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Photo: Patrick Mark

Being told to “relax” very rarely leads to actual relaxation.

This is almost always the case when a passenger tells a frustrated driver to let go of road rage, and also accurately describes what happened when one woman tried to get a finger into her reluctant boyfriend’s butt during sex.

What makes the later scenario a bit unique, though, are the barriers this man — Zachary — had keeping him from enjoying a little back-door stimulation.

Related: Straight Man Upset His Girlfriend Won’t Explore His Back Door, Seeks Help From Others

For Zach, it was never a “macho” thing — after all, as he writes in a recent Esquire piece, he’s bisexual.

No, his was a purely physical limitation based on one bad experience.

He writes:

I’m a bisexual man, and I had bottomed once before with a man. We’d been dating for months at the time, and he was typically the bottom, but since I really liked him, I thought I’d return the favor. It was an all-around mediocre experience: I was too drunk, it hurt, I thought I had to pee, and I kept asking if I was pooping on him. He finally snapped, “Zach, if you shit, you shit. Shit happens.” (Pun fully intended.)

Even though I was typically a top, men I’d dated had always asked me — actually more like begged me — to bottom. After that one not-great experience, I always declined. I had too many fears, pain being the main one. I figured it wasn’t for me.

But that all changed when Zach’s girlfriend starting probing the topic, telling him how turned on she was by the idea of topping him.

Knowing that millions of men praise the ecstatic pleasure of penetration, he was wise to realize that perhaps he just needed to find a way to open up to the idea.

After experimenting a bit in the shower on his own, he was ready to try again:

After multiple attempts in different positions, I finally managed to relax enough for her to get her middle finger inside me. I laid with my back on the bed, legs bent, and it started to feel … nice. Like a massage, except on the inside of my body. I relaxed enough for her to slip her index finger in there too, and that’s when it started to feel really good. We kept it slow and shallow the first few times. After that, we started experimenting with toys and figured out what felt best for me. Thin, long, medium-speed, and vibrating — in case you were wondering. I would orgasm almost instantaneously when she entered me. I began to have orgasms that spread through my entire body like a pulsing electric shock, instead of simple orgasms localized to my junk.

I finally understood what all the fuss was about. I fully believed the hype.


Soon Zachary realized that deep down, he’s a “vocal bottom,” and the newfound sexual freedom opened up avenues to personal pleasure and expression he’d never known were even there.

He reflects on these lessons by taking a step back:

Bottoming, now, has become something that is not only important to my sex life, but important to my well-being. It’s made me a better lover and a better boyfriend to women. Not only am I more aware of physical mechanics (I guarantee that your boyfriend will never power drill you again after you’ve penetrated him), but I feel more connected to the women I’m intimate with.

And sometimes, after I’ve had a rough day at work, I just want to get plowed by a hot woman. What can I say? A man’s got his needs.

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