I'm 26 years old and I have yet to succesfully have anal sex. I don't know if it's the girls I'm with or what. My one ex g/f was a thick big booty italian girl and it just wasn't happening. I couldn't fit. My next g/f was this tiny little blonde and I tried it one night when we're drunk and she jumped up so quick and just burst into tears. (Terrible experience) My g/f now is the one most experienced with anal and when I got just the tip in she told me "Nope this isn't happening." So I am confused. I've tried it with different sized girls and girls with experience and I still haven't been able to. Perhaps I just haven't met the right girl yet.