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A Sissy Boy’s Fantasy Come True  

gymrat1974 49F  
1056 posts
6/14/2020 11:40 pm
A Sissy Boy’s Fantasy Come True


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 look in the bag on the bed. Inside was a purple negligee and black thigh highs. I watched as you went from thinking I was going to wear it for you to realizing you were going to wear it tonight for me. Your pretty cheeks turned crimson. You tried to resist, but a deal was a deal. Slowly, you removed your clothing. And I helped you as you pulled the negligee down over your head and pulled the stockings up your legs. You stood and the purple lace barely covered your penis. Your pretty little ass cheeks, still bruised from your last spanking visible, too.
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...

I directed you to the middle of the room. You stood there with your head bowed. No one made a sound. There was no laughter. It was more wide eyed shock. I then suggested that you ask your friends if any one needed a drink refreshed and to be a good little hostess. You looked adorable as you bent and poured and cleared away the rest of the table. I have to admit I was thoroughly aroused. Your body always turns me on, regardless of your state of dress or undress.

Finally, I called you back to the middle of the room. I made you twirl. The lace raised above your hips, your beautiful cock on full display. I sank to my knees to harden you. It belongs to me, but I don’t mind letting others see it. I licked the underside of your shaft and drew you into my mouth. You were hard in an instant, though making you cum took extra coaxing. My hands squeezed your nut sack as I crooned and slurped and coaxed you along. Finally, you came, and I swallowed most of it except for the bit I left glistening on lips. I rose to my feet, kissed you with your semen on my lips, and pushed you down to your knees. The last surprise of the night was hidden beneath my sundress. I lifted it to bear my 9 inch strap on. Suck it, I ordered.

You started slowly, kissing the head. Licking the shaft, stroking it with your hands. Finally, you took it in, inch by inch until you had at least half of it in your mouth. I grabbed you by your head and forced you to take more of it like you would take it in your ass. I could see the crimson return to your cheeks as everyone in the room could hear my words. “That’s right! Take it! Take my cock. Take it like it’s inside that pretty little ass of yours!” I told you to satisfy my cock or I would bend you over the armchair. You gagged and sputtered, but you took more to where I could see almost none of it left. Such a good little sissy boy you are. Finally, I removed the strap on, attached it to you, and sat you down on the couch. I straddled you right there and sank down on it. I quickly came from the excitement of the night and from the size of that hard phallis filling my wet pussy.

It was late by this time, and everyone was tired and still in a bit of shock. They had never witnessed anything like this from us before. They chose to stay and crash out on the couches. And you and I withdrew to the bedroom. The next morning, no one said a word about the nights events. Maybe it was some strange dream each one thought. But you knew what happened. It was all in all a sissy boy’s<b> fantasy </font></b>come true.

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