After posting our Valentine’s Day article, ‘More Pegging, More Intimacy: One Reader’s Experience’, we received a really powerful email from another reader sharing the story of their first pegging experience. We hope you enjoy.

Pegging My Boyfriend For the First Time (What It’s Really Like)

I never thought I’d wear a strap-on and peg my boyfriend. When I met him, it wasn’t a subject that ever came up, even though we often talked about our sexual fantasies. So imagine my surprise when one night while we were lying in bed, he asked if I would ever be down to peg him.

I’m not going to lie – my initial reaction was to feel a little shocked and uncomfortable. Pegging always had such a negative connotation attached to it and wasn’t something we had ever heard much about. (It’s luckily becoming a little more mainstream as time goes on.) We had played a little bit with a finger or two, and he had even had some solo action with a butt plug, but never anything close to a dildo strapped to another person before!

So I asked my boyfriend what it was that appealed to him about being pegged, and he told me that he felt like a lot of men often missed out on the sensations of anal and prostate play. Then it just clicked for me – it wasn’t fair that there was this whole realm of sexy fun that my boyfriend had never experienced before.

What did we do? We spent an exhausting several hours online, shopping for toys. If you’re thinking about jumping into pegging or prostate play, you’ve been warned – there are a lot of toy options out there, and it was seriously confusing to wade through all of the selection.

After a couple of disagreements (the color of the dildo, what type of harness we liked), we settled on the Sportsheets lace harness and the Blush Nude Impressions vibrating dildo. In retrospect, we definitely were not prepared for any sort of vibrating sensation, so we were a little ahead of ourselves. Regardless, a nice discreet box arrived five business days later.

“Did you get the lube?”

“No, weren’t you picking it up after work?”

The lube! We forgot the lube.

Fast forward a couple of days, when we finally had our trusty lube in our hands. Tonight was the big night, and I was pretty nervous and could tell he was too.

There are a lot of aspects of pegging that we weren’t warned about. My boyfriend had gone into the shower to give himself a good, um, “cleansing,” and that was something he maybe should have tried before the night of the pegging. He was not totally comfortable with the sensation of the water inside of him and getting the flow to properly work. It took much longer than anticipated, so it threw a little wrench in our plans and definitely made him a bit self-conscious.

Another thing they don’t warn you about – the harness is not always the easiest thing to adjust. You’re working with all of these different straps. It feels very awkward to wear a harness for the first time – empowering, yet awkward. I wasn’t sure how to fit the dildo into the thing!

I finally got the dildo adjusted and couldn’t help but giggle. It was very different to look down and see myself with this strap-on. But I was encouraged by how excited my boyfriend seemed. I was excited to do this for him and also see how sex had always looked from his perspective. It gave me a sense of empowerment and also made me realize how much my boyfriend trusted me by letting me experience this with him for the first time.

We had done some research about which position was the best to start with and decided to do the standard doggy style. I brought out the lube, applying it to both the dildo and his ass. I used a lot of lube - a lot. The doggy position was definitely the best choice for us, because I was able to see exactly where the dildo was going.

If I could give any advice to someone just starting to get into pegging play, it would be to talk a lot and to also go very slowly. Even if your partner has had previous solo anal experience, it’s much different when the toy is being guided by someone else.

I slowly put the tip in first, listening to his response and guidance, giving him time to adjust to the width of the dildo. I think the smaller dildo, the better for the first time, because ours was quite large for someone with little to no experience, though it didn’t take him long to get used to it. He finally told me I could start going a little deeper, which I did, with caution. It was honestly amazing to see my boyfriend like this, and to watch his reaction to the pleasure that I was responsible for. I don’t think any other sexual experience between us had felt so intimate, even if it was so new and a little awkward.

The dildo was hard to maneuver for me, the newbie. Looking back on that time compared to every time after that, it was a bit of a bumbling, fumbling experience. I wasn’t able to maintain a steady pace for him because the dildo kept slipping out, and the harness wasn’t adjusted correctly before we started. There was definitely more of a learning curve to the pegging experience than either of us had expected.

In the end, my boyfriend did not orgasm from that first night. I was so upset – all of these articles online made it seem like the whole point was to give your guy this incredible, mind-blowing orgasm like nothing before, and I couldn’t do that. But he assured me it still felt amazing and that just because he didn’t reach an orgasm didn’t mean it wasn’t a fun, incredible time with me.

Overall, I am so glad that we decided to try something new. These days, we frequently play with strap-ons and prostate massagers and butt plugs, and my boyfriend almost always gets an incredible O. Did it take a few times to become comfortable with the toys and each others’ bodies? Absolutely. Was it worth it? Even more so.

My advice to couples who are about to peg for the first time is to take it slowly, communicate with each other, and don’t have expectations about a totally flawless experience. There are going to be moments that make you cringe, laugh, or take pause, and all of that is okay. Don’t let it discourage you from having lots of pegging fun, again and again. . .