Skip to content
Free shipping to canada and US on orders over $100!
Free shipping to canada and US on orders over $100!
Pegging: My First Time + 101

Pegging: My First Time + 101

My boyfriend was no longer asking, he was practically begging that I get over my nerves and peg him already. I had been telling people that I was into pegging long before I had actually ever done it. I figured it was something that would eventually be a staple in my sexual repertoire, so I wasn’t really lying right?

The nerves I felt were very real. I was imagining horrible and awkward situations that we might find ourselves in: what if I hurt him? How will I handle the dysphoria if the dildo falls off? What if he shits on my white sheets? Thankfully, I didn’t also have to worry about my boyfriend thinking that once someone went into his butt, the gay button would be turrned on. A moment of silence for the prostate owners that will never feel a full body orgasm because of… all of that nonsense. 

What stressed me most though was the fear that I might not be able to disassociate having a dick from being masculine, and what if even worse, I adopted traits of toxic masculinity? But once I had that sucker on and I saw that butt glowing in the red light, I realized I could use this as an opportunity to confront my conditioning, one loving thrust at a time.

Talking About It 

Ya’ll are going to need to have a conversation (we had a few) before you get anywhere close to action. It’s important that you discuss what might be triggering to either of you and what you’ll do, should something happen during play. I’m a huge fan of the light system, green is “good, keep doing that”, yellow is “the action/speed/intensity that is happening right now needs to stop or change but let’s keep playing”, red is “stop everything, this isn’t working”. A pre-convo is also a good time to discuss any potential power dynamics you might want to explore. 

Buying the Right Bits 

If the butt in question has never been played with, a big ol’ dildo is likely too ambitious of a place to start. If I asked you to lay on your belly and bring your head back to your toes, could you do it? You’ll need to stretch. Get your hands on a set of silicone butt plugs in a variety of sizes and start with some training. Incorporate the plugs into your play or task the human that owns the butt to plug up while washing the dishes, zooming their boss, or whatever tickles you. When it’s time to buy your dildo + harness, I highly recommend you invest in the good stuff. As the one wearing the goods, you’ll notice very quickly how important it is that the harness fits you. The dildo you choose for a first timer should be not too soft (that it falls off you and out of them) and not too hard that you break their butt. They may also want to consider an emena kit, which has a device that fills the rectum with water to flush their insides. You’ll need to do this a couple of hours before you play. Oh, and buy lube, like, a lot of it. 

bonjibon - Beginner Harness Pegging KitBeginner Harness Pegging Kit

Warming Up The Butthole 

When you’ve worked your way up to the main event, go ahead, stick it right in there! If you want them battered and in tears that is. I tried knucking my partner, a technique I really enjoy being done to me. Close one hand into a fist and cover the knuckles in lube, then slowly glide your knuckles up and down or in a circular motion around the anus to prepare the area for sensation and relax the outer sphincter. Then you can move on to your fingers (don’t forget to cut your nails). Your fingers might be welcomed in right away, but moving past the second, inner sphincter will likely require you to slow down again. Pushing too fast through this stage may result in tears anal fisures. 

Once You’re In There 

When your human seems relaxed (and is perhaps now desperate for you), you can put the condom over your dildo and lube up again. I asked my partner to get on top of me as our first position, this way he had complete control over the depth of sensation and I didn’t have to worry about my rhythm just yet. When he said he was ready, I took him from behind and braced myself- this was the moment I was afraid of. I’m not going to lie, finding my pace and figuring out how to move was awkward at first, but it got easier with each passing thrust. The last position we tried was missionary, so he could use his hands to touch himself. I recommend that even if you are playing a role, you remember to have fun and enjoy yourself.

Aftercare 

Once he was finished, I let him tell me when to pull out. So I did, slowly, and just lay there next to him, stroking his head and pulling him close to my body for warmth since he’d started to shiver. I told him how proud and impressed I was using language and tone that we had discussed in our pre-play conversation. No matter how cozy and cute and cuddly you’re feeling at this point, you’ve gotta get up to toss the condom, wash the toy, and any of your own bits. 

 

Listen, things are going to happen. Yes, shit things. The enema technique has worked wonders for us, but just to be safe,  we play with a towel and some wet wipes close by. I’ve slowly started to get more confident in my rhythm while thrusting, and have started to figure out for myself what kind of dick owner I want to be while I play. If you take your time with love and care, you’ll figure out the same for yourself. 

About the writer

Yaz

Yaz (they/them), is a queer, non-binary, POC human from Toronto who prioritizes pleasure. They're sick of societal shame that pressures people to hide parts of themselves to be more digestable, so here's the deal; Yaz is a movement encourager and a sex worker. They teach sensual, playful based movement practices as a way to develop self-intimacy and take space in the world of sensual domination. When they're not in the middle of living the things, they're probably writing about it.

Check this out! The Benefits of Masturbation
Have you read? Painful Penetration: One Human’s Experience With Vaginismus

Leave a comment

Comments will be reviewed and approved before being published.

* Required