How To Be Better at Bottoming

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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.

300Ear 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.

39 thoughts on “How To Be Better at Bottoming

  1. Good morning pinky *Plants a wet slimy kiss*

    O’boy you ve been dropping it like its hot (in my snoop dogg voice) all week. Great stuff! The 1st part of the piece had me mentally waving my hand and saying “preach it bae, pureeaach it now”!!!!!

    Goodmorning Y’all

  2. They keep saying the best position for first timers is squatting when all I could think of back then in that position was that I was about to be impaled like dry fish in the market.

    Doggie turned out to be the best.

  3. Lol. Nice points. Tops should be clean too. I don’t like taking extra care bathing and cleaning and washing, and then I go and:

    1. The guy’s boxer looks like something his great-grandfather passed on to him


    2. He smells like old clothes down there. And I happen to like giving (and receiving) blowjobs.

  4. That shit is so true about them super straight dicks, it’s pencil straight and so hard as if there’s a bone in it. I can’t deal with those ooooo however small….they keep poking your rectal wall probably bruising them in d process.

    • Em Nonzy luv welcome again…not a doctor but when you see a dick that’s xxxlarge and YOU are not in any frame of mind to receive. it then by NO MEANS collect…but IF you are at REST and at EASE over what you see and are ok just before it enters then collect biko….all sized dicks are either harmful or sweet it depends on 2 things…..your frame if mind and HIS SKILLS……#my3cents

  5. Chill.. Physical thrill of being owned? Lol.. Bottoming for me is mostly about getting hit at that sweet spot. It’s more of an erotic activity than anything else. Well.. I speak for myself.

  6. Ya all who “Likes to Bottom” get in here! Great piece. Thanks Pinky for bringing this here. Bottoming for me is just about the pleasure. Most times, I like to give but sometimes, I like to take. And aint no modafucker owning moi! Yea I can be stubborn like that.

  7. *walks into the room* thanks pinkie 4 such a wondaful speech!!! *bends down to kiss pinkie * #runsoff #. Now sistas in d house wave ur hands and keep it clean down dia *walks out*

  8. This is the article of the year. Straight to Pulitzer. And then there’s 2 kinds of bottoms. The would-be, who reads good articles but retains a mental block, and the Genius, who is The Article Himself, or as Lady Gaga said, Born This Way…. … ..

  9. *yimu The whole thing is looking sweet n easy to do on print. Of course I’m not bending over if I’m not wanting to have sex so telling me to ‘relax’ is getting me to want to slap teeth outta u. Wait until the D pulls out and u hear this suction pop till u know bottoming is STILL not easy.

  10. Nicely done, thinking about it i can say it make me see things differently. I sure like to bottom but i am not a bottom. Even though some people like to feel like they are bottoms, i mean like real submissive. And talking about being owned, just makes me think of BDSM and i just shudder.
    All in all, i guess it will make me better at bottoming during sex.
    Where can i get me an Ear syringe? Maybe i will stop using my laboratory dropper.
    *okada, take me to that pharmacy down the road*

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