My second encounter with a guy whom I met in metro
By Hema CD 9 Sep 2020
My second encounter in gay sex with a guy whom I met in metro. Read how we connected met and read the story in detail to know more about the encounter
Gay Crossdressing Stories
GayDemon's gay porn library: in this story category you can find erotic stories with crossdressers and crossdressings.
101
By Nils Huim 27 Aug 2020
A gay bottom has a sexual adventure with a stranger
A Harmless White Nylon Thong
By nylonlingerie 3 Aug 2020
I received a small parcel through the post, not ordered anything from any mail order, so I carefully opened it..
A Sissy Life
By Faedirk 7 Jul 2020
Cat-sitting for your neighbors becomes alot more exciting when you stumble upon their wardrobe collection.
Meetup Gone Crazy
By Luke Holton 16 Jun 2020
After I met a guy at his hotel, him and his team tie me to a bed and chloroform me. Read to find out what happens next
Failed Connections
By Habu 12 Jun 2020
It's all about the pro soccer player's need in fetish play in Denver and Chicago.
my life (ch. 17)
By bijim 10 Jun 2020
a club dancing and developing a crush on a guy
Gay sex change?
By Rubbertransformation 31 May 2020
I love taking cock but often wonder what it would be like to have a pussy instead!
Turn About is Fair Play
By Mikal 30 May 2020
Turn About is Fair Play is a Caesars Bitch Sweet Chrissi cross over both are Detroiters and Jay Jay is mentioned in my 1st Sweet Chrissi as JJ. Anyway Caesar takes his cross dressing sissy boyfriend Jay Jay out they meet Chrissi and things get real naughty.
Sweet Chrissi (ch. 5)
By Mikal 29 May 2020
Dear Rears I really struggled with the decision to allow the Pandemic to be an element in my story. But I am writing a story about a cute sissy that lives in Detroit which has been impacted heavily and so I included it.
Advertisement - Please visit our sponsor!
Muscleboy Double-Teamed in the Gym Shower (ch. 3)
By GameBoy94 9 May 2020
The second part of Jake the muscleboy's steamy molestation on a late-night train car.
I Love Being a Faggot
By cock whore kimmy 5 May 2020
Gary is a cross dressing sissy faggot, and his love of hot, thick, juicy, stud cock has turned him into the biggest little faggot sissy whore! He’s not happy until he’s left cock drunk, with his face covered in cum, and his little asshole is sore and gaping! What a little slut!
Caesars Bitch (ch. 2)
By Mikal 29 Apr 2020
This is a new installment of Caesars Bitch. In this tale Caesar has been with Jay jay for a time and is starting off on his first romance and is cementing his relationship. Yes there is abusive language but we are all grown ups so if you can't handle it move on.
Living my dream (ch. 2)
By SissyBoi 16 Apr 2020
Cute 18 yo femboy crossdresser meets a real man who gives his little boypussy a proper stretching and makes him his bitch
Sacked Quarterback
By Cracker 7 Apr 2020
A macho star quarterback goes from a chick fucker to a cross dressing chick-with-a-dick who gets fucked.
Sissy Transformation
By Mikal 5 Apr 2020
Hi everyone I'm sure many of you are at home board and horny right now. Well I hope I can help relieve some of you with this story about a closeted sissy who meets a mistress that helps him find his true sissy self after he gets in debt to her.
The end of a perfect night out as a sexy woman
By Bob Long 1 Mar 2020
This was the last but ultimately the best part of evening when my girlfriend took me out to a gay club, dressed as a woman just to test the water and to assure me that I not only very passable but also pretty damn hot. I got way much more than I imagined
Gary: The Cock Hungry, Cum Guzzling, Sissy Faggot
By cock whore kimmy 27 Feb 2020
Kim comes home early from work and hears a whore getting fucked in her bedroom. She can only assume her BF Gary is in there cheating on her. So she slips in to catch him in the act, but what she finds in nothing like what she thought. She finds Gary all alone, lying on the bed. He’s wearing some of her sluttiest clothing, and trashiest lingerie. And he’s fucking himself with her favorite dildo.
Before she turned me out
By Bob Long 10 Feb 2020
My girlfriend who fostered my obsession with crossdressing and living as a woman, trained and made me into one hell of a beautiful woman who eventually sucked a mans cock and loved it
How I got started (ch. 2)
By Bob Long 4 Feb 2020
This is a continuation of my glorious introduction to crossdressing and sex
Advertisement - Please visit our sponsor!
Parking lot blowjob
By Bob Long 1 Feb 2020
This is the story of how my ex girlfriend, made it her mission to get me to suck a guys cock
The Art of the Sissygasm
By cock whore kimmy 26 Jan 2020
Little CD fuckdoll has his first sissygasm and his life changed forever!
Caught crossdressing
By SandyCD 6 Jan 2020
Caught by daughter with me dressed as woman
Big Sissy
By Nils Huim 28 Dec 2019
A gay sissy bottom receives a surprise birthday gift
Amateur Crossdressing Prostitute
By Kristen Kross 23 Dec 2019
crossdresser's first time prostituting first timer
A Sissy’s Dream Comes True! Again and again!!
By FishnetSissy 21 Dec 2019
2 blonde bimbos help a little sissy faggot become the girl he always wanted to be and Introduce him to a man who knows just what to do with a special girl like this!
My New Apartment Manager
By Kristen Kross 21 Dec 2019
cd sissy meets her apartment manager
Starbucks
By Nils Huim 16 Dec 2019
Two ex-cons have anal & oral sex and then plot (?) a robbery
Un-Expected Threesome
By Kristen Kross 7 Dec 2019
CD, girl, and a stranger meet in a motel room
holidays with grandad (ch. 2)
By Sisyboy 21 Sep 2019
Part 2 of getting caught