Hurts So Good




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 would love your thoughts here. Thanks for all you do for the community.

PS: wish you still lived in LA πŸ˜›

Hi bubble butt,

You sound so nice. I sometimes wish I still lived in Los Angeles. You kindly broke up your questions into four clear and distinguishable ones, so I’ll answer accordingly.


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 you’re having that you wish would stop. If bottoming sometimes hurts in the wrong way, you can train and stretch your hole with toys. 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 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 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 down your body, like a gentle wave, gradually unlocking and opening the tunnel, all the way down to your anal sphincter (your hole β€” a very strong circular muscle that takes a while to train for bottoming).

Take slow, deep breaths (four seconds inhale, four seconds hold, six seconds exhale). When we feel pain, we instinctively clench and tighten our muscles β€” an animalistic “fight” response that all combative, violent animals share. 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 discomfort. That may take years, but with time and experience, you’ll get there.

Once that smaller 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 β€” what some call “pistoning.” As you take larger plugs, you 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 orgasm β€” some bottoms orgasm from that feeling alone (I have). Learning to love this sensation will both reduce your pain and maximize your pleasure.


I’m hesitant to say anything is “ideal” in gay sex. The douching industry has more or less sprung into existence over the last 20 to 30 years and has convinced gay men everywhere that their butts have to be perfectly shitless in order to be fucked.

If you want to avoid a mess, diet changes and fiber supplements will make a big difference. Many years ago 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, making it easier to clean your butt. If you want more info on this, read my other post.

Putting better food in your body reduces the cleaning process. Quick and effective cleaning depends on what you eat. 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 β€” 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 β€” 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 cumming on chests. 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 meet up. If you really want it to happen, make it a baseline requirement β€” you’ll only meet up if they agree to do that. I’ve stopped seeing my turn-ons as points of similarity among gay and bi men β€” 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.” If he says no, I move on.


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 that you love and that you are willing to defend at all costs. Your body is the package, the vehicle, containing the best things about you, which are internal. I see my inner stuff β€” my values, my talent, my mind, my story, my taste β€” as the real “meat” of who I am. My body is just the package. The package doesn’t always look as good as I want it to, and that often gives me great insecurity. On those days when I need a boost, I remind myself that I’m so much more than a body, and I fasten my confidence β€” or try to β€” to the inner things that matter. I encourage everyone to do the same.

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

If you want to be a gym bunny, you should 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 costs can be steep). I’ve worked out in (and worked for) all kinds of gyms, from the more affordable big-box chains like LA Fitness to luxury gyms like Equinox. I’ve seen many inexperienced people get hurt. Even after years of training, I’ve gotten hurt. You want to start with proper form and proper functional movements before moving on to more advanced workouts and heavier weights, and you can only do this with a trainer. You don’t have to have a trainer forever, but I do recommend starting with one and keeping them for about a year.

Thanks 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 


  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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