Most folks, at least the ones we’ve encounter, adhere to the condom rule also, especially with strangers.
DH has made jealous comments about your sexual past? All good as long as he’s playing too? Big red flag, HUGE. If he feels you’re enjoying yourself more than he is, big argument on the way home. Your partner makes you cum multiple times, big argument on the way home. Your partner has a bigger dick than DH, you guessed it, huge argument. I wish you two luck, but he’s not ready. Not trying to be Debbie Downer, just my opinion.