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First Time For Everything: Deflowering A 30-Year-Old Virgin

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I’d never slept with a virgin. On our second date, Jim and I escaped from a hot and overcrowded bar and sat on a bench outside. Fueled by a few pints of Guinness and the urge to confess, Jim admitted to being a 30-year-old virgin. He’d never even had a girlfriend. After a long moment of silence, I asked him, trying to sound as non-intimidating as possible, why that was.

Jim didn’t have a concrete reason. He rattled off details about his life. He was Catholic, but didn’t go to church and definitely wasn’t saving himself. He went to an all-boys high school. He lived at home during college and grad school, though he owned an apartment now. He really didn’t know why. The desire was there; the opportunity just hadn’t presented itself.

I drew my own conclusions. Jim was shy. Awkward and nerdy. I could work with that. I didn’t unload my own virginity until I was 20. I’d had my boyfriends, my one-night stands. But I was no sex goddess.

Jim just needed an understanding woman to nurture and guide him. I was the perfect woman for the job. For once, I could feel in control. I liked the idea of being someone’s first. I wouldn’t have to worry if my body was positioned the right way, or if I was moving and making the appropriate noises to show how much I was enjoying it. I wouldn’t have to feel self-conscious about my white skin, fat rolls and slightly pregnant-looking stomach. There would be none of that with Jim. He’d just be grateful to see a woman naked. I’d deflower him and mold him into the boyfriend of my dreams. He was a blank slate, without bad habits to break.

His bar buddies (“BBs”) were glad he’d finally found someone, looking at our entwined hands with meaningful looks and slapping Jim on the back. One of them told me to “be gentle with him.”

About a month later, the deflowering happened after a late night out drinking. The blessed event unfolded as you’d imagine it would when a not-terribly-confident girl with slightly low self-esteem gives it up to an even less confident guy. He climbed on top of me, looking around like he wasn’t quite sure how he’d got there. Then he pumped up and down furiously before I could have a change of heart. As it wasn’t doing much for me, I watched his face redden and contort as though observing a science experiment.

After Jim finished, I told myself it would get better. I looked to him for his reaction, and asked him what he thought. “It was good,” he said. Then he added “thanks” as an afterthought, and fell asleep on his back.

Shortly after Jim and I did the deed, all of his BBs seemed to know about it. Comments were made to me about making a man of him. Normally, I would have been pissed at being talked about, at Jim kissing and telling about our private business. But I gave Jim a free pass. After all, this was a monumental occasion for him. Already tall and gangly, Jim seemed to suddenly pull himself up from his perpetual slouch. I told him how much I hated public displays of affection, but I still had to push him away over and over as he kept trying to devour my face in the middle of the bar.

Jim had another woman vying for his attention. The bar. He went there daily. When I managed to drag him out on a “real date,” he became restless. I wanted a real boyfriend I could talk to, order in food and cuddle with in front of the TV. The sex continued to play out the same as it had the first time. While I became more confident and aggressive in my teaching methods, hoping he would be excited to learn what made me feel good, Jim was a lazy student, happy to just coast and receive a passing grade. I’d had enough. I broke up with him.

But I wasn’t meeting anyone new. Had I given up too soon? I got lonely, which led to me flirting with Jim one night when I “ran into him” at the bar. Truthfully, I knew he’d be there. When wasn’t he? I was looking for an ego boost wherever I could find it.

One of his BBs approached me. “You shouldn’t lead him on,” he said. I waved him off, telling him I wasn’t. I reasoned that even if I was leading Jim on, I was justified. I was his first. I was supposed to be special. But Jim had acted like most of the other guys I’d known.

“You know, you weren’t even his first,” Jim’s buddy told me suddenly. “He slept with a hooker in the Dominican Republic.”

I didn’t believe him. But when I confronted Jim, he confirmed the story. “You’re lying,” I insisted. I looked at his face and realized he wasn’t. My demands to know why he lied to me were met with silence.

I felt like a beauty queen who’d been stripped of her crown.

What should have been obvious to me from the outset: a 30-year old virgin is likely one for a reason. His slate has writing on it you probably don’t want to read. And if you’re going to date a jerk, you should at least be getting some good sex out of it.

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