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Another Take on a sissy boy’s fantasy  

gymrat1974 49F  
1056 posts
6/14/2020 11:42 pm
Another Take on a sissy boy’s fantasy


I asked if I could play on poker night. It was normally the one time I gave you complete freedom to be with your friends, but I was feeling mischievous and playful and I wanted in. You were slightly nervous by the look in my eye, but your friends were ok with my staying to play.
We began playing by the usual terms but as the night wore on and the weed and cigar smoke filled the room, everyone became more relaxed. I’d been doing ok. I won a hand here and there. I was pretty confident in my poker playing abilities. And then I suggested a change in terms. When we got down to the last game, I said I would strip completely naked if I lost, and if anyone else lost, he would take a dare I had yet to determine. I heard you groan. It wasn’t so much that I would be naked in front of your friends. It was more the idea that you didn’t have a clue what sort of nonsense I had up my sleeve. Your friends decided it was worth the risk.
The final hand of the night had finally been dealt. I know someone was going to do something naughty, but it wasn’t going to be me. I had a royal flush. I looked around the room at all your friends and wondered who had become my toy for the night. Poor soul that you were, it was you.
I think you thought you were going to have to strip, as I would have, but it was about to be much worse. I led you into the bedroom and told you to put on the panties and garters you had on the day before. Of course, I knew you’d been wearing them. They smelled like you. I watched as realization hit you. “That’s right,” I said. “If you want to dress like a girl, you can go play with the men.” Your pretty cheeks turned crimson. You tried to resist, but a deal was a deal. Slowly, you removed your clothing, and then you put on the aforementioned panties and garters. I must admit, you loved lovely in them. Your beautiful backside filled them out, and your penis bulged from under the pale pink lace.

I felt only a moment of guilt for my underhandedness as I led you to the door. After all, anyone could have lost tonight. It didn’t have to be you. Nevertheless, I pulled your face down for one brief kiss, swung the door wide, and pushed you back into the living room where your buddies were still seated at the table.

You stumbled into the room and nearly fell at the feet of one of the men. I left the door slightly ajar but stayed in the bedroom. I wasn’t sure if I was ready to watch you be devoured by another man, much less three of them. They seemed to know what to do, however. They began to tease you with words at first. I could hear them call you a sissy boy and a pretty little girl. And then they complimented you on your choice of attire. And then one of them ordered you to come to him. I returned to the door way to watch. He had you turn around for him in a slow circle. Your beautiful ass covered by my panties. He slapped you a couple times. The beautiful sound echoed throughout our living room. The friend to your left began undoing the garters. I could see you helplessly stand there as the fabric fell to the floor. And then he slid the panties down. You were suddenly naked. I was embarrassed for you, yet somehow my pussy quivered and I could feel my wetness increasing. I could see them touching you. One hand was on your cock as the first man continued to spank you. Indeed, he pulled you down across his lap and spread your legs so that your balls were exposed and began to spank you in earnest, all the while, calling you a bad girl. You began to moan as his hand continued to play across your backside. The two other gentlemen appeared to be growing aroused. I could see them adjusting the crotch of their jeans. They each took turns coming and standing before you as the first one continued his spanking. You took each of their cocks in your mouth like a pro. You did for them what I always do for you. Finally, after the two were spent, the first guy lifted you from his lap and turned you around. He bent you over the table where the poker game had been played just an hour before. He stroked himself to hardness, spit on his hand, wet his cock, and inserted it with ease into your little asshole. Your cheeks were still red from your spanking. I could hear your whimpers as he thrust in and out of you, and I had to shut the door. I was embarrassed at all that I had seen, but I needed to cum, too. I lay across our bed, turned on my hitachi, and could hear your collective shouts of satisfaction as pleasure overtook my own pussy.

A sissy boy’s<b> fantasy </font></b>was complete tonight. And I didn’t realize how much it fit in with some fantasies of my own.

Edited with your ending:

After the men were finished with you and I had cum several times, I entered the living room. You were still standing naked at the table, cum dripping from your ass and down your chin. I leaned down and whispered in your ear that I hoped you enjoyed it. There would be plenty more where this came from.

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