"I will forever remember how perfectly terrible losing my virginity was."

When my doctor found out I was 23 and a virgin, she told me I deserved a prize. ‘Oh my goodness,’ she said, ‘I have girls coming in here as young as 10 who have had sex.’ (Sorry, WHAT?)

At 23, being a virgin was not something I was proud of. I had many, many high school crushes, but no sweethearts.

I refused to let my best friend drunkenly take my first kiss on the slippery dining hall dance floor at a college party, even though it probably would have made for a better story than being peer-pressured into a drunken hook-up at a pub three years later.

I ended up seeing that guy for two months after. I’m not sure why. It never felt right. We never had sex.

At 23, I figured I had waited SO long to lose my virginity that I might as well wait for the right person. You know, someone I loved. Someone that knew me well enough to know I’d be a nervous, inexperienced wreck who would re-live and overanalyse the whole ordeal for days/weeks/months afterwards. Someone that was warm and generous and kind. Someone that loved me too.

Besides listening to my girlfriends gush about their magical sex lives, I didn’t really know what I was missing out on. I had never flown solo, and never, ever – you know – finished. They didn’t understand how I did it – or more to the point, didn’t. One of my friends even bought me a vibrator because she felt SO sorry for my pitiful sex life.

Peggy Orenstein on hookup-culture, casual sex, and our girls. Post continues after audio.

But for me, it was normal. Sure, I had DREAMS of wild sex in unimaginable positions and places, being tied up, blindfolded, hair pulled. I had days that I could barely concentrate because I was so bloody toey, but I had waited so long already… what was another few weeks/months/years to my life?

And then I found him, the right person. And I immediately regretted holding onto my virginity for so long. After four years at college, I regretted not just popping the cherry with a sleazy guy from the uni bar or my gay best friend when he offered. I felt like I could have skipped right past the awkward, I-don’t-know-what-I’m-doing and WHY-THE-HECK-AM-I-BLEEDING? and been happily banging my way through life.

I could have bypassed the Napisan aisle and gone straight for the strawberries, chocolate dipping sauce and whatever other kinky stuff people are into. I could have actually got drunk playing Never Have I Ever instead of slinking in the corner, hoping no-one noticed that my drink was still full. I could have been having amazing sex with someone I loved. STRAIGHT AWAY. Right. Now. RIGHT-THIS-VERY-SECOND.

Instead, I was left feeling guilty and anxious every time he was – you know – generous. Because he was leg-shakingly, ear-ringingly amazing. Because he clearly knew what he was doing and I did not. Because I knew I could never be THAT good in return when I didn’t have any practice. At all. Ever.

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"I knew I could never be THAT good in return when I didn’t have any practise. At all. Ever." Image: iStock.

Despite my girlfriends’ explicit advice, my own positive self-talk, his porn recommendations and the fact that I sort-of, kind-of, almost-definitely loved him, I just couldn’t do it. I couldn’t even touch The Dick. I didn’t want to let him down, so I shied away altogether. I couldn’t believe that I was 23 years old and so debilitatingly intimidated by The Dick that my boyfriend got nothing but vanilla kisses, while I lapped up all the love and attention he had to give. What sort of woman was I?

‘What happened to my slutty college days?’ I thought, ‘I should be ALL over this by now.’

Eventually the time came for the excruciating ‘virgin talk.’ I had to explain myself. It started with me joking that I was pregnant… with twins… and didn’t know who the father was (not a funny joke, by the way) and ended with apologies about being awkward and nervous and scared. It was actually more painful than virgin sex itself, but his response was beyond wonderful. ‘There’s no rush. Don’t worry about me. We’ll take all the time you need.’

It’s no surprise that I didn’t need very long at all. I had struck absolute gold and had fallen head over heels in love. There was no doubt in my mind that I was ready, and unlike the ‘virgin talk,’ the ‘I’m ready’ talk was much more exciting.

He knew. I knew. We both knew. It was time.

It was probably the worst sex of his life, maybe mine too, but it’s sex I will always remember. Not because I had an earth-shattering orgasm or because he dropped the L bomb, but because he showed me what it was like to be truly, truly loved. I won’t remember the sex for the sex, I’ll remember it for him. I’ll remember how he kissed me on the forehead and told me not to be nervous. I’ll remember how watched me through my closed eyelids and made sure he wasn’t hurting. I’ll remember how he reassured me that it would get better. We just had to practise.

I’ll remember how – in an instant – I stopped regretting my virginity. There was a reason I had waited my whole entire life and the reason was him. I am so very grateful for him and everything he did for me. I will forever remember how perfectly bad and perfectly beautiful losing my virginity to him was. And I wouldn’t change a thing.