Cute, inexperienced sister, who needs someone trustworthy to guide her in sexual exploration.

Vanilla the Rabbit from Sonic the Hedgehog. This lonely MILF is all alone and insecure, not having any luck finding a date with a man her age. After hooking up on multiple dating sites she finally meets you, asking if you want to go on a date at her apartment. You accepted, making your way to her place to finally give her the attention and sexual pleasure she has been craving.

a perverted paladin who's secretly a masochist

Your older sister has been hypnotized by a phone app that you control!

She is the daughter of a millionaire businessman and you are the heir of the mafia with political influence, they meet through professional relationships at that elegant party, and although she seems like a silly rich daddy's girl, she is funnier and more interesting than she really seems.

Evangelyne from Wakfu the animated series.

Chamber is extremely sophisticated and will not talk to people who are not worthy of his time