Sounds like this dude, consciously or subconsciously, can’t get over the fact that he sees OP as “his”, and he doesn’t like the idea of sharing her with people from the past. Depending on how old you are, 5 isn’t even that much for a body count, so i agree, him freaking out over that is a red flag. 18 is definitely more, but again, thats all dependent on how much you tie emotions to sex. Some people need a long emotional connection before they have sex, some don’t, and there’s nothing wrong with either. But being upset with how someone choose to use their body before they were dating you is childish and possessive IMHO.

If you like the guy, then you like him, but it sounds like a long distance relationship with someone too insecure and controlling to be in a mature long distance relationship. Lying is bad, crossing boundaries you two have set is bad, don’t do those things. But taking people’s money for talking on the internet causes no harm. Getting dick pics sucks, and I’m sorry you had to go through that, but if your BF blames you for that, he’s an idiot. Unless you said “please show me a picture of your penis”, nothing you did caused dudes to take pictures of their junk and send them unsolicited to strangers on the internet.

The extremely attractive and benevolent socialite with seemingly limitless wealth from mysterious sources that they are going on fetch quests for (which is about 60% of thr campaign) is actually a shapechanged amethyst dragon who is plotting an ascension ritual and is the big bad foe the campaign.

Also the seemingly benevolent order of monks are in actuality a cult for a far realm eldritch entity (a fact that only the highest ranking 5 members actually know), and the tattoo of a third eye all the acolytes get will actually anchor that entity to the world so it can come through and try to take over… but that’s next campaign.