Str8Curious: How to Finger Your Ass

Curious About Experience Some Backdoor Pleasure? Here’s How to Give Yourself the Finger

Str8Curious is a monthly AskMen column where out and proud lifestyle expert Joey Skladany answers burning questions from heterosexual men about sex, dating, and the LGBTQ+ community. No topic is off limits as he candidly lends advice, debunks stereotypes, and gives it to you straight — err — gay. Should you be interested in submitting a question for editorial consideration (and we will respect anonymity), feel free to ping Joey directly on Instagram or email him at [email protected]).

The Question

“I really enjoy fingering my butt. I am not ignorant enough to believe that this automatically makes me gay or even bi, but I do have quite a few questions: Would I enjoy a penis inside of me? How do I get a woman to focus on that area? What else can I do to maximize the pleasure?” – Dennis, Orlando, FL

The Answer

Good on you for exploring your body and embracing what feels pleasurable! It can take a lot of balls — err — forefingers, I suppose, to write off societal perceptions of what’s considered “normal” masturbation practices among men.

While I am tickled that you want my advice on this particular subject, I am, admittedly, not a fan of anything going up my butt due to chronic stomach issues. This doesn’t make me a top, though. In fact, I’m a self-described side and don’t really enjoy any type of anal penetration. To me, a finger also feels like someone is sticking a rusty nail up my hole. And don’t even get me started on dudes who partake in this activity without trimmed nails.

That said, I am 100% aware that the area is an erogenous zone (thank you, prostate) and why many guys may be interested in giving it extra attention. So I’ve decided to lend a bit of expertise and tackle each of your specific questions below.

Would I enjoy a penis inside of me?

Maybe! And guess what: That also doesn’t make you gay or even bi. A throbbing dick should feel a helluva lot nicer than a bony finger, even if it’s thicker and seemingly harder to take (lube was invented for a reason).

Please remind yourself that there is a big difference between enjoying anal sex and being attracted to other men. If you fall exclusively in the former category, that’s a-OK. If you crave men specifically (and not just the penis attached to them), then you may have a bit of exploring to do (also a-OK).

I hate to sound cliche, but you only get one short life on this earth. Make the most of it by not limiting your sexcapades.

How do I get a woman to focus on that area?

Sexual compatibility is a major component of any romantic relationship’s success. You’ll simply need to find someone who is open to bedroom experiences beyond missionary with the lights off.

Propose that she pay special attention to that region, but don’t be afraid to reciprocate and ask “what else can I be doing to get you off?” This will then feel like a mutual goal of achieving intense orgasms. And how fun is that? You may open her mind to things that she could be doing to her own body.

What else can I do to maximize pleasure?

Invest in toys. There are butt plugs, vibrators, dildos, etc. with your asshole’s name on it. Don’t be afraid to pop into a sex shop and ask for assistance (they’ve heard it all). Or browse more anonymously online and have these toys sent to you discreetly.

Here is one of many Reddit threads on the best toys for anal pleasure. There are also different masturbation techniques and reputable medical sites such as Healthline offer great tips, proving that backdoor action is more common than most people think.

In summation, there is absolutely nothing to be ashamed about when it comes to enhancing your butt play. It’s great that you’re asking these questions and are open to even more experiences with a partner. If the hole has always been the goal, consider that goal achieved.

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Source: AskMen