Dear Dick: Popping the Cherry

Dear Dick,

I am 23 years old and have never been topped. I know I am a bottom and I want to lose my virginity. There have only been three people who wanted to have sex with me, and they admitted to only wanting me because they wanted to "pop my cherry"— not because they felt that I am attractive.

Am i being stupid? Should I just do it or should I wait for someone who finds me attractive?

Dear Frustrated,

No, you are not being stupid. No, you should not follow a Nike campaign and "Just do it!" And yes, you should totally wait for someone who thinks you're hot and wants your booty for all the right reasons.

You're 23. You have plenty of time to lose your big gay cherry, but you only get to lose it once. As such, you have to think about two big things:

1. It's not always the most comfortable experience. Even if you've been diddling around with toys or fingers or whatever, having a real man do it to you is a whole different physical experience. So you want a man who cares about you and is going to make it as pleasurable for you as he can.

2. There are a lot of emotions that go along with your first anal experience, and you don't want to jack that up by just giving it out willy nilly. So just like with #1, you want someone who's going to respect you and make the experience a good one.

And finally, why would you EVER have sex with someone who didn't find you attractive? That's just selling yourself short. There are tons of men in the world who will think you're hot, so don't waste that hotness on guys who don't deserve it.

He may have sexy pecs, but Dear Dick is neither a medical doctor nor a licensed psychiatrist. He is not a counselor, a reverend, or a rabbi. He has not been evaluated by the FDA, the CDC, or the BBC, and his words are not intended to diagnose or treat any condition. He has, however, been around the block more than a few times and is happy to answer your questions. Leave a comment or send him an e-mail.

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