Best Laid Plans

B&c is out of town for a bit, and that always means that I'm looking to hook up. A couple of weeks ago, I was talking to Rex (or whatever I've called him in the past), who's been a consistently excellent fuckbuddy on an intermittent basis for more than five years. He lives in NoVA, so I don't see him very often, but he never disappoints, and I can take him to a 9 on the nipple scale. My limits (no breaking the skin) kick in before his do. At least usually. We'd exchanged a number of emails, which had ratcheted up the anticipation level. Normally, I avoid building expectations, but, hell, it's Rex, and I've never met anyone more appreciative of what I have to offer. He'd said that Monday was his last day of work before a vacation, and that he'd likely be tired, but he'd just take a nap and leave the door unlocked for me. I love that. In his last email to me, he wrote

I don't know if you'll find this strange or not - couldn't blame you if you do... I find it strange; Lately I've indulged a fantasy - not a true fetish, a fantasy... of dressing privately in women's lingerie. It helps to put me in a "bottom mood". I find I'm nearly insatiable after putting on panties for instance. Do I know how ridiculous I'd look trying to pretend I'm a woman? Absolutely. But thinking about being with you, with the attention you pay to my tits and my ass, makes me want to get ready for you by maybe wearing some panties. So if you walk in and I'm asleep in panties, don't bust out laughing. God. I can't imagine why I'm telling you this. I guess I hope it'll turn you on in some perverse way.

I'm not a big fan of men in panties. I'm not sure how much of that is that when I'm fucking a guy I want to be fucking a guy and how much is that women's panties are designed for women, and most of the guys who wear them are the ones who can least pull it off. Whichever: I don't mind guys who are feminine, but I'm not so much into guys who look feminine. But Rex was promising to be insatiable, which could only mean that what I'd hitherto assumed was his version of insatiability was really his version of difficult-but-not-impossible-to-satiate. If a pair of panties was going to take him to the next level, then why the hell not?

Rex had asked me to call as I was leaving the office, in case there was a problem at his job, so I did, and there was no answer. I thought that maybe I should just give up since driving from Bethesda around the beltway to Annandale in traffic is sure to put one in a bad mood if there isn't sex at the end of it, but I figured that he was just beat and already asleep and waiting for me. So I headed out of the office, and -- after a combination of horrific traffic and missing an exit -- I arrived at his condo a mere fifty-five minutes later (when it's not rush hour, and I make all the right turns, it's a 20-25 minute trip), where I found the door locked. I could see his car in the parking lot, so I knew he must have been home and was probably asleep. I called, I knocked, I swore, but none of it got me any closer to my goal of working his nipples until he was screaming and asking for more.


So I filled the car: gas is a few pennies a gallon cheaper in NoVA and headed home, and I was almost back to Maryland when the phone rang, and a very sleep Rex asked me where I was. I told him what had happened, and I could tell that he was crestfallen. He had thought that he'd left the front door unlocked.

I was pretty angry. I mean, I could have just not made the trip over there when he didn't answer the phone, but Rex always emails if something has come up to cause him to cancel, and making the drive had seemed like a reasonable thing to do at the time. Also, I was suddenly looking at a bad week. I had plans the following evening to have Mike tied to the bed for an hour while I edged him, and that's the sort of thing that I very much enjoy if I've played with someone else the night before. If I haven't, though, I feel put upon, even though it's a lot of fun. I didn't really feel much like turning around and going back to Annandale, but I remembered the concept of sunk costs. You have to look at the situation afresh and compare the effort from here on with the benefit from here on. I told Rex I'd be back as soon as I could. It took a few minutes to exit and get turned around, but I was back at his place soon enough. I'd told him to go back to sleep and that I'd wake him up, which is something that gets me going.


When I got there, he was in bed, but he was sitting up. I had to stop in the bathroom, then I shucked my clothes and climbed in with him. He had some of that post-nap disorientation still going on, but he certainly responded when we started to make out. He'd told me that he loves his nuts worked almost as hard as his nipples, so after a couple of minutes of kissing and feeling his naturally very smooth skin, I grabbed and pulled. He kissed harder, and he kissed harder still when I grabbed one of his nipples and pinched it hard.

Rex typically brings out the aggressor in me, but he's also a terrific kisser, so I kept easing off the hard nip and ball work and returning to the gentler making out. I'd kiss him and stroke his hair for a while, then I'd bite his nipple as hard as I dared. It was all great. Eventually, as he is wont to do, he started to go down on me, and he's a champ at that, too. I lay back and kvelled for a while, and he kept on keeping on until I pulled him up for more making out. We'd probably been rolling around for forty-five minutes when he decided to go down on me again, and I pulled his ass around to eat it. He always has the cleanest ass, imaginable. I think people must rent it out to do surgery in (it's pretty roomy, too). And everything was going swimmingly with my tongue deep in his ass and my cock deep in his throat until I reached between us and grabbed both his nipples and pinched, and suddenly, he jumped off me, and he was angry. "You've pushed them too far," he shouted, and then he turned his back to me.


This situation struck me as nothing so much as incredible. I wasn't annoyed or upset or anything other than incredulous. I just couldn't wrap my mind around what was happening. After a minute, he looked back at me and asked how he could help me cum, and I just stared at him, as if to say, "Huh?" He said he didn't know what was going on, but that he'd suddenly stopped "looking forward" to the rest of the session. I was still at the "Huh?" stage, so I just stared at him, and he said, "Maybe we need a safe word or something, when the nip play gets too intense," and at least I had the presence of mind to say, "You can just tell me to stop." Because, really, he could. He's even done it before, though, admittedly, once he tells me to stop, he almost immediately tells me to un-stop.

Anyway. We lay there for a while and talked, but it was pretty clear that anything sexual was over. I still couldn't believe it, but there it was. I finally got dressed, and Rex walked me out, then took off on a walk, "to figure out what's going on in [his] head." I have no idea what was going on in his head. My best guesses are that he was expecting entirely rough and I was mixing rough with tender or that he was just groggy from the nap and tired from a long day. Either way. He said, as I was leaving, that he'd see me again, but I have my doubts. He's great in the sack, but the best thing about him has always been how incredibly reliably horny he was to play with me. It was something I never doubted when I went to see him, and if it's not something I can rely on, I'm not sure I want to go after it, especially to Northern Virginia.


I couldn't help but think that it was the end of a beautiful, if occasional, sexual friendship, but I was amazingly calm throughout the whole thing. I had pretty much gotten what I needed out of the encounter during the first ten minutes of it, and the rest was very nice and then it was very over, but even though I didn't get the physiological release, I got the emotional release, or at least the emotional relaxation. And, as for our interaction ending, well, these things happen, right?

I was reminded of something that I'd said to someone recently, in an email about a (very) small perceived slight:

I don't mind that there's unpleasantness in the world, so long as it's someone else's fault.

The sentiment is wrong on many levels, but it's how I feel. Probably as an artifact of my upbringing, I'd generally much rather deal with misery than with guilt, and I hadn't done anything worth feeling guilty about.


So I was relaxed, but I was still totally wiped from the long day and the experience. I drove home, and I did a little bit of housework, then I started to hem some pants. But I was also logged into gay.com, and before long, Kip, who'd seen me on there, sent me a text message saying that he was horny. I get one of these messages about three times a week, and I routinely ignore them, but Kip never gives up. He told me that he was willing to get fucked, finally, and I knew that he really wasn't ready, but he also wanted to make out, and I thought that might be fun. I knew that neither I nor my cock was up to fucking anyone after the events of the evening, but Kip is fun to kiss, he always travels, and he's usually in and out in twenty minutes unless you make a Herculean effort to slow him down. Twenty minutes of making out and eating smooth ass, ending with a quick blowjob on a small, uncut cock was exactly what I needed. So I told him to come over.

I jumped in the shower and put on some boxers, which I did not intend to remove. When he arrived, I pushed him towards the stairs, and he told me that he'd lost ten pounds in the last month. He's been going to the gym ever since he broke up with his boyfriend. Ten pounds normally isn't that much, but Kip is 5'4, so it made a big impact on his little body. He suddenly had visible abs, and his butt was even firmer.


He lost no time in stripping down, and I climbed on him and we began kissing. He really was very worked up, and between his fat lips and his tiny nips, I soon had unanticipated wood. I didn't intend to do anything with the wood, but it was interesting to feel. After a while, I rolled him onto his stomach, spread his cheeks and dove in. He seemed to be opening up very well to my tongue, and he kept shoving his ass back onto it. I went as deep as I could, of course. After a while, I had him sit on my face so he could play with my cock, and he even sucked the head a bit. The boxers didn't come off, but it was very hot. We were coming up on the twenty minute mark, so I let him straddle my chest and fuck my face while I fingered his nuts and hole. He can thrust as hard as possible without getting anywhere near my throat, so I feel like slightly less of a bad cocksucker when I'm going down on him. It was only about a minute before he started to cum. His load isn't that huge, so I just took it and kept sucking after he'd finished pumping it out. He tried to pull away, but he's tiny, and I figure that if you're going to cum in a guy's mouth, you should just take your punishment, so I held him tight and smiled when the sensitivity overwhelmed him.

Kip got dressed, and told me he'd text me again. I told him, sure, but that the next time he'd have to be ready to be fucked. Which he might. He thinks that his ass is too tight, but I'm pretty sure it isn't. Anyway, he left, and I jerked off, and the orgasm and the cumshots were all magnificent.