Wow, lucky you with the squirter, Joe. Anal is fun, but only if you really know what you are doing, as otherwise you just hurt them. I would advise against the "Surprise!" anal stuff, as that will almost invariably hurt them.
As for being with another woman, TD, I don't know option 21, but just know that women are soft and they smell nice, and they often know how to get a girl off, because they have likely had a lot more practice than most guys. Don't do it if you are not comfortable with it, though, as that would not be fair to you.
As always, wishing all a squirting good orgasm,
-Forgetfulish