I was terrified of bottoming before I tried it. Even though I had topped a number of guys, I was convinced that bottoming was going to be pure torture. I know it might sound absurd — given that I’d seen firsthand the immense pleasure my partners experienced from anal penetration.

I had also begun to embrace my identity as a “top.” Inherent to how I perceived this identity — though I didn’t realize it at the time — was the notion that top equates masculine. Being on top was the “manly” position. I felt empowered being the one thrusting. In this asinine way, it fed my ego. Even though I often act more feminine in my everyday life, I liked knowing that I was the “man” in bed.

And then (can I be frank here?) I’d heard horror stories from friends about accidentally “letting loose” on a guy they liked. I didn’t want to deal with any of that awkwardness, so I didn’t bottom for years, even though there were guys begging me to try. That was until I started dating this guy who mostly topped. After a few months, I decided I wanted to bottom for him. I felt like a crummy partner for not returning the favor. I also respected him for never being pushy. He asked early in the relationship if I would bottom, and when I told him I didn’t want to, he never asked again.

So I went through with it, making all the classic first-time bottoming mistakes: I didn’t “clean” prior because I had no idea how, and the whole time he was inside me, I clenched for dear life. I could not relax or loosen. I was on my stomach the entire time because for whatever reason, I thought it would be the easiest way to start out — FYI, it’s not!

I was terrified of making a “mess,” given that was the only sensation I’d previously felt come from my rear end. He kept saying, “Relax,” but I was simply too terrified to really try.

I didn’t let go, but I did decide bottoming was not for me. There were bottoms, and there were tops. Clearly, I was the latter. Besides, lying on my stomach didn’t feed into the powerful, dominant, or masculine persona I had cultivated in the boudoir.

But that all changed when I started dating Jenny.* Like me, Jenny is bisexual. But unlike me, she was a dominatrix who liked being verbally abusive to straight guys while she pegged them. Honestly, I tend to laugh when people start calling me dirty names, so at first, I had no desire to bottom for her. That shocked her. I remember her saying something like, “Honestly, I thought one of the best things about you being bi would be that you liked to bottom.”

Regardless, I loved Jenny and I would do anything for her, including taking it up my ass. I agreed to give it another try, and she told me I needed to practice on myself with fingers and toys. I realized that’s where I went wrong the first time. You have to prepare! You can’t immediately expect to take a whole penis inside you without a warmup or knowhow.

So, I cut my nails the shortest I’ve ever cut them, lubed up my index finger with conditioner, and slowly worked my way up in there while I took a shower — it was, OK-ish. In hindsight, I realized the problem with my little experiment was that I wasn’t turned on. Later, at Jenny’s place, she started fingering me while jerking me off: “Relax,” she whispered.

When I managed to stop clenching, I finally understood what all the fuss was about. It didn’t take long before I became a big ol’ bottom. From then on, we used fingers, she used her mouth, and we used toys. Oh, boy, did we use toys.

Although my relationship with Jenny didn’t last, my love of bottoming did. In the years since, I’ve bottomed for plenty of men and women. But bottoming with a woman, I’ve discovered, is not at all like bottoming with a man. It’s a whole different thing when women play with my anus: It’s kinky. It’s naughty.

Bottoming has now become something that is not only important to my sex life, but to my sense of well-being. It’s made me a better lover and a better boyfriend to men, women, and genderqueer individuals. Not only am I more aware of physical mechanics, but I feel more connected with the people I am intimate with. I’m also definitely no longer concerned with notions of “masculinity.”

In fact, being on all fours and crying for my girlfriend to plow me harder has turned me into more of man than anything else I’ve done in the past decade. *Not her real name.

ZACHARY ZANE is a regular contributor to The Advocate.