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I stuffed his underwear inside his mouth as a gag and tied the pillow case around so he couldn't spit it out. This is about when he woke up. Infuriate... (as he said he was going to be) I lay on top of him with my dick between his ass cheeks with lube running down and dripping off my tip into his crack. I had my legs hitched over his knees so he couldn't kick. I leaned over him and said "who's the cowboy now? Looks like I'm about to saddle up!" Then pushed my tip into his asshole he flailed. Do I dare go through with this? I was certainly out of my comfort zone, but then I felt this same way the first time I had sex with another man during my first swinging experience. The path was uncertain then but it worked out wonderfully for me. This path was just as uncertain and it could bring disaster or riches. I chose the riches and agreed to go back to his hotel.I asked him where he was staying and he gave me the address and room number to a very nice hotel (my company had booked it for. More

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