You might wake up the morning after doing the deed and feel a big, whopping… nothing at all. The real answers to these questions? But that might not be so clean-cut, either. Or maybe nothing so dramatic, but real talk: And just with the other myths, no one can tell you when is right except for you. Bridgette, a collegiette at the University of Mary Washington, received plenty of it before Is loosing your virginity painful lost her virginity to her boyfriend at the end of freshman year.