Tales of Virginities Lost: How I Lost My Virginity

These stories make me feel like my first time story was boring as all heck.
Photo – Brazzers (ZZ Lemonade: Dani Daniels)

Losing your virginity might be one of the last, great hurdles before adulthood. Everybody knows that the first time is often awkward, sort of special, and… uncomfortable, which is why so many of us invest crazy amounts of energy for heady first-time encounters. Here, thanks to a group of fatally-earnest readers, we have the unbridled truth. These first-time stories are raw, unfiltered, and—believe it or not—totally true.

Photo – Brazzers (Day With A Pornstar: Monique)


I went to a boys’ private school in the middle of nowhere. Vagina was about as rare as a f*cking Himalayan snow leopard. In fact, we were so wanting that we’d tug off daydreaming about Gerta, the Austrian lunch lady, who was not a picture of feminine sexuality. A couple times during the year, we’d have these lame dances, which—if you didn’t already have a girlfriend—was like the only opportunity to get down. In late-autumn, the first of these dances happened. Buses of other private school girls were carted in for an event that was as supervised as a visit to a North Korean supermarket.

I ended up sneaking away with this girl, Katie, eluding the numerous teachers and parents council members tasked with watching us. We snuck past the parking lot into a copse of trees where I promptly groped and kissed her. Now, unlike me, at the time, this Katie girl knew her business, which is why—almost immediately—she could tell that I was a virgin. She thought this was cute and in the midst of giving me a better hand job than I could give myself, proceeded to patronize me. In any case, she leaned over a tree and told me to screw her and pull out before finishing. It didn’t take my excitable adolescent penis long and, no, I didn’t pull out. I’d yet developed that kind of self-control. Thankfully, I didn’t get her pregnant. Not-so-thankfully, she gave me a reason to visit the clinic…

Photo – Brazzers (Study Buddies)


My first time was… messy, like, a Quentin Tarantino film, messy. I’d been dating this guy through my first two years of high school and after, like, a year and a half subsisting on finger banging and oral sex, I felt like I was ready to move things to the next level. Also a virgin, he was pretty eager to try sex, too. One night his parents were going to go to this huge gala so we had the house to ourselves. He got candles, even roses, to make things special and set the mood for us.

The minute we started, I gasped—but, like, not in a good way. It felt terrible, like I was being torn open or something, and to make things worse, there he was hunched up above me, this glazed look in his eyes, face contorted into a googly-eyed expression of pleasure. I told him to take it easy, and he relented; spasming finally with an orgasm, and slumping forward. When he removed himself from me, blood was everywhere. He started to panic, muttering something like: oh my god, what have I done. Apparently I looked really pale (surprise!), and he thought something had gone terribly wrong. I told him to relax and had to actually calm him down while the pain from my vagina shot through me.

The f*cked up thing, when he changed the bedding, he just left the bloody sheets in his parents’ laundry room, which they saw the next morning…

Photo – Brazzers (Over Easy)


Losing your virginity is like taking a Band-Aid off; it really hurts, which is why you want it done quickly as possible. For me, that’s how the whole ordeal went. It was with one of my older brother’s best friends in my bedroom after him, my brother and some others had returned from a night out partying. I knew him well, and we’d already kissed and touched before, so when he knocked on my bedroom door during the early hours of the morning, I wasn’t surprised. Besides, he was cute. When we actually got down to f*cking, it didn’t take long, which—in hindsight—was probably a good thing.

Years later, during a heated spat with my brother, he had the poor sense to mention our late-night hookup. He got off with a black eye, torn lip, and a ruined friendship.

Photo – SplitShire


I like to think that I lost my virginity twice: first, in high school, pretending to be a macho straight guy and second, during freshmen year of university, with my roommate. The first time was forgettable and awkward as hell. The second time was hot. It was a Friday night and I’d opted to stay in. He came in late from a night of partying and woke me up to an intense kiss. Like I’d been, he was late admitting to himself that he was gay. Not that night, though. It was an eye opening experience—for both of us. For the rest of the year he tried playing Mr. Straight, while I was bringing guys home all the time. He was likely jealous. And a bit envious, too.

Written by Hugh Jasse

An eloquent soul, a lover of women, fine wine, and travel. I can often be spotted aboard a skiff in Santorini, catching rays and artfully plucking at my lute.