6 Stories on losing virginities and what it taught people about sex

6 Stories on losing virginities and what it taught people about sex

SexJune 14, 2018 By Isabelle Kohn

If there's anything redeeming about the weird and often hilarious ways most of us lost our virginities, it's that, at the very least, it was a learning experience. It was something you got something out of — something other than HPV.

But whether that something was knowledge you used to improve your bedroom repertoire later in life, an experience that helped you get in touch with your sexuality, or just some random realization that has helped you sort through the waist-high river of poop that is life, there's a good chance most of you walked away with a little nugget of wisdom that inched you one step further away from total adolescent idiocy.

Twelfth Time's the Charm

THE STORY: I was young when my boyfriend and I decided to try having sex ... Before that, I'd never inserted anything up there — not a toy, not a finger, not even a tampon. Needless to say, it didn't work for at least a dozen separate attempts. It might have been my resilient hymen, but more likely it was my total and complete discomfort with anything even puncturing my untouched pussy making me impenetrably tense.

WHAT I LEARNED: I suppose I learned that you should try figuring things out on your own before offering other people the option of experimenting on you. Fool around by yourself first to get a feel for things, and then once you loosen up and feel comfortable with yourself, the experience will be better for the both of you.

-Lindsay, 26, writer

Think Outside the Penis

THE STORY: In high school, I was at a party and this girl and I started fooling around. I had a huge crush on her, but she had no idea who I was — I was not on her radar at all. I was completely mind-blown she was even in the same room as me, let alone all over me after only talking for a few minutes. I was so excited that I actually came a little when she kissed my neck, which was so surprising and raw that it somehow thrilled me more than the actual sex we ended up having. It was my first time so obviously I was overcome with sensation, but for some reason, the neck thing is what stands out and still does today.

WHAT I LEARNED: You have many more erogenous zones than you think you do. Your body is capable of more than you think it is.

-Mark, 26, set designer

Why Don't You Tell Us How You Really Feel

THE STORY: Midway through losing my virginity to my boyfriend, I got off him, told him I was bored, and if that was all we were going to do that day then he could find someone else to hang out with. I just walked out (What? I actually was bored). I figured he'd be mad at me, but when we hung out again, he told me that was the "most badass thing that ever happened to him."

Apparently, he'd liked how honest I was and "admired me" for speaking up. THEN HE ASKED WHAT HE COULD DO BETTER. I mean seriously, this kid was a champ. Did I mention he was only 17? I hope he has everything he wants in life.

WHAT I LEARNED: Most people like it when you're honest with them. They think it's endearing. It also helps them piss you off less. Saying what you need gets you what you want. That's important to remember, because not everybody knows how to say that to people.

-Selena, 28, bartender

Ask Your Doctor About Cialis

THE STORY: I count this as my virginity story because it's much funnier than my actual story, but ...

Somewhere along the path of my adolescence, I received some misinformation about sex. I was pretty confused about how it worked, let alone the gay kind I wanted to have. Meanwhile, I'd found my dad's Cialis in the medicine cabinet, watched him take them before he went on trips with my mom, and had seen my fair share of daytime TV commercials portraying various solutions to erectile dysfunction you should ask your doctor about. Since the sex ed I got in school was lacking and I didn't have a lot of other male role models at the time, I put two and two together and made a mental assessment.

Men take dick pills to get erections. You need an erection to have sex. You must need a dick pill to have sex!

I stole one of my dad's Cialises and washed it down with some of his Coor's Light; real adult. An hour later, my dick was exploding. I was so fucking horny, a real problem because I was a virgin. I vigorously tried to masturbate it away, but that only made it stronger. I was freaking out. I called my boyfriend (who my parents thought was just my friend) and begged him to come help me, more for medical reasons than for sex, but, he said he'd be over in a few hours. He was more sexually experienced than me and had anal before, so he kindly offered to put me out of my misery that way, which was really exciting until I remembered something ... I had pretty much rubbed my penis raw waiting for him to arrive. It was red and sore and angry and full of adult male dick pills. But, not wanting to be rude — and also wanting to finally lose my virginity — I tried to ease it into his ass.

HOLY SHIT IT HURT SO BAD. I got it like halfway in for about two seconds, but then had to take it out and just ice it. My poor dick had had enough. It was fucked up for days.

WHAT I LEARNED: Use lube. And stay out of your Dad's pills!

-Jake, 29, sex educator

Blame Sade

THE STORY: Above all in life, especially when I was 18, I wanted to do things the RIGHT WAY. And I was sure that there was a right way to rock it home with that special lady. And since I went to an all boys Catholic school and didn't have any lady friends at all who could tell me what the right way was, a lady who could tell me, "dude, there's no RIGHT WAY, there's just what feels good," I tried to lose my virginity the only way I knew how: from TV and movies. So the de-V night was straight out of a cheesy romance novel: I waited until Feb. 14. I got my hands on a bottle of wine and chilled it on ice in a metal bucket. I bought strawberries and melted chocolate. I littered the bed with rose petals. I bought silk boxers with hearts on them. I bought her a big stuffed allosaur with a droopy neck. I put on Sade or maybe Seal. I had my plan all set out: I was gonna start missionary, then put her on top, then go hardcore off-the-bed doggy until glorious climax. I planned to last at least 45 minutes and make her cum twice before I did. And after I had whispered all the sexy cliches I knew into her ears, and puffed up my chest and put on my hard-core sneering/smooching fucking face, I ... couldn't get it up. Not for all the noodles in China. Too anxious. Too much desire to do it the RIGHT WAY. I nearly died of embarrassment. At her school, I later learned, that allosaur with the droopy neck was called Chris — because it was droopy.

WHAT I LEARNED: From this I began to learn that there is no RIGHT WAY. When you try too hard to do things the RIGHT WAY you often psyche yourself out from doing it at all. There's too much pressure, and not enough heart. It's still something I do sometimes -- try to do things the RIGHT WAY, the TV way, the movie way, and it's not fun. But I'm learning to do it less. And when I live in a less pressured and more fluid way, I'm happier. That attempt at de-v-ing was just one of many times to teach me a lesson I'm still learning. Although nowadays, I never put on Sade. What a fucking cliche.

-Chris, 26, film editor

Three Bears and a Father

THE STORY: My virginity story was extraordinarily kinky. I was 13, but had been with my boyfriend at the time for two whole pubescent years. He was 15. We were all over at my friend's house, and we were getting drunk on some African vodka. I knew I was going to lose my virginity to this guy eventually, so when he drunkenly whispered "Let's fuck" like he had any idea what that meant, I thought about it for all of 0.0003 seconds and was like, "Yeah!"

We  behind this little curtain that's hanging up, and start fooling around, but we run into a problem: he's got drunk dick. Fifteen-year-old drunk dick. We couldn't get it in. I knew this was not ideal, because my family had newly discovered the internet and home computers, yet apparently hadn't discovered AOL's parental control feature. 

Instinctually, I knew he'd need some extra stimulation to get hard. So, I go out from behind the curtain — mostly naked — and ask my two friends if they'll make out with him to try to get him hard. Zero jealousy, just pure utility here. Like good Christian neighbors, they're happy to help. He starts making out with my one friend, who is much smaller than me. Then he makes out with my other friend, who is a bit larger than me. Finally, he turns back to me, and goes "You're right in the middle, just right!" like it's a fucking Goldilocks and the Three Bears porn.

Apparently, this really does it for him. Erection City. 

I get on top of him and put a notch on the bedpost. Halfway through, we hear my friend's dad coming up the stairs. We can't get dressed or off each other fast enough, and he ends up walking in on us frantically re-clothing and rolling around.

He's horrified, we're all horrified, and then ... we order pizza and never speak of it again.

WHAT I LEARNED: Beyond the obvious "Don't have sex behind a curtain in your friend's dad's house while he's in the other room while drunk at age 13" lesson that each and every one of us learns at some point in our youth, losing my virginity instantly spelled out to me that my sexuality was much more fluid, perverted and complex than most people's was at that time, or even is today. I instantly connected with that identity, which gave me something to go off in looking for future partners. I also learned in a microsecond that I'm not a jealous person, and I continually go back to that moment in 2003 to remind myself of that, ... something that has really come in handy as an adult — I just naturally don't put weight on my partners being attracted to other people. I'm not poly, but ... it just seems like there are more important issues at hand than jealousy. Thanks, African vodka!

-Angie, 27, front-end programmer

[originally published June 12, 2017 // cover photo Lucas Lenzi via Unsplash]