Handicaps are offered by Lilly Quinn at the start of some nights after you reach level 5, they usually give you a negative effect in being able to fight the matches, but, they give you a monetary bonus to each fight you win. There is no negative consequences to declining a handicap.

The first night Lilly is introduced, she will always offer the boxers-only handicap. After that, the handicap offered is random.

• Start in only your boxers, only receive boxers when resupplying: $100 bonus

• Start naked, don't receive any clothes when resupplying: $125 bonus

• Arousal does not empty on a win, unable to masturbate: $100 bonus

• Arousal raises by 5 each non-combat turn: $75 bonus

• Have the hypersensitive status for the entire match: $75 bonus

• Unable to use any pain attacks: $100 bonus

• Unable to use sex toys (dildo, tickler, onahole, riding crop): $50 bonus

• Unable to use any consumable items: $50 bonus