Doubling Bets

I came up second longest and thickest, so I was picked as one of the house champions. Dennis, a news agency journalist, who was a good fuck buddy of mine, got highest honors, which pleased me; we’d taken turns with each other as top and bottom, and I enjoyed either position with him.

After Dennis and I had stripped down, I was pleased to see that the Thai was showing that he thought this was all a good idea. He was all smiles and winks and lustful looks. It should have been another signal for us when he didn’t seem to mind what was going on—but for all we knew, he hadn’t been clued in on the plan at that point yet—or, indeed, just didn’t understand English very well. We cleared a space in the center of the room and someone found a cot mattress from somewhere in the depths of Cowboy’s back establishment, and we had our arena.

Dennis, the Thai, and I engaged in a good half hour of three-way feeling and kissing, and stroking, cocksucking, and greasing ourselves up lavishly with lube to get us all in the mood and to get Dennis and me lengthened and thickened to the point where we assumed our bet was well covered. In time, though, I found myself on my back on the mattress and the Thai straddling my hips with his thighs. And then he was settling on my cock. Dennis had a hand under there, fingers wrapped around my cock and rotating my dick head in what felt like a tight ass opening. But then the Thai arched his back above me, settled his pelvis, and he was coming down on my cock, swallowing it with his ass, the muscles of his canal walls undulating along the sides of my cock as he settled down into my lap. He was driving me crazy down there, and I managed to tell Dennis between gasps what was happening. The boxer had magic ass muscles and was going to make me cum and start going flaccid before Dennis got his cock into position.