Jill from Autie Pixelante's game Mighty Jill Off is probably one of the most unique, if not endearing, video game characters of today. For anyone, and probably many people, who haven't played the game - it's freeware and its through THIS LINK. Jill is a pudgy, lesbian gimp longing to service a dominatrix-like princess, and already the game turns the standard Mario (Save-the-Princess) conventions on its head.
Jill is throne from the top of the Princess's tower to the ground floor and has to climb her way back up to her quasi-romantic interest. Once Jill finally gets to the top to meet her princess, after leaping and dodging her way through many obstacles and enemies she is bound and ganged and told to do it again by her beloved princess (the end, and Jill looks thrilled). Unlike the Mario trope, the Princess is always in the same tower. Like Mario, she is just as unobtainable as ever.
Mighty Jill Off is about relationships. In an interview the creator likened this to the relationship she had with her partner, and the relationship between tops and bottoms in general. There is a constant amount of effort a person must go through in order to be with the one they love, and then once they make some progress and achieve a goal they may be faced with even more trials in order to meet their partners needs and expectations.
The story is also one of masochism. It is not exactly an easy game, which is perfectly fitted for a gimp. Constant failure, constant pushing on, and a seemingly endless tower with no break all work to display the struggle one goes through for their partner, to please them, even at the cost of their own person. Jill is always on bottom, and a boot fetish in the cutscene at the beginning of the game aids in pushing this logic. It is the only part of the princess she is able to touch, and she does so intimately. Jill is stepped on, she is worn down, and she is on the ground, because she is a sexual and relationship masochist. And her desire to return to the princess is not to be rewarded as a successful hero, but to be treated like a gimp, and punished again.
It's a strange story, but one which can be easily understood by many who are or have been the bottom or the submissive partner in any relationship. The game is wonderful as the gameplay and narrative work seemlessly hand in hand. They are one in the same thing, with the exception of some short, still-frame cutscenes at the beginning and end of the game.
Definitely check this game out. If you've played Super Meat Boy you can definitely see some masochistic comparisons between the relationships of Jill and her princess and Meat Boy and Bandage Girl.
Oh hey! While looking up links I ran into this post by the developer herself kind of confirming some of the things I said and suggesting some other interesting perspectives (especially on Super Meat Boy). Read it. Reading is good.