First Times: Learning on the Job

Words by Ruby Ellam
Art by Madison Marshall 

I have always been an impulsive person. I don’t do much, but what I do, I do hard and fast. The first time I went to a party, I siphoned vodka off other people without giving away that I had drunk any at all. The first time I went clubbing, I smoked an entire pack of cigarettes until 5am then went to work at 8am. So, while I was a sexually anxious twenty-year old with barely any experience past kissing, I had always expected that once I started having sex, I’d really start.  

This year, after attending an Australia Day party where I was excluded from one too many conversations, I left feeling immensely sorry for myself and decided I was going to do something regrettable with my free evening. I tried to get some weed to smoke alone and really settle into my self-pity, but that journey was a bust and I chose Tinder as a last resort to wrestle some drugs out of a dumb stranger with the promise of sex before asking them to leave. Instead, I matched with Leonardo who I, shocking myself and others, lost my virginity to that night.  

Leonardo was in a band and liked to talk about it. He also did not care that I was a virgin and took to the role like a champ, fighting for breath every time I took off a new piece of clothing as if I was the most beautiful woman he had ever seen. We had sex for the first time on my green Ikea rug, leaving a suspicious stain that I lie about now. We had sex another five times that night and once again in the morning.  

We had sex for the first time on my green Ikea rug, leaving a suspicious stain that I lie about now.

And with that, I was now sexually active! The experience was perfect, and I was going to see this boy again and continue to have great, romantic sex. Until I decided to do some, albeit premature, Facebook stalking – I understand that that might seem early, but these days it’s always good to check that the man you slept with is not a Nazi.  

He had a girlfriend.  

Whatever. Right? I shook Leonardo off, thanked him for the experience and decided to dive right into this Tinder thing. I was the most inexperienced gal on the block and I was ready to mingle. And within the following month, I had sex with four other men.  

There was Michelangelo, a boy I instantly knew I wanted to marry. He was a politically active, handsome, bisexual Aries with too many ideas about how to make the world a better place. We talked for hours and I was extremely excited for what turned out to be terrible sex.  Like, kneed him in the balls trying to get on top, faked an orgasm to stop him rummaging around, terrible. I was devastated.

Donatello was very soft-spoken and somewhat boring. He asked me to spank him, and grabbed a plastic ruler so it would hurt more. He called himself a bitch and asked permission before doing anything, but he was far more into his own fantasy than me. This was my first kinky sex and I couldn’t help but laugh when he jack-hammered into me while yelling that he was a dirty, dirty boy.

Raphael stopped to tell me he wasn’t actually attracted me. Mid blow-job. No more details needed.

However, despite the fun, there was still Al. He was also in a band (are all twenty-something men in bands?) and we had average conversation and average sex and afterwards I was somewhat satisfied with the attention but mostly excited to sleep. I understood why he had suspected we were going to have sex again, though I made no move to initiate it. But he was persistent, at one point pushing me into a wall. When I redirected into making out on the very uncomfortable, boner-killing couch, he brought condoms and lube and jumped on me quicker than expected. After pain and my polite yet adamant demands to at least reposition, I eventually asked to go back to my bed.  I laid there for a while, he came, then left immediately and unmatched with me.

Al was the poster boy for what could go wrong in my Tinder spiral. He got to leave, and I had to piece together what had happened while buying pregnancy tests and prescription sleeping pills. I encourage anyone who finds themselves in my situation to be louder and angrier than I was in that moment.  

Losing my virginity was both a life-changing and embarrassingly average experience.  It also involved a lot of ‘learning on the job’. You technically have sex for the first time, but what do you call your first sexual disappointment, first masochist, first time you should’ve fought back? First time someone insults you while their dick is in your mouth?

If you want to do what I’ve been doing, go get it! But be careful and do it for you and no one else. Impatient and horny? Get yourself a Leonardo who will make sure it’s a comfortable and fun experience. Just double check that he doesn’t have a girlfriend.  

*The names of the men have been changed to protect their privacies. And yes, they’re the names of the Teenage Mutant Ninja Turtles.

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