The Adult's Guide to Losing Your Virginity. Vanessa Marin. 6/04/15 7:00pm. there’s also the emotional weight that you assign to your virginity. Would you like to lose your virginity with. Does it hurt to lose your virginity? The first time you have vaginal sex, it may hurt, or feel good, or both.There might be pain and bleeding the first time a penis or fingers go into your vagina, but it doesn’t happen to everybody. Jul 29, 2017 · HOW OLD WERE YOU WHEN YOU LOST YOUR VIRGINITY!? Make sure you sign up to guarantee your spot because spots are limited as I only wanna create a small test group to work with. AT WHAT AGE Author: Adrian Gee.