Halloween party

by BillyBoy

2 Dec 2021 3564 readers Score 7.8 (14 votes) PDF Mobi ePub Txt


The seduction

I was in the closet. The gay closet. The crossdressing closet. All of the closets. I'm always lonely, bored, and horny. I chat a lot. The internet lets you be anyone. George likes me. He lives 2 hours away. It took us several months to share real pictures of ourselves. He is 50 ish. I'm 46. He tells me how cute and pretty I am. He knows I like to think of myself as a sissy. I wear panties and a bra for him in some of the photos I post. I watch him jerk off to the photos while he talks to me on Skype. He is stern and masculine. I told him I like that. I beg him to call me sissy names and warn me about what he will do to me when we meet. He calls me his cum dump and sissy whore. He tells me he will fuck my brains out while I'm strapped over a table like a kidnapped sex slave. Whips, chains, gags, dildos, spanking paddles, and all. He is very verbal and makes me really hard. I rub my cock in the silky panties and I pinch my bra-covered nipples when I jerk off. It is fun.

It's time for a meet-up, he tells me. Just a drink in a local bar. We can meet and decide if we want anything else at a later time. He says I should wear his favorite sexy underwear for him. I can put on a girdle, garters, stockings, and a corset. I can put on a shirt and pants over it all. It will be casual. I've told him I have never gone out in ladies' undies. This will be a good time to give it a go. It will be safe. It will be fun.

The setup

Just before I leave he calls and tells me to bring the leather collar I have. I should wear it in the bar. No one will notice, he tells me. I find it and off I go. 

He surprises me. He is shorter and a little chubbier than his photos. But that is to be expected, I suppose. We only sit for a minute. He seems happy with who I am. Tall, skinny, and pretty. He wants me to go to the bathroom with him. I'm getting nervous, of course. In the stall, he grabs me and tries kissing me. He finds the collar in my front pants pocket. He straps it around my neck while kissing me. I like his hands on me. I let him buckle the collar. I let him manhandle and kiss me. My shirt comes off.  My pants are unzipped and drop down to my ankles. He kisses me and feels me up like a drunk prom date. I like it. I'm getting hard. So is he. 

"Let me do this."

He reaches for my pants. He helps me step out of them. My belt slips out of the pants. He pulls my arms back behind me. He wraps the belt twice around my elbows. It pulls tight. I'm harnessed like an animal. More kissing and groping. He keeps talking dirty.

"I'm going to fuck you like the whore you are."

So far, I'm loving all of this. Pretty soon he will have had his fun, we will both have jerked off, and I can go home.

Out of his pocket comes a ball gag. I've never seen one for real. But I did get to see this one first hand. Well, first mouth. It tasted like rubber. Like a condom. He strapped it in really tight. Too tight. Then he clipped a leash to my collar and led me out of the stall. With my shirt and pants under his arm, me in just the sexy ladies' underwear, we walked out of the bathroom right back into the bar. Some of the patrons began to clap and whistle. Looking around I noticed no women in the place. He walked me around like a prize for a few minutes. I was gasping for breath, drooling from my tightly gagged mouth. Some of the men grabbed for my ass. Everyone was laughing and having a good time at my expense. 

"Don't worry about that gag, sweetie. I'm sure he will have it out of there and replaced with something even better very, very soon. Hahaha!"

The fucking, coming soon..

by BillyBoy

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