Tax Day Trifecta

Why is it that guys who are fucked up are often such good lays?  Is it that they just don't have sex very often because of the guilt, so when they finally get around to getting fucked, they've got all that tension to release?  Or is it the guilt itself? Perhaps they enjoy it more because they feel like they're doing something wrong?  I don't know: I just know that I seem to know and/or attract a disproportionate number of guys who are both fucked up and really great lays.  And it can be something of a problem because the fact that they're fucked up makes them unreliable, so I kind of don't want anything to do with them, but the fact that they're really great lays, well, the implications are kind of obvious, innit?  Add in the fact that I'm no good whatsoever at holding a grudge, and maybe you'll understand why I say, "Sure, why not?" when most of these guys (there are exceptions, and there are guys that I cut off absolutely, but mostly those are the guys who've committed the unpardonable sin of being bad in the sack) email or text me wanting to play.

And that happened with two guys on the fifteenth.  I had tentatively planned to make an appearance at the office's offsite tax day party (I attended the onsite party, because it was onsite; also: food).  I never stay very long as the party exists mostly as an excuse for the youngsters to drink heavily.  (Also the not-so-youngsters, but I never like seeing my bosses either shit-faced or hungover.) But sometimes I'll go and have a glass of wine before going home and either hooking up or having a wild night of Netflix and diet soda on the couch.  Anyway, on this tax day, I had later-evening plans to play with a boy (older than me, I think, but still a boy) who was going to be in town on business and whom I had fucked senseless (arguably not such a long personal journey for him, but whatever, right?) the last time he'd been in town on business.  So it seemed reasonable to hit up the party.

But then I got a chat message from this guy who's been saying since 2009 that he wants to be my slave.

So.  If you had the dubious pleasure of knowing me personally, you'd probably not think me a likely person to have a slave.  And you'd be right.  Nonetheless, it is a not uncommon occurrence for me to be hit up by random bottoms, from various Internet sources, claiming that they wish to serve me in this capacity.  And I have to admit that it's tempting.  Not because of the sexual aspects because (with all due respect to the slave-owning tops out there whom I am not judging [totally a lie: of course I'm judging you if you want to own a slave; have you never heard of the Thirteenth Amendment?  Or, I don't know, the Civil War? And don't give me that bullshit about how the Civil War wasn't fought over slavery; of course it was fought over slavery.  The people who tell you otherwise are racist scum who wear Confederate flag t-shirts. Not that I'm judging.]) being a hard-core dominant is something I only want to do once in a while, and even then, I'm not so much hard core as maybe firm core. Yeah, that's me: an occasional firm-core dominant.  You can see why I don't use such a description in my online marketing. 

Anyway, the thing is, most guys who want to be slaves fall into one of two camps.  First there are the guys for whom it's entirely a fantasy, and these guys are mostly trading email messages with you where they talk about the joys of being owned, and if you oblige them by fabricating similar messages about how you want to put their cock in a chastity device or house them in a cage or whatever, they're just going to use those messages to wank out some unspecified number of loads, but they're never going to actually show up at your place for service.  The other group are the people who totally misunderstand the entire concept of slavery and, in effect, want to be kept men.  They hate having to go out in the world and earn their living.  They hate having to make decisions.  So they want to lie about the house all day while you're off earning your paycheck, and maybe they'll do the odd bit of housework, and they have dreams of being fucked senseless (here again, no great accomplishment, given how little sense they have to start with) every night.  And while real slavery is -- OF COURSE -- abhorrent, fake slavery is just dumb.  Real slavery was an economic institution, and no sensible slave owner would have purchased a slave who wasn't going to be an economic asset.  And when you explain this obvious bit of economics to members of the second group, they kind of dry up and go away.

But then there are a few people who basically want to be part-time slaves (a proposition that is nonsensical on its face, but whatever), and I am embarrassed to admit that I have tried with a few of these people because, well: free housework.  But it never works because it turns out, unsurprisingly, that slave wannabes and cleaning fetishists are mutually exclusive sets, and whenever I've had someone claiming to be a slave come over to clean my house, he always requires lots and lots of supervision and is not very good at cleaning.  In other words, I have to stand over him, and, oh fuck, just hand me the mop and get out of my house and I'll have it done in half the time.  There was one guy that used to just be a hook-up (at which he was very skilled) who over time wanted to be more and more enslaved when he left his girlfriend at home and came to see me for 1-5 hours, and he would clean some, but when my patience had been worn away to the point where I decided to just leave him at home when I went back to work (I knew where he lived, and it was tax season), he spent time that was meant to be spent cleaning trying to shove increasingly improbable items up my ass.  And while that large bottle of dark sesame oil was very likely already rancid, I still resented having to throw it away when I came home to find it in my shower, covered with fecal matter. (I mean, wtf, dude: I HAVE sex toys.) After a short while, I came to realize that this guy just liked making me angry so that I'd fuck him harder, and after a not much longer while, I just couldn't handle it any more, and I decided that I should send him on his way before he provoked me into doing more than just slapping him around.  (I did not slap him around hard enough to leave a bruise, and I would generally do it when I wasn't angry because he liked it so much, but I find anger especially toxic, and I don't ever want to experience myself out of control.)  There was another slave wannabe who showed some potential, but he was horrifically unreliable, and mostly what he wanted to do was iron my shirts, and, I mostly buy the Lands End no-iron cotton shirts, and when I don't, I just really don't find wrinkles to be such horrible things.  You know?

Anyway, the guy from Monday/tax day was somewhere between those first two groups of slaves manqué.  He probably has some legitimate desire to be closely controlled and to be fucked hard and rough, but he has no follow through.  I had gotten to the point where I would reply to his (not very frequent) messages with a "let me know when you're ready to come get fucked; I don't have time to make up shit for you to jerk off to." But he seemed earnest this time, and I really didn't want to go and hang out with my colleagues, and I figured that if he didn't show, I could start getting caught up on my laundry and cleaning or (more likely) turn on the tube and melt into the sofa.  And, of course, there was always the off chance that that other guy would follow through.  That other guy is a bottom who lives deep in the heart of DC, high up in some very nice apartment building with absolutely miserable parking, and I usually travel to see him because he usually contacts me when he's home alone and drinking.  He's another one of those guys who are unreliable but freaking hot in bed, so while I've learned not to expect anything from him, I can't quite write him off entirely.  Well, I came really close a few months ago when he said that he was going to travel out to see me and didn't show up and then hours later had asked me to come to see him because he was drunk, and I finally figured that the timeline had been a) he asks to come out to my place to see me, b) he goes out to a bar and drinks a lot and tries to hook up, and c) he asks me to come see him when he strikes out at the bar and is too pissed to drive.  It made me kind of angry, so I told him not to contact me again, but then right near the end of busy season he emailed me to apologize and told me how much he missed my cock (not me, mind you, but it's not like I want this guy to be into my personality since I would never, ever date him, even if he weren't closeted), and I was feeling forgiving (as I almost always am), and I figured it would be ok to see him if he agreed to come out to my place AND I had alternative plans for the evening.  Double (or triple) booking is a good strategy for dealing with people like these two guys because the odds of both of them showing up are pretty low, and if they do both show up at the same time, well, either a) woohoo, it's a party, or b) one of them gets offended and leaves, and while I normally don't like to offend people, these are people who've already misbehaved pretty badly, so I'm not going to feel even slightly remorseful if they waste a trip.  And, in practice, I can't remember a time where someone showed up when my bed was already occupied and didn't decide to just join in.

So that other guy had emailed me a couple of times and said he'd come over when he was done at his office.  He'd had an original ETA of about 5:30, but he didn't end up arriving until 8, by which point the first guy -- who did, in fact, show up -- was just a distant memory.

I knew first guy was a submissive, so I, naturally, grabbed him and sucked his tongue down my throat as soon as he walked in the door.  This guy's like 6'3, massive, and solid, and it's always fun to dominate a guy who could destroy me in a fight, if I were a fighter.  Which I am not: I'm a lover.  Anyway, he was into it right away, and I had him upstairs and half-undressed and under me on the bed all in pretty short order.  And it was all hot and good except that he kept coming to the edge of freaking out, and I had to talk him back down.  Where "talk him back down" means "grab him and throw him down on the bed and tell him to re-fucking-lax." And -- it must always be so, apparently -- at some point I grabbed his cock kind of hard, and after about three seconds, he pushed me away and sat up and went all rigid, and it was obvious that he was trying to hold off a highly premature orgasm, and he actually managed to do that.  Unfortunately, I started to laugh because the whole situation was too ridiculous not to, and he said something about how if he'd cum, he'd feel all guilty for cumming too quickly, and now I'm sitting there of two minds because mind a) just wants to shove him down on his stomach and fuck him hard and without lube until he screams for mercy, but mind b) wants to explain to him the way things really are.  And if there weren't other guys in the pipeline, mind a) would likely have prevailed (except there would have been lube because he was really tight), but as it happened mind b) mostly won out, so I put him on his back and made out with him some while explaining to him that he was taking the whole thing waaaaaay too seriously, but then he got close again, and then he checked his cell phone and told me that he had to go because his sister had been running in the Boston Marathon, and he had texts from another sister and his father saying that she was in the hospital.  And, well, damn.  I'm pretty sure he was telling the truth about all of that, so I really had to be nice to him at that point, which likely means that he'll never be back, and that's too bad because submissives built like linebackers -- while not exactly rare -- are good additions to any top's harem.  I kind of wish I hadn't let him stop me from jerking him off (not that I necessarily had a choice: dude was strong) so that now I could say, "Easy cum, easy go," but, well: easy come, easy go.

I checked my email, and Rich (aka second guy) was running behind (no surprise there), so I took Luna out for a walk and then came back and sofaed for a while.  By 4/15, my mind is pretty much mush unless there's a difficult tax situation or an appealing piece of flesh to focus it, so time passed pretty quickly on to about 8:30.  I was starting to worry that Rich was either going to bail or -- worse -- run into the time for my hotel boy, but I forgot about that when Rich showed up.  He'd come right from work, and he looks delicious in a suit.  My inborn-and-hard-to-control inclination was to undress him right away, but Rich is kind of a high-maintenance lay, meaning that it was going to take a glass of wine and some conversation to get him upstairs and naked.  I'm not a big drinker these days, but I still had maybe a quarter of a box of Black Box Malbec (which I cannot recommend highly enough because it's pretty good, and the collapsible bladder inside the box means that it stays tasty for many weeks), so I pulled down two of my oversized red wine glasses and we sat on the couch and discussed the superiority of red wine.  It turns out that he's from Napa originally.  Who knew? 

Ten minutes later, I refilled his glass, and we headed upstairs, whereupon he headed into the bathroom to take a shower, leaving me to sip my wine and wish that I'd insisted on undressing him, but he wouldn't have liked that (without significantly more wine), and Rich is the sort of guy who demands and rewards patience, so I waited, and before long he appeared, wrapped in one of my big white towels.  He's totally smooth with really good skin, and about 5'9, and slightly fleshy, but solid.  He's hard to describe, but he's almost pretty, yet entirely masculine.  I lay him down on the bed and started to kiss him a little bit: he warms to that very slowly, but with persistence, and some detours to work his nipples, he gets more and more into it, so sex with him is always a long, slow, awesome process.  Thirty minutes later, he was going down on me, and I was slowly and thoroughly eating his hot, tight ass.  Sixty minutes later, he was on his side, and I was slowly pushing my cock into him en route to a hard fuck.  Ninety minutes later, I was on my back, and he was sitting on my cock as I alternately stroked his face and twisted his nipples, and he came hard on my stomach.  Ninety-one minutes later, he was rushing off to the bathroom and then getting dressed.  Dude doesn't stick around afterwards: he's too busy working through the guilt, or whatever, but while we were playing, I'd heard my cell phone make a notification that I was pretty sure was Hotel Boy, and since I was saving my load for him, I couldn't very well complain about Rich shooting and running.  Especially after he'd been there two hours in all. 

After I saw Rich out and fed Luna, I jumped in the shower and headed down to Silver Spring and Hotel Boy's hotel.  He met me in the lobby, and I shoved my hand down the back of his jeans in the elevator up to his floor.  HB is shortish (maybe 5'7) and trim and cute and very, very willing, so I tossed him down on the bed as soon as he had his shoes off (I used the time to put my glasses and cell phone on top of a bureau) and began to kiss him.  He's got nice lips and he uses them well, but I knew I was running on fumes at this point, so I moved on to his nipples pretty quickly, and by the time we'd been on the bed for ten minutes, I had him fully naked, and he was going down on me.  I let him just suck for a while before I told him to put his ass in my face, and I probably only had my tongue up his ass for another five minutes before I was shoving him down on the stomach, and applying the lube (I'd made him put the condom on me, of course: there are rules, after all), and entering him slowly.  He's got narrow hips and a very tight hole, so it takes me a bit to get into him, but he was also eager, and I wasn't feeling especially in the mood for oh-baby-let-me-fuck-you-nice-and-slow-tonight, so pretty soon I was bang bang banging away at him, and he was alternately biting the pillow and, um, vocalizing is the word I'm looking for, I guess.  If I'd been at home with him, I'd have taken the pillows away and let him shout, but even though the Marriott seems to have pretty thick walls, I don't like to make too much noise when I'm in public accommodations, so I pushed his head down into the pillow and fucked him harder and harder until I unloaded into the condom. 

If ever there was a time to roll over and go to sleep, this was it, but I'm nothing if not polite, so I lay on my side, shoved a couple of fingers up his ass, and sucked on his nipples while he jerked himself off.  Then, while he was off grabbing a towel, I did actually fall asleep for a few seconds, but there was no way either of us wanted me to sleep over, so I wiped up and put my clothes on.  He had, meanwhile, collapsed on the bed and was making half-sleepy, half-satisfied noises about how well-fucked he felt, and I leaned down and kissed him goodbye then headed back to the parking garage and then home.  I could have slept for a day -- especially since I had the next day off -- but I had to get up and walk Luna the next morning.  No rest for the wicked, I reckon.