I learned my lesson last weekend. I might not be fooling around much for a while: b&c just got back from Bogota, and while he's off to Denver tomorrow morning, he'll be back Thursday evening, and then he's home (or on vacation with me) for a couple of months. So instead of talking about the weekend's four encounters (Well, really five, but the two-hour session with b&c doesn't really count, does it?) in a catch-all post, I'm going to draw it out, starting with the two least satisfactory play dates. It was a pretty good weekend, overall, so we'll just get rid of the least pleasant parts first.
Saturday afternoon, not long before b&c was due back and I was due to attend one of YFU's Nutcracker performances, Juicy showed up. I call him "Juicy" because his e-mail address includes the words "juicy" and "booty." Neither of those words is particularly descriptive of him, but I reckon that people don't always see themselves the way we see them. Anyway, he was a short, thin, bearded, married guy who smelled very strongly of cigarette smoke. That didn't keep me from kissing him, of course, and he wasn't a bad kisser, but he clearly had eyes only for my cock. He reached for it as soon as he was in the door. I pointed him toward the stairs and alternated grabbing and slapping his ass as I followed him up.
I threw him on the bed, and I made out with him for a minute, but then he got up and, explaining that he had to go to work after we played, proceeded to remove and fold his clothes, to avoid wrinkling. I was still dressed, but I was commando, so it was pretty easy for him to unzip my jeans and pull them down to my thighs before he got on the bed. I grabbed him and started to kiss him again, but he couldn't be kept away from my cock, and he soon dove down and started to suck on it.
He was a decent cocksucker, but it was clear that he was in a hurry. I was somewhat tired from Friday evening's and Saturday morning's sessions, so I figured a quickie was all right. I pulled him around and went to work eating his ass. He reached back to pull his cheeks farther apart, so I shoved my tongue in farther, then reached under him to squeeze his nipples while I rimmed him.
That was all fine, and he seemed equally fine when I started to slide a finger into his very tight ass. I pushed against his prostate, and he started to moan. I sucked on his nuts for a bit, and then I pulled his cock back and began to finger it, spreading his precum around his cockhead and then rubbing it into his asshole. That was when I realized that I still had my sweater on and there was precum all over it. It's machine washable, so no big deal, but I figured I should take it off. When I did that, I handed him a condom, and he put it on me. I applied some lube, and he started to sit on my cock. He really was very tight, but I managed to get almost half of my cock into him before he pulled himself off my cock and excused himself to use the bathroom. I lay back and stroked myself, and he soon came back and said that he was bleeding. That struck me as odd: I keep my fingernails very closely trimmed and filed so they're not sharp, and I really wasn't that far inside him. I offered to do something else to get both of us off, but he said that the bleeding had made it impossible for him to enjoy himself. Then he got dressed and showed himself off, wishing me a happy rest of the weekend. Oh well.
Friday night, I was winding down from a truly spectacular encounter involving a young bisexual who I'd played with a couple of times a couple of years ago. He's just moved back to the area. He was kind enough to bring some 420 with him, and that made the sex even better than it had been before. So maybe I was still a tiny bit cloudy when I fielded a response from a craigslist ad. But maybe not. The ad response was very brief, and I didn't ask many questions when the guy called me, but I leave it to you to judge whether a photo that only shows an ass in a thong is enough of a clue to make one ask, "Are you planning to come over in women's underwear?" I tend to think that wearing a teddy and women's panties is something that one has an affirmative duty to disclose, but maybe I'm just a prude.
Anyway, the guy was a cute, young Latin guy, and when he showed up at my door and I started kissing him, I noticed that his jacket, jeans, etc. said, "Latin American soccer fan." It wasn't until I had him upstairs and he unzipped the jacket and removed the jeans that the clothes said, "I enjoy being a girl." He was pretty ugly as a girl, but he was kind of hot as a guy, so if I just kept my eyes above his neck or below his waist, it was cool. He resisted my attempts at further kissing, going instead for my jeans and then my cock. I kept my eyes closed.
Before long, I pulled him around so that I could get at his very fine young ass. I made short work of the thong, then spread the cheeks and shoved my tongue in. I tweaked his nipples at the same time, and it was okay. It was a great ass, and I was getting pretty good head. But I was still a little bit disaffected with the undisclosed teddy, so I didn't eat for nearly as long as usual before I pushed his ass off my face and toward my cock. I handed him a condom, and he put it on me. He started to mount me in a reverse cowboy position, but he had some trouble getting his ass to fit around my cock. I didn't like the position because I couldn't reach his nipples, so I spun him around, applied more lube to my cock, reached under the teddy to grab his hips, and pulled him down.
He was having a fine time bouncing up and down, and, well, you know, there's a tight ass around my cock, so I can kind of overlook the fact that the hot boy is wearing bad underwear designed for the wrong gender. But I couldn't ignore it for long, and maybe I was tired from the 420 and great sex earlier, but I found my patience less expansive than usual. I pulled him off my cock and shoved him down on his stomach, then I mounted him from behind and fucked him hard. He was moaning a lot, asking me to cum, but I was nowhere near an orgasm, and I wasn't sure I'd ever get there, so I fucked harder than ever, made a lot of noise, jerked about a bit, and pretended that I'd cum. When I pulled out, I could tell that he really wanted to see, and perhaps play with, my ejaculate, so I quickly pulled the condom off and dropped it where he couldn't see it. I honestly can't remember whether I got him off, but I suspect that I didn't. He seemed happy though, or at least he volunteered that he didn't live far away and asked whether he could call me again. I know I should have said no, but I figured I'd just say OK and then explain what the deal is if he ever emails me again. With any luck, he won't.