bust (one's) cherry

vulgar slang "Cherry" is a slang term for virginity.

1. To have sexual intercourse with a virgin, especially a female. Before you go busting a girl's cherry, you had better make damn sure that you and she are both totally ready to sleep with each other. A: "So did you finally bust your girlfriend's cherry or what?" B: "Well, I wouldn't put it like that, first of all."

2. To have sex for the first time. There is nothing wrong with waiting until you're absolutely ready before you bust your cherry. Too many people try to pressure you into it from too young an age. I'm not looking for someone to just, you know, bust my cherry. I want my first time to be meaningful and with someone I really care about.

3. By extension, to do something for the first time, often that which is particularly daunting, difficult, dangerous, illicit, etc. Somebody pass Marcus the joint, he still needs to bust his cherry tonight! For her birthday, I bought my friend Samantha a voucher so she could bust her cherry sky diving.