Our product picks are editor-tested, expert-approved. We may earn a commission through links on our site. Why Trust Us?

My first time bottoming was a nightmare come to life. I was in pain the entire time, not to mention super self-conscious about my partner being all up in my rear end.

If you're not familiar with the term, "bottoming" refers to being on the receiving end of anal sex, meaning the "bottom" is the partner putting the penis (or dildo) inside of them. (The person sticking said penis or dildo inside the bottom is referred to as the "top.")

After my negative sexual experience, I couldn’t for the life of me understand what was pleasurable about bottoming. How do so many men—gay, bi, and straight—derive pleasure from having a penis (or dildo) inside of them? After my first unpleasant experience, I didn’t bottom for quite some time. Eventually, I had a girlfriend who got me into it. She really wanted to peg me, so I told her I’d give bottoming another try. She loved anal (on herself, too) and taught me what I had been doing wrong. After a few experimental sessions, I finally got what bottoming was all about. It felt heavenly. My orgasms were so much stronger with something in my butt than without.

I had no idea how to bottom, which makes sense. Bottoming isn't an innate skill; it’s something you learn. Alas, there are not that many resources for men who want to learn how to bottom, but have no idea where to begin. That’s why we spoke to Dr. Evan Goldstein, founder and CEO of Bespoke Surgical, an anal surgery practice, for medical information and advice. We also spoke to legendary gay porn stars Boomer Banks and Ty Mitchell for tips on how to bottom.

Why do men bottom?

Well, for one, cisgender gay men don’t have vulvas, so if they want to have penetrative sex, it’s really their only option. Two, it feels really good for the bottom. Roughly 2-3 inches inside the anus resides the prostate, a walnut-sized gland that’s a beacon of pleasure. “Once you tap into its benefits with appropriate stimulation, your orgasms will never be the same again,” says Goldstein.

Relaxation is key to enjoying the bottoming experience.

To have a pleasurable (and safe) time bottoming, you need to relax the voluntary muscles in your butt in order to accept whatever you’re inserting into it, explains Goldstein. You also want to start by inserting smaller things—like fingers or small butt plugs—before taking a full-on penis or dildo. (Note: Any toy that goes up your butt needs to have a flared base—you don't want it getting stuck up there!) If you stretch beyond your capacity, you can cause damage to the region—most commonly in the form of anal fissures or hemorrhoids.

Using yoga-style meditative breathing can assist in pelvic floor relaxation, explains Goldstein. Use big, deep, full-bellied breaths. He also suggests “pushing out the pelvic floor during the initial insertion.” Whatever you do, do not clench. For some, it’s a natural response to having something inside if you, but you need to fight the urge.

How to practice bottoming by yourself:

You can start by inserting a lubed-up finger, but make sure to cut your nails extremely short and file them down. As someone who's had his anus fingered by women and men with long nails, I can tell you it’s very unpleasant when they accidentally scratch your insides.

Goldstein recommends using anal dilating kits. Dilating kits, in essence, are a few dildos that range in size. You start with the smallest toy, lather it up with as much water-based lube as you possibly can, and then put it inside of you. You breathe with it inside of you, and get used to the sensation. You can also “play with it,” moving it in and out of you with your hand. Goldstein recommends leaving it inside of you for 3-5 seconds before removing it. Then reapply lube (if necessary) and do it again. He suggests doing 10 reps per set and 2-3 sets per session. Only after inserting a dilation toy with ease, can you move onto the next size. Generally, it takes about two weeks to transition to the next toy, assuming you’re doing these exercises 2-3 times a week, Goldstein says.

Size Matters Magnum Ease-In Anal Dilator Kit

Size Matters Magnum Ease-In Anal Dilator Kit

Dilation kits are absolutely great, but they're also not necessary for every person who wants to bottom. Personally, I’d recommend buying a small prostate massager, and getting used to that. (It should also feel really good!) Just make sure to go slow, use a lot of lube, and breathe through any discomfort. Mild discomfort you can breathe through. Pain, you should not. That's a hard stop.

Writer and porn star Ty Mitchell, better known by his social media handles, Probottom, recommends “being really intentional and thoughtful” while practicing on yourself. You need to identify which things help you relax, which movements make you clench, and how to breathe, he says. “This practice of embodiment and thoughtfulness helps you get in touch with your body, which is necessary to use your asshole sexually.”

When practicing by yourself, make sure you’re aroused too! Watch some porn that really turns you on. If you’re sticking something up your butt without being aroused it can be an uncomfortable experience. It feels medical (and not pleasurable), which can make it difficult to relax.

How do you go about bottoming with a partner?

Bottom with someone you can really communicate with. "It's about reaching a level of comfortability for you," says Boomer Banks, the renowned gay porn star. “Really try to connect with them beforehand.” Talk to your partner about their dos and don'ts, and share your own.This is even more important if you're new to bottoming.

With your partner, start slowly with fingers or a small toy, and use a lot of lube. Silicone-based lube can help with anal sex because it’s thicker. It's safe to use with condoms along with water-based lubes. Oil-based lubes, on the other hand, can erode latex.

Lovehoney Water-Based Lubricant 8.5 fl oz

Lovehoney Water-Based Lubricant 8.5 fl oz

When you start to have penetrative sex, do it from a position where you control the thrusting. I often start in the cowgirl position, and tell them to not move. That way you control how far the penis or dildo goes inside of you. If you start in doggy style, your partner controls the thrusting, and they may accidentally go too quickly before you’re relaxed and ready.

What are the proper ways to clean yourself out before sex?

One of the biggest fears of bottoming is accidental poop. “What if I poop on his penis?” is a question nearly every bottom has asked himself at some point in his life.

“It's a natural side effect," says Mitchell. “It still happens to me, someone who’s bottoming all the time,” he says. And if your partner is rude or judgmental to you about it, then know that they’re the asshole, not you.

While pooping during anal sex is by no means the end of the world, there are still ways to minimize risk. The most common way is to clean your anus using a douche. “The goal of douching is twofold: cleanse the anal canal and rectum with as little trauma as possible to the region,” says Goldstein.

The two main ways you can clean your asshole is to douche using a little bulb, where you squeeze clean water into your ass, or using a hose that you can connect to your shower head, and insert that into your behind (often referred to as a shower enema). With either device, you lightly pump the water into your asshole and squeeze it up inside of you. (Note: Please just use clean water. Don't add any oils or scents!) You let it sit inside of you for a few seconds. Mitchell says he counts to 10. Then you expel the water from you. You keep on doing this until you can expel completely (or at least relatively) clean water. You also don't need to squirt that much water into your behind. You're not trying to completely fill it up. You're just rinsing it out.

A note about using a shower hose. It can be difficult to control the pressure of the shower water, and you don’t want to accidentally burn your insides by using water that’s too hot. (I've done that and have never screamed louder in my entire life.) So before inserting the hose inside of you, make sure it’s the right temperature (a little colder than lukewarm) with a gentle pressure. Don’t stick in the hose and then turn on the water.

OTBBA Anal Silicone Douche Bulb

OTBBA Anal Silicone Douche Bulb

One of the very annoying things about douching and enemas is that it can cause damage to the the anal region if you douche too much. “It can disrupt the microbiome in your butt, which affects the normal balance of the good and bad bacteria that resides there,” says Goldstein. “As a result, there’s a chance that micro-cuts and tears can happen, and with the washing away or the absence of the protective layer, it can lead to a higher chance of contracting HIV and other STIs.”

Unfortunately, there’s no consensus on what constitutes as douching "too much." This is likely because it depends on how much water you use each time, what pressure you use, etc. Nevertheless, Goldstein says, “Less is always more and if someone is following an appropriate protocol, then 2-3 times a week seems fine.”

Some studies have shown that a pH-balanced isotonic solution, as opposed to regular water, can potentially help clean anal tissue without damaging the cells as much. So if you find yourself douching frequently, it might be worth it to invest in an isotonic solution, like Future Method.

How does diet come into play?

“What most people don’t realize is that being ready to bottom actually starts with your diet,” says Goldstein. In fact, if you maintain a diet that’s full of fiber (either through food or supplements), anal douching every time before sex may not be necessary. Fiber keeps your bowel system regular and moving, which is what you want.

Metamucil Fiber Supplement

Metamucil Fiber Supplement

Greasy, fried, fatty, creamy, heavy, or spicy foods that upset your stomach aren’t ideal if you’re trying to maintain a healthy bowel system. Fruits are good! Mitchell makes clear that for him, it’s less about what he eats as opposed to his dietary consistency. He has a relatively light and healthy diet that's high in fiber, but will also drink a cup of coffee before heading to set, which in general, wouldn’t be recommended since coffee has caffeine which can cause you to poop. At the end of the day, you need to learn for yourself which foods work best for you.

What are some of the health/safety risks of bottoming?

There’s a risk of HIV and STI transmission, as there is with any sexual act. “Additionally, the external skin, rim, and walls of the anal canal are quite thin and are more prone to several types of injuries, such as tears, hemorrhoids, skin tags, and abscesses,” says Goldstein.

Condoms, of course, are the best way to help protect against STIs and HIV. You can also take one of two FDA-approved antiretroviral medications, either Truvada or Descvoy, for PrEP (Pre-Exposure Prophylaxis). These daily medications decreases the likelihood of acquiring HIV through sex by about 99%, the Centers for Disease Control and Prevention report. If you find yourself bottoming with a lot with different partners, PrEP is something you should consider taking. Ask your doctor.

As for the damage done to your anal region? That’s why we recommended practicing by yourself first, breathing deeply to relax, using lots of lube, and bottoming from the top position, so you’re in control. All of these tips aren’t just to help you enjoy your bottoming experience, they also help prevent any injuries.