work. She didn't tell me. She started watching me dress in her underclothes and tie myself up like a kidnap victim, jerking off. Not sure what to do, she asked a friend to watch the videos. He knew just what to do with me.
Topics: Crossdressing, Bondage, Married
Dressed up for jr high halloween party. Was dressed as a sexxy sissy. I was that skinny nerd that nobody knew. Had a a nice bubble butt. Mark the handsome popular guy had his girlfriend breakup with him. Not knowing who I was. I turned him on. We made love even after he found out I was a guy
Topics: Anal Sex, Crossdressing, Boypussy, Twink, Hookups & Dates, Halloween
Envious of the girls always getting to wear those cute little bras and panties.
Topics: Crossdressing, Sissy, Lingerie
I decided to dress up as a girl for halloween. There was a big party going on for us jr high kids. And looked good. Maybe to good. Mark was a good looking guy. Something happened at party. He became attracted to me.
Topics: Anal Sex, Crossdressing, Sissy, Halloween
While well over the legal age of sexual consent, my looks represented a much different picture. Broght up by a single parent overbearing mother, my being raised was far from the normal channels of a lone single male son.With mom making dresses and me the perfect slender size to model her creations, I guess you could say that the soft silk and lace never failed to stimulate me in a secret sexy way
Topics: Crossdressing, Voyeurism, Sissy, Oral & Blowjobs
Dressed up for Halloween and nowhere to go. Until I get invited to a last-minute party.
Topics: Black Men, Crossdressing, Oral & Blowjobs, Halloween
The clerk at Macy's gave me a strange look as he checked out the lingerie I was buying.
Topics: Crossdressing, Public Sex, Oral & Blowjobs, Lingerie
I meet a cute sissy out for prom night. But he needs a date.
Topics: Crossdressing, First Time, Sissy
I met one mature men on grindr and and then we enjoyed a lot in hotel room. He fucked my 2 times in row continuously. Then he became my fantasy partner.
Topics: Anal Sex, Crossdressing, Daddy, Hotels, Oral & Blowjobs, Hookups & Dates, Facial, Grindr
Silly me gets seduced by a pretty closet crossdresser. I help her come out, so to speak. And I have a nice time as well.
Topics: Crossdressing, Seduction, Lingerie
A pervert friend takes me from my first hand-job, up through the progression to where I was escorting him out to bars as a woman.
Topics: Crossdressing, Oral & Blowjobs
I thought wearing my sister's underwear made me gay. I was worried about that. But it didn't. But finding someone who wasn't repulsed seeing me in her stuff was very difficult. Until now.
Topics: Crossdressing, Coming Out
When I came back from California, changed into a Caitlyn, I was surprised how many of my old schoolmates and teachers were trying to get in touch.
Topics: Crossdressing, Transgender
I only found out much later that she set me up to catch me in her undies and tricked me into becoming a sissy peg boy and later a slut for her x boyfriend who she was still fucking. I guess that is the whole story, actually!
Topics: Crossdressing, Bondage, Rimming, Straight Sex, Chub, Oral & Blowjobs, Married, Pegging, Tricked
Wife catches me the first time. Very embarassing. But not at all as bad as when she turns me over to the kinky gay guy she works with.
Topics: Crossdressing, Humiliation, Sissy, Oral & Blowjobs, Tricked
Joe found my personal chats and used them to blackmail and abuse me. I loved it!
Topics: Crossdressing, Blackmail, Diapers
Going to a hotel dating game is different when all the people are matched up to their kinky fetishes and fantasies.
Topics: Crossdressing, Bondage, Hotels, Oral & Blowjobs, Domination, Submission, Throat Fucking
My first wife was a bitch. She put me through hell. But the second one put me through something worse. Watching her boyfriend fuck her while I was bound and gagged and tied to a chiar in the bedroom. Maybe my third wife will be nice to me.
Topics: Crossdressing, Bondage, Dildo, Cuckold, Pegging, Gagged
I met her at the hotel bar. There was a crossdressing convention there that weekend. I didn't know it. But I found out soon enough.
Topics: Crossdressing, Transgender, Seduction, Oral & Blowjobs
im not very fem but i love to wear panties. A golfing partner saw my profile on a webite like this and made the most of my situation.
Topics: Crossdressing, Coercion, Blackmail