He came up behind me
By sandybotm 31 Mar 2025
You never know what can happen when you chop veggies in a skimpy outfit.
Gay Crossdressing Stories
GayDemon's gay porn library: in this story category you can find erotic stories with crossdressers and crossdressings.
Fantasy fulfilled, or nightmare realized
By PnwRobert 28 Mar 2025
Fantasy fulfilled or nightmare realized, closet crossdresser gets more than they bargained for...or did they.
Doing It For Daddy
By JessiW 24 Mar 2025
What do you do when you hear strange sounds at night? On a hot, restless night. This one is strictly fantasy.
Sissy Dad's Awakening
By ThePerfectcameltoe 21 Mar 2025
Chapter 1: A Hot Mess. In this chapter, an alpha son named Boland receives a distress call from his omega father, who's struggling to cope with a chaotic situation. Desperate for support, the omega dad reaches out to his son, seeking refuge and a temporary place to stay for a few days, hoping to find solace and stability with Boland.
Into the looking glass
By Okamaguy 16 Mar 2025
An unplanned visit to an unprepossessing suburban gay bar changes a 19-year-old English femboy’s life.
Pretty in Pink (ch. 3)
By Prettyboy 13 Mar 2025
Pink has just bought a pair of pink leather hi top Nikes and feels so hot on them. She can't wait for Rick to get home so he can fuck his femboy in her pretty pink boots
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
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.
Caught in her panties by my mean stepfather
By BillyBoy 6 Mar 2025
George finds me in panties. Then the real trouble really begins
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.
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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.
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.
Closeted Crossdresser
By slut4roughuse 15 Feb 2025
Blackmailed crossdresser sissy used by neighbor
Gay sissy hookup with daddy dom
By BillyBoy 15 Feb 2025
Incest finds its way into a dark dungeon of a man
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.
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.
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!
Muscle Boy Girlfriends
By Clark Wayne 22 Jan 2025
Enemies to Friends story of two very competitive football players, teammates, each harboring a subconscious desire for each other, realized after dating the same girl. She introduces them to a kink they didn't know they had. Muscle and Lingerie combine and the contrast is amazing.
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.
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.
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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.
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.
From boy to bride
By Wanna be Submissive 11 Dec 2024
Story of conversion of Shivam to Shivani
My first time with Terrell (ch. 2)
By pawb bunny 7 Dec 2024
The days following
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
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.
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.
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.
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
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!
Want more porn with crossdressing men?
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About our sissy crossdressing stories
GayDemon Story Library has been online since 1999 and is currently the best source of gay erotic stories you can find. All the gay sex stories with transvestites and sissies in this vast archive are available to read and download for free. Individual authors create and upload the gay erotic stories you will find here in our story archive. Please respect their copyright and do not repost these creations without obtaining permission from the writer first. If you like a particular crossdressing short story or novel, don't forget to rate and leave a comment to express your appreciation.