How To Be Better at Bottoming

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The last post was dedicated to becoming better at topping, you can read it here just in case you missed it. But with that out of the way, sex still remains a two way street, so here’s part two on to become better at bottoming.

Have you ever looked at gay porn and thought, “How can they make bottoming look so easy?” A hung top sticks it in like a glute inject and the bottom doesn’t even flinch. Bottoming isn’t just about the physical sensation of being penetrated, it’s the emotional high of accepting someone else’s presence in your body. It’s the psychological thrill of being momentarily “owned,” of submitting yourself to the strength of another man.

This is the single biggest emotional stumbling block gay men have about bottoming—being labeled less than a man. For many of us, bottoming isn’t an opportunity to enjoy a pleasurable sexual experience but an act that threatens our sense of masculinity and the respect that goes with it. Many gay men believe that if they bottom they will become “a bottom.” They fear that bottoming will create a new unwanted identity for them. It just may be that you haven’t been able to bottom (or been able to enjoy it) because you have so many emotional issues around the act. If you can get away from the falsehood of bottoming as an identity and see it for what it is—an erotic activity—the more relaxed and receptive you will be.

We label men “tops” or “bottoms” in part because we’re living out antiquity’s fear of the feminine. In heterosexual thinking, the penetrator (man) is more valuable than the penetrated (women). We’ve adapted that consciousness in our own community, where the penetrator (top) is more valuable than the penetrated (bottom). Clearly, labels like “top” and “bottom” can be useful shorthand for sexual likes and dislikes. But instead of stating what we prefer— “I like to bottom”— we turned that preference into an identity —“I’m a bottom.”

Masculinity isn’t about what you put into your body.
It’s about what you put out in the world.

“Anticipatory pain” is a psychological term for the expectation of pain. It speaks to the emotional and physical consequences of this expectation. This expectation of pain contributes greatly to your inability to relax. With the right conditioning your anal muscles can relax enough to easily accommodate a penis without any pain. The two words you’ve probably heard from partners who tried to top you.. “Relax! Relax!”

Deep, slow breathing operates on a feedback loop: Relaxation causes deep, slow breaths which causes more relaxation which causes more deep, slow breaths. You can get muscles to relax more by first increasing the tension. When you release the tension there’s a more dramatic experience of relaxation.

Getting clean

Improve your diet, specifically incorporate more fiber and drink enough water. By “bulking up” waste matter and shaping it for easier transit, fiber ensures that feces leave the rectum and anal canal virtually intact. Examples of soluble fiber include bananas, apples, brown rice and white beans.

Enemas are harmful. Pushing water or a mixture of water and chemicals up your bum creates a powerful peristalsis (accompanied by bloating and cramping) that “evacuates” everything in your lower intestinal tract. Douching could have some serious negative effects as well. Firstly, frequent douching (even if it’s just plain water) may compromise the natural protective fluids and lining in your anus. An intact mucus layer protects your rectal tissues from abrasions, tears or cuts that could endanger your health. Here is the best way to get clean – using an ear syringe.

Ear syringes hold about one ounce of water—enough to get the job done but far too little to remove rectal mucus or cause peristalsis and its consequent “douche dependency.” Here’s how to use it:

1. Fill the ear syringe with warm water.
2. Apply lubrication to the tip (always use a soft-tipped syringe).
3. Insert into your anus gently.
4. Squirt gently.
5. Retain for a moment. Release.
6. Repeat until clean

Getting Into It

After you or your partner has safely put on a latex condom, the best position for first timers is squatting over your partner which straightens out the S curve better than any single position. Squatting loosens the puborectal sling, allowing the rectum to straighten out so that it comes close to being vertical. With entry in other positions, you—not your partner—must guide your partner’s penis in so that it slides along the rectal wall rather than poke at it. Only you intuitively know what path the penis should take. All things being even the best angle of entry is about 15 degrees away from your navel. Remember to use lots of lube, way more than you probably are using now, add lube every five minutes or so to your partner’s penis as well as your anus. Try having your partner use a circular rather than a thrusting motion. Some guys initially don’t like the straight in-and-out business (it can happen if you partner’s penis is unusually stiff, straight or longer than average).

Experiment with different positions. If missionary isn’t working, try resting one leg over his shoulder and the other one on the bed. Or try laying on your side, facing away from your partner as if you were spooning. Because it’s a common sleeping position, it helps the body relax faster and deeper. Don’t be afraid to try things that seem a little odd. If it feels good it’s because your S curve straightened out and your partner’s penis stimulates the prostate in a more effective way.

Stop when it feels uncomfortable or if you need a break. This is your maiden flight. Do not push yourself, pace yourself.

Final tips

  • Don’t worry if you lose your erection or only get a partial one. While it may be a reflection of your emotional discomfort, it’s just as often the case that your erotic attention shifted away from your
    penis to your anus.
  • Try to avoid doggie style at first. This position allows the maximum insertion of the penis into the rectum, which may be uncomfortable the first few times you bottom.
  • ALWAYS be safe. Use a latex condom and get tested regularly.

The Attractor

20 thoughts on “How To Be Better at Bottoming

  1. Pingback: How To Be Better at Bottoming | KitoDiaries

  2. Pingback: The Mini Guide to Virgin Sex; and those who have sex with them | The Attractor

  3. Thank you for sharing this article – I am very new at this even though I am in my 30s. It is very accurate on the conversation I had with him over the weekend and we talked about it all at the dinner table. Well this weekend will be the test to this article as I am going to mark my first experience at being a bottom. Again, thank you for sharing.

  4. I read your posts to stay informed for talking with those I counsel. As a hetero female, I can say that being told to relax is not always sufficient. I was so surprised to find vaginal penetration difficult when I started. Even with great willingness and arousal, my body would not cooperate. To those folks who are interested in receiving but having trouble with penetration, please know that practice makes better. Don’t give up and say it is never for you. Having your orgasm first may help the anal sphincter to open more easily. Gradual introduction of dildos during masturbation, when you are completely in charge, helps. Lastly, someone who accepts penetration can in fact the person in charge, as many women will attest. You have what he wants. Know it.

    • A bottom should be getting pleasure from the TOPS penis not his own! There are of course no rule against it. I personally forget i even have a penis while bottoming.

  5. Hats off to you for discussing this! We dont do it enough. But my question: Is it normal if you never get or keep an erection while bottoming? …

  6. Every large mass, from the tallest skyscraper to the Pyramids in Egypt sits on top of a strong bottom foundation. There strength at the bottom, therefore any notion that it denotes weakness is purely a myth. I feel like Superman after bottoming.

    More importantly. It doesn’t matter whether you are pitching or tossing you are still in the game.

    • A-men to that! Just because youre the top doesnt mean youre better. Ive had fem and masc boyfriends that were tops and they never treated me like I was any less important.

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