How to Gape His Hole

My name is Alexander. My nickname is Beastly. I write about sex.

Have a question? Email askbeastly@gmail.com or go here.

This site is supported by readers — not ads. Visit my Patreon to support my work and get xxxtra special perks.

I want to gape my boyfriend but have no idea how to safely do so. Could you offer some tips on how to do that? Thank you!

Hi friend,

I sure can! I bought a small black butt plug made of PVC sometime near the beginning of college which I used once, hated, and left in a drawer. Four years later, an ex-boyfriend found it and asked if we could play with it. I said OK but told him it wasn’t fun (I was wrong).

We lubed it up (we used Pjur Back Door Silicone exclusively throughout our relationship), I bent over doggy-style on the bed, and he started pushing it in. At the time, I was very tight. He pushed forward a millimeter or two before I said “Stop!” We did this — forward, stop, forward, stop — for what felt like twenty minutes until it finally slid in.

Once again, I didn’t think it felt good. Frustrated and ready to move on to sex, I told him to slowly pull it out. He started tugging on it gently — and something happened. I told him to tug on it without pulling it out. He did. That’s when I think I started moaning. When it finally popped out, I asked him to slowly push it back in. “OK, pull it out again slowly.” He did. “Again.”

He gradually increased speed until he was basically fucking me with it — pushing it in and pulling it out rapidly — and I was gaping. That feeling — the sacred pullout, the tug — is how I got better at sex and eventually discovered fisting. It’s the feeling of your hole being forced to open around an object. After a month, we bought a bigger plug. He loved seeing me gape and I loved how it felt.

He always followed my direction until I loosened up and let him take over and go fast. After I was gaping, he could slide his dick in and immediately start fucking hard, and it didn’t hurt because I was loosened up. The process of loosening my ass — which for many bottoms happens during sex, which is why the first several minutes of bottoming are often painful — became a central part of every session and made the fucking so much better. After he and I broke up, I worked up to bigger plugs until I was taking hand-sized objects. One day a guy slipped his hand in. The rest is history.

Gaping happens when you pull something out of an ass (toy, cock, hand) quickly so the hole doesn’t have time to close up. At IML some years ago, a customer came to the Fort Troff shop asking about “pistoning,” which I’d never heard of (I have never found a reference to “pistoning” in porn so I don’t think it’s a widely used term). He explained that “pistoning” is fucking someone with a plug to make them gape — exactly what I loved. I’ve also heard this called “plug fucking” or simply “gaping.” (The plug he recommended is the “world’s most comfortable butt plug” by Mr. S Leather — that’s the name they gave it — which I’ve used. It’s not my favorite plug for this kind of play but my boyfriend loved it. My favorite plug for pistoning is a heavy glass plug I own which is similar to this one.)

Whatever it’s called, the first time you try it, let him direct. Stop when he says stop, go when he says go. Speed up when he tells you to go faster. You must be patient and use lots of lube, but if you piston his hole with a plug, you’ll see a beautiful gape. If he wants a bigger gape, he’ll have to work up to bigger plugs (and, if he’s into it, hands). If you can, find a plug with a chunky base that you can easily grip, even when it’s covered in lube. A great plug for this is the Egg Plug by SquarePeg, which comes in many sizes. Trim your nails, since you’ll probably finger him a little bit, and as you grab the base of the plug to pull it out of his ass, your fingertips will scrape his hole. File them down to nubs.

Start with a simple rounded or teardrop-shaped plug, no weird shapes (I’ve never understood why someone would want the equivalent of a gnarled tree branch in their ass). Google “round butt plug” or “ass trainer kit” and you’ll find hundreds of options. PVC, like the one I started with, is a good material, but premium silicone is arguably better. You cannot use an oil-based lube with PVC and you can’t use silicone lube with many silicone toys, so the material you choose determines the lube. The only toy materials I suggest staying away from are TPR, TPE, and plastic. Hard, sticky, jelly toys (most dildos in standard sex shops) are too hard and not designed for anal play.

I love my gape. He will too. Merry Christmas.

Love, Beastly