One of the trickiest parts about pursuing men is knowing how long to keep up the pursuit. Ideally, of course, men will pursue you rather than the other way around, but we don't (or at least I don't) live in an ideal world, so while being seen as the pursuer frequently kills your chances, and while neglect works magnificently with lots of guys, most guys require at least some form of encouragement.
A case in point: Anthony, a late-thirties bearish guy who chatted me up on (I'm pretty sure) gay.com. He's just moved to the area to take a new job. He has a partner of twelve years who is still living in Ohio, and whose date of relocation to Maryland is indefinite. Anthony and his partner don't have an explicitly open relationship, but Anthony is horny. Those are the facts; here is the conjecture: Anthony worries that the separation may become permanent; Anthony has not had sex outside the relationship frequently or recently; Anthony is very lonely but ambivalent about cheating on his man. Anyway, he chatted me up, we exchanged some pictures (his mostly just showed his backside, but it was the sort of backside that I could easily get excited about), and there followed a series of email exchanges that never came to anything. First I suggested a date and didn't hear back, but then a week later he wrote to say that he hoped he hadn't missed his chance. Then last week, he suggested a date, and we made arrangements, and he had to cancel at the last minute, citing an unexpected development at work that would keep him at the office very late. But, again, he apologized and said that he hoped we could reschedule.
At that point, I was tempted to send him a very nice email saying that my sense was that while he was excited about the prospect of my fucking him, he was worried about cheating on his partner. The notional email would have continued to say that I would certainly have enjoyed playing with him but that I find it sweet when a guy wants to remain faithful, and that I have no interest in pushing anyone into doing anything that he isn't sure he wants to do and might regret later. So, I would have wound up, there were no hard feelings, but it would be best just to let the matter drop.
But I didn't send (or even write) that email. Instead, I just wrote that I was sorry he couldn't make it and that he should let me know if he would be available again in the near future. The thing is, I do find it sweet when a guy wants to remain faithful to his partner, and I don't want to push anyone into doing anything that he isn't sure he wants to do and might regret later. But the other thing is, sweet guys are hot, and I reckoned that he really did want to play and just needed a little more time to come to grips with the idea, so I gave him that opportunity.
So I got another email early this week, and I knew b&c was going to New Jersey to visit his mother for a couple of days, so I told Anthony that I was free late on Thursday evening. He warned me that his townhouse was unfurnished except for an air mattress, but I thought that sounded kind of hot (it's just not that hard to excite me, you know?), so we made arrangements: I'd call him when I was close to his place, then he'd leave the door unlocked and the light on in the bathroom, I'd come in and take a shower, and he'd be waiting for me on the air mattress, naked and on his stomach.
I had to play late on Thursday because it was also back to school night at YFU's middle school, a fact I mention only so that I can also mention that one of the Physical Education teachers looks like a cross between a Samurai and an Aztec warrior. All the male PE teachers are eye candy, but he stood out. After lengthy consideration, I've decided not to stalk him. I'm sure that he's bitterly disappointed, but my research indicates that he also coaches a high school varsity football team, so at least he can console himself with plenty of cold showers in the company of linebackers.
Anyway, by the time I got to Anthony's house, I was pretty worked up, so when I'd finished showering and found him lying, ass up, on the air mattress, we got right into it. By which, of course, I mean that I started kissing him and playing with his nipples. He had nice lips and sensitive nips, and it was pretty good, but there was something not quite right in his manner. He'd be all into it, and then I'd toss in a slight variation, and then I'd come back to kissing him, and there'd be a reluctance, but then the reluctance would vanish. And, really, I didn't think too much about it because I was horny, and he had a fun body to play with. I'm generally not all that visually attractive to bears, but there's no denying that they're cuddly. Besides, after a while, he decided that he wanted to go down on me, and he was really good at it, so I just stopped thinking. He lay on the air mattress so that his shoulders were just under my thighs and buried my cock in his mouth, and everything was coming up roses.
I let him suck on me for a long time, but eventually I wanted to kiss him again and start playing with his ass, so I pulled him off my cock, got him beside me, and we started again with the intense cuddling and kissing. And I started fingering his ass and then I put him on his stomach and lay on top of him, kissing and licking his ears and the side of his neck and rubbing my cock in his ass crack. He seemed especially into that. I went back to kissing him, then I told him to go down on me again so I could eat his ass, and that was just a whole lotta fun, except that he'd occasionally get overwhelmed by the sensation and stop sucking my cock. But, hey, I was eating ass, so it was all good.
And it was all good when we went back to yet more making out. But then he turned away from me and tried to shove his ass back against my cock, so I turned him back to me, figuring I needed to get both of us ready first. I started in with a wet finger, and he handed me the lube, and then things started to get weird. I lubed a finger and stuck it into him, and suddenly he couldn't handle it, and, worse, when I went to kiss him, he turned away and said, "No." So I tried again with a couple of lubed fingers, and he tensed up entirely and said, "I can't. I think I'm done. I'm sorry."
There's something about a raging hard-on that gives me great equanimity. I didn't say anything, and I really only though, "Huh? Weird," and then I started to stroke myself. I had one arm around him, and the combination of that and the stroking felt really good, so I was kind of whatever, but he still seemed upset and apologized again, and I really didn't want to be a dick, so I said, "You don't do this much, do you?" "Um, it's been a while." "Yeah, I kind of figured that."
And that was pretty much all it took, a little bit of kindness and some mental space. I kept my arm around him, stroked myself absently, and didn't especially react, and a few seconds later, he kissed my cheek and sort of snuggled down into my arm, and I reached over and played with one of his nipples until it was hard, and he rubbed his beard against my chest, and I put my other arm around him, too, and we started kissing again.
And a couple of minutes later, he was on his stomach, and I was on top of him, with my cockhead up against his asshole, and he was asking me to go slow. I assured him that I'd go as slow as necessary, but, really, he opened up pretty quickly, and he really wasn't all that tight, though it was certainly a perfectly fuckable ass.
Before long, I was going at it pretty hard, and he was egging me on. He seemed to stay right on the edge between "it hurts" and "don't ever stop" for about ten minutes, and then he asked me if I was about to cum. I told him that I could go all night, and he laughed, as if to say, "As intriguing as that sounds, I am not entirely sure that my ass is ready for such a workout," so I laughed and told him that I would move things along. But I didn't, at least not right away. I slowed down and just lay on top of him, fully buried, and then I started fucking away, going deeper and harder than before. After another five minutes, I figured that I should probably give the poor guy a break, so I asked him, "Do you want me to cum?" When he said he did (not so articulately, but it was a clear affirmative), I said, "Then ask me to cum," which, usually, is the only way I can cum when I'm fucking anyone other than b&c. Anthony started to tell me to cum, and I gave a final burst of acceleration and complied.
I stayed inside him for a few minutes, then rolled off him and rolled the condom off me. I was going to make him cum, but when I reached to fondle his cock, I found that I'd already done that. He rested his head on my shoulder, and we held each other for a while, idly chatting. Very cuddly, that one. And then it was very late, so we got up, and I got dressed, and we had a few goodbye kisses, and he asked me whether we could play again. I said, "Absolutely," and I meant it, but I figure there's a pretty good chance that he'll be feeling a fair amount of remorse when he goes back to Ohio to see his partner this weekend, so who knows? But it was a terrific fuck with a sweet and cuddly guy, so I hope there'll be a repeat.
On the drive home, I was thinking, yet again, that I don't necessarily believe in the complete separation of sex and emotion. Sometimes I do separate them, of course, but more often it's simply that I'm nearly as promiscuous with my emotions as I am with my dick. I don't mind developing warm feelings for guys I fuck, even if I never see them again. I don't think that there's anything wrong with emotionless fucking, just like I don't think there's anything wrong with fuckless emotion, but I can handle significant amounts of affection towards large numbers of men. Sadly, most of them (and, I maintain, most men generally) aren't as evolved in that manner as I am, but, really, that's okay, too.
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