What Happened When I Pegged My Boyfriend With A Strap-On Dildo
To peg, or not to peg, that is the question. And for me, the answer was hell yeah, let’s peg.
I’m a Certified Sex Educator so I’m always looking for new ways to explore pleasure and pegging has been on my sex bucket list for some time. Luckily for me, it was on my boyfriend Jay’s list too. So, we strapped ourselves in.
First things first, what is pegging?
The term pegging was first coined by the sex columnist Dan Savage and his followers to describe a cis-woman anally penetrating a cis-man with a dildo. It’s now evolved to be more inclusive than that and most people use it to describe any form of penetrative sex with a strap-on dildo. The way I see it, pegging is for everyone!
That’s why I often use the term strap-on sex instead. It doesn’t matter your gender, your sexuality, or what genitals you are rocking, anyone can enjoy strap-on sex with a partner. Not to be reductive, but literally all you need is an orifice.
The prep
I’m a cis-woman and my partner is a cis-man, so I wore a harness and a strap-on dildo and used it anally on him.
For us, pegging is not a spur-of-the-moment activity as it does require some preparation to ensure the booty is prepped and ready for action – and not just the day of.
An anal dildo is not necessarily a starter toy. Even small dildos are going to feel huge in a butthole if you’ve never had anything in there before. Start with inserting a finger, anal beads or a small butt plug first and work your way up to the dildo you want to use for pegging. Please never go from zero to dildo!
Jay had a shower and used a douche about 30 minutes before to ensure that he was completely clean but that’s not a prerequisite – it’s about your comfort level and what is going to allow you to play comfortably without worrying.
Speaking of, if you’re worried about poop, I get it. Sure, it’s the butt, but I have good news. Poo is stored in the rectum not in the anal canal which is where the dildo is going to be. So as long as you don’t need to go to the bathroom (right now), you don’t need to worry too much. There is a small risk of residue in the canal, but you might be surprised by how uncommon this is.
If you are concerned, pop a towel down and have some wet wipes handy. Easy!
But there’s also the emotional fun to be had too. We were both so excited to peg. The idea of switching up our normal way of having sex and the intimacy that comes from trying something new together was a big turn-on for us. But it was nerve-wracking too. We are pros at penis in vagina sex but what if we suck at dildo in butthole sex? There is only one way to find out, I guess!
Here’s how we did it
Okay, now that the prep is done, let’s talk gear because choosing a harness and dildo can be a lot of fun. I wore an underwear-style harness and I’m happy I did. Initially, I was a little worried that it wouldn’t be secure enough to hold the dildo in place, but it did a good job. I still needed to guide it in to start with but once we were rolling, it stayed exactly where we needed it to.
The harness came with a small, beginner dildo that was ideal for us. It’s made from silicone so it’s body-safe and able to be sterilized between uses (essential for all sex toys), and just soft enough to go in easily without feeling too firm.
Emma and Jay. Image credit: @emintoyland Instagram
Remember that this is not porn or a TV show. The anus does not self-lubricate, and the dildo will not just slide in. So, use lube! We used a hybrid lubricant with a mixture of water-based lube and oil-based lube that is thick and incredibly long-lasting.
One thing that I already knew about anal play is that it’s a LOT more pleasurable if you’re super aroused and stimulating other parts of the body at the same time. So, there was a lot of foreplay. Plenty of hand stuff and a lot of mouth stuff before going anywhere near the butt.
When we were ready for anal, I had the wise words from my favourite sex educator Luna Matatas in my head. She said to let the person being penetrated move onto the dildo to start with and control the speed and depth of the thrusts while the person wearing the harness simply stays in place. This is obviously going to be easier if you are in a doggy-style position where the person being pegged can move their hips back and forth easily.
But Jay was keen to start with him on his back with his legs bent up to his hips, so this is what we did. It’s a good position for first-timers as you are face to face and can easily communicate with words but also with your facial expressions.
However, we quickly found that this position didn’t work for us. I have hip issues from time to time and needing to have my hips so low to reach his butt just did not work so we flipped around to doggy style instead. This meant I could let him move back and forward on the dildo while we eased into it.
Even though I was using a dildo I was surprised by the biofeedback I felt. The sphincter muscles are seriously strong which is why you may experience resistance when you try to insert something into the butt. But when you make it through, you will feel it. And it is very satisfying!
But, I have to admit, it took quite a lot of work to get the position right.
The size difference between myself and Jay became very apparent. I’m about 5’4 and he’s over 6 foot and honestly, pegging him was kind of hard!
It was still fun but stressing about getting into the perfect position sucked some of the sexiness out of the room for me. Mainly because I was trying to rub his penis at the same time and doing the reach-around was hard. I was trying to keep my hips stable so that I wasn’t moving the dildo out of the position that Jay was comfortable with, but I felt like a T-rex trying to reach around him.
He’s a tall boy with long legs and my wee arms were not reaching where I wanted them to. Honestly, it was kind of hilarious and my arms aching the next few days from trying to keep it up was a fun reminder of the experience.
Going from penetrated to penetratee was more difficult than expected. I was a teenager when Shakira was hitting us with bangers like ‘Hips Don’t Lie’, so trust me, I can thrust my hips, but doing it with a dildo going into someone else’s body is a whole new world. I now also totally understand why guys will sometimes start thrusting hard and fast, it’s super fun! But it did mean there were a few times when Jay had to remind me to slow down. For him, slower, deeper thrusts felt better so that’s what we tried to stick to. And it didn’t take long for him to orgasm from it. The combination of penis stimulation and prostate stimulation from the dildo resulted in a big, happy ending for him.
For those wondering if it felt good for me…
There was some grinding of the dildo against my clitoris which felt great, but I was a little too preoccupied focusing on thrusting just right (and keeping my T-rex reach-around up) to really appreciate it. But I’ll be sure to next time. Practice makes perfect, right?
If you want to try it
My advice is to prep and warm up your body, use lots of lube, go slow, communicate throughout and don’t take it too seriously. We like to have a lot of fun when we have sex so giggles, sore arms and having to change positions was fine with us! But trying something very different to what you usually do during sex can be stressful so try your best to relax and have fun with it.
Image credit: Supplied + Punkee.