If you want to max out her masochism, then lose a lot, eat ass, lick fingers and get spanked. Provoke inmates to hit you with epecial techniques that will make her lose balance and fall. Give up during battles. Do not use handjobs, titjobs or vaginal. Try to keep her confidence below 100% for as long as you can, although she'll reach this eventually to achieve 1 Sadism point.
Though to be honest, collecting a lot of maso points will only grant you two relatively useless titles and that's about it. No further BDSM scenes or techniques will be unlocked other than those that are available in the game. Warden's masochism is expressed through rimjobs, butt slaps, getting hit in the battle (unbelievably stupid interpretation of masochistic desires), getting knocked down and 'suffering' defeat scenes. Her sadism is expressed by kicking erect cocks, denying ejaculations, hitting opponents in battles, giving footjobs, handjobs (?), titjobs (??) and pussy fucking (???). If you think the latter is the silliest misconception of sadism, then imagine that earlier versions of the game awarded sadistic point for getting buttfucked and enjoing it (using anal sex skill).
