Pegging for First-Timers: A Couple's Night In

So you've said it out loud. Maybe you were a bit drunk, maybe you were in bed, or maybe it just slipped out during a conversation about something else. One of you would like to wear a strap-on, and the other would like to find out what the fuss is about. Congratulations. You're about to have one of the most intimate, funny and absolutely filthy nights of your relationship.

Pegging usually means a woman using a strap-on to penetrate a man's arse. It's more common than you'd think, and it has nothing to do with who he's attracted to. Straight blokes have a prostate, too.

Why do people love it?

For him: The prostate. A firm, deep pressure in the right spot can feel unlike anything else, and there's a certain thrill in giving up control for once.

For her: A lot of women get a massive kick out of being the one in charge, with all that power, and having their man at their mercy. A base pressing against your clit doesn't hurt, either. Many say it's the first time they've really understood how it feels to fuck someone.

Bringing it up

Do it with your clothes on. It's a much easier conversation than you think. "I've been thinking about something, and you can say no" is a good opening. Lots of men have been wanting to ask for years, so don't assume. Our yes, no, maybe list is a good way to get it on the table. If he's hesitant, take it slow. Try a finger first during a blowjob, and see how he feels about it. And nobody should be pressured into anything. If he says no, it's no.

What to buy

You'll want three things, and you shouldn't go big.

• A harness that fits. The Sportsheets Deep Dive is an affordable start. It's got 4-way adjustable straps that fit up to 60 inch hips, and an O-ring that takes most flared-base dildos. Our harness guide goes through the options, and here's what to do if yours slips.
• A small, slim dildo. Smaller than you think. Your eyes will always be bigger than his arse. The Fun Factory Limba Flex S is a slim 12.2 cm with a smooth tip and flat base, and you can bend it to the right angle.
• Lots of lube. Wicked Simply Natural is water-based, so it's safe with silicone toys. More than you've ever used. Then use a bit more. Our anal lube guide has more.

Getting ready

He'll want to shower and go to the toilet beforehand. Eat lightly that day. Most people won't need more than that, but here's our guide on douching if he wants to. Accept that a little mess is possible, and put down a dark towel. It's nothing to be embarrassed about.

Practise putting the harness on and walking around before the night, because you'll feel ridiculous at first, and you may as well get that out of the way when you can laugh about it. Laughing's very much allowed.

The main event

1. Warm him up properly. Lots of foreplay. He needs to be very turned on, and relaxed. A bit of ball play or rimming helps.
2. Start with fingers. Trim your nails, lube up and use one finger, then two. Curl it towards his belly button to find the prostate.
3. Move slowly. Add lube to the toy, and press gently against him, without pushing. Let him breathe out and push back onto you. It's his body, so he sets the pace at first. Wait a while before you start moving.
4. Keep checking in. A strap-on doesn't have nerve endings, so you can't feel how hard you're going. Watch his face, and listen to him. Go much slower than you think you need to.

The best positions to start with

Have him on top, so that he's in charge of the depth. Or try him on his back with a pillow under his hips, so you can see his face and get to his cock. Our strap-on positions guide has the details. Don't start with hard doggy. Everyone wants to, and you should wait.

After you're done

Clean your toy, have a cuddle and talk about it. This can feel like a big deal, and he might feel a bit vulnerable, so make sure you check in. Tell him how hot it was. Then do it again sometime. Our guide to cleaning anal toys tells you what to do with the gear, and this hygiene guide explains why you shouldn't swap that dildo to anywhere else without cleaning it first.

If it hurts, stop, and try again another day. Otherwise, enjoy your new life as a person who owns a harness. You may never look at him the same way again.