pegging — Pleasure Mechanics

Pegging and Prostate Play

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Pegging is when a female wears a strap-on dildo to anally penetrate a man. The term “pegging” was coined by Dan Savage’s audience. Previously, terms like “bend over boyfriend” were used to describe the same act.

There is nothing new about pegging. Versions of strap-on dildos have been depicted in erotic art for thousands of years! In recent years, however, more men are coming out about their desire for anal penetration. As more men openly discuss the pleasures of pegging, it gives other men permission to explore this sex act and discover just how orgasmic it can be.

Pegging and prostate stimulation go hand in hand. Before you go all the way with pegging, it is essential to explore anal penetration with fingers and small toys. Fingers are the best tools for anal penetration and prostate stimulation.

Many men report that prostate stimulation leads to the strongest, most intense orgasms they have ever experienced. In this interview with Cooper S. Beckett, he describes his first prostate orgasm, and experience he says totally changed his sex life forever! Cooper reports that once you “level up” your orgasms with prostate stimulation, every other orgasm you experience can be more intense.

So if you are curious about pegging and prostate play, tune in to this podcast by hitting the “play” button at the top of this page.

Ready to discover the power of prostate orgasms for yourself? Check out the Prostate Massage Mastery Online Course now!

Cooper is the founder of LifeontheSwingset.com & host of its swinging & polyamory podcast. He speaks and teaches classes on pegging, swinging, polyamory, play parties, and non-monogamy. He has written two books.My Life on the Swingset: Adventures in Swinging & Polyamory & a new novel about swinging, A Life Less Monogamous. Use the code “pleasure” to get 10% off the new book!

You can get his book My Life on the Swingset: Adventures in Swinging & Polyamory as a FREE audiobook on Audible.com with your free trial membership. Click here for your FREE audio book!

Q&A : Relaxing During Anal Penetration

Question::

Hey Charlotte and Chris!

Thank you for being so open and accommodating; with good people like you offering friendly advice, there is indeed hope. Since you offered, here is my query;

I am a male in my mid sixties (what I used to do all day, now takes me all day LOL), and I am interested in pegging. My partner and I have tried a couple of times, but I am, as yet, unable to relax sufficiently to take anything more than a modest butt plug. We tried twice with her wearing her strap-on but notwithstanding that I KNOW it will work, she notices my grimaces and stops; it simply hurts, and she cares too much! I guess I’m just too nervous?? L Do you have any “relaxation” suggestions please??

Thanks again!

Karl

Answer::

Hey Karl,

Thanks so much for being in touch!

Awesome that you are actively exploring this kind of pleasure!

Here are a few quick suggestions to help you relax and open up to bigger penetration:

First, make sure that you are fully pleasuring the external anal area before ever going inside. The ass needs to be seduced, as the internal sphincter is not under your conscious control. If you haven’t already, join our online course: Prostate Massage Mastery. You’ll learn everything you need to know to really relax the area and create tons of pleasure, which will help your body relax and open up to penetration.

Then, focus on your breathing. As she begins to penetrate you (ideally with fingers first to give you lots of pleasure as she goes in, then she can switch to a toy once you are really aroused and open!!) focus on deep relaxing breaths, trying to feel your pelvic muscles relax on each inhalation. You can even over emphasize this until your body learns to do it naturally – as you deeply inhale, push out a little on the pelvic floor muscles, then let them relax back on the exhale.

Next, try clenching around the penetration – flex your sphincters as she enters and see if that helps relax them.

Make sure there is no pain at all during penetration – going too fast, not using enough lube or pushing past resistance will create pain and shut your body down no matter how much your brain wants it!

It may take a number of sessions to relax into bigger penetration – but know that most of the arousing sensation happens in the external anal area, so there is no need to rush into pegging! Master these skills with our online course on prostate massage, You’ll even learn the ultimate way to enjoy simultaneous prostate and penis massage, to unlock tons of pleasure and invite your body to open up as you go.

Be in touch if any questions come up along your journey.

All our best,

Chris and Charlotte

The Pleasures of Pegging

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What Is Pegging?

Pegging is the erotic act of a woman wearing a strap-on dildo and anally penetrating a man.

This act, popularized first in the “Bend Over Boyfriend” video series, has been depicted in erotic art throughout history and across cultures.

The term “pegging” was coined by sex columnist Dan Savage, who recognized the surging popularity of the act and thought it was time this act had a good name. The term pegging stuck, and it is now one of the most popular fantasies for heterosexual men.

Why Does Pegging Feel Good?

Pegging can be a highly pleasurable act, for both partners. The anus is one of the most highly sensitive parts of the human body, and many people love the sensations of both external and internal anal stimulation. Some people eroticize the gender play of seeing a woman wear a strap-on and take on the penetrative role in sex. Others just love the sensation of being “filled up” and enjoy the sensations of anal penetration with a strap-on toy.

Many women love the feeling of being in charge, of switching up the roles of intercourse and watching their male lover respond to the sensations of being penetrated. When a strap-on is well fitted and positioned, the base of the dildo grinds into the clitoris and pubic bone, offering pleasurable stimulation with every thrust. There are also harness and dildo models that allow a woman to wear a vibrator, or even a double-ended dildo that allows both partners to be penetrated at the same time.

How To Get Started With Pegging

Anal penetration is intense and must be taken slowly in order to be pleasurable. If rushed, anal penetration can be painful, leading to lasting injuries. So go slow!

If you are new to anal stimulation, we highly recommend starting with your fingers to begin exploring the external sensations and the slowly proceed to penetration with just one little finger, allowing the slow relaxation and opening of the anal sphincters. Our best advice is to join our Prostate Mastery Course. This online course guides you stroke by stroke through highly pleasurable external and internal stimulation. Once you master the techniques in this course, you will be ready to proceed to penetration with a larger strap-on toy and the full pegging experience, if you so choose.

Pegging Toys

Click here to check out some of our favorite pegging and strap-on sex toys at GoodVibes.com