I've been exploring my bi side for some 13 years now, but until this summer, all my encounters were pretty much limited to mutual stroking, cock-to-cock play, and occasional oral sex. Then, last May I started hanging out with Dave, a retired dentist with whom I'd connected online. At age 66, Dave shared many of my interests, and nude hikes around his secluded property near Delafield and long, luxurious soaks in the hot tub on his big redwood deck quickly turned to sex play -- as I more or less expected they would. Being a newbie to guy-on-guy forms of play, Dave was very motivated and eager to try new things, and over the course of several weeks he became increasingly inquisitive. One evening last August, while we were enjoying margaritas out on his rear deck, Dave rather matter-of- factly asked if I'd consider letting him fuck me -- bareback! Maybe it was the tequila talking, or maybe just that I wanted to oblige a guy I felt close to, but for reasons still unclear to me, I agreed to do what he asked. Moments later, Dave and I were bounding naked up the up the stairs to his bedroom to attempt something I swore I'd never, never, ever do. Well, for the next hour-and-a-quarter, Dave tried unsuccessfully to enter me from a half-dozen different positions; doggy style, spoons, missionary, standing -- but even with an ocean of libricant, he never managed to get more than a couple of inches of his cock inside me before intense pain made me beg him to stop. Frustrated, Dave finally gave up. I could see he was disappointed, so I promised to let him try again the following weekend. Never one to admit failure, I consulted a more experienced bi friend who told me in explicit detail how Dave should use his fingers ready me for penetration. He suggested using Astroglide silicone lube inside and outside my opening , and taking plenty of time to stretch my opening. He told me the best position for first time anal would be with Dave on his back, and me straddling him in the "cowboy" position . In that way, he said, I'd be more relaxed because I could effectively control the depth and speed of penetration. Well, the next time Dave and I were together, I followed my friend's instructions, and to my amazement, Dave's cock went right in with little effort and only minimal discomfort. Admittedly, it still wasn't an entirely pleasant experience for me. What I remember most was an uncomfortable feeling of pressure and fullness. But as I began moving up and down on Dave's cock, I could see and hear that he was in total bliss . . . so I kept going. Okay, for what it's worth, there was a certain thrill that came with looking into Dave's eyes and seeing intense pleasure reflected there. There was also an odd sense of satisfaction when I felt his penis twitch and throb as he came deep inside me. Does that make me gay? I don't think so. It only makes me open to sharing a sexual adventure with a like-minded friend. Would I do it again? Well, as a matter of fact, I did one more time after that. We used different positions that second time, but still wasn't particularly pleasant, and I'm not really eager to attempt a repeat performance. But, then again, if there's one thing experience has taught me, it's to never say never again, particularly where matters of sex are concerned.
