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.
Thanks for the kind words. It blows my mind that my work is being read in Australia. You, sir, are on the cusp of your adult sex life, and that’s terribly exciting. There are a lot of questions in that question, so I’ll simply start at the top and work my way down.
In the beginning, you probably won’t be “good” sexually, because no one is. But you work at it, practice, make mistakes, improve, make more mistakes, improve some more, and gradually build up your skill. If you’re sexually adventurous and ready to have a lot of sex, and it sounds like you are, you might learn quickly. Lots of sex generates fast learning. But be warned: Lots of sex also means lots of letdowns, mistakes, lackluster hookups, and emotional hurt you will have to navigate. Sex is so much more than mechanics and penetration. It’s emotional and demands our trust, and can easily end in hurt when attachments and expectations get in the way.
Forget what you see in porn. I work in porn. Porn isn’t real. I see the messes, mistakes, and warmups that get edited out. These models have spent years training and advancing their skill and they still need significant time to mentally and physically prepare before a shoot. Even with all that preparation, they still need to take frequent breaks, clean up messes, and prepare their bodies — all of which get cut from the final product.
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 the most intense sexual experience you have now, but someday you’ll have intense sexual experiences that really happened, in which you were the star.
Building your expectations from porn is problematic because those expectations are impossible to achieve. You will not fuck at porn star skill level the first time you try. Sex might be lackluster or simply bad on the first attempts. That’s OK.
You will probably get clingy after sex, at least in the beginning. Most of us do. I certainly did. Sex is a powerful, life-changing experience. When we’re new, we tend to latch onto those we share the experience with, not realizing the fault in doing so. I’d tell you to not get clingy, but that’s like telling you not to eat. You will, and doing so will teach you valuable lessons.
You’ll get heartbroken once or twice (or more). You’ll get jealous. And in all of this, you’ll probably hurt someone else. Clinginess comes as quickly as it goes. You’ll meet another guy, you’ll get bored. You’ll cling from guy to guy until you can stand on your own feet. These first guys are your footing into a new world. They’re not meant to be permanent fixtures in your sexual development (and, in my personal opinion, no one is).
On to the mechanics. Start kissing and don’t worry over what to do next. When you’re kissing him, you won’t be thinking, “Shit, do I move into 69 next?” Who, for that matter, suggested 69 is an obvious next step from kissing? It’s not. Mutual oral (69ing) is way harder and way less pleasant than it looks in porn. Try it.
When in doubt, don’t think. Don’t trust what you think. Trust what you feel.
Just kiss him. Take his cues. Read his breath. The body knows what it wants to do. Good sex happens when you get out of your head and let your body take over — something even seasoned sex pros struggle to do successfully. When I let go and trust my body, sex is fantastic.
No, rimming doesn’t hurt. It’s your new favorite thing on this earth. Enjoy.