I know this question has been asked a couple of times but even searching I couldn't find a clear answer.
What are the methods for raising masochism?
I have the following masochistic passives:
'Defeat after defeat' for losing a number of battles (not sure how many)
'Red Spank Marks' for receiving a number of butt slaps (not sure how many). Make sure you have your butt desire above 75 and encounter a lot of thugs.
'Masochistic Orgasm' for cumming several time while performing a masochistic act. At this moment the only decidedly masochistic sex act is rimming. Handjob, titjob, pussy sex and anal are considered... sadistic. Not sure if cumming while spanked or nipple pinched counts as masochistic orgasms.
'Excessive Confidence'... not sure if this is for high cockiness in battles or for losing high cockiness when defeated.
'Heart Shifting Towards Submission' for purposefully giving up / surrendering in battles.
'Eats Ass as Naturally As She Breathes' for participating in rimmings a lot. Make sure you have your mouth desire above 100 and meet a lot of guards and rogues. Once you learn how to initiate rim jobs use them at every opportunity like Karryn's on a tossed salad only diet.
There are several more masochistic passives, but haven't discovered these yet, as the concept of sadism/masochism is not that intuitive in this game. Qualifying openness to penetrative sex (except oral) as well as tit fucks and handjobs as acts of sadism is just plain wrong.