Out of pure desperation, I bit his pillow, already littered with imprints of my despair, begging for some form of relief. I hoped that by inflicting any miniscule amount of pain on this inanimate object of comfort, I could somehow escape the penetrative force threatening to consume me from behind.

With each recurring thrust came a brand new wave of anguish, each of his loud moans matched by my own excruciating groans. All I could think about were his poor Foothill neighbors, likely balls-deep in quantum physics — or some equivalently difficult material — trying to tune out our obtrusive fucking.

But I didn’t care about their midterms, or my own impending anal doom, all I could focus on was nailing this exam for Getting Nailed 101.

It was time I mastered my own asshole and discovered the insatiable prostate rumored to reside within me. Eventually, after multiple rounds of painful trial and error, I found this elusive light at the end of my tunnel.

But getting there was by no means an easy task.

Even allowing myself to bottom in the first place was a whole psychological endeavor. To begin, I had to defeat the tri-headed beast that lurked within the dark caverns of my brain: my nagging, fragile sense of masculinity.

This pustulous monstrosity dictates whether my actions fit within the prescribed confines of my rigid gender identity. If I ever happen to step outside of its bounds, it will eat me up internally, screeching until I come back to a more normative, societally consumable existence.

My whole life I have tried to destroy this creature with multiple tiny blows. I’d wear makeup here, twirl on a pole there, but this time I wanted to give it the ultimate stab.

The Sexual Silver Bullet: Bending Over.

According to bogus sexual law created by an archaic patriarchal force with a stick up its ass, men are meant to fuck, not be fucked. This stems from the male’s need for constant control, which permeates every visible aspect of modern life. By submitting to penetration, men reconfigure to the feminized position of sexual intercourse, becoming the receiver. This is why anal is such taboo, because men shed some sense of phallic dominance and take on the “established” sexual role of women.

I knew that diversifying my sexual experiences would be one of the best routes to vanquishing the masculine beast.

The answer was clear: I must put dick up my ass.

After resolving my internal anal conflict, next came the even harder part. Actually, physically, doing it.

The only thing high school sex ed ever taught me was how to avoid impregnating a woman, a skill I’ve had since coming out of one. What I really needed to learn was how to engage in safe consensual gay sex. Without any constructive education on how to navigate preparing for anal, all I had for reference were the blueprints I acquired from gay porn, the abysmal depths of the Internet and this eager dude right behind me who I barely even knew.

But, I was determined to learn. And I did.

I made it clear that we had to start off on a baseline of communicated boundaries. I would let him top me only if he consented to my two conditions: that he go slow (for I was a gayby in the bottoming realm), and that he be liberal with the lube (without proper lubrication the penis morphs into a dehydrated pinecone hellbent on dueling with your sphincter).

With the help of some explorative fingers, icy KY jelly and steady coaching I was able to fit the whole thing in. Bottoming had initially felt like I was patient zero on the movie “Alien,” as if this tiny wormlike creature had invaded my body and would soon break through the very fabric of my being, but after learning the ins and outs of my ass: I transcended.

If it hurt too much I’d tell him; if I liked the position we were in I’d let him know. He’d hang on to my every word, as every consensual sex partner should. Our dialogue broke down my internal bottomphobia and allowed me to “open up” to new possibilities.

Through the magic of bodily exploration, I experienced pleasure and deconstructed aspects of my previously inflexible gender identity. I had boxed myself into my sole role as designated “top”, but eventually found the same old sexual routine to be bland. Why limit the pleasures of the human form? Why reject the possibility of anal stimulation?

Believe it or not, all men, regardless of sexual orientation, harbor prostates with the potential for mind blowing stimulation. The heterosexual matrix needs to start taking analplay seriously; it’s not just an exclusive form of pleasure reserved for me and my queer peers.

So boys spread ‘em and girls equip your strap-ons and get to pegging! Let’s (consensually) deconstruct heterosexual rigidity one anus at a time.

Chris Cox writes the Tuesday column on sex. Contact him at [email protected].