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.
I pressed my lips like a kiss on his asshole and pressed my tongue in. His tight hole pushed it out right away and a hand grabbed my neck. I kept at it and after ten presses his but started letting me in.
Topics: Crossdressing, Forced, Humiliation, Bisexual, Bullies, Oral & Blowjobs
It is a story of a young gay man discovering his needs and desires. Experimentation and first encounters, experiences, and something more.
Topics: Anal Sex, Crossdressing, DP, Group Sex, First Time, Cum Swapping, High School, Oral & Blowjobs, Sixty Nine
Bob and Lacey invite me over to join their swingers' group. But I'm alone with them.
Topics: Crossdressing, Bondage, Rimming, Forced, Oral & Blowjobs, Tricked
I lay in the backseat for a few hours before i hear the car being opened. Hands grab me but something seems off. They throw me face down and i hear the unmistakable sound of a knife switching open. I feel them start to saw away at the tape and before long i am free.
Topics: Crossdressing, Forced, Bisexual, Bullies
Greg searches for submissive sissy type guys on the dating sites. He messages me, seduces me, dresses me in silk and lace, and begins playing in some light bondage. Then he introduces me to his Dom daddy, Bob
Topics: Anal Sex, Crossdressing, Bondage, Rimming, Daddy, Sissy, Domination, Lingerie
Extreme fetish. The bullying gets out of hand.
Topics: Crossdressing, Abduction, Forced, Humiliation, Bullies
Kingsfordland, Tennessee, 1937 — Lollo Aurelie is a city slicker mobster running from trouble up north when he stumbles upon a mountain hick town ripe for a takeover. When moonshiners revolt to his dastardly deeds, they dress him “purdy” in drag and each of his captors have their way with him on a platform deep in the backwoods. They affectionately call him Priscilla Pumpernickel, a late ...
Topics: Piss, Black Men, Crossdressing, Group Sex, Humiliation, Interracial, Sissy, Bear, Redneck, Drunk, BBC, Rape, Degradation, Italian
Christian has turned 18 Years Old, and his friend's sister is interested in him. What happens next nobody could anticipate, Christian becomes a sissy cock-loving cumslut. But how does this happen? Find out by reading The Sissy Transformation of Christian.
Topics: Crossdressing, First Time, Forced, Cum Dump, Boypussy, Mind Control, Virgin, Submission, Gangbang
It is a story of a young gay man discovering his needs and desires. Experimentation and first encounters, experiences, and something more.
Topics: Anal Sex, Crossdressing, First Time, Cum Swapping, Cum, High School, Oral & Blowjobs, Shaved, Sixty Nine
After our first encounter, he was getting hungry again for some of my ass. After a month, I saw some new packages was sent to me. As I opened them, noticed there are some new sexy lingeries and dresses with panties.
Topics: Crossdressing, Sex, Lingerie
An elder gentleman finds new lust
Topics: Crossdressing, Daddy, Seduction, Submission
Every household needs both roles determined. I’m the husband, you’re the wife. You’re my Princess, I’m your King. This is the dynamic King and Princess decide to show off to the world.
Topics: Crossdressing, Romance, Sissy, Sex, Fucking, Feminization
Hendry is an ambitious femboy
Topics: Crossdressing, Daddy, Femboy
When my drag queen friend falls a sleep early and I'm left with her brother and best friend.
Topics: Anal Sex, Crossdressing, Threesome, Interracial, True Story
I am a married man who met a guy at a party. The guy wanted to have sex with me in lingerie. That is, he wanted me to wear lingerie. I didn’t think I would like it. But it was amazing.
Topics: Anal Sex, Crossdressing, First Time, Lingerie, Panties
Two teen football studs have a secret. Both dated a girl who introduced them to butt play. She eventually adds in panties to the mix. When the guys find out about each other, they explore their new kink together.
Topics: Anal Sex, Crossdressing, Bisexual, Ass Play, Lingerie, Footballer, Panties, Fucking, CNC
Everyday to work I would see the same homeless pitching quite the tent in the morning from sweat pants
Topics: Crossdressing, Big Dick, Interracial, Sissy, Homeless, BBC
Five minutes into his new job and Daniel already has an attitude. Ralph warns him against being disobedient during his job orientation, but perhaps his warning was too harsh. He didn't mean to upset his new employee, but he did find Daniel's crying face kinda cute.
Topics: Muscle, Crossdressing, Straight Men, Humiliation, Jock, Co-worker, Big Ass, Size Difference, Degradation, Boss, Illustrated
When he said I don't know I think 6 inches when I asked how big, I should of known that was a lie
Topics: Crossdressing, Big Dick, Interracial, Sissy, BBC
We almost get away with it, but Lars' friends find us and want a piece of the action. This is another long read, but with a ton of sex.
Topics: Anal Sex, Crossdressing, Public Sex, Outdoor, Sissy, Bareback, Oral & Blowjobs, Age Difference, Domination, Young Top, Lingerie
A mature sissy encounters a young top and his friends in the woods while walking the dog. This is a longer read and my first story, so I'm grateful for any feedback.
Topics: Anal Sex, Crossdressing, Public Sex, Bareback, Age Difference, Domination, Young Top, Lingerie
A sheltered an innocent south asian teen with a mostly absent finder finds his Superior White Daddy on the fledgling internet in the early 90s. Can Instructor Mike mold the little peepee girl into his perfect sissy to service his Tremendous White Cock? Class is in session for little aimee. (Parts 1-6)
Topics: Asian Men, Crossdressing, CBT, Enema, Sissy, Role Play, Age Difference, Rape, Discipline, Domination, Ass to Mouth, BDSM, Raceplay
Been a delay but here is the continuation of the whore Heather
Topics: Crossdressing
College athlete wears lingerie for two bodybuilders from his gym.
Topics: Muscle, Crossdressing, Threesome, Sissy, Underwear, Domination, Lingerie, Kissing, Panties, Fucking, Bodybuilder
Brad takes Daniel to the gym to start his new job. Daniel is reluctant to work for sweaty gym bros, but needs the money. Unfortunately, the only gym clothes that fit Daniel are Brad’s Ex’s pink halter top and Juicy track shorts. Daniel is not pleased…
Topics: Muscle, Crossdressing, Humiliation, Jock, Gym, Exhibitionism, Big Ass, Size Difference, Degradation, Illustrated
Meeting strangers for sex is a world in itself . Most men attending outdoor cruising areas are not crossdressers but have a range of sex desires which have to be approached appropriately
Topics: Crossdressing, Cruising, Sissy, Panties
I cruise for the first time and learn what that involves .
Topics: Crossdressing, Cruising, Sissy, Exhibitionism, Lingerie, Panties
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