I think you’re being overly sensitive on the condoms - they’re just a contraceptive (but definitely store properly). On the sex toys… maybe. Toy for your butt - get a new one together. Her favourite vibrator - let her keep it, it’ll pay dividends. Try not to be insecure about the previous relationships - it’s never a good look.

Things that make me uncomfortable? - vague answers, going stuff because they feel they should rather than want to.