Pegging Demystified: A Bottom’s Guide to Enjoyment and Comfort

Guest post by Hercules Liotard

The Pleasure Coach (He, Him, They, Them) (@hlpleasurecoach) / X

What’s pegging?

Put simply, pegging is anal sex from a partner wearing a strap-on. But, usually, it describes when a guy receives anal from a female partner wearing a strap-on. As a guy who loves a good pegging, I figured I'd help aspiring pegging bottoms be the best bottoms they can be.

Although, I don’t like the word “pegging” because it’s just a word made to make hetero-males feel more comfortable taking a fake dick up the ass. Liking anal sex as a hetero male does not make you gay or bi or anything else. Receiving anal sex is an enjoyable experience, don’t let those fuckers ruin your evening.

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How to warm up to pegging

Before you start sticking anything anywhere, you need to establish yourself with anal. If you’ve never touched your anus or inserted so much as a finger up there, you need to get acquainted with your new friend.

Assuming you’ve read or watched the basic anal sex hygiene guide and the advanced anal sex cleaning guide, you can start at picking a lubricant. There are a variety of lubes. From oil-based (like The Butters) to water based to silicone and even silicone/water hybrid lube. There are pros and cons to each and preferences for viscosity or slickness.

We recommend oil-based lubes for anal play typically. Some condom materials won’t be compatible with oil based lube but that’s less of a concern if it’s not being sued on a penis.  

After choosing your trusty lube (preferably The Butters Lube), you can start exploring your anus. Using a finger, work from the outside by stimulating the anal sphincter and ultimately going inside you, when your booty is ready. Remember, anal sex is easy: open your mind and spend some time opening your anus, you’ll open yourself up to new possibilities.

You’ve gotten accustomed to using your fingers or you’ve moved onto using toys because you’re really enjoying yourself. Now, whether it was your idea or your partner(s), you want to get your boy booty banged out.

The actual act

You may be nervous and tempted to clam up but communication is key! Before you start taking anything, talk with your partner. No matter how much you’ve played with yourself, having someone else take the lead is a completely different experience.

Make clear guidelines. Tell them what you want and, more importantly, don’t want. Remember, you are giving them consent and you can take it away. Once you feel comfortable that you got the point across, you can throw those legs in the air.

Before I get on my back and start taking the pounding I’ve been waiting for, I have my partner(s) start kissing me. Kissing relaxes the body and puts you at ease. If you get nervous, the intimacy and pressure-free comfort of kissing may help you too. Find a position that feels the most comfortable to you, whether its on your back, doggy style, on your side, or something from the Kama Sutra.

Supporting your new pegging top

Now, if your partner(s) is/are not accustomed to hip thrusting with a cock/phallic object you may need to guide them inside with your hand. Lack of response from the toy increases the learning curve for strap-on sex/pegging. Once inside, you have to give them the go ahead to start moving. If they’re also new, they may be hesitant or awkward in their movement, give them time to get a rhythm going.

If things become uncomfortable, ask to slow down, stop, or add more lube, you can never have enough lube. But, most of all, don’t forget to have fun with your newfound love of anal sex.