Never Have I Ever: Used a Prostate Toy

Have you ever played “Never Have I Ever” before? Here are the rules: Everyone puts up ten fingers, and you go around in a circle and one by one share something sexy or scandalous that you’ve never done before. When someone else shares something you have done, you have to put one finger down — and of course, drink. The first person to put all 10 fingers down loses (or wins, depending on how you look at it).

Well, AskMen is still playing Never Have I Ever, and the rules are simple: In each edition of this column, we speak to someone about doing something new in bed, whether it’s a long-time fantasy, something that just happened, or even something they regret. They tell us everything so you get an inside look at what some sexual experiences are actually like.

Lots of straight guys claim they love pleasure. But how many of them enjoy the hyper-powerful orgasms brought on by using a prostate toy?

That’s right. Cis men and folks assigned male at birth have the P-spot — aka the “male G-spot.”

The prostate is a walnut-shaped gland that sits below the bladder and in front of the rectum. The primary job of the prostate is to produce a fluid that, along with sperm cells from the testicles and a dose of fluids from other glands, creates semen. Prostatic fluid is basically holy. It's crucial to the survival of sperm, accounting for around one-third of the volume of semen.

However, the prostate does something even more magical than making sperm — it can give its owners a whole lot of pleasure. Sometimes, even orgasms. Powerful, full-body orgasms. Earth-shatteringly intense orgasms.

Basically, using prostate toys, such as butt plugs, or those created specifically with prostate stimulation in mind, can make some people see God.

How do you do it? You'll need some lube, as the anus isn't self-lubricating. Then (this is a quick and dirty, pun-intended instruction); you can stimulate it by putting fingers or your prostate toy about three inches inside your butt.

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But to be perfectly honest, playing with the anus isn't for everyone. While we usually opt for Never Have I Evers that have a happy ending, not all of them do. Because sex, like life, is sometimes complicated!

This time around we spoke to Wolfgang White, a 31-year-old Canadian actor and adult content creator known for his solo male roleplay porn, about his first time using a prostate toy, and while it felt nice, his story is a little more complicated than a Happily Ever After.

Keep reading to see what we mean.

AskMen: What is your experience with prostate play?

Wolfgang White: My butthole and prostate are currently not in practice. But I spent a good amount of 2022 trying.

When was your first time using a prostate toy?

The first time I tried was around 2018 or so after having seen and fallen in love with pegging porn. I bought the smallest toy I could find, and after frantically trying to relax and make myself comfortable, I was finally able to slide it in.

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Did you use lube? Any newbie mistakes?

I did my homework and used copious amounts of lube, and I have to admit, while I wasn't exactly comfortable yet with prostate play when it finally slid it, the feeling was nice.

I probably kept it for 10-15 minutes or so, and my newbie mistake is freaking out about removing it.

And how was it? Did you like it? Loathe it?

I remember feeling like it was... too difficult to remove. Like the stopper was there for a reason and that my buttplug was now just a part of my butt forever.

Obviously, that would not work for my body long-term, so I did eventually try to remove it, and (here comes the potentially gross part), when I did finally remove it, I saw why this isn't something you can just do willy-nilly without proper prep.

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Some people don't care about little accidents... I am not one of those people. Little gifts left on the buttplug take me out of the sexy mindset, and unfortunately since I still drink tons of coffee and energy drinks, I have since left prostate play on the table.

What is your advice for newbies to prostate toys?

My advice to newbies to prostate toys: research your prep/cleaning routine (google ‘bottoming cleaning routine’), start slowly (first a finger, then a small buttplug, play around with it, then maybe a small dildo, etc), use tons of lube, try to relax.

There were a few sessions where I was engaging in decent prostate/anal play (including getting pegged), and I can honestly say they were fantastic sessions. There is a whole world of erogenous zones, and there is power in letting go; the pleasure potential is enormous.

I found that I have a submissive side, and that sub [in me] definitely enjoyed getting pegged, but what I enjoyed even more was the release of control and power, which was so freeing! Sexuality is fluid, and you should explore it safely.

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