Cross dressing Cumslut
By SoooperFreakk 10 Jun 2022
CD Cumpdump and fun freak meet up
Gay Crossdresser Stories
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.
Summer of My Life
By Roxxi 1 Jun 2022
I Was thinking about Tony' s cock, and as I slid a black lace g string up to my hips and tucked my clit back.
Becoming Ms. Dee Praved
By Ms. Dee Praved 26 May 2022
I venture out to explore my sexuality, and meet a more experienced crossdresser and her friend. He takes us both and uses us well. This is a true story.
CEO
By Victor 24 May 2022
My hot DILF CEO is an alpha with a soft side when we're alone. The older muscle stud wants nothing more than my younger, muscular body to dominate him and make him my bitch.
Crossdresser Confessions
By Ms. Dee Praved 23 May 2022
The true story of one of my favorite guys from Craigslist. He was a horny young soldier just looking to come. Of course I eagerly offer my mouth and ass to him.
Let's Play Dress Up
By James Stone 21 May 2022
"If it's not a big deal, then you do it," I said. He shrugged and got up, going to the box. He dug around until he came up with another bra, a little nicer than the one I was holding, pink lace and pink satin. He held it up and then slipped his arms through the straps, holding it against his chest, over his shirt. He tried to reach around back to close it, but couldn't...
gay switch weekend with the twins
By BillyBoy 30 Apr 2022
this is a gay site, right? well, fuck me running. I got a good one!
New Bookstore Experience
By MontanaBiGuy 21 Apr 2022
A visit to a new bookstore turns into a very fun experience. Oral, anal
The Scoop
By Habu 18 Apr 2022
Garbage man or reporter? Assumptions can be misleading.
Forced cock lovers story
By fanny 2 Apr 2022
A story of a shy crossdresser guy gets forced by a hungry bear.
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Fantasy's come true
By BillyBoy 31 Mar 2022
Finding Mr. Goodbar. Looking for the perfect man to fulfill my fantasies was a long, hard journey.
A Disturbing Desire
By Cirkle7 28 Mar 2022
A gang bang fantasy.
Sissy photo shoot peril
By BillyBoy 25 Mar 2022
The guy was a bad photographer and an even worse perv.
Life's journey (ch. 19)
By JohnAnthony 23 Mar 2022
Sam takes his first visit to a nude beach, meeting a donkey cocked size black bottom guy into cross-dressing BDSM and bondage.
Becoming me
By BillyBoy 22 Mar 2022
Confused and horny I meet another guy in a kinky threesome. And then, I become me.
My summer transformation into a sissy
By Desertbiguy 21 Mar 2022
I turned 18 yo. I was always intrigued by what puberty did to my body. It was summertime parents worked 6 days a week. Leaving me to stay home and do mischievously things.
Carl took good care for me
By BillyBoy 15 Mar 2022
After meeting Carl he agreed to fulfill my crazy fantasies. What fantasies would he fulfill for you?
Straight Pleasures
By Caliban 6 Mar 2022
Theo loves straight, married men... (updated version)
A true story about a shy, submissive man.
By BillyBoy 3 Mar 2022
Late in life I finally explored the dark side. And there is no going back.
Twinkle little Slut (ch. 3)
By westside 2 Mar 2022
I moaned running my hands over my body thinking of all the men I had been with over the weekend and started stroking myself to the verge of orgasm, but I stopped myself because I wanted to share my orgasm with a man any man.
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Be careful what you wish for
By BillyBoy 1 Mar 2022
I let him dress me like a schoolgirl, tied me up and fuck me.
Dressed to Thrill At The Club
By lickme 28 Feb 2022
Getting slutty and hot a gay club for the first time
College Crush Dominates Me (ch. 4)
By RR 27 Feb 2022
Ryan buys me sexy underwear and intoxicates me with his masculine scent before sucking my little nub into the most glorious orgasm I had experienced.
First Date Dressed To Kill
By lickme 24 Feb 2022
Dressed to Kill! First date with stranger and ready for seduction!
Oliver's Story
By Caliban 23 Feb 2022
A transgender love story... (updated version)
Cock Dreams Come True
By lickme 21 Feb 2022
Hetero guy with kinky man to man fantasies
Misadventures of a sissy boy
By Desertbiguy 21 Feb 2022
I turned 18 yo and graduated out of high school. I decided to move out on my own without a roommate. I got great job to pay bills.
Picking up a Stray
By Disbtm 8 Feb 2022
Driving long distances can be lonely. Here's a tale of a driver picking up a little friend on a dark highway and teaching him how to be a good cock sucking sissy. Gas, Grass or Ass, nobody rides for free.
Trying on a few new things
By BillyBoy 4 Feb 2022
Another Halloween is here! Maybe this year I'll catch my first man!
Used like a slut
By Punkboi18 28 Jan 2022
I became a sissy slut in high school and I didn't mind the guys using me for sex. After graduating a bully named Troy decided he wanted my ass. I knew I had to put out.
American cross dresser in Europe
By WLASteve 26 Jan 2022
A 2006 solo trip to European is a fulfillment of a lifelong dream
crossdressing was a hobby
By BillyBoy 22 Jan 2022
I played for a long time in her clothes. I even took some pictures of me dressed up pretty. Now I have men calling me all the time. What should I do? Does dressing make me gay? I do dream of sucking a big fat cock a lot. Maybe I'll answer one of the guys.
Caught in hers and compromised
By BillyBoy 21 Jan 2022
Jim noticed I was wearing nylons and a bra. He used my embarrassment to his advantage.
Chis(topher) & Chris(tina) (ch. 5)
By djfmonkey 20 Jan 2022
What happens after the corporate holiday party and events leading up to an unusually interesting Brunch with Chris' Boss
Chis(topher) & Chris(tina) (ch. 4)
By djfmonkey 19 Jan 2022
After visiting my mom and dad, Chris and I get invited to his very conservative corporate Holiday Party, how can he attend and not bring me.