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.
An unusual tale of a sissy named Samee impregnated by her late stepbrother, only for her stepfather to be fingered as the baby's father. To get "her" out of her stepfather's grubby grips, she is sent to live with her estranged father and his new girlfriend before being passed off to her paternal grandfather and uncle in the classic cliche of "out of the frying pan, into the fire."
Arin knew his father never liked him. His other sons were men and Arin felt more like a girl and dressed accordingly. Her world starts to unravel when things goes bust with her boyfriend and her father decides to violently pluck her cherry.
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.
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.
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
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 whore who died drowning on a load.
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.
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.
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.
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.
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.
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.
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)
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…
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
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 .
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.
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.