When I was little, my father would drag my sister and me out in the cold morning in camouflage outfits and orange hats to sit with him in a deer stand and practice shooting his gun. This was a necessity for a young boy in the South. While his tutelage never stuck, he might be surprised to learn that I still grew up to be a hunter.
All I need is a drawstring shoulder bag carrying my keys, wallet, cell phone, and a douching bulb for emergency visits to the nearest bathroom. Depending on the environment — a dive bar versus a dance club, a bathhouse or a play party — I might be wearing more clothes or less, but the target is the same: men and anal sex.
As gay men, a good portion of some of our lives will be dedicated to the art and craft of anal sex. It is one of my favorite ways to pass an evening and one of the most enjoyable parts of my life. At its best, bottoming is a mind-blowing and carnal experience that feels really good. At its worst, it is painful and unpleasant. Clearly there is a right and wrong way to do it, and a learning curve — few guys start off as bottoming champions. You need years of practice, and sometimes you need tips from someone who knows what he is doing. Hi, I’m Alex.
The tips in this slideshow progress from beginner bottoms to more advanced bottoms, so if you are just beginning your magical bottoming journey, the advice at the beginning may be more useful to you than those in the back. Enjoy the ride.
My name is Alexander Cheves, and I am known by friends in the kink and leather community as Beastly. I am a sex-positive writer and blogger. The views in this slideshow do not reflect those of Out Magazine and are based solely on my own experiences. As with everything I write, the intent of this piece is to break down the stigmas surrounding the sex lives of gay men.
Those who are sensitive regarding frank discussions about sex are invited to click elsewhere, but consider this: If you are outraged by content that addresses sex openly and honestly, I invite you to examine this outrage and ask yourself whether it should instead be directed at those who oppress us by policing our sexuality.
For all others, enjoy the slideshow. And feel free to leave your own suggestions for sex and dating topics in the comments.
Hungry for more? Follow me on Twitter @BadAlexCheves and visit my blog, The Beastly Ex-Boyfriend.
The first rule of gay sex applies to bottoms of all calibers: watch what you eat.
My vegetarian friends say that they hardly need to clean before sex — they simply use the bathroom and are good to go. This is because they consume a high fiber diet, which cleanses the colon. Meat-eaters like myself benefit from fiber regimens like daily Metamucil or Benefiber to keep our runways clear. In my experience, the best fiber regimens are those that come in powder form that you mix in a glass of water, and most contain psyllium husk — a natural fiber with multiple health benefits.
Sugar-free psyllium husk fiber can be purchased on its own, and I have even seen it sold in capsule form. I have not had the same good results from fiber capsules as I have from Metamucil, but some guys might. Metamucil is part of my daily routine.
Fiber is extremely good for you, and when it comes time to clean out your butt for sex, your stools will be compact and “together,” making cleaning considerably easier. Loose, runny stool is a nightmare to clean out.
Too much fiber can dehydrate you and cause cramps and hemorrhoids, so do not take more than the recommend dose. Make sure you drink plenty of water to stay hydrated — something every healthy person should do anyway.
Some guys can simply tell when they’re good. These men have an uncanny ability to just know without a shadow of doubt that their colons are clear and ready for a pounding, no douching required. These men are mysteries to me. I respect them the way I respect firefighters and contortionists. I cannot quite believe they can do what they do, but they do it nevertheless.
I always have to make sure things are good down there before having sex. Some guys do a pre-sex check with a lubed finger, but I do not trust my fingers, which are shorter than most of dicks I want to take. So while a finger check might be convincing for some, I always fear there may be stuff further up. This is why I almost always clean out beforehand.
Let’s face a fact: douching, using an enema, and frequently cleaning out the ass would probably be frowned upon by most healthcare specialists. Some consider it an acceptable occasional practice to relieve constipation, but most would frown at the idea of douching as frequently as every week (or more).
I choose to clean frequently because I like to have mess-free anal sex, and have not had any problems from excessive douching. Many straight people have this idea that gay sex is a messy affair, but as Dan Savage wrote in his book American Savage, “You don’t have anal sex with an ass full of shit for the same reason that you don’t have oral sex with a mouth full of food. Because it’s uncomfortable and it makes a mess.”
Most guys have different cleaning methods depending on the kind of sex they want to have. Most guys begin cleaning in the shower with water and a finger, and for some that is enough. Many guys move on to using a douching bulb or enema. This works for most guys too, although douching bulbs and enemas will not clean your ass as deeply and thoroughly as hoses and shower attachments can. I use a hose — a shower attachment with a short, smooth nozzle — with slightly warm water and low pressure (high pressure is not recommended — ouch). These different cleaning methods have different benefits and different risks which I will go into in the following slides.
You should never rush the cleaning process, especially if you are a beginner. Cleaning out is more than putting water up your butt. Good cleaning is also about relaxing your ass muscles and getting comfortable with the feeling of being penetrated before you start play.
The brand Colt makes great douches and cleaning devices, and their products can be found at most sex stores, and they are not too expensive. A good douching bulb will have a large rubber bulb and a smooth plastic nozzle. If you use one in the shower, lube up the nozzle with silicone lube, which will not wash off in water. Gently and slowly stick the nozzle up your butt and gently, slowly squeeze the bulb.
When the bulb is mostly empty of water, gently and slowly (I will repeat those two words often because all cleaning requires you to go gentle and slow) pull the nozzle out. Hold the water in your ass for a few seconds, then relax and release it into the toilet.
Chances are good that you will need to do this more than once. I know some guys who are good to go after one squirt. Since I prefer rigorous sex, I will usually douche three times at least.
I cannot stress this enough: take your time with cleaning. Do not rush it. Not only can you hurt yourself if you rush the process, but a rushed cleaning job will probably not get you completely clean. After some practice, you will discover a frustrating truth: whenever you think you are all set, suddenly that second anal chamber will open and you will have to douche again. If you have time, clean once, then wait about thirty minutes and clean again.
The trick with cleaning with a douching bulb is to hold the water in your butt for a few seconds. (I do body squats in the shower to push the water up a little deeper.) That same rule of thumb does not apply to cleaning out with a hose or shower attachment.
When you use a hose, relax your ass and let the water run out freely. Do not try to hold it in. Make sure the water is moderately warm, not hot, and relax your butt. Hold the nozzle in for a few seconds, allowing the water to run out gently, then pull the nozzle out. Repeat until clean.
Douching with a shower attachment gets me a more thorough clean, typically faster than with an enema. I have experimented with different nozzles, but generally the basic plastic or metal douching nozzle that you get from a sex supply store works great. I stole my first nozzle (a smooth, stainless steel one) from a shower room at the Armory in San Francisco — the filming studios for Kink.com (sorry guys). Since then, I have used nozzles that are longer, slender, and made of smooth PVC or rubber that clean deeper. I must caution that these are for more advanced bottoms. Deep cleaning is not without its health risks (more so than cleaning your ass with an enema) but it gets me better prepared for hours of hard sex, ass play with big toys, and fisting.
I have a delightful condition I call “classic bottom syndrome.” I have learned to enjoy the feeling of getting fucked and having stuff in my butt so much that my brain now links orgasm with anal. You could say that my pleasure focus point has shifted from my dick to my butt. I admittedly do not masturbate as much as I used to, and it takes me much longer to cum when I do not have something in me.
Not only are anal prostate orgasms more intense for men, but some, like myself, learn to love the feeling of the anal spinchter (the circular muscle that opens and closes at the base of the colon, which is clenched tight and shut for most of your life and opens when you have to use the bathroom) opening around an object, whether it be a penis, a butt plug, or hand. The opening and closing of this muscle on its own can be very erotic.
I discovered this sensation through toy play. Gay sex tends to focus only on the prostate, since a good top is basically rubbing the prostate with his dick. When my ex-boyfriend and I decided to start playing with toys, I discovered sensations that I had never experienced before. He started pushing a small butt plug in my ass during foreplay, and I learned that the feeling of being opened can be just as intense as being fucked.
Toy play has made me a better bottom and, for many guys, is the gateway to becoming more comfortable with sex. Toys open you up and get you used to the feeling of penetration at your own speed.
Most of the veiny, “ultra-realistic” dildos in sex toy stores are not designed for anal. Most of them are too hard, and many of them have a rough, porous texture.
These are novelty items. You might purchase one because it was modeled after your favorite porn star’s massive, 12” dick, but it is probably not something you want in your butt. Those synthetic, sculpted veins can be sharp and very painful. Remember that the colon is lined with thin, delicate tissue that is easily torn and punctured. Smooth toys work best.
My favorite lube is Pjur Back Door silicone lube. I know this after experimenting with every kind of lube imaginable, from lotions to kitchen ingredients to Elbow Grease and more. Browse my list of must-try lubes in “30 Liquid Assets Every Gay Man Should Know.”
A good lube makes a big difference. Many guys prefer spit — I do — but spit typically will not work for rough sex or extended play. When I go hard, I use silicone lube. Silicone lube is messy and stays slick forever, meaning it can sometimes present clean-up problems (avoid touching door handles), but it works fine with latex and non-latex condoms and keeps your ass lubed up longer than water-based lube. Silicone lube can also be used in the shower, since it will not wash off with water, meaning you can use it for douching and for shower sex.
I have a latex allergy. This means that when have sex with condoms, I use SKYN non-latex condoms [http://us.skyncondoms.com/products/#skyn-large], which are just as effective at latex condoms at preventing STIs. When I get fisted, I use non-latex gloves.
My sex life did not really begin until a friend told me he has a latex allergy and suggested maybe that was my problem as well. The very next day, I went out and bought my first box of non-latex condoms. My life was changed.
Latex allergies are more common than you might realize. If you are repeatedly having uncomfortable sex and your hole feels like it is burning or badly irritated every time you use latex condoms, try a non-latex condom made of Polyisoprene (read: not condoms made from lambskin, which does not protect against STIs, just pregnancy).
It took me a long time to stop asking guys during sex to pull out and check their penises for shit. Few of them would have cared if there was any, but I did. In my mind, I could not imagine having sex with a dirty hole. This paranoia has ruined sex for me several times in my life and frustrated tops who knew what they were getting into — literally. It is butt sex, after all, and if you do it enough, you are at some point going to encounter traces of that other thing the ass does.
The best tops may prefer a clean hole, but most of them know that sometimes the body behaves outside of one’s control — even after an hour of cleaning. Whether you are a total top or a total bottom or totally versatile, be less afraid of shit. It’s going to happen.
Keep an eye out for blood. Every time you have anal sex, you get micro-fissures. These are tiny tears that may not bleed at all and will probably not cause any pain, but they are still gateways for HIV transmission. However, when you see red, it is a sign that you have gone too rough or perhaps have not used enough lube, and it is time to stop.
If you are a recreational bottom, this will happen at some point in your life. Do not live in fear of bleeding — stress and sex phobia are more unhealthy than most other ailments — but know that your likelihood for anal injury is higher if you are a cock-loving bitch who loves getting pounded.
I’m a cock-loving bitch who loves getting pounded, and I have had anal fissures more than once in my life. An anal fissure is a non-serious rectal tear that takes a frustratingly long time to heal — usually several months — but is generally not considered any more severe than a hemorrhoid. Again, fiber will aid the healing process of both these common ailments that befall bottoms.
While anal fissures are quite common, some ass injuries can require a trip to the hospital. If you puncture your colon or are bleeding badly and in extreme pain, get yourself to an Emergency Room as soon as possible. Ass injuries are not to be scoffed at. But I must also stress that if you have smart, sane, and consensual sex, and only push your limits within reason without exceeding your abilities, you can enjoy bottoming for years without problems.
We now live in an age when PrEP gives HIV-negative men and women extra precaution against HIV transmission — a precaution that, according to every statistic available, is more dependable than regular condom use. But while PrEP has the potential to lower HIV transmission rates among the people who can get access to the costly medication, rates for other STIs like chlamydia and gonorrhea and syphilis are soaring among gay men.
I do not shame barebacking because most of my sex is bare and condom-less. I am a piggy guy who loves male bodily fluids — cum, sweat, piss, spit, in that order — but I also know my sex practices involve STI infection. Most clinics and LGBT centers say that sexually active gay men should receive a full-range testing every three months. Since I am having regular bareback sex, I get tested every month, no exceptions.
Getting tested every month is not a preventative healthcare practice, but a responsive one. While I agree that most responsive healthcare regimens are less healthy in the long run than preventative care — our overmedicated society is evidence of that — I concede here that monthly STI testing and PrEP jointly face a present reality: gay men are having bareback sex, and lots of it.
The thinking goes that if you get tested regularly for everything then you will catch STIs and treat them before they become bigger problems (and let’s face it, if you are a sexually active gay man, you are going to get an STI at least once in your life). This thinking does not work so well for HIV, since HIV can stay in the body for months before it registers on an HIV test, during which time the virus is very transmissible. But for men on PrEP who make the decision not to use condoms, monthly testing is the minimum degree of self-care that you should practice.
While bareback pigs frequently incur shaming and anger from people both in and outside the gay community, stigmatizing a lifestyle does little to address its reality. Barebacking is in, and the vast majority of homos I know do it. This fact is probably a nightmare to public health workers and a damning picture of gay promiscuity to sex-phobic and homophobic people all over the world, but neither of those opinions change the fact that many of us (I am tempted to say “most”) are fucking bare and not apologizing for it. So rather than cast blame, the wisest response is for me and every health care worker and conscientious gay man to urge guys who bareback to get tested as frequently as possible.
The previous slide automatically leads to my next topic: being a cum dump.
Being a cum dump means different things to different guys, but generally a cum dump is a guy who, for a certain, predetermined amount of time, takes anonymous loads in the ass from as many guys as possible. Cum itself for many guys is the fetish, so being a cum dump kind of the ultimate goal for someone who fetishizes cum itself. Some guys take this to risky extremes and will stay blindfolded on a bed in a hotel room with the door unlocked for a day or two (not recommended, since this can lead to bodily harm and loss of valuables and property). For others, being a cum dump may simply mean being a bareback bottom at an orgy or going to a bathhouse or sex club and taking as many loads as possible.
Whatever being a cum dump means to you, if you choose to do it, plan in advance to receive a full-range testing two weeks after and a few weeks after that. If you are planning to be a cum dump for a lengthy amount of time, you may need to clean deeply (with a hose or shower attachment) and, if you decide to be a cum dump away from home and the privacy of your home bathroom, you may want to carry a douching bulb with you for emergency trips to the nearest restroom.
There is a trick I learned at the Folsom Street Fair a couple years ago. If you take Imodium or some anti-diarrhea treatment (and you do not, in fact, have diarrhea) it will stop everything. After cleaning once or twice, the treatment will stop your body’s poop-making processes, especially if you take the maximum dosage, and keep you clean for a long, wild evening.
Different gay men have argued the health benefits of doing this. It is probably not the best thing to do, but neither is excessive cleaning or really rough sex, which can cause hemorrhoids and fissures and other ailments. Gay men do not always make the healthiest choices — in fact, my experience shows that we tend to make a lot of unhealthy ones — but we have perfected the art of fucking.
There is a caveat to this trick: it might not work perfectly. While I have generally had good success with Imodium, over-dosage has messed up my stomach and actually caused me to have a bowel movement. It can make you feel cramped and give you a stomachache, especially if you eat food after taking it. My backup plan is to always carry a douche in a drawstring bag, but this is not always doable. I have cleaned in strange places — in the bathrooms of clubs and bathhouses, in the showers at truck stops, and once in the bar owner’s apartment over the club (the music was pounding through the floor below).
Fisting — inserting the whole hand into the anus — tends to draw gasps from people who are not into it, gay men included. Regardless, fisting is one of the most intimate and erotic sex practices I have ever experienced. Guys into fisting understand pleasure and ass limits in a way that few others do, and theirs is a fraternity unified by red socks and red hankies and a gleeful love of all things ass.
There are many books and websites on how to fist properly — Fist Me! The Complete Guide To Fisting by Stephan Niederwieser is a great one — but the biggest challenge for someone with dreams of being a fisting bottom is the hours of patience and practice that must come before he finally pushes past the knuckle. You will probably not take his fist the first time you try, and that should not be your goal. Get comfortable, first and foremost, with getting fucked. Then start with anal toys, gradually working up to larger and larger sizes.
When you feel you are ready to get fisted, only do it with someone with years of fisting experience. You do not want an amateur or beginner playing in your butt. Not only is getting fisted a sensory overload, but it requires more trust and vulnerability than perhaps any other sex act (with the exception of various kink and BDSM scenes). Improper fisting can cause severe rectal damage and send you to the hospital, so only explore fisting with someone who knows what they are doing and someone who is sober.
Go slowly and use lots of lube. You cannot use too much lube in fisting. While Crisco is certainly the most old-school fisting lube, J-Lube and the French product Fist Powder Tech are also recommended. Try different lubes to figure out which one you like the most.
Sex drugs are invariably part of our world, so it would be a disservice for me to say “Don’t do drugs” and let that be the end of it. I am not sweepingly anti-drug, although I believe certain substances — heroin, meth — should be avoided. Drugs come with a plethora of risks all on their own. They can lower your ability to fight infection, may diminish the efficacy of your antiretroviral medication, and can obviously cause severe addictions along with a slew of harmful side effects.
You will probably do drugs at some point in your life, or have staggeringly drunken nights, or both. If you choose to have sex on any drug or mild-altering substance — alcohol being one of them — know that substances can limit your ability to detect pain or know when your butt has had enough. I have friends that have used drugs to push their ass boundaries, gone too far, and wound up in the hospital. And I know at least two fisting bottoms who died of drug overdose at very young ages.
If you choose to do drugs, remember that the most common sex drugs — Ecstasy, Molly, GHB, and the like — will act as accelerants. They will probably affect your stomach, especially if you have not eaten, and quite commonly will make you have a bowel movement. If you are able to carry a douche or enema with you, you might want to at least do a squirt after you take a hit.
I must stress that regardless what you choose to do, sharing needles and injecting any substance into your body is an extremely high-risk practice that invites Hepatitis, HIV, and other infections. Steer clear of injection drugs.
Some tops like a submissive bottom, others like a dominant one. You will only learn this through communication — so communicate! Even if you are not versatile sexually, there are many benefits to being a versatile bottom, able to ride it when he is feeling tired and able to shut up and take it when he is feeling rough and in charge.
There are different exercises you can do to train your hip muscles and lower back muscles to make you a better bottom. Some great ones are covered in David Artavia’s article “9 Exercises Guaranteed To Make You A Better Bottom” on Gayety.com. I would also add that, since the spinchter is itself a circular muscle that can be stretched and exercised like all other muscles in the body, certain ass-training toys like kegel balls, Ben Wa balls, and smooth butt plugs can be used to exercise your hole and make it better at opening and clenching.
There is this absurd idea that bottoms do not do any of the work in sex, which is false. Not only do bottoms typically have to clean out beforehand, but we also set the tone and speed of sex and control its advancement. Good sex is about exchanging power and playing with different degrees of dominance and submission. You must read each other’s body language and please each other in different ways. Part of your job as a bottom is to take the dick, but the other part is to please him and give him attention. This second task has no pointers or rules, because every top is different and has different things that get him off.
There is a lot of bottom shaming in the world. Invariably bottoms are the ones that get teased and mocked the most in gay discourse, and tops glorified. There is a very ugly, misogynist, heteronormative reason for this that invariably comes from the idea that guys who fuck are a step closer to being “straight” and even “male” while guys who get fucked are automatically feminized, degraded, “gayer,” and a step closer to “women.” The deeply misogynist and homophobic tones of this discourse should not be surprising, since misogyny is no stranger to gay culture and some of the worst homophobes in the world are gay men who direct this hatred at themselves and their own kind.
When I first came out of the closet, I announced myself as a top. I did this so that the straight men around me would see me closer to being an equal. I was afraid of femininity and afraid of what I perceived as gay stereotypes and “flamboyance,” and I did everything I could to appear differently — including calling guys “bro” and topping only (badly, I might add).
My topping phase lasted through two brief college relationships before I accepted a truth that I had known all along: I was a bottom. And not just any kind of bottom. I wanted to be unable to sit afterward. I masturbated to the idea of using Preparation H after a rough night to decrease the swelling. I wanted my hole wrecked.
When I finally tried to carry out these fantasies, I could not take anything bigger than a pinky finger. But I worked at it and learned by body and made mistakes, and now I can enjoy hours of marathon sex and go exercising the next day — no Preparation H required. I am a bottom without shame or apology. I love my butt, I love men, and I love men being in my butt.
The next time you go hunting, do so with confidence and self-love. You are not lucky to find a good top — a good top is lucky to find you.