I’M ALEXANDER CHEVES. MY NICKNAME IS BEASTLY. I WRITE ABOUT SEX.
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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 locker room 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.
Hi first-timer,
It blows my mind that I’m being read in Australia. Thank you for reading my blog. You are on the cusp of your adult sex life, and that’s exciting. I’ll start with the first question you ask and work my way down.
In the beginning, you will not be great at sex. No one is. You will only improve through practice and experience. If you’re sexually adventurous and ready to have lots of sex, you might learn quickly, but be warned: lots of sex also means lots of letdowns, mistakes, lackluster hookups, STI risk, and new 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 can (and will) get messy.
Also, forget about porn. I work in porn — porn isn’t real. They’re acting. I see the messes and mistakes that are edited out. Your first attempts at sex will be nothing like porn, and if you compare these experiences to porn, you’ll believe you’re lacking or doing something wrong.
You’re not doing anything wrong. You’re just inexperienced, and you’re not a porn star. No one fucks like porn stars — not even porn stars — because porn star sex is a fantasy. Lackluster sex can look great with some good video editing.
Real sex is better than porn. Porn may be an intense experience for you now, but someday you’ll have intense sexual experiences that actually happened to you — memories of great sex that are yours — and porn will lose some of its luster because you’ll start masturbating to your own memories (in addition to hot videos online). Enjoying porn will probably never vanish from your life, but after some years of sex, you’ll be able to distinguish the differences between porn sex and real-life sex.
You don’t want a relationship right now. I promise. And yes, you will get clingy after sex, at least in the beginning. Most people do. Sex is a powerful experience, and when we’re new to it, we tend to latch on to those we share it with. I would tell you not to do this, but that would be like telling you not to breathe. You will do this, and doing this will teach you valuable lessons — how to get hurt, how to move on.
You will get heartbroken. You’ll get jealous. You’ll probably hurt someone else who does not deserve it. 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 will be your stepping stones into a new stage of life. They are not meant to be long-term fixtures of your sex life. Even this current older gentleman will be a brief stop on the road to sexual selfhood. Many men will likely follow him before you feel confident at sex.
Start kissing him and don’t worry about what to do next. Just do what feels good to you at the moment, and if you’re very nervous, tell him you’d like him to lead. Consent is important, and you should tell him directly to keep going if you want to keep going, and you should tell him to stop if you feel uncomfortable. If he ignores what you say, leave any way you can and don’t speak to him again. If he ignores or overrides your consent, he’s an unsafe sex partner.
Who suggested that 69ing is an obvious next step from kissing? I don’t think it is. Mutual oral sex (69ing) is harder than it looks in porn — it is not actually a very pleasant experience to me. I suggest simply touching his body wherever he wants you to and letting him touch yours wherever you want him to. Don’t worry so much about positions. Gay sex in porn is a ridiculously coordinated activity in which positions are selected for their camera appeal, not for their ease or pleasure. Real sex is different. In real sex, your focus will be on each other, not a camera. Again, I recommend asking him to lead.
No, rimming does not hurt. If he’s a good rimmer, it will be one of the best feelings you’e ever felt.
Unlike porn, your first sexual attempts will be over-eager, awkward, and probably unrewarding. You might make a mess. It might hurt. You might have unexpected doubts and insecurities that appear after you try for the first time. You might not enjoy the experience very much. Receptive anal sex often comes with pain and problems we can’t foresee in the beginning. Use lots of lube, and unless you have easy access to a sexual health clinic, I recommend using a condom. If you’re HIV-negative and out to your doctor — as you should be — ask him about PrEP, a pill that prevents HIV infection. If sex sucks the first time, keep trying. It gets better.
Love, Beastly
Love, Beastly 
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