I have a supervisor who asked me if I put boobs on pogs when I was telling him about an elementary school business and how my sibling used to get angry at me because I would take there cosmo without asking if I could. Should I tell my manager?

OK, noticed the word boob, but don't know what "on pogs" is and what your kids have to do with it.

Guess I am just not understanding the story

But have you ?
1. told this person that the comment we unwanted
2. you can tell the supervisor

Yes. Your boobs must be a nice size for a comment (sexual comment - inappropriate)... being on pogs is like a offering yourself on a Pogo Stick (one for hot dogs) then goes about into your family issues... tell HR... someone above your supervisor... this is toxic and this is sexual harassment as well as personal harassment.