I’ve been curious for a while about anal play while I’m pleasuring myself. I’ve heard it generates a more intense orgasm. I can take fingers, but I’d like to try something more (on the smaller side of course). Being a guy, is there a position or toy that will give me the best penetration while pleasuring myself? I’ve never reached out to anyone regarding this before. Being a straight guy, there’s not too many people you trust with whom you can mention something like this.

Your question reflects the classic conflict between pleasure and shame we’ve all been socially force-fed. You’re right! Prostate play — reached by going in and up the ol’ backdoor — can lead to more intense orgasms.

You’re also right that identifying as a straight man limits who you can talk to about receiving anal pleasure. Seems weird, as straight men are so easily socialized to talk about their penises. Though straight men have been granted permission to seek sexual pleasure, alright, it’s only certain kinds. The prostate’s location really rips up that permission slip.

As you’ve discovered, the prostate is reached easiest with a curved shape — whether hands or toys — and pressure applied to the inner wall of the rectum. That’s right, up your butt! Charlie Glickman, co-author of the exceptional The Ultimate Guide to Prostate Play, describes what you’re looking for as “a plum half-buried in the sand.” Once found, use a press-and-drag motion to massage it.

Reported reactions to prostate stimulation include longer, more intense orgasms with aftershocks, stronger ejaculations, and all around sexual sparklers. Sounds pretty nice, yet many straight men can’t get past their fears — or sphincters.

We all receive messages about who we’re supposed to be in the sack. Straight men are taught to be the controlling, sexual do-ers. So, to be a man who is being penetrated — and enjoying it! — is shamed so hard that your very masculinity is at stake. Only women and gay men get penetrated, right?

I say we all practice separating how we fuck from who we are.

You can love prostate play and still be the straightest, most rugged Marlboro man ever. You can stick toys up your butt all day and still be happily married to your wife. You can even enjoy anal pleasure and be a homophobe if you really want to, but I don’t recommend it. Being secure in your masculinity means speaking openly about what you want sexually even when that thing is something in your booty.

Now that we’re feeling secure in our straight, masculine identity, let’s get in there!

Using anal plugs will make enjoying prostate stimulation along with your masturbation ritual a lot easier. I highly recommend the Aneros plugs, which were originally designed by doctors to stimulate the prostate for cancer-reduction reasons. Now they’re the best selling prostate massagers on the market. They’re ergonomically designed to rock into the prostate hands-free while you whack it or penetrate a partner and are made of non-porous silicone-coated plastic so they’re easy to clean. Many models are svelte enough for beginners.

Whichever anal plug you choose, stick to a curved shape, non-porous materials like silicone. Angle the toy with the curve pointing towards your belly button and please make sure the toy has a flared base — this prevents the toy from getting “lost” in there. And use a lot of lube. My fav is Sliquid Sassy.

It can be helpful to use a mirror when inserting a toy for the first time so you can see where you’re going. Laying on your back and tucking your knees to your chest can help make your booty more accessible, or get into yoga’s “child pose” and reach around. Once an anal plug is inserted, you can be in any position you’d like; the toy will stay put and stimulate the prostate for you. How’s that for sexual freedom, CC? Enjoy it!•

Yana Tallon-Hicks is a pleasure-positive sex educator and writer living in the Pioneer Valley. She has a website bursting with sex advice, workshops, and resources at yanatallonhicks.com.