Personally I’m not even so much into anal, I definitely prefer a woman’s pussy over her tushy. However, the "anal question" has popped up with three different partners so far.
Years ago, I was having a love affair with a much more mature woman. It basically was a win-win situation for both of us; while I was extremely excited about pleasing this woman’s needs, she was enjoying sex with a fresh-faced, lecherous lover and we were going at it like rabbits at the time. She liked being on top in cowgirl position, but would usually lean forward on her arms so that we were face-to-face (or her tits-to-my-face
), lift up her hips a bit and then let me do all the work. She got extremely wet during intercourse and one day when we were having sex in her bedroom, I was ramming her wildly in that position - my dick slipped out and, with my next move, directly went for her backdoor. My dick only went in a little deeper than the head for about a second, but it made her squeal out and adjust her position so that she could quickly put it back into her pussy. With one hand in her butt crack she kept moaning about it for a few seconds until we both burst out laughing and reached our climax a little later. Afterwards she told me that she had never allowed a guy to enter her backdoor and that she certainly knew why. Although the feeling had obviously shocked her, we had a good laugh about it after all.
The experiences with the other two girls (an ex-girlfriend and my current partner) were not accidental but based on the girls’ curiousness. Since I enjoy myself much more in the submissive role, I’m not really turned on by sex that is painful for the girl. I’ve never felt the need to go for the butt hole, and it wouldn’t have happened if it hadn’t been the girl’s idea. Both my ex-gf and my current partner came up with the idea that we should give it a try. My ex was curious about it, but eventually didn’t like it. Despite using lube with it, I had to push really hard and after a few, not even full-length, movements in and out she said it hurt her too much and we skipped that part once and for all.
With my current partner it’s been a more pleasurable experience for both of us. We’ve done it several times and she finds it quite exciting, though she needs to have her clit fondled in order to reach orgasm when doing it the anal way. The feeling of being a “naughty” girl is definitely a bigger turn-on for her in that respect than the actual friction. I know her pussy gets her going much more, so we usually concentrate on the things she likes most…