How much does hurt?

Get him to put one finger in, then two and let yourself relax. Use a LOT of lube (like a retarded amount) and take it super slow. Him on top and you laying flat on your stomach should work well. It feels amazing. is for fun and l is for making babies! And the guy who told you its gonna be messy is wrong. Very very rarely it will be a little messy but not most of the time.