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Dear Richard: Caution! Entering Virgin Territory

By Dear Dick

Dear Richard,

I’ve just recently turned 25 years old and still have never had any experience with a guy - or girl. I'm almost positive I'm gay, and I'm not worried about getting a hook up.

What concerns me is that for my first... well, everything. I want it to be special.

Am I asking for too much here?


Special Someone Seeking Same


Dear Special,

Let’s start with a couple lighthearted jokes:

1. If you’re looking for something “special” on your first time out, there’s no question: You’re gay.

2. Are you asking for too much? Yes.

In all seriousness, what you want is magnificent, and you should be applauded for following your heart over your hormones. Most guys would just try to bust a nut and go on to the next hot twink who comes their way. You’re a romantic, and there’s nothing wrong with that.

The sad truth, however, is that first time sex rarely matches up to one’s expectations. It’s the same with any kind of fantasy, whether that be a man exploring a fetish or a younger pupcake discovering his sexuality. The other person can't possibly know exactly what's in your head so there's no way he can fulfill those secret desires.

But even guys who did have a decent first encounter often find, after more experience, that it wasn’t so wonderful after all. And they’re not just talking about the sex.

There are countless areas where the other man might misfire, no matter what his age. The guy might not know how to kiss or end up being a jerk. He could be immature, uncommunicative, self-hating, passive/aggressive, take advantage of you, or simply not like you as much as you like him—and for someone who is emotionally vulnerable that can actually be the most painful blow of all.

So the big lesson here is this: Don’t sweat it.

American culture puts a huge emphasis on having your first experience be special, and if it is special at that moment in time then rejoice. If not, don’t let it tear you down. You will have other amazing partners—hopefully many of them— and during that life journey you will meet men who blow you away. They will excite your mind, body and soul; some will nail each area separately and some will amazingly hit them all at once.

You will also meet men who are a waste of time, guys who will make you feel regret. But from those men you will learn a thing or 10, and you will be smarter moving forward, so from that perspective you’ll actually gain some value from those relationships.

The worst thing you could do is sit on the sidelines desperately searching for the perfect guy to come along. He may or may not. You have no way of knowing. So get into the game. Meet men and get to know them. See if there’s physical and emotional chemistry. Kiss him if it feels right. Hook up if it feels right. Just continue to use your head and be safe about your decisions.

You may find love, or a best friend whom you never sleep with, or a man you sleep with who becomes your best friend, or an asshole you can’t stand. That’s all a part of life. But listen to D.R. when he says this: Enjoy those moments. We rarely get these kinds of “firsts” in life, and they should always be cherished.

Dear Richard is not a medical doctor, a licensed psychiatrist, 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. The information is for educational purposes only and it not intended to serve as medical advice. Dear Richard does, however, love hearing from you and answering your questions. Leave a comment or send him an e-mail.

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