Regular readers may sense an ongoing theme. Back around the end of January, I wrote about the fifty-five-year-old virgin. And, well, I have a confession about that entry: that guy was really fifty-seven. I said fifty-five because I figured it was one of those facts I should change slightly to provide even more anonymity, but even with the exact age, nobody could figure out who that guy was. If you're wondering why the accuracy is suddenly important, it's because I've decided to go on a scavenger hunt. That's right, readers, I have decided to collect (at least) one virgin of every age from fifty to fifty-nine, inclusive.
I know what you're saying: "Why not go for the forty-somethings? Or the thirty-somethings?" I do think that fifty-something guys are really hot, but I can't honestly say that I find them any hotter than forty-somethings (thirty-somethings are another matter: many of them are still entirely charming, but early thirty-somethings tend to do less for me, and the feeling appears to be decidedly mutual). In practical terms, though, the public sexual history of the last thirty or so years has meant that a guy who makes it to forty without giving up the ass is probably never going to be eager to give up the ass. Contrariwise, there are still plenty of guys in their fifties who haven't but want to. And I'm here for them.
You can well imagine the difficulties inherent in such a project. Presumably, there's some sort of award or acknowledgment that accompanies the fulfilment of the goal, which means that there's some sort of public or private certification board that will require documentation. Plus, there's that whole deal where it gets harder to get that last age. I reckon that fifty-four will be the hardest one to get, and I foresee verrrrrry specific craigslist ads:
Dom Top Seeks Fifty-Four-Year-Old Virgin for NSA (Montgomery County - 43)
Forty-three-year-old dominant, aggressive top, expert at opening untapped asses, seeks fifty-four-year-old aspiring submissive who's never been fucked. Prior penetration by sex toys or fingers (your own) is acceptable. You must be willing to kiss and travel. A variety of other activities may also be enjoyed, by mutual negotiation.
Complete stats including exact date of birth in first e-mail. Please be prepared to produce a passport or birth certificate as proof of age; unfortunately, I can no longer accept a driver's license. Discretion assured.
Anyway, I got fifty-two Thursday night, and it was entirely unexpected. I got home from choir practice at a bit before 10, intent on scrounging up some dinner and watching part of Pan's Labyrinth, but when I went to check my e-mail, there were three messages from the same guy in response to my craigslist ad from early this week. The guy seemed eager. He said he was slender and had no m2m experience but very much wanted to try. I sent him an e-mail and got a response very quickly. It turned out that he lived in my little town. I was a bit skeptical, so in my third e-mail, I gave him my cell number and told him to call me. He seemed nervous, so I figured it might take a while. I took the opportunity to go upstairs and shower. I was drying myself off when the phone rang.
We chatted somewhat matter of factly for a bit. I asked him what he'd done, and he said, "Nothing." He mentioned his fantasies and how long he'd been thinking of m2m, and I told him he needed to start somewhere and invited him over. He said he'd be over in less than half an hour, so I finished getting dressed and went downstairs and watched a little porn. When the doorbell rang, I let him in without my usual pounce. I offered him a drink, he said water would be good, and I invited him to sit on the sofa. After I got the water, I sat next to him, and we started to talk about his experience (or lack thereof). I rubbed the back of his neck a little, and then I played with one of his nipples. He told me that he'd posted an ad for the first time that day and that he'd gotten a lot of response, but that he liked my ad because I seemed to know what I wanted and because he'd long fantasized about submitting. In other words, he was anxious but didn't know how to proceed, and he wanted someone to show him the way and to take all the responsibility. Well, that would be me. I told him we should go upstairs.
Tony was cute: short, slender, very fit. He was also on the reserved and quiet side, but that works for me, too. After fondling his ass all the way up the stairs, I turned him toward me and kissed him while I cupped his ass. I pushed him down on the bed, climbed on top and started to kiss him again. He seemed not really into the kissing but still willing to go along, so I figured he'd warm to it. After a while, I told him to take off his shoes, and then I pulled off his turtleneck and started playing with his nipples. Here again, his body reacted, but he kept any moans to himself. His nipples, though small, did get nice and stiff, though, and I kept working them for a while.
After I helped him out of his pants, I pushed him towards my cock, and he went down on it. He swore up and down that it was his first time, but he was pretty good. I felt his teeth a little bit, but not very much. (I mentioned the teeth thing to him, but very casually, and in the context of telling him that he was doing a good job overall.) I only had him suck me for about five minutes before pulling him off my cock and on top of me for some more making out. He was a lot more into the kissing then, and that was a very good thing. I rolled him onto his side and slid my cock between his legs so that it rubbed up against his nuts and the bottom of his asscheeks. He'd told me that he'd fantasized about that, and he did seem to like it a lot. He was never very demonstrative, though, and he was still very tense. I put him on his back and asked him how he'd liked sucking my cock, and he just said, "It was a very different situation. I didn't not like it, though." I started to laugh, and he seemed a little put off, until I explained that I just thought it was funny because I'm used to guys being a little more excited about sucking my junk. He said, "It's my first time!" Fair enough.
I pushed him back towards my cock, but this time I pulled his body around so that I could play with his ass with one hand while the other tugged on a nip. He was obviously relaxing and getting more into it because the bj had gone from pretty good to very good, and his head was moving up and down with a lot more animation. So I pulled him around until his knees were straddling my head, took a moment to appreciate what was both a very fine and an untested ass, and dove in. (I'd checked to make sure it was very clean, of course.) He didn't miss a beat on the blowjob. I was impressed.
We stayed in that position for a good long while before I pulled him off my cock again. He seemed reluctant to leave it. I pulled his head towards mine to kiss him some more. It's always interesting to see whether a guy will kiss you after you've been rimming him, but he didn't seem to have a problem with it. I put him down on his stomach and reached for the lube. I had a pretty good idea from playing with and rimming his hole that even though he was a little guy (5'6, 135, I'd guess), I should be able to work enough fingers into him to make him able to take my cock. Still, I was determined to go very slowly. The first couple fingers went in quickly and easily, albeit with lots of lube. He was being very quiet. When I told him that I could feel his pulse in his prostate, he did allow that what I was doing felt pretty good. Another five minutes in, he told me that he was really enjoying the pressure, and when I told him I had four fingers in him, he seemed incredulous.
I guess he was in something of a world of his own. Not only did he not know how many fingers I had in him, but after I was pretty loud and obvious about going over to the bedside table, ripping open the condom wrapper, and rolling the condom on, he asked me whether I had it on when he felt my cock against his ass. I assured him that I did. I suppose that a virgin ass is one of the few situations in which you could consider fucking bare, but I wouldn't consider it. I believed him, but why take chances? The idea of a bare fuck is not really any more appealing to me than a condomed fuck, anyway.
At first I just had the length of my (thoroughly gloved) cock lodged alternately in his crack and under his nuts, but then I got to the opening. I'd opened him well, but he asked me to go slowly, and I'd intended to go slowly, anyway, so I went slowly. I was still not getting a lot of reaction from him, but that also meant I wasn't getting any negative reaction. This was clearly not a guy to get swept away by anything, but I was having a great time. As I worked my way into him, he finally seemed to relax. I suspect that it was finally surrendering to something that he'd really wanted but wasn't sure he could do that got him to that point. After a while, when I was about halfway in, he even allowed that he thought he liked what I was doing to him.
The angle wasn't working so well for me. I probably should have shoved a pillow under his crotch, but I didn't want to stop the process, so I just went with it for a few more minutes and then pulled out and turned him onto his back. I put his feet against my shoulders, applied some more lube, and pushed back into him. I worked the angle to bump up against his prostate, and he liked that a lot for a few minutes but then said that it was getting a little uncomfortable.
So I pulled out again, got on my back, and told him to straddle me. He did, on his knees, and took about half of me inside again. I was lightly playing with his nipples, and he was bouncing just a bit. I grabbed his legs and unfolded them to get a better penetration, and he writhed a bit. Then I told him to give me his hands, and I held them and lowered him back into the X position, which got him downright excited. After a while of that, I pulled him back up, and he bounced up and down, while I played with his nipples some more. He started to go on about how deep I was in him and how much he liked it. That was fun.
We'd been playing for a long time, and I'd been fucking him for a less but still long time when I pulled him off me. It was great, but I was pretty tired, and I knew I wouldn't cum that way. I lay next to him and kissed him some and played with his cock some. He said he didn't know why he wasn't hard, and I explained it to him. I went down on him a little bit, mostly because his cock wasn't that big, so it's the sort that's fun for me to suck on, and then I kissed him some more while I jerked myself off. I put his hand back on my cock just before I went off. Impressive distance and volume.
We both lay there, on our backs with my left arm pinned under his head, and we talked for a while. I was surprised that he hadn't jumped up and run out, but I wasn't complaining. After some time, he said, "So, what's the plan?" I explained to him that I don't plan things out all that carefully, and then it became clear that he wanted to be fucked again. I was exhausted, though, and I told him that if he wanted that, he'd have to sleep over. It was well past midnight, and I had to be up for work early the next morning, and I hadn't had much sleep in, well, forever. Anyway, I'm past the point where I feel like I have to apologize for or explain any time when I'm only good for one fuck. I'd fucked him for a really long time. He said that he wanted to try doggy style and bent over the bed. I told him he was welcome to come back or wait for the morning. He said he'd come back.
I decided not to tell him that he probably wouldn't. I just told him that a lot of guys freak out after their first fuck and that he should go easy on himself. He said he was pretty sure that he was okay with it. He got dressed and left. I sent him an email, and I got a response back almost right away thanking me for being a good teacher and saying that he'd liked the evening's events and that he was ok with everything.
It would be cool, of course, to have a local bottom. And I'd thought that if he'd stayed sane for a few more meetings, he might be worth introducing to Christopher for possible dating. But the next morning when I went to respond to his most recent e-mail, my response bounced, and the message said that the Yahoo account (which he'd mentioned he'd set up specifically to begin looking for guys) had been deleted. Clearly, he'd freaked after all.
Oh well. At least I had a terrific time while it was happening. I just hope that fifty-one and fifty-eight will be as much fun.