So rough introduction, in my friends camping I am playing an archaeologist bard archetype (Pathfinder) meant to be a lucky ass pickpocket who could talk his way out of a hairy situation. And the world is low fantasy (so little magic thus the archetype).
We started in a wagon caravan, in our wagon sat the party (a tank fighter, an alchemist, a barbarian and myself) along with two other chaps, a ex-royal guard and an explorer. And of course the first interesting thing that happened was the explorer was trying to stealthily gawk at his new shiny gem (with a successful perception check later we all saw it) and I decided to speak up about it after an appraise check tells me that it's worth a good grip of coin for a beggar.
So I start in on the poor explorer, I asked him very nicely in the best cockney accent I can muster, to look at the gem his is looking at convincing him with a bluff check to let me appraise it for him, telling him I was a self taught expert in valuing items, the royal guard started to be shifty at this, he threatens to kill me if I even touch the gem, so we come to a compromise and the explorer would hold it for me and I wouldn't raise my hands at all, seemed like the best option at the moment.
So this is where the plan took hold, with a successful bluff check I convince him that t gem is worthless, and offer to pay full price for the gem as a compensation, (he was looking to get maybe 100 go for it) and he demanded to see the payment, and with the time I've spent panhandling before this trip I had enough to pay for it. Then the ex-royal guard pulled him in and told him that he didn't trust me, honestly rightly so in his defence. And after I twisted a story about how even if the gem is fake he still has a story to tell his friends and family and that it would ultimately be more beneficial for him and what not. And finally after 10 minutes of convincing he gave it to me in exchange for the payment. So success for this beggar, a 900 gp profit.
Then shit went bad, after an ambush and a successful counter attack later the party ends up being the only survivors of the caravan. Then we walk an hour to town, it's dark and the gates are closed, well damn, time for the face to face, and after a few failed diplomacy checks later I am arrested. Then in the morning I am taken to be presumably interrogated by a bunch of dudes in black robes and masks, and after a talking to later form a bunch of cryptic asshats who had nothing better to do then not believe a single word I had to say, after a very tense talk about the gem I had and a few torture threats later, I was then taken to a nice cell to await my public hanging. And after looking around my cell I find rope under my bed, and the bars on the window had been tampered with and one of to was able to be removed making an escape route.
After some confidence building I make my way out of the window and climb down the rope. It took me half way down the tower and after looking there was a roof that I had to jump to, and a failed acrobatic check sends me falling, but a successful dexterity check allows me to grab onto a window ledge and I catch my breath for a second. The I realize I have to assassins creed this shit and drop down catching myself on small window ledges I successfully make it down two ledges and the realize that this window can be opened and I sneak in and hide to compose myself after almost dying three times. I had landed in a great dining hall and there were maids and butlers coming in to set up lunch or something, I didn't stay to ask.
And lucky ass me happened to hide under the table that a cart stopped right in front of. And realizing that the bottom was filled with removable trays so with a slight of hand check I make myself an escape route, I get in, the maids and Butler were too stupid to look under the cart so I got a free trip to the kitchen. Then with another bout of luck the trash shoot was right next to me, I dove in and mission impossible my way down the trash shoot. When I hit the bottom I found out that it dumps out into the moat, the light at end of the tunnel (figuratively and literally) I made it out and one of the gate guards decided he was better at looking then everyone else, and now a pursuit ensued again.
And after some frantic swimming in the moat I see a small tunnel leading BACK INTO THE CASTLE I JUST ESCAPED, after some thinking I chose to follow it down and a few swim and fortitude checks later I make it to an air pocket and realized it was a secret passage back to the normal cells is the jail and a chest containing my gear (an expensive ass wrist blade) and no gem, damn there goes my pay day and now I'm out 100gp. I decided to crawl back into the hole and wait out the search. And a few minutes later the plank concealing the secret passage is moved to reveal a trio of black clocked cryptic asshats aiming crossbows at me while I'm floating in water, but close quarter walls, the one in the middle decides to try and out a nose around my neck and with a escape artist check I get out of it, and a few acrobatics checks later I dodge the crossbow bolts. From there I decided to swim like a mad man and take the other rout in the tunnel and make it to the royal crappers, a fortitude save keeps me from vomiting underwater and I look for a way out. I find a bared off exit and with a little bit of thought I mythbuster the hell out of this situation and twist the bars out of the way with a over shirt I had on. And I make my out to the river outside of town, and I got away to hide out for a bit inside surrounding forest.