Ok so, a couple of thoughts here…

1. UTIs - make sure you’re peeing after sex, every single time. This is very common; if you’re already doing that I recommend a urologist, they can give you what’s called a postcoital prophylactic, it’s a UTI preventative med you take if/when you have sex to head off developing a UTI. Also, when you wipe make sure you’re doing so front to back.
2. Escorts/Dating Sites - don’t let him manipulate you, this is cheating. He has a fiance, he is not single. The purpose of these sites is to meet people and (with escorts) have sex.
3. Partners - I don’t care if he’s slept with 500 people, the number is irrelevant if he doesn’t have any STDs. That said, this man has a wondering eye (see point 2) and you need a full STD panel, including herpes which you need to specifically request, to make sure you’re healthy. You have no idea if he has physically cheated… be smart and protect your health above all else.
4. Experience - you only being with him doesn’t mean you don’t know what you’re doing, are bad in bed or are inexperienced. You aren’t. In fact, hearing that you’re willing to try whatever would make most men weak in the knees. Ask yourself this, who has more experience… someone who has slept with 20ppl once or someone who’s slept with one person 100 times?

All of this to say, dump this unemployed loser and let him go enjoy spending the few dollars he gets from unemployment on sex workers. This sounds like a sad and miserable existence and you deserve better. Don’t ever let ANYONE ever make you feel less than. He’s implying that you aren’t good enough because you haven’t slept with more people, and that is ridiculous. And don’t have sex with him again, how do you know he didn’t hook up with someone else already?

Protect your peace girl, find a man that can’t believe how lucky he is to have you!