4 Cringe-Worthy Stories About Losing Your Virginity (And 2 That Are Surprisingly Sweet)

These IRL stories are guaranteed to make you laugh, Kim K cry and *maybe* say “awww”

Katherine Singh
An illustration of two cherries against a blue background
(Illustration: Joel Louzado)

Ahh your first time.  All rainbows and butterflies, birds chirping and soft lighting. Finally doing the deed with the one you love in a hotel in Amsterdam, after a day spent soaking in the sights and a romantic dinner at a five star restaurant. Oh wait, that’s the plot to The Fault in Our Stars.

The truth is, your first time might not have been as lovey-dovey as TFIOS Hazel’s or as epic as Game of Thrones Arya Stark’s.

More likely it was awkward AF, uncomfortable and *anything* but picture perfect. Maybe you had a poetic moment of reflection post-coital, maybe you tried to Carmen Sandiego it and travelled to another city, maybe you lost it above a seafood restaurant and can never eat fish and chips the same way again, or maybe it was actually really freakin’ lovely. To each their own, and you know what? That’s totally OK. Everyone’s first time looks and feels different. (Except 50 Shades of Grey. No, E.L. James, no one’s first time looks like *that*.)

However your first time went—the good, the bad and the ugly—it’s yours. And that’s pretty cool. Here, friends of FLARE share their cringe-worthy tales of losing their virginity, alongside some *actually* super sweet ones. Read it and weep, or just reminisce.

The so-bad-they’re-good stories about losing your virginity…

The one with the bed sheets

“It was in the spring, during the day, with my then-boyfriend. After a miscommunication with getting it in (the whole ‘I’m in,’ ‘Really?!’ thing), we only lasted about 10 minutes because it hurt so much.  When I was getting off the bed he realized that I had bled onto his sheets, which made me pretty emotional and embarrassed. He lived with his family and they weren’t home so he quickly took off the sheets and went to hand wash them because he didn’t know how to use his own washing machine (ha ha).  Then he hung up the bedsheets outside in his backyard because he said they’d dry faster.

I remember standing in the living room, staring out into the backyard as the white bedsheets lightly blew in the wind and thinking: ‘Man, should I take a picture of that?’ Like, this is my ‘virginity’ moment, white bed sheets hanging on a dryer line and blowing in the wind. After he took the bedsheets off and into the dryer, we decided to go eat something and he asked me, ‘So…is there anything you want me to say? Any three words?’ I don’t know what the hell he was thinking, but to ease the awkwardness I blurted out: ‘I want cheesecake.'”Maiesha (they/them)

The one that included travel

“My first time was with my high school boyfriend, who was two years older than me, when I was 16 or 17. We’d been dating for about a year at this point, and it was also his first time. We were both scared shitless. We’d basically done everything except ‘P-in-V’ sex at this point, and decided that in order to make sure we didn’t run the risk of either of our parents walking in on us, we’d do it in a hotel; preferably the cheapest we could find that didn’t need a credit card payment, far away from both of our homes and wasn’t overrun with roaches.

(Photo: Giphy)

Unfortunately, this meant we had to drive *all* the way out to Brampton, since cheap hotels that aren’t terrifying aren’t in vast supply in Toronto. When we finally pulled up to the hotel, I was so nervous that my parents would somehow find out about my pre-marital teenage sex—I had very strict Italian parents—that I couldn’t stop crying, so we decided to try again another time. A few weeks later, I finally felt confident enough to give it the old college try. We drove back out an hour and a half to the same hotel, paid (I’m sure the hotel staff knew exactly what we were about to do), and nervously got down to business. It was very awkward but not entirely unsatisfying.

But, about four months later, when we were a little more confident and comfortable with sex, my hymen finally tore and we realized we hadn’t been engaging in any actual penetration—my poor boyfriend was so worried about hurting me that he’d only been putting the tip in for months.”—Laura (She/Her)

The one straight out of “Work from Home

“I was freshly 19 at the time and was *officially* legal drinking age in British Columbia. So naturally,  a few of my girlfriends and I found ourselves at the local watering hole on a Saturday night in the summer. I was definitely feeling the double vodka crans I was downing, but I wasn’t overly drunk.

And then I meet a guy at the bar. We started talking, then a little more than talking, and then he asked me if I wanted to take this somewhere else. I’m thinking this somewhere else will be, you know, a house, so we left together. We were walking up the road and I asked him ‘Where are we going?’ to which he responded, ‘Don’t worry, I know a place…’ (Which TBH, famous last words).

Turns out this place was a construction site around the corner from the bar…

Locale aside, slightly-liquored-up, 19-year-old me just decided to go for it, and about 30 minutes later the deed was done on a work table where they kept the house’s floor plan. It wasn’t an earth-shattering, life-altering sexual experience, but I still chuckle a little whenever I think about it. And an added bonus is that whenever it’s my turn in Never Have I Ever, I most certainly get to make the room drink.”—Sierra (She/Her)

The one above the Krusty Krab

“For a long time, before I ever had sex, I thought it was something I had to do. By the summer after my first year of university, most of my female friends had done the deed, and I was in a rush to experience it, understand the hype and TBH, get it over with.

While back home for the summer, I went to a house party with high school friends. About halfway through the party I realized that I’d dropped my ID somewhere.(Why I took my ID to a house party, nobody knows.) I went out to the backyard to find it, where I bumped into a friend who I’d periodically hooked up with throughout high school. He offered to help me look for it, and we ended up walking around the neighbourhood, miraculously ending up outside of his family’s seafood restaurant.

(Photo: GIPHY)

By the time we went up upstairs (they lived in an apartment above the restaurant), I knew that this was going to happen: I was going to lose my virginity above an IRL version of the Krusty Krab. The actual sex was pretty ‘was that it?’ inducing, and afterwards, my partner in passion literally threw up beside the bed—so that was fun.

The cringiest part isn’t even the puking, but the fact that every time I’m home, I inevitably walk by the restaurant and have serious flashbacks to that night and how badly I wanted to be initiated into what I thought was womanhood. FWIW, I found my ID.”—Meghan (She/Her)

… And the über sweet ones

The actual picture-perfect first time

“I was a bit of a late bloomer in high school. It took a long time for me to grow into my own skin and I didn’t have my first kiss until I was 17. So, needless to say, I wasn’t in a huge rush to lose my virginity. I’d decided that I didn’t need to wait to be ‘in love’ or find ‘the one’ before having sex, but I wanted to have my partner care enough that I would feel comfortable staying the night and getting breakfast in the morning.

I’d started casually seeing a guy right after I graduated from university. He was funny, smart and easy-going. He had a relaxed confidence that made me feel comfortable. By the end of our third date, I knew I wanted him to be my first, but I didn’t know how to tell him I was a virgin.

During a *steamier* make-out, when hormones, tension—and other things—were rising, I told him. He took it really well. He validated my choice in waiting and respected that I wanted to do it on my own terms. I was so worried about someone rejecting me for being a virgin that it was such a comfort and a relief that he respected and embraced that side of me. He was headed out on a three-month post-grad trip to Europe and I had just started my full-time job, giving us only two days before he took off to potentially do the deed. When the day came, I was less nervous and more ready.

When it came time to have sex, my partner ended up losing his erection halfway through. He admitted that he was nervous and felt pressure being my first. While that might have been unattractive to some women, I thought it was so endearing and felt that it showed how much he cared about me and the two of us being together. Two years later, we’re still together and we’ve since gone on to have much better sex!” —Maria (She/Her)

The one that turned out to be about friendship  

“In many ways losing my virginity was a year-long process. I’d met this guy in the first month of university when he was visiting friends of mine and we really hit it off. I had a huge crush on him. In the fall of second year, I was living with five of my good friends; I was talking to my roommate one day about the fact that this guy was going to come visit, and she looked at me very knowingly and said, ‘I think you should have sex with him.’ And I said, ‘You know what, I think you’re right. I’m ready.’

(Photo: Giphy)

I thought, Yep, I’m going to do this on my own terms, on my own turf, I’m going to take control of the situation. He and I made plans to meet up at a bar, and I was really nervous and not sure how to go about it, so basically seven of my closest friends ended up acting as moral support and were there for most of the night. I just remember sitting across the table from him, during jazz night at this bar, and he winked at me—and I had the ultimate teenage butterflies.

We were all walking home and my friends strategically walked ahead of us, obviously so he and I could walk by ourselves. (This feels v. middle school and we were not in middle school.) We got close to my house and I said to him, ‘Want to see my house?’ And he said yeah, and that was a good way to make things work!

It was great. It was all fine, very nice and respectful. The next morning I came downstairs and all my roommates were very supportive and funny, and two of them, apparently, had been listening outside my door to see if they could hear anything. They couldn’t, which I was grateful for, because that would have been mortifying. But basically, all my good friends made sure that I lost my virginity. I think the thing that made my first time so positive was that I felt very in control of the situation and I felt like I was doing it at a time that made sense for me. It wasn’t like peer pressure, it was more of a gentle guiding into the night.” —Lena (She/Her)

Stories have been edited and condensed for clarity.


Think Your Ex Was Bad? Read These Terrible Dating Stories
Let’s Talk About First Times: An Alternative Look at Sexual Milestones
“I Wish I Hadn’t Lost My Virginity Before Marriage”: Millennials Talk Sex & Religion

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