How To Have Anal Sex: A Beginner’s Guide

Anal sex or anal intercourse is generally the insertion and thrusting of the erect penis into a person’s anus, or anus and rectum, for sexual pleasure. Other forms of anal sex include fingering, the use of sex toys for anal penetration, oral sex performed on the anus (anilingus), and pegging. Although the term anal sex most commonly means penile-anal penetration, sources sometimes use the term anal intercourse to refer exclusively to penile-anal penetration, and anal sex to refer to any form of anal sexual activity, especially between pairings as opposed to anal masturbation.”

Note: Since anal sex is gender-neutral, this blog will refer to the person doing the penetration as “The Top,” and the person being penetrated will be referred to as “The Bottom.”





Step 1: Communicate.

The first step towards having virgin anal sex with your partner is to talk to them about it. Never pressure anyone into doing anything they don’t want to. Just express your interest, and explain the benefits and the process. Create a plan and agree on your boundaries. The better they understand what they’re getting into, the fewer misconceptions they’ll have holding them back.


Step 2: Acclimate The Bottom’s mind and body.

If you don’t loosen the anus before penetration then you run a high risk of tearing the tissue. So you’ll want to loosen it with some light stretching before you penetrate it with your penis or strap-on. It’s a good idea to begin the process a few days before you do the real deed. Not only will this prepare the tissue for preparation, but it also acclimates your partner’s mind. It’s a natural reflex for the body to tense up when the anus is penetrated, and if you try to force your way through you increase your risk of tearing tissue. If The Bottom is already used to being penetrated, they’ll be more relaxed and more able to safely and enjoyably receive deeper penetration.

You’ll definitely want to loosen the anus immediately before penetration every time. You can use a finger for this, but if either of you has anxieties about poop, this could be a turn-off. You could wear a medical glove to keep from getting your fingers dirty, but some people may find still find that awkward. Also, many people have latex allergies. So you may want to use a non-latex glove just to be safe.

Your other option is to use a sex toy. There are a dizzying number of sex toys on the market. The most important thing you need to remember when picking an anal sex toy is that the anus tends to pucker when penetrated, which can suck toys into the anus resulting in an embarrassing trip to the E.R. to have it removed.

There are anal pros who will tell you that you can safely use vibrators and dildos for anal play, but most X-Ray technicians would advise you to only use toys that are designed not to get lost. The safest, simplest toy is a butt plug with a wide base. An added bonus to using a butt plug is that you can insert it and leave it there while you make out or have oral or PIV sex prior to anal penetration. Both partners can also wear a butt plug so that The Bottom doesn’t feel like the experience is one-sided. Not only is that a fair compromise, but it’s actually a great opportunity for both people because hey, anal penetration is fun.

Wearing a butt plug can give a man a higher-level orgasm, but he can get an even higher-level orgasm by having a vibrating prostate stimulator inserted in his anus. Again, make sure you use one with a wide base. If you give a man a blowjob while probing his anus with a vibrating prostate stimulator, he’ll have a mind-blowing orgasm, and it’ll be a great bonding/equalizing experience for both of you.

Whatever you stick into an anus, it’s absolutely vital to lubricate both the object and the anus first. You’ll want to use 5-10 times the amount of lube as you would use to lubricate a vagina. When in doubt, err on the side of caution. Nothing bad is going to happen from using too much lube, but you can easily create a worst-case scenario by using too little.

When lubricating the anus, the thing to remember is that, unlike the vagina, the anus doesn’t produce its own internal lubricant. So if you apply a generous amount of lube to the opening and the object, then stick it in, the object will slide in easily for an inch or so, but the lube will quickly rub off on the sides of the anal cavity, and then the dry object will hit dry tissue and tear it. So you want to lube the hole and the object, penetrate the anus a little bit. Then re-lube the opening and the object and penetrate it again. Then do that again. Keep in constant communication with your partner to determine how many times you have to repeat the process, and be prepared to re-apply even more lube at any time during anal play.

Not everyone wears a condom for anal sex, but until you’re in a long-term monogamous relationship with someone, you should, because it prevents the risk of STDs and UTIs. It defeats the purpose of having fun if it’s going to make you sick.

If you’re worried about poop, you can take a laxative or get an enema earlier in the day to clean out your colon prior to having your anus penetrated. Beware though, if you take laxatives or receive enemas too often, your body will become dependent on them, and then your life is going get a lot harder. The simplest thing you can do to keep your colon clean, is to eat plenty of fiber like Shredded Wheat. Just don’t eat too much fiber or you’ll get constipated.


Step 3: Lube up the anus.

There are tons of options available for anal lube. If you’re looking for the best anal lube for you and your partner, check review sites like Lubricant Reviews to see all of the options available. A good anal lube will usually be thicker than your standard lube and some of these products include a desensitizing agent that help numb the sphincter. Because of this numbing agent, you MUST be careful how fast you proceed in case your partner is not fully aware of any issues with unintentional tearing.




There’s no one right or best position for anal sex. They all have their pros and cons. The question is which position you and your partner most comfortable with and what mood you’re trying to set. Here’s a list of the pros/cons of the basic positions to help you figure out what’s best for you and your partner:


1: Normal doggy style

Of all the sex positions, doggy style is the most synonymous with anal sex for one good reason: It angles the anus perfectly to slide an object in comfortably (though other positions can be just as comfortable). It also allows The Bottom to play with their genitals while being pleasured from behind.

The downside of doggy style is that it’s the least intimate position. So if you’re doing anal for the first time, you might want to start in the doggy style position for a few minutes and then switch to a different position in which there’s no chance of The Bottom feeling like they’re being used as an impersonal fuck toy. Having said that, you should revisit the doggy style position when you’re both ready for hard, wild, uninhibited anal sex,


2: Laying on the stomach

Have The Bottom lay flat on their stomach (possibly with a pillow under their hips), and have The Top mount them. This is more relaxing for The Bottom than doggy style, it provides a good angle for penetration, and it allows The Top to hug and kiss The Bottom thus making anal sex a more intimate full body experience. The only problem is it’s difficult for The Bottom to pleasure themselves.


3: Spooning

Spooning gives you just as good of an angle for penetration as the previous two positions, and it allows for more intimacy. Plus, it gives The Bottom plenty of room to pleasure themselves with their hands or toys. The Top can even reach around and pleasure The Bottom’s genitals. This way, The Bottom isn’t just someone that anal sex is happening to, they’re the center of attention, and they have a good chance of having an orgasm (as long as their genitals are being stimulated while their anus is being penetrated).


4: Missionary

The missionary position is arguably the most intimate sexual position. It gives both partners the most room to kiss and use all their body parts to express their passion. If you put a pillow under The Bottom’s hips, they can be comfortably penetrated.  The Bottom has the freedom to relax on their back completely or take control of the speed and force of the thrusts. Both partners also have room to pleasure The Bottom’s genitals with their hands or toys. If your goal is to make your first anal sex session as romantic as possible, you may want to use the missionary position.


5: Cowgirl

The cowgirl position gives The Bottom more control over the speed and force of thrusts than any other position. So if you’re nervous about anal being too intense and damaging your bodily tissue, this might be a good position to start in. If The Top lays flat on their back, they may not get the intimacy they’re looking for. But if The Top sits on a chair or couch and has The Bottom straddle them while they’re sitting upright, then both partners can experience lots of intimacy, and if The Bottom is a female, she can rub her clit against The Top’s abdomen and possibly get an orgasm. If your main concern is that anal sex is as physically pleasurable for both partners, you might want to use this position.


6: Reverse Cowgirl

Everything I just said about the cowgirl position applies to the reverse cowgirl position. The two biggest differences are that if The Bottom is a female, she can’t rub her clit against The Top’s abdomen. However, if The Top is sitting upright, he/she can easily reach around and pleasure The Bottom’s genitals using hands or toys. So more than any other position, this gives a female Bottom the most potential to be the center of attention.




If you or your partner are nervous about anal sex, talk with each other about what speed/s you’re going to use ahead of time. The more everyone understands what they’re getting into, the less reason anyone will have to be anxious.


1: Slow

You definitely want to start out an anal sex session very slowly to give The Bottom’s mind and body time to acclimate. If it’s their first time, you might not even want to ever build up to medium or fast speeds. There’s nothing wrong with penetrating The Bottom and then holding your penis or strapon inside them without ever thrusting at all. This way you can use all your time together to focus on pleasuring The Bottom’s genitals while they’re statically/passively penetrated from behind. This will give them a safe, pleasurable, intimate experience that could wet their appetite for more vigorous anal play later on instead of shocking them and scaring them away from experimenting with anal in the future. Another option is to statically/passively penetrate them for a few minutes and then work your way up to slow, fluid pumps and stick with that pace for the rest of the session. This can make for a nice, soothing introduction to anal sex.


2: Medium

You always want to start an anal sex session with slow thrusts for the safety of The Bottom. However, if you only ever have slow anal sex, both partners will probably get bored eventually. It’s hard to go wrong with a nice, even medium pace. It allows both partners to feel what’s going on, and it’s probably not going to hurt anyone. Just make sure that your movements are fluid and everyone should have a good time.


3: Fast

For the safety of The Bottom, don’t start with fast thrusts. Start slow, then speed up to a medium pace. Stick with that for a little while, and then rev up your speed. Check with your partner first to see if they want you to be that aggressive, and make sure their anus still has plenty of lubrication. Fast anal sex can be great as long as everyone and everything is ready for it.




I’ve never heard a logical, coherent argument for why anal sex is immoral. Sure, it involves poop and the butt, but life involves poop and butts. Poop and butts is a mundane non-issue. There’s no reason for it to be a taboo. It’s just there. Actually, it’s better than just there. It’s a gift. It’s an opportunity for intimacy with the ones we care about. There is only good in that. If we’re not here to live and love, then what the hell are we doing here? I can’t, don’t and won’t believe that we’re here to fear and loathe any part of our bodies. I believe we’re here to live and love, and anal sex is one way of doing that.

Having said that, anal sex is not a moral imperative either. There’s no logical reason why anal abstinence would make you a bad person. Your prerogative is your choice, and your choice is your right. You do your thing and don’t let anyone pressure you into doing something you’re not comfortable with.


If you enjoyed this post, you’ll also like these:


Sex positions and techniques
General Sex Advice
Dating Advice
Relationship Advice
Philosophy of Sexuality
My Tweets About Romance

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