Crossdressing and bondage
By BillyBoy 26 Mar 2026
I finally found a guy to help me with my fantasies. Then this happened!
Gay Crossdressing Stories
GayDemon's gay porn library: in this story category you can find erotic stories with crossdressers and crossdressings.
The Cunting of Lucas (Lucy) (ch. 5)
By GWSHomo 18 Mar 2026
Lucy's first day with her newly formed cunt comes to a close. But will tomorrow bring new challenges?
Straight to femboy (ch. 2)
By Gay Erotic fantasy stories 17 Mar 2026
My roommate becomes Daddy and I become his cute little femboy
The Bimbo Maker (2025 Remix)
By CdJenny 17 Mar 2026
Chris, a straight college student, takes a bet with his friend Rick, who claims his cock has a supernatural power over men. If Chris can resist its allure for 24 hours, he wins $500. But as the hours pass, Chris undergoes a shocking transformation, his body and mind reshaping into a perfect bimbo, consumed by an uncontrollable obsession with Rick’s
Jessica
By KellyGirl2010 3 Mar 2026
My friends roommate...
Being owned (ch. 6)
By Chocolate_Boo 19 Feb 2026
Taking control of his/her whole being
Men, Bondage and Discipline
By BillyBoy 18 Feb 2026
how i started becoming a sub bitch for so many dom men
The Guy With The Long Hair
By Mark Blazer 16 Feb 2026
Soccer stud falls under the spell of a femboy sissy slut.
A Transformative Encounter
By Joe Lewin 8 Feb 2026
A businessman has his first T-Girl encounter.
Getting My Nails Done
By Prettyboy 27 Jan 2026
Ricky a femboy likes to look pretty for his partner, Steve and has his nails done by a Teddy. Teddy and Ricky end up being eager bottoms for Steve who fucks them and pisses on their asses in the shower.
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Black Alpha now owns me as a gloryhole slave
By tiffanyobeys 21 Jan 2026
Tiffany tgirl find her destiny as a cheap , gloryhole slave
Big black Ass Grandma and Son (ch. 2)
By Dondee 21 Jan 2026
Fucked by the football team
My anonymous meet turns out to be not so anonymous
By Filthyslagbag 16 Jan 2026
Anonymous meet turns out not so anonymous as straight acting discreet guys who know each other accidentally meet up for a filthy meeting
I Love my Bitch in Heels (ch. 2)
By Prettyboy 7 Jan 2026
Jake loves to top his bitch Jeff wearing boots whileJeff wears a skirt and boots with 3" heels. Jake leaves his cum in Jeff with his hole sealed with a jeweled butt plug. He takes the plug out in the morning and pisses on Jeff ass in the shower.
Jamie is a useless sissy
By DirtyDumbSissy 13 Dec 2025
Jamie is a toilet slut meth addict...
Caught Crossdressing
By BillyBoy 4 Dec 2025
You don't hear about these sorts of things actually happening, but they do, Caught by a pervy in my wife's panties and bra. Oh No!
Tiffany trans begins her journey as a chained slave
By tiffanyobeys 1 Dec 2025
Tiffany begins on her new life as a chained sex slave. She will be trained as a human toilet and fisted/stretched and prolapsed
Trans gurl Tiffany is abducted by powerful Arab men (ch. 2)
By tiffanyobeys 30 Nov 2025
The continuing saga of Tiffany Tgirl , abducted in to slavery by Alpha Arab men. In this episode , we see her becoming a human toilet
The Party of Thirteen
By Barry 23 Nov 2025
After connecting with a former sexual partner on Grindr, went to meet him at his friend's place. Upon arrival, two other men were present. The Grindr date and the narrator had sex, but then the second and third men also had forceful sexual encounters with the narrator.
The Chronicles of Alex
By Andrealegscd 21 Nov 2025
Alex is now 18 after many years of crossdressing and discovering his feminine self he is totally out and becoming more feminine by the day , taking hormones has aided the changes in his body and opened up lots of possibilities for sexual fun
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Playboys
By Victor 17 Nov 2025
A frat initiation goes sideways for one straight frat boy. Forced to waitress an alumni party while scantily dressed, brings a realization that he may be repressing his true sexual nature.
Rocky Horror
By Victor 14 Nov 2025
Straight, frat boy Colt has never been to the Rocky Horror Picture Show, but his buddies assure him that it's perfectly normal to wear costume lingerie. When he catches the eye of an alpha Marine, he starts to wonder if he actually likes that attention he's getting dressed in slutty lingerie.
BBC Cum Diet (ch. 2)
By Sissyslutgurl69 12 Nov 2025
Part 2: Femmie whiteboi continues cum-only diet.
Femoby catfished by a Femdom and her Lover
By Sissyslutgurl69 11 Nov 2025
Feminized sissy gets tricked by an aggressive mean Femdom.
Curious turns into first time guy on guy sex
By sissyjackie 5 Nov 2025
Was curious for years finely took the plunge had gay sex
Does wearing pantyhose and a bra make me gay?
By BillyBoy 28 Oct 2025
Confused as to why I feel like I should be sucking a man's cock when I'm just wearing a pair of ladies pantyhose and a cute little push up lace bra???? Am I gay?
I Love My Pretty Pink Boots
By Prettyboy 27 Oct 2025
Jackie has a fetish for boots and hi top sneaks. She has several pink boots that are a turn on for his partner Jeff. The story describe Jackie's day and the hot sex she has in her pretty pink boots.
Rahul's Sissy Awakening Under Master Ansh (ch. 7)
By ANSH 16 Oct 2025
The story comes to its final chapter read how both Ansh and Vikaram uses Rahul
My first top experience
By Loves black men 12 Oct 2025
How a young curious male discovering his bisexuality met his first top. How a masculine man can be transformed into a cross dressing bottom in the bedroom. First time experience that lasted 10 and formed his love for BBC and the bottom experience.
Romantic Fem Bottom
By sandybotm 9 Oct 2025
It's late at night. They need each other. Both horny for each other and can't wait. He loves being fem to a strong top.
Used the wrong medication
By Frank Chainges 7 Oct 2025
Needed to enlarge my manhood and bought some meds off the internet.. results were NOT what I expected
Feeling Good in My Skirt and Heels (ch. 2)
By Prettyboy 5 Oct 2025
Jeff loves seeing Jackie in skirts and has bought one for her in black leather. It looks so hot on Jackie they have sex. They go out shopping and buy a longer blue skirt with flowers with leads to another round of fucking.
Didn’t know it was a gay bar (ch. 3)
By Alleykat 27 Sep 2025
Drugs blackmail sissyboi
I Love Wearing Laced Panties
By Prettyboy 9 Sep 2025
Jackie got hard the first time she put on white laced panties and came in them. He partner Jeff is turned by Jackie wearing her laced panties and her pretty pink Nike boots. They enjoy sex with the white lace and pink boots and finish with Jeff pissing on Jackie's laced ass.
My very first time broke the rules
By Remember 6 Sep 2025
This was my first unplanned encounter and he broke the rules,
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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.