When You Sleep With Another Man For The First Time

We live in a time where people are more open about sexuality, but the heterosexual experience continues to dominate; “boy meets girl” is still the default in most of our cultural references. If you’re a man who feels their destiny may be elsewhere, the idea of sleeping with another man might feel daunting. Whether you’ve only slept with women or never had sex at all, a first encounter with another guy may not match your expectations. I can’t tell you whether it will be great or terrible – that depends on who you’re with, where you’re at and the situation that led you there – but here’s a heads-up of what might be in store.

T H E  K I S S

Arguably, the most exciting part. Contact is made. There’s no guarantee it will go further but… you can’t be unkissed. Fact is, men kissing for the first time usually kiss too aggressively. Maybe you’re not used to it. Hard kisses have their place and are welcome and nobody’s suggesting you peck each other like warring hens, but there are side-effects of a hard, full-on snog. The unexpected shape of the chin. The pressure of his mouth against yours. There may be stubble and if there is, wow, it’s coarse and scratchy. Your own chin might, depending on your own beard situation, start to feel raw, as will your lips as they scratch against his face. Your pain receptors may not feel it right away because you’re lost in the moment and “holy God, oh, wow, oh, wow, this is finally happening and it’s amazing” and maybe it’s everything you ever thought of and more. But, eventually, the stinging will find you. Go gentler than usual; be gentlemanly and suck face rather than sandpaper it. Tip for post-kiss beard irritation: use water-based moisturizer on your lips, not Vaseline or other oil-based ointments, which can make the burn feel more intense.

T H E  B O D Y

You may think you know everything about a man’s body, that there can be no surprises lurking. You’re wrong. The variation from your own can be startling at first. Like you, but… not. If you’ve only slept with women before, the feel of a man’s body and the different shape may shock you. You might be frightened to touch it, unsure of boundaries because of the unfamiliarity of the situation. Don’t be frightened, be curious. The first time you press your chest against another man’s is the strangest, most exciting thing. Your nerves will be jangling at the strangeness. Allow them to propel your forward, don’t shrink away.

T H E  D Y N A M I C

If you’re used to sex with women, the power dynamic may feel different. Many men feel they should take the lead with women, that they have a responsibility to them, to be the best performer, giving the most pleasure, that the woman should, in every sense, come first. There are also lots of men who don’t and just hammer away at the poor woman until the timer on the microwave pings that their lasagne is ready, but here’s hoping you’re not that guy. 

Thanks to the patriarchy, sex between men may feel like you’re more an equal, so you might be unsure what your role is. Should you initiate moving on to another step, should you change position, do you reciprocate oral sex or is it OK to only give or receive? This is an opportunity for you to be led but also to try something new, to be whoever you want to be in that moment. You can control your own pleasure. Whether this is the first of many or a one-off, now is the time to say exactly what you want. Pretend there’s no tomorrow.

T H E  P E N I S

Well, there it is. Probably not like yours at all. You will compare, you might be self-conscious. You know what this thing does and yet it’s still a huge mystery – like you can, theoretically, drive any car, but you never know how it feels until you take the wheel. Turn this nervous energy into bravado – go forth, touch it, feel it. Keep your eyes on his while you do; see how he responds to your touch. The feel of it in your hand will be surreal at first. When it comes to handjobs, think how other people touched your dick before. Too hard? Too soft? It’s trial and error, after all, and if the only dick you’re used to touching is your own (hey, no judgement, days are lonely and nights get long), you might worry you’re not doing it right. 

One tip: like the kissing, start gentler than your first instinct. If they want you to step things up, they’ll tell you. The benefit of having sex with another man is, if they’re experienced, they’ll know what you’re worried about, what scares you. They won’t punch you in the balls for the fun of it. Don’t be squeamish about it, try not to flinch, it’s all right. Tell him it’s your first time. No man worth his salt aims to be remembered as a horror story; he’ll want to be a hero, the stuff of legend. Men will be men, y’know?

While we’re down here: the scrotum. A bit of a surprise. Real-life ball bags seldom look the same as those shiny, waxed eggs swinging valiantly in the breeze in pornographic movies. So overlooked, dismissed as functional, with a bad reputation as not being particularly decorative. There’s no need to be afraid. There’ll be stroking, maybe even some sucking if you’re both down for it. Everyone knows about blowjobs and many a straight man would shove their penis through a glory hole with little care for who’s on the other side, but the balls are more intimate. Put simply, in a metaphor that I feel may haunt my career for decades, if blowjobs are the main event, your balls are the secret afterparty. Sure, you can have just as good a time without going that way, but for the full experience, well…

T H E  S E X

How far should you go? Your fantasies may not match up with your reality. You may be chomping at the bit to do everything or you might follow your instincts and go slowly. If you feel tonight’s the night for taking a man in your mouth, go ahead. If you don’t like it, make it only a brief interlude. You will wonder how to approach it, worry you’re doing it wrong. Luckily, I can help with that: take a look at my blowjob guide from a while back. 

Receiving a blowjob is every bit as nerve-wracking as giving one; you’ll experience all kinds of emotions while it’s happening. Is this the best blowjob you’ve ever had? If it’s your first and you’re not supple enough to administer your own, then, yes, maybe. He might look at you while he’s doing it. It’s OK, you can laugh. Or stare back. Or look away. No rules. You might do all three. Go with it, clear your mind, give into the moment. You will seldom be more vulnerable than right now and it might frighten you. That’s cool, but don’t be scared, think of the upside: you’re getting your dick sucked. Result.

There’s no pressure to have penetrative sex at all. Maybe he’ll ask, maybe he’ll manoeuvre you both so it seems inevitable. You’ll be nervous. Excited. It seems a big deal, like you’re giving, or taking, something away. Only you can judge how important this act is to you. It might hurt, or be uncomfortable, or feel incredible. You might want to run to the loo “just in case”. It might be awkward to get into position if you haven’t done it before. Start slow, check in with each other, communicate. You can talk. This is not a movie. You may be surprised missionary is indeed possible between two men. Maybe you’ve romanticised it, or fetishised it, or dreaded it. It will be unlike anything you’ve ever felt, whichever way you do it. The closeness of it may be terrifying and exhilarating at the same time; you might shout out things that surprise, feel an intimacy that overwhelms you. There’s no right or wrong way to feel about this, but at least you can either say, “Well, I tried” or “Shall we go again?” and feel proud of yourself either way.

If you don’t want to do it, instead explore the rest of the body as you wish. (But if it’s happening, be safe.)

T H E  C L I M A X

You are under no obligation to make someone come. It’s nice if you do, obviously, but it’s no reflection on you if you don’t. There are nerves to consider, on both sides, and it doesn’t have to happen straightaway. Assuming this is not a quickie in your lunch hour (again, no judgement, sandwiches are so carby), maybe you’ll come back and finish off later, when the pressures and the franticness of that initial contact have subsided.

How are you with ejaculate? Yeah, not a question you’ll hear in any pub quiz but worth mulling over, if you get time. Sorry to be blunt but bunking up with a guy means sharing space with semen that doesn’t belong to you. Where do you want it? Can you handle it? You’re used to controlling your own when solo and, if having sex with a woman, maybe you’re not bothered where it lands because you’re desensitized. But this is coming – ha! – from another. Be ready for it. Perhaps swallowing has charged your dreams for months on end and you can’t wait to do it – great! (Have a glass of something handy to rinse.) Wherever it ends up, you will feel a sense of achievement when you make a guy come. You can’t really add this extra skill to your LinkedIn, though.

After: cuddle, relish the closeness. Now is not the time to revert to “hey bro” body language and awkwardness.

T H E  F E E L S

As well as the physical, there’s the emotional side to consider too. Things might fall into place about your sexuality, but it doesn’t have to be a final, irreversible decision. It’s not uncommon to romanticize early experiences – or be repulsed by them – just give yourself time to work yourself out and don’t make snap judgements. It means everything and it means nothing. You’re still you.

If this confirms your sexuality for you, great, but if it was an experiment or action with no bearing on your sexuality, that’s fine too. Labels are complicated because they can liberate us, protect us and, sometimes, restrict us. It’s all about respecting how other people identify and knowing your own mind. You might find that sleeping with a guy has answered some questions, but not how you hoped. Talk to someone. Whatever you do, don’t take out your frustrations on the guy you’ve just slept with.

It may well be awkward and frustrating. The earth might stay resolutely still beneath your bouncing buttocks. First times are usually less than perfect – just ask anyone making a batch of pancakes or trying to record a sexy voice note – but, if you’ll pardon the expression, that means the only way is up. Whatever, or whoever, you do next, make it count. Life is not a rehearsal. Don’t die wondering.

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