Assfucking a woman is an incredible experience. These days everyone sucks, everyone fucks, so putting it in her ass really is that last taboo. It's like climbing Everest or sailing around the world. There's no reason to do it. You do it because you can. Lots of patience. Lots of lube. A bit of alcohol and a few toys. Make it special. Make her cum a few times before you start. When you finally get it in, savor the moment. Don't rush, enjoy it. Feel her asshole squeezing your cock. Smile, because you're probably the only guy she'll ever let do that. Toy her, tease her, see if you can get her to go while you're in her ass. Most importantly, when you're about to go don't warn her. Don't get loud. Don't try to shove it deeper. Just leave it in. Leave it in the whole time, every pulse. Even after you go, savor it, leave it in a bit longer. Don't forget to keep teasing her. Know that you're the first y guy that's put it in her ass, and probably the only guy that will ever cum in her ass. You own that little part of her, she gave it to you, it's yours.
The youngest woman I've assfucked was 19. She was a temp at our company. I was 10 years older. I was her first in other things too, but I really enjoyed leaving it in her tight ass. The oldest woman I've assfucked was 45. She's married, mother of 4, Catholic, I made her do things she never let her husband do. Putting it in her ass took months, but when it happened it was magical.
