Doubling Bets

I should have known that the sneaky Dutchman had all the angles figured when he suckered us into betting against a myth in the Men Only back room at Cowboy's Bar in Bangkok's Patpong district. He waited until the third revolution of the happy hour clock—when we were all soused and sluggish—and then entered with a boy-built Thai. I recognized the Thai immediately as a champion bantam-weight kick boxer from the arena over by Lumpini Park. Knowing the Thai, I figured he probably was a lot closer to thirty than he was to twenty, but he wasn't much over five feet tall and was skinny as a rail. All corded sinew, though, and I'd seen him put opponents in the hospital over in the ring. He still had all of his facial features where they belonged and was quite well turned out in looks, so it's obvious he'd been able to defend himself successfully.

Those of us holding up the bar couldn't isolate—even when we revisited the issue several days later—who exactly brought up the question of whether the myth that two guys could fuck another one in the ass simultaneously was fact or fiction. But it must have been the Dutchman. He must have had it all planned before he brought the Thai kick boxer into Cowboy's.

It came down to the boys at the bar against the Dutchman. We all said it was a myth, and he asked us if we wanted to take up bets on that. Suckers that we were, we did. We even thought we'd put one over on him, when one of us had the presence of mind to stipulate that we could pick the cocks that would be buried and, that stipulated, took the time and effort to do some comparing and measuring. The Dutchman even let us check out the Thai's hole on a surface inspection, and led us into doubling the stakes when we saw there was nothing especially slack about the Thai's backdoor.

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.

The Thai was grinning above me, going for my nipples with his strong fingers, trying to bring me past the brink.

Forewarned, however, Dennis pushed the Thai's chest down toward mine, tipping his hips up, and I felt the giant mushroom head of Dennis's cock at the base of my dick where it was encased by the Thai's asshole. Dennis was grunting mightily from the effort to enter the Thai, and the Thai, his face very close to mine, was registering pain in his eyes and panting with exertion himself.

But slowly, ever so slowly, Dennis's cock was sliding in and I felt its warm, hard, yet pliable skin pushing in on the underside of my own cock. All three of us were straining now from the effort. But somehow the Thai took us both. He reached a point where we were both beyond the entry-level of muscles in his ass, and I could see the transition in his eyes from overriding pain and some sense of uncertainty to triumph and "ride me hard" lust.

We'd lost the bet to the Dutchman, who was showing no pain or exertion at all as he walked around the circle of oglers, pulling in cash. But, without the exchange of audible signals, Dennis and I managed to agree to get a good ride for the money. We started pumping the Thai in counter pistoning that produced arousing friction I've never felt in a corn-hole encounter since. And good sport and magnificently conditioned athlete that he was, the Thai went with us and we all bucked to near-simultaneous ejaculations.

So, now, whenever I hear anyone pooh, pooh the idea that double penetration can even be done, I just smile a little smile and remember how I got more value in losing a bet in the backroom of Cowboy's bar than I'd have gotten if I'd won.