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How have we kept this on the shelf since 2010? This should be a weekly thing. Anyways, in the spirit of all the amazing conversations Ryan O’Connell’s Special is prompting in re-evaluating our virginitylossmemories, here’s a classic: How We Lost Our Virginity. P.S. Ryan, we love you, come to Bentzen Ball.-ed.

Remember when your first friend lost their virginity? Remember how you asked them every single detail leading up to and immediately following that pivotal event like you were Clarice Starling trying to get into the mind of Hannibal Lector? Remember how you imagined it would be? And Remember how it actually was? Remember how something that happens in just 1.5 minutes can make you think that you’re suddenly part of the great human narrative?

I’ve asked some people around town to recount their loss of innocence (names changed of course). What follows are tales of triumph, defeat, embarrassment, and of indifference. They are stories you’ll surely relate to-  and as always, feel free to share your own in the comments.

After reading these virginity stories, I’m shocked at how much we’ve all learned (hopefully) in the decade or decades since we started having sex. It makes you realize that we’ll probably know that much more ten years from now (hopefully).

James, 26, musician.

After arousing our parents’ suspicions by “watching Lord of the Rings” in our respective basements twelve to fifteen times, my girlfriend and I had exhausted our safe locations for experimental, uninterrupted groping. Therefore, after a romantic dinner one brisk September evening, we alighted to the one secluded place we could think of: a soccer field by her grandmother’s house.

Our dignity was matched only by our expertise in condom placement. Somehow, during our first forty-five seconds of adult bliss, we managed to twist and rip our inaugural rubber. Fifteen minutes and 95 miles per hour in my ’89 Mazda later, we desperately ran into the local hospital. Thankfully, a doctor there took pity on us in those dark pre-Plan B days by giving us morning after pills in an unmarked pill bottle. “If anyone asks, you did not get these here,” he said, saving us from a Levi Johnston/Bristol Palin fate seven years before it would’ve been relevant. Phew!

Brent, 23, Internet Guru.

I went on a double date with my high school best friend, his girlfriend, and my brand new boyfriend, we fucked in the guest room in the basement of my parent’s house (I was on top), and then he cheated on me the next night. Fuck you, Evan.

Lulu, 25, writer.

It’s two weeks before my 18th birthday on a warm spring afternoon. I’m at my (then) straight edge hardcore boyfriend’s house- his parents gone. Being the last virgin in my circle of girlfriends, I decided that in order to avoid all the possible mental and emotional consequences of losing my virginity, I will have a “fitting session” just to make sure everything works when I decide to lose my virginity for real. I remember that I was wearing yellow underwear and that we were listening to At The Drive-In. We definitely high-fived afterward.

Jonas, 25, sound engineer.

My first “for real” sex experience was an awkward war of attrition. She was older than me and not a virgin and we’d been seeing each other for a while. She said she wanted to, but every time we’d manage to have an overnight situation she’d get a headache. Every time. Finally I asked her what the problem was, and it turned out her Dad was really, really sick and she was worried if he found out she was having sex he’d get worse and she started crying. I felt like shit. Not exactly romantic. When it finally did happen it was okay. I’m pretty sure Jimi Hendrix was playing.

Anabel, 25, student.

We were at summer camp, and climbing out of our tweens. She noticed me sitting at the docks, skipping swim class for yet another week. Because, I had whispered to my counselor, my period still hadn’t ended. She leaned down and quietly offered to teach me how to use a tampon. She smelled like CK1 and her hair neatly curled. I couldn’t muster the words to tell her my period had ended days earlier. We squeezed into a bathroom stall and she slipped her fingers into my panties. “The lake is just so cold,” I stammered. She kissed me softly and led me out of the bathroom and out into the backwoods. It was a great summer.

Sean, 28, actor.

I was 16. I went to an all-ages club in the “big city” with some high school friends. I saw this goth guy who I totally had a crush on.  He asked me if I wanted to drink a beer in his friend’s car. I was so nervous. We went to his car. After drinking a couple beers we started making out. A little later my friends came looking for me and found me me in the car with this guy. They were totally surprised. I think they suspected that I might be gay, but it wasn’t until that moment that it was out in the open. I told them I was going to stay at his house instead of driving back to our hometown. Back at his place, I remember being so excited that I finally got to give a guy head. Then we did it. I think Erasure’s Oh L’amour was playing.

Evan, 29, graphic designer.

I was 17 years-old and dating a 19 year old crust punk girl (yeah, kinda gross). She had gone on and on about how we should have sex and I was way into the idea being 17 years old. She told me over and over about how great it was and she had fucked every place and position imaginable with a previous boyfriend. I was easy to convince, and the talk of having sex on a motorcycle (I don’t think I even had my drivers license yet … or a motorcycle) sounded too sweet to pass up. We planned for a night of the week. That night arrived with condoms and we had sex. It was really gross, awkward, and bloody.

I later found out after a volcanic break-up that I was her first boyfriend and she was a virgin.

Deena, 25, policy analyst.

I can’t pinpoint for you when I lost my virginity, as it’s typically defined by penis-in-vagina (or maybe in the case of my gay brothas penis-in-anus) penetration. For us gold star dykes, selecting that moment which all movies, books and magazines tell us will be unforgettable due either to its special or terrifying nature, is almost impossible. In fact, I can remember several moments thinking “Is it now?!”

Was it the time my germaphobic first-girlfriend finally agreed to get naked with me and we both came even though there was no penetration? Was it the time she inserted one latex-gloved finger into me? Was it the time there was only skin? How bout the first time I got fucked with a dildo? What about the time I got fucked with a dildo and actually bled (I do remember that vividly and fondly, red shiny streaks on smooth blue silicon)? Maybe that was the time, you say. I say I honestly couldn’t tell you.

Reed, 28, musician.

My first time was outside, on a small hill overlooking the Potomac. I brought a picnic blanket and a book of Mad Libs to keep things light. Alcohol was not involved which made it unnecessarily awkward. I don’t remember this but apparently I asked if I was any good immediately afterward. Ten years later we are still together but the answer to this question is still unclear.

Alice, 24, production assistant.

I was 17, and I’d just met Thomas, the guy I’d had a crush on in middle school – when he was a senior.   He was 23 and studying at the Actor’s Studio.  We went to Soho for coffee and ended up buying a cheap bottle of wine and plastic cups from the liquor store next door.  We drank it under the statue of some Hungarian war hero or something – the one right by Soho – and made out.

After a while, I drove him back to his parents house (at least he was not living there – at the time).  We parked a couple of blocks away on a quiet street and made out some more.  He put the passenger seat back, I climbed on top of him and we did it.  I sort of couldn’t tell if we were actually doing it for the first few seconds, and I had a pretty serious PJ Harvey Is This It? moment.  I mean, it wasn’t even the back seat of the car!!  It was the passenger seat! Of a VW Golf!!

ROPED, 33, pariah.

I had just turned 14 and had been going steady with the same girl for 6 months, eternity in kid years. It was spring break. Her father was a very strict and religious Hindu so I could only see her during the day when he was at work. We had explored other options for a while but came to the mutual decision to have sex for exactly 5 minutes so there wouldn’t be too much pressure or pain. I rode the bus around the Beltway with condoms in my pocket that I had been storing in a drawer since an anti-AIDS rally in the fall. We went through her CD collection looking for a song that was exactly 5 minutes long. The song we settled on was ‘Would’ by Alice In Chains, from the Singles Soundtrack. She clambered on top like it was a physical challenge. We stopped exactly as the last note played. She smiled at me cheerfully: “That was nice!” No big deal. I was positive we were going to get married.

Lucia, 26, law student.

I was just about to turn 18 and I was the last of my friends to lose my virginity so I was anxious to get it over with. But I didn’t want it to be with someone I really liked- that would ruin it. So, I took a drive to the beach with the son of one of my mother’s friends. We had sex in his Mark III van. See attached photo.


Peter, 32, filmmaker.

After dancing and flirting with a girl for three straight hours at a sweltering house party, she leans into my sweaty, 17-year-old ear and whispers “I wanna fuck you tonight”.  So I lead her to my friend’s bedroom but along the way it becomes really clear that I can’t go another 30 seconds without pissing out the 10 beers in my bladder. I drop her off in the bedroom and whisper all slurry sexy “I’ll be right back”.

As soon as I unzip, the product of three hours of dancing comes wafting out of my pants: a cloud of horrible ass-and-ball funk. Panic. “Fuck! If she tries to blow me, it’s over.”I grab a bottle of Herbal Essences out of the shower, apply a dollop and start scrubbing away at my crotch. But no matter how many times I rinse my pubes in the sink the suds keep coming.

I finally give up and head back to the bedroom. Sure enough she goes straight in for a blow job and when she unzips…WHOA. The room is suddenly awash in some wild flower medley. It was exceedingly clear that I’d just scrubbed my dick for the main event, but god bless her…she still popped my cherry.

James, 28, Hill staffer.

The summer before my senior year of college, I had a girlfriend.  She was bubbly, hot and (thank God) vice-president of our campus abstinence club.  During our summer football workouts our team shared a field house with the soccer team.  If you had a late lifting program, sometimes your time in the locker room would overlap with that of a straggling soccer player.  One day, when everyone else had left, I remember a black-haired soccer player staring at me from across the group shower as we both scrubbed the grass off of our arms.  I didn’t know I gave him a look, but he shook off his lather and walked across the shower to grab my cock and shove it in his mouth.  “I have a girlfriend,” is all that I can remember saying before “Oh, my god!”

Adam, 27, salesman.

In high school I was kind of anti-social, and I didn’t really date, but I played a lot of sports. So, when I got to college I was suddenly surrounded by people who were at least as socially awkward, but also spent all their time indoors or behind their computers. Advantage: Me. Of course being super awkward in high school meant that I was a virgin and I was sure that college was the cure-all here. What I found, however, was that if I got right to the point of the act and then said, “actually, I don’t have sex with people” or something to that effect, it ran counter to people’s social/gender role expectations and resulted in hilariously awkward reactions from whomever I was with.

Fast forward 3 years and I’m still a virgin, on a progressive (a dorm room version of a bar crawl), so drunk I can barely see. We stumble into the student union/cafeteria where some DJ is playing and the crew kids start dancing. I wander up to the balcony on the second floor to watch them –where I run into a girl from my Macro econ class and we start making out. She pulls me into a conference room and we’re going at it, she says, “do you have a condom? I don’t want to get pregnant.”  I’m pretty drunk but still prepared to deliver my line about how I don’t have sex with people. But then I realize that she preempted the issue.  Drunkenly I swear off these traveling drinking games and decide that I can still claim virgin, readjusting the definition to mean sex with someone with whom I have an emotional attachment.

Olga, 23, filmmaker

The first time I had sex, it was the result of a 6 month strategy. I had fooled around with a guy from my university courses the last day of term at one of our end-of-class parties. Messing around in my dorm’s twin bed, I remembered noting “He has just the right penis size for my first time.” Never mind the fact that I thought he was gay. He was crazy about me, which is always hard to turn down.

At the start of next term, we began dating. I would close the door in his face after a goodnight kiss, insist on takings things slow, or cut our make out sessions short every time since I wanted things to go just right. Plus, I already knew he was the one I was going to have my “decent” first time with.

“Mike,” I finally asked one night, “Are you a virgin? Because I am.” He solemnly nodded. “Great!” I announced. “Let’s have sex.”

Halloween night, with both of us in our costumes, we tried to have sex. It wasn’t working well- we were tense and our lack of experience was resulting in hilarious pain. We tried everything to make our bodies work- alcohol, drugs, lubricants, Beck (Midnight Vultures), etc. I put my foot down at hallucinogens, since I wanted to remember the experience, and we agreed for one last shot.

It worked. We high five-d. I distinctly remember thinking “Wait? That’s it? That’s what all the fuss is about?” When he went to the bathroom, I pumped my fist, thinking “Damn, that was easy.” He walked in on me, naked, mid fist-pump saying, “FUCK YEAH!”

This piece originally ran in April 2010