How To Lose Your Virginity

Grow up with a very loose understanding of sex. How does it work? What goes where? I mean, do I really have to do it? It seems painful and gross!

Yes, you must have sex. This you know for certain. This you’ve known since the day your family got cable. You have to do it, preferably while you’re still in high school. Going to college as a virgin can be really scary because everyone around you starts pretending to be a mature adult who’s capable of having casual sex. What’s up with that anyway? In high school, sex is the biggest deal ever but when you get to college, people start speaking a different language. “Oh yeah, we’ve just been sleeping together. It’s NBD. He just sleeps over sometimes.” Wow. Those three months between high school and college must’ve really been life altering! You just went from shaking like a leaf to not even flinching.

We all know that’s crap; we all know that people are still trembling and have strong feelings about sleeping with someone, but whatever. We’ll let college kids be college kids.

Back to the matter at hand, losing your V is a big D. This is partially society’s fault—there’s a real distance that exists between people who’ve had sex and those who haven’t—but it’s also a natural reaction for your body and mind. Make no mistake, the first time you have sex is intense. You’ll actually be shocked by how intense it is. That’s okay though. It will always be sort of intense. If it isn’t, that means you’re doing it wrong.

Lose your virginity to someone you love or maybe someone you don’t even know. Both are okay in my book. Losing it to someone you love is of course ideal but sometimes you do what you gotta do in order to feel healthy. It might kill you for a second—sleeping with someone who doesn’t mean a thing to you—but you’ll get over it and eventually get under someone else who’s special. I think a lot of people get hung up on this idea of losing it to someone you love but that can be dangerous. What if you’re 24 and have never been in love? Then you’re still a virgin and feeling worlds apart from your friends. You’re feeling undesirable and unsexy. Sometimes you need to just have that bad first time in order to have that amazing second or third time. This person is taking the pressure off of you, they’re removing the fear and making you feel like a functioning member of society. Odds are that losing your V will boost your confidence and help you land the person you actually would like to sleep with. You need to feel wanted, even if it’s by someone who’s unremarkable for just a few moments. I’m not suggesting that you should just lose your virginity to a complete random. I’m just saying that it’s not good to stuck on the enormity of it all. It will just leave you crippled with fear and that’s no fun!

Lose it on a creaky bed, in a car, on a washer and dryer. Lose it at 2:30pm, lose it at 2:30am, lose it at dusk. Lose it to someone who looks you dead in the eye, lose it to someone who turns his head whenever you express pleasure or pain. Lose it while listening to a song, lose it to dead silence. You hear only the smacking sounds of bodies running into each other (OMG, does it have to sound like that?) and the sound of some boy’s stifled moans. It will feel like the realest thing you’ve ever done. It will make you feel human, it will make you feel like an animal, it will make you feel.

Were you ready to have sex? That question always confuses me because I remember always feeling ready. How do you know you’re not ready anyway? Does someone get on top of you and your body recoils? That would make sense. I don’t think anyone is ever truly ready for sex. You just do it and wait for your mind to feel a million different things. I guess sometimes you’re not ready to feel that much.

Your first time is special. It sounds corny to say but how could it not be? SEX IS SO INSANE. The fact that we do it blows my mind on a regular basis. The first time is special because you feel like you’ve just been clued in on a giant secret. “Oh, so this is what we’re meant to do. This is what drives people to do crazy things. This is what makes people drink or buy expensive perfumes or work out: Someone’s body molding with yours. Gotcha, world!” Gotcha. TC mark

Ryan O'Connell

I'm a brat.


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  • Alina Trifan

    Oh God “What if you’re 24 and have never been in love?”
    I think I’ll end up being like Andy from 40 year old Virgin.

    • cecile

      I feel you, guuurrrlll! I feel you…

    • Lost Count

      its ok…everyone in their 20s in our generation is in the same boat. blame it on the recession and go have yerself some fun. but hey, remember to wrap it up!!

  • Anonymous

    I was in a coffee shop and clicked this page and the headline came up in giant, bold letters and the twee indie girl next to me looked over and saw it and saw me and sort of sighed and I wish it were socially acceptable to just lean over and go, “It’s just satire! IT’S SATIRE!”

    • Lake7less

       Actually it’s socially acceptable even to lean over and go “I hope it mentions a coffee shop”.

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  • Geleen Faye Gallego

    Oh. Pretty much convincing. Haha 

    I’ll go back when I feel like saying “Gotcha, world!” 

  • Billy

    I’m a straight male. I got to “the sound of some boy’s stifled moans” and then realised this website probably isn’t meant for me. Never mind.

    • cecile

      Babygurl,  it’s just Ryanspeak..

    • Anonymous

      Woah. You’re telling me this website alludes to the existence of gays?

      Yeah, totally not my thing either bro. Fuck this shit, let’s bail.

    • Guestropod

      I’m sure you’ve never stifled a moan


        more like never had a chance.

    • Lost Count

      its just as relative to a straight male as it is to a gay one. or girls. who like girls. or who like guys. you were totally into it.

  • sheherbano ahmed

    that last paragraph was perfection. <3

  • space mountain

    IM 20 and yeah

  • Lost Count

    what if during the first time the bodies smacking together did that thing where each person is just a little bit sweaty and just the right conditions trap an air bubble and then release a big farty sound?? Has anyone ever had that for their first time? Just wonderin how that played out haha

  • eff sox

    losing your virginity without your consent is the absolute worst thing possible though.

    • Lilym

      is that a thing that can happen? isn’t virginity basically a concept you get to decide for yourself?

      • Betty

        You don’t decide whether or not to lose your virginity if you’re raped.

  • Aimee Vondrak

    OMG YOU MUST LOSE YOUR VIRGINITY! LOSE IT! Jk I’m about to be 25 and still haven’t had sex. I’m pretty okay with it. Doing it (with someone who may or may not care about me?) is not worth the emotional havoc it would inevitably wreak on my psyche. It sounds like we all have our reasons though. I want mine to be because I love the person.

    • Len Yeh

      Word. My only recommendation is don’t listen to other people’s recommendations. Only you know what’s right for you, although you may be only rationalizing away what you might really want. 

      Also keep in mind that a lot of guys (I’m assuming you’re straight) won’t have the perspective to understand where you’re coming from. Not everyone means to be that way. We’re kind of stupid sometimes. Anyhow, it’s great when you really enjoy the person. Hope you get to do it the way you want. 

      • LDN

        you seem nice. i felt the need to tell you.

      • Aimee Vondrak

        I appreciate that, and based on my track record with men it’s obvious that a lot of guys DON’T have the perspective to understand. You’re fully right and it is hard to also consider their perspective, but I try to be respectful of the need they have to be filled in a relationship that ours would be devoid of. Great point :)

    • cecile

      U R MY HERO

    • Anonymous

      Just turned 25 and still haven’t lost the ‘V’ either.  I don’t know. Can’t really focus on it. I’m too busy focusing on not fucking up with everything else. I would rather have someone that likes to please a woman and is experienced but is not an asshole about it. Like good friends filling in something to do for a saturday night or something…whatever friends do(?).   I can do it again without worrying about being traumatized the second time.  I’d rather laugh off the weird sounds of body fat trying to swallow itself.       

      • Aimee Vondrak

        I like that you’re too busy to focus on it. What is that like? lol

      • Anonymous

        ahaha I don’t know maybe I’m just making up excuses to not do it.. but I do know I’ve been around too many assholes in the past few years to begin to think about trying.  

  • Leigh

    Ryan your writing has gotten so “omg look I’m gay!” lately but this came at the perfect moment in my life and is so well written. Thankyou.

    • Rayan Khayat

      This article has anything to do with being gay

  • Alex Thayer

    ryan, you’re so gay

  • Len Yeh

    Every time you say “losing your V” I think that a poor woman has lost her vagina.

    • Melvin Alvarez

      V for Vagina

  • Jana

    Amazing text. Beautifully written.

  • Rayan Khayat

    cool, but Ryan could you please write something that doesn’t have to do with sex…you’re making it almost sterile.


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  • Rachel Davies

    This is a really good post. Thanks for writing it, Ryan.

  • Guest

    i don’t remember my first time. was too drunk…

  • Kia Etienne

    i loved this. thank you Ry <3

  • guest

    I like how Ryan always tries to cater to both sexes by writing ambiguously but while reading this I couldn’t help but imagine ryan balls deep in another dudes asshole.

  • Letters to My Future Self

    Ryan! This will just go to my “Letter to my Future Self”. Im in my early 20s, graduated from college and now working and I haven’t lost it either. I think you get yourself ready when you can think of the consequences that might happen as a result (Emotional, Mental, Physical)

  • Larai

    Ha! My first time was painful and pleasurable and painful and pleasurable! Anyways, I felt a million different things indeed! Thanks, Ryan! I love your writing!

  • Garysharp89

    Havnt had my first time…hoping it’s worth the wait, and don’t really care about that “special person”. I read paragraph 5 about feeling undesirable and almost crapped my pants. I’ve spent mpmtsh in therapy trying to figure out my fear/need/hatred of sex, and you just gave me my answer. Thanks.

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