Describe the experience of losing your virginity.

Your stories ranged from the ecstatic to the traumatic, with most falling squarely in between: mild disappointment bumping up against let's-just-get-it-over-with relief. Here are some that we found particularly touching, evocative, funny or concerning.


I got drunk at a New Year’s party and faked an Australian accent to a person who had known me for years and was very much into it. We had terrible, quick sex (with another friend sleeping in the same room). This person pretended not to remember any of it for five damn years. We remained friends, and they told me the truth in a Taco Bell as we ate 7-Layer Burritos together.

I was 16, he was 19. He asked me what I wanted my first time to be like, and I described a cheesy scene right out of a Harlequin romance: rose petals on the bed, candles, champagne, etc. To his credit, he did his best to create the night I wanted, and I learned two things that are still true: 1) Champagne is gross. 2) Sex is great! 

He was French… and a massage therapist. Bliss. Best decision ever.

Lost it to an ex (he was my ex at the time) while watching The Bourne Supremacy on DVD. Will always associate it with Moby’s Extreme Ways.  

A hookup with a street performer (contortionist) in an Ottawa U dorm.

Wine and High Park.

Scary, and I lost it with a woman but was totally disgusted with women’s parts. So wanted to be with her brother.

Muppet Treasure Island was on the laptop. Me and my first boyfriend had decided to stay in for St. Patrick’s Day.

Badgered repeatedly as a teen by my 25-year-old boyfriend until he wore me down into saying yes. It was awful. I got pregnant and had an abortion. Scarred me for a long time.

My mom was downstairs. Aladdin was on TV. His mom called twice. It sucked.

To the movie Hook.

Lost my virginity to my sociopathic, rich, bratty boyfriend. He lasted a few seconds. He asked me not to touch him during the process.

He was sooo goth and we were listening to Sisters of Mercy. 

Perfect. I was 19, which seemed old at the time. It was with a guy I was going out with, and though things didn’t work out, we remained friends. When my hymen broke and there was blood everywhere, he shouted, “It’s like the Texas Chainsaw Massacre!” It wasn’t painful or anything, and the reaction made it so much more comfortable. It just felt like there was no pressure at all.

• Just the tip, just to see how it felt. With the closing credits of Fight Club playing in the background. 

Not being sure if it was in or not. Then realizing it was. I felt the same as I did before. That’s when I realized virginity is a crock of shit.

lots of blood omg

In a car outside of my friend’s house. It was bad. There was bleeding. Why a car? Afterwards, I had chicken wings and watched Empire Records with my friends. That was better.

“Is it in? I can’t tell if it’s all the way in. This really isn’t too AHHHHHH.” “…It’s in.”

It was a very unromantic night in suburban Tel Aviv with a nebbishy Toronto Jew who studied in Queens. He told me he wasn’t the man who loved me.

York U residence. Tiny bed. Tiny penis.

Whoa awkward sleepover. 

Honeymoon. Brutal. Recognized we weren’t compatible.

In the back seat of a Ford Pinto on the shores of Lake Ontario. I just thought we’d be making out a little. Turned out she had other ideas. Ever try to stretch out in the backseat of a 1978 Pinto? We had to open the door to stretch our legs out, which turned on the inside light. Which was nice because we could see each other, but so could the couple in the next car over that pulled in without our noticing. 

So much less horrible than I’d been led to believe it would be. 

Met a girl at a re-enactment fair, spent the night together in a tent, she left the next morning, and I never saw her again.

“Hmm, this is a bit weird, but I can see how people enjoy it.” 

It was quite good, to be honest, really good. I am a trans girl now, but then I was living as a gay male. I was 18 and it was my first boyfriend. I was a few months older than him. It was my first time going to his place, and he introduced me to his parents as his “friend,” but his sister knew otherwise and gave me a knowing, cheeky smile as I went into his room. We laid on his bed and put on Shortbus and got so horny from the film we started messing around, then we did it. I am a bottom and he topped me. We fucked twice in a row and, no lying, when we finished, the movie was over. He is a Scorpio, so he was good and skilled and I enjoyed it.

Camping in Elora Gorge with my high school boyfriend: reckless, unplanned, and while wearing my high school debate club T-shirt.

I was 16, drunk at a disco in Greece and lost my virginity in the middle of a farm field. Don’t remember much, only that the ground was rough.

Just after high school, boyfriend, drinks, pizza, my bedroom, less than 10 minutes. He left with his shirt on backwards and inside out. Anticlimactic.  

Losing my queer virginity was magical, floaty and surreal. We had been through some young-person drama, and I was certain our friendship was over. I always harboured romantic feelings for her while we were friends, and when I thought things were over I spilled the beans. She invited me over, and we sat next to each other in bed, being very sad and intense. There was crying and hugging, and my face was close to hers. I kissed her, and it was one of the best kisses of my life. I had never slept with a woman before, and everything felt extremely right I told her I loved her. It was both of our first times with another lady, but afterwards she asked me if I had done this before, because yeah it was that good.

Lost it to my mother’s best friend. 

She was a year older than me and SO much more experienced. I was her project. 

It was during the first Gulf War. My boyfriend used two stealth-bomber-themed condoms. We were in a basement on a waterbed in North York. We were 16 and so horny. It was the first time I felt like I was flying. 

It tasted like Grand Marnier.

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