What’s the best order to follow if I want to explore anal play and anal intercourse?

Photograph by Dainis Graveris on SexualAlpha

There’s a very good reason why anal play and anal intercourse are now so popular. (Around 36 percent of women and 44 percent of men aged 25-44 have tried anal intercourse.)

It’s a hot spot for everyone and packed with nerve endings.

But where do you start, if you’re keen to experiment?

Here’s my take on the most logical, comfortable order of activities, if you want to explore anal play.


Start slow (as in the time between trying a finger and trying a penis is weeks, rather than the same session).

Be gentle.

Stop if it feels too painful.

And choose your time. Many a lover’s hand has been brushed aside while tentatively exploring, never to return again, not because their partner’s weren’t interested but because they were worried they’d break wind.

After a big dinner out isn’t the best idea you’ve had.


Spank their bottom

Bend them over your knee or do it during intercourse when you’ve got good access.

Wait until they’re fully aroused (the more turned on we are, the more receptive we are to erotic ‘pain’), then start by running your hand lightly over those fleshy orbs, simply enjoying the feel of them.

Then cup your hand slightly, keep fingers together and administer a light spank in a slightly upward motion.

Your first spank will sound more dramatic than it feels but if they aren’t expecting it, they’ll be shocked. Immediately massage the area for a few seconds, laugh or fix them with a wicked look (depending on which you think will convince them to let you continue), then try another spank, timing them to arrive no later than 3-5 seconds apart. Cover both cheeks, aiming for the lower (fleshier) part of the cheeks. If they seem to like it, you can then start to increase the force a little.

Insert a finger

It’s safe and not too ‘out there’ but naughty enough to get the heart pumping, doesn’t hurt and feels amazing because there are highly sensitive nerve endings inside the rectum of everyone.

Simply apply some lube to your finger or your partner’s bottom and start by rubbing your fingertip gently around the rim of the anus until the muscles relax.

Use the finger you point with to begin with, inserting it a tiny way, the waiting for the rectum to get used to this new, if welcome, intruder.

Keep inserting a little at a time and once it’s all in there, either make a ‘come-here’ stroking motion or make little circles.

Do NOT use a fierce, in-out thrusting motion, like some do inside the vagina unless you’re asked to – and especially not the first time.

Try a butt plug

They’re usually made of rubber, silicone or jelly and shaped like little penises who’ve eaten too much – they expand in the middle – with a flared end (to stop it disappearing up you-know-where).

Even if you’re not in the slightest bit interested in ever taking anal stimulation further than just a finger or a small toy like this one, the butt plug is a non-threatening way to explore and experience the highly arousing sensations produced by anal stimulation.

Use the same steps as for a finger to insert it, then simply leave it there during oral sex or intercourse to add an erotic edge.

They make you feel pleasantly ‘filled up’, provide pleasant pressure on everything else (the rectum shares a wall with the vagina) – and they get your bottom used to relaxing around an inserted object (just in case you change your mind about the other).

You can buy vibrating butt plugs or insert a slim vibrator a little way to see if you like the sensation (without letting go, unless it has a flared end.)

Try some anal beads or a prostate massager

There are lots of varieties. Most look like this.

Add lots of water-based anal lubricant, then slowly insert the beads into the anus, pausing to get used to the feeling. They may feel uncomfortable initially but should never feel painful.

Leave in place, and continue having sex (intercourse, oral sex or using fingers or a vibe on other areas).

The most intense feeling is experienced when you pull the beads out and they pass along the two ringed sphincter muscles, triggering intensely pleasurable sensations.

Pull them out as you approach orgasm or at any time during foreplay.

Prostate massage is another highly enjoyable way to explore anal play. Add vibration if you want to take it to another level. Here’s my vibrating prostate massager.

If you want to try a toy that doubles as anal beads and a prostate massager, try this one. 


A word before you do though. Actually two: safe sex.

Anal play and anal sex comes with a hefty ‘approach with care’ warning: the chances of infection are higher than with penis/vagina sex.

Get tested, use dental dams or condoms and don’t insert anything that’s been into the anus into the vagina without washing thoroughly.

Now, and only now, proceed…

Try rimming, licking the ‘rim’ of the anus and/or inserting a stiff tongue inside it. As you can imagine, some people find the thought outrageously sexy while others would rather cut their fingers off with a saw, one by one.

Cover the opening with a piece of cling film if you’re squeamish or want to be safe.

Attempt anal intercourse – you can always stop if you hate it! Now, if you’ve skipped all the other stuff and come straight to this bit, pay attention: you should never go straight into anal intercourse without having tried other stuff first (fingers, dildos, butt plugs etc).

If you have, here’s what to do. (I’ve written it from the perspective of the person penetrating, by the way and this is a crash course. You’ll find a longer guide here.)

Apply lots of lube to both your penis or strap-on and their anus, then rub the penis/strap-on head against the opening. Wait for the anus to relax and open and let them back onto your penis, rather than you do the penetrating. Hold your penis/strap-on 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, very slowly. Once it’s all in, pause again, then do slow, gentle, shallow thrusts. Stop regularly to apply more lubrication and exit as slowly as you entered – go too fast, and the muscles will tense and spasm.