18 Votes
My first time with a man
How I turned a sexy chat into super hot sex with a man for the first time.
Topics: Crossdressing, First Time, Daddy, Sex
GayDemon's gay porn library: in this story category you can find erotic stories with crossdressers and crossdressings.
How I turned a sexy chat into super hot sex with a man for the first time.
Topics: Crossdressing, First Time, Daddy, Sex
My sissy journey from a boy to a sissy whore.
Topics: Humiliation, Sissy, Submission
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
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
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
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
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
I venture out to explore my sexuality, and meet a more experienced crossdresser and her friend. He takes us both and uses us well. This is a true story.
Topics: Crossdressing, Sex, True Story
My hot DILF CEO is an alpha with a soft side when we're alone. The older muscle stud wants nothing more than my younger, muscular body to dominate him and make him my bitch.
Topics: Crossdressing, Threesome, Sex, Age Difference, Domination, DILF, Lingerie, Boss, Kissing, Fucking
The true story of one of my favorite guys from Craigslist. He was a horny young soldier just looking to come. Of course I eagerly offer my mouth and ass to him.
Topics: Anal Sex, Crossdressing, Oral & Blowjobs, Hookups & Dates
"If it's not a big deal, then you do it," I said. He shrugged and got up, going to the box. He dug around until he came up with another bra, a little nicer than the one I was holding, pink lace and pink satin. He held it up and then slipped his arms through the straps, holding it against his chest, over his shirt. He tried to reach around back to close it, but couldn't...
Topics: Anal Sex, Crossdressing, Fucking
A sissy wants to show off her new panties
Topics: Crossdressing, Daddy, Sissy, Bathhouse & Saunas, Lingerie, Panties
A visit to a new bookstore turns into a very fun experience. Oral, anal
Topics: Anal Sex, Crossdressing, Gloryhole, Bookstore, Oral & Blowjobs
Garbage man or reporter? Assumptions can be misleading.
Topics: Crossdressing, Fiction, Mystery & Crime
A story of a shy crossdresser guy gets forced by a hungry bear.
Topics: Crossdressing, Forced, Neighbour, Bear
Finding Mr. Goodbar. Looking for the perfect man to fulfill my fantasies was a long, hard journey.
Topics: Crossdressing, Bondage, Sex
A gang bang fantasy.
Topics: Anal Sex, Crossdressing, Chastity, Big Dick, Gangbang
The guy was a bad photographer and an even worse perv.
Topics: Crossdressing, Bondage, Sissy
Confused and horny I meet another guy in a kinky threesome. And then, I become me.
Topics: Crossdressing, Bondage, Threesome, Panties