Deflowering a Virgin


So I received a great advice question via email the other day and I thought today would be a great day for a video post since the majority of you are not working. Oh but then again, if you’re not working I’m sure the majority of you have better things to do than watch videos, don’t you? Anyway. Here’s the question and you can see my response on the video:

Recently, I was asked by a guy I know if I would help him lose his virginity. Flattered as I am, I don’t know how to approach this situation. First of all, I didn’t know they still made male virgins at the age of 26 (he said it’s for religious reasons). Second, I’ve always been the least experienced one in the bedroom and I am usually not the girl who takes charge of things. Third, he’s not really my type of guy (too short and too skinny). However he is packing and I am intrigued by the proposition of us exploring and learning together. So my question is should I do it? And if so, what should I know about “de-flowering” a dude and how should I go about doing it?

So what do you guys think? Should she go for it? Anything she should know before she goes in? Have you ever deflowered a virgin? Tell the story in the comments.

Oh and by the way – you can find the post I mentioned in the video here. It’s fucking hilarious. And I’m not just saying that because I’m Dr. J’s biggest stan, I promise.

bag lady. digital nerd. beauty junkie. shoe whore. i'm a sucker for big words and box-fresh kicks. know a little bit about a lot of things and have something to say about everything.

Comments 12

  1. HLBB says:


    I was wondering the entire video why you didn’t talk about the packing part…and then you came back.

    Yes! That is all!

    1. I was trying to “thumbs up” this comment 12 times but kept encountering an error!!! “If you win LottoMAX, you don’t say ‘Hmmm, I wonder if I should pick up the money’. You pick up the fucking money!” I died!

      Yes. Just do it woman. I’ve never had the pleasure of deflowering anyone but man oh man, if I was given the opportunity NOW at this peak level of mine?!?! Poor guy…..

      Cash out!

  2. Tisha says:

    LMAO…Cock Lottery! Love it

    1. NinaFontaine says:

      I KNOW! Totally Co-sign

  3. Malik says:

    You don’t steer trains Max.

    Also, to the gal asking the question: No. I won’t even go into detail, just no is my definitive answer. That’s not helpful in the least. The answer is still no though.

  4. Melzie says:

    Back a few years I probably would’ve said not to cross the line. However being 40 and frisky makes winning the lottery as a benefit of helping a guy out appealing beyond measure (no pun intended, I guess) ๐Ÿ™‚

  5. Girlsixx is ChloeRayne516 says:

    She should definitely collect her prize…….. (cock lottery). *lol*

  6. Mrs. Brightside says:

    Donโ€™t do it. I accidentally deflowered a guy back in โ€˜05 and even after pledging and getting neo pu$$y, and having a kid he still sees me as this sex goddess he needs to prove himself to. A good cock is hard to waste.

  7. i think she should do it.

  8. Lund says: writes – I am a 22 yr old virgin boy smart tall handsome intelligent atheletic but shy and due to conservative Indian society I am unable to lose my virginity. Please help

  9. Lundchhunni says: writes – I am a 22 yr old virgin boy smart tall handsome intelligent atheletic but shy and due to conservative Indian society I am unable to lose my virginity. Please help ok

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