This is the censored version of this post on anal sex. You can view its uncensored version with sexually explicit (NSFW) photos on Pillowfort.

A cowboy dressed in pink and winking. Captions read, "This should be a gif of two guys fucking cowboy style. You get a pink cowboy instead."

Years ago, I was looking for a how-to on anal sex that was inclusive of bisexual, polysexual, and pansexual guys. I couldn’t find one, so I decided to make one—and Sex Ed for Bi Guys was born. Anal sex is just one of many sex acts guys can do together; many guys who sex other guys don’t do it all the time, or sometimes never do it at all. Some people can’t have enough of it though, and if it’s something you want to explore, here’s a tutorial on the thing.

I wrote this guide with in mind guys looking to have anal sex with another guy, whether this is your first time having penetrative sex with someone—no matter their gender—or not. But everyone’s got a butthole, so this guide will be useful no matter the gender of the people you’re thinking of having anal sex with.

A short anatomy lesson

Anatomical chart of a penis, testes, and prostate owner [NSFWish]

For penis/testes owners, someone penetrating your butt can feel great because your prostate is one of the most sensitive spots in your body. It’s a gland that produces some of the fluids that make up semen.

You can stimulate your prostate from inside your rectum; many people call it “the male G-spot” (not everyone who has a prostate is a man though). You can feel your partner’s prostate or your own when you insert a finger in the butthole, and feel around the cavity by pushing in the direction of the base of the penis. You don’t need a partner to enjoy that pleasure, and a lot of people play with their butthole and prostate when they jerk off.

Not all guys have a flesh-and-blood penis nor a prostate. A lot of trans guys are bi, and they can use a dildo, a vibrator, or a strap-on to f*** a partner. They’ll often refer to that toy as their c**k. Most trans guys I know refer to their “cl*t” too as their d**k. So when I say “penis”, “d**k”, or“c**k”, I’m including trans guys’ favourite playthings in this as well.

If you or your partner is trans, you can also enjoy butt sex together. When it’s a trans guy taking a c**k that way, he can get a lot of physical pleasure. The butthole itself is very sensitive: it has as many pleasure nerve endings as the d**khead. Also, I once heard a trans sex educator explain that for a trans guy on a testosterone hormone treatment, the inner part of the “clitoris” develops in a way that could increase the pleasure of anal sex.

Tops and bottoms

In bi and gay slang, the “top” is the person sticking their fingers, penis, or a toy inside their partner; the person taking in the fingers, penis or toy is the “bottom.” Someone who likes doing both is said to be “versatile.”

Beware of poisonous, heteronormative ideas. It’s not because you’re smaller, lankier, smooth-skinned, more fem, or have a smaller penis that you have to be the bottom. Likewise, it’s not because you’re butch, tall, muscular, hairy, or big-d**ked that you have to be the top. The tough quarterback can dream of having his prostate thoroughly f***ed by his buddy (buddies?). The petite femboy can long to plunge his d**k in his friend’s tight a**. In bed, nothing stops you from fulfilling those fantasies, no matter your body type, no matter your everyday life personality, as long as all partners consent.

It can be embarrassing to express your desires, especially when you feel like you have an image of some kind to protect, but learn to do it – you’ll be glad in the end. The same goes if you or your partner is trans: you can be top, bottom, or versatile as well when you’re trans. It says nothing about your masculinity – it’s just a matter of what feels good for you and what fulfills your fantasies.

Likewise, being the bottom does not make you inherently submissive, nor being the top makes you inherently dominant. You can play at being a bossy bottom who orders his top around and who uses him as his sex toy. Just like you can play at being a meek top who wants nothing more than to provide pleasure to his bottom, and to indulge his demands. Or you can have sex with egalitarian roles, with no domination or submission dynamic whatsoever to your fantasies. What you want sex to be like, and what kind of roles and fantasies you want to fulfill, is something you and your partner should discuss and agree on.

Finally, a lot of bi men take on a different role when they have sex with another man than they do when they have sex with a woman. Sexual preferences can be different with men than with women. A guy who sees himself as more toppy and dominant with his female partners can prefer being the bottom, submissive or both with another guy. Or you could have a man who loves to top other guys, but who has little interest in anal sex with women, because he has the opportunity to do something different.

For some people though, their sexual interests remain the same across the board. Some people like anal sex no matter the gender of their partner—no matter the role they end up taking—just like some people have no interest in involving buttholes with their sexual play at all.

A toy chest with plushies. Captions read, "This should be a cute art of a boy choosing what toy his girlfriend will use on hom. You get a very SFW toy boy instead."

Preparing for anal sex

In terms of hygiene, make sure you don’t need to poop before you get penetrated. Some people do an anal douche or an enema beforehand to be cleaner, but many don’t. Things can get a little bit messy with anal sex, so have some tissue on hand and access to a shower.

You will need lubricant (lube for short); when you have butt sex, lube is your best friend. Unlike vaginas, buttholes don’t make their own natural lubrication when you’re aroused; this is going to be a big difference from penis-in-vagina action if you’ve had some experience with that.

Most drugstores sell decent lube now, but you’ll find the best lubes in sex shops or online. Never use oil-based lubes like oils, hand lotion, soap or Vaseline with latex condoms – these will ruin the latex the condom is made from. Stick to water-based or silicone-based lubes with these.

Using sex toys and butt plugs of various sizes is a great way you can get used to bottoming. You can try these on your own, or with a partner whose d**k you want to get used to taking (even when it’s not that big). Whatever object you choose, make sure it has a wide base to keep it from going in too far, and that it’s sturdy enough to not break inside your body. Losing a toy in your rectum will guarantee an ER visit.

HIV, AIDS and anal sex

Of all sex acts, unprotected penis-in-anus sex has the highest risk of transmitting HIV. HIV is the virus that can cause AIDS when you’re infected with it, if you’re not taking the right meds regularly. The rectum’s lining absorbs stuff easily, and anal sex often causes microscopic tears in it. These are two ways the virus can enter the body when semen or blood infected with it gets in the rectum. So with anal sex, you need to think about how you’re going to protect your health and your partner’s.

Bi+ guys are one of the groups of people who are at the highest risk of HIV infecting them at some point (five times higher than for straight men). This isn’t because bisexuality or sex with other guys is inherently harmful (except for the biological risk with anal sex; still, lots of heterosexual people do it and aren’t more likely to get HIV).

Sexual behaviour can play less of a role in your risk of HIV infection than people think. For example, in the U.S., Black and Latino guys who have sex with other guys use condoms more consistently [behind an academic paywall] than white men. Yet their risk of getting HIV is much higher than it is for white guys. It’s our position in society that determines our risk of contact to the virus.

Also, the tighter a social network is, the more opportunity there is for HIV to spread because there are fewer degrees of separation between people. This is true both for men who have sex with men and for racialized communities, among others. Racialized communities of guys who have sex with guys have this effect multiplied.

Because society marginalizes bisexuality (especially among men), this limits our access to information on protecting our sexual health. Homophobia can be a barrier too in health services, and biphobia even more so. Fewer bi guys tell their doctor about their sexual orientation than gay guys, and we use HIV prevention services less. These are just some of the factors why our social position makes us vulnerable to HIV: it’s a complex topic I can’t cover in full here.

Many of these factors are outside your control, as they are outside mine. There are some very effective tools though to protect us from the virus. The external condom (the one that goes on the penis or on a toy) is the one everyone hears about; it also protects you against other STIs besides HIV.

When you think of using a condom, make sure you understand how to do it properly. Choose one that fits you well and that you’re comfortable with—every brand is different, and it’s not true that it’s one size fits all. The main factors that make condoms less effective are using it incorrectly, or using a condom that’s too big or too tight for your penis.

If you use a toy for penetration that more than one person will put inside their body (for example, your partner first and then you), you can spread HIV and other STIs this way; still, the risk is lower than for penetration with a flesh-and-blood dick. Covering the toy with a condom and changing the condom between each partner protects everyone.

Always keep them with you if using them matters to you, even when you don’t expect to get laid. Carry them in a container in which they won’t get crushed or damaged; don’t use your pockets or wallet to carry condoms around when you have nothing to protect them. You can buy condoms at a drugstore or sex shop, but many community organizations and health services hand them out for free, as do health services in many schools; you won’t get to choose the brand though. Many bars and saunas where men who have sex with men go have condoms too.

There’s also what’s called the internal condom. You use it differently by putting it inside the rectum (or vagina), with its opening sticking out of the orifice. There are advantages to the internal condom, but it can be harder to find than the external condom.

Another way to protect yourself from HIV is called PrEP—short for pre-exposure prophylaxis. It’s HIV meds you can take every day—if you fuck a lot—or on occasion. In the latter case, you take PrEP a few hours before you get in bed with someone, and on the two days that follow. Universal healthcare coverage in many countries pays for PrEP for men who have sex with men, and many private insurers cover it too.

Like any kind of meds, PreP can have side effects. It won’t protect you against other STIs either, but it’s an effective way to prevent HIV infection if condoms aren’t for you, or if you want extra protection besides condoms.

When you or the person you have sex with is HIV-positive, treatment reduces the risk of transmission. There’s no documented case of the virus being transmitted through a person with an undetectable viral load. This is when blood tests can no longer detect the virus because treatment is effective.

If you choose to not use condoms or PreP, I would still encourage you to talk with your partner about your health—though you need to be ready to not judge them or become upset about what they tell you, and to reassure them that you won’t—and to get tested before you have sex. You should agree too on whether the top will ejaculate inside the bottom, as this increases the risk of transmitting the virus.

The golden rule of sex

Communicate, communicate, and communicate. Tell each other what things feel like—when they feel good, when they hurt, or when they’re just a tad uncomfortable. Guide each other. When you have the opportunity to talk ahead of time about the sex you’re thinking of having, figure out what you’d like to try, what is off the table, and what are big turn-ons for anyone involved.

Before, during and after sex, check in with your partner. Pay attention to their body language. Make it clear to each other it’s okay to slow down, or to change your mind and stop having sex altogether when things don’t feel good or get weird. No one can read minds, and clear communication ensures everyone involved has as good of a time as possible, and feels respected and safe too.

How to do the actual deed

Humourous sex position chart for two men [NSFW for drawn naked men having sex; we see no genitals]

A good position to start involves the bottom lying down flat on their stomach and the person topping getting on top of them—”Dad & Dad” in the pic above; these names are humourous, and most people don’t use these for these positions. Another good option is to have the person topping lie on their back, and the bottom sit on top to ride their dick, one person facing the other—think “cowgirl” in straight sex, or “The Swing” in the pic above. This gives the bottom a chance to control penetration, but be careful not to bend the top’s d**k the wrong way, as getting it in can be a bit of a struggle.

If you’ve had vaginal sex before, you’ll discover quickly that angles work differently with anal sex. If this is your first experience with any kind of penetration, expect some awkwardness – positioning can get clumsy even with a lot of experience.

The person bottoming will have an easier time when they feel relaxed, comfortable and trusting towards their partner. Deep, regular breaths help. So does reassuring each other that you’ll stop if anything hurts, or if you don’t want to do this anymore no matter the reason.

Start penetration with one finger. Use a lot of lube. Go in very slowly. There’s one ring of muscles (sphincter) on the outside, and one on the inside, so don’t think you’re in completely the moment you’ve passed the first “barrier” – you’re not. These sphincters will get used to something entering them, and they should relax eventually. This will make it easier to penetrate with something bigger.

Once things feel easier and the person bottoming feels ready for it, add a second lubed up finger. Some people don’t like being fingered and would rather do this step quickly. Some others love it, and you can do this as long as it’s enjoyable. A small buttplug or toy an option too at this point.

A sparkly transgender pride flag. Captions read, "This should be a trans guy topping a cis guy. You get a trans pride flag with pretty stars instead."

When you’re ready to penetrate with a penis—whether it’s flesh-and-blood, a toy, or a prosthetic—put on a condom when you use one. Lube up the penis and the butthole; too much lube is better than not enough. Penetrate very, very slowly: whatever you think is slow enough is too fast. Once again, communicate with each other.

Butt sex isn’t supposed to hurt when you do it right; when there’s pain, it means something is wrong, and you should stop. Feeling weird or uncomfortable at first for the bottom is not unusual. Just pause, keep things where they are, and wait a minute (remember, deep breaths); the butthole will relax and figure out that something different than pooping is going on. When things get comfortable again, resume slowly. When things feel sore for the person bottoming, add some lube.

Keep communicating with each other to see how you’re doing. As the person who bottoms gets warmed up, sex should get easier. Odds are you’ll be able to f*** each other’s brains out at some point. Still, be mindful of what the bottom’s body can take, especially if the person topping has a bigger than average penis, or uses a larger prosthetic d**k or toy.

Once the person bottoming is warmed up, it’s easier to try out trickier positions. Sometimes you need to change the condom when things get a bit messy (so have spares), and pillows can help with some positions.

When it’s penis-in-vagina sex you’re used to, be warned: butt sex is trickier, and it’s easier to hurt a partner if you stick something into their butthole too fast. It can be more difficult too for a bum to accommodate a larger-than-average d**k—for the record, the average penis size for an adult is 13 cm in length by 13 cm in girth, in erection.

Each person’s body is different when it comes to how big of a thing they can take, and experience in taking a dick often not the factor. Sometimes your butt or their butt is just too tight for that thick 18-centimeter long d**k, and you can’t help it. Even when you or your partner has a small to average-sized penis, jamming it in without careful preparation is a terrible idea. Eleven centimeters worth of c**k feels a lot bigger when you have to take it up your a**.

Expectations, and the aftermath of anal sex

An exploding geyser. Captions read, "100 sex facts. Number 37: Ejaculation occurs within 5.4 minutes of penetration for 50% of men."

Penetration can be over quickly, or it can last a long time. Some tops cum in moments, some others won’t be able to cum from f***ing alone. Sometimes a top loses his erection, and you have to stop penetration. Have sex often enough and that’ll happen to you at least once in a while – boners are fickle things. Likewise, some bottoms can take a pounding for a long time, some others will feel like “they’re done” after a few minutes.

Most people who bottom won’t cum just from being f***ed; they will need to stimulate their d**k too. A lot of people enjoy getting fucked best while they jerk off. Also, some bottoms go soft while they’re taking a c**k even when things feel amazing; it’s how their wiring works.

Each person’s body is different. Do what works, and focus on what feels great. Stop when someone’s not enjoying things anymore. Love and respect the unique way your partner’s body and your own react, and work with it.

When you’ve been bottoming, you can end up with a sudden urge to go to the bathroom after you’re done. Also, your butthole will feel looser, but this won’t be permanent. Whatever you’ve heard about “anal leakage” is a sex-negative myth.

A little bit of bleeding can happen on occasion, and it usually stops quickly. If bleeding doesn’t stop or there’s persistent pain though, go see a doctor – it’s a sign of a potential anal fissure, and you might need treatment. Anal fissures are rare, however, even when you have rough sex on a regular basis; the vast majority of people who bottom will never end up with one.

Butt sex can go wrong when people don’t know what they’re doing. It’s possible you won’t find your first experience pleasant. Still, you may want to try again at some point. It’d be a shame to miss out on all the pleasure anal sex can provide because of one lousy experience. Not everyone enjoys butt sex though, and it’s okay if it’s not your thing; there are plenty of other sex things you can do with guys.

There’s another side to that coin. There are guys who are into butt sex with other guys, but who don’t feel attracted to men, and don’t like doing other sex things with them. They may or may not identify as bi, even if they shag men once in a while. Sex is complicated, but when you accept your sexuality the way it is with all its quirks, you can have a great time!

Finally, like all sex acts (and perhaps more with this one than others), pleasure isn’t automatic. Sticking the magical penis into the wondrous butthole won’t in itself result in screams of ecstasy from both parties. So talk with each other. Try things. Tell each other what feels good, what doesn’t, what is a bit boring, or what makes your brain melt into sex goo. Pay attention to nuances and subtleties.

Sex isn’t arcane sorcery, but you have to learn how to make each other feel amazing, and each partner enjoys different things. Keep this in mind, and you’ll have a better time than most in bed.

Two shirtless, tattooed men lying in bed, hugging each other tenderly.