Mailbag: Should I Have Sex With My Pretty Hot Virgin Friend?

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Another week, another sexually deprived college kid wants advice from me. In today’s Mailbag, an anonymous emailer has an opportunity to have sex with a good friend of his, which he is oddly apprehensive about because she happens to be a virgin. But it’s all good because she’s ready to get her card punched, and better yet, she’s totally into having sex with our emailer for her first time. She’s also pretty hot. Sounds like a home run, right?

For some dumb reason, he’s unsure if he wants to go through with it. For an even dumber reason, he is seeking advice from a total stranger. The email is below.

I think I’m supposed to start off this email by insulting you but we’ll skip that and get straight to my question.

One of my closest friends, we’ll call her CJ for the sake of the email, is a virgin. We’ve been friends for a couple years now and she’s always been considered as “one of the guys”. She knows about every girl Ive been with and has even went out of her way to set me up with a few past slams. Thats besides the point though. CJ has recently has been obsessed with the idea of losing her virginity and I half-jokingly said “Well if you ever needed someone to get the job done, I could always be the one” Shes not smoking hot, but shes also not ugly. We’ll say that she peaks at about an 7.8, maybe pushing an 8 on her best days and filthy rich.

Well turns out, she was more than down for the idea to lose her virginity to me because she wants to get it over with. Her birthday is coming up and what better present to get her than a little bit of birthday sex.

I need your advice, do I do it or not?

I wish you could see my face right now, random guy who doesn’t know shit about life. It’s the look of pure, unbridled disgust. Dis. GUST. You bring shame to yourself, to your university, to your family, and most importantly, to me. How dare you poison my inbox with such garbage. How dare you, sir. You didn’t get enough wedgies in school, did you? You’re soft. You may be an adult by age, but you’re not a man. You’re a child. You’re a child trying to meander his way through this beautiful world without a rudder. A lost soul with a bleak future.

First of all, “CJ” seems like a real sweet girl. I don’t know how you tricked her into befriending you, but hold on to dear CJ like she’s the only friend you’ll ever have again, because, sincerely, she may be. And how are you gonna sit there and say CJ is a 7.8 at her very best, “maybe” pushing an 8? If she’s peaking at 8, she’s pretty hot, man. Think about it. A 5 is an average looking girl. A 10 is perfection. Lane Lindell, for example, is a 10. You’re telling me CJ is closer in looks to Lane Lindell than your run-of-the-mill college girl?

CJ is probably absolute fire and you don’t even comprehend the depth of the opportunity that sits before you. You don’t deserve CJ. Pass on this opportunity, please. I beg you. Pass on it for Ceej, so she doesn’t look back on her first time with crippling regret. God, I hate you. I hate your fucking guts. I wish CJ hated you, too. Hopefully CJ will read this, put the pieces together and realize she’s the CJ in your email, then unfriend your ass and spit in your face. You don’t deserve this. You don’t even deserve a penis. I loathe you. Drop out of school. Fuck you.

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Dillon Cheverere

Dillon Cheverere (@DCheverere) is the Vice President of Media for Grandex, Inc. Email:

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