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Published on September 11th, 2015 | by Healthy Gay Lifestyles


Does Bottoming Have To Hurt?

by Joe Kort, Ph.D

I am a gay 21-year-old male, and I often have casual sex; most of the time it’s just oral and not anything more. However, I know that I am versatile, but I have only topped before. I tried to bottom a couple of times, but I couldn’t go through with it.
My question is, simply, how can I make bottoming hurt less? I really wanna do it, but it just hurts too much. How can I change that?
Thank you very much,
First, make sure that you genuinely want to do this, and you don’t just feel pressure to do so.
There can be a lot of sexual pressure to be a top, a bottom, or versatile, says Kort. In fact, the pressure to be willing to take turns is something that seems to be even more prevalent in younger guys, he says. But it’s important to remember that you don’t need to fit into any of these distinct categories, and you don’t need to be willing to change your sexual preferences for any partner. Some gay men don’t engage in any kind of anal penetration at all, and that’s perfectly normal, too.
That said, a little sexual experimentation is healthy, so if you’re genuinely curious and excited about bottoming, there are definitely ways to do so in a safe and satisfying way.

Start by doing some prep work when you’re alone and relaxed.
Getting comfortable with anal penetration solo can make the experience a lot more pleasurable when you eventually do it with a partner. When you’re in the shower or in bed, insert your fingers slowly to see what feels good, says Kort. Start with one finger, then work your way up to two or three. And definitely use lube to make things smoother and more comfortable. You might want to try self penetrating with a dildo, vibrator, or butt plug, too. You can even use a vaginal dilator in your anus to become comfortable with bigger widths. Just remember to pay attention to your own pain threshold, and if it really hurts or you start to bleed, stop.
Make sure you’re really relaxed, breathing deeply, and in a situation where you won’t be disturbed. If you get too overwhelmed, take a break and take some deep breaths until you’re ready to try again. There are also some books that can really help you understand and enjoy anal play. Kort suggests The Ultimate Guide to Prostate Pleasure: Erotic Exploration for Men and Their Partners by Charlie Glickman, Ph.D, and Anal Pleasure and Health: A Guide for Men, Women and Couples by Jack Morin, Ph.D.

When you’re ready to try it with a partner, keep these things in mind:

Make sure you really trust your partner.
Whether this is a new hookup or someone you’re in a relationship with, you need to feel safe with this person, says Kerner. You want to be comfortable communicating with them and trusting them to help you have an enjoyable first experience. It can also help to tell them it’s your first time, that you’re nervous, and that you want to go very slow.

Do whatever prep work will make you feel more confident and comfortable.
Maybe that’s a glass of wine, a little weed (if it’s legal where you live), an enema, or some combination of the above. If cleaning yourself out will make you feel a little more secure, Kerner suggests getting a small standard enema bottle at the drugstore and filling it with warm water. This will make you want to go to the bathroom (a lot), so be prepared.

Ease into it with other anal play first.
Kerner suggests starting with some rimming, fingering, and foreplay to help you get relaxed and aroused.

Always use a condom and a lot of lube.
A silicone-based lube might work best, since it keeps you lubricated longer than a water-based lube, says Kerner. Just stay away from oil-based lube and products, which can break down latex condoms and make them less effective.

Make sure you’re the one in control.
Since this is your first time and you’re concerned about pain, you should really be the one controlling the depth and thrusts. The best way to do this is usually to have your partner on his knees, holding his erect penis, and you on all fours in front of him, suggests Kerner. “You back up into the erection, you control the thrusting, and you control the movement,” he says. “Take it slow. You don’t have to take in all of his penis the first time.” He also suggests bearing down a little, which can help open you up and make things less painful. Focusing on your breathing can also help ease the pain. As you exhale and your body relaxes, you may be able to take more of him in.

IMPORTANT: Trust your own pain threshold, and stop if it really hurts.
This is why you want to be the one controlling the speed and depth of penetration. If something really hurts, stop. It’s normal for there to be some pain, pressure, and even bleeding the first time around, but trust your gut and stop if it’s too uncomfortable, says Kort.

Remember: It’s completely OK if this ends up not being your thing.
Kerner has heard this same nervousness from men who are young, old, inexperienced, or very skilled. “Know that you’re not alone, and there’s nothing wrong with feeling anxious,” he says. And the more you do it, the more comfortable it will become, says Kort. That said, if you realize that bottoming just isn’t a satisfying or enjoyable experience for you, that’s perfectly fine too. You should never feel pressured to go along with any sexual act that you’re not comfortable with. So go slow, experiment safely, and figure out what feels good for you.

Joe Kort, PhD., LMSW is a psychotherapist, board-certified clinical sexologist, certified sexual addiction therapist, and certified lmago relationship therapist, practising for over 25 years. He is the author of, 10 Smart Things Gay Men Can Do to Improve Their Lives, 10 Smart Things Gay Men Can Do to Find Real Love, and Gay-Affirmative Therapy for the Straight Clinician.

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