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The Last Days of a 40-Year-Old Virgin

How to take with you what you can't leave behind

By Stephen PhillipsPublished 2 years ago 5 min read
The Last Days of a 40-Year-Old Virgin
Photo by Sarah Cervantes on Unsplash

In the fall of 2020, after two lockdowns, a dozen quarantines, and various mask mandates throughout the city, I suddenly found myself facing an opportunity for sex. Surprisingly, I wasn't looking for one. A former co-worker of mine reached out to me on her birthday with an invitation to get together.

She was younger than me and unassumingly attractive. She was romantic; we drove to Topanga Beach to watch the sun set over the water. Afterward, we ate dinner in Venice at one of the few places that was open. When we arrived at my apartment, I invited her in from the cold.

We began moving together. Cheek to cheek, body to body. As we undressed each other, we let instinct take over and guide us toward what the pandemic had deprived us of.

But for me, as it has many times before, the dance only travelled so far. It led me to a point, to penetration, then paused and took an alternate route. Despite my age and experience, I am still a virgin in life. I have never been inside a woman that way, all the way. It is what I would come to recognize and accept: a door, as yet unopened.

By Dainis Graveris on Unsplash

I've experienced plenty of other adventures surrounding penetrative sex. The kiss of a lover. The intensity of a woman's passion. I recall the girl I fell for in high school: her hair, her scent, her curiosity. The way her skin shone while she straddled me, and how we were too scared to go further on the night her parents left us alone.

Next came London and the ensuing romance of my twenties. Myself, clinging to Christianity. My indoctrinated faith beginning to slip away. I stopped short of entering women, although I allowed the vulnerability of being naked. I experienced the pleasure of oral sex and gave it. I felt ashamed afterward. I realized I still thought sex was wrong.

I recall pornography, although I've often wished to forget it. Turning to it made me feel less guilty about sex, less prone to feeling excluded. Here was something I could learn from, watch for hours, and masturbate to. The voyeurism let me experience sex without participating, to feel its power and then release. Everyone looked happy there, their tan bodies moving in ancient synchronicity. I longed to join them, and kept part of me planted in the online world.

My habit turned addictive. Porn entered my sexuality through the wound religion left behind. I moved back home, a virgin at 29. Then, to California. I had growing up to do.

By charlesdeluvio on Unsplash

What followed was a series of events in my thirties that, even for a memory like mine, induce haziness at best. There were encounters with women, but they were stagnated and inconsistent. They simply never lasted. I fell behind like a detective without clues.

I wanted to lose my virginity, but my guilt was strong as ever. On top of that, the pornography laid hold. At 34, I developed a back injury that made it uncomfortable to have sex. This frustration led to more pornography, increased erectile dysfunction, and consistent pain. My attempts at real encounters began to dwindle. I stopped approaching women and hoped that they would somehow, magically appear.

Then, in my mid-thirties, a woman I was interested in alighted from the bed to grab a condom from the bathroom. We were in an Airbnb she was renting in Hollywood; she was thinking of moving to Los Angeles and had some time to get to know me. When she returned, my half erection was almost down to nothing, but she mounted me and attempted to cover it before it shrunk away. Staring at it, focusing in on the intricacies of my penis half covered in latex, I realized I'd seen enough. Of the way things were, at least. I had watched this film so often, I had memorized the ending.

I would be with someone and initiate sex. I would feel Christian shame and guilt embedded deep within my body. Next, a dose of erectile dysfunction as a recovering porn addict. Finally, the idea that I would injure myself because my back was already in so much pain.

We both stared at my privates, trying to calculate what was needed for resuscitation. I felt like I was half-alive and dying. I embraced her, took off the condom and went down on her like I was writing an apology.

I did the same thing to the woman in quarantine in the throes of the pandemic. I went down on her, but didn't fuck her. I remember thinking how exciting it would be to lose my virginity on her birthday.

By Dainis Graveris on Unsplash

Sometimes, I forget my penis has never entered a vagina. I forget that's a thing you can do, like hiking or learning a foreign language. I know I can do it, and have certainly tried. At some point, I stopped trying, and I know it's okay to take a break and start again.

What I try to remember is: I've already entered so much in life. Born into religion, becoming an addict as a result. Injuring myself and then discovering the emotional ties to pain. Recognizing the traumatic nature of all three, and beginning to heal. One day I will bend my spine properly. One day, my heart will be aligned from the inside out.

It's beautiful to me that I while haven't experienced one thing, I've experienced so much more in my pursuit of it. I've been chastised and had my heart broken. I've broken hearts and had the fear of God shot into me, only to dismiss it in the end. I've felt ecstasy, I've been in love. I've lain naked with my soulmate while the New Year turned over sleepily in Spain. I've jumped half-naked into a river off an Indonesian island. I've shared secrets with a lover, still wet from the river, while we made breakfast and coffee and ate wrapped in blankets like settlers on the porch while sailboats waved hello. I've lived an entire life as a virgin and earned it. I've looked fear in the face at sunrise, left and sat there waiting for it again at dusk.

I've grown into someone, over two decades, too courageous to recognize. All without being inside someone. Imagine what could happen when I do go all the way?

By Nicholas Barbaros on Unsplash

In the meantime, I'll move forward like I always do. With clarity of vision. With romance. With black coffee and a smile. My virginity is part of me, but it is not all of me. There is a depth to me which cannot be measured by sexual experience or lack thereof.

On Saturday, I'll go to the Dodgers game with friends to celebrate my own birthday. I'll be in the moment, stay there, and let the moment run its course. I'll probably think about sex when I get home, and that's a fine way to drift off. Then, I'll go to sleep and dream whatever else has been on my mind. I'll talk to myself. And try my best to listen.

I'll wake up, turn 41, and then I'll be that, too.


About the Creator

Stephen Phillips

Black coffee and late night flights. ☕️✈️✨

📧: [email protected].

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