Jailbreak is the first MS Paint Adventure
done by Andrew Hussie. Nominally unfinished, it did eventually recieve an ending of sorts when hussie made a final command/panel
during one of Homestuck's many haituses. Only the first panel of this was made in paint, the rest being done in Photoshop.
During this game, Hussie took suggestions for the command to be done by people, however he took the first suggestion given per command,
resulting in a somewhat random and convoluting attempt at escape. There's not much in terms of narrative and pauses, which makes this Lets Read somewhat hard.
Anyway, moving onto the story...
So, the adventure starts in a jail cell, with nothing but an unnamed character (who I'll call Cell-Dude for disambiguation later), a barred window, a key and a pumpkin. The first few commands yeild us nothing but the starts for two running gags (pumpkins that do/don't exist and calling to get arms you have (but weren't drawn)).
The adventure continues, as we look for a keyhole. The pattern of commands not being interpreted the way you'd expect starts here as we look out of the window, instead of around the room. We find a keyhole in the door down in the courtyard below, along with a second unnamed character, who we'll call Courtyard-Dude. He leaves through the door without hearing Cell-Dude or see Cell-Dude throw him the key.
This series of strange commands and stranger, yet humourus, interpretations continues as Cell-Dude finds another keyhole (in the cell door), knocks out two other characters (Courtyard-Dude and CorriDude, both of whom were in the wrong place at the wrong time) until the adventure switches to Courtyard-Dude.
As there's no real difference between the characters, the same series of peculiar commands continues. There's a series of building stuff from Courtyard-Dude, who eventually gets the key to the Guy-Above Cell-Dude. With the characters having no discernable features, besides their current and starting location, there's not much to them to make them particularly compelling. Entertaining, yes, but nothing too major.
Holes are made, pee urinated, vomit up-chucked (I think there's a handful of peeing on things jokes in Problem Sleuth, at least in the early stages of the adventure). Cell-Dude eventually tries to get some of the keys dropped by Corridude, to no avail.
After a macabre section involving using CorriDude to ram open the cell door, we get the start of another, possibly minor, running gag, the appearance of Hunk Rump the gay porn that pops up occaionally.
Moving to Courtyard-Dude, there's a Build a Bot sequence that ends with an option time! Two storylines to follow (something that doesn't come up that much in MSPA. it's fun, but I get why it wasn't done that much). Each, short, storyline follows Cell-Dude in one line, Courtyard-Dude in the other, as they work on escaping from the jail. Plenty of actual pumpkins are used before the storylines rejoin.
The two protagonists briefly rejoin, before parting again to be in each others rooms. More shenanigans are had which, looking at my notes were ok to read at the time but not so much now.
Through a series of convoluted commands and interpretations, the pair escape, and end up at a stump in a forest. The stump, which is another running gag (or location) is called the Suicide stump. Both characters pass on, and the game resets, throwing us back to the starts since we never saved!
Resarting back at the initial panel, a completely different set of actions are taken. While the first time round was alright, by this time it was just tedious to get through. Runes are read, elf summoned, and gay porn is used to make a sword (it makes sense in context).
We get into a fight, showing off the first fight of (at least) several that feature in the MSPAs. It doesn't go successfully, alas, and we try bribing the elf with a baby (that Cell-Dude will get in the future). This is surprisingly successful, and the fight-wish sequence is repeated again, and we're whisked to the forest.
A series of stupid commands are given featuring another character change, to one of the elves, eventually we command the pony to do something it elects to ignore before clmbing into bed. Then we're treated to the final command that was added years later, "Enjoy restful slumber" treating us to a "You Win" screen.