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He was tight but with both of them fucking him he was starting to loosen up and get used to it. I continued till my fingers glided in and out effortlessly and said, “I think you’re ready now.” “Yeah, I can’t wait, put it in me.” He almost begged. I had him get up for a moment. Then I placed a small thick pillow in the middle of the bed and had him lie back with it under his hips and as he pulled his legs all the way back till his knees were almost in his face. Grabbing a condom I rolled it onto my cock and coated it and his hole generously with lube. On seeing his readiness I knew it was time for me to slip into something more comfortable, HIM! I carefully lined up my organ with his most inviting anus glistening with lube and told him to take deep breaths and slowly let them out. Each time he exhaled his muscles relaxed and I entered a little deeper. Suddenly, and with an ease that took us both by surprise, my head popped through. Stretching out above him with his ankles on my. Attending tonight's Hallowe'en party was a half-hearted attempt to get out and see the local nightlife. He'd noticed, over the last few years, a subtle trend toward a 'trashy and flashy' look in fashion, and had begun to have hopes of finding a lover who shared his tastes. He had debated for hours what to wear to the party, balancing the requirements for a costume against his desire to "come out" in something kinky. In the end, he settled on renting a Spanish toreador outfit worn with his own black rubber knickers, and a simple domino mask. It took all his courage to wear the pants, too. But as he pulled the stretchy, shiny latex over his legs, he realized it didn't matter what people thought, tonight was Hallowe'en! Tonight was the one night he could wear anything at all without fear of ridicule or outcry. He revelled in the tight, smooth feel of the rubber jeans. To hell with it, he thought, I'm going to enjoy myself tonight! At the party, which was hosted by a local radio.
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