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kingsman wrote: ↑Sat Apr 20, 2019 3:09 amYou simply need to take control of the situation and direct him. Give him no option, so that when repeated enough he comes to understand that sex = anal. When anal becomes the norm then I expect that he will lose his shyness. At the moment what is holding him back is what he believes your perception of him will be if he asks for anal. I think you'll be doing him an enormous favour, not only in terms of normalising anal, but his overall character and self confidence.
I agree. You need to take control. Positions that let you control the situation are a great way to do this. If you're on top, say in cowgirl, you can simply reach back and guide him into your ass instead. The first few times my wife and I had anal sex, we were in the doggy style position having vaginal sex, and she kept arching her back when I withdrew to make her ass more accessible. It took me a bit to get that that's what she was wanting.
Another option is to tell him your vagina is bothering you, or wait until your period and tell him you'd prefer it if you just did anal. The problem with this method is that he may think that's the only reason you're doing anal, but that you'd actually prefer vaginal.
Of course, your reaction should make it really obvious which you prefer. When having anal sex, you should be very into it. Let him know you enjoy it by your moans, or dirty talk (if you can pull that off). My wife is a terrible dirty talker, but a great moaner and "yes, yes, yes" or "oh god, oh god, oh god" er. I've never heard of any man that didn't love making a woman moan or scream.
Unless he's got some kind of weird hang up, he'll come around.
And what's more, he will later thank you for it. It's not so common but some men are less assertive than their woman. He just needs the green light from you that it's okay to go for that arse of yours than your pussy, that it will please you and you won't think any less of him.