Oh, I see. That explains it to an extent. It still sounds like the pleasure damage is a bit too high, but probably not by much. Unfortunately, on Normal and up, if you don't have a decent idea of what you're doing with Karryn and some understanding of the overall mechanics, you'll start getting screwed over in some fashion on Level 3. If you were going for combat and then lost at some point and started accumulating passives, you wouldn't have the stats to properly handle their effects.
It's pretty much a downwards spiral for Karryn once she starts becoming more and more sensitive, and this isn't helped by the Nerds and their Expose Weakness debuff, which lowers her resists and makes it much likelier for her to crit... and crits apply to pleasure attacks too.
Given how the game is meant to be played, I recommend trying to grab whatever titles you think you can with that situation, and then deliberately triggering a bad end and starting over. All the different variations in play-style, which grow all the more numerous as Rem keeps adding more content, is in theory half the fun of the game.
Yes actually. The first passive you'll need is "Full Service Waitress", which lowers all the desire requirements while working the Waitress job. You get it by having sex as a Waitress. Then you need "Hedonistic Waitress" which lowers the desires even more, and it's obtained by Karryn getting fucked ten times during the job. At that point, she should start flashing at over 80 Boob desire, though she'll really go all out only once you get "Made the Bar her Fuckroom" which requires a wooping 30 times of fucking in the Bar, that's 30 days btw. Of course, by the time you get that, you should be able to get flashing to happen anyway.
Keep in mind that you'll need to keep fixing her clothes, and you'll also need to keep her Cock-Desire as low as possible. That's what speeds up the triggering of the drunk sex scene.
And no, it's not really possible to get Karryn to flash without her slutting it up in the bar first. Getting her drunk helps, but only up to a point, and if she gets dead-drunk, cock-desire stops mattering at some point, and she'll enter into the drinking scene, where the prisoners keep giving her pale ale if you keep her cock-desire low until all of them finish cumming all over her.