Aloura, the Klepto Tabaxi Sorcerer

So I'm new to the forums, figured I'd toss some fun stories around. I'm a fairly new DM, though I'd like to think I'm pretty competent. My party makeup has changed a good five times since the campaign has started, but one person who's always been there on my adventures is a young female half-tabaxi named Aloura. For some reason she's a sorcerer, she claims it's because she enjoys magic-users, but I don't understand her choices when all she ever does is try to find things to steal.

So you know the typical setup already, she's a tabaxi so she can climb fairly well, she has a +1 to Dex so even if it's her dump stat, which it isn't, she'd be okay, and she chose her utility spells before her combat spells. Mage hand, Prestidigitation, and then as they became available, Knock, and Invisibility. She's at level 5 right now but I tremble to think of the things she'll do once she gains even more potent spells. She's a good role-player, and she doesn't typically steal from the party or make herself an enormous nuisance, so I let her do what she wants and let the dice decide her fate. This turned out to be a harsher sentence than I had initially intended solely because when it comes to the dice she has about as much luck as Wil Wheaton...

First session, all my shiny level one players have just been given the layout of the small village they started in, their characters are familiar with each other, though probably not close right off the bat, Aloura decides the first thing she wants to do is look for the nicest house in town. Rolls Investigation... 11. Finds a decently sized home made of more brick than wood, which IS a sign of wealth in this part of the world, almost surrounded by forest patches and very few bodies of water around them to supply the clay for bricks, she decides to rope the party's druid, Donia (dump stat - Charisma because... druid...), into helping her case the house and then breaks in. Donia (a Tiefling) isn't very good at subtlety but does her best and manages to roll a Nat20 Perception to be Aloura's lookout. This sounds like a good setup, except it's the middle of the day and they don't know who owns the house, since they spent about... ten minutes casing it before Aloura got bored and decided to expedite the heist.

I described it as a single roomed cottage type deal with a higher up window in the back of the building for ventilation, mostly. Aloura, being a Tabaxi, has advantage on athletic checks involving climbing, it's not a high wall, probably about 12 feet or so to the window in question, but I still make her roll for it, just for flavor, and also since she's trying to not draw attention from the stretching dirt road in the thoroughfare of town in FRONT of the house. Good thing she rolled advantage, the first roll was a Nat1, second was an 8. She had a plus two in athletics which works out since she needed 10 to not fumble up the side of the building and probably make a lot of noise.

Aloura gets inside, barely, but the building has two large windows facing the thoroughfare and there are a couple people walking around. It isn't a large settlement, but it has enough hustle and bustle that it's hard to pick a time to approach the house during the day where no one is around, so once she's inside I made her roll stealth to avoid being seen from the street. She's barely hitting the mark on my checks. like coming within 1 or 2 of failing each thing I present to her... but she's succeeding nonetheless. As such, I feel obligated to make her make a single quick Investigation check to find out what's valuable in the house, since everything's kinda cluttered in this one room, kinda Skyrim or Witcher style. This is where it gets fun...

Aloura rolls a Nat1 investigation. Not only that, but since they didn't know who owned the house, Donia (who's still watching outside) could have rolled any number, but unfortunately due to lack of information, and also not being within earshot of Aloura without shouting and giving herself away, she missed the owner of the house approaching the front door. Aloura is a Tabaxi, and as such is prone to getting an urge to own a random particular object, completely at random, and so I describe it with the flavor of: "You glance around the room, searching for strongboxes, small jewelry or coin sacks, anything that may be worth selling later, but as your eyes run across the countertop in the kitchen area, you stop. You can't pull your eyes away from it... it... glimmers with some sort of multicolored, translucent objects... you know you made it big... but you hear something by the front door... the latch starts to raise and you realize you have SECONDS to escape the home or be discovered..."

Aloura panics, the table's in an uproar, "What did she get?!" "You need to get out of there!" "Am I gonna have to break you out of prison during our FIRST game session?" Donia panics and runs, as does the gunslinger who was tagging along but keeping a safe distance. Aloura had left the window open and there was conveniently a table beneath it, for easy escape (I'm not evil, I just like giving my players a hard time). Aloura rolls athletics to get out the window in the few seconds she has before the owner opens the door and finds her inside his home holding...... something. Aloura has advantage, since it's climbing and rolls a Nat1... and a 6 (like I said, she has a dice curse). She clambers up on the table and leaps out the window, somehow avoiding detection by an INSTANT, however, in her hurry to leave, she accidentally kicked a plate that was sitting caddy-corner a stack of dishes. The entire pile came crashing down as the owner of the house opened the door.

Aloura hears the gasp, and the sounds of footfalls as the man runs out onto the street, calling for guards. Aloura hops to the ground and realizes she's been abandoned by her teammates. She dives into a nearby bush and waits. This is the conversation she hears from the road in front of the house:

Owner: Guards, I... I think there's an intruder in my home!

Guard A: Stand back sir, we'll check it out.

Guard B: Did you see anything?

Owner: N-no, but a pile of my things was knocked across the floor upon my entering. Y-you don't think... it was a ghost do you?

Guard A: There doesn't appear to be anyone in this house... Please, come and make sure no valuables were stolen...

Owner: *Brief pause and some sounds of rummaging* N-no... nothing of any value is missing from my house!

Guard B: Then I guess we can roll out an intruder... Next time you open your door, try not to knock all your stuff off your table, eh?

The guards leave and Aloura remains, crouching in a bush, clutching her prize... she looks down. She's holding a small ceramic mug, as she inspects it in the light, small shimmers bounce off of the colored glass pieces affixed to the sides... the mug would GENEROUSLY be worth about 3 coppers... if that...

Aloura meets up with her "partners in crime" back at the local inn and they all stare as she sits, covered in bits of twig and dirt, sipping ale from a small colorful mug.

It's been about 9 sessions in at this point and she still uses that mug religiously for any libations she orders from any tavern.

I have a few more stories but most of them aren't as grand and colorful as my party's first Crit-Fail...

Aloura once was searching a hobgoblin Leutenant's tent for missives from his warchief and walked away with nothing but a raggedy ogre plushy that she cleaned up and now cuddles with every night they sleep. She learned invisibility and spent an entire day (and all her spell slots available) pestering the gunslinger and trying to make him think his room was haunted. She went to the local brothel to see if there were any drunk patrons to pickpocket, little things like that and as a DM, at first, I was a little annoyed by her random antics... but I play heavy with my story and sometimes the party needed the craziness and randomness of Aloura to keep them from getting too serious... and now everyone at the table, myself included, get very excited to hear or see what kind of insanity ensues when Aloura tries to do something...

...She still rolls like she pissed off an elder god... cause I've never seen her roll a Nat20... or anything above 14...