Pain in the Ass

My name is Alexander Cheves. My nickname is Beastly. I write about sex.

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I’m Peter, 31, live in London and I’m a bottom. I’m not sure if this is the right place to ask you or if you have answered questions like these before. I’ve recently come across your article on the advocate about “17 Tips for Happier, Healthier Bottoming“. I wanted to reach out because you seem like an experienced bottom and I don’t think I have ever read an article about bottoming as truthful as yours.

My questions are mostly about the fissures that you mentioned and about being able to relax and take any size dick. When I first started bottoming, I knew I was a bottom but sex was not enjoyable (doesn’t help that I started having sex with a guy with a massive dick). It would just hurt or not feel comfortable although the prostate orgasms were great.

I remember I had no resources and couldn’t find any answers online until someone recommended an anal training kit. I started playing with the different-sized butt plugs and slowly I was getting more joy out of bottoming. Sometimes though I still find it a bit difficult to just open up and take an above-average dick. The smaller ones go in just fine but a bigger dick is harder which I understand but even talking to friends I can tell it’s easier for some more than others.

My question mostly revolves around guys that can just take a dick easily. Am I just super tight? Should I be using my butt plugs more often to keep myself more open? Like maybe play with the butt plugs a couple of times a week? Is there any way to loosen up more or be more prepared for a bigger dick but still remain tight? I can see in amateur porn that guys who are regularly fisted are very loose and can take a dick much easier than I can (which makes sense).

You said in the article that fisting will take a long time but for example, if you are into fisting and you haven’t been fisted for a month, would you need more than one session to get back into it? So in the same case for me, to prepare for a bigger dick should I maybe practice a couple of times before doing the deed?

I’m sorry for all the questions, I’m just trying to understand how the bum works and what I should be doing to make things more comfortable and take away some of the fear. There are definitely times when I haven’t bottomed in a month and used no toys and then I have sex and I have some trouble at the beginning. I know it won’t magically slip in and it needs time, it just seems like it’s so much easier for some people.

My other questions are about fissures. Sometimes it seems like my hole is so prone to them and it links with the above stuff. If my hole is super tight and someone pushes in, I can instantly feel the tear. I can carry on having sex but it stings a little. Also, a guy will be teasing my hole and if he pushes slightly hard, I get a tear. I have wondered reading your article whether it’s to do with latex but usually, when my hole is being teased, there’s no condom.

I have also read a lot online about the harmful ingredients some lubes can have and I have switched to a new one recently with none of the bad stuff. I wonder if the older lube (liquid silk, which I love) has temporarily affected the lining of my rectal wall. When you have had a fissure before, do you actually wait months until you heal before having sex? Don’t you get them when you get fisted? I couldn’t even fathom my ass opening that much. 

Thanks for taking the time to read this and for all your help regardless. Your article is honestly great!

Hi Peter,

Give my love to London. It’s my favorite city. For tidiness, I’m dividing your message into two questions:

  1. Why does bottoming seem to be easier for other guys than it is for me?
  2. What can I do about all these stupid anal fissures?

Okay, let’s get started.

Why does bottoming seem to be easier for other guys than it is for me?

You seem to be laboring under the common delusion there are some magical men in the world for whom bottoming is easy and effortless. That is a delusion. There are no such men.

Do not compare yourself to porn. Porn is entertainment, and porn stars are acting. All the tedious, messy business of preparing for anal sex does not have much entertainment value (at least not for most people) so it’s tidily omitted — all the messes, failures, and half-starts are edited out. (That said, I think this content is valuable and I push filmmakers and TV makers to show it in my most recent column in Out Magazine.) Porn — even amateur porn — should not be seen as a realistic depiction of gay sex. But sadly many people do not realize this, and this is one reason why many queer men feel as you do. They think there’s a magical formula for easy bottoming they’ve just not figured out. There is no such formula. There’s only patience, time, and practice.

If you’re a beginner, it’s never a bad idea to wear a butt plug before getting fucked. To practice, I recommend wearing a small plug for as long as you can and even try masturbating with it inside you — do this at least once a week. And when I say to start with a small plug, I mean small. Think about the size of your pinky finger and slowly work up from there to larger plugs. An anal training kit is great for this.

All dry spells (periods without sex) require some mental, emotional, and physical re-training. If someone goes months without getting fucked, they will need to spend some time re-training and loosening up before jumping back into vigorous play. Even skilled fisting bottoms need to train a bit with butt plugs after a hiatus, and this is why most fisters regularly play with toys between fisting sessions — to give themselves practice (and because big toys are fun and feel good).

You probably want a prescribed regimen, a weekly to-do list, and I can’t give you that because I don’t know your body or what feels good to you. Stop approaching this problem from the angle of what you “should” be doing and start exclusively thinking about your pleasure. If playing with plugs and toys does not feel good, don’t do it. If big dicks do not feel good, don’t force yourself to take them. Do what gives you pleasure and only what gives you pleasure, and I promise your body will naturally advance in service of that. Because pleasure is truly what we are seeking, and skill follows to serve it.

Bottoming is hard for everyone, even porn stars. More extreme bottoming — bottoming for hands and monster cocks and large toys — requires years of training, practice, failures, and accidental messes. And no, there’s no way to stay tight and loose at the same time. When you’re getting fucked, you want to be loosened up. When you can’t mentally relax, your muscles are tense, your ass is clenched, and you’re “tight.” When you feel mentally comfortable and relax your muscles, you’ll be amazed how easily your ass can open, and that’s what we call “loosened up” or “loose.” Going from “tight” to “loose” is a mental change, not a physical one, and it’s a temporary state of relaxation — and, for some, euphoria — before your ass tightens back up again after anal sex is finished. The ass does not stay “loose” — perpetual looseness is a myth. The ass is elastic. Even after a hard fisting session, the ass closes back up and becomes tight again. If asses didn’t work that way, a significant percentage of young gay men would be incontinent, and they’re not.

Practicing with butt plugs (I offer recommendations for plugs in this post) will help your mind adjust to the feeling of your hole stretching and closing around an object, making you better able to relax when it comes time to get fucked. When I’m struggling with a big dick or a hand, I visualize my current favorite butt plug. In my mind, I have a very clear idea of the plug’s dimensions — it’s challenging, but I’ve felt it inside me many times. I know how it feels to stretch around it, and I know how good it feels when it finally slips in. I either compare whatever is going inside me to that plug or I imagine I’m taking that plug, and that usually helps whatever I’m taking — the huge cock or hand or whatever — to finally slide in. Familiarity with the feeling of your ass opening around something you can see and control makes it easier to open for an object you’re less familiar with because the sensation of your hole stretching and the “full” feeling of something being in you are the same. Keep a favorite plug in your ass for a little bit before your next hookup — while you watch TV or work on something. I recommend douching before the plug and then, closer to hookup time, doing a final check in the shower.

To steadily improve at fisting, it’s best to do one of two things once a week: a) practice getting fisted with a patient partner or b) play solo with plugs and other toys, gradually working up to bigger ones. But even if you don’t have fisting aspirations, the same regimen is recommended for regular bottoming: Schedule weekly sessions with soft and small butt plugs and dildos (again, gradually work up to bigger sizes) or regular hookups with a patient, gentle partner. If you can find someone willing to combine these two (opening you up with toys before having sex), you’re a lucky man. Regular practice is how we become confident at anything, including and especially sex.

But do away with the myth that bottoming is easier for everyone else. Everyone has to work at it, and everyone occasionally fails, gets hurt, and makes a mess. Even porn stars.

What can I do about all these stupid anal fissures?

Talk to a doctor. Some people are more prone to anal fissures than others, just as some people are especially prone to hemorrhoids. Everyone has some struggles in anal sex — I’m lactose intolerant and have a sensitive tummy in general. Your thing might be fissures. If these fissures happen as frequently as you describe, seek a gay-friendly gastroenterologist (GI), or ask your gay-friendly primary care physician to refer you to one. (This is why it’s so important to have a gay-friendly, nonjudgemental primary care doctor who knows your sexual activity.)

All ass play, including fisting, creates micro-tears in the rectal wall which are too small for the eye to see. These rarely bleed or cause pain and they generally heal quickly, but they are nevertheless gateways for infection. Fissures are larger versions of these and should be taken seriously depending on their severity. Mild ones usually itch, and you may have to quit sex for a little bit to let them heal. More severe tears cause pain and bleeding and these need medical attention. A doctor can help you discern which is which, so you need to find a good doctor ASAP. Yes, I stop for a few weeks to even a few months when I know I have a fissure because bottoming will only make it worse and will prolong my healing time.

This might seem counterintuitive, but training your ass can help with fissures. The biggest barrier between you and taking a monster cock comfortably is your mind, not your hole. Your ass is capable of astonishing feats once you train the mind to relax. Your butt can get fucked, punched, stretched, and so much more without injury or pain — with no fissures — once your mind and muscles are relaxed.

Training your mind to let your body reach that point is difficult, and this is why so many guys use drugs for sex. Chemsex offers a shortcut to bottoming headspace. Drugs like meth eliminate your mental barriers, and most recreational drugs also dull pain receptors, making them perfect to push yourself further than you thought you could go — and many people push themselves too far when they’re high and end up in the Emergency Room. I encourage you to minimize your reliance on these chemical shortcuts. You can reach this headspace naturally, but you have to commit to it and practice and understand that it might be years before you get there.

I’m not anti-drug, and sex and drugs are fun together. You’ll probably find that very vigorous sex is easier with drugs like poppers, pot, cocaine, and so on. Vigorous gay sex has always been chemically assisted in our culture — always. But try not to tie your ability to bottom to a particular substance. This doesn’t mean you need to exclusively have sober sex, but you need to have enough sober sex to develop your natural skill so that you’re physically able to bottom without drugs when you want to.

Meditation, restful sleep, mindfulness exercises, breathing techniques, physical exercise, and other practices are healthier and longer-lasting ways to train your mind and body to take dick without pain or injury. You won’t get there as quickly as you will with drugs, but you also won’t create a harmful drug dependency that could actually make you lose your sexuality forever. (Meth does that.)

Your mind is creating these fissures, not your butt. When you’re tense and uncomfortable, your ass is clenched. If your ass was relaxed — if your mind was relaxed — you would astonish yourself at how easily and painlessly you open up. Cocks, toys, and so much else will just slide in. That’s how awesome your butt is, but that’s also how powerful your mind is. It’s counterintuitive to not clench as something is going inside you — clenching makes us feel like we have more control. But if it’s going to happen pleasurably, you have to do the very opposite — you have to stop clenching, relax, and let go. It can be frightening and overwhelming to let go, to relax your muscles and surrender control, but that feeling is also incredibly beautiful. That feeling is what keeps me coming back to bottoming again and again, even when it’s a pain in the ass.

Be patient and practice. You’ll get there.

Love, Beastly 

hi there, I’m a 23 yo gay guy from Italy so pardon my English. For the last year and a half, I’ve suffered from hemorrhoids on and off and since I’m a bottom it has become a problem, I’ve stopped having sex regularly and closed in on myself which I know it’s stupid and dramatic, but I can’t help it. I’ve been using some creams which help a little, but my question to you is: any advice on the sex front? and do you know some bottom who got them surgically removed and has a happy sex life?
thank you for your time and for this blog

Hi friend,

I’m afraid I can’t be of much help. I’m not a doctor. There are so many factors I don’t know: your sexual history, your diet, your medical history, what surgeries (if any) you’ve had, and what meds (if any) you’re taking. And I wouldn’t know what to do with this information if I was told it. Adequate answers to medical questions are holistic, not isolated. You need to find a doctor who knows that you want to have receptive anal sex, and you need to speak with them candidly about these hemorrhoids.

As I did with our friend above, I’ll recommend anal sphincter exercises in your spare time, which are like the butt version of Kegels. They help you get more control over the muscles involved in anal sex.

If your greatest concern is the physical look of hemorrhoids, I recommend fucking in the dark. Hemorrhoid removal is tricky and there are risks. “There are ultrasound-guided artery ligations and devices specifically designed for hemorrhoid removal,” says Dr. Stuart Spitalnic, a clinical professor at Brown, in an article on Lifehacker. But he stresses that these procedures are not without risk. The hemorrhoids may come back, or you may have pain after the surgery, including pain with bowel movements. There’s also a risk of incontinence. And those are just the outcomes that have been studied. Dr. Spitalnic says: “Unfortunately ‘return to pleasurable anal sex’ is not an oft-reported research measure.”

If you don’t want your partner to see your hemorrhoids, you’re going to have to spend time talking to doctors about your hemorrhoids. Dr. Spitalnic doesn’t trust websites advertising rejuvenation because it’s too hard to tell which ones are scams. Instead, he suggests asking a surgeon you trust whether they can recommend someone who is experienced in more advanced techniques. And be honest with that person about why you’re asking and what you hope to achieve — pleasurable receptive anal sex.

Love, Beastly

I don’t know anybody else who could write about this: Life stuff made me step away from the fisting scene a number of years back. But as I started to return, I noticed a big shift, or maybe a split. There is a new erotic of prolapse and its cousin gaping. There were always punchfuckers and deep fisters, of course, but this seems new. I make no judgment but it does seem like this marks a different kind of eroticism. On the one hand, it reminds me of a straight guy I knew who used to tell his gf while he fucked her that he was going to get her pregnant now. They both got incredibly turned on in, I think, a slightly S&M way by there being a physical consequence of fucking. She would be transformed by his dick. I always related it to the bugchasing scene later. And now to prolapse erotics. Fisting is going to take you across a line so you will never be normal again. This is both terrifying and hot as hell. For me, most of the excitement of fisting was in the work of opening up, of you having to feel every twitch of fear, every millimeter of opening, and staying so attuned to each other until the moment you get in (or he gets in you). I loved taking cherries, and my hottest experiences were opening a top while his boyfriend held him from behind: I still remember the one top who started to sob when he finally let me past the sphincter while his boyfriend kissed and squeezed him: the fear and the trust was so primal it felt like he’d had an emotional breakthrough as much as a fisting one. But that’s just guys like me. Since I know you’ve written about your gaping experiences, you are probably the only writer who could talk to guys on both sides of the line and get them to speak honestly about what their practices mean to them. Just an idea. I would love to read what you might write. Thx.


It’s an interesting question: can fisting go too far? You’re right, these practices are relatively new. In fact, everything that we think of as “fisting” is only as old as the 1960s, when synthetic drugs and amyl nitrates started being widely and recreationally available. Fisting has always been a drug-assisted scene, even though many fisters might not readily admit that now. It’s likely that our species has always occasionally inserted hands into rectums and vaginas for pleasure, but our modern concept of “fisting” includes so much more than that: shoulder-deep fisting, double-fist punching, vigorous forearm fucking, extreme prolapsing. There’s no model (yet) for the long-term physical ramifications of these practices. Many of the men who prowled the original fisting clubs of San Francisco and New York died in the plague years.

Let’s call a spade a spade: fisting isn’t natural. A hand really isn’t supposed to be there. Fisting is tissue trauma. It may be controlled, gradual, erotic tissue trauma, but it’s still trauma, and the body reacts to trauma in many ways — generally with inflammation, and repeated inflammation increases an area’s likelihood for cancer and other problems. And since fisters are always trying to push the margin and try to outdo each other, particularly on social media platforms like Twitter, it’s worthwhile to ask how far we’ll go and how far we should go.

But everyone has sexual autonomy, so these questions can only be asked at the individual level, never collectively. No one’s limits can be imposed on me, and my limits do not apply to anyone else. As a bottom, I don’t do deep fisting, not because I don’t think it’s hot, but because I don’t think it’s safe. I’m fine riding a wrist and doing punches, but I don’t want a probe sliding into my intestines. I’ve fisted guys deeper than my elbow and it’s really fun, but I don’t need that as a bottom. That’s just my limit — for now, at least. I’m not interested in prolapsing — that, too, is just my personal limit. I don’t judge anyone for going further and pushing their bodies to extreme places for an erotic practice, and my perception of what is “extreme” has shifted dramatically over the years as I’ve seen more and done more. I will fight to the death for everyone’s right to do whatever they want with their bodies. I’m a strict hedonist — living for pleasure makes the most sense to me, and I can’t blame anyone who wants to trade longevity for pleasure. I know people who live hard and burn out bright and I would rather do that than play it safe and live to 80. I, like you, am incredibly turned on at permanent body modification and other physical “consequences” of BDSM — guys with wrecked holes and locked subs with tiny nubs — and my tattoo thing itself is a personal fetish practice. It’s hot to be branded by one’s fetishes — and hotter still, for some, to die for them.

Love, Beastly


  1. I hesitate to offer this tip because I’m not a doctor either, but one thing that helps a lot with fissures and hemorrhoids is to reduce anal irritation as much as possible in general, everyday life. And one way of doing that is to take fibre in the form of psyllium husk (for example, in the form of the product Metamucil or its equivalents) regularly. I take 12 g of Metamucil once per day in about 300 ml of water, and it’s helped me a lot. If you are taking medications or other supplements, take them at least 2 hours before or at least 2 hours after the fibre, as it can interfere with absorption. Alex’s advice is better: check in with your doctor or healthcare professional about whether this is something you might try.


    1. I have to second Chris’s advice here also. I also take a high dose of Metamucil twice a day and it works wonders for me, particularly since I don’t have a gallbladder. I didn’t know it helps with hemorrhoids and fissures, but decreasing irritation makes sense. I’ll add this to the post! Thanks, Chris!


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