How to have anal sex: Steps for gay men

If having anal sex was as easy as it appears in gay porn, I’d probably do it every day. However, there is more to it and gay men (women too) need to understand how to have anal sex.

It wasn’t until my mid-20s that I got truly comfortable with anal. When I was younger (I’m still in my very very late 20s, or very early 30s before you ask), I had some really painful experiences as a bottom, and some scarily messy experiences as a top.

During gay sex, whether you’re top, bottom, versatile or have no idea (we’ll cover this another time), planning, practice, preparation and communication are all vital when taking it up the rear. I wish I knew what I know now, when I was younger. But now I know plenty. We’ve got this sorted. Here’s how to have anal sex.

Before anal sex, get to know your ass

It’s your body, it’s your butt, it’s your prostate – that’s the gland full of nerve endings that makes anal sex feel good.

Start small. Finger yourself in the shower, find out what feels good for you and get used to the sensation of having something in your ass. If you’re nervous about getting f**ked, buy a dildo – then you’re in control. Simples.

Don’t be a douche, douche

This is stating the obvious, but anal sex can be messy. Although some guys don’t mind this, it can be a complete boner-killer and passion-destroyer.

When I was in my teens, I had a few messy experiences that knocked my confidence. Once was on a beach in the dark with nothing to wipe ourselves with other than sand – OK, too much info.

But then I discovered douching. Basically, giving yourself an enema, with water from the shower hose (being very careful the water temperature and water pressure is constant), or from a ‘bulb douche’ which you fill with water then squirt up your arse.

If you’re planning on a long anal session, you could take an Immodium which should further minimise risk.

Even with all this planning, there’s always the risk of a bit of mess. Shit happens. Literally. Try getting darker sheets, and always keep baby wipes to hand to wipe off any unwanted mess.

At the end of the day, it doesn’t really f**king matter – we’re all animals, so just laugh it off. After it’s happened a few times you’ll see that it really isn’t such a big deal.

Talk about anal sex

Anal sex is a team sport, of at least two. So talk to your partners about what you’re expecting or hoping for. At the very least that should probably be whether you prefer to be top or bottom, and what your opinion is when it comes to safe-sex.

If you wait until you’re in bed together, naked and thrusting, one of you is more than likely to get a surprise. Two tops don’t make a right. Sure, lots of guys are versatile, but if you’ve already had ‘the chat’ you’ll know what to expect when it comes down to it. It’s a bit of a cringe-worthy line, but ‘what are you into?’ usually works.

Listen to each other

Keep communicating. If you’re topping, don’t just ram it in. Give your partner time to relax. If he says stop, stop. If he says keep going, go for it.

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If you’re bottoming – breathe. Take deep breaths. Relax. If you’re too anxious your anal sphincter muscle will tighten, and that means pain.

When the tip of his cock is inside you, push out your sphincter. Expand and contract your sphincter muscle, and each time you do this, let him enter you a bit more.

Lube up

Use lots of lube. Put lube on your cock if you’re f**king, and inside your partner’s ass.

The spit and shove you might see in porn only really works in porn (or for anal veterans who’ve been taking it for years). Use water-based lube as anything oily can cause a condom to break.

Anal sex Positions

Experiment with different positions to find which one is most comfortable for you.

If you’re new to getting f**ked, you might want to try riding your partner, so you’re in control of how much cock you’re taking at any one time.

Does anal sex hurt?

Yes. It does. To start with anyway. The first time usually hurts like hell. That’s kind of just how it is.

But with practice, it gets better, and then it’s f**king awesome. Like any set of muscles, the ones in your ass need training.

Safer sex with condoms

Keep a few condoms in your wallet, or in the drawer next to your bed. Keeping them on the bedside table sends a clear message that you’re into safer sex.

Or, it might make you look like you’re f**king every man that catches your eye (you lucky bugger), which might put off a potential boyfriend compared to a casual hook-up, so use your judgement.

PEP and PrEP

Unlike Kimmy Schmidt, condoms are not unbreakable (if you don’t get that reference babes, get on Netflix). If a condom does break, or if you happen not to like condoms, which is up to you and your partner at the end of the day – there’s PEP and PrEP. Here comes the science bit, concentrate…

So, what’s the difference between PEP and PrEP?

PEP (POST-exposure prophylaxis): If the condom has broken or if you’ve been barebacking, you should probably consider PEP. Basically, you take a course of pills for a month that have proven highly effective in stopping HIV transmission.

If you think you need PEP, go to your local A&E or walk-in sexual health clinic – within 72 hours of the ‘incident’ happening. Any longer, and it won’t work.

PrEP (PRE-exposure prophylaxis): The pill Truvada (one of the pills in PEP, actually), is a highly effective treatment in the prevention of getting HIV.

For those of you in the UK, it’s not yet available on the NHS, apart from in Scotland. But it will be really soon in England and Wales (sorry Northern Ireland). In the US, you’ll have to check with your insurer.