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Anal Sex 101: Gay Boys Guide to Bottoming

Anal Sex 101: Gay Boys Guide to Bottoming

Let’s be real, as gay men, most of us have tried anal sex. We’re not all experts, but I can at least speak for myself when I say I know a thing or two about gay sex.

If you’re a virgin, it’s probably on your bucket list to try anal. For some though, they’d wish for any but - no pun intended! Many guys find anal sex painful and ultimately avoid the experience. It doesn’t have to be that way! Bottoming is not scary and can make for one of the most pleasurable experiences you can have intimately between two men.

Maybe you have no idea where to start or you’re more of a top looking to explore other options, I’m here for you! 

Bottoming can take a lot of preparation, and the anticipation alone isn’t for the faint of heart. Anal sex for bottoms is like coffee. Some take to it right away, others have to warm up to it and find their flavour, and others need it. Just trust me when I say that you can find more than your happy place while bottoming. 

Here’s this gay boy’s guide to bottoming.

Anal Sex

Why even try anal?

One, nerve endings are what make things feel good and the anus has no shortage of them. Inside and outside, along the rim, all things butt can be pleasurable. It can be the most erotic region on your body and as intense as you’re after.

Anal play can be as rough or as gentle as you’re looking for. It’s an insanely sensitive region of your body, so there are lots to explore. Anal play is a common fantasy amongst gay men, so it’s likely something you’re ‘expecting’ to explore.

A lot of cultures believe anal to be completely taboo, but those same cultures also refute blowjobs. We all know, though, that when you tell people not to do something, someone is bound to do it. Over and over and over again! (Guilty!) Straight people even do it to stay ‘virginal’ because when anal sex you aren’t likely to break the hymen.

Most gays will tell you it’s their preferred way to orgasm because the pleasure can be so intense.

Ok, it’s time to talk poop

Shit happens, that’s literally the name of the game with anal sex. It’s not really about actually pooping during intercourse, but there are likely some bits in your anal canal. If it’s not visible, there still fecal matter on the cock, toy, or finger in question. For the best anal experience for the least amount of work, I recommend pooping and showering about an hour before you get down and dirty.

You can take things a step further with enemas and douches. These allow you to get a deeper and more thorough clean, so if you’re expecting to get bred to filth, this is likely the route you’d want to go to prepare. But, for the love of everything Cher, please clean whatever goes into an anus.

And pee after sex so you don’t get a UTI. Yes, men can get UTIs too.

As far as safety first, anal sex is a lot more likely to transmit sexual diseases. This is because the membrane of your anal walls is very thin. It’s a double-edged sword because that’s also what makes it super pleasurable.

Gay Boys Guide to Bottoming

The four rules to anal sex: go slow, breathe, relax, and use lots of lube

It really is about mind over matter here. I mean it’s an outtie where you’re making an innie, not the easiest endeavor. So, starting from the top: is this something you actually want or are you following someone else’s desires? If this isn’t the scene, time, or partner for you, that’s totally ok. Just no that if you decide to proceed anyway, your hole is going to be so clamped up and tight, you are not going to love the experience. Your top might get a thrill from such a tight hole, but it’s just going to be awkward all around.

Before you try it out with a real-life dude in the flesh, buy yourself some toys and get to know your booty, bootyhole, and prostate. If you explore what areas, angles, and depths feel best on your own, you’ll have the experience to help guide yourself through a fantastic fuck. You can start as simple as a finger massage and work your way into dildos if that’s what you’re after.

Just go slow, for fuck’s sake. Don’t scar yourself from an incredible pleasure simply because you mucked up as a beginner. Not every homo is going to have anal sex, and there’s no pressure to, but if you think you’ll like it, set yourself up for success with some personal experience.

Pro anal sex tip 1 from a power-vers (aka, I like em both ways, hard, hot, and heavy): As a beginner bottom, take control of at least the first position. Start out having cowboy style sex, where you ride him while facing each other. Honestly, it’s a very intimate position, but you have control over how and when that cock goes inside you. It also lets you warm up to your hole being stuffed full of man-meat. Overall, it’s a great way to get the party started then your top can start going to work laying pipe in your booty. Another position that works well is a big-spoon little-spoon scenario, where the bottom is the little spoon. The reason it works so well is because your anal muscles relax in the position, especially if you bring your knees closer to your chest. It’s great for first timers and gives the top a bit more to work with when you’re ready to reposition. 

Tip # 2: While the anus does produce some mucus, there’s nowhere near the self-lubrication you need for comfortable anal sex. Use lots of lube and reapply if things feel ‘dry’ even if he swears your hole is oozing lube.

Sliquid Naturals Spark Booty Buzz

Sliquid Naturals Spark Booty Buzz

Most guys prefer silicone lube because it’s the easiest to use since there isn’t a big need for reapplication. Water-based lubes tend to dry out quickly, but they benefit from being easy to clean up. I really prefer to find a water-based lubricant and if I’m in a pinch I go the au natural spit route, but my partner takes cock like it’s his life-force. In time, you can find your way to spit fuck (try swapping spit so one of you can ‘take’ it to the receiver’s hole), but it’s not recommended for your first attempts at anal sex.

Gun Oil - H2O

Gun Oil - H2O

A kitchen remedy in a pinch is coconut oil, because not only will it slick you up nicely, it’s edible too! Lube is really personal, so try some out with you’re budding toy collection or just while masturbating until you find the one for you.


Try rimming

Rimming is when you’re performing anilingus or the kissing, licking, or otherwise pleasuring of the anus via the tongue. You can get a little bit of penetrating going and loosen things up as you relax into anal foreplay. Big Brother recommends using plastic wrap, a dental dam, or even a split condom to orally pleasure an anus because of orally transmitted sexual infections. 

Bring out the toys

I mentioned toys for personal play, but they can be even more amazing with a partner! You have less control over what they do with the toys and how they use them, so that’s hot, plus you might learn a thing or two. Start small with a prostate massager so that you don’t feel as much of the stretching sensation, but you get to enjoy the penetration and feeling of depth.

VeDO Quaker Anal Vibe

VeDO Quaker Anal Vibe

As a bonus, most of them vibrate which simply adds to the layers of pleasure you’re in for.

You could try wearing a small butt plug before sex or even out on a date to warm up your hole. This way you’re already past the initial penetration stage and ready for dick. You can find loads of flexible, small butt plugs in a variety of shapes, so it’s a matter of finding one that works for your budget and goals for anal play.

Stay away from extremely rigid toys like metal or glass ones that are nothing short of inflexible. A beginner bottom should use toys that are smooth and flexible, as an absolute requirement, any anal toy should have a base or set of balls that prevent it from easily slipping in and disappearing.

Tantus Silk Silicone Dildo

Tantus Silk Silicone Dildo

The right dildo for a beginner is not hard to find! Just keep these qualities in mind when you’re browsing.

Never forcefully insert anything into your bum. Sure, there’s the popping sensation on occasion, but it shouldn’t be all that hard to get a P in your A. With the right angle, and lots of lube, his cock or a toy should slide in with a little guidance. This is where practice makes perfect.

You can experiment with different angles and even repeatedly penetrate your anus to loosen up the muscles before full penetration.

You can use a condom on your toys too, and not just for avoiding transmitting diseases if you share with your partner. You can also take advantage of the slick surface. Condoms are designed to work seamlessly with lube, so it makes a great combo when you’re bottoming as a beginner.

This is especially true if you are looking at a longer-term toy rather than just a beginner toy. That way you can buy something that you’d like for regular use, but it’s slick and easy to insert!

Vibrating toys can be a huge hit too! You can use them to apply vibrations to your perineum (the area between your balls and anus, which is also super sensitive) and stimulate your prostate from the outside. Of course, they can also be used analy, but I love teasing outside the hole with all my options before deciding which is the lucky one to penetrate first.

The final tip for toys: Go with silicone, you won’t be disappointed. Clean-up? A breeze. Flexibility? On point. Durability? For daysss!

Seriously, silicone toys are honestly my favourite for anal play because they just fit the bill perfectly. None of my other toys are as easy to clean as my silicone ones.

Anal Sex 101 Gay Boys

More intense play

If you’re looking to experiment any further, I’d recommend a classic BDSM practice. Use a safe word. My hubby and I were fortunate to get advice from the resident dom of a local sex club and he recommends using the traffic light system.

Using a word or phrase like Peter’s Petunia’s might be awkward enough to ruin the mood, where the traffic light system is more of a guide. If you say green, that means the coast is clear, there’s no pain, feel free to keep doing what you’re doing. Yellow means to ease up, where Red is the full stop. It’s simple, concise, and a bit more informative than a word or phrase that stops everything

Once that’s established, your play can be taken to whatever extreme you like. From bicep-deep fisting to tied up and tortured for hours. The possibilities and pleasure are endless!

Happy bottoming!

Guide to Bottoming

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