Skip to content
LET THE FESTIVITIES BEGIN! Save 25% SITEWIDE + Get ANY 5 Gläs Toys for only $99!
LET THE FESTIVITIES BEGIN! Save 25% SITEWIDE + Get ANY 5 Gläs Toys for only $99!
First Time Pegging? Here’s what you need... - Guide to Glass by Gläs

First Time Pegging? Here’s what you need...

The Peg Game

Remember going to a roadside diner, waiting for your food, and while absentmindedly sipping on your beverage of choice, you tried to make sense of the triangular board game with the golf tees? Those were the days when your first time pegging was something you argued with your siblings about in front of your carers, but the term “pegging” has taken a turn. That was the pegging we all knew and loved, but mostly because of its familiarity and not because of an actual affinity. First-time pegging came with oversized cheap food, unbearable background noise, and visual memories of forgotten conversation. 

This ain’t that.

What is it then?

Pegging, coined in 2001 by Dan Savage’s audience, is now known as the name of the act when a person without a penis wears a strap-on dildo and penetrates the anus of a person with a penis. In recent years, it has expanded to mean that this same person without a penis who wears a strap-on dildo can anally penetrate whoever is game, and in some cases, perform double penetration. 

--record scratch-- 

Yes, pegging is defined as when a vulvatized person penetrates a peniled person. And yes, I just made those words up in the same way people will make up the theory that a man being penetrated by a woman makes him gay. The only thing that makes a man gay is his love for another man, not the stimulation of his prostate gland. By that “logic”, a patient receiving a prostate massage from his doctor has transference phenomena as a result of a medical procedure. Stimulating the P-spot doesn’t change anyone’s orientation, no matter who is milking him and no matter if it is only your first time pegging or not.

But… does that make me gay?

Why would a straight man want to be booty banged? Because it feels good. Not only does pegging stroke the prostate, aka P-spot, but it allows a powerful exchange of power. Opening up and allowing a person inside of you is an incredible display of vulnerability, and women are automatically expected to perform in this way. When a man allows penetration, they are able to empathize with that experience in a way that makes them more mindful in future sexual exchanges. The aforementioned feel-good isn’t just physical. Your first time pegging is emotional and mental, allowing you to align with the experience of your partner.

Just as intense is the experience of the giver being allowed access to the inside of a person’s body. To be trusted with that level of vulnerability commands a level of dignity and respect, and that’s before the physical aspect of the experience. During first-time pegging, many receivers have no idea how much work a giver puts in to make sex pleasurable for both parties, so in as much as respect is given in accepting penetration, it is also earned when performing pegging.

What about for women?

But can we get back to how good it feels? Women who enjoy anal sex don’t always have a P-spot (when they do, I’m sure they will tell you it’s amazing), but even the ones who are working with a G-spot can feel an intense sense of pleasure. To be honest, not as much is known about the G-spot as should be, but what we do know is that it varies in size and specific location, and is likely much bigger than we thought. The erectile tissue goes far beyond the clitoris and in some bodies, expands in a way that makes it anally accessible. For some women, the feeling of fullness is incredibly satisfying, but first-time pegging allows that fullness to be accentuated by the stroking of erectile tissue. When engaging in double penetration, there is the sense of fullness from both holes, the erectile tissue being stimulated in the front and back, and the direct stimulation of the clitoris. It can be a salacious sensory heaven. 

The best part about first-time pegging is that all parties can receive a rush of dopamine from “new” sex. Let’s face it, things can get boring. Whether the partner is the same or the routine is, in fact, a routine, sometimes it is hard to get that rush you feel when you have a new kinky experience. Switching up your sex flow with something many consider taboo is a great remedy for the slumps.

First Time Pegging

But now what? You wanna smash some ass but you have no idea where to get started. Before first-time pegging, you need to have a chat with your intended partner about whether pegging is something they are up for. Make sure you are in a neutral space, time, and mood. Right before or after sex is not the right time. A long car ride, over dinner, or during a TV show where it comes up is a much better situation.

Once it’s understood that this is something you are both game for, start preparing. Get clean with a shower or bath, and have plenty of towels prepared. If your partner has never done anal stuff before, you can’t just go shoving a big old dick up there. Start with beginner anal beads or anal trainers. Once your partner is ready and able to take a dick, start slow and with a LOT of lube. To do pegging, you will need a sturdy harness or a strapless dildo. If you are looking to do some double penetration, you can try pegging your partner while manually using an extra dildo for the vagina or you can get a strap-on dildo made specifically for double penetration.

No matter your approach to pegging, this is one of those sexual acts that requires some aftercare. It can be a lot to take in, and there may be some feelings that come up afterward. These feelings are completely valid, even if not permanent. This kink challenges a lot of social norms and the process of unlearning stereotypes and assumptions in real-time requires some tenderness and compassion. Cuddling and talking are usually the order of the day, but silence and presence can be just as powerful. 

Remember that pegging is kinky and erotic, but it can also be deeply emotional and transformative. With the right partner, the right strap-on, and a LOT of lube, you can slip your way into one of the best positions you have ever experienced.

Previous article NIPPLEGASM! In search of the coveted Nipple Orgasm
Next article Cock and Ball Torture 101: A Game of Tug-of-War You'll Want to Lose