How to Be a Better Bottom

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, 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 you tips.

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

PS: wish you still lived in LA 😛

You sound so nice. I sometimes wish I still lived in L.A. too. You very kindly broke up your questions into four clear and distinguishable ones, so I’ll answer similarly.


I know what “hurts so good” feels like, but I can’t quite tell if you’re commenting on the pleasure of bottoming or hinting that there’s a level of pain you’re having that you wish would stop. If bottoming sometimes hurts in the wrong way, you can train and stretch to make that better. I like 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. I can help with that. I didn’t improve as a bottom by having more sex; I improved when I started playing with toys and training my mind to recognize and enjoy the sensation of opening my hole. 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 practices: 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 down your body, like a gentle wave, gradually unlocking and opening the tunnel, all the way down to your anal sphincter (your hole — a circular muscle that takes a while to retrain for bottoming).

Take slow, deep breaths (four seconds inhale, four seconds hold, six seconds exhale). When we cringe or feel pain, our impulse is to tighten our muscles. When you do that, your hole will tighten and the pain will get worse. Training your butt is the process of learning to relax your muscles and your body even when you feel something uncomfortable.

Once that smaller size plug is easy to take, try a slightly bigger one, and work your way up. Some people like to keep them in for a little bit (some wear them for hours) but I like to slide them in and out — what some call “pistoning” — which more forcefully pulls and tugs my hole open. As you take larger and larger plugs, this will create a “gape,” which means your hole will start to stay open for a little bit after you pull something out of it. Mentally explore the feeling of your hole opening. Explore the sensation it delivers. You’ll learn that this feeling alone can offer a whole new kind of pleasure and intensity — some bottoms can orgasm from that feeling alone (I have). Learning to love this sensation will both reduce your pain and maximize your pleasure.


Diet changes and fiber supplements have changed the cleaning process for me. I added a fiber regimen to my diet (Metamucil) that has become part of my daily routine. Fiber clumps your poop together into a solid mass, which makes it easier to clean your butt. If you want more info on this, read my other post.

Putting better stuff in your body reduces the cleaning process. Quick and effective cleaning depends on what you eat, not how well you clean. The truth is, douching isn’t good for your body and steps should be taken to minimize it as much as possible (douching disrupts the good bacteria in your gut that is needed to process waste, and doing it too much can lead to chronic gastrointestinal problems). The best way to minimize the amount of time you douche is to take a fiber supplement and eat a lean, healthy diet — stay away from red meats, excessive animal fats, fried and high-fat foods, and so on. Consume more rice, veggies, lean proteins, and so on. A basic healthy diet.

Everyone’s body is different so everyone’s cleaning regimen is different. I know magical vegetarian bottoms who just don’t clean — they know when they’re naturally good to go. That is, sadly, not me. You’ll find a regimen that works best for you.


No, not all guys are into that. But some are. You have to communicate with your hookups what you want, ideally before they’re in your bed. If you really want someone to cum on your chest, tell them that before you decide to meet up. Make it a baseline requirement. I’ve stopped seeing my turn-ons as points of similarity among gay and bi men — instead, they are my own private arsenal, my personalized list of pleasure. I rarely ask a guy online if he’s into, say, stuffing his balls in my mouth. I just tell him: “Hey, when you come over, you’re going to stuff your balls in my mouth. I love that.”


That’s very kind and somewhat surprising. Half the time I feel like a cautionary tale on how not to live. I don’t know what you look like, so I can’t make any specific suggestions, but I will say that all the gym-going and “self-improvement” bullshit in the world won’t work if you don’t first find something in yourself, some core fire, some essence of yourself that you love and that you are willing to defend at all costs. Your body is the package, the vehicle, of the best things about you, but it is not you. You are a world unto yourself and filled with many narratives; treasure them and hold on to them. Your body is the front cover. Don’t be afraid if that front cover doesn’t always look its best. My oldest and most battered books are my most prized — they’ve lived great lives. The most important people in your life won’t judge you by your cover — they’ll see all that good stuff within.

As far as dieting, I have to eat well because I’m HIV-positive, so I’m higher-risk for everything (diabetes, heart disease, certain cancers, the list goes on). I don’t buy heavily into very restrictive diets — food, like sex, is meant to be enjoyed — but there’s enough medical science to know you don’t need much bread, sugar, sodium, alcohol, ultra-processed food, or red meat. Limit their intake.

If you want to be a gym bunny, you must start with a trainer. This trainer may be an experienced gym friend or a professional trainer you pay (the latter is better, but I know the costs can be steep). I’ve worked out (and worked) in all kinds of gyms, from the more affordable big-box chains like LA Fitness and Planet Fitness to luxury gyms like Equinox and have spent some grueling months in a CrossFit box. I’ve seen many inexperienced people get hurt. Even after years of training, I’ve gotten hurt. You want to start off with proper form and functional movements before moving on to more advanced workouts and heavier weights, and you can only do this with a decent trainer. You don’t have to have a trainer forever, but I do recommend having one for about a year.

Thank you for your kind words. I don’t do that much for the community. I answer questions and write about my life. I’m grateful that what I do is meaningful to you. You have great sex in your future. Enjoy the hunt.

Love, Beastly 

Like what you read? Please tip me. Every dollar helps this blog live. bove: David Castilla shot by Joan Crisol


  1. Great reply – it started out slow and mechanical, but got loving and beautiful at the end. Guess I need to check out your Patreon again to support your work/writing. Well done!


  2. I want to echo the first commenter–your writing on sex is some of the best I’ve seen anywhere–your honesty and your commitment are inspiring.

    I have a question similar to the first question in this post, about opening your hole. I love getting fisted, but no one has been able to get their hand all the way in. I try to use bigger and bigger toys for training, but the big ones end up just hurting the rim of my hole–feels like a lot of tiny cuts. Should I just keep trying and push through the pain? I would love to have a hand slide in and out–how do I get from here to there?

    Thanks so much for any advice you have!



    1. Do you want me to turn this into a blog post? I can recommend my own stretching techniques more fully in a post, but no amount of personal stretching replaces the value of a gentle, small-handed fisting top willing to work with you on repeat sessions and go slowly.


  3. Hey Alexander!

    I was wondering if you could go into more depth about your stretching techniques. I am so so close to finally taking that fist and I trust your advice!


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