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A Guide to Pegging

June 8, 2026

Anything Goes Phone Sex, Phone Sex, Strap-on and Pegging

A Guide to Pegging

Over the last few weeks, I’ve been enjoying a lot more anal play with my partners. Specifically, I’ve been enjoying pegging. At first, the idea of pegging one of my boy toys was scary.

However, a little time and patience has made pegging so much fun. This is a guide to pegging for people that curious about what it takes to give a guy a good pegging.

What is Pegging

Pegging is described as the act a woman of using a strap-on dildo, vibrator or manual dildo to anally penetrate a man. The purpose of pegging is to help a man achieve a prostate orgasm.

But pegging isn’t just about helping men have a prostate orgasm. Women can cum during pegging too. A lot of strap-on’s have a wide base that is designed to press against a woman’s clit, for an outstanding orgasm.

What to Use During Pegging

Before you get near his assholes you are going to needs some supplies. Here is what you’re going to need for a basic pegging session.

Strap-on or a dildo– This is a must have for a good pegging session. Whether you use a standard, manual dildo or go all out for a strap-on, just make sure that it something that you and your partner agree on.

Lube– And a t lot more lube that you think you need. Unlike a woman’s pussy, a man’s asshole isn’t self lubricating. So make sure that you have plenty of lube for your pegging adventure. I prefer water based lube. It get really slick, and doesn’t stain your clothes or sheets like silicon lubes can. Water based lubes are compatible with most silicon dildos and strap-ons.

If you are feeling super adventurous, here are some other accessories that can make for a wild night.

Vibrating cock ring or vibrator– Using a vibrator along with your strap-on can make the pegging orgasm more intense for the guy.

Wearable vaginal vibrator– This can help the woman doing the pegging cum. Especially fun if you’re also using a strap-on that has a base that can tease your clit.

A Guide to Pegging: Step by Step

Now that you have all of your pegging supplies and accessories, it is time to get our pegging party started.

Get Turned On– Like all sex acts, pegging is best when everyone is turned on and ready to play. Unlike a woman’s pussy, the anus isn’t self lubricating. So getting turned goes a long way to help a guy relax for the pegging to come.

Fingering– The next step in helping a man get relaxed is to finger his all. I like to start around the rim of his asshole, and use my fingers to massage the muscles around his asshole. Then slowly working my finger into his tight little hole until he is totally turned on and relaxed.

Lube Up– Grab your lube and make sure that you have plenty of lube on his asshole and your strap-on. You want to use enough lube so that your strap-on goes is smoothly and doesn’t hurt.

Slide it In– Once you’re lubed up, take the tip of your strap-on and press it against his asshole. Slowly sliding it into his ass. Once you’re inside of him, you can adjust your stroke to what feels best for you both. Personally, I love bottoming out in a guys ass so that I can grind my strap-on against his prostate.

What do you think about pegging? It is something that you’ve been curious to try? Let phone sex operator Katrina talk you through a pegging experience that will blow your mind! And if you’re a sissy reading this, check out my sissy training guide.