19 Votes
Sissy photo shoot peril
The guy was a bad photographer and an even worse perv.
Topics: Crossdressing, Bondage, Sissy
GayDemon's gay porn library: in this story category you can find erotic stories with crossdressers and crossdressings.
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
I turned 18 yo. I was always intrigued by what puberty did to my body. It was summertime parents worked 6 days a week. Leaving me to stay home and do mischievously things.
Topics: Latin Men, Anal Sex, Crossdressing, Dildo, Interracial, Sissy, Twink, Nudity
After meeting Carl he agreed to fulfill my crazy fantasies. What fantasies would he fulfill for you?
Topics: Crossdressing, Bondage, Oral & Blowjobs, Throat Fucking
Someone recognized me from the post in GayDemon! Maybe I was hoping that would happen?
Topics: Bondage, Forced, Sissy, Blackmail, Oral & Blowjobs, Lingerie, Panties
Late in life I finally explored the dark side. And there is no going back.
Topics: Crossdressing, Bondage, Sex, Panties
I moaned running my hands over my body thinking of all the men I had been with over the weekend and started stroking myself to the verge of orgasm, but I stopped myself because I wanted to share my orgasm with a man any man.
Topics: Anal Sex, Crossdressing, Big Dick, Fisting, Sissy, Lingerie
Getting slutty and hot a gay club for the first time
Topics: Crossdressing, Public Sex, Poppers, Rimming, Sweat
Ryan buys me sexy underwear and intoxicates me with his masculine scent before sucking my little nub into the most glorious orgasm I had experienced.
Topics: Crossdressing, Relationship, Underwear, Oral & Blowjobs
Dressed to Kill! First date with stranger and ready for seduction!
Topics: Crossdressing, Transformation, Lingerie
Hetero guy with kinky man to man fantasies
Topics: Crossdressing
I turned 18 yo and graduated out of high school. I decided to move out on my own without a roommate. I got great job to pay bills.
Topics: Crossdressing, Sissy, Hypnotized
Driving long distances can be lonely. Here's a tale of a driver picking up a little friend on a dark highway and teaching him how to be a good cock sucking sissy. Gas, Grass or Ass, nobody rides for free.
Topics: Anal Sex, Crossdressing, Forced, Daddy, Sissy, Hitchhiking, Virgin, Homeless, Slave Training, Fucking
Another Halloween is here! Maybe this year I'll catch my first man!
Topics: Crossdressing, Oral & Blowjobs, Lingerie, Halloween
I became a sissy slut in high school and I didn't mind the guys using me for sex. After graduating a bully named Troy decided he wanted my ass. I knew I had to put out.
Topics: Anal Sex, Crossdressing, Rough Sex, Oral & Blowjobs
A 2006 solo trip to European is a fulfillment of a lifelong dream
Topics: Crossdressing, Travel
I played for a long time in her clothes. I even took some pictures of me dressed up pretty. Now I have men calling me all the time. What should I do? Does dressing make me gay? I do dream of sucking a big fat cock a lot. Maybe I'll answer one of the guys.
Topics: Crossdressing, Bondage, Sissy, Oral & Blowjobs
Jim noticed I was wearing nylons and a bra. He used my embarrassment to his advantage.
Topics: Crossdressing, Forced, Oral & Blowjobs, Lingerie
What happens after the corporate holiday party and events leading up to an unusually interesting Brunch with Chris' Boss
Topics: Crossdressing, Cum Swapping, Sissy, Oral & Blowjobs, Nipple Play, Boyfriends
He was great. He followed all my requests. A dream come true.
Topics: Crossdressing, Bondage, Sex, Fucking, Love
I had gotten dressed very sexy and slutty one night being completely hairless permanently except for my eyebrows eyelashes and long hair on my head.
Topics: Crossdressing, Daddy, Homeless, True Story
I started wearing moms underclothes when I was younger. They were always laying around in her bedroom and in the laundry. But later I discovered he was leaving them around for me to find. He was tricking me into becoming a sissy crossdresser for him.
Topics: Crossdressing, Oral & Blowjobs, Lingerie
I dressed like a girl for prom. My friend Jeff and I didn't have proper girl dates. It was sort of a joke and a few of the other boys were doing it. And Jeff's dad seemed to like me a lot.
Topics: Crossdressing, Daddy, Sissy, Drunk, Love
Decker has found out his nemesis, Fitch, another closeted jock, has been hooking up with a male escort/cam boy. Now he intends to get what he wants from the gorgeous jock by blackmailing him.
Topics: Muscle, Crossdressing, College, Jock, Blackmail, Lingerie, Bodybuilder
My life that i want
Topics: Black Men, Slut, Interracial, Drugs, Sissy
She told her friends I wanted to wear her underwear and be tied up when we had sex. It was a weak moment for me. I shouldn't have asked her. I was young and didn't know any better. She didn't appreciate my wishes at all. That was it for her, and most any other chance I may have had with a girl. But, she handed me off to someone who did appreciate my fantasy. For better or worse!
Topics: Anal Sex, Crossdressing, Lingerie, Panties, Fucking
I wore a girl's dress as a joke to a Halloween party. It was all in fun. Wives and girlfriends were there. But after that, I got a few uncomfortable calls and texts from a few of the men who saw me.
Topics: Crossdressing, Lingerie, Halloween
I woke up in his bedroom, wearing his wife's wedding lingerie. I'm on my knees with his cock in my face. What now?
Topics: Crossdressing, Bondage, Oral & Blowjobs
A young drifter in Palm Springs is taken in and trained as a sissy, a slut, a slave, and a boi-whore by two older men and their friends.
Topics: Piss, Anal Sex, Bondage, Dildo, Sissy, Domination, Control, Fucking, Feminization
My straight buddy and I visit a gay bar, where we discover our own inner selves, and the truth about each other
Topics: Crossdressing, Sissy, Twink, Oral & Blowjobs, Shaved