@hhsq:
Practicing with dildoes really helps improve your hability of taking.
As for my own experience, pain has never been my main concerns when bottoming… shit has always been the most stressful thing ><
I think I mentioned in another thread the best piece of advice ever given to me, imparted to me by very sexy dude in very nonchalant offhand manner "Meh, you hit dirt you wash it off and start again". Mind you that thing between his legs probably reached places most weren't expecting.