It might be awkward to get into position if you haven’t done it before. You might want to run to the loo “just in case”. It might hurt, or be uncomfortable, or feel incredible. Only you can judge how important this act is to you. It seems a big deal, like you’re giving, or taking, something away. Maybe he’ll ask, maybe he’ll manoeuvre you both so it seems inevitable. There’s no pressure to have penetrative sex at all. That’s cool, but don’t be scared, think of the upside: you’re getting your dick sucked. You will seldom be more vulnerable than right now and it might frighten you. Go with it, clear your mind, give into the moment. He might look at you while he’s doing it. 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. Receiving a blowjob is every bit as nerve-wracking as giving one you’ll experience all kinds of emotions while it’s happening.
Sure, you can have just as good a time without going that way, but for the full experience, well… 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. 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. There’ll be stroking, maybe even some sucking if you’re both down for it. So overlooked, dismissed as functional, with a bad reputation as not being particularly decorative. Real-life ball bags seldom look the same as those shiny, waxed eggs swinging valiantly in the breeze in pornographic movies. No man worth his salt aims to be remembered as a horror story he’ll want to be a hero, the stuff of legend. Don’t be squeamish about it, try not to flinch, it’s all right. They won’t punch you in the balls for the fun of it. The benefit of having sex with another man is, if they’re experienced, they’ll know what you’re worried about, what scares you. If they want you to step things up, they’ll tell you. One tip: like the kissing, start gentler than your first instinct.
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. When it comes to handjobs, think how other people touched your dick before. The feel of it in your hand will be surreal at first. Keep your eyes on his while you do see how he responds to your touch. Turn this nervous energy into bravado – go forth, touch it, feel it. 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. You will compare, you might be self-conscious. Whether this is the first of many or a one-off, now is the time to say exactly what you want. 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. Thanks to the patriarchy, sex between men may feel like you’re more an equal, so you might be unsure what your role is. (Tip for post-kiss beard irritation: use water-based moisturiser on your lips, not Vaseline or other oil-based ointments, which can make the burn feel more intense.) Go gentler than usual be gentlemanly and suck face rather than sandpaper it. But, eventually, the stinging will find you. 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. Your own chin might, depending on your own beard situation, start to feel raw, as will your lips as they scratch against his face.
There may be stubble and if there is, wow, it’s coarse and scratchy.
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. Fact is, men kissing for the first time usually kiss too aggressively. There’s no guarantee it will go further but… you can’t be unkissed.