And Now for Something Completely Different

It's predictable, isn't it, readers? No sooner have I noted that I haven't played with any new guys in over a month than the opportunity arises.

I decided to take off half of Thursday and all of Friday. I really needed some time off after the recent tax deadline, and, more to the point, Logan was coming over Thursday after choir practice and spending the night, so I knew that I'd be in no shape to get to the office by nine on Friday. Anyway, since I was taking the time off, I figured I'd send Kevin a message and see whether he could play. Kevin's a local married guy that I played with back in the beginning of September but didn't, apparently, write about. He's a very solid, compact, bearish man who's a great kisser but who doesn't bottom much. He couldn't take my cock the first time we played. But he'd said that he was game to try again, and he was so much fun that I figured he'd be worth another go even if I didn't manage to fuck him.


And I didn't, but he was. He came directly from work, still in a starched business shirt, which I wasted little time relieving him of. I left him otherwise dressed when I threw him on the bed (You know, every time I think of throwing a guy on the bed now, I can't help thinking of that one guy who complained that I treated him like he was Scarlett O'Hara. But I still throw guys on the bed, and every other guy seems to appreciate it.), and we resumed kissing, rather frenetically. He's a very hairy guy, and the hair includes a goatee. The outside of my mouth was getting a kind of scratched up, but I didn't mind, and, in any case, I soon worked my way down to the nipples, where the fur was softer, if no less pervasive.

After he went down on me (very eager, but slightly toothy), I started to play with his ass with some lube and a finger, and then with two fingers. And he really got into that, but I couldn't help noticing that he was still really tight, and I doubted that I'd be able to get my cock into him. We tried, though: we really, really tried. I put him in numerous positions, and I'd get most of my head in and then he'd ask me to stop, and I'd wait for him to relax, but he couldn't. And I figured that I'd be fucking Logan six ways to Friday later in the evening, so it really wasn't a big deal. Anyway, I gave up, and when he asked me how far I'd gotten into him, it seemed like a good idea to prevaricate slightly, so I said, "Farther than you think," and, hey, I suppose that might have been true, even though I'm pretty sure it wasn't. Anyway, we went back to the frenetic making out, and I started stroking him, and we kept doing that for a while, until he shot all over himself. I wiped him up, and he said, "Man, you really know what you're doing," to which I smiled, modestly. He says he wants to keep trying to loosen up, so I guess I'll have to break out the entire range of anal toys and do my best. It promises to be something of a project, but, well, y'all know me: if the kissing is great, the sex is great, and I'm willing to do a lot to break in a willing guy who loves to kiss. I just wish he was a little more available. I know he's married, but his kids are both off to college, so you'd think he'd be able to sneak out, especially since I'm in the same town. But it's not exactly like I'm starving for companionship, so it's probably just as well that he's not available all the time.


(And speaking of anal toys, sometime that day, Nike texted me to ask whether I had a big dildo he could borrow so that he could work on opening his ass for me. I didn't reply, but I guess I should. I'm not sure about lending out my dildos, though, so maybe I'll just buy him one as a gift. There are so many options, though. Decisions, decisions.)

So far, Logan has always been available when I've suggested a session, and he even showed up a few minutes early Thursday evening. After an extended hello kiss, I offered him a glass of wine. He noted that it was a larger glass than usual and that it might take him a while to finish it, and I noted that we had all night. He smiled, and we actually chatted for a while, but then I got a little bit aggressive kissing his neck, and he gulped down the rest of his wine. I took my glass with me, which left only one hand free to grope his ass as we climbed the stairs, but life is a series of compromises, is it not?


Logan removed his jacket while I set my cellphone and glasses aside, and then I tossed him down on the bed, and he laughed. I said, "What?" and he replied, "Nothing, I'm just happy. I'm comfortable here." Later, when I had some time to think about it, I decided that "comfortable" was an odd choice of words from someone who always looks about as happy as Charlie Brown would look if he ever managed to actually kick that football. I'm guessing that in part it's the fact that English is likely his second or third language, but then maybe it's that he spends a lot of time in very uncomfortable circumstances. As far as I know, he's still living with his wife, even though they've decided to separate and/or divorce. I haven't really asked the details because a) it's not really my business unless he decides to share them, and b) the few times I've asked anything about his marriage, asking has seemed like the quickest way to eliminate his smile. I really like making Logan smile, and it's really easy to do.

He seems to smile most broadly when I'm fucking him, and I lost track of the number of times that we went from making out (which also makes him smile) to my pounding him in full-on fuck machine mode. He never says that it's too much; on the other hand, he did, for the first time ever, ask me to "go slow" when I was beginning to penetrate him the second time that evening. So I went slow for half a minute, and then I pounded. I had him on his stomach that time, and he grinned more widely still when I bit into the back of his shoulder. But Logan is long, lean, and limber, so we mostly fuck face to face: I can kiss him while I'm plowing him in that position, so it's truly the best of all possible worlds. Candide never had it half so good.


Nothing really turns me on as much as a guy who loves what I'm doing to him, so I was in paradise throughout our little slumber party. My cock is usually more than adequate for what I want it to do. And by that I mean that it rises to the occasion and stays hard while I want to fuck. It might go down to semi-hard during an extended make-out interlude (I'm not twenty any more), but a small amount of oral or manual attention will bring it back to fuck-ready hardness. With Logan, though, it just got hard and stayed there. And never really got close to ejaculation no matter how long or hard I fucked him. I wasn't really anxious to cum, especially towards the beginning of the evening. After two hours, though, when Logan had already straddled me and jerked himself near to ejaculation and then had let me grab him hard and pull the trigger, it would have been nice to maybe blow a load before sleeping. But the cock wasn't cooperating with that plan, so I drifted off with a hard-on and woke a few times with a hard-on, each time pounding Logan in one position or another. Then I'd withdraw, and we'd kiss for a while, and he'd smile at me, and we'd fall asleep again, always entangled. So you can see how it would be easy to lose count.

I pounded him a couple more times in the morning, and at one point, I had him on his back so that he was pretzled with his knees up near his ears, and I angled myself to get the maximum effect from repeatedly entering him and banging his prostate, and then, without warning, cum was pouring out of his cock and onto his stomach. It's rare for me to make a guy cum without even touching his cock, and it was very gratifying.


It was about 9 am by then, and I pulled him up and dragged him in the shower. I thought maybe that, having just ejaculated, he'd be tired of having my cock up his ass, but after kissing him and washing his back a bit, I bent him forward in the shower and fucked him from behind, and he was as eager as ever. But we only fucked that way for a couple of minutes, then we finished showering, dried each other off, and I tossed him back on the bed and lay myself and the comforter on top of him to stop his shivering. It worked, but then we spent the next two hours lazily kissing and groping and holding each other. He spent the last hour of that telling me, every twenty minutes, that he should probably get going. But I wasn't exactly kicking him out, and he seemed to lack much will to leave. He told me again how comfortable he was. He did finally leave around 11.


I went downstairs to check my e-mail, and there was a message from this young guy who'd been ambivalently pursuing me for a while. He'd say he wanted to come over, and then he'd cancel at the last minute, always citing something he had to do with his girlfriend. I'd eventually told him that I didn't want to bother with him, but then I'd seen him online a couple of days earlier, when I wasn't sure I'd have other options going on, and I'd said that I could play with him Friday around noon if he wanted. I figured that I'd already be home, so if he didn't show up, I could just get another hour or two of very badly needed sleep. And on Friday, he said he still wanted to come over but wondered whether 12:30 would work instead of noon. I didn't have a problem with that, so I gave him general directions and told him to let me know when he was heading out and call for the house number when he got close.

He did all that, and his car pulled into the driveway about 12:25. We'd agreed to what could and couldn't happen. He'd never been fucked, so he wanted to work up to that, but not actually get fucked in the first meeting. He wanted to be dominated and suck cock but not kiss. That should have made the alarms ring, but whatever. Anyway, he came in, and I told him to take off his shirt, then I twisted his nipples a little bit and pointed him upstairs. I smacked his ass a few times on the way up, then when we got upstairs, I told him to take off his shoes and pants. I kicked out of my jeans, told him to bend over the bed, slapped his ass a few times by way of punishment for earlier cancellations, and then told him to get on his knees. I fed him my cock for a minute, but he'd said he didn't have much time, and I really wanted to eat his ass while he went down on me, so I lay on the bed and pointed toward my cock. He looked very nervous, but he bent down and started sucking on me. It was okay, and after a half-minute or so, I grabbed his head and pushed it down. He took it for a few seconds then coughed and backed off, looking terrified. I just said, "Relax, boy." And then he said, "I'm sorry, I can't do this." And then he started apologizing more profusely. I didn't say anything: I just kept looking at him like, "Huh?" He got dressed, said, "I'm really sorry," and ran down the stairs and out the door.

Not entirely unexpected, you know? And I was both too tired (still, my cock was pointing straight up to heaven; it really does have a mind of its own, and what the hell is it thinking?) and in too good of a mood from playing with Logan to be upset, but it was weird. Upon further reflection, I think that I probably should have been more verbal, more dominant, and more detailed. He probably needed to be led through the encounter step by step, so it was probably a mistake to take him off his knees so soon. And I should probably have told him what to do every step of the way. But geez, so much work. I mean, he was young and sort of cute, and I wanted to be the first guy to eat his ass, but he wasn't anything special.


I considered taking a nap until 5, when it would be time to leave to pick up YFU, and I considered just jerking off, since I still hadn't shot a load, but I figured I'd at least give craigslist a try, so I threw up a quick ad, and the first suitable candidate to confirm was a married Latin guy who wanted to be blindfolded, tied down, and "taken when not in [his] own control," but who also liked to kiss a lot. He was also in the area, working, I think, so I told him to come on over.

I hadn't (and still haven't) tied anyone to the bed since we got the king-sized bed, and I really didn't want to take the time to get the ropes out and make sure everything fit properly, so I just got out the blindfold and a pair of handcuffs and left them on the bed. When he showed up at the door, we started making out, and he was obviously one of those married guys who melts when he's told what to do. He told me that he had forty-five minutes and asked whether that was okay, and, well, not a problem. I pushed him upstairs, began undressing him (another starched shirt), tossed him on the bed and went straight for the nipples, which, I gathered, were not used to that sort of attention. We made out for a while, then I fetched the blindfold and put it on him. I fed him my cock for a while, we kissed, for a while longer, then I pushed him towards my cock again while I went after his bubbly brown ass. I don't think he was used to that, either, but he was an instant convert. I shoved him down on his stomach, opened the condom package as loudly as I could, gloved up, and got behind him. He reached back, ostensibly to guide me in, but probably to feel my cock to make sure it was sheathed. And who can blame him? Anyway, I added some lube and began to make my way into his very tight ass. He was giving me the "no, no" but not the "stop" so I kept working until I was in. Then I started to fuck him slowly. It seemed to be a little too much for him, but I kept at it for a couple of minutes. Then I pulled out, flipped him onto his back, and re-entered him from that position. He was easier to get into that way, and I started talking dirty to him. He kept calling me "Daddy" and saying, "You're really fucking me!" As opposed to virtually fucking him, I suppose, but I was too occupied to give it much thought.

It was clear to me that I wasn't going to cum, at least not within the available time parameter, so I pulled out and we kept kissing, and I worked his nipples, then jerked him off. When he came, I continued to stroke him, making him jump and twitch. Then I wiped him off and pulled off the blindfold. After a few moments of recovery, he glanced at his watch, and I said, "I always meet my deadlines." He smiled, thanked me profusely, kissed me again, and left.


When I checked my email again, there was a response from a local twenty-one-year-old guy who wanted to be used hard. We swapped a few emails and established limits (he was open to anything except shaving and CBT), and he asked me to come to a local park to pick him up. He didn't have a car. I was a little bit skeptical, but I told him what my car looked like, and he told me what he'd be wearing (we'd exchanged pictures earlier). I got to the park when I said I would, and I thought I might have seen someone who matched his description hanging around the playground. But there were also kids playing there, and I really didn't want to get out of the car. The guy I saw never seemed to look towards my car. And there were several other cars parked there, apparently without agenda, which made the whole thing seem very weird to me. Perhaps that's the local cruising grounds. Who knew? Anyway, I stayed for a few minutes before leaving. When I got home, the guy emailed me to say that he hadn't seen me and asked whether we could try again, but I didn't have enough time to comfortably work through all of the stuff he wanted done to him. Besides, I was really beat from not much sleep and a lot of very energetic sex. I was also really hungry, and he just didn't seem as interesting as a cheeseburger at that moment in time. I told him to email me next week if he's serious about being tied down and getting spanked and having wax dripped on him and having his nipples used hard and getting fucked from both ends.

Then I retired to my bed with a DVD and the last few stories of Frat Sex 2 and proceeded to have a nice wank. I'd been hard an awful lot and hadn't come in a couple of days, so I was expecting a big load, and I was prepared for that, but I wasn't prepared for ejaculation arriving before the orgasm. Usually I control my masturbatorial ejaculations pretty well, but in this case, I knew I was still a few seconds from the orgasm, but my cock started spurting a great deal of very watery cum. I was about to be all WTF, penis? but then the orgasm arrived a moment or two later, and it was very intense, so I kind of lost track of my interior monologue. Well, nobody's perfect, right?