How To Train Your Ass

Above: David Castilla shot by Joan Crisol

Anonymous Question:

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?


How does sex feel for you? That’s what matters. If you don’t enjoy sex because it hurts in the wrong way, your tops won’t either. I like when sex is a little painful (when it “hurts so good”) but there is a big difference between pain I derive pleasure from and pain that I can’t. If I’m miserable during sex (in the wrong way), my tops are also.

I’m a bit of an anal masochist and like getting wrecked. I like when it hurts. I have a feeling like that’s not what you’re talking about.

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, and you’re worried this is creating a less-than-great experience for your tops. Have you asked them? If they’re getting off, and you’re getting off, there’s not much more appraisal of sex to be had — you’re both enjoying it. Sure, you may be very tight, but if they’re enjoying sex and you are too, I can’t see much of a problem.

In time, you will learn to loosen up and relax. When you do, you will likely find that you’re able to go longer and harder and take larger dicks. Getting there takes time, along with some ass training.

I didn’t improve as a bottom by having more sex. I improved when I started playing with toys, training my hole, and enjoying the sensation of stretching it. Start with a small butt plug (not much bigger than two 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. Take deep, slow breaths. 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 in your ass.

Once that small size is easy to take, try a slightly bigger one. Some people like to simply keep them in, but I like to slide them in and out, gradually stretching and loosening my hole (what some people call “pistoning”). As you take larger and larger plugs comfortably, this will create a “gape,” which means your hole will start to stay open after you pull something out of it.

Mentally explore the feeling of your hole opening. Explore the sensation it delivers. Explore your breathing. Mentally scan down through your body, checking in with the different muscle groups, imaging a tunnel opening and unlocking from your hole all the way up your spine. Picture your hole opening around an object and try to open it more. There are many mental tricks to ass-training — you’ll find your own as you practice.


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


Diet changes and fiber supplements have changed the cleaning process for me. I used to take forever to clean — an hour or more — and now I take less than thirty minutes. I added a daily fiber regimen to my diet (MetaMucil) that has become part of my daily routine.

Putting better stuff into your body reduces the cleaning process. Quick and effective cleaning depends on what you eat, not how well you clean. Douching isn’t good for you, and shouldn’t be done too much. Douching disrupts the good bacteria in your gut that is needed to process waste. Doing it too much or too often can lead to chronic gastrointestinal problems. Minimize the douching process as much as you can by taking a fiber supplement. Fiber clumps your poop together into a solid mass, which makes it easier to clean out your rectum. If you want more info on this, read my other post.

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.

No, not all guys are into that. Just as not all guys are into cumming in an ass. The things you’re into are your sexual interests and it’s your job to communicate them to interested sex partners. 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.

As such, I have to communicate them. I have to tell other guys how to please me and what I like. If you want a guy to cum on your chest, tell the guys you talk to online (or wherever you meet them) that you want them to cum on your chest. That’s it.

If they’re not into that, that’s OK. They don’t align with your personal turn-ons, and you can decide at that point if you want to play with them or move on. My advice: Play with them, and be open to trying their turn-ons too. You never know what you might discover, what massive pleasures are yet unknown to you.


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.


That is 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 must say that all the gym-going and “self-improvement” in the world won’t work if you don’t find something in yourself, some spark, some essence about yourself that you love, a piece of you that you’re willing to defend and celebrate even when the exterior has had better days. I love going to the gym, but I love a deeper, inner me more. I have to. If I ever ignore that inner self by believing that the measure of who I am is how I look, I’ll plunge into a depression. I am so much more than looks and body. I often need to remind myself of that, and so does everyone else, and so do you.

I don’t buy heavily into restrictive diets. Food, like sex, should be enjoyed. But there’s enough medical science to know that you don’t need much bread, sugar, or red meat. These three things in excess cause longterm health problems. Don’t cut them completely (unless you’re vegetarian). Just limit their intake.

I think most health problems can be prevented with a healthy diet and regular exercise. Moving your body and being active prevents heart disease. Running relieves constipation and shreds clingy fat (and does a whole lot more good stuff for you too). Swimming provides full-body exercise with no impact. My best advice: Find something physical that you enjoy and set a schedule that’s realistic for where you are. Do it, say, three times a week. That’s a good starting point.

Trainers and coaches are wonderful and should be consulted in the beginning. If that means paying some money for their service for a few months, it’s money well spent. Someone needs to teach you how to do certain physical activities so that you don’t get hurt. I needed to learn how to work out at a gym from someone who’d been doing it for years.


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 😛


I miss Los Angeles sometimes. Thank you for your kind words, and thanks for reading my work through the years. That means more to me than you know.



  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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