Popping Your Gay Cherry

I’m 20 and a virgin–shhhh! don’t tell my Dad he thinks I’m getting all the pussy in the world–and I’ve come close a couple of times but always chicken out at the last second. It’s not that I don’t want to do it; I love a guy pressed startingly close to me, feeling his hand run up my boxers and over my hard on; I’m just worried I won’t be good sexually. (I haven’t even given a guy a blowjob before!)

The guy who I want to pop my cherry is a few years older but he’s had a lot more experience. He’s the kind of smoking guy you look at and immediately think he could fuck you up the ass in a toilet cubicle or lockeroom or car. I don’t think I want a relationship yet, but I’m worried that the second his cock slides into my ass I’ll suddenly want him around all the time. The way it looks on Pornhub or Xvideos makes me think that could be possible.

We’ve got the house to ourselves for the weekend cause I hear sex is addicting but I just don’t want to be someone who grows clingy after sex. And do you think I should start kissing and work my way down or just launch into 69ing. He said he could rim me but I’ve never had it done? Does it hurt? 

And final note: I think your view on sex is not only healthy but amazing. I had a lot of internalised homophobia about sex, probably cause I grew up in a rough part of Australia like so many other guys, but ever since I started reading your Advocate pieces I started to see that I didn’t have to be ashamed of wanting to be fucked in the ass, of wanting a guy to blow over my face. And that sex is nothing to be ashamed of but enjoyed. Thanks for helping disassemble that for me and so many guys.

Keep up the good work.

 

It blows my mind that I’m being read in Australia. You, young sir, are on the cusp of your adult sex life, and that’s exciting. I can tell you’re excited. I’ll start with the first questions and work my way down.

In the beginning, you won’t be great at sex. No one is. You will only improve with practice and experience. If you’re sexually adventurous and ready to have a lot of sex, you might learn quickly. But be warned: Lots of sex also means lots of letdowns, mistakes, lackluster hookups, STI risk, and emotional hurt you will have to navigate. Sex is more than mechanics and penetration. It’s emotional, and when you’re new to it, emotions will get messy.

Also, forget what you see in porn. I work in porn. Porn isn’t real. I see the messes and mistakes that get edited out. Your first attempts will be nothing like porn and if you compare them to porn, you’ll think you’re lacking or doing something wrong.

You’re not lacking. You’re not doing anything wrong. You’re just not a porn star. And no one can fuck like porn stars — not even porn stars. Again, porn is fantasy. Lackluster performances look great with a little editing.

Real sex is both better and worse than anything you’ll see in porn. The more you do it, the less you will relate to porn. Porn may be intense for you now, but someday you’ll have intense sexual experiences that happened to you — a memory bank of great sex that is yours, in which you were the star — and porn will likely lose its luster.

No, you don’t want a relationship right now. And yes, you will get clingy after sex, at least in the beginning. Most of us do. I did. Sex is a powerful experience. When we’re new, we tend to latch onto those we share sex with, not realizing the fault in doing so. I’d tell you not to do this, but that’s like telling you not to breathe. You will, and doing so will teach you valuable lessons.

You’ll get heartbroken. You’ll get jealous. You’ll probably hurt someone. Clinginess comes as quickly as it goes. You’ll meet another guy, you’ll get bored. You’ll cling from guy to guy till you can stand on your own feet. These first guys are your footing into a new world. They’re not meant to stay. Even this current older gentleman will be a brief stepping stone on your way to selfhood.

Start kissing and don’t worry about what to do next. Just do what feels good, and let him lead. Who suggested that 69ing is an obvious next step from kissing? It’s not. Mutual oral (69ing) is much harder than it looks in porn and is not very pleasant. It’s a dumb position made for porn, not for reality. And no, rimming doesn’t hurt. It is god’s sweet gift to gay men. You will be blessed.

Unlike porn, your first sexual attempts will be over-eager, awkward, and probably unrewarding. You might make a mess. You will probably have feelings of doubt. You will probably have complicated feelings that you can’t fully describe. All that is normal.

Keep going. Find the next guy. Grow.

— Beastly

 

 

 

 

 

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