Gay Crossdressing Stories

GayDemon's gay porn library: in this story category you can find erotic stories with crossdressers and crossdressings.

Sissy photo shoot peril

By BillyBoy 25 Mar 2022

The guy was a bad photographer and an even worse perv.

9.1 (21) 3384 8 Min Comments

Becoming me

By BillyBoy 22 Mar 2022

Confused and horny I meet another guy in a kinky threesome. And then, I become me.

8.4 (10) 2976 3 Min Comments

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.

8.5 (66) 7278 7 Min Comments

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?

8.1 (18) 2408 6 Min Comments

Internet site gone wrong, or not.

By BillyBoy 5 Mar 2022

Someone recognized me from the post in GayDemon! Maybe I was hoping that would happen?

8.0 (22) 4495 4 Min Comments

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.

7.5 (19) 5371 3 Min Comments

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.

9.2 (11) 2630 67 Min Comments

Dressed to Thrill At The Club

By lickme 28 Feb 2022

Getting slutty and hot a gay club for the first time

8.5 (14) 3304 3 Min Comments

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.

9.4 (23) 3753 4 Min Comments

First Date Dressed To Kill

By lickme 24 Feb 2022

Dressed to Kill! First date with stranger and ready for seduction!

8.9 (22) 2738 3 Min Comments

Cock Dreams Come True

By lickme 21 Feb 2022

Hetero guy with kinky man to man fantasies

7.7 (12) 2241 3 Min Comments

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.

7.8 (22) 7544 10 Min Comments

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.

9.0 (66) 8754 11 Min Comments

Trying on a few new things

By BillyBoy 4 Feb 2022

Another Halloween is here! Maybe this year I'll catch my first man!

9.4 (21) 2494 11 Min Comments

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.

8.0 (36) 4580 5 Min Comments

American cross dresser in Europe

By WLASteve 26 Jan 2022

A 2006 solo trip to European is a fulfillment of a lifelong dream

9.2 (23) 2357 7 Min Comments

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.

8.0 (16) 2705 9 Min Comments

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.

8.9 (39) 6226 6 Min Comments

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

9.7 (116) 2423 5 Min Comments

Tell me you love me

By BillyBoy 19 Jan 2022

He was great. He followed all my requests. A dream come true.

7.3 (9) 1099 2 Min Comments

Crossdresser makes homeless man happy

By Paulacd 17 Jan 2022

I had gotten dressed very sexy and slutty one night being completely hairless permanently except for my eyebrows eyelashes and long hair on my head.

7.5 (28) 4354 3 Min Comments

Becoming a sissy crossdresser for him

By BillyBoy 15 Jan 2022

I started wearing moms underclothes when I was younger. They were always laying around in her bedroom and in the laundry. But later I discovered he was leaving them around for me to find. He was tricking me into becoming a sissy crossdresser for him.

8.8 (40) 11801 13 Min Comments

Prom going wrong

By BillyBoy 11 Jan 2022

I dressed like a girl for prom. My friend Jeff and I didn't have proper girl dates. It was sort of a joke and a few of the other boys were doing it. And Jeff's dad seemed to like me a lot.

8.9 (67) 7093 4 Min Comments

Blackmail

By Victor 10 Jan 2022

Decker has found out his nemesis, Fitch, another closeted jock, has been hooking up with a male escort/cam boy. Now he intends to get what he wants from the gorgeous jock by blackmailing him.

9.3 (120) 10625 22 Min Comments

Big black sissy Crack whore

By Big Black sissy 9 Jan 2022

My life that i want

7.5 (21) 12220 20 Min Comments

I'm his bound and gagged girlfriend

By BillyBoy 6 Jan 2022

She told her friends I wanted to wear her underwear and be tied up when we had sex. It was a weak moment for me. I shouldn't have asked her. I was young and didn't know any better. She didn't appreciate my wishes at all. That was it for her, and most any other chance I may have had with a girl. But, she handed me off to someone who did appreciate my fantasy. For better or worse!

8.6 (28) 4912 5 Min Comments

After Halloween

By BillyBoy 30 Dec 2021

I wore a girl's dress as a joke to a Halloween party. It was all in fun. Wives and girlfriends were there. But after that, I got a few uncomfortable calls and texts from a few of the men who saw me.

8.9 (58) 11046 9 Min Comments

bondage blowjob

By BillyBoy 28 Dec 2021

I woke up in his bedroom, wearing his wife's wedding lingerie. I'm on my knees with his cock in my face. What now?

8.5 (22) 4979 5 Min Comments

Santa Rosa Slut

By bootlicker 27 Dec 2021

A young drifter in Palm Springs is taken in and trained as a sissy, a slut, a slave, and a boi-whore by two older men and their friends.

9.1 (26) 6417 20 Min Comments

Cross dresser.. Twink.. Tranny?

By djfmonkey 22 Dec 2021

My straight buddy and I visit a gay bar, where we discover our own inner selves, and the truth about each other

9.3 (166) 7754 8 Min Comments