Gay Crossdressing Stories

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

Keds Bitch (ch. 15)

By Prettyboy 10 Mar 2025

After having hot sex, Tom and Jackie spend weekends together. In the morning they start with Tom licking the soles of Jackie Keds while Jackie blows him. Later in shower Tom pees on Jackie's pretty ass who loves the taste of Tom's urine when she sucks his dick

9.3 (2) 462 3 Min Comments

A Deal's a Deal

By Sissyboi69 8 Mar 2025

Jack finds out something he did to his girlfriend in the past has finally caught up to him... and now he has to pay the price.

8.7 (92) 9954 10 Min Comments

Caught in her panties by my mean stepfather

By BillyBoy 6 Mar 2025

George finds me in panties. Then the real trouble really begins

8.0 (34) 5219 4 Min Comments

Meeting a gay sissy for the first time

By BillyBoy 5 Mar 2025

My first encounter with a true gay sissy was very eye opening. She liked it kinky. And being the good friend I am, I did my best to please her.

9.1 (23) 3371 7 Min Comments

Fuck me in my Mary Janes

By Prettyboy 1 Mar 2025

Jackie, a crossdressing bitch, has a new pair of Mary Janes and is looking for a guy wearing high black boots to fuck her. Jeff is turned on my Jackie wearing Mary Janes so they hook up for a hot fuck.

9.0 (9) 720 4 Min Comments

Dad's Book Store

By BJJL 25 Feb 2025

When his son decides to take over the book store, there are some changes dad didn't count on.

8.0 (48) 4038 7 Min Comments

Closeted Crossdresser

By slut4roughuse 15 Feb 2025

Blackmailed crossdresser sissy used by neighbor

9.1 (39) 7410 18 Min Comments

Gay sissy hookup with daddy dom

By BillyBoy 15 Feb 2025

Incest finds its way into a dark dungeon of a man

8.7 (37) 4812 4 Min Comments

Adult Store and Theater experience (ch. 4)

By RiverDylan 7 Feb 2025

Married man finds his true calling and he goes on a mission to get the attention of the man who abused him but also the man that he's in love with.

8.6 (12) 2218 17 Min Comments

Revenge of the gay master

By BillyBoy 6 Feb 2025

I forgot to watch myself when posting rude remarks online. I was found out, and the Gay Master came to visit. He did everything to me that I'd said was crude and disgusting. This a fantasy piece.

5.9 (9) 1604 2 Min Comments

Tyler said he was a top

By BillyBoy 29 Jan 2025

Tyler said he was a top, but he didn't sound stern enough. I was wrong!

8.5 (26) 2020 4 Min Comments

Pounding the Sissy

By Torsten 15 Jan 2025

In a world where strength is measured by muscle, Mick Malone is unprepared for Dorian, the sissy the government sends to assist him with the chores and sexual needs. Their days are marked by Dorian's lewd appreciation for Mick's sweat-soaked body, while Mick's physical dominance is tested by the shameless behavior of the government-assigned sissy.

8.8 (16) 2728 23 Min Comments

Husband decides on drastic action

By Frank Chainges 6 Jan 2025

Husband decides he needs more than most wearing feminine clothes and calls for drastic action.

7.4 (15) 2587 2 Min Comments

Late night mystery man

By BeefyFem 5 Jan 2025

A random online encounter between a femboy and man leads to an evening of passion and excitement.

9.0 (42) 3694 7 Min Comments

Thank you, Mister Townshend (ch. 6)

By Okamaguy 27 Dec 2024

Paige services one of the workmen. She has a narrow escape from an Uber driver and is rescued by Jerry. She puts on her maid costume to service the workman again, sucks his co-worker, and sets herself up for two night of fun alone at the resort before Mr. Townshend joins her.

9.8 (5) 633 18 Min Comments

From boy to bride

By Wanna be Submissive 11 Dec 2024

Story of conversion of Shivam to Shivani

7.2 (22) 6143 3 Min Comments

My first time with Terrell (ch. 2)

By pawb bunny 7 Dec 2024

The days following

9.3 (31) 2843 7 Min Comments

Two Bitches and Their Boss

By Prettyboy 2 Dec 2024

Jackie is living with Jess now. Jackie has a femboy friend, Jimmy, and invites him over so he can enjoy Jess's 7". Jimmy is spit roasted as he sucks Jackie's cock while being fucked

9.0 (9) 2063 5 Min Comments

Control and Corruption

By isaline_cd 20 Nov 2024

A dominant daddy meets up in public with a straight married man. Daddy decides to mark the wannabe sissy as his submissive slut.

9.6 (77) 10528 27 Min Comments

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 (26) 4977 3 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) 2213 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!

7.8 (45) 3381 4 Min Comments

Gaff panty, Cummy shorts, Deep insertion

By BillyBoy 16 Oct 2024

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

7.7 (13) 1869 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.

8.1 (34) 6843 6 Min Comments

CD Hotel sex

By Jester4fun 3 Oct 2024

Sissy CD takes dick in hotel

9.3 (128) 11071 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...

9.0 (21) 11818 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.

8.7 (28) 4776 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 (9) 2983 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?

8.8 (21) 4719 8 Min Comments

How I became an adult bookstore slave

By Filthyslagbag 21 Aug 2024

How I became a bookstore sub

8.9 (109) 10890 5 Min Comments