Hi there, adventurino! Remember Part One of this piece, when I gave you that primer on the mysterious non-person known as Bob? Well, here is part two of that magnum opus of awkward nothingness, with as much closure as I have deemed useful when creating a walking bag of holding.

Back we go to the body of Bottomless Bob, a hapless human who had a habit of collecting things that send players on wild goose chases, probably because they deserve it.

We left off half-way through digging around in his coat. Should you wish to taunt your looters more, feel free to spread the coat's contents across several items like scarves with pockets on the ends, bandoliers, and so forth.

The whole idea is to take the process of digging around in a dead body, easily one of the creepiest processes in this game, and make it a process loaded with ennui. So remember you can add all of this loot onto a deceased character already in your campaign, for Bob is but a cipher for an ironic statement about the folly of greed and scavenging. 

Are you and your group too mature for such folly? Cool, then hopefully someone else in your group will find this article and sneak something in from it just to mess with you. Because that sounds like a super stuffy stance to take.

Right-hand Coat Pockets

1. Thimbles of Toril: Bob used to sail the seas more often in his sailor salad days, and in his pockets he has dozens of collectible ceramic thimbles, each inscribed with the location of a different town. All are scuffed, some are broken, none will be of interest to pawnbrokers. Use whatever resources you can for a complete list of D&D cities, because they’re all pretty much there. It was incredibly tempting to list as many here as I could, each with a little regional mascot on them, but I believe I am already breaking the record for most bullets in a Dungeons and Dragons article. The Waterdeep one should have a little Pink Flumph on it though.

2. Sewing Kit: Bob has a sewing kit with a bent needle and an empty spool of string, as he regularly patched his clothes. Hence the thimbles for protecting his dainty fingertips. By the time you get to it, it is useless. The thread is frayed and molded together from sweat. Also, do a DC 10 Dexterity check to make sure you don't prick your finger on the sewing needle for one point of damage. Oh, and if you fail, you also have to do a DC 5 Constitution Saving throw or else develop a disease called moth rot, a mold that develops in the underarms of unwashed moths. A standard healing spell can get rid of it, but if one is not cast soon the creature will develop an unholy stink like that of a fever-soaked pillow left on a plague victim's bed for a week, causing a -2 to all Charisma based checks.

3. Library of Notes: The sixth inner-most pocket of Bob’s coat contains many notes, and they are mixed together with one mysterious torn up note. This torn up note takes two hours to sort out of the pile of notes and piece back together. It reads “I want a spicy sandwich” written three times in three different languages: Abyssal, Celestial, and Deep Speech. To individuals who cannot read these languages, it appears as indecipherable code, and they will need to quest for three different characters to translate one of the three lines and get a sense of its meaninglessness. Bob was merely practicing penmanship and trying to learn a language that would get him into a nearby tavern full of dangerous-looking attractive people. He had no secret plan other than getting to hang out with them because they looked cool. The other individual notes that are jumbled up with the torn up "spicy sandwich" note all read simple mundane things, and prolonged sorting reveals only:  

   Buy pumpkins

   You are the captain of the ship of YOU

   Cry less

   Look for friends for fishing tripz

   Mondays!

   Smile good get date

   Eat greens or get sad tummy

   Drink at tough-looking place

    

Downstairs Parts 

1. Stone Rat Non-Purse: Bob once tried to have a coin purse enchanted to be a coin purse of holding, but the enchanter was senile and botched multiple spells trying to make it happen. Bob kept the resulting strange purse in the hope he could one day figure out how to salvage its magic, though the sad fact is you can't salvage magic from a weird purse. This small pouch does have more space inside than it would appear, but it contains 30 rats, most completely turned to stone as the enchanter panicked and tried to stop them from attacking him, overstuffing the purse to the brim. Any rough experimentation, even the slightest attempt to ease a rat out, will cause the purse to rip and the weak enchantment to end, expelling the contents everywhere at a high rate of speed and causing 1d4 points of bludgeoning damage as the holder is pummeled by 27 stone rats and 3 rat skeletons.
2. Bent Non-Copper: Though penniless, Bob regularly attempted to counterfeit. As a result his actual, non-magical coin purse contains the equivalent 5 gold, but it is all in bent or otherwise ruined fake copper pieces. To realize the whole pouch’s coins are worthless takes an hour and the DC Investigation check is only 5.
3. Enchanted Irony Belt: Bob was planning on teaching a lesson to an ex-girlfriend named Doris later that evening, but it turns out he was given bad information and Doris has since moved across the continent, having long forgotten Bob. However, touching Bob’s belt sets off a magic spell that was meant to embarrass and confuse Doris. In typical Bob fashion, the enchantment is cheap and unreliable. In a puff of grey smoke, the belt transforms into three hand-sized spiders, each with a tiny glass vial for a thorax, a tiny but visible note rolled up and bound with string inside of each glass vial. The spiders are harmless, but attempt to skitter away, and each can only be caught with a DC 15 Athletics check. After a failure each spider will continue to scurry about for 5 more minutes before an attempt can be made again. The notes have numbers and words on them, and if all four spiders are captured they reveal:
   

   1) DORIS I

   2) NEVER

   3) LOVED
   

   There was intended to be a fourth that said “you” but due to hubristically bad magic (bet you saw that coming) that fourth vial-spider never materializes. At the moment the belt transforms, Bob’s body will also instantly teleport 50 feet away to an unoccupied space, clumping limply to the ground. The teleportation spell was intended to go off while Bob was undressing, leaving a passive-aggressive note that is difficult to piece together, and letting Bob out of their presumed uncomfortable situation and into a room at a nearby inn. Bob died before he could discover that he was set up, and that this old flame was never going to show. It is impossible for this scenario to be completely put together by logic, but if someone wants to try the Dungeon Master can say any of the above while shrugging hopelessly, as if to imply such things are simply lost in the sands of time.
4. Ring of Not-So-Assorted Keys: Bob has a ring of 23 keys, but an investigation or insight check with a difficulty of 10 reveals that, despite them looking different and first and some being made to have a look of grandeur, they all fit the same lock. He went to locksmiths in different port towns, and none will know the mystery other than recognizing a description of Bob with a DC 18 Charisma check. The lock the keys fit is for the door to Bob’s outhouse. Players who do not quest for Bob’s house, find Bob in his house and search outside, or otherwise investigate the outhouse will never learn of its existence.
5. Diary of a Limpy Boot: Years ago Bob used to cheat at cards, but gave it up when he moved to this town. He kept up the habit of stashing playing cards in his boots though, and he developed a habit of rubbing the inscription off of one side and writing a daily diary entry on each card. There are nearly 100 playing cards mashed into his boots, each describing a different day of his unexciting life. Mostly they read thusly: 

   Cleaned teeth. Went to old market. Remembered to smile. Showed off the hat. Drank whiskey. Goodnight.

   Every once in a while, there is mention of him showing off his jewelry or wooden knives, but it never results in drama. Only, at most, a short description of the uneventful act:

   Showed knives to guy.

   Players and Dungeon Masters should attempt to improvise slight variations if other players want to know what each says. Some can be written in Abyssal, Celestial, or Deep Speech rather than Common, some in an extra flourishing handwriting, but the content never deviates much.
6. Extended Notes Library: Here are more notes written in Common, in Bob’s careful hand, sloppily filling the pockets of his pants:

Get better wig

Doris!

Whiskey

Need less time on boats, too wavy

Why Doris, why?

Don’t trust old enchanter, keeps making accidental rats

Beef

Time to lean? Time to clean. But don’t be mean or make a scene. Keep yard green. Ouch, my spleen!

No-one in the current town will remember Bob without a DC 22 Charisma check, and even then, they will only remember a skinny, middle-aged, wanna-be sailor who looked grubby and odd. The elderly enchanter lived beneath a bridge and has passed away, and no trace of him can be found other than 2 stone rats beneath a bridge nearby.

Doris can be found if a long, meandering quest is made to another city. It is unlikely a player will choose this based solely on the passing mentions of her name in a note, so the Dungeon Master is encouraged to make a note and tie her existence in should the party ever travel a great distance. Doris is now a successful vigilante buccaneer, and will require that same difficult and vague charisma check. The only thing she will be able to add from her perspective is that yes, she went on a few dates with Bob, and that he sucked at cards. Any mention of the spiders, his possessions, or anything else about him will simply cause Doris to get a far away look in her eye and say, "Excuse me, but... why were you picking through his dead body again?"

Well, this was one of the weirdest things I've ever written for D&D, but I had a lot of fun putting it together. I could have just made this a weird footnote in another less bizarre piece, or an addendum on a more normal-seeming chunk of lore but I wanted to put it here so I could narrate it and make it amusing too. I hope you find ways to squeeze this insanity into your own game, because everyone loves loot, but nobody considers the ennui quite as much as Bob might insist.

 Dan Telfer is the Dungeons Humorist aka Comedy Archmage for D&D Beyond (a fun way they are letting him say "writer"), dungeon master for the Nerd Poker podcast, a stand-up comedian, a TV writer who also helped win some Emmys over at Comedy Central, and a former editor of MAD Magazine and The Onion. He can be found riding his bike around Los Angeles from gig to gig to gaming store, though the best way to find out what he's up to is to follow him on Twitter via @dantelfer.