The 40 Boxing Virgin: Part I

My First Time

The obsession descended on me when I was twelve. It found me in my bedroom, where I watched hours and hours of it on a few VHS tapes I spun like a fishing reel watching the same people do it over and over. Certain scenes made me shiver with excitement. Eventually, I got to watch different people doing it on Showtime. HBO too. When my stepdad moved in, he brought cable television like a sort of consolation prize. We watched it together sometimes. I wanted to be good at it. I fantasized about it. So I started running at night because I was embarrassed of my “sugar titties” and the pouch of belly fat I had to stare at in the bathroom mirror. I tried to rip off my love handles once, grabbing them the way my older cousin used them against me when I was his practice dummy for the wrestling team. It was about this time that I learned how to starve as long as possible before succumbing to the mega gorge of any food I could find, but preferably kitkats and the just-invented stuffed crust pizza. I did my eating in private watching, those tapes sometimes, imagining. If only I could  transform my body I’d be ready for it, and if I did it even just once, I’d stop hating myself. Because, once I did that thing, no one would look down on me. That’s what I believed, back then. 

I turned 40 on August 3rd, 2026. My emotional outlook has evolved a tad, but the fantasies

are as strong as ever, the desire almost a desperation, and I still have not done it. Not for real. And despite all the other shit I had subjected myself to on a quest for self-vindication, I am still unsatisfied. When I turned 38 I committed to a final plan to get my body back together again, and promised myself I’d do it before I turned 43 or consider it a dead dream. Time is running out. This is the last hurrah. 

So, I did like most desperate middle-aged men and found someone on Instagram who was willing to instruct me. I was to meet them in their place of business industrial neighborhood near the train tracks skirting Sante Fe Blvd. The appointment was at 0645. That’s the morning. Three hours before that fateful meeting, I was laying awake in bed oscillating between glorious fantasies and horror shows. 

I prayed that maybe, by some miracle, I was a natural and I’d impress everyone. Maybe, finally, I’d find the place where I made sense to myself. 

I drove to the spot with my heart in my throat and opened the door to what was once a warehouse. The Pro was lounging on a worn leather sofa watching a reality TV comedy featuring Kevin Hart and Steve Erkel driving Lyft. There was another Pro there, too. And they both were conversational and welcoming as I awkwardly explained how I heard about them. I looked around waiting to be told what to do. The room’s walls were painted black and plastered with magazine clippings, posters, and other photos of men in various degrees of undress. There were trophies and helmets, too. An upright piano sat beside the bathroom. 

“Did you pay me yet?” asked my instructor. I had not. We’d save it for after. Next thing I know we were in the back of the building putting on protection. I brought my own, and my instructor scoffed at what I bought, and predicted that it wouldn't last the session. They had some I could buy. This prophecy was fulfilled in less than twenty minutes. 

After another twenty minutes I was pouring sweat, staggering, and beet-faced like a sixty year old wino choking to death on a cheap cigar that plugged his windpipe after a careless inhalation. At that moment I was looking up at my instructor, gasping and trying my best to be “good” when they asked…

“Do you find me sexually attractive?” 

KAZAAM! I was transported back in time to MCRD San Diego. There I was, in the squadbay again, the last time I had ever pushed myself so hard while huffing and sweat soaked. My drill instructor’s spit flying on face as he, like rabid dog, barked at me for me “eye-fucking” him. The memory brought a smile to my face. I wear the title Marine proudly, even though I didn’t do shit worth bragging about in my short time there. Even so, that title has carried me through some of my lowest moments in life, but it did not fulfill my quest. 

KAZINGA! 

“DO YOU FIND ME SEXUALLY ATTRACTIVE!” my instructor asked again. Not Drill Instructor Sergeant Hurst. This was the instructor facing me in this year of Our Lord, two thousand twenty-six. 

“No,” I choked out. 

“Then why are you looking me in the eyes?”

I loved it. Indeed, I am that guy who pays for the abuse. How depraved I am. You see, I was supposed to be focusing on their chest. I knew that. However, this ran contrary to other habits I’d developed. Usually, I’m doing my best not to stare at the chests of half the population. And I always look a man in the eyes when they speak to me. True to my nature, I was zigging when I should have zagged. This unfortunate disposition cost me my front teeth at sixteen years old.   

Here I was again,  mentally fucked by the counterintuitive nature of the situation, in addition to the fact my heartbeat was throbbing in my ears because I had already shot my wad during the warm up. I had also run to the toilet moments before to vomit up the water I chugged minutes before. Then I looked in their eyes again. Mistake.

“Are you sexually attracted to me!?”

In truth, the mother fucker has beautiful eyes and I wanted to say as such, because I love telling the truth in tense situations. And no, I am not gay, or bi, or pan, or the other assumptions people make about me. It's just that I’m one of those special kids who never had qualms admitting when someone is beautiful. Indeed, my instructor is one hell of a man. 

I had the privilege of fucking up in front of a former top-ranked heavyweight. Ring Magazine named him the hardest hitter in the world in 2008. He’s fought on the big stages facing no bullshit Heavyweight Champions. Wladimir Klitschko needed a savvy fight contract and bought ringside doctor to save him from what would have been a knockout in the later rounds. My instructor turned pro at 32 years old and took his last fight at 46. He used his fists to pay for his education, both a bachelors and masters degree. For all this, and the fact he overcame poverty to be a boxing champion on numerous occasions and in various organizations, I chose the man they call “Touch of Sleep” to be my instructor. You can find his name in the Colorado Sports Hall of Fame–DaVarryl J Williamson.

Coach Williamson skipped the foreplay and I was doing drills on the pads before I could explain to him who or what I was. It wouldn’t have mattered anyway. The coach was also working with another man at the same time as me. A pro can handle two at once. And we were getting the same kind of reaction most novices in bed get. He gave us correction:

“Too hard!” 

“Too high!” 

“Stop wiggling your ass!”

And when I did something halfway decent the moment passed instantly to me fucking up again because I didn’t know what punch is associated with what number Coach was calling. I’ve been whaling on a heavy bag on my front stoop for hours on a daily basis, but I never bothered to study the numbers. D-U-M-B. I deserved every pushup coach called for me to do. I truly was wasting the man’s time. 

Picture a six-foot-four former heavyweight champ (who is still in fighting shape) watching me with stunning polar-ice-emerald eyes filled with disdain as I kept slipping into a southpaw stance when I’m supposed to be fighting orthodox.

Left? Right? Yessir, I’m a regular Gomer Pyle with boxing gloves. 

Coach Williamson graded me as a ‘D-’ and made sure to clarify that “Dee! Not Bee! Dee Minus!” 

I smiled and nodded. I was as stoked about that ‘D-’ as Chris Farley running through campus at the beginning of the movie Tommy Boys. I PASSED!  When the session was finished I was so elated for even making it through the hour [or possibly shorter, I don’t know.] that I hung around the gym for another hour asking stupid questions until Coach had to leave his own gym to escape me. 

Just like my other first time, I left feeling like the biggest man in the world. I wore my custom T.O.S. handwraps, the protection that didn’t break on me, all the way home. 

And just like most Pros who have the misfortune of being the special kid's first time, I’m sure I left Coach Williamson completely underwhelmed and wondering what to eat for lunch. 

I’m not sure if I did a horrible job surviving a basic workout any boxer should be able to do, or if I did a great job surviving a workout that most disabled 40-year-old boxing virgins wouldn’t complete. 

Oh yes, I’ll keep going to see Coach Williamson for the same reason I’m some men stay married or frequent the same prostitute. Why bother embarrassing yourself with someone new?

Plus, I love all that dirty talk, Coach. I’ll come see you again as soon as I get some money, honey. 

This story has only begun.

POST SCRIPT: Fight Prediction Garcia V Benn on 9.12.26

As of this moment, on 9/7/26, I predict Conor Benn to be the victor in the Welterweight Championship at the MGM in Las Vegas. I will be there with my Princess. I believe Ryan Garcia will get exposed as being unconditioned compared to the British challenger. I believe that Garcia has triumphed over very orthodox and very conservative fighters by virtue of his own unorthodox left hook-heavy style. I like Garcia very much, but I believe Benn is going to out work him and take his best punches. I foresee a split decision in favor of Benn. It will be exciting, but Benn will win the war on the inside of Garcia's swings.