How to Bottom For the First Time

In a sexual context, bottoming is the act of taking a dick (or a dick-shaped object) in your ass. When it comes to gay and bi men, a lot of people seem kind of obsessed with working out who's a top/giver and who's a bottom/receiver, but in reality many MSM (men who have sex with men) do both and some do neither. In 2021, it's painfully heteronormative to presume that sexual intercourse has to involve a hole being filled by something cock-shaped.

On one level, bottoming is really no big deal – if you like riding dick, go ahead and ride it. But on another, butt-fucking is still cloaked in myth and stigma. “There's an association that those who bottom are feminine and those who top are masculine,” says Ian Howley, CEO of the health and wellbeing charity LGBT HERO. “And we all know where that stigma comes from: Hello, toxic masculinity.” 

Happily, Howley says this reductive presumption is finally dying out as we all become more open-minded. “You now see lots of 'masculine' men who enjoy bottoming, including straight men who finally found out just how much pleasure they can get from their arse,” he says. Some even like to define themselves as a “power bottom” – a bottom who calls the shots. 

When you get into the swing of it, bottoming can feel both subtly subversive – take that, patriarchy! – and a lot of fun. With this in mind, here's a guide to bottoming confidently like there's no tomorrow.

It's incredibly important to get to know your own body before trusting someone else to enter it. Sex toys and loads of lube are very much your friends here – but don't rush it. 

“There's no need to take an entire dildo to begin with,” advises Zachary Zane, a queer sex columnist and sex expert for Promescent. “Start small, with one finger. Then when you feel loosened up, add another. If it hurts, stop what you're doing, breathe, apply more lube and try again.”

Zane also points out that it’s helpful to be pretty turned-on before you begin fingering yourself. “You can't just shove something up there when you're not into it,” he says. “When you're aroused, your body relaxes, and you can start taking whatever it is that you're putting inside of you.”

There’s no need to get squeamish about douching; it's just rinsing out your anus with water to clean it. At the same time, medical professionals have said that douching before anal sex is definitely not necessary and should be done carefully and sparingly. Excessive use of enemas, for example, can lengthen your colon and lead to constipation in later life (fun!).

It all comes down to making a personal and informed choice. “Some bottoms never douche because they don't have to, but that's not me and it's not most folks,” says Zane. “Then there are some bottoms who douche every time because they want to know, definitively, that they're clean and ready to go. It empowers them.”

Bradley, a 38-year-old gay man from Durham who asked us to withhold his surname when discussing “intimate details” of his sex life, has been bottoming his “entire sexual life”. He also likes to douche. “I don’t know if it's become a mental association, but when I douche it's like my body knows what's coming next,” he says.

“Also, I like my hole to get a lot of attention, including rimming. And if I want to be rimmed, I feel like I 100 percent have to douche.”

Still, Zane points out that if you always douched before bottoming, you'd never have spontaneous anal.  “There are times I've really wanted to bottom but didn't douche [beforehand], so I just let them know I might not be the cleanest down there,” he says. Which brings us onto…

Your body is a brilliant thing and there's no shame in the fact it produces waste matter. Entire articles have been written about the “bottoming diet” – this one is especially helpful – but the basics are straightforward. “In general you don't want to eat foods that give you the runs, so fatty, spicy and greasy foods are typically a no-go,” says Zane.

“And you'll probably want to consume a lot of fibre [because it] helps everything run smoothly. Make sure to drink lots of water too, because if you eat a lot of fibre without drinking water, you'll bloat.”

It's a myth that bottoming is impossible with IBS, but it might require some extra prep. “Just listen to your body and let your partners know that sometimes they may experience some sounds and smells,” Howley recommends. “Sex is messy and anyone who thinks it isn’t is fooling themselves.” And even if you do spot a bit of shit on the condom afterwards, don't be spooked. Nine out of ten tops will have seen it all before.

“If it's your first time, choose someone who isn't hung like a horse,” recommends Louis Staples, a 28-year-old seasoned bottom from London. Even if it isn't your first time, keep in mind that bigger doesn't necessarily mean better. “It doesn't take a huge dick to pleasure you because the most sensitive part of the arse is the first three or four inches,” Howley adds. “After this point you'll hit the prostate or male g-spot, but beyond that point there really isn't much sensitivity.”

It’s also worth going for someone you trust and who’ll be gentle with you. Your ultimate fantasy might involve getting pounded by someone anon after saying “I'm just a hole, sir”, but you'll probably have to build up to being fully submissive. “Often on the apps, bottoms are like 'yeah, ruin me!' and some tops don't take this with a pinch of salt,” Staples says. “So be honest about the fact you might need them to go gentle at first.”

Zane says "there's no such thing as too much lube" because your anus doesn't lubricate itself. But if you're using a condom, avoid oil-based lubes because they can make the latex break down. Equally, if you're using sex toys, bear in mind that silicone-based lubes can cause silicone toys to warp. 

It might take time to find your favourite lube, but Bradley from Durham recommends Liquid Silk. “Don't buy the Durex stuff you see in supermarkets [because] it’s shit and overpriced,” he says. For Staples, lube is completely non-negotiable. “Loads of tops have this fantasy of using spit instead, but I'm sorry, it's just not happening,” he says.

It's unfair, but some bottoms experience more discomfort than others. Staples says “a dick going in there is always a bit painful for me”, while Bradley only feels a twinge “if the top isn't in the right position”. Still, be aware that your first time might hurt. “You might feel a really sharp pain at first but it will go away after a few seconds. If this happens, you need to stop, take your time and try again,” says Howley. 

“When the dick is inserted it’s best to contract your anal passage or push outwards – don't clench. This helps to open your passage and should lessen any pain and make it more enjoyable.”

Sniffing poppers can help to relax your sphincter, but the lightheaded sensation they give isn't for everyone. And if you take a load in your ass, remember that what goes up must come down – but maybe not until the next day.

“It’s likely your first time will be awkward and you may feel weird afterwards,” Howley adds. “But after a while you’ll learn what your body can and can’t do and you’ll form a personal strategy that will allow you to enjoy bottoming.” 

@mrnicklevine