Here's my tips/experience if you do decide to do it:
I do enjoy having him place a finger pressing on the anus, but HATE having him actually finger me. All the advice of stretching things with a few fingers first wouldn't work for me. I also like him to lick the area a bit. But other than that, I don't do much preparation. We just make sure he's got a lot of lube on himself and some on me. Then when we start, he stays mostly still and I rock back onto him at my own pace. Once I've got him mostly in, then he can start thrusting but it still has to be nice and slow initially. But after that I quickly get into it and we can go a little rougher. Play around with positions. Some will be harder to get yourself relaxed in. Our favorite (also our fav for PIV as well) is with me lying on my stomach and him straddling my legs. It doesn't sound like it would work but it does.
Finally, anal can be a lot more emotional than regular sex. The first few times I was very sensitive about it and my boyfriend was great. Even now, months after we first did it, he's still a bit more affectionate during anal than PIV. He leans in closer and kisses my cheek or my shoulder. That's probably one of the things I like most about it.
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