Not without modding. As Karryn progresses down the slutty route, she is Horny almost all the time. Cock stare and Flaunt will make her horny almost instantly (if she's not horny already). There are also butt-slap related passives that make her horny after getting spanked.
She is not using toys or undressing herself in the present version of the game. Only Nerds are equipped with toys and use them on her when toy criteria are met. Undressing works in similar way. Some inmates attacks will be undressing, especially if she runs out of stamina and lays on the ground.
Not sure what you mean by that. The guards outside the Office are there to train your skills, both martial and sexual. They also pay you some money if you win the battle. If you lose, they take you to your bed and have a groupsex session, as advanced as Karryn's desires allow. Her day also ends.
The upcoming update will have a guard-related title for servicing guards sexually in every possible 'battle' in a day: floor, bar, toilet, outside office and Karryn's bed.
