Ask Beastly: How Do I Become a Better Bottom?

From training your hole to loving yourself, here’s what new bottoms should know.

I’m Alexander Cheves, and this is LOVE, BEASTLY—a blog about sex, feelings, and manhood. It’s written primarily for men—gay, straight, bi, MSM, or just curious—but some readers are women, and some don’t fit into categories. Everyone’s welcome here.

I answer real, reader-submitted questions about sex, kink, desire, and intimacy.

Want to ask something? Email your question to askbeastly@gmail.com. I never share names, emails, or anything personal—every question is answered anonymously, always.

This post includes a free preview. Subscribe to unlock the full answer and access every post dating back to 2013.

---

Hey Beastly -- 

First of all -- love your work and have been following you for years. Love everything you stand for and the message you share with the community (and beyond). Plus, your IG is hot AF!

OK, a few (anonymous) questions for you, would love your thoughts and answers, but I'm sure you'll get a bunch from folks as well:

1) I have a big ass -- Puerto Rican big booty -- and I want so badly to be a good bottom. I've only been sexually active in the last year (and I'm 26, but that's another story), and whenever I do bottom, it "hurts so good" -- I feel like I'm very tight and don't know if that's always a good thing. What do you think?

2) With bottoming, I know cleanliness is ideal AF. What are some of your best tips?

3) I haven't been able to get a guy to cum on my chest even though I want it so badly -- do you think maybe not all guys are into that? I find it hot to see a guy cum and actually see it, but maybe it's just my experience where I feel alone there.

4) Lastly, I'm definitely not in love with my body and want to self-improve and love it more. Any advice -- I feel like you have been transforming for self-betterment lately, and I would love your tips.

Again, you're the jam, and I would love your thoughts here. Thanks for all you do for the community.

PS: wish you still lived in LA :P

Hi bubble butt,

I sometimes wish I still lived in Los Angeles. You kindly divided your message into four clear and distinguishable questions, so I'll answer them accordingly.

1.

I know what "hurts so good" feels like, but I can't tell if you're commenting on the pleasure of bottoming or hinting that there's a level of pain that you wish would stop. If bottoming sometimes hurts in the wrong way, you can train and stretch your hole with toys. I like it when sex is rough (when it "hurts so good"), but there's a difference between pain-as-pleasure and just pain.

I'm reading your question as describing a lack of experience, and therefore a lack of the ability to mentally and physically open up and relax your butt. In other words, I'm reading the "hurt" as the second kind of pain—actual pain that you wish would stop.

I didn't improve as a bottom by having more sex; I improved when I started playing with toys and training my butt and training my mind to recognize and enjoy the sensation of my hole opening. Start with a small butt plug (not much bigger than three of your fingers and about as long) and slowly slide it into your hole. Use lots of lube.

If you start to feel pain or discomfort, stop and focus on your breathing. I recommend a mental exercise, one borrowed from meditation: Visualize a tunnel running from your throat to your hole. It's clenched tight. You have to breathe and relax your body, starting at the top of the head and moving slowly down your body (also called a bodyscan technique), like a gentle wave, gradually opening the tunnel, all the way down to your anal sphincter (your hole, a strong circular muscle).

Take slow, deep breaths (four seconds inhale, four seconds hold, six seconds exhale). When we feel pain, we instinctively clench and tighten our muscles—an animalistic "fight" response. When you do that, your hole will tighten and the pain will be worse. Training your butt is the process of learning to relax your muscles, even when you feel discomfort. That may take years, but with time and experience, you'll get there.