The 5 Worst Things About Deflowering a Virgin


“Virgins. I love ’em. No diseases, no loose as a goose V-jay, no skank. No nothin. Just pure pleasure.”

Thus begins Larry Clark’s 1995 film Kids, in which the main character, Telly, is a cherry popping fiend. From this movie to the Virgin Mary to (most recently) Natalie Dylan, virgins have been endlessly idolized throughout history, not only as symbols of purity and innocence, but as things that are also awesome to put your d*ck in. And for some of the reasons outlined by Telly, this idolization makes a bit of sense. Sure, they don’t have diseases, and yeah, their vaginas are tight. But the ‘pleasure’ aspect of that laundry list? Hardly! F*cking virgins is way more headache than its worth and than it has EVER been made out to be. Here are the five worst things about deflowering a virgin.


1. The Bleeding

bandaid-smThe term ‘deflower’ originates from the act of breaking a girl’s hymen, or ‘flower’, which is a part of the vagina that is destroyed when it is first penetrated… Okay, YUCK! Was that enough disgusting biology talk for you? No? Well get ready, because when the cherry pops, the blood flows. Back in the day, when a virgin wife was all the rage and men used to hang bloody sheets out of their windows to publicly announce a deflowering, first-time sex bleeding was important. But now, centuries later, all a deflowering leaves you with is a bloody dong and an unnecessary trip to the dry cleaners. No thanks!


2. The Crying

crying-sm“Big deal,” you’re thinking. “As long as that sh*t’s tight, I can deal with a case of Rudolph d*ck.” Well Captain Disgusting, here’s a little thing that women face during sex that men don’t: pain. As in, when you force their vaginas to dilate by putting your penis in it, it hurts them. As life goes on, and as more sex is had, this pain becomes less intense and less enduring. Some even learn to enjoy it. However, the first time it happens, unless you’re hung like a Japanese toddler, it hurts like a motherf*cker. Consequently, unless this lucky lady has an abnormally high threshold for pain, she will cry. And unless you’re a sadist, you’ll feel weird about it.


3. The Responsibility

plant-smWomen view sex somewhat differently than men. You’ll be hard pressed to find many female porn addicts, or chicks that masturbate three times a day, or, for that matter, any girls who really love to f*ck virgin dudes. In this same way, and for the reasons outlined so far, women deal with losing their virginity far more emotionally than men. If you’re not careful with how you treat a girl during and after her first sexual encounter, you could sexually scar her for life, which is completely mean. Seriously, you’ve got a bizarre virgin fetish, but that doesn’t mean you get to be an asshole. Call her up, treat her right, and pay for her therapy/abortion if necessary.


4. The Parents

parentsEver had to shake a man’s hand, look him in the eye, smile, and the whole time have the thought “I stole your daughter’s virginity” running circles through your brain? Ever thought “Oh man, does he know? Did she tell him?! Can he read it on my face???” Post cherry popping parental interactions suck, and are also kind of unavoidable. The best way to deal with them is straight up honesty. Tell them the truth! You might get a black eye or lost a car windshield, but chances are you’ll get to avoid #5. Priceless.


5. The Exit (Breaking Up)

exit-smThis ties in a bit with #3 and #4. Unless you’re some virgin loving millionaire who can just pay to pop, chances are you’ve had to work really hard on this girl and earn her trust before you could convince her to cash in the V-card. Hope it was all worth it, because now you’ve got yourself a regular old relationship with a regular old vagina. When it comes time to move on — when your craving for another virgin becomes too strong — you’ve got the stickiest breakup of a lifetime on your hands. You deflowered her. You took that which can never be taken again. You think if you just stop calling she’ll be cool with it and move on? Dude, no. If you want a smooth breakup, the safest bet is to change towns, get a new cellphone number, delete your Facebook account and, essentially, go underground for six months to a year. Remember to keep that therapy money flowing though. You don’t want to be jerk or anything.



  1. Virgin Hater says:

    Well said, but you forgot the drama. It's all drama when it comes to virgins.

  2. Andrew - Hunter Coll says:

    I think bleeding + crying + responsibility + parents + a messy break-up *IS* the drama. No?

  3. Fleabag says:

    I kind of like the blood. Period sex is the best.

  4. s says:

    ok as a girl who lost her virginity about a year ago I'm going to have to call BS on some of this. Well, every girl is different but..

    1. No, not all girls bleed. The hymen can break easily long before intercourse ever occurs. Tampons, riding a bike, masturbation, etc. It might be painful for some but not every woman.

    2. Again with the pain.. it all depends on the woman's body and if she has done some exploring down there herself before having sex (which she should!). It also depends on how much lubrication there is. I certainly didn't cry! There wasn't any pain for me the first time but due so some mishaps with bc side affects I have experienced pain during intercourse but.. come on! Women are built to handle far worse pain than that, we aren't going to cry about it.

    3. Totally depends on the girl! My first time I wanted sex just like a guy would (not because I was "in love", it was something my body needed) I mean not all girls want to save it for "the one" but it's best to find out what they want. Yes you should go slow and be aware that this is their first time and might be nervous or embarassed. And no girls don't want virgin men…no one likes an awkward man but when girls are awkward let's face's just cute.

    4. Since I was 21 when I lost mine I don't think they would have cared but they aren't religous or anything. Anyway it's none of the parents business what their daughter does with her body if she is of age and happy with it..that's what I believe.

    5. Breakups are never easy. Chances are she's going to want to see what else is out there before you can even feel that her vagina is "old". You better hope YOU don't fall for HER cause she's not going to want to marry the only man she's ever been with.

    1. meneope says:

      I don't understand why a man would want to commit or propose to a woman he's already having sex with anyway!?!
      what nonsense, only an immature man would fall for that anyway.

    2. natashatownrow90 says:

      i agree. AND I LIKE VIRGIN BOYS …i just wanted people who dont know me to know

    3. VivEk Jindal says:

      i'm virgin

    4. max says:

      how we know about you

    5. tash says:

      i agree wit s, not meneope

    6. max says:

      that wonderful speech

  5. Juanping DelTorro says:


  6. […] Thus begins Larry Clark’s 1995 film Kids, in which the main character, Telly, is a cherry popping fiend. From this movie to the Virgin Mary to (most recently) Natalie Dylan, virgins have been endlessly idolized throughout history, not only as symbols of purity and innocence, but as things that are also awesome to put your d*ck in. And for some of the reasons outlined by Telly, this idolization makes a bit of sense. Sure, they don’t have diseases, and yeah, their vaginas are tight. But the ‘pleasure’ aspect of that laundry list? Hardly! F*cking virgins is way more headache than its worth and than it has EVER been made out to be. Here are the five worst things about deflowering a virgin. […]

  7. Anonymous says:

    […] Mokkozurtido: Las 5 peores cosas de desquintear. […]

  8. […] É tão terrível assim tirar a virgindade? […]

  9. […] The 5 Worst Things About Deflowering a Virgin […]

  10. Nm says:

    If you're the first, you won"t be the last, so, if you're in love, you're fucked

  11. Ekemezie says:

    Well,i think our sexual lives shouldnt be taken away 4rm us.loosing our virginities means giving us our rights to enjoy our sexual lives.

  12. this girl says:

    So I have some talking to do. I am a virgin. I've masturbated before and used things that resemble the length of a d*ck. I have never bled before. Also, I have (a porn site) up right now. I know a magazine wrote this but come on, if you're going to do a thing on virgins, at least get your facts right.

    1. rana illuminatus says:

      hi i’m rana 20 years old boy…here everything written is all f*cking bullsh*ts..its like prehistoric barbarian who wrote this sh*t..we should all treat grls first human…then whatever she is..yes i’m fascinated about my first time sex bt that doesn’t worth of my life n relation that i’m sharing with my gf…if u respect n love a grl it doesn’t matter she is virgin or not.nd all of those freaky sh*ts written here about loose vagina..haha i’ll suggest the f*cko writer to make his little penis bigger….take penile exercise man…

  13. Pixie09 says:

    Ok I'm a girl, I think you've got a little confused about the facts here. If the girls you've slept with cried, it wasn't because it hurt XD. Besides, my hymen didn't break during sex, doing gymnastics and other fitness activities broke it, so it's possible not to bleed first time with virgins. What about deflowering guys anyway? You left out the 5 worst things about deflowering guys. Number one being, they don't know what they're doing, there's nothing less of a turn on than a guy that doesn't know what to do with his penis when it matters.

    Lol what's with you guys anyway, you moan when you have sex with virgins cos they cry and bleed etc, and you moan when you're with women who've done it before cos they're all 'whores'.

  14. Aardvarkboy says:

    This writer is one of those guys who gives guys the bad rep of being dumb. The women who wrote in are totally dead on. I have plucked at least four flowers in my lifetime. Number one was an accident – both drunk at a party, she did not act virginal, bang bang and seriously stained sheets. I was back to the party and she was bitching to her friend that I just f*cked her and left. I did not find out until later she was a virgin or the messy sheets! Number two was a girlfriend who said she would not give it up until marriage. Well, she changed her mind! It sucked for me but was great according to her (and she still makes that claim 15 years later). She was very well lubricated but so tight I thought my d*ck was going to snap off. And she did not bleed at all. One other girlfriend I had bled every time we did it, and we did it A LOT! No discomfort for either of us and her doctor said it was OK.

  15. cslanmen says:

    I married the girl I deflowered, but wish I'd married the girl who wasn't a virgin, but who was smarter and better looking. I now owe a million+ on a McMansion that's worth $300,000 – $500,000 less than what I paid for it, we have a worthless, drug addict daughter, another daughter who's face could stop a clock, a failing business, and my 'virgin' wife is not only no longer young, but she's a nagging, whining, emotionally needy idiot who still thinks she should be able to shop at Nordstroms. I guess my siblings are having the last laugh because I cheated them out of their half of our father's business. They, at least, were forced to develop marketable skills, while the only thing I know how to do is boss people around.

    I also found out that the girl I turned my nose up at all those years ago has a daughter graduating from college soon, a happy marriage, and a successful career. Plus, she's aged gracefully and knows how to handle money. I'm sorry I ditched her during a rough time in her life. I truly didn't see the wonderful person she was underneath the troubled exterior, and I'm paying for it now. Had I married her, she'd have kept my kids on the right track and handled my finances much better than the spendthrifty cow I'm currently married to, who couldn't wait to drop the girls off at Grandma's or school so she could go to the Mall.

    Guys, listen up! Don't be the insecure man I was! I had to marry a girl only I had been with, and believe me, it was a bad idea 25 years ago, and an even worse one now. There are many facets to every person, virginity is only one of them, and shouldn't be the only criteria you use when looking for a mate. Good luck.


    Big Time Regrets

  16. Power says:

    I broke my girls virginity and i used a condom and it diddnt break bt she missed her periods. Wat could b her problem. Pls respond

  17. Truth says:

    I disagree with many of the comments here. I lost mines not too long ago and it hurt like HELL!! I bled and bled, it kept tightening up, and on top of that my partner wasn't the "perfect gentleman" if you know what I mean. I almost cried. I didnt want to have sex at all after that. And now almost half a year since then I do with my new bf but I'm nervous about the pain. Plus its hard on the woman because she wants to please her partner not frustrate him and piss him off. But I didnt have to worry about #4 and I disagree with #5 I left him with no prob.

    1. meneope says:

      This is what happen when you have sex in an unstable relationship as is often the case in Western societies. This is unfortunately the norm. This is also the reason rape is so prevalent in the West than the rest of the world, because women worldwide know how to pick a man whereas women in our democratic societies are having sex with men they barely even know and trust. Most of the time they are pressured to have sex anyway. This is a pity but it's not going to change because women have been convinced that getting married and having sex in a stable relationship at the fertile years of her life is bad and oppressive. Consequently many women will experience the same situation as you.

    2. Of course says:

      Yes the women in India agree

  18. DimplomaticV says:

    20 years old, complete virgin (and I mean nothing went up there, to be so blunt and honest so I may experience a few of these signs). I have met so many guys that would love to take it but I always feel like they just cannot handle it.. and I mean that in the fact that they are just incapable of taking full on PROS that come from the enjoyment of being with a virgin. And thanks to this article I am still curious but even more nervous to lose it just because it confirms the way many men think of this whole deal. I personally think that deflowering a virgin would be AWESOME for both the MAN and WOMAN because…

    A) I am probably going to take a mental image of your EVERYTHING (body, performance, what turns you on, and what you do to turn me on) and I will love it. I will want to work on making it even better and your style will be the only thing I know and like… therefore Complete dedication. And for you men, you will love the fact that yeah, I am std free and with all the tricks you can teach me there's no way it wont be fun for both of us. A virgin girl will most likely be curious and all yours.

    B)As for the responsibility/parents/breakup? Hmmm, well depending on age/consent and mentalities of both people it can either be a hit or miss. If I am wanting to lose it just to, well, lose it then there should be an agreement on just a purely physical relationship… As for the loyal types of people who are actually interested in more meaningful aspects of getting to know one another, BOTH sides should be able to handle responsibility and enjoy it (like adults) and there should be a nice connection between the two of them because the intimacy will take bedroom activities through the roof!

    And the whole thing about a vagina getting old… is pure bullsh*t, the only thing that can happen here is the spark dying out.. you both gotta keep the fire in the bedroom, or else your dick will get old too.. I mean is this a double standard type of deal? no, I dont think so.

    Again, this is just my opinion but I guess I am just the virgin that imagines sex to be explosive and pleasurable.

  19. Kangaroo27 says:

    As a guy who took my ex's virginity I can say it was one of the most emotionally fulfilling and stressful moments of my life.

    We were in love at the time, picked a date and a place, had it all set out but damn it was stressful, put a lot of pressure on myself to make it as perfect as I could because for a girl the first time really is incredibly important.

    As for #2 there are tears not because of the pain but because of the emotions afterwards, plus yeah, seeing a girl you deeply love in pain because of what your doing is a real turn-off, so its not completly enjoyable for a guy.

    The break up wasn't until 2 years later and were still friends so thats not an issue, and her family knew and liked me for ages before so no issue there either.

    The truly worst thing about it is the inevitability that the relationship will end, as someone said above, no girl wants to stick with one guy and not sample the rest, in the long term if you love them you WILL eventually get hurt.

    Still, this is offset by the fact that when your in love with a girl and pop her cherry, she'll want try anything and everything and lots of it for quite a long time!

    Plus, no matter what you will always be remembered and if you do it right, you always always be remembered for one of the most special nights of her life.

  • You Might Like