First time anal sex: all you need to know

While growing in popularity, within relationships anal sex can still be a divisive and delicate subject to broach.

Generally speaking, most men are keen to give it a go while most women are more cautious. Interestingly, gay men also approach their first time with trepidation and the same guy who assured you it wouldn’t hurt one bit suddenly loses enthusiasm if you suggest pegging (putting on a strap-on dildo and penetrating him)!

So the first thing to remember for both of you is this: it’s the person being penetrated who is the boss here.

Whatever they say goes. If they want to work up to anal intercourse, taking baby steps, and taking six months to get there, then that’s what you’ll do.

If they decide they don’t EVER want to go there, that’s what you’ll do.

When it comes to anal sex, there are some crucial rules you need to follow to ensure your partner is shooting through the roof with pleasure not pain.

The good news is if you follow these steps, you’ll hopefully be well on your way to adding a new dimension to your sex life.

This three-step guide is for couples attempting anal intercourse for the first time.

Step one: anal play

The first thing to do is get your bottom used to being penetrated and the best way to do this is through anal play.

This blog has a step-by-step guide to using anal play to prepare for anal intercourse.

Read it before proceeding to step two.

Step two: know the rules

Be safe. Use lots of good-quality anal lube, use strong, good-quality condoms or both get tested for STIs and get the all clear.

Don’t double dip. Don’t EVER go straight from anal intercourse to vaginal intercourse without washing thoroughly first. It transfers all sorts of things into the wrong places.

Prepare properly. Just in case you skipped the first bit, never attempt penetration without first inserting fingers or anal toys. The rectum needs time to get used to things inside it!

Think before you eat! You both want to be relaxed. Tucking into gas-inducing foods like onions, chickpeas, broccoli or cauliflower is not going to add to the experience.

Go to the loo. And have some baby wipes nearby, just in case. Put an old towel down to protect anything you don’t want stained (some lubes stain and you won’t be skimpy with it!). The rectum delivers but doesn’t store waste so if you’ve emptied your bowel, you should be fine but it won’t hurt to have some baby wet wipes by the bed to discreetly wipe fingers, toys or penises afterwards.

Consider using an anal douche. Used properly, douching can provide further peace of mind and make you feel more confident and clean. They also help to relax the anus. If you use a reputable brand and follow instructions, douching is a safe and effective means of anal cleansing, though don’t get into the habit of over douching (all that does is irritate!).

Talk constantly. Especially if it’s your first time. Whoever is on the receiving end needs to constantly give feedback about how it’s feeling. They’re the boss, remember! Tattoo this on your forehead.

Step three: Doing the deed

Let’s first answer the all-important question: ‘Will it hurt?’

I think the most honest answer to this is that the first time can feel a little uncomfortable with the odd ‘oww!’ moment. But it shouldn’t be painful. If it is, you’ve rushed into it or you’re a bad fit (too small a bottom with too big a penis!)

This is why you MUST use a good-quality anal lubricant and relax the muscles inside the anus by massaging with your fingers first.

While anal intercourse can feel uncomfortable initially, once you relax into it any pain should subside and the pleasure factor start to kick in.

If you’re giving:

  1. Apply lots of lube to both your penis and their bottom then rub the penis head against the opening.
  2. Wait for the anus to relax and open and let them back onto your penis rather than you doing the penetrating.
  3. Hold your penis at the base and wait until the head (only) penetrates. Pause until they say it’s OK to go further and insert a little at a time, waiting each time to allow their muscles to relax around you.
  4. Once it’s all in, pause again, then start by simply moving your hips in a small circle and rocking gently against them. Only when they’re ready, do you pull back slightly and thrust in the usual manner but keeping it gentle, slow and shallow.
  5. Increase the speed and length of your stroke according to what feels good their end. Hard, deep thrusting is fine if you’re both up for it but only when they’re absolutely certain (and don’t be surprised if it takes a few goes to get to that point).
  6. Stop regularly to apply more lube and exit as slowly as you entered – go too fast and the muscles will tense and spasm.
  7. Stop moving immediately your partner says ‘stop’. Like, that second. I don’t care (and they don’t care) if you’re just about to orgasm. If they’re in pain, they’re in pain. So stay still and either wait until they’re ready for you to resume or gently withdraw completely.

If you’re receiving:

  1. The more aroused you are, the less it will hurt (having an orgasm first helps to relax you).
  2. Hold your bottom open and bear down a little (as though you’re trying to go to the toilet). This opens your anus.
  3. Breathe deeply then back up to allow them to penetrate a little. If you start to panic, try contracting your anal muscles voluntarily to give you a sense of control.
  4. Give constant feedback on how you’re feeling. It can take a few sessions before you can accept their penis fully (and if they’re large, sometimes never) so don’t feel rushed or pressured.

Didn’t go to plan?

If it was hard to penetrate and really uncomfortable there are several reasons why.

An obvious reason is you’re not using lube, enough lube or a thick-enough lube. Anal play without lube is not just unpleasant, it’s bloody awful! So squeeze that lube and keep adding it along the way.

The second reason it may have hurt is because you tried to hurry things up. You’ve rushed in (literally) and your or their bottom has clenched into one almighty ‘Who the hell goes there!’ protective brick wall.

It’s not just the two sphincter muscles that make entry difficult. The rectum is S-shaped, which is why penetrating it with a finger, toy or penis too quickly or roughly hurts like hell. It needs coaxing and gentle manipulation to move along it.

Also remember it feels most uncomfortable at the entrance. Once the finger/toy/penis gently goes in deeper, it all starts to feel more comfortable.

It could also be the position. Try one where the receiver’s legs and upper body are at a right angle – that will make the canal straighter. Don’t be scared to move around and adjust positions and angles until you figure out what feels best.

Remember also to pull out just as gently as you went in. It’s just as important to exit slowly as it is to enter.

Please, DON’T use desensitising gels during anal sex (or do loads of cocaine or poppers), especially the very first time. Pain is a warning you’re being too rough.

Incidentally, if anal play or intercourse is painful for you and you seem to be doing everything right, give it a miss. Well done for giving it a go but if there’s pain or bleeding, it’s not for you.

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