Gay Crossdressing Stories

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

My Halloween crossdressing story

By BillyBoy 19 Nov 2024

I knew I shouldn't, but I dressed in women's clothes again this Halloween. It turned out much different from last year, but the final results were the same. A cock in my mouth and another one in my, you know where.

6.9 (24) 3299 3 Min Comments

Tom, the married security guard took me for a woman (ch. 3)

By Sufficient_Offer 17 Nov 2024

Sam is about to know why Tom's wife really can't take his monster of a cock aymore.

9.7 (73) 5257 9 Min Comments

Sissy's Bizarre Adventure (ch. 4)

By Dray Sandrix 9 Nov 2024

In this chapter, Diana, the newly initiated sissy slave, and her Master, Alex, embark on an electrifying adventure into the unknown. At a BDSM party filled with secrecy and desire, Diana's deepest fantasies are unveiled. Blindfolded and surrounded by eager participants, she embraces her role as "Diana, the Wonder Whore," seeking anonymous encounter

8.7 (9) 1676 6 Min Comments

Caught in hers

By BillyBoy 6 Nov 2024

The gay man catches me in her panties and makes me his bondage fuck toy. I wasn't sure i was going to be ok with it, but, of course, now I love it!

7.7 (43) 2660 4 Min Comments

Gaff panty, Cummy shorts, Deep insertion

By BillyBoy 16 Oct 2024

well, the title says it all. a crazy night indeed

7.5 (12) 1514 2 Min Comments

Closet crossdressing goes very wrong, or did it?

By BillyBoy 10 Oct 2024

Dressed in private but I have to answer the door for my neighbor. It turn out to be a very naughty afternoon.

8.0 (32) 5708 6 Min Comments

CD Hotel sex

By Jester4fun 3 Oct 2024

Sissy CD takes dick in hotel

9.4 (102) 8281 8 Min Comments

My Transformation (ch. 4)

By RiverDylan 19 Sep 2024

Dylan becomes addicted to men, he finds himself a new boyfriend and with that new surprises...

9.1 (17) 9050 19 Min Comments

Spit roasted at home

By BillyBoy 12 Sep 2024

He had me cuffed, wearing a humiliating pink frilly outfit, with a huge nasty purple veined rubber cock in my mouth, and his fat cubby cock fucking my ass from behind. John was kind enough to fulfilled my fantasy for me.

8.8 (25) 3911 4 Min Comments

Miss Jenny from Ohio (ch. 4)

By Okamaguy 28 Aug 2024

Jenny spends the day as a schoolgirl and gets more cock than she bargained for.

9.6 (8) 2618 16 Min Comments

Bound Gagged and Gay'd Me

By BillyBoy 23 Aug 2024

He answered my ad, answered my fantasies, and answered my question: Was it good for you?

8.6 (19) 3923 8 Min Comments

How I became an adult bookstore slave

By Filthyslagbag 21 Aug 2024

How I became a bookstore sub

8.9 (101) 8732 5 Min Comments

Prison Substitute

By Con Twink 21 Aug 2024

A fresh juvenile comes into contact with hardened criminals, and one in particular has a profound influence on him…

6.7 (43) 10991 2 Min Comments

Cruising the Highway

By deansaz 2 Aug 2024

Just on a short drive down the highway when a couple girls began flirting with me from another car on the highway.....

8.3 (24) 2520 3 Min Comments

College and finding the real me

By KellyGirl2010 29 Jul 2024

After graduating high school, I try to figure out who I am and I find that in the arms of another man. Parts of this story are true like my first time panty shopping, going to the adult bookstore, my brother knowing about me wearing panties and the college LGBT Center.

9.1 (27) 3480 23 Min Comments

Call Me a Fuckin Fruit

By Prettyboy 28 Jul 2024

Jackie is wearing a new pair of pink leather shorts with the hopes of attracting a horny top. Jim is a turned on by Jackie's shorts and enjoys her ass both in the gorgeous pink leather and also in the flesh.

8.3 (10) 1149 5 Min Comments

Finally giving in

By ClosetCd 28 Jul 2024

A married husband finally giving in to his desires

9.0 (70) 5434 6 Min Comments

I Love Fucking Femboys

By Prettyboy 26 Jul 2024

Jerry is bisexual but in the end he prefers a femboy's pussy. He meets Tommy who looks so cute in his white leather shorts and Nike Cortez and they hook up for some hot sex.

7.7 (19) 3816 4 Min Comments

Wearing panties

By KellyGirl2010 25 Jul 2024

Sucking my first cock

8.0 (19) 5251 7 Min Comments

BDSM lovers

By BillyBoy 24 Jul 2024

I wander into a sex shop for gay BDSM lovers. I'm in the wrong place!

8.9 (39) 2894 6 Min Comments

Just to Dream a Dream

By luvaslip 20 Jul 2024

Terry arrives at her uncle's house early and lays down for a nap. She dreams a dream that becomes real and gets a lot of loving.

8.9 (11) 1179 2 Min Comments

Twins bothers have lot more in common (ch. 3)

By Xoxo 19 Jul 2024

Harry gave his BBC friends a little show

8.8 (9) 2203 7 Min Comments

Jocks and Panties

By Victor 17 Jul 2024

Branson is a big, muscular, athletic jock who can't understand his need to be treated like an another man's bitch.

9.6 (62) 5553 19 Min Comments

Making the fantasy become reality (ch. 2)

By Try To Be Quiet 16 Jul 2024

Daddy had something planned for me this time, I wondered the whole week waht would happen during our next encounter

8.2 (11) 2123 8 Min Comments

Learning to be gay

By BillyBoy 3 Jul 2024

From playing in panties and shoving a dildo up my ass, I finally found a gay guy to fulfill my desires, fantasies and fetish needs.

7.8 (9) 2748 7 Min Comments

Loving my high heels (ch. 3)

By Prettyboy 27 Jun 2024

Jackie loves wearing high heels. He just received a pair of high black Chucks with 3" white heels. He meets Tom who is turned on by these Chucks and tops Jackie.

9.5 (7) 821 4 Min Comments

Straight guy turned gay (ch. 6)

By Jaden 27 Jun 2024

A new experience - It was Monday morning, I woke up and found myself alone in bed. I found the sexy french maid outfit on bed. I wore it and headed to the kitchen. My master was having breakfast by himself.

9.6 (21) 6011 9 Min Comments

Bent Over

By RedJulian 25 Jun 2024

A cross-dressing bodybuilder slut awaits our narrator at the door.

8.2 (19) 2612 3 Min Comments

All Fun and Games (ch. 2)

By Sam Lil 23 Jun 2024

While the others try to find a way to escape, it becomes clear that the only way for them to leave is to fulfill their task. Michael and Damien seem to be up first.

9.4 (32) 3833 13 Min Comments

Swapping Spit

By luvaslip 23 Jun 2024

Joni joined the Marines and rented an apartment in Carlsbad. She takes a fifteen day leave and meets a neighbor who helps her.

8.4 (12) 927 7 Min Comments