49 Votes
Wife discovers husbands sissy secret
Wife forces husband to embrace his sissy side after she discovered his secret stash
Topics: Anal Sex, Crossdressing, Dildo, Threesome, Sissy, Domination, Husband
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.
Wife forces husband to embrace his sissy side after she discovered his secret stash
Topics: Anal Sex, Crossdressing, Dildo, Threesome, Sissy, Domination, Husband
The door opens and a dark, hunky, broad guy enters. I am happy that it is not someone I know. Well, he is a tattoo artist and a friend of Master.
Topics: Crossdressing, Master & Slave, Domination
When I first got started in general with crossdressing my childhood bestfriend help my development all the way around
Topics: Anal Sex, Crossdressing, Big Dick, Sissy, Oral & Blowjobs
Please please please give me your thoughts I am trying to get back into the gay scene after a 13 year absence
Topics: Crossdressing, Chastity, Panties, Fucking
A hot hunk house help becomes the master to a newbie in a city . See how it happens!!
Topics: Crossdressing, Big Dick, Master & Slave, Domination, Submission, Houseboy
Visiting a hotel bar during a gay drag queen weekend, I become involved with some dominant crossdressing ladies
Topics: Crossdressing, Seduction, Oral & Blowjobs
My real Vegas trip:)
Topics: Crossdressing, Threesome, Hotels, Travel, Sex
Daddy’s hold on me gets stronger - my lessons continue
Topics: Crossdressing, Daddy, Cruising, Oral & Blowjobs
Having all the sissy's in town show up wasn't as hard as I thought
Topics: Crossdressing, Sissy, Oral & Blowjobs, Lingerie
my study buddy caught me playing in my sisters underwear
Topics: Crossdressing, Forced, Blackmail, Oral & Blowjobs, Socks, Lingerie, Panties
My dream come true
Topics: Crossdressing, First Time, Friends
Overwhelmed from the last encounter, sissy Julie returns to the woods
Topics: Crossdressing, Daddy, Cum, Sissy, Oral & Blowjobs, Domination, Submission, Facial, Feminization, Cum Swallow
Living at home with my parents still my eager 19 yr old was begging for some type of action late at night
Topics: Crossdressing, Big Dick, Daddy, Sissy
A closeted ex-con biker queer marries a heterosexual woman to the lustful amusement of the colorful cocks they have in common.
Topics: Black Men, Anal Sex, Crossdressing, Straight Men, Dildo, Creampie, Bisexual, Interracial, Bareback, Straight Sex, Cuckold, Gangbang, Redhead, Lingerie, Fucking
An ex-con turned repo man gets entangled with his older bosses and his housemates.
Topics: Black Men, Crossdressing, Straight Men, Brothers, Hairy men, First Time, Transgender, Daddy, Top to Bottom, Age Difference, Size Difference, Married, Boss, Blue Collar
A gay ex-jock with a lingerie fetish graduates from college and returns home to see his high school football coach. The college grad learns his coach has always wanted him and has always known about his kink.
Topics: Muscle, Crossdressing, Coach, Jock, Sissy, High School, Age Difference, Lingerie, Footballer, CNC
A crossdressing queer becomes a cum dump for his dominant father.
Topics: Crossdressing, Spanking, Forced, Incest, Cum Dump, Dad & Son, Spit, Smoking, Married, Cigar
Everyone has a pervy uncle, but it turns out, I am the pervy uncle
Topics: Crossdressing, Uncle, Incest, Sissy, Sex, Nephew
He bent over the bed, he lifted his red skirt, there were his pink panties with a slit for easy accesses to his ass hole. I smeared my cock with Vaseline and then rammed it in the panty slit into his ass. His slutty chute parted smoothly to accommodate my hard thick eight inches. He had blossomed as a girl.
Topics: Crossdressing, Public Sex, Prostitution, Slut, Interracial, Alpha Male, Historical, Age Difference, Domination, Gangbang, Office Sex
After finally taking Danyl's cock, "Jess" is ready to submit totally. After a trip to the gym, things don't end up going according to plan, and Jess's level of submission to the life of being a sissy is tested.
Topics: Anal Sex, Crossdressing, Chastity, Voyeurism, Sissy, Bareback, Roommate, Blackmail, Oral & Blowjobs, BBC, Femboy, Fucking
Been looking. I guess guys aret really into a panyboy unless they are young and pretty. I'm not either of those. But I'm willing, obediant and fun!
Topics: Crossdressing, Sissy, Oral & Blowjobs
My wife catches me in her underwear. She tells her friends. One of her friends husband call me. Then it begins.
Topics: Crossdressing, Sissy, Oral & Blowjobs, Lingerie
In the beginning my 2 older sisters teased and taunted me. At the same time, mom's and their girly underwear was everywhere.
Topics: Crossdressing, Bondage, First Time, Lingerie, Panties
Young Lawyer gives special service in building of Biltmore Estate
Topics: Crossdressing, Interracial, Historical
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."
Topics: Crossdressing, Straight Men, Threesome, Uncle, Transgender, Incest, Sissy, Cum Dump, Grandpa, Dad & Son, Redneck, Stepdad, Gangbang
Read how ron and hema had their first encounter. second part coming soon
Topics: Asian Men, Crossdressing, Romance, Hotels, Sex, Fucking
Waking up next to chelsea after a night with her brother mark and friend Lamar
Topics: Anal Sex, Crossdressing, Big Dick, Sissy
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.
Topics: Crossdressing, Forced, Transgender, Incest, Sissy, Cum Dump, Dad & Son, Virgin, Rape, Degradation, Spit, Violence
James, otherwise known as Jess, moves into campus and finally gets to meet Danyl. Over the course of one day, does their secret already get out?
Topics: Crossdressing, Chastity, Poppers, Big Dick, Sissy, Bareback, Raunchy, Nipple Play, Femboy, Fucking
The two football players score a hook up with one of Toby's fuck buddies.
Topics: Crossdressing, Rough Sex, Threesome, Coach, Age Difference, Lingerie, Footballer, Panties, Fucking, CNC