Sex writer Alexander Cheves answers all of your questions on anal sex
#Ass Me Anything

Ass Me Anything: Am I Going Too Far?

Last Updated: Jan 15, 2024 / By Alexander Cheves

Looking for some anal answers? Our first edition of Ass Me Anything with Alexander Cheves is here to put your ass-umptions to rest!

We know you have butt on the brain. The b-Vibe team receives many questions about proper plug use, anal prep, ass play, and more. So I'm here to help.

My name is Alexander Cheves. I write about sex, and I am a butt guy. I am a cisgender Queer male who loves all kinds of anal play, from the mild to the very extreme. My goal is to answer questions and affirm the safety and wonder of anal pleasure.

With that out of the way, here are some questions we have received from you!

Q: My wife's fingers are great at stimulating my prostate, so we decided to get a plug for some extra fun, but I find that it doesn't feel as good. It doesn't feel bad, it just doesn't feel like it's stimulating my prostate as much as her fingers do. Is there something we are doing wrong?

A: I wonder what kind of butt plug you got. When I started anal training, my trainer made me put in a butt plug — a small one, easy to take — then asked if I knew the purpose of this exercise. I was confused. The purpose? I tested an answer: "To make me feel good?" Sure, but that wasn't the main reason why we were using a plug. "It's to squeeze on," he explained, "to train the muscles of your ass."

Doing kegel exercises with an anal plug is a great way to train your butt for anal pleasure

All muscles need work to grow flexible and strong, and for the kind of heavier ass play I wanted to explore, I learned to train more heavily. I sit on a plug almost every day and even do Kegel exercises while plugged. Anal sex training helps the sex I like to happen more comfortably and enjoyably. That is the primary purpose of a plug — they are useful and enjoyable tools for people looking to train their butts.

As someone with a prostate, I can say that a standard butt plug should stimulate the prostate very much. A plug may feel good — indeed, being plugged can feel incredible — but the standard designs of tapered plugs (teardrop, rocket-shaped, and so on) are not made to maximally hit the prostate in the way your wife's fingers can. I would recommend you try an insertable toy designed specifically to hit that glorious P-spot. b-Vibe has an excellent selection of P-spot toys or you can check out this complete guide on how to have a prostate orgasm.

Q: I was wondering if it is safe to wear a plug for long periods of time. Specifically, I want to wear a plug while I am out-and-about running errands. I know it might sound a little strange, but there is something exciting about wearing a plug out in public. Will it hurt me in any way if I wear a plug all day?

A: I don't know what circles you're running in, but there's nothing strange to me about being plugged on a grocery run. In fact, being plugged for extended wear periods is common among folks into butt play. I've gone to the gym plugged (not super recommended, but I've done it), danced all night plugged, and even slept a full eight hours plugged. Doing this is fun and feels good. 

Learn how to wear a butt plug out in public

I'm not a doctor, so I won't say decisively that any activity will or will not hurt you, and the advice here should not be considered medical consultation. Always talk to a doctor if you have health concerns. But as an experienced plug user, I can say I've never heard of someone being injured by wearing a plug for a few hours. At some point, you will have to use the bathroom and remove the plug for a little bit, but there's no rule saying it can't go back in after. [Just don't forget your lube!]

All this said, not all plugs are the same, and those that are not designed for ergonomic movement will not be very comfortable in extended-wear sessions. Generally speaking, the best plugs for this have a flexible stem, more like a cord, connecting the base to the body of the plug, and the base should be curved to match the curvature of your body (this will help with sitting and moving about). I recommend the Snug Plug series from b-Vibe.

Q: I have tried a few plugs now and they feel amazing! I want to try the next size up, but the one I am currently using is already a lot bigger than I expected I'd ever to be using, and I am worried I might be doing permanent damage to my body. Do you have any tips for how to use larger size plugs without doing permanent damage, or should I just stay happy with the ones that I have? I want to experiment, but not if it means my butthole is going to never be the same again.

A: A common myth widely circulated about orifices — front and back — is that use makes them loose, and large objects ruin them. This is false. Anatomy doesn't work that way. Your ass is elastic. It tightens back up after you play in it.

If you want to go bigger, go bigger. I could point you in the direction of many people who take toys so large that they defy the imagination, and none of them are incontinent. Their butts work fine and look, for the most part, like normal butts. These folks have simply trained, gone slow, used appropriate lube, and worked up to larger and larger toys over years of practice.

The myth of "loose holes" has been used to shame and police the sexuality of women (our culture literally brands sexually active women and prostitutes "loose women").

No, you are not doing permanent damage to your body. The anal sphincter is a muscle designed to open and close, and with training (with plugs and more), it can open a lot.

I enjoy anal fisting — full-grown human hands regularly go in my butt, sometimes very fast — and yet, as I write this, my butt is normal, closed back up, and looks and operates like a normal, healthy butt should. I am not incontinent or "loose." You may not have extreme ass-pirations, but butt-training is basically what you're doing. You could go very large if you wanted to, with time and practice, and your butt will still tighten back up, probably instantly, and function as a butt should.

There's no pressure to go big, but don't let non-scientific myths about the body keep you from doing what feels good!


That concludes our first edition of #AssMeAnything, but just in case you're still searching for answers, below are some helpful guides to our most frequently asked questions!

1. What is analingus?

2. What's the difference between an anal massage and anal fingering?

3. What are the best anal sex positions for beginners?

4. Help! I want to learn how to prepare for anal sex. Where should I begin?

5. A 101 guide on how to take good booty pics!

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