I have a few times. I used to use shower gels or foam soaps to help lubricate my hole, until I finally bought my first bottle of personal lubricant. I don't play with my hole anymore, as it's a mess to clean up (the lube that is, and washing it all off my hands/fingers). I would love some hot twink or older guy in his 30's to play with my hole and/or me playing with theirs.
I love holes