Hot Monday

So: Monday. It was Monday, and I was supposed to hook up with Vim, the super-cute young Black guy whom I'd met on Friday in a somewhat truncated hook-up. I'd said around 7 but that I'd call first, and when I called at 6:15, he said he was in the middle of his commute and that he wouldn't be home by then, and could we do it later, like possibly 7:30. Or ish. And that was cool with me, but then maybe five minutes later, he called again and said that he had to pick up something for his mother, but that he'd be home and available by 9:15, if I wanted to play, and I really didn't fancy going down to Fort Totten that late on a Monday night. It would surely mean not getting home before midnight.

I decided not to invest the intellectual and/or emotional energy necessary to assess whether Vim was playing games with me. He'd seemed sincere, and after a very brief discussion, the upshot had been him saying that he'd see me Tuesday night. I headed home, thinking that maybe it was a good night to get caught up on housework or read a book and go to bed early, but as soon as I sat down at the computer to check email, I felt the urge to at least put some lines in the water. I sent a text message to Gil. Gil is a local submissive whom I still haven't met. If we can ever align our schedules, then I'm thinking he may turn out to be a great fuckbuddy for occasional rough dom/sub play, but a) that may require an upgrade on my bed frame, and b) I'm not sure I'm ever going to see any return on the (admittedly small) investment that I've already put into the Gil project. Not surprisingly, when I was posting a craigslist ad (and, to be honest, I was posting it without much conviction) and checking out some other sites, Gil texted back to say that he wasn't available. Or, in his words:

ted amd riving back from kent county. guys from work in truck w me. cant talk but xox work me in later this week? ?

A book and bed was looking pretty good.


I got a message, on a site that specializes in the over-forty crowd, from a guy who's screen name included something very similar to "CDLucy," and I thought, a) oh hell no, b) why do so many cross-dressers self-identify as Lucy? c) he does not make an attractive woman, d) does it have something to do with Lucy Van Pelt? e) Joe Lieberman is really a douchebag, and f) sigh. The sigh being my politeness kicking in. I hate to leave even the most inappropriate of offers unrespondedto, so I sent a message thanking Ms. Van Pelt for her offer, but telling her that I am really not into cross-dressers. The bed and book stock continued to rise.

After rejecting a couple of unpromising responses to my CL ad, I saw that Lucy had sent me another message, wherein he informed me that a) he was travelling and so did not have his lady clothes with him, b) he could not, in any event, pass as a woman, and c) he really, really liked to kiss. So I checked the stats, which all looked good, and called the phone number he'd left. He sounded like a pretty cool guy, and he was staying at a hotel that is only a short drive from my house, so I said I could come over, and he gave me the room number.


Jon, as we must now called him, answered the door wearing only a pair of jeans, and it was a very good choice. It's always one of my favorite looks, and his were just loose enough to show off a tan line and a hint of asscrack, and, as is so often the case, I could not -- and, in fact, did not -- resist the urge to grab him and kiss him. Yum. I did not stop kissing him, but I did make a mental note that most men do look much better as men. And then I made a second mental note to the effect of but I don't judge. It is not the first time that I have made either of those mental notes, but some things bear repeating, particularly if you can repeat them mentally without stopping the lip locking action.

I worked on Jon's nipples some, but I concentrated on the kissing for a while, throwing in the occasional wrist-grab-and-pin-over-his-head combo which drives a lot of the bottoms, especially the sub or semi-sub ones, wild. We had gotten a bit of a late start for a Monday, and I figured he was in something of a hurry when he rushed to get my pants off and go down on me. He murmured something about how he hadn't had a cock in a while and something else about how big mine was, but he had pretty good fellatory technique, so I didn't listen all that closely. I did, after a while, pull him up and start kissing him again, and we went through three rounds of the make out/blow job tango before I pulled his legs around so that I could eat his ass.

He'd been somewhat reserved (though he certainly didn't complain) when I'd worked on his nipples, but the reserve evaporated when I went in for the ass eat. Fortunately, he didn't let it get in the way of sucking my cock, so I kept at it for a while. We were on our second go-round of that when he opined that he had never taken a cock as thick as mine, but that he would certainly like to try.


Can I just say that I've been through this all many times, and it always sounds the same from both the other guy and from me. My contribution typically consists of "hmmm" and "yeah" and "relax," and the other guy's dialog is always something along the lines of "Oh, I want that cock. Oh it's so thick I'm not sure I can take it. Uhhhh. Go slow. Slow. I can't take it. I want to, but I just can't. Slow, please. Ohhhhhhhhh. Ohhhhhhhh. Ohhhhhhhh. Yeah, fuck me. Fuck me. FUCK ME!

It's always exactly the same.

And it never gets old.

Anyway, for someone who wasn't going to be able to take my cock, Jon certainly took a hard plowing in a number of positions. He was really tight, though, and I came while I was fucking him. I used to say that almost never happens, but looking back, it seems like it happens nearly one-fifth of the time. Anyway, I was feeling terrific, and he seemed not to need anything else, but I kept kissing him and working his nipples, harder now and with more positive feedback, and eventually he started stroking himself, and he came with an impressive amount of intensity.

And then it was late and he said that he had an early meeting in the morning, so I got dressed and he told me that he's in construction management and will be back in the area in a week to do an inspection of a site and really wants me to fuck him again. He also told me that he never travels with his CD paraphernalia because he doesn't want to be embarrassed if airport security finds it. It seemed to me that that problem could be easily dealt with, but I didn't particularly want to encourage him to bring back women's clothing when he returns to town. It would turn me off; besides, he would make one hell of an ugly woman.