I seem to do pretty good with the ladies, so I guess I've proved myself worthy /shrug
The part that you guys are missing is that pegging (or fucking her up the ass for that matter) are hardly activities that you flaunt on a first date. Is there an aura about me that tells women "this one likes to take it up the ass and is therefore not a suitable mate"? Of course not. I am very alpha with the opposite sex, whether I am romantically interested or not.
I gave my current gf her first orgasm, then her first multiple orgasm. I am the fucking man in our relationship. That said, my ass gives her a giant ladyboner and she likes to lick or penetrate it sometimes. It is not the only sexual activity that we practice, nor is it even the primary kind.
But I can tell from your post that you are looking at this from a very beta mindset ('what if I get rejected'?) instead of asserting what you want. I would not ask every girl to do this. But then, I probably would not be dating her, because her taste in sex were too vanilla for me.