First wife and I did anal on occasion and always finished inside her.

I came inside my wife's ass the second time we had anal sex. She spent the next few hours running back and forth to the bathroom as the brown-stained cum kept running out. She even put a wad of toilet paper in her panties to prevent accidents. I would've been fine with her just leaking all over the place (sounds hot to me), but after seeing how uncomfortable it made her, I decided not to do it again. She's since told me that I could cum inside her ass if I wanted to, but I haven't tried again--can't stand to see her suffer!