So you and your partner have decided to jump into the world of pegging. It can be daunting at first, but with a little bit of preparation and conversation, pegging your man can be a hot and intimate experience for both of you.

Work Your Way Up

First, you’ll need to find the right toy. It’s recommended to start small and work your way up to a larger toy, but of course this also comes down to preference. There are plenty of beginner strap-ons. This one by Sportsheets is a great starting point: It’s an affordable set that comes with a dildo and super cozy harness. It’s very sturdy, so it gives the wearer more control. This will make the whole experience more comfortable and less awkward. No fumbling around mid-sex! (Although that will probably still happen, and that’s okay!)

Talk First

Talk beforehand about what position he might want to try out. He might want to be on his back for the first time since it does allow for eye contact as well as the ability to relax completely into the bed as you peg him. Another benefit to having him lie on his back is that it gives you the chance to watch his reactions as you slide that dildo inside him. All fours is also an option of course, but it really is whatever he prefers.

Lube Is Your Friend

Lube is your friend! Any time anal play is involved, lube is a necessity. Water-based lube will be safe for any of your fun toys but doesn’t last as long as a silicone-based product, so reapplication may be required. This is totally normal, so go to town. Lube it up!

Active Communication

Communication will be key. Go slowly as you peg him, with consistent check-ins. Asking if it feels okay as you take your time will not only reduce any discomfort but will create a trust that’s necessary for intimate moments like these. A simple “is that good?” or “how does that feel?” while you’re entering him will do the trick. But be prepared for feedback, requests, etc. This is all part of the experience.


Even after the act, have a conversation with each other. It’s nice to cuddle up and hear what the other person thought about the experience. Trying new things can feel overwhelmingly intimate or awkward, so a little reassurance can go a long way. Sex is fun and all about exploration! If your man didn’t like being pegged like he thought he would, no big deal. Not everyone will be a fan. But if he did, just know there’s a whole world of different toys available, and lots of room to explore. Have fun!