GayDemon's Stories: On this page you can find erotic fiction where you can read about men dressing up as women and gay sex with transvestites and crossdressers listed by date.
A custodian at high school who had made a pass at me was remembered as being the only person I was sure was homosexual and as my crossdressing urges grew stronger he became the focus of a plan to act them out . What follows is true .
Topics: Crossdressing, Underwear, Lingerie, Panties
A bad encounter leads to another break and a lot more cross dressing exploration
Topics: Crossdressing, Drugs, Sissy, Domination, True Story
I’ve never thought about of gay sex in my life so far. But one night it changed. As usual boring weekend, I was scrolling through some porn and all of a sudden, some hypno sissy gay porn videos kinda got my attention.
Topics: Crossdressing, Sex, Lingerie
Nick thinks he has to be the most unlucky person in the whole world, not only has he traded three masters for one, the one seems to be more sadistic than the three combined. To add insult to injury, Oliver's friend is now living in Nick's house, with seemingly no way out for Nick.
Topics: Crossdressing, Bondage, Stripping, Humiliation, Exhibitionism, Rape, Illustrated
How I found out I really liked dressing as a girl. My mom was my inspiration. I became the fourth girl in the family.
Topics: Crossdressing, Masturbation, Incest
A family friend catches me in panties and heels, and I have to pay for his silence
Topics: Crossdressing, Daddy, Sissy
How I turned a sexy chat into super hot sex with a man for the first time.
Topics: Crossdressing, First Time, Daddy, Sex
This is a story of how my normal life changed and i became an obedient sissy for, my master.
Topics: Anal Sex, Crossdressing, First Time, Sissy, Master & Slave, Submission
The merging of two of my stories published on another site. Two feminized sissies are sold to dominant sadists who plan to use and abuse them for their pleasure.
Topics: Anal Sex, Crossdressing, Rough Sex, Bondage, Fisting, Forced, Sissy
Part 3 follow-up on "A normal relationship turned into a wild weekend orgy". The names and places of this story are not real.
Topics: Anal Sex, Crossdressing, Group Sex, Transgender, Bisexual, Slut, Cum, Sissy
Part 2 follow-up on "A normal relationship turned into a wild weekend orgy". The names and places of this story are not real.
Topics: Anal Sex, Crossdressing, Group Sex, Transgender, Slut, Cum, Sissy
A 3 part follow-up on "A normal relationship turned into a wild weekend orgy", the next time we all got together for an amazing vacation. The names and places of this story are not real.
Topics: Anal Sex, Crossdressing, Group Sex, Slut, Cum, Sissy, Oral & Blowjobs
Continuation of the story "A Normal Relationship Turned Into A Wild Weekend Orgy" This is the events of the said weekend,
Topics: Anal Sex, Crossdressing, Group Sex, Slut, Cum, Sissy, Oral & Blowjobs, Orgy
When I was 19 I moved to the big city for university, this was my first time living alone. I considered myself a normal man, even had a girlfriend for a bit, but I always knew I wanted more. I have always been interested in men and wanted to sleep with one. I was also fascinated with sissies and liked women’s clothes. Now to the story..
Topics: Anal Sex, Crossdressing, First Time, Oral & Blowjobs, Boyfriends, Orgy
An unexpected surprise, that led to an interesting experience
Topics: Crossdressing, First Time, Uncle
After we met first time at hotel we started talking about fantasy of each other and started fulfill them. So this was his first fantasy.
Topics: Crossdressing, Sissy, Grandpa, Hotels, Sex, Master & Slave, Grindr
All that rises must converge -- between two worlds of slavery. Charles philosophizes, and reveals a bit of his evil character not yet presented. The relative nature of things in the world with good and evil and men's belief's. Fist fucking a girl. Charles makes a break through and finds his slave.`
Topics: Anal Sex, Crossdressing, Forced, Humiliation, Master & Slave, Rape, Domination
A full bus load of slaves. Master Charles is dispairing of slaves location. Slave Paul becomes slave Pauline. The girls are reminded of how important it is to be lady like.
Topics: Crossdressing, Abduction, Humiliation, Drugs, Twink, Master & Slave, Domination, Body Modification
A young traveler's car breaks down and he finds himself tied down to a kitchentable, crying and loosing his anal virginity.
Topics: Anal Sex, Crossdressing, First Time, Forced, Virgin, Rape
Daddy has fun surprises in store for his boy princess as they mix business and pleasure in Palm Springs
Topics: Anal Sex, Crossdressing, Daddy, Boypussy, Lingerie
Tall, massively muscular Brodin is a no nonsense bottom with many fuck buddies. One night a married fuck buddy asks him to slip on a pair of panties. To Brodin's surprise, he likes it and so starts a new kink for the big, broad bodybuilder.
Topics: Muscle, Crossdressing, Role Play, Lingerie, Married, Bodybuilder
I get fucked and like it!
Topics: Black Men, Anal Sex, Crossdressing, Bondage, Interracial, Sissy, BBC
Like a bitch
Topics: Crossdressing, Daddy
My name is Sissie it used to be Matt, but that name doesn’t fit. I just put up a sissy pride flag in my window. Mine has pink and white stripes with a modified phallus symbol that looks like a heart with a limp arrow jutting out of it.
Topics: Crossdressing, Sissy
Although this is ch 4 , it is the 2nd part of the Jill Jordan story.
Topics: Crossdressing, Cruising, Sissy, Breeding, Anonymous, Submission, Stranger
The Rest Stop Digest . This is one of many stories I have written through out the years. Most of these stories are real experiences. Some of these stories are about different people, but they are based on real event and told as close to a Accurate as possible. This is a true story but the names have been changed ..
Topics: Crossdressing, Cruising, Cum, Sissy, Oral & Blowjobs, True Story, Stranger
How I became a sissy slut addicted to big black cock
Topics: Crossdressing, Humiliation, Slut, Interracial, Sissy, BBC
I finally found someone that could help me fulfill my desires.
Topics: Crossdressing, First Time, Sissy
CD Cumpdump and fun freak meet up
Topics: Crossdressing, Cum Dump, Bareback
I Was thinking about Tony' s cock, and as I slid a black lace g string up to my hips and tucked my clit back.
Topics: Crossdressing, Sex