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TOP 30 OF 2018 - 14. What was your first time really like?

First published on Sunday the 25th of March, 2018, this piece comes in at number 14 in the top 30 most read Villainesse stories of 2018.

The first time gets a lot of sensationalised press. The mixture of expectation and anxiety make it an experience like no other. Whatever happens, you’re bound to remember it for the rest of your life.

But is all that pressure really helpful? Maybe if we talked about it openly, it wouldn’t be such a loaded (pun not intended. Mind out of the gutter, thanks) experience.

I asked five friends about the first time they had sex. To be honest, I expected five similar stories. Nope. The first time is unique for everyone. The main takeaway: it’s not what you expect.

(Names have been changed.)


My expectations for my first time weren’t high, and thank God. I have endometriosis, which doesn’t mesh well with penetrative sex, so that kept my expectations realistic.  I was primed for it to hurt like a bitch and (spoiler alert) it really, really did. If I’d expected the most magical night of my life I would’ve been pretty disappointed.

After a few months of dating, my then-boyfriend and I talked and decided we were ready to have sex. Later that week we did, in my childhood bunk beds. The whole thing probably lasted less than ten minutes and no mind-blowing orgasms were had (no orgasms at all). Afterwards, I caught his eye in the mirror while brushing our teeth and we cracked up because wow we just had sex and wow it was shit.

Despite the actual sex being mediocre, I view the whole thing positively because it was with someone I loved, it was consensual, and we were safe. This was the first and last time I had sex with that boyfriend. He moved away to uni and is now happily dating men, so hopefully he’s also having better sex…


My first time was not the best night of my life, but it was relaxed and we were comfortable with each other. If I could change something, I think I would have invested in lube.

He was my boyfriend of three weeks. Prior to that we had been hooking up on and off for about six months. The night started with a bit of foreplay, which is always a good idea. I was prepared for sex, and grabbed a condom out of the hand-knitted pouch a friend had made for me. I’m much taller than him, so we struggled to find a position that worked in terms of height. Eventually, I ended up on top.

When we finished, I moved off, and the condom was gone. His first words were “Where did it go?”. Then he freaked out and started apologising. We found the condom, but I had to get the emergency contraceptive pill – not exactly the ending I expected.


It was my first year of uni. His best mate was dating a friend, and we started chatting at the rugby. I felt like everyone else was having sex and I thought, I’ve just gotta get rid of it. He started buying me drinks at a bar, and we kept chatting. Everyone was going to town, but I wasn’t 18 yet, so I suggested he come back to my room… And he did. I don’t really remember how it started (there was a bit of alcohol involved) but then it was happening, and I was like “this isn’t bad”. It felt like a natural progression. We had sex three times that night, which was impressive stamina from him.

The flat he was supposed to be staying at that night had been set on fire, so I like to think I saved him from a house fire.


For both of us, it was our first relationship and everything was new. We decided to do it on our first anniversary, in the last year of high school. He’d managed to send his family out of the house so we could guarantee time alone by telling them he wanted to cook me a romantic dinner (his mum totally knew something was up). It was the first time we could properly remove clothing, because we were completely alone, with no worries about family members walking in. We chose the spare room because it had a double bed.

The sex was classic missionary position. It hurt a tiny bit at the start, so I asked him to slow down and then it was actually really nice. He started crying afterwards because he was worried I hadn’t enjoyed it. And he didn’t finish. Later, he told me that he had been so scared about not lasting that he masturbated a few hours before.

Sex has definitely improved since then, but we were totally relaxed and just enjoyed each other’s company. It felt like a very natural thing to do.


I used to think it was such a big deal to lose my virginity to the right person. The whole idea of sex worried and scared me. But there was a guy (my now-boyfriend) who I thought wouldn’t like it if I was inexperienced. That kinda motivated me to sleep with someone.

The guy was someone I knew well and I was attracted to him. We had been in a stage show all summer as a couple, so I spent a lot of time pretending to be his girlfriend. I knew we wouldn’t end up dating, but I was happy to have sex with him.

I went over to his house after a music event. We had planned to drink together for a week and I think we both knew we would have sex. We hung out, drinking and playing games until we were both pretty drunk. I don’t remember all the details, but I was surprised it didn’t hurt at all. We tried a few positions and it was fun. I felt relaxed because I knew and trusted him.

Sometimes I wish I didn’t feel like it was necessary to prepare myself for someone else. My boyfriend didn’t mind that I had no idea what I was doing at first (although I thought one time would help me, it really didn’t). People like you for who you are, not for your sexual encounters. Whether you’ve had a lot of sex, or no sex, just make sure you’re doing what feels right for you.


  • Sex /
  • The First Time /
  • Virginity /
  • Interview /
  • The REAL Sex Talk /
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