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As she inched closer and closer to my hardening cock, she would pull her hand away to tease me. It was fantastic!! Looking back on it now, everyone at the table knew what was going on and were polite enough not to say anything. 6:00 didn’t get there fast enough. We made sure, as everyone exited the restaurant, that chaperones saw us give each other a kiss and head out in different directions with our friends. No idea if it actually worked or not, but we thought the show would throw everyone off just enough. I walked along the strip with a few friends; most of them knew the plan. They stopped to talk with a group of girls then popped into an arcade at about 6:10. At precisely 6:15, I looked at the exit to make sure the coast was clear, told my buddies to cover for me, and headed for the door. As I walked through the exit and made a right turn toward the hotel, one of the chaperones, the father of a close friend of mine stopped me. He said, “Where the hell are you going?” I’m sure I. He told me that he was experienced in the use of sissy males, and that he knew what he wanted. This was nice to hear as im submissive and i like a man that will take control. We decided on a hotel meet. I arrived early and checked in. I did my makeup, and my nails, got dressed in a tight red dress with black heels and awaited his arrival. It wasnt long before there was a knock at the door and i let him in. We had agreed via email that neither one of us was one for small talk, and he wasted no time. He pulled out a gimp mask from his holdall and put it on me, then reached in once again and pulled out a cock cage. I liked the idea of this as i had never used one before, he put it on me and told me to remove my dress and go and lie on the bed, I was beginning to realise i was in for a fun night. He then told me to put my arms up above my head and keep them there. I did so while he undressed at the end of the bed while i watched. he laid next to me and grabbed my balls and squeezed.
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