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Sex & Dating

Be Better to That Booty

Be Better to That Booty

Shame-free tips on increasing your sexual health and pleasure.

While this is advice for those who identify as “bottoms,” anyone who has anal sex should have an understanding of the process involved in successful bottoming. It will help you be a better “top” and positively affect your sexual experiences.

The act of bottoming is a true art, and whether it’s your first attempt or you’ve been experimenting with it for quite some time, analyzing your readiness and the proper techniques not only allows you to reach heightened sexual pleasure, but also enables safe and enduring practices.

If you’ve never tried bottoming, but you’re curious, you shouldn’t just dive in without preparation. Successful and pleasurable bottoming takes time and practice, through dilation exercises, training of your self-awareness, and control of the pelvic floor.

The good news? Bottoming shouldn’t hurt. Of course, it may be uncomfortable at first and you might initially question how there could ever be pleasure in it—something that happens with vaginal sex the first time as well.It takes practice, patience, and following a few simple guidelines to enhance this sexual practice. I often tell patients that great bottoms have been doing it for quite some time, with many first experiencing it in their youth. Unfortunately, no one showed us the right way to bottom in our high school sex ed classes. Still, it’s never too late to learn so you can enjoy new and positive sexual experiences.

Here’s my 101 guide to bottoming:


Get yourself an anal trainer kit, and start training for dilation two to three times a week (for as little as five minutes each time). Use a water-based lubricant and start with the smallest plug. Insert just to the point of pressure. Hold it there for a few seconds, then try to engage the muscles. Allow yourself to relax before removing the plug, then re-lubricate and re-insert to the point of pressure. Repeating this process will prove successful over time, so don’t get discouraged if the first time you only get a small portion of the tip in. Repeat the process three to five times. The key is to remember there are three sets of muscles that need to relax for a successful entry. Think of it as a tunnel, and the entire tunnel needs to be a well-lubed cylinder. We don’t advise inserting the entire length of the plug and leaving it in on the first try, because removal may be difficult, which could cause tearing. If after four to five sessions you can insert that size without any issues, you’re ready to graduate to the next size. Don’t forget to enjoy it. If you become stimulated during the process, go for it! Not only is it a pleasurable side effect to your dilation training, but you can start to channel your orgasm anally and begin to gain control over time.


When you’ve successfully mastered a medium size plug, you’re ready to graduate to the real thing. Congratulations! It’s always best to start off with you in total control and a partner you trust to be patient in letting you decide the level you’re comfortable with. Some people use dilators first, either with or without a sexual partner, to “warm up” and remind themselves of the practiced techniques. Once the engines have been started, the bottom needs to sit on the tip of the penis, allowing control of entry. Use plenty of lubricant and remember the different sets of muscles that need to be released to allow access. Start off using the same technique of inserting until you feel pressure, hold it there, pull out, re-lubricate, and repeat. The three to five-time rule applies here as well. Being on top of the penis really allows for you to determine your level of comfort. If pain occurs, you can stop, call it a day, and try again another time. It’s not worth causing pain or a potential injury.


Once you have fully received the penis, the last hurdle is to add new positions into the mix, like doggy-style. Now, be sure to take this easy to begin with—it’s an intense position and tops can get a little eager. Make sure you have mastered receiving to minimize any injury and maximize pleasure. Start with you receiving on top and gaining control of your muscles before moving around to new positons.


Proper techniques are obviously a must, but even brand-new cars can break down. The most common issue related to anal sex trauma are tears, also known as anal fissures. If this happens, take a break but don’t get discouraged. Most anal fissures will heal themselves with proper care, but fissures that become chronic will require surgical intervention. If an injury happens, it’s best to analyze why it did so you can plan to avoid reoccurrence in the future.


Small, petite frames and pelvises just may not be able to accept those of the more well-endowed variety. Be realistic with your goals, and realize that you may need to work up to this over several months.


The key to continued ease of bottoming is to be consistent in using the above dilation methods, even throughout sexual dry spells. We all have them so don’t fret, but just remember if you don’t use it, you lose it. Keep at it so the next experience is a pleasurable one.


The process to becoming a pro at bottoming can be daunting, but it is totally achievable if you follow the above process. If all else fails, see a specialist in gay sexual health and wellness, who can provide both medical—such as personalized dilation and Botox—and surgical options (including anal restoration) to help improve results and assist in relaxation of the muscles.


Dr. Evan Goldstein, founder of Bespoke Surgical (with offices in New York and Beverly Hills), has extensive experience educating gay and bi men on health care issues, including: anatomical and mental sexual dysfunction; different same-sex relationship types and their evolving dynamics; HPV prevention, management, and treatment; anal Pap smears and cancer prevention; sexual education (i.e., proper techniques to minimize injury and enhance overall sexual experience); and how medical advances have revolutionized the way that gay men have sex.

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