Super cute Boston blogger Sean (I think he's a BU student; I probably could have seen his dorm from my dorm room window across the river, give or take twenty years) has a problem: he's a lousy top. I kid: the real problem is his bf (Who, I believe, is a student at Northwestern, where I got my master's degree. Everybody sing: "It's a small world after all.") is a lousy bottom. No, I'm kidding again. The real problem is that
I was also going to give Tommy some credit for being willing to take the pain in order to please his man, but really, that's just whack. Authorities differ over whether some level of pain is inevitable in anal sex, but if after several tries you're gritting your teeth and bearing it just because you're head over heels (and, as it happens, heels over head) for your man, you need to reassess your priorities as well as your guy's technique.
But I'm not here to judge. I'm here to solve a problem. Not, mind you, that anyone asked me, but having introduced my share of virgins to the glories of anal sex, I'm pretty well qualified to offer advice on this particular subject, and, hell, what would the Internet be without unsolicited advice? Weather updates, pretty much.
Anyway, the key to successful buttfucking is pretty straightforward: relaxation. A guy who's worried about how much his partner's cock is going to hurt is going to experience a lot more pain than a guy who's relaxed and anticipating great pleasure. On the (blessedly rare) occasions where I haven't been able to make anal sex work with a would-be bottom, the problem has always been that the guy can't relax. Typically, he feels the cock coming, and he's afraid he can't take it, so he tenses up, and then he can't take it. It is possible, with enough lube and diffidence, to force yourself into an unwilling orifice, but it's wrong, and it's counterproductive. I reckon there are some guys for whom the physiological sensation of shoving their cock in and out of a very tight hole is enough, but for most of us, the sex is going to be an order of magnitude or two better if the guy is begging for more rather than begging you to stop. (Unless the guy gets off on begging you to stop, but that only works if you know in advance that it's going to happen. Besides, in those cases begging you to stop is really begging for more.)
Relaxation is something that you have to tackle on multiple fronts. Yeah, you gotta get the ass to open up, but throwing more lube at the situation (while important -- we love lube) is not enough. This is especially true in Sean's situation, where he's dealing with his main man, rather than with some random guy who answered his Craigslist ad.
(The approach I'm recommending in Sean's case is specific to situations like his: two guys who are already attracted to each other but are just having trouble making anal work. For obvious reasons, I'm not called upon to use this approach very often. I typically have two hours/one session to break in a new virgin, so I have to combine a lot of this into a single encounter. Dildos help.)
You begin the longer term preparation for buttsex by ignoring buttsex. There's a widespread perception, among both gays and breeders, that the only so-called real gay sex is anal intercourse. This is a misguided attitude for all sorts of reasons, beginning with the fact that if the only thing you're interested in getting to is the fucking, then you miss out on many, many things that can be at least as much fun. More to the point, if you're convinced that you're not really having sex if you're not fucking, you make fucking such a big deal that you increase the stakes and make it that much more difficult to relax.
So part one of Sean's strategy ought to be to experiment with other things. I'm pretty sure that he and Tommy have making out covered, but that still leaves a lot of erotic ground uncultivated. He might want to consider, just as an example, turning the heat up (literally) in his room and having the two of them sit at opposite ends of the bed while they slowly masturbate and tell each other about experiences they had before they met. The goal is to shoot at the same time. Or Sean might have Tommy close his eyes and lie on the bed while Sean slowly explores the entirety of Tommy's body, using only the tips of his fingers and tongue. This last activity works even better if both of them keep their underwear on. The particulars don't matter so much. What matters is an expanding understanding that anal sex is just one of the items on a very large menu.
Once the general relaxation is working, it's time to get going on the specific anal relaxation. Here again, long and slow preparation is the key. Anal play is, or at least should be, very hot stuff, but if you rush into it and make it all about intercourse, you run the risk of losing much of the eroticism. Before you can get to the pounding (and, let me reiterate that I am very much pro-pounding), you have to get to the point where the guy who's going to get pounded thinks of his ass as a highly sexual organ. I think there are two main tools to get this idea across to the potential bottom: rimming and massage. And, really, you want to use both of them, though it's not always practical to use both in the same session.
In either case, there are some necessary preliminaries. First, you need to make it clear in advance that there's not going to be any intercourse in the initial session. This is about eroticizing the anus, not about fucking. At least not yet. Then -- and this is always the case with any form of anal sex -- you need to make sure that the top's fingernails are cut close and filed smooth. Finally, everyone needs to be confident about the bottoms cleanliness. If at all possible, you want the session to start with a lengthy, steamy, soapy shower. Which, really, is so much fun that you ought to be doing that together all the time, anyway.
Now let's say that rimming is your approach. You've got your two guys who are scrubbed cleaned and relaxed from a hot shower. You make your way back to the bed, and you make out for a while and do whatever other sort of foreplay you like. Then you have the (would-be) bottom lie on his chest, and the top slowly kisses, nibbles, licks his way down the bottom's back. At the same time, he runs his hands slowly up the backs of the bottom's thighs and begins to spread the asscheeks. And then he licks. Slowly and very gently at first, and paying extremely close attention to the bottom's reactions. Eventually, the top can get more intent and hungry and can throw in some fingering, can spread the cheeks wider, can get the tongue in deeper, all to drive the bottom wild.
It's no secret that I love to eat ass. If you're squeamish and so have never tried it, you really need to get a nice clean ass and dive in. For guys who still have a problem with it, you might find it more palatable and fun if the guy whose ass you're eating is going down on you at the same time. With that approach, it's pretty simple: while the guy's got your cock in his mouth and/or throat, you pull his legs around and you slide around until you're in a position to get between his knees. Then you get between his knees, spread his cheeks wide, and begin to lick. Be prepared, though. Guys who haven't been rimmed before can find the sensation overwhelming and may suddenly forget to suck your cock. If that makes it harder for you to eat his ass, gently (or not so gently) ask him to continue sucking your cock. Then continue eating his ass. When you've been at it for a good long time and you're both really worked up, jerk each other off.
Massage is somewhat different, of course. You'll need (in addition to your carefully trimmed nails and your steamy shower) a bottle of baby oil, which you should warm. Put your man face down on the bed and get to work. Squirt a little bit of oil on him and begin by rubbing his neck and shoulders. You don't want to rush this part: you're trying to make the guy as relaxed as possible. Besides, it's fun. You can both be naked, and you can straddle his ass to increase the physical intimacy, but mostly you want to just work his muscles for a while. When you feel a particular muscle relax under your ministrations, move down. On your first pass down, you'll want to work the glutes, but not get to close to the asshole. Work the thighs, calves, and -- especially -- feet first. Then as you're working your way back up the body, it's time to concentrate more closely on the ass. Dribble plenty of oil into the hollow at the top of the cleft of the buttocks and let it trickle down across the asshole. Lightly spread the cheeks and let your oily fingers slide back and forth across the asshole.
When the bottom is nice and relaxed, then it's time to let a very oily finger gently penetrate his ass. Go slow, go slow, go slow. And use your other hand to massage his shoulders, back, glutes, whatever, to keep him nice and relaxed. With enough oil and patience, an index finger will always make its way into the ass. Your goal here is the prostate, which you are going to stimulate very lightly with a fingertip. Work your way around the periphery of the prostate before pressing gently on the middle of the button, then play with the outside some more. Again, pay careful attention to the bottom's reaction and continue to use your other hand to keep him relaxed. With any luck, you'll be rewarded with hard breathing and precum. Eventually, you should be able to get a second oily finger inside your guy, and then you should outline the prostate with both fingers, one taking either side.
When you've got him good and worked, very slowly remove the fingers from the ass, give the back and shoulders another minute or two of rubbing, then flip your buddy over and finish him off: work on his pecs and the fronts of his legs, then oil up his cock and make him shoot.
The goal of both rimming and massage is to make it clear to the guy you want to pound that his anus and prostate can be sources of great pleasure. Once he figures out how awesome it can be to have his asshole and prostate stimulated, he should be ready to relax and enjoy the more intense stimulation that a cock can provide. When he decides that he's really ready to try the cock, you'll want to start again with a shower (actually, you'll probably want to start with some booze, but we here at The Neighbors Will Hear do NOT condone underage drinking, so we really can't tell Sean that having Tommy pound a few shots before they head into the shower is really the way to go), then lots of foreplay, and then some oil-free massage and some rimming to get his ass nice and hungry. Then you get the lube and start in with a finger, then two, and then maybe three or even four, depending on how thick your cock is.
When you're learning to fuck, I think that face-to-face is the way to go. It's more intimate, and you're in a better position to know just how slow you have to go. If you've been kissing while you've been sliding your finger(s) inside your guy, you'll be in the best position to ask him if he's ready to try. Or to wait for him to tell you he's ready. Either way, you have to remember to let him set the pace. Put the condom on, make sure that there's plenty of lube both on it and on his ass, and then get ready for entry.
You have two good options here. Either he's on his back and you push his knees forward and get his ankles over your shoulders and you enter him that way, or you have him sit on you. The advantage of having him on his back is that you can get your face pretty close to his when you're starting to fuck him, and that increases the intimacy and can make him more comfortable. The advantage of having him sit on you is that he has total control over the pace of penetration. Pick one and try it, keeping in mind the other as a fallback position.
In either case, let penetration proceed very slowly. Some bottoms find it easier to get used to the cock if, once the head is inside, they push back against the cock for a time. It helps, obviously, if the top remains calm and looks like he's having the best time ever. When your cock is most or all of the way inside your partner's ass, wait for a while and play gently with other parts of his body until he relaxes fully. Then you can start with some slow and easy in and out. If the guy's on his back, and he's relatively flexible, you'll find that the more pretzeled he is (i.e., you want his ankles behind his ears), the better an angle you'll get on his prostate, and the more intense he'll find the sensation. Continue to accelerate and deepen your thrusts, but don't overdo it, especially the first couple of times you fuck him. A little soreness the next day is fine and hard to avoid, but you don't want to leave him feeling used. Just fucked.
Finally, a warning. Once he's used to (or both of you are used to) getting fucked, make sure you continue to do other things. Yeah, it's intimate, and yeah, he might love it, but eventually you'll get bored of a guy who sees you and immediately wants to bend over and take it. This is a serious risk with a guy who first discovers the joy of being fucked. For a lot of men, it's so much more intense than other activities they're used to that they lose interest in anything else.