Masturbation Confusion 😲

So I'm kind of new here.. And this is very awkward to ask, but when you masturbate, are you able to 'pop the cherry'? During sex I don't want to bleed. Especially my first time, that would be super embarrassing. I'm just really confused on how down there actually works, my mom isn't that much of a big help about it because we hardly talk. It would be completely stress relieving if you guys could help me gain more knowledge 😮

Thanks!