Is there any medicine that can make loosing your virginity hurt less? Like vaginal over the counter relaxant?

What pain? Grab a cup of joy, a dash of wonder, and a pound of true love. Mix that with 2 pints of sexual excitement and arousal (lots of foreplay), and all will be fine. Also, get to know one another's anatomy... both people should learn exactly where the hole is, and where it is not. The smoothest, easiest, controlled entry is to be on top of the guy, where she can adjust the penis pressure, rate, & speed.