Pegging and Male Chastity: Why You Should Try It and How to Do It

Posted by Andrew Schroeder on

Mistress getting ready to peg her slave
2001 was a big year for anal sex. It was the year columnist Dan Savage asked his audience, “What term, from this day forward, will be the commonly accepted slang for a woman fucking a man in the ass with a strap-on dildo?”
The audience had three options to choose from:
  1. Punt/Punting.
  2. Bob/Bobbing.
  3. Peg/Pegging.
In the end, they settled on option 3, possibly because putting in a peg in a hole best represented the act.
While pegging is a relatively fresh term, guys have been taking it up the ass since… well, forever. But when did strap-on pegging become a thing?
Ancient Egyptian, Roman, and Grecian artwork shows evidence of penetrative sex using strap-ons. And in The Pleasure’s All Mine by historian Julie Peakman, she discusses how women in the Medieval era made or bought strap-ons for sapphic encounters. And while it’s tough to know for sure whether they were ever used to peg a male, given humanity’s track record we can guess that curiosity got the better of at least one Medieval man.
Attitudes towards anal sex are changing. It’s just another way to have sex.
Research from Bedbible.com brings what we know about pegging and anal sex up to date. In the largest global study on the subject, they found that:
  • 43% of men have tried anal.
  • Nearly 17% of respondents have tried pegging.
  • On average, Americans have anal sex 2.57 times each month.
  • Nearly 49% of Americans have used anal toys or fingers with a partner.
  • 44% of Americans said they’re somewhat or very comfortable talking about anal sex.
Couple these stats with healthy sales of strap-on sex toys (according to retailers), and you can conclude that attitudes towards anal sex are changing. It’s just another way to have sex.

Pegging Cameos in Film and TV

It seems the media always needs a sex act that’s considered ‘taboo.’ For a long time it was anal sex in general, which slowly morphed into cishet guys enjoying some ass satisfaction.
But even this is changing.
Films such as Deadpool and TV shows such as Broad City include storylines involving cishet couples who peg. And it’s good to see. It adds to the narrative that normalizes strap-on sex. It’s just another way to do it.
Ultimately, seeing it in mainstream media is a declaration there’s nothing wrong with it or weird about it. It’s simply how some people get their kicks.

Exploring the Pleasures of Pegging - A Guide for Guys in Chastity

If you and your keyholder are looking for ways to be intimate that doesn’t involve taking off the chastity cage, pegging is an option. But how do the two kinks marry up?
In this article you’ll find:
  • What pegging is, and how its definition has changed.
  • How it delivers pleasure for both giver and receiver.
  • How to prepare for your first pegging experience (physically and mentally), including what kit you’ll need.
  • How to enjoy it alongside chastity play.
Two pink cock cages

The Definition of Pegging, Then and Now

The original Dan Savage callout was to label the specific type of sex where straight women penetrate straight men using a strap-on. That was the definition. This is why the examples of pegging in film and TV have so far been between a cisgender, heterosexual woman and her cis male, heterosexual partner.
But language is a funny thing. Terms (especially slang) often evolve and take on new meanings. For some, pegging means anal sex using a strap-on regardless of gender or sexuality. But there’s some pushback against this. Not everyone in the trans male community wants the sex they have reduced to a term originally coined for female-to-male cishet anal penetration.
Fence sitting isn’t ideal. But as someone who believes sex is about exploring what you find comfortable, I say each to their own. If ‘pegging’ describes the type of strap-on anal sex you and your partner enjoy, and you’re both comfortable with that, then use it.

What’s So Great About Pegging Anyway?

If you haven’t tried pegging yet but find the idea appealing, you might be wondering why. Well, here are a few good reasons.
Your butt is super sensitive.
As with other erogenous zones, there are thousands of nerve endings in and around the anus. Stimulating them when you’re sexually aroused can feel amazing.
For guys, it’s also where you’ll find the prostate gland. Roughly the size and shape of a small plum, the prostate produces fluid that protects sperm when it enters the vagina. It also regulates the release of reproductive hormones (such as testosterone) by the brain.
When it comes to pegging, a little friction against the P-Spot can feel mighty fine.
The penetrator becomes the penetratee.
When penis-in-vagina (PiV) sex is available (i.e. the man isn’t caged), the man penetrates the woman. But when a hetero couple peg, the roles are reversed. And the change can feel liberating. Each person gets to experience the physical and mental differences between penetrating and being penetrated.
Pegging can be a BDSM power trip.
Relationships based on a power dynamic (e.g. Dom/sub, female-led relationships) may include pegging to reaffirm each person’s role. During play, a Mistress can use it to humiliate their sub and assert their dominance. Of course, this works only if those involved prescribe to traditional ideas about sex—that being penetrated puts you in a weaker, more effeminate position. (It doesn’t. But this thinking is why men who like being penetrated may be labeled a sissy.)
Stimulation for the strap-on wearer.
Sex works best when there’s something in it for everyone. And strap-on sex is no different. For her, the sensation of the clitoris and labia rubbing against the harness, or wearing one fitted with a clit vibrator or dildo, means she gets physical stimulation as well as the mental pleasure that comes with riding her man.

Pairing Pegging and Chastity Play

The two kinks go together like chocolate and pistachio.
For those in a D/s relationship, both kinks emasculate the man. Chastity stops the guy using his penis, and pegging puts him in the submissive sexual role. (He takes it rather than gives it.) But you don’t have to be into power play and BDSM to enjoy pegging.
Using a strap-on allows you to have sex with your partner without unlocking and breaking your current pledge. Leaving the cage on can feel good too. The extra friction as you’re rocked back and forth by your partner’s thrusts can feel both torturous and amazing.
Three pink cock cages

5 Tips When Shopping for a Strap-on

You can’t peg without the proper kit: A harness, O-rings, and a dildo. But what should you look for?
Tip #1: Check the harness size and fastening.
An adjustable strap-on harness makes finding the right fit easier. It also gives you more freedom. Depending on the harness’s minimum and maximum waist measurement, a single harness could fit you and your partner. (Yay! Sex toy sharesies.)
You know a harness is a good fit when it feels secure around the hips and legs, and doesn’t slip or come loose when you move around.
Different harnesses also have different fastenings. Some use Velcro, while others have buckles. An easy style is one you can just slip on and tighten the straps.
Tip #2: Check the washing and cleaning instructions.
Your harness will be exposed to mess (lubricant, sweat, bodily fluids, etc.) Keep your play safe by keeping your strap-on clean.
Some fabric harnesses can be tossed in the washing machine, which makes cleaning up quick and easy. Others can be hand-washed. A leather harness should be wiped with a damp, soapy cloth. And when it’s dry you can use a leather cleaner or conditioner to keep it looking schmick’.
Tip #3: Are the O-rings interchangeable?
An O-ring fits to the front of the harness and keeps the dildo in place. The front panel of some harnesses have snap fastenings so you can change the size of the ring, which gives you more freedom. Pretty much any dildo will be compatible with your harness. You just need to find an O-ring that fits.
Tip #4: Choose a dildo with a flared base.
Looking for a harness-friendly dildo? Look for one with a flared base. It will sit flat against the harness, but its wide base means the O-ring can hold it in place.
Tip #5: A bigger dildo isn’t always better.
When starting out, the size of the dildo should reflect your anal sex experience. If it’s your first time, or you’ve only recently added anal penetration to your sex repertoire, choose a beginner’s strap-on dildo. They're usually thinner and smoother.
Extra tip: Beginner dildos are a good option for first-time wearers, too. They’re small and light, which makes them easier to control.

Preparing for Your First Pegging Experience

So you and your partner have talked it over, and strap-on anal sex is something you want to try. Whenever there’s something new on the agenda, how you imagine it will go is usually a lot different from how it actually turns out.
Doing a little ground work (which you seem to be doing) can bring imagination and reality closer together. Trying one or more of these pre-pegging activities can help keep the fantasies and expectations in check so you have a better time when The Day of the Pegging arrives.
The First Time Might Not Be Great
New sensations, sex accessories you’re not used to, and first-time nerves can result in a pretty average experience. And that’s pretty normal. As with most skills, the more you practice the better you’ll get. Don’t be disheartened if you or your partner don’t climax, or you find it a little weird. When you’ve finished, discuss what happened and whether you both enjoyed it enough to try it again.
New sensations, sex accessories you’re not used to, and first-time nerves can result in a pretty average experience. And that’s pretty normal. The question is, did you enjoy it enough to try it again?
Get the Butt Ready
Anyone indulging in anal play may encounter some shit. It’s part and parcel of playing with the area it comes out of. If that concerns you, you may want to try anal douching next time you’re in the shower.
It’s also worth remembering that the sphincter is a muscle. And like all muscles, it can be tight or relaxed. When it comes to anal sex, a relaxed butt muscle can make proceedings easier.
A warm shower or bath can help, as can stimulating your other erogenous zones to get you in the right headspace.
Be at One With Your Strap-on
You should both get to know:
  • How the harness works.
  • How it goes on.
  • What it looks and feels like against the skin.
  • The feel and shape of the dildo.
Various Cock Cages
But if you’re the wearer, you should also spend some alone time with the strap-on. Wearing it before you plan on using it can help build a connection. Admire yourself in the mirror while wearing it. Feel it. Touch it. Stroke the dildo like you’re masturbating. You could even ask your submissive if they’d be willing to suck your strap-on cock.
Put Your Best Thrust Forward
First-time wearers often say the constant thrusting is exhausting, and that it’s hard to get into a rhythm. So before the main event, build up your stamina and skills by practicing.
And if you do get tired during anal sex then take a break, go slower, or make smaller movements. Sex is rarely a continual high-octane, jackhammer experience.
And Now, the Main Event
Here are some tips to make the main event a successful one.
  • Use plenty of lubricant. The anus isn’t self-lubricating, so having a bottle of lube on hand is essential.
  • If there’s any pain, slow down or even stop. This is your body’s way of telling you something’s up.
  • Keep communicating, and make sure you’re both comfortable.

The Bottom Line (Pun Intended)

Your reason for adding ‘get pegged’ to your sexual to-do list will be personal to you. You may be doing it because you want to:
  • Know what anal sex feels like.
  • Challenge your ideas around gender and sex.
  • Make it a power dynamic in your relationship.
Understanding why you want to do it, and what you want from the experience, will make it easier to talk to your partner, keyholder, or Dominant about it.
Which I expect is the next step in your pegging journey.

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About The Author

ANDREW SCHROEDER

Our guy who’s walking the walk, Andrew is a long-term cage wearer who found LTC when shopping for devices early in his journey. So he’s gone from customer to consultant. 

He taps out articles that discuss the lifestyle. From debunking myths to offering commentary on the most-debated chastity topics, Andrew S is inspired to write because of his ardour for the caged life.

“Pardon the pun, but there’s a lot of cock and bull information about male chastity and the people who partake in this lifestyle. My want, and why I write for LTC, is because I believe we need more straight-talking, experienced voices to speak up about their journeys with chastity. People who are familiar with the lifestyle and community. People who want to help those who are new and interested."

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