I finally reconnected with S., my young (compared to me), thin (compared to most everyone), super-sweet (compared to anybody) Indian massage buddy last night. We'd been trying for a while, but schedules weren't meshing, and I was beginning to wonder if maybe he was too shy for a second meeting, especially after he e-mailed late Wednesday to say that the guy installing his carpet was going to be coming by Thursday evening, so he wasn't sure it would be a good time after all. But he did finally e-mail me again last night to say that the carpet guy was gone and to ask whether I could still come over. So I told him 9:00, which gave me time to finish up some more work and then head over.
I realized as I was headed out of the office that my fingernails were too long for me to be probing his ass, so I made a quick stop at CVS to get some clippers and emery boards. I should have these in my car at all times, and I used to, but late last year, after years of exemplary driving (really), I wrecked my car, and when I went to the junkyard to clean it out, I somehow forgot a few things.
So, anyway, I clip the nails, and then I'm driving up Wisconsin Ave, filing my nails like I'm a housewife of Orange County or something, feeling entirely ridiculous but at the same time getting worked up thinking about my fingers in his ass. His very tight, very pretty ass.
I get to S.'s place, and I wrap my arms around him and start to kiss him, and he's very shy but he's responding, all at the same time. Damn, but that boy has lips. So we do that for a little while, and then we head for the spare bedroom, so I can give him a massage. He apologizes for the state of his house (the old carpets have all been pulled up, and everything's been taken off the walls in preparation for whatever work he's having done; I note the bare wood floors and hope that he's not going to cover them back up with wall-to-wall, but my mind is really elsewhere), but he's got a bed, and there's a chair with a towel and the baby oil, and what else do I need?
He leaves and comes back in his boxers and lies down on the bed. I start to rub his back a little, but it's very warm, and that makes me realize my hands must be cold, so I excuse myself, head to the bathroom, and run some hot water that I put my hands and the baby oil bottle into. Then I head back and get to work on him.
He's a lot more relaxed this time around, and he asks me about my party. I'd invited him to dinner the next night (which is now tonight). I work all kinds of hours at this time of year, and I still have my normal family obligations, and my social life usually takes a two-month nap, but this year I said screw it I'm going to invite my friends to dinner and make a big pot of chili and some sides and buy some desserts (which I would normally only make myself) and get a bunch of beer and wine and make some of my amazing martinis, and we'll all have a great time on Friday night, and then I'll be back in the office at 7:30 am on Saturday, and maybe I'll be exhausted, but at least I'll be happy. So while I'm working S.'s neck and back, I tell him that it'll just be very casual and a bunch of good guys and ask whether he's coming, and he says that he'd really like to but that he doesn't drive and he'd be happy to take a cab there, but he'd worry about getting home.
I'm working on his lower back, on the left side, now, and I know that's a problem area for him, but he's really enjoying the massage, so I don't say much, but my mind's working while I'm oiling him up and sliding the waistband of his boxers halfway down his very tight, very pretty ass, and I come up with a solution, and it makes me smile, and I tell him that I'm pretty sure I can get him a ride home, but we can discuss it later, and I'm not sure he's listening any more, anyway, because he's purring a little.
I knead his buttocks really well, and then I run my index finger down to his asshole and play around the outside for a bit and then put the fingertip up against it. With my other hand, I dribble some oil onto the top of his ass crack, and it runs down and makes a little puddle where my index finger dams it up. I press a little and my finger goes in, and it's very tight, and I can tell he likes it, and I take my other hand and work that problem area on his lower back while my index finger hunts down his prostate. After a little bit of that, I decide to work his legs, so I get more oil, and I work down his thighs and calves and then, one at a time, I massage his feet, which he really likes. Then I run my hands back up and get into some more serious ass play. Index finger first, then middle finger, but when I put them both together, it's already more than he can take, and I'm thinking "this boy is too sweet and too tight for me to ever fuck." With time and persistence, I'm sure I could get around the tight part, but I decided right then that I probably don't want to get around the sweet part. There are plenty of slutty bottoms out there for me to fuck. I'll leave fucking S. to his (as yet nonexistent) boyfriend, who hopefully will be someone like me, only five years younger, and with a much thinner cock.
But S. was enjoying the single finger and the rubdown, and there's way more to sex than fucking, so I told him to roll over on his back, and I took off my pants (but not my boxers) and lay down next to him and we started to make out. Damn, but that boy can kiss. I was flicking my thumb over one of his nipples and feeling his very full, very soft lips dance with mine, and it was just heaven. And you know that moment when you're with a guy and he's having a good time but he's still a little bit guarded and then suddenly the last bit of his defensiveness melts away and his whole body simultaneously relaxes and engages you as he surrenders to pleasure? Yeah, that happened, and, well, wow.
So we stayed that way, his arms around me, our lips playing, my hands working his small-but-perky nipples for a while, and then I started to play with his cock. Mmmmm, small dick. I love it. After a few minutes of that, I grabbed his hand and put it on my cock, and he held it lightly and stroked it, which I liked even more than I usually do. Then I spread his legs and started to finger his hole again, and then I told him to turn back over (I got rid of my boxers), and I spread his cheeks and started to eat his very tight, very pretty (and very clean) ass. He wasn't, I think, expecting that, but I'd been looking forward to it for days, and he loved it. He is, by nature, not demonstrative in bed, but where before I'd had to infer his enjoyment from the (very clear) reaction of his body, he now vocalized his excitement, and that really got me going. After some protracted tonguing of various degrees of intensity, I ran the tip of my tongue up his back to his neck and started to lick his ear while my very hard cock played between his nuts and his asshole.
He was moaning now, and I kept alternating between kissing his ear and kissing the back of his neck as I readjusted my cock so that the head was right up against his asshole. I pressed a little bit, and he said, "Ted, no" very softly, and I laughed a little and said, "Don't worry. I'm not going to enter you. I would never fuck you without a condom, and I don't think there's any way this cock would fit inside that ass, even if I wanted to." So he relaxed and enjoyed feeling my cock rub him, but after less than a minute of that, I told him to roll back over. I was ready to finish him off.
We went back to kissing, and I grabbed his cock and started stroking. I was going pretty slowly because I knew that's all it would take, and after a couple of minutes, I decided to suck on one of his nipples. A minute of that had him really worked up, and he said, "Ted, I think I'm going to cum," and I said, "Well, I sure as hell hope so," and then I kissed him and kept stroking him. He jerked a little, and the semen began to flow. I kept stroking until he had a nice load on himself, and then I grabbed the towel and started to mop him up, kissing him all the while.
I held him for a bit longer and told him that I was going to call a friend about a ride for him, then I picked up the cell and left a message to that effect with my buddy G. G. is the living proof that it is, indeed, possible for me to have a gay male friend whom I've never had sex with. (In fact, I have many. Or at least several. Or at least two.) Then I embarrassed S. by telling him how nice various parts of his body are and by telling him that he was going to be the cute young thing at my dinner/party and how he was exactly the kind of guy that G. goes for in a big way. I'm sure that S. was now blushing furiously, but one of the many reasons that I'm jealous of men with dark skin is that they can blush all they want, and it doesn't show.
I got dressed and got in the car and G. called me back, and I told him that the guy I wanted him to give a ride to was a cute, young, Indian schoolteacher, and I'm pretty sure I heard him salivating. G. is a terrific guy. He's in his mid-fifties, but he looks more like mid- to late-forties, and he mostly goes for guys about half his age. S. is actually a bit old for him, at thirty-two or thirty-three, but if you met him, you'd think he was at most twenty-five (it's the smooth dark skin and the shyness), so he's just right for G. And since G. already has a boyfriend (who lives in NYC, though), he'll be entirely happy to just fool around with S. without any butt sex. And I'll probably get to keep giving S. massages with happy endings. Everybody wins.
I felt GREAT after playing with S., so I ran off to the supermarket and then home, where I made the cole slaw. I mixed it with my hands, and my fingertips stung a little from the close clipping I'd given them. They're still a little sensitive today, and that's a very nice physical reminder of where they've been.
3 years ago