How to Buttsex Someone Up But Good
1. Make sure your butt-buddy wants it. Really wants it. If you're doing this to widen their perspective on masculinity or femininity or sexuality, that's the wrong reason. If you're doing this to prove something or score some sort of points, that's a really wrong reason. Do it because they and their butt want it. Ask them how they want it and prioritize that above anything I say here.
(Special note to cis men who have never "pitched" in anal sex: from what I hear, it's not transcendently pleasurable for a penis. It's fun, sure, but it's not like a magical penis-amazing wonder above all wonders. It feels like PIV intercourse only sort of different. It will not bring you some ultra-mega-tight satisfaction that a vagina never could. So control your expectations here, and if your partner isn't up for it, don't think you're missing out on the best thing ever.)
2. Make sure you're up for it. Just because you're the penetrating partner doesn't mean it's no big deal for you and you have no basis to object. It's fine to be uncomfortable with the idea of penetrating someone anally, or to have reservations or specific wishes about how to do it. Just because you're not putting your ass on the line doesn't mean you don't get a say.
3. Be prepared for poop. You cannot have buttsex if you don't have some level of comfort with poop. It's usually not a lot, though; we're talking "smear" here, not "load." Even so--put down a towel. Put a glove on your hand and a condom on your dick or any toys. Have some wipey things available. There's no need for your partner to have an enema, but they probably shouldn't do this if they've got a poop on deck, if you know what I mean.
4. Be prepared for different reactions. For some people, it'll be "OH GOD YES OH GOD," for some it'll be "mmm nice," for some it'll be "no, take it out." People don't deal with anal stimulation in one way, especially if they're new to it. And the same person on different days doesn't deal with it the same way. Roll with however it goes.
5. Okay, let's do this thing! Let's start with... how about some kissing and cuddling, actually? Just because you're using a different hole doesn't mean you gotta be all brusque about it. Or some wrassling and spanking, if that's how you warm up. But when your fore is played, let's start with a finger. A finger with a glove on it, to spare you their butt-germs and to spare them your fingernail. Lube it up real good. You can't use too much lube. Spread it all over your finger and use as much as will stay on it. Put the pad of your finger on their anus, not pushing, just touching. Have your partner relax and breathe and when you feel their anus relax a little, just slowly slide your finger on in there.
You'll feel two separate sphincter muscles. The outer one is under voluntary control; the inner one isn't, at least not directly. If the inner one won't let you in, don't try to push through, just let your partner work on relaxing and opening up. (If it really won't let you in, your partner may just not be made for buttsex, at least not on that day.) Gently massaging it can help.
6. This is the awesome part. Or the start of the awesome part. People's butts are hot and smoothly soft inside and you can feel the tiniest contractions of their muscles. Despite all the warnings you hear about the rectum being fragile, it's also strong; it can grab your hand so hard you worry about yourself more than your partner. But the first thing you want to do after putting your finger in them, if they're new to this, is nothing. Don't get all thrusty. Give them a moment to adjust. Give yourself a moment to just enjoy it.
7a. If your partner is the sort of person who has a prostate, look for the prostate. (Well, don't look for it.) It's going to be on the front--i.e., crotchward--side of their rectum, about two inches in. (If they're Canadian or something it will be five centimeters in.) A finger slid in all the way and bent should just reach it. You feel it through the rectal wall, so it's sort of indirect, but you'll know it because:
A) It'll feel like a distinct bump about the size of a walnut, smooth and round.
B) Your partner is likely to go "OH MY GOD RIGHT THERE."
7b. There's two directions you can take this now. (There's infinity directions. I'll talk about two.) One is to continue on to the fuckin'. The other is to just focus on the prostate, because you can get a lot of people the hell off that way. Just keep rubbing it while you or your partner plays with their genitals, and it's likely to give them an incredibly powerful, I mean blasting orgasm. I mean, I once made a guy accidentally hit himself in the face this way and he didn't even notice for a little bit. Then he noticed and it was pretty amusing.
8. If you turned to page 238 to "continue on to the fuckin'," add another finger. Slowly, gently, and lubily. Pay attention to how they adjust to this--both in their anus and in their face. You can gently slide your fingers in and out all sensual-like, but unless your partner asks you to, don't start thrusting like you're trying to churn butter in there. Anuses aren't vaginas and it won't feel the same way that thrusting into a vagina does.
9. PENIS TIME! Or dildo time. Or, I'm not judging here, eggbeater time? Take your fingers out of your butt-buddy's butt. Put a condom and heaps and loads of lube on your implement of choice and do like you did with the fingers--just place it against their butt, and wait to feel them relax before pushing. And again, give them a moment to just adjust to you inside them before you start doing anything.
You will probably not hit the prostate directly with an average-size penis or equivalent toy. Maybe it'll get some driveby stimulation in some positions, but buttfucking isn't really prostate work. Not the way Step 7 is.
10. I think you know what to do now. But do it a bit less vigorously than you normally would. A lot of in-and-out isn't really how butts work. Unless your partner is encouraging you to do more, you want to err more toward the "sliding" than the "pounding" end of the scale here. Check in with them; they may not want you to thrust at all but just be happy with you in their ass. They may or may not want you to play with their genitals (or let them play with their own junk) while you're in there. They may be able to go the distance, or they may need you to stop after a bit; again, the only way to know is to check in with them and give them permission to tell you to stop.
11. Clean up (probably don't do this on white sheets) and give your partner a hug and tell them they're awesome.
SAFETY NOTES:
-If you're doing this with a bio-dick, use a condom even if you don't for vaginal sex. Butt-germs can get in your urethra.
-Blood and pain are not normal, even the first time. This isn't like losing your hymen; there's no reason the first time should hurt. (People seem to vary on whether it's okay for it to hurt a little bit. Personally I think it isn't, but at any rate any pain more than "a little bit" is too much. If you're gritting your teeth to get through it, you're getting hurt.)
-Lube lube lube lube lube. And then add more after you've been going for a bit. Butts not only don't make their own lube, they suck moisture out of the lube you put in them. Keep things messy wet.
-There are bacteria in the ass that can make you sick if they get in any non-ass body openings. Don't put anything that's been up someone's butt in anyone's mouth or vagina.
-Your butt-buddy is putting their ass in your hands. (And vice versa.) That's one hell of a gift. Treat it good.
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