The Cunting of Lucas (Lucy) (ch. 14)
By GWSHomo 8 Jun 2026
Lucy's first two days without Daddy there to guide and use her turn out to be pretty interesting.
Gay Crossdressing Stories
GayDemon's gay porn library: in this story category you can find erotic stories with crossdressers and crossdressings.
Keds Bitch (ch. 17)
By Prettyboy 2 Jun 2026
Jackie is a pretty boy who likes wearing tight white denim shorts with his white Keds. He meets Jess, wearing high black cowboy boots, who knows to enjoy the ass of twink with his mouth and cock
Stepbro Catches Secret Slut (ch. 3)
By ANSH 1 Jun 2026
I pulled out. Josh made a sound—half gasp, half whimper—and his hole clenched around nothing, already missing the fullness. A thick string of pre-cum and lube connected my tip to his entrance before it snapped and dripped onto the floorboards.
I realize my bitchiness in my open toe booties
By Prettyboy 21 May 2026
Jackie, a pretty femboy, loves wearing ankle high red leather booties with open toes to show off his pink nails. Jackie's partner, Ron, enjoys fucking kissing Jackie's painted nails while he fucks Jackie
Midnight Saree
By Priyanka 12 May 2026
A straight cuckold son, turned into a sissy slut of old drunken man
Abusive Sissification (ch. 5)
By Kavya sissy 22 Apr 2026
It’s chapter 5 and I’m being fucked abused and tortured in the middle of the street, the abuse continues…
I keep coming back for more
By BillyBoy 22 Apr 2026
He told me he was surprised I wanted to come back for more. I couldn't answer him because I don't know myself.
Making of a Good Girl
By CollarBound 17 Apr 2026
Story of how I became over time coerced into becoming a good girl and owned by a man.
Finally met a guy i could kiss
By BillyBoy 15 Apr 2026
A married straight couple invited me for some fun. Turns out she wasn't into doing anything but giving orders and watching. He was into wearing her underwear, and into me.
Feeling Good in My Skirt and Heels (ch. 3)
By Prettyboy 6 Apr 2026
Jackie's new pink leather skirt has just arrived. After fucking himself with his dildo he hooks up with a leather man who is turned by femboys and Jackie in his pink leather skirt and knee high white patent leather boots
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Crossdressing and bondage
By BillyBoy 26 Mar 2026
I finally found a guy to help me with my fantasies. Then this happened!
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.
Black Alpha now owns me as a gloryhole slave
By tiffanyobeys 21 Jan 2026
Tiffany tgirl find her destiny as a cheap , gloryhole slave
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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
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?
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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.