So I guess you really do learn something new every day.
I, for example, was under a complete misapprehension as to what it means to "milk" someone. (I do, however, understand exactly what it means to milk a dairy animal, so if you were about to explain that to me, there's really no point. I have a fair number of relatives who are farmers.) I had thought that milking typically involved restraining a guy and then masturbating him to orgasm and continuing to stroke him after he had ejaculated so that all his ejaculate was gone.
Milking aka prostate massage apparently involves draining the seminal fluid (known to us common folk as precum) by rubbing the prostate. As you can see from the aforementioned links (and more: just google "prostate milking"), there is some ambiguity as to the eventual goal of milking, but the technique appears to be relatively well defined.
Lest you think that I sit at my computer all day and research sexual variations (not that it wouldn't be a sweet job if I could get funding for it), let me explain that I was chatting with a sub with whom I play from time to time, and he asked me if I knew about milking and whether I was willing to milk him.
This guy is something of a demanding bottom, though I suppose that's as much my fault as his. After all, if I said, "fuck no" to any of his requests, it's not like he'd refuse to put out. And he does do pretty much anything I ask, within certain broad limits. (As with almost every sub I know, his limits are a lot less restrictive than my own.) But I often gratify his requests, if only so that I can say that I've done something.
Anyway, I wasn't sure that I was right about milking, so he gave me a url which wouldn't pass the office's content filter. So he emailed me the information from this page, and then it all made sense. This guy's first request is almost always that I don't let or make him cum during the session. When I'm in a petulant mood, I punish him by shoving a dildo in his ass and pounding hard until he shoots. I don't reckon that he's too upset about that since he invites me back. Besides, whether I deny him an orgasm or I deny denying him an orgasm, he's still being denied either way, so he's happy. I really can't say that I empathize with the mindset of a submissive, but I reckon that I understand it, at least on an intellectual level.
This guy proposed having "a buddy" install him almost entirely in his sling before I got there. (I'm pretty sure that means he does it himself.) Then when I arrived, the door would be unlocked. I'd lock it behind me, restrain his free hand in the sling, milk him, and fuck his holes.
I haven't always had the greatest experience with this guy's sling. It's because I'm short. Well, sort of. I'm six feet even, but I have the body of a guy who's 6'4 and the legs of a guy who's 5'8. (I hasten to add here that I don't think of 5'8 as short, or, at least, that I find guys of that size almost unbearably sexy. Though I suppose the same could be said for guys ranging from 5'4 to 6'9. I'd go farther, but I don't think I've ever fucked anyone taller than 6'9.) The last time I was there, I'd told him to three-quarters tie himself to the bed, but I told him he could have the sling set up and we'd move him to the sling after I'd fucked him on the bed. But he'd set the sling up for someone of my height, so I had to stand on my toes to fuck him, and it was kind of tedious and tiring. I managed by grabbing onto the top of the sling and sort of hoisting myself higher, but it's hard to fuck like that for long, and, frankly, this guy's not so tight that I'm likely to cum without fucking him for a long time.
Anyway, I told him he could be in the sling, but he had to set it lower than before, and after we negotiated the correct height, I gave him a time that I'd show up. Miraculously, I found a parking space near his home (he lives right on Logan Circle) and made it in time.
I hadn't bothered to give this guy the usual instructions this time around. I always tell him to be naked except for a blindfold or hood, and I assumed that he'd remember, but when I got there, he was hooded, but he was strapped into the sling, wearing some camouflage boxers (with the bottoms cut to allow easy access to his hole) and a gray ribbed tank. I was a bit annoyed because I'd planned on taking a picture of him in the sling, but the room was probably too dark to get a decent picture anyway. And, after all, I could still reach underneath the tank and pinch his nipples hard. He also had his ball gag in (he lives in mortal fear that I'm going to insist on kissing him), and he was wearing some white ankle socks that weren't all that clean. They didn't smell all that great, and that was a bit of a nuisance to me, but I decided to go with the moment. He is, after all, an eager and fun fuck, and he never complains about hard nip or nut work. Or if he does, he's got the gag in, and I can't tell.
He was, comme d'habitude, already lubed, and I'd trimmed my nails on the way, so (after securing his free hand) I grabbed the DVD remote and started the porn that he'd cued up on his massive TV, and I pushed a finger in and started to rub it around the periphery of his prostate. Every once in a while, I'd hit the center of the prostate pretty hard, and his body would go rigid, and the chains in his sling would rattle, and he'd make some sort of noise.
After four or five minutes of this, I'd gotten a lot of incoherent moaning through the gag, but I wasn't seeing much precum, so I pulled the gag out and replaced it with my cock. Naturally, since I was now at the other end of the sling, I couldn't easily massage his prostate, but I could tweak his nips pretty hard and rock him back and forth on the sling, sending my cockhead in and out of his throat. That did get the precum flowing, and it was fun besides, so I kept that up for a while. When I'd swing him too hard, my cock would come out of his mouth, but he'd root around for it hungrily, so I assume he was having a good time, too.
I guess that the head pulled back position gets tiring after a while, and he asked, between gasps for air, if I could come around to the side where it'd be easier for him to suck me. Ever the gentleman, I complied, and started bumping into him and swinging him from side to side rather than back to front.
When we were having our milking discussion, he'd said that some people use ice to keep the bottom from cumming when he's being milked. Accordingly, he'd laid out a small bowl of ice. It was the half-moon shaped ice that comes out of home freezers with ice makers. While I was fucking his face from the side, I grabbed one of those pieces of ice and rubbed it on his nuts and then around his hole. That made him moan some more, which was nice for my cock. Finally, I took the piece of ice and pushed it inside his ass and left it there. There was a lot of noise when I did that, but since I kept my cock in his mouth, I couldn't really be sure what he was trying to say. I decided it was easiest to assume that it was "thank you, sir!"
He had most of his toys out, and I grabbed a dildo that I'd probably call a silver bullet. It was metal with a handle, and I rammed that against his knob for a while, which caused a lot more muffled exclamation. But the silver bullet falls out if you don't hold it in, and I was tired of holding it, so I found a more flexible rubber dildo with a handle on one end and a rubber ball on the other. It did a good job of bumping up against his prostate, but it also stayed in when I let the handle drop. Unless I pinched his nipples really hard, and then it would plop out and I'd have to reinsert it.
I left the ball-ended dildo hanging out of his ass and started fucking his face from the end again. It was fun, but I'd already been there almost forty minutes, and it was clear that he wasn't going to get totally milked, and we'd arranged for me to be gone within an hour (B&c was coming back from Mexico City that evening, and I had to get over to Lambda Rising and buy him a pornographic birthday card), so I figured it was time for me to fuck him. I put on a condom and lubed it up a little then stepped up to his ass and slid in. Fortunately, he'd set the sling to the right height (and the ice cube had fully melted), and he never really requires (or wants) a gradual entry, so I pushed right in and started to plow. I pushed forward a few inches so that gravity would bring him back towards me, and then I stood still and pushed the chains forward so that I could fuck him without moving much. He started moaning more loudly (the gag was back in) and nodding his head up and down. Every so often I'd grab his cock for a few seconds (he never gets soft when he's in the sling) and stroke him just to make him think that I might make him cum, and occasionally I'd just rub my finger tip against his frenulum to make him writhe, but mostly it was just a nice, hard, rhythmic fuck.
When I was at the fifty-five minute mark, I knew that I wasn't going to blow a load within the hour by fucking him, so I pulled out, pulled off the condom, lay down on his bed, and stroked while watching the porn. He couldn't see me, and I stayed pretty quiet, but he must have known I was still there since he would have heard the bedroom door open if I'd left. I got pretty close pretty quickly, so I stood back next to him, made a little bit of noise, and let fly with five or six stripes of cum, all the way across his tank top. It was a good look for him, and he didn't cum, so I think he must have been happy.
I went to his bathroom and cleaned up quickly, then dressed silently, released one of his hands, walked out of his bedroom and then out of his townhouse right at the one-hour mark. I hadn't said a word to him the whole time I was there.
3 years ago