69 Votes
Dad and me
dad finds me in her room wearing her panties and bra. Oh fuck!
Topics: Incest, Sissy, Dad & Son, Lingerie, Panties, Fucking
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dad finds me in her room wearing her panties and bra. Oh fuck!
Topics: Incest, Sissy, Dad & Son, Lingerie, Panties, Fucking
Another Halloween is here! Maybe this year I'll catch my first man!
Topics: Crossdressing, Oral & Blowjobs, Lingerie, Halloween
A hotel get-together turns kinky with a double ball gag. Then the Master comes later.
Topics: Seduction, Master & Slave
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
He was great. He followed all my requests. A dream come true.
Topics: Crossdressing, Bondage, Sex, Fucking, Love
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
My gay lover left me but not before he turned me over to a gay Dom Master. I guess I should have been more careful of what I asked for.
Topics: Bondage, Sissy, Cash Master
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
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
'Daddy' shaved me in the shower. While the water was pouring over us, he put me in a matching set of rubbery vintage Playtex bra and open bottom girdle panties.
Topics: Crossdressing, Shower, Daddy, Rubber, Panties
She works in advertising. She is HOT! I waited for a long time to even say hello. I've never been with a trans girl. Does she still have a dick? I don't know. But I want to find out!
Topics: Transgender, Oral & Blowjobs, Hookups & Dates
I've been in the closet all my life. Finally, I have a chance to try out being a sissy girl for a real man
Topics: Crossdressing, Sissy, Domination
Every day I awake from a dream of being used as a girl whore. I can't stop it. I'm in trouble!
Topics: Anal Sex, Crossdressing, Bondage, Sissy, Master & Slave, Fucking
They told me the Karaoke bar it was in a gay part of the city. Now I go back frequently.
Topics: Bathroom, Oral & Blowjobs
The gay date I'd love to experience. I've had a few gay experiences, but someday a man will make me his little bitch. I'd love that!
Topics: Crossdressing, First Time, Oral & Blowjobs, Domination, Submission, Panties
I finally let him seduce me. I agree to meet him. He has been flirting and making promises. Then at the last minute, he tells me I'm going to dress like a woman tonight.
Topics: Crossdressing, Sissy, Oral & Blowjobs, Halloween
Remembering sexy guys in sexy jockstraps got me thinking about having my first gay date.
Topics: Shower, Jock, Jockstraps
A shy, submissive guy hits me up to dress like his wife and Domme him. I actually liked it more than I thought I would!
Topics: Crossdressing, Bondage, Domination, Submission
After drinking with some seedy guys in a dive bar, I get lost and end up at their front door.
Topics: Anal Sex, Bondage, Daddy, Drugs, Drunk, Domination, Fucking
My cousin has been single forever. I always wondered how he manages it. I've been with girls. I even got a little gay for a while. But that is me. Mike is a whole different story.
Topics: Anal Sex, Bondage, Boyfriends
I forgot and wore some panties to my check-up. The doc was surprised. But he responded differently than I expected.
Topics: Crossdressing, Doctor, Medical, Lingerie, Panties
Joe was always pretty much a Dom. But he seemed to figure out I'd do pretty much anything to suck him off. So he just keeps pushing. Now I have to go out and buy some items he requested. And that is a whole other story!
Topics: Crossdressing, Rough Sex, Spanking, Oral & Blowjobs, Lingerie, Panties, Fucking
My wife installed one of those nanny cams. She wanted to see what the dog was doing when we were at work. She didn't tell me. She started watching me dress in her underclothes and tie myself up like a kidnap victim, jerking off. Not sure what to do, she asked a friend to watch the videos. He knew just what to do with me.
Topics: Crossdressing, Bondage, Married
The rumors that I'd sucked off a guy from work got around. I guess I seemed like an easy mark. A boss from work took me to lunch. He had the Grilled roast beef. I got my lunch directly from him.
Topics: Rimming, Co-worker, Oral & Blowjobs, Domination, Boss
I reluctantly go to a party with my girlfriend. She gets drunk and I get gay.
Topics: Bondage, First Time, Oral & Blowjobs
Envious of the girls always getting to wear those cute little bras and panties.
Topics: Crossdressing, Sissy, Lingerie
I know she is a trans or whatever. But she is so nice. I finally agree to stop over for a drink and some pie. Later she had me sucking her straw and eating her ass like a pie.
Topics: Rimming, Neighbour, Transgender, Seduction, Oral & Blowjobs, Submission