That brings me to my my first piece of advice for anyone looking to bottom: Do not compare your experience to porn. When my first sex attempts didn’t happen like porn, I assumed I was doing something wrong. Your first experience won’t be like porn. I’ve worked on professional porn sets and can assure you: All the messes, failures, half-starts, and struggles happen in porn, too. In part one of this guide to bottoming, I explored fundamental questions surrounding the act — “Am I a bottom?” — along with how to mentally and emotionally prepare for receptive anal sex. How do I prepare to bottom?
Many people douche before bottoming, meaning they use water to clean the lower part of their rectum — the space in your butt just inside your hole — to flush out any poop before sex. A disposable one purchased at a drugstore or pharmacy will do the trick (don’t forget that many are filled with laxatives, which you must empty and replace with water before using), or a larger squeeze bulb with a plastic or silicone nozzle, purchased from a sex novelty shop or online. You’ll discover what kind of douche you want to use, learn different cleaning methods, or find that you don’t really need (or want) to douche at all.
Many people don’t, and you don’t always need to douche to have an enjoyable experience bottoming. What you eat plays a major role in how “clean” your butt can be. If you eat a high-fiber, veggie-heavy diet and avoid excessive red meat, your poop will be less messy and more “together,” meaning the douching process will be minimal — which is what you want. Some people with careful diets skip the douching process altogether and are naturally “ready to go” (vegetarians and vegans especially). Most people do not consume enough fiber, which is vital to your overall gastrointestinal health (and makes anal sex easier and less messy — double win!). When you’re new to douching, go slow.
Lube up the tip of your enema with a body-safe lubricant (I recommend silicone-based lube), and slowly insert the nozzle into your hole. Gently squeeze the bulb and slowly fill your butt with water. Note: You don’t need to squirt a huge amount of water up there, at least not when you’re a beginner. More advanced forms of sex require more extensive cleaning regimens, which do require more water, but that’s not for beginners. When you’re starting off, there’s no need to empty the bulb. After you do this, your butt might feel strange and “full.” To avoid discomfort, make sure the water is warm — not hot — before you start.
Also, don’t stick the nozzle all the way in — there’s no need to, and you can hurt yourself if you’re not gentle enough. And make sure you try to release all the water into the toilet when you’re done — water left in your butt can cause discomfort later on. Don’t freak out if you can’t get totally clean. Yes, you can get pretty clean, but cleaning out is not a requirement for bottoming. Many people, including some medical professionals, recommend skipping douching in the first place, washing your butt with soap and water, putting a towel down, and simply cleaning up any mess after. Then you’re not clean.
Don’t call yourself — or your sex — a “failure.” You will have many sexual experiences in your life where you'll think you're clean until your body has other plans. Flushing your butt can disrupt and dry out the good bacteria in your colon that you need to process waste, so cleaning for too long isn’t healthy. The only thing you can control is what you eat, and eating a healthy diet that’s high in fiber and low in red meat will make your cleaning process much easier. Does bottoming hurt? Bottoming is rarely a delightful experience in the beginning, because you don’t know what you’re doing.
Because the anal walls have to expand to accommodate a penis, dildo, or other object, and that can be painful — especially when you’re new to the sensation. But don’t worry; once you get better at it, it feels great. No sex is perfect when you’re a beginner. Also, there are ways you can train your butt muscles to relax, stretch, and make the experience easier (see the last question of this guide). Some people recommend taking a deep breath when your sexual partner first enters you. While these classic first-timer techniques to minimize pain have certainly helped many folks relax, they’re not the first ones I recommend.
I’ve trained several first-timers for bottoming (as well as for more extreme forms of anal sex play), and here’s my best suggestion: While your sexual partner gently slides a finger in, take ten deep breaths, breathing in through the nose and out through the mouth. “Squeeze” their finger with your butt, hold the squeeze for a few seconds, and then relax. In your mind, start with the top of your head and slowly relax your muscles, “scanning” down your spine, down your legs, and ending at your hole. Close your eyes and picture your butt, and picture it opening, expanding like a circle. Keep “gripping” and releasing their finger until you’re ready for them to add another finger.
Work up to two fingers, then three, until you feel comfortable gripping them — in control, powerful, flexing your butt muscle. Tell them when you’re ready to try their dick, dildo, or any other sex toy in your arsenal. You’re in control. Breathe deeply and slowly, and guide them into you. How do I protect myself from HIV and other sexually transmitted infections? Micro-tears in the anus happen pretty easily when you have anal sex. The walls of the rectum (the inside of your butt) are delicate. If you’re new to bottoming and haven’t trained your butt to relax, your risk of tearing and pain is higher. More severe ones are called “fissures,” and these you will probably feel.
Fissures usually heal on their own, too, but it’s still a good idea to see a doctor you trust, who knows what kind of sex you’re having. While micro-tears or fissures are rarely very painful, they become open gateways for infection. Unprotected bottoming is a high-risk activity for sexually transmitted infections like HIV, syphilis, gonorrhea, chlamydia, and more. That said, you should talk to your doctor about getting the three-part Gardasil vaccine for HPV, even if you’ve already been sexually active. Even if you’ve already been very sexually active, Gardasil is still recommended to fight future strains of cancer-associated HPV.
Get your body and your butt regularly inspected by a doctor for warts and other signs that you might have an infection. If you’re having sex, you should get a full-range STI test every three months, minimum. Many STIs are asymptomatic, meaning you won’t know you have them, so it’s important that you get tested often, especially if you’re HIV-negative. Improving your sex skills takes time, practice, and — in my opinion — some butt training. Not every bottom trains their butt to prepare for the experience, but I did. Buy a small butt plug (no larger than an inch in diameter), preferably one made of smooth, soft silicone. Concentrate on the feeling of the stretch and slowly — slowly!
If you feel pain, stop, breathe, relax, and continue when you’re ready. Once the plug is all the way in, take a deep breath, adjust to the feeling of it being inside you, and slowly — slowly! Breathe, relax, and repeat. You will probably find — as I did — that after you stop clenching and finally relax your butt, the feeling of your hole opening feels really good. After working with the same small plug for a few weeks (or as long as it takes to feel enjoyable), try a slightly bigger butt plug. If it’s too much, stick with the smaller one until you’re ready. Gradually build size and speed, and above all else, focus on enjoying the feeling.