As someone who has predominantly been a top during my sexual career I’m sometimes approached by men of all ages who want to try anal for the first time. I include the phrase “good with beginners” in my dating profile to show I have the patience and skill to make the big event as pleasurable as possible. Of course I’m hoping they’ll develop a taste for it and come back for more.
Perhaps the reason I do all this is because my own deflowering as a young man was far from pleasant. I’d unknowingly chosen one of the better-hung men in town to do it and his technique, if you could call it that, was blunt and involved very little foreplay. That I screamed with pain and bled came as a shock to him – he hadn’t considered that I might be a virgin.
For a vastly healthier experience, first decide whether or not you actually want to be penetrated up the ass and what it might involve. You might think this is obvious but you’d be surprised how many people don’t plan ahead imagining that it’ll “just happen.”
Choose someone you trust and be patient: “it” might not happen on the first date or the third if you’re not ready. It isn’t a race - it’s about pleasure, mutual pleasure. Shower first to warm the body and make sure you’re nice and clean – after you’ve been to the toilet of course. Kissing and cuddling, stroking and touching – lots of it – plus lots of lube. Foreplay – usually rimming and gentle fingering – is very important.
Penetration with fingers – first one and then two and then three – is next. Once this feels comfortable and pleasurable then it’s highly likely that a cock can go next. The easiest position for penetrated guy is sometimes called “monkey on a stick” – he sits on top of the penis and slowly slides onto it. This way he has maximum control of the rate of entry. It can be a bit of a balancing act at first but there’s no hurry. The second most comfortable position is doggy style – kneeling away from the fuck-er with bottom raised and legs slightly apart.
A problem with this position is that you can’t see behind you, so check that the man penetrating you has a condom on and that he hasn’t quietly removed it without “saying anything.”
From the top’s point of view, you need to be confident and considerate at the same time. Respect the limits – and pace – of your partner. Ask questions and supply answers. Discover things together.
That’s my virgin advice, I hope it helped.