Ok, this is a question to anyone who can answer it -I am 18 and have started to engage in anal sex with my boyfriend. My question has to deal with the act of bottoming. The first two times we did it the pain was so great I could only handle it for about 45 seconds - 1 minute before I had to stop (this was with a tiny bit of fingering and LOTS of lube). It's starting to get better with each time we do it, but recently it's been really odd. One day it will not hurt at all and I can go until he cums but then the very next day it will hurt enough that he has to stop after a minute or two. Will it feel better as time goes on and I adjust more to him? Would a longer fingering session (5-10 minutes) make a world of difference? Is it odd that the pain / pleasure fluctuates so much?