The Day I Lost My Virginity
A happy ending to a never-ending story.
“Jenkins, Randy!”
A nurse in blue scrubs is screaming names from a clipboard by the reception desk.
The guy sitting next to me rises at the nurse’s call. He’s wearing a tracksuit and some worn-out sneakers, but he looks like he couldn’t run a mile for his life. When he stands up, I notice a muddy-looking stain right in the center of his seat that I’m not sure was there when he arrived.
I look around me and the crowd is a sight from hell. It shouldn’t surprise me—the place had terrible reviews on Yelp — but this was the closest one to my office and I didn’t want to skip too much work.
I’m idling away, scrolling through my phone when the nurse finally calls my name. I follow her nervously into the doctor’s tiny office. There, I tell him that my penis has been hurting when I pee for the past four days, and that I have indeed had unprotected sex in the past month.
For the next stage of this ordeal I’m given a little cup and instructed to go into the restroom, where I proceed to carefully, very carefully pee into the cup and nothing but the cup. Then I step out to find the nurse again and I hand her my yellow cup of piss.
They let me know that the results will be ready in three to five days. With nothing left for me to do, I exit that place with a mix of relief and burning anticipation.
Five days before stepping into that STD clinic, I was a virgin.
At least I think I was. Honestly, my sex life had gotten off to such a rough start that I didn’t even know what the hell I was anymore.
For a long time, the day when I would lose my virginity had seemed hopelessly distant. I spent all those years building crazy high expectations around it and an addiction to porn that completely distorted my idea of sex.
So when I finally started dating, I slammed into a blend of performance anxiety and porn-induced erectile dysfunction that seemed impossible to overcome. I tried, but working on it while casually dating was tough because, understandably, none of the girls was willing to stick around and wait for me to get better.
At this point in the story, I was 25 and I had five handjobs, four blowjobs, and one in-and-out failed penetration under my belt, but not a single full-fledged hookup yet.
What I did have this time though was something I had never had before: a girl I truly liked.
I met this girl on Tinder, of all places.
Tinder up until then had been a mixed blessing. As a socially anxious person I was definitely indebted to it, because it made dating possible when I didn’t have the guts to approach girls in real life. On the other hand, using it as a guy was exhausting and the results, more often than not, had been pretty underwhelming.
By the time I matched with this girl I was ready to uninstall the app. Good thing I stuck around. After a long chain of awful dates — forcing my way through disappointing looks and empty conversations — this one felt like such a breath of fresh air.
The chemistry was there from the beginning. We joked around, we had a little cutesy moment drawing together, and over time our conversation went deep in a way that felt perfectly natural. The world didn’t go into slo-mo and lovebirds didn’t suddenly flutter overhead, but it was without a doubt the best first date I’ve ever had. Nothing more happened that night, and it was probably for the best — a soft penis would have ruined the date but postponing sex kept it perfect.
I got my first chance with her not long afterward, towards the end of our second date. She invited me over to her place, and I remember going into her room a nervous wreck. That didn’t help, of course… but wouldn’t you feel daunted as well if all you’d had so far were terrible sexual experiences? I certainly did, so it was no surprise when, come the moment of truth, my erection turned out to be “dysfunctional” once again.
What surprised me this time, however, was the girl’s reaction: it was warm and comforting. Not only was she genuinely chill about it, but she made sure that I wasn’t too hung up on it either, and thanks to that we were able to have a great time despite the circumstances.
I couldn’t lose my virginity that night, but I remember leaving her place with a certain feeling of accomplishment, and the conviction that the long-awaited day was finally around the corner.
A few days later I found myself back in her bedroom, but the feeling this time was different.
The girl lived in an art collective house with ten other people. Her room was at the end of this narrow hallway cramped with psychedelic paintings and creepy sculptures made by the other tenants. She had inherited the room from a local wood artist, who had left behind this massive loft bed so tall it left only a couple of inches of separation between the mattress and the ceiling. To this she had added her personal touches: a few dried florals, some of her paintings on the wall, a crimson-shaded lamp.
Lying on that bed with her, sheltered way up high, shrouded by warm red ambient light, the smell of flowers and paints infusing the air… I felt safe.
Unlike my own bedroom — and a handful of others in the city — this was a space free of negative associations. Sure, our first night hadn’t been what you would call a major success, but together we had turned it into a happy memory nonetheless. So coming back to it, I wasn’t haunted by flashbacks of flaccid penises and heart palpitations — I was reminded of the great time we had and I was excited to give it another try.
This shift in mindset turned out to be differential. Everything flowed much more naturally that second night. Of course I could still feel the pressure, and I still got nervous when things began to escalate, but for once in my head the positive outweighed the negative.
Twenty minutes into our foreplay, the miracle took place.
Lying on top of me, she rubbed against my body until my erection grew hard enough, then reached for it unannounced. At first I wasn’t even sure it was in, but as she started to ride it up and down it became clear that I was, indeed, having sex. I tried not to think too much about it because I wanted to enjoy the moment, and for the most part I did.
Not for long — three minutes later I ejaculated on my stomach after pulling out — but I did.
When I woke up the next morning, I wasn’t a virgin anymore.
You would think I’d be euphoric. I wasn’t. I would describe the feeling more like a numb relief. I had anticipated that day for so long and cleared so many hurdles to get there that I wasn’t really sure how to take it.
“I guess that was it,” I remember thinking, almost in disbelief.
Yet even if it didn’t feel that way, losing my virginity was a massive weight off my shoulders.
It’s hard to overestimate how big of a deal being a virgin had been for me all those years. The profound shame, the inferiority complex, the constant lies (always trying to hide it from everybody else, even when nobody else but me really cared). My virginity felt like a cancer that metastasized more and more with each passing year.
Losing it didn’t fix everything like magic, but it certainly unlocked something. At long last, I had a sex life. It was official. Now I could focus on my next goal: to make it a good one.
That journey, as it turns out, would end up being almost as long and full of obstacles, but just like the one that led me to the day in this story, it was well worth it.
A few days later, I was asked to return to the clinic for the results. They all came back negative, thank God. That itch I was feeling was likely from a tiny wound caused by friction during sex, and it went away shortly after.
That bitch didn’t give me an STD, I was just a dork who overreacted.
Six years later, that bitch and this dork are still together… and smashing has never been more fun!
What’s in your math folder?
Have you lost your virginity yet?
If so, how was your experience? If not, what are your expectations around that day?
Teenagers often face a lot of social pressure growing up to lose their virginity. Many use porn to deal with that pressure, but developing an addiction to it only pushes that day further and sets you up for failure once the day comes.
No matter your situation — whether you are trying to make your current sexually active days better or getting ready for your first — fixing your porn habits is a step that I wholeheartedly recommend.
Share your insights in the comments below, on social media, or in your favorite porn addiction community, and if you know others that are struggling with porn, help them by sharing a link to this story.
Let’s start a conversation!
Hi, this is James! Thank you for reading!
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