"Let me state this at the beginning: I am a bottom. A marathon-sex, Preparation-H, take-dick-like-a-champ bottom. I tend to outlast tops. Ten tops looking for a bottom? No problem.
Why, then, am I writing this article? Because there is no one better to ask about topping than a bottom. And although we generally present these sex roles as fixed, here is an unavoidable truth that most gay men of a certain age will tell you: Even if you start off batting for one team or another, most of us become versatile over time.
Sure, there are a few lifelong total tops out there, but many gay men begin to see the silliness of closing ourselves off to an entire half of the sodomy experience. I have found myself in an increasing number of situations where I want to make the men I like to feel good. This means rising to the occasion — literally — and topping them.
Most tops could use a lesson on how to top better, and most self-identified bottoms will at some point be at the altar of his ass, ready to worship but unsure of what to do." - Alexander Cheves
1. Have an anatomy lesson.
A boy butt is so much more than a hole you stick stuff into. Good bottoms know this. Many tops do not.
Many guys envision the butt as a tight, squishy chute — an organic masturbation sleeve. But the ass is more of a tight, squishy chamber with dimensions and curvatures that vary slightly from man to man. There is a definite curve to it, and the first chamber leads to another chamber, which leads to the small intestine.
You probably know about the prostate, that hard little walnut halfway inside the ass that will be above or below your dick, depending on whether you’re fucking doggy-style or missionary, and which feels amazing when rubbed. But there’s more!
There is a bladder down there that you cannot ignore — feeling the need to pee halfway through sex is very common — and there is a very strong muscle called the anal sphincter, a circular muscle at the base of the colon (the “hole”) that clenches tight for most of our lives and opens and relaxes when we poop and when we take a dick.
The anal sphincter is one of the strongest muscles in the human body, and it will present the biggest challenge for new bottoms, as learning to relax this muscle on command takes practice.
There is a lot down there, and a good lesson about how it all works, along with a general primer on how the body processes food and what triggers the digestion process, will help you navigate it better. Updating your mental list of bowel movement stimulants — drugs, coffee, the act of eating — will keep you aware of butt mechanics. Knowing where your dick is going is important.
The guy you are fucking is more aware of all this stuff than you are, because it’s his body, and he has probably cleaned out beforehand and has a clock running in his head of how long it will be before he might have to clean again.
Get on his level. Learn some anatomy.
2. Stop calling experienced bottoms “loose.”
The idea of being “loose” is something implicitly linked to shame. How many jokes have you heard about loose butts and the guys who reportedly have them?
It’s pretty cruel: You’re a new bottom and your ass is “tight,” meaning you have not learned how to train the anal sphincter to relax or open on command. Your tight ass might feel good for tops, but it makes sex more painful for you, and it will take you longer to get used to the feeling of getting fucked.
But you practice, and you get better. You use toys and learn ass-stretching techniques and practice with Ben Wa balls and kegel balls and butt plugs, and gradually you learn how to take dicks like a champ, which inevitably means learning how to open and close your hole (your anal sphincter) on command.
Then some asshole top comes along and says he doesn’t like loose bottoms — or worse, he calls your ass loose. He’s essentially shaming you for getting better at what you enjoy doing.
The idea that “loose” holes are weakened or overworked through too much sex is simply false. If you can train the sphincter to open on command, you can also close it, and this means the muscle is stronger now than before. Like any muscle, if you work it, it strengthens. Guys get called “loose” when they’ve learned how to flex — and have strengthened — a muscle.
If you have marathon sex and have been opening that muscle all night, it will get tired, and then it will open more easily, and you will start to feel loose — a feeling that can be hot for bottoms as for tops who like used holes (a fetish for many people). For some bottoms — myself included — this temporary, post-marathon-sex “loose” feeling is part of the fun, as is the act of nursing your wrecked hole the next day. It is erotic on a different level that fist pigs and toy pigs can understand. But even at this point, I would not appreciate being called “loose” in a derogatory manner, because there is nothing shameful about bottoming all night.
Honestly, if a guy’s sex skills are so poor that he needs a tight, novice ass to get pleasure out of sex, that’s his problem, not mine.
3. Alternate your speed.
Many tops simply don’t know how to fuck. They think sex is about sticking their dicks in and pounding like a machine.
Unless the guy you are fucking is looking for that kind of sex, he will probably tell you to slow down or stop.
The sphincter's natural state is being closed tight, which means you have to go slow at first while he gets used to it. Once he relaxes and gets comfortable and starts to enjoy your cock, only then you can get a little rougher.
As with fisting, the best way to help a guy’s ass relax is with a gentle, steady, in-and-out rhythm. He will tell you how slow to go, and you will know when you can speed up — his body will relax and his hole will automatically open. When this happens, that doesn’t mean you can immediately start jackhammering, but it does mean that you can add in a few harder, faster thrusts between slower, gentler ones and see how he responds to them.
If you are fucking doggy-style and he likes it and starts backing up into you, you can increase your speed. If you’re fucking him missionary-style and he nods or pulls his legs back or grabs your hips or your back and pulls you into him, you’re good to go.
4. Get over your fear of dirty butts.
A few weeks ago, I was preparing for a hookup. Right before I hopped in the shower to clean out my ass, the top messaged me: “Make sure you clean that ass really good. I don’t like dirty butts.”
Automatic block. Discard pile. Rejected.
I don’t particularly like the word “dirty” to imply the presence of shit, which is something the ass naturally produces and not something to be feared. “Dirty” implies shame, and there’s nothing shameful about the way the body functions. But most guys, including myself, will not bristle up at the word’s use. Most of the time it is said without judgment.
This being said, do not tell your bottom to clean out well. Saying that will only add to his nervousness about being clean. Unless he has expressed that he’s into shit, it is generally assumed that he will have to clean before you guys play — unless he is one of those mystifying and magical bottoms who knows when his ass is simply ready to go, no cleaning required.
When playtime comes, he will probably be anxious about the possibility that his ass isn’t spotless. You telling him to be spotless will only increase that anxiety and probably make your sex less enjoyable.
Good bottoms — as well as good tops — gradually learn to lose this fear. Yes, you can clean your ass thoroughly before play, but remember that the body is the body and the ass is the ass, and you are only able to control it to a certain degree.
You can manipulate its function through anti-diarrhoea pills and you can extend your ability to use it with poppers and drugs, but at some point, the body will process waste and do what it needs to do. If you spend enough time in the butt, you are going to encounter evidence of that other function beyond delivering mind-blowing sensations that the butt performs.
If you’re fucking him and encounter some shit, don’t freak out. Responding with disgust or revulsion can really hurt his feelings. It’s an ass — it’s going to happen at some point.
Gently tell him about it, and together decide what to do. Either you will stop and let him clean out, or you will continue. Most bottoms will want to stop and clean, either because the sex has become uncomfortable or because they assume tops want to fuck a clean ass. If you do not care about shit, tell him so, and let him know that whatever he chooses to do, you’re into him — literally.
5. If you use condoms, be patient and understanding when he needs a break.
I must be honest here: I rarely use condoms.
But unlike many bareback-only pigs who scoff at rubbers and refuse sex with guys who prefer them, I will play with someone who chooses this precaution — along with as two conditions are met: The condoms must be nonlatex polyisoprene (not lambskin, which does not prevent sexually transmitted infections) and we must use silicone lube.
These conditions exist for two reasons. One, I have a latex allergy, so nonlatex condoms are a must. Two, silicone lube is the slickest, most long-lasting lube you can buy, and will not dry up like water-based and hybrid lubes will.
I choose to only use silicone lube because condoms, regardless of what they are made of, inevitably cause friction in the butt and will begin to wear. Silicone helps me go longer with a condom.
Let’s face a blunt fact: Sex with condoms is less comfortable than sex bare. For me as well as for many bottoms, it is harder to get fucked as long or as hard with a condom as without one. This being said, diligent condom use is unquestionably a safer sex practice. PrEP only prevents HIV transmission, and rates of other STIs are skyrocketing among gay men. If anyone shames you for using condoms, they’re an idiot. One’s sex practices are a personal decision, and no one should pressure you to do something you do not want to do.
But when the condom starts to wear and your bottom needs a break — either to replenish lube or change the condom — do not get frustrated.
6. Worry less about your size.
Experienced bottoms will tell you that a top with less endowment who knows how to fuck well is way better than a well-endowed monster who does not.
The best lays of my life were with guys who weren’t massive but knew how to use what they had. They had confidence and charisma, and they loved being in my butt. Confidence and charisma will take you far — these characteristics are sexier than perhaps any other. The lesson I’ve learned from these tops as I have begun my own journey into topping is this: If you make it feel good for yourself, it’s going to feel good for him too.
7. Use your tongue.
There is a world of difference between a good rim job and a bad rim job. Some guys just dive in and start licking. This can be hot, but remember that saliva dries out the skin, so if you repeat the same motion repeatedly, your rimming will begin to wear on him.
When I give a rim job, I make patterns that he can focus on as he gradually relaxes: stars, spirals, zigzags. I also vary up what kind of “tongue stroke” I deliver. Light, quick taps on the hole with the tip of your tongue will deliver one kind of sensation — a quivering, mind-blowing one — while deep, plunging thrusts where you try to stick your tongue in as far as it will go will deliver a very different one.
8. Use your breath.
A good rim job involves breath.
Blow on his hole. Remember that breath has different temperatures which will deliver different sensations. The breath you produce when you make a small O with your mouth and blow as if you are blowing out a candle will typically be cooler in temperature. The breath you make with an open mouth, from the back of the throat, will be warmer (think about when your hands are cold and you blow on them to warm them up).
The first kind of breath will probably make him tighten up as you give him a cool rush of air. The second kind of breath will typically make him open up. Just as with heat pads on muscle, the skin naturally relaxes under warmth.
9. Use your teeth.
There is some debate among my friends about whether or not a good rim job involves teeth or not. I love teeth, just as I love the sudden, sharp prick of stubble on my hole. But I will admit that teeth, like stubble, should be used sparingly — once or twice, that’s it.
When used gently, teeth can be a totally different sensation on the hole. Unless your guy likes having his ass pucker, do not suck in when you press your teeth against his hole — this can be painful. Graze your front teeth against his hole gently, alternating between light “taps” with the tip of your tongue, then plunge deep. The result? Ecstasy.
10. Vary your thrusts.
Once you’re finally in his butt and he is relaxing and letting you in, now more than ever is the time to remember that variety is the spice of life. Good sex does not involve the same monotonous thrust, in and out, over and over. Good sex involves variety.
Pounding is when you’re literally just slamming your dick in his ass as fast as you can, which is phenomenal and mind-blowing for a bottom who wants it. When I’m ready for rough sex, I want to get railed and am looking for a top who will pound mercilessly.
If your guy is not ready for it — if he has not relaxed his ass to that point — pounding will simply not be an option.
Jackhammering is when you pull your dick all the way out — sometimes even completely out of the ass — then slam it all the way back into the base. Note: This kind of thrust only comes after fucking for a while, once he has loosened up and is ready for rough sex.
The best sex is when you alternate between gentle, steady thrusts and quick, sudden, hard ones. The pace and rhythm of those gentle thrusts will depend on you and him and how your bodies move together.
There is no way to describe it, but once you both let go of that voice in your head telling you you’re doing a bad job — once you drop your fear of performing poorly and he drops his fear of being dirty — and allow your bodies to sync, magic happens.
When you are at that blissful point, vary things up. Give him a variety of different thrusts, from fast to slow, rough and gentle, hold it in for a few seconds and kiss him, pull it out for a few seconds and give him a break, then slide it all the way into the base, then jackhammer, then pound, then go gentle, etc. etc. Varying it not only helps you keep from climaxing too quickly, but it also gives him necessary rests between points of intensity that will help him go longer.
11. Pull out occasionally - this is important.
No matter how much you’re enjoying it, it is your duty and responsibility as a good top to pull out on occasion and check for problems. Even if he is not showing any signs of pain, there can be blood on your dick, which can mean a minor or serious problem.
This is true especially if you’re pretty big. He might be in ecstasy, but he could be cut and bleeding on the inside. There is a point inside the anus at which there are no nerve endings, meaning someone can get injured past this point and not know it.
12. Get experimental with different positions.
I have had unfortunate fucks with tops who only enjoy one position and one position only. They only do doggy-style or missionary.
Enjoying only one position will make your sex dull for both (or all) parties, and there is always the risk that the one position you like is one your bottom does not.
There are dozens of positions that are worth trying out. The best lays of my life have involved a variety of them. When you involve sex furniture and bondage furniture — slings, fuck tables, Saint Andrew's crosses, etc. — an even greater number of positions become available. Get experimental and remember there are countless ways to put your dick in his butt.
13. Use toys.
I know a few tops who do not like toys because they worry their guys will enjoy toys more than sex. This is pretty silly; nothing quite replaces a cock, but toys can deliver a lot of different sensations that a dick simply cannot, and just as you can enjoy many different kinds of food, you can also enjoy many different sensations without preferring one over the rest.
A lot of fun can be had from sticking toys — plugs, dildos, balls, and other objects — in his butt. Watch his ass stretch around it, challenge him, coach him through it, tell him he’s doing a good job, and train his ass with him. Reward him when he takes it like a champ (kiss his hole, give him a quick lick). Allow toy play to become an awesome and intensely erotic part of your sex.
Toy play can be foreplay or post-sex play. I’ve done both, and both are erotic in different ways. Toys as foreplay get his ass loosened up and relaxed and ready for your cock. Using toys as post-sex play, while admittedly less common, is something I have enjoyed a few times.
I once had a great time with a top who admitted from the beginning that he reached orgasm quickly — and did. I thought I would be disappointed, but after he came, he spent an hour or two openings my ass with toys and playing in my hole — while I moaned in bliss.
14. Take a break - inside.
This is especially important for guys who are worried about reaching orgasm too quickly. Taking a break — halting your thrusts — while you’re still inside him will give him a rest and let him get used to your dick. It will also give you a chance to prolong your orgasm and extend your play.
Pornographers would have us believe that gay sex involves the most parsed-down expressions of pleasure — “Fuck,” “Yeah,” and “Fuck yeah” — but the reality is that great sex involves a lot of talking and listening.
Communicate with him, tell him what you like, and ask him what he likes. It is OK and actually quite necessary to do so. Talk to him about his body and let him know what feels good. If he’s doing something you like, tell him so. We can only learn about each other sexually through a small variety of communication methods. Talking is our most basic communication tool, and in such an intense activity as butt sex, communication is vital.
16. If you use fingers, make sure your nails are filed down to nubs. Or use gloves.
As foreplay, many tops like to warm up a guy’s butt and stretch him out with fingers. I cannot stress this enough: file your fingernails down. Forgetting to do so is inconsiderate and kind of irresponsible since sharp fingernails can irritate and even tear the anal lining.
I’ve hooked up with guys who I even told beforehand that I like fingering, and when I got there, they hadn’t filed down their nails. Their surprise at me telling them to stop shows they have not thought things through, or perhaps they are not very experienced with gay sex in general, and my arousal diminishes.
If you want to use several fingers in his hole or finger him for a short length of time — or if you have fisting aspirations in your future — you should invest in gloves. I recommend buying nonlatex nitrile gloves since you never know if the guy you invite to your apartment has a latex allergy (ahem).
17. The pressure is not on.
If you simply hate topping, don’t top. This might mean turning down sex with sexy people, but if it isn’t something you enjoy, you cannot change that. There is no pressure in sex and never should be.
My favourite poem is “The Gas Station” by C. K. Williams. It is about one of the author’s first sexual experiences as a child. He and some friends wandered through Times Square and met a hooker who gave them all blow jobs for $10 a piece. He felt cruel afterwards, like he had mistreated someone, and as an adult, he reflected on how fortunate he was that sex came to him innocently, without cruelty or abuse, as it does for so many.
He mentions the words that, if you are lucky, should describe your first sexual encounters: complicity, wonder.
If you take nothing else away from this, remember that sex at its best is complicit and wondrous. You want to be two co-conspirators in a naughty game; you want to enter into sex acts willfully, with curiosity and as equals.
This means there is never any pressure to perform. If you are being pressured, you are with someone who you should not have sex with. If you want to bottom, bottom. If you want to top, top. If you are a bottom who suddenly wants to top, you should top, and if you’re a top who wants to bottom, bottom. If your sex partner is someone who does not encourage your best self — if he does not make you feel sexy and safe, and if he discourages you from doing what you want to do — find a different sex partner.
Even if you’re a bottom, make sure you are with guys who make you feel on top of your game.
Shout out to Alexander Cheves, The Writer