I put an ad on craigslist yesterday. I still had a slightly bruised ego from Sunday, and I wanted to play with someone I hadn't fucked before. I got the usual range of promising and unpromising replies, including this one:
Virgin bottom here would like to find out what penetration is all about; you look like a fine specimen: could suck you long before you plug me.
There was a picture attached, and, frankly, the picture was a bit scary, but scary in an I'm-trying-to-get-a-sexy-picture-for-craigslist-hookups-and-I-have-no-idea-that-an-overly-excited-smile-and-bad-flash-is-really-not-the-way-to-go sort of way. The guy was clearly fit, and I figured his total lack of lips was an artifact of the flash. Plus, there was something about his reply that hinted of articulacy, or at least intelligence. On the other hand, there was much about his reply that hinted of naivete. A two-edged sword: on the one hand, I absolutely believed that he was a virgin; on the other, a guy who doesn't understand that the thick cock he wants to suck on might have some trouble penetrating a virgin ass has potential for difficulty. So while I was intrigued, I figured that I should also educate him, so I wrote back:
I'm not opposed, as a matter of principle, to fucking a virgin ass, but I do have a very thick cock, so I want you to know what you're getting yourself into. I take plenty of time preparing an ass for penetration, whether it's virgin or not, and I do like it when a guy goes down on me while I'm getting him ready.
I also asked for a few particulars, which he had failed to supply. His rejoinder:
Thanks for your cordial reply and the warning of thikness. To be honest, this is my greatest fear: being torn a new one.
[The exurb where I live] is convenient and as I am "in-between contracts" can be available any time. I'm a young 55 and that is a recent picture. Kissing and touching is a real turn on.
Do you think less of me, readers, because I am willing to entertain men who have severe problems with both spelling and subject-verb agreement? I know I do, but I try to keep my priorities in line. In any case, I explained, in my next reply, that "torn a new one" is almost always used metaphorically and that injury only occurs when someone's doing something very wrong. Then I talked about lube. In his next email, he quoted Zappa: "keep it greasy so it goes down easy," and I was determined to have him. Any man who loves Zappa is going to be great in the sack. We exchanged a few more emails and arranged for him to show up at my place at 8.
As often happens, I stayed at the office a bit longer than I'd intended, and I had to rush to make it home in time to shower and dress again. It is one of the unfortunate facts of my life that I'm very much a grower rather than a shower, so I am never naked when I greet my intimate guests. In fact, I always make them wait a while before removing my pants and then a while longer before removing my shorts. I'm usually stiff soon after we start kissing, but making them wait makes sure that they don't see my cock until it's at its most impressive. Call me vain, but it also helps to assert that I'm the one who's leading the session. Anyway, I had only barely gotten dressed when the doorbell rang, and I went downstairs to let Stan in.
As I'd expected, his picture didn't do him justice. He was entirely nice looking and had real lips. They were almost plump, even. Naturally, I kissed him immediately, which took him back a bit. "Wow, soft lips," he said as he pulled away. I think he needed a moment to regroup, so he bent down to untie and remove his shoes. I went along, and we had about seven seconds of small talk while he was bent over. I may have groped his behind, but that was just me being friendly. I pointed him up the stairs, and as he commented on the neighborhood, I squeezed his buttocks. One at a time, alternately: I didn't want to scare him.
He mentioned, as he got to the landing, that because my ad had said that I was 420-friendly but didn't have any, he'd brought some along. [Remember back in December when I said what that bringing wine as a gift for the host displays a regrettable lack of imagination? I've decided that bringing weed is perfectly appropriate.] I started to remove his jacket, and he said that the weed was in there, but I told him that we'd get to it in time, and then I kissed him again and eased him toward and then onto the bed. I wanted to shove him the way I do with most guys, but I figured I should just go easy, at least at the start.
So let me just get this out of the way instead of referring to it again and again and again. Virgins come in two varieties: those who are so scared that they can't properly enjoy it, and those who are like newly plowed fields [you know, the comparison that I want to use here is to C.S. Lewis' The Magician's Nephew, where Narnia is a brand new world, and if you drop something on the ground, it'll take root and grow, but if someone is ever searching for the Chronicles of Narnia and sex and is hoping to find hott nude Tilda-Swinton-as-Jadis pictures and finds this post instead, I will feel really, really bad. Or not.] and are extremely open to and appreciative of everything you do. Stan was the latter, and his openness and appreciation were expressed very loudly. So you just have to keep in mind that most of the following two-and-a-half hours were played at a very healthy volume. It was one of those times when I was really glad to live in a single-family home: in an apartment or townhouse, I'm afraid that the name of the blog would have been rather too literal.
Anyway, I got him on his back and got on top of him and resumed kissing him. He was a pretty good kisser, especially if you allow for the difficulty of kissing someone who's constantly uttering something between a moan and a scream. I slid my hand up under his sweater and shirt and started in on his nipples, which, the evidence suggests, no one had ever done before. After a while I started working on them with my tongue and then just a very little bit with my teeth. After maybe fifteen minutes of working him at a three or maybe a four on the nipple scale, he said something about either "near torture" or "dear torture," but it was kind of hard to tell: his articulacy goes right out the window when you work on his nipples, apparently. In any case, he didn't ask me to stop, and I really didn't think I was being rough with them, so I kept it up until he'd been writhing and screaming for a good while. As soon as I stopped, he started telling me how great it had been, and I suggested that we try some of his weed.
Since this was only the second time I've smoked pot, you'll have to forgive my total ignorance, but he produced a pipe that looked like an ordinary tobacco pipe in miniature, and he said something about being near the bottom of the bowl and how I probably deserved a fresh bowl, but it all went over my head. In any case, I got about 1.5 good inhalations before he said that it was exhausted. Thank God (and some vocal training, probably) that I didn't embarrass myself by coughing. He didn't offer to refill the bowl, but I think that was because he was rather eager to get back to the sex. In any case, I probably got something from the weed -- it's hard to tell, I guess, when you're having such a great time anyway -- but I never got that giddy, baked feeling that I'd gotten the last time.
Stan got naked before he came back to the bed. He has a nice body: fair and mostly smooth, with just a small patch of barely visible hair in the middle of his chest. I went back to the lips and nips, of course, and he started to grope my crotch. I got him back to the point of shaking all over, and after a while more of that, he said he really wanted to play with my cock, so I pulled off my pants and boxers and let him have to. His technique is not quite there, but he was very eager, so it was all good. After a while longer, I pulled him back for some more making out. When he begged to back to my cock again, I told him that would only work if I could play with his ass. So he straddled my chest, facing south, and bent down to suck on me some more, and I spread his ass cheeks and dove in. Usually this is where a guy starts to shake and moan, but since Stan was shaking and moaning just from going down on me, the difference wasn't as noticeable. Still, he was obviously having a good time.
We were probably about an hour in when I started rimming him. After a bit more of that, I wet a finger and stuck it in and started to massage his prostate. He was, fortunately, extremely clean. I would have taken more time with that, but his cocksucking was more energetic than controlled, and my cockhead was starting to feel just a tiny bit sore. After exploring with different, but still single, fingers, I went for a second finger, and it seemed okay. But after a few minutes of that, he pulled off me and said that he was worried about taking my cock because the fingers made him "feel a little raw." I explained that I hadn't used any lube yet because I was still eating his ass, but that the lube would help. So I got it out, and, using a healthy amount of it, I got one, then two, then three, then four fingers into him. I managed to twist my fingers around while they were inside, and he was really getting into it. When I told him that if he could take four fingers, he could take my cock, he was eager to try, so I handed him the condom, and he unwrapped it and put it on me.
The thing I hate about lube is that when you go from fingers to cock, it's not so easy to get your hands de-lubed so that you can go back to working on the guy's nipples or any other place that you're eventually going to want to put your mouth again. But I wiped myself pretty clean on a pillowcase and my thigh, so that when he started to lower himself onto my cock, I could lightly twist both nipples and enjoy it. Stan sat down on me like a champ, and before long he was bobbing up and down and really getting an idea for what penetration is all about. After a few minutes of that, I tried lowering him to the X position, but I popped out of him when he moved too far away, so I got on my knees and pushed his knees up to his chest to take him face to face. He was obviously into it, and we were both well lubed, so I fucked him pretty hard. And it just went on like that for maybe another fifteen minutes. I had to keep asking him whether he was okay because, even just lying there, he was working so hard with all the writhing and screaming and what not.
Anyway, I figured a breather was in order, so I pulled out and we lay next to each other with me nuzzling his nipple. I told him that I was very impressed with any man who had the ability to carry on a conversation while I was working on his nipple, and he laughed, and we started to talk. I asked him what his deal was: it was obvious to me that he was a virgin, but he was such a natural and enjoyed it so much that I wondered why he'd never done it before. "Either you were married or you were in the priesthood. Or you were in prison, but then you'd know all about buttsex." He said that none of the above applied, and that he'd always been straight and was probably still bisexual, but he'd seen some gay porn and really wanted to try it and that if he could find a woman to treat him the way I'd treated him, he'd be a happy man. "Buy here a strap-on, Stan." Then there was some discussion of favorite authors and transcendentalism and ineffability, and then he was on his feet saying, "TED, I think we should call this our first time." And I was thinking, well, hell, we could hardly call it our second time, but he continued with "You've exhausted me."
As if. I pulled him back onto the bed and asked him whether he had a plane to catch. He said he was free, so I told him to just lie back. He said that he'd very nearly ejaculated while I was fucking and wondered whether it was possible to have an orgasm without ejaculating, and I told him that it was, but that I thought there was more to come. It was obvious that he was slightly upset because both of us were flaccid, but, geez, I'd been hard for an hour and a half. What am I, sixteen? And then there was this exchange.
STAN: This was the best sex I've ever had.
TED: Dude, you're a virgin. You've never been fucked. You've probably given like three blowjobs before you met me, right?
STAN: Yeah. How did you know?
TED: Educated guess. I appreciate the praise, but the bar hasn't been set very high, has it?
STAN: No, I mean it was amazing. It was even better than any sex I've had with a woman.
TED: Oh, please. Like women are any good at sex. But thanks. My first experience with a guy was truly memorable, so I do what I can with inexperienced guys. And you were great, too.
STAN: You're not bored?
TED: Oh hell no.
STAN: But you're all soft, and you didn't shoot.
TED: I know you won't believe this, but I have pretty much managed to make sex and ejaculation independent phenomena. You, however, are not so evolved.
And then I took his frenulum between my thumb and forefinger and rubbed them together until he was hard and inarticulate again. That took about fifteen seconds, and then I spent the next twenty minutes alternating between kissing him and sucking on his nipples while I stroked him and going down on him. He had a nice thin cock, so it was pretty easy for me to take (especially for forty-five seconds at a go), and he was very appreciative. Eventually, he told me that if I didn't stop what I was doing (at the time, I had one of his nipples between my teeth and was giving his cock full-length strokes), he would cum soon.
I didn't stop what I was doing, and he came. I held him for a bit and we talked some more. That was mostly more of him telling me how good I was. I generally find that sort of praise tedious, but I was feeling extremely content and mellow, so I kissed him a few more times then got up to get a towel to wipe up his semen. He sat up and leaned against me, and I ran my hands across his chest and back. He got up and put on his underwear and then sat back down. I explained to him that when I'm in a mood like I was then, I won't stop touching a guy and that he was welcome to stay and be touched for as long as he liked, that it was equally cool if he was ready to leave, but that he shouldn't expect me to stop playing with him while he was within arm's reach. He got up again and put on his shirt and then sat back down and leaned against me again, so I pulled him down for another kiss.
We went through the same steps with his sweater and then his pants, and then he thanked me again (and again) and I walked him to the front door. He said that he wanted to play again. I told him that he was more than welcome to play again but that if, upon further reflection, he didn't, I would not feel bad. I'd certainly do him again at any opportunity, but he's at a point in his sexual development where things are changing very rapidly, and guys like that often decide not to go for a repeat, for varied and often unclear reasons. I don't know whether I'll hear from him again (But it was the best sex I've had this year, and if it hadn't been for the truly stellar romp I had just before the new year, it would probably be the best sex I've had in months.), but it is really better to be grateful for the fantastic sex you did have than to regret the additional fantastic sex you thought you might have, but didn't. If you replace "fantastic sex" with "joy," then you have some very good words to live by. The world would be a much happier place if everyone did that.