Crossword puzzle clue "having your first shave or buying your first bra e g"

Having your first shave or buying your first bra, e.g.

Having financial trouble, like a bra manufacturer?

Like either option in "Would you rather watch a video of your parents having sex or your parents watch a video of you having sex?"

Shave some years off your age, e.g.

First bra, perhaps

"Buying your weed wearing a pot leaf T-shirt? Like that's original"

Lebowitz who said "Ask your child what he wants for dinner only if he's buying"

Bonus upon buying your twelfth acre of farmland?