MIRROR: Download from MEGA
We get lots of questions about anal play for beginners, so here's some basics. I'm a gay man who has done a fair amount of anal sex, both as bottom and more recently as top, so I know whereof I speak. But this post is not all there is to know about anal sex, so do some more reading online after this.
First, for all you victims of abstinence-only education, anal sex is sex. If you're having anal sex, you're having sex, and you're not a virgin any more. Get over it. And if you think God is going to be mad at you for having sex, He's going to be just as mad at you for taking it up the ass as He would be if you were doing baby-making sex. (Personally, as a Christian, I don't think God hates sex at all, but your mileage may vary.)
Some terminology: the anus is the external opening of the rectum, which connects to the small colon. The muscle that controls the anus is the sphincter. It is designed to hold feces in until the person is ready to defecate, so the sphincter is very good at holding things in, but not very good about preventing things from coming in the other way. The prostate is a gland that surrounds the urethra; it contributes to semen. In men, the prostate lies just on the other side of the rectum, so that when a man is getting fucked anally, the prostate is getting stroked indirectly. This is extremely pleasurable. In women, the prostate glands are not accessible this way (so anal sex is not as intensely pleasurable for women as for men, at least not biologically).
Before you do anal sex, spend a little time just exploring your anus with your finger. Take a shower or bath with warm water, wash your butt, and just explore a little. Most people are taught to associate the anus with filth, so it will help to spend some time exploring it as a center of pleasure. I find that the sensation of warm to hot water running over my anus is very nice; I often linger in the shower to feel it for a few seconds. Gently push your finger into the anus until you meet resistance from the sphincter; it might open in a few moments to let your finger in, but don't press hard. This is a fact-finding mission.
You can also have a partner rim your anus, licking it with a variety of strokes. Make sure it's clean, and if you're going to be getting rimmed a lot, your partner should get hepetitis A and B shots; hep is very nasty, and largely incurable, but there are vaccines against it. If you tell your doctor that you're doing rimming or anal sex and your doctor thinks hep shots are unnecessary, he's wrong (and not familiar with gay men's health issues); contact a gay men's health organization (even if you're a straight woman) and you can probably get the shots free or very cheap. The bottom is not really at risk of getting hep (unless the top is doing anal sex with multiple partners), but the top can be (since he's coming into contact with the bottom's rectum).
Once you're ready to stick something up your butt, set aside some time. Don't rush this. There are only three things that should ever go in your ass: 1) a clean, well-manicured finger (no long nails) or hand (if you want to explore fisting) 2) a human cock (humans only; animal cocks can really damage the human anus) 3) a purpose-made toy like a dildo, butt plug or vibrator. Do not use soda bottles, carrots, plungers, bike handles, small rodents, or anything else; there are all sorts of hazards that can happen. Veggies can break off, bike handles can go all the way in and get lost, plunger handles and broom sticks can splinter, rodents will bite and claw, and so on. Yes, you may have seen porn in which stunt bottoms take broom handles, night sticks, boot heels or toes, back hoes and what not, but you're not a stunt bottom; you're a beginner and you can't see what sort of precautions the porn shot took. If you use a dildo or vibrator, it needs to be one that flares out at the bottom, to prevent the whole toy from sliding in (which can happen very easily once you're using lube).
Once you've chosen your toy (and I recommend starting with a modest-sized dildo or butt plug, not a cock), use lots of silicone or water-based lube (don't use spit--it's not slick enough; don't use crisco or vegetable oil either, especially if you're using a condom, since oil dissolves latex). Clean the toy with hot soapy water, dry it, lube it up very generously, and very gently start pressing against the anus. In a few seconds, you will feel some discomfort; this is the sphincter struggling to keep the toy out. DON'T push hard; just keep the gentle pressure up and after a minute, the sphincter will tire out and relax enough for the toy to enter. The sphincter just isn't strong enough to resist a determined assault, but if you push hard you risk tearing the muscle and that would suck. You can usually tell when the sphincter relaxes, because the toy suddenly slides in. Success! Take a little time to get used to the new sensation of fullness. It may feel like you have to defecate; that's because you've never had fullness down there without needing to poop. After you get used to the feeling, start gently sliding the toy in and out. The first time or so that you do this, you may not enjoy it very much; your ass isn't used to this, you might be freaking out a little, and your sphincter probably hurts. Wait a day or two and try it again. If after several sessions you haven't started to find it pleasurable, then maybe anal sex isn't for you. But if you do find you enjoy it, do a few more sessions with toys and then use your partner's cock.
I'm going to assume your partner is monogamous with you; if not, ALWAYS use a condom. The pleasure of butt sex is not worth the risk of AIDS. For your first session with a real cock, I recommend that your partner lie on his back and that you straddle him and slowly lower yourself onto his cock. This gives you near total control over how fast you go. Every time you fuck, your sphincter is going to take a minute to loosen up, so the bottom needs to start out with control (or else loosen your sphincter up with a toy or fingers). Once your feel the head of the cock slide in, you can finish lowering yourself onto your partner's cock, and after a few moments, he can start to thrust gently or you can slide up and down on the cock. After doing it that way for a little bit, change positions and let the top start having his fun. (It's possible to be submissive when you're on top like that, but most other positions feel much more submissive than this one).
So that's the basics on anal sex. Let's talk about a few complications. First, there is shit. You probably have some in your ass. Anal douching/enemas are not absolutely necessary for anal sex, but they make it much cleaner. So consider taking a quick enema or a dump before anal sex; it sharply reduces the risk of an unpleasant accident that will completely kill the mood (there's still one guy I cannot imagine fucking again, even though he's cute, simply because things got messy). Even if you douche, there might be a little bit of poop on your toy or cock when it comes out. That's unavoidable unless you do what porn stars do when they're going to get fucked (which is not eat for a while beforehand and aggressively enema--remember, porn doesn't usually show the precautions). If you're going to do anal sex, you just need to accept that you will occasionally see a trace of brown (if that grosses you out, wear a condom). Having said all that, I never douched when I was bottoming, and I never had an accident.
After anal sex, you may very well have the urge to defecate. That's natural; you've just loosened the thing designed to hold shit in, and vigorous thrusting may have softened up the stool inside you; the lube may also make keeping stuff in harder. So plan to make a quick run to the bathroom when you feel that urge. But there is little evidence that anal sex will lead to incontinence. Like all muscles, the sphincter gets stronger when it's exercised, not weaker. Wash your butt and the top's cock after sex, because you might have a little santorum. Feces aren't a contact poison, so a little on your skin will not make your sick, but if it gets into a rash, open cut, or sore, you could wind up with an infection.
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