As you are walking through [INSERT ADVENTURING LOCATION HERE], you come across a naked man, sobbing on the side of the road. He is well-groomed and is not magical in any way.
The Story of the Lost Clothes
If the party decides to talk to him, they find out that he was tricked by a local group of miscreants led by a tailor (who also happens to have a magical background) who offered him a breathtaking new outfit. The lord adorned the new threads, but as he traipsed through town during his weekly walkabout in the outskirts, the threads disappeared, leaving him completely naked.
Utterly embarrassed, he ran from the town to this crossroads where he sits before you, standing in a bush to cover himself up (or some such representation).
After learning of how he became so nude, the lord asks you to assist him in one of several ways:
- Double down on the charade, walking him back through town naked and commenting on how great his “threads” look (Deception checks)
- Convince the ne’er-do-wells to apologize publicly, saving face for the lord (Intimidation checks)
- Publicly execute those that tricked the lord (for murderhobos)
- Give him clothes so he can return to town or start a new life elsewhere
- Walk him back through town and convince the populace that being nude is extremely progressive in other parts of the Forgotten Realms. If successful, it could lead to the town turning into a nudist colony. (Persuasion checks)
How your party goes about this is, as always, up to them. A roaming band of murderhobos is likely to go the execution route, while a bardic group may opt for the nudist colony.
The town is largely full of commoners, with a few halflings and the occasional dragonborn. They are simple folk and are easily swayed by who yells the loudest. Charisma checks of 12+ should be enough to get someone to change their mind on just about anything, but you can run this side quest with a higher DC if desired.
Whichever of the routes the party takes, the lord can offer different rewards, but it will largely be sp or gp, or some uncommon wares, as this is by no means a rich and prosperous town.
Possible Twist (if desired)
If you talk with the tailor and bandits you realize they intended to embarrass the lord due to his corruption and recent decisions to deal with a drought. You can get as creative as you want for his misdeeds, or the bandits and tailor can just be awful folks. It all depends on the type of town you’re interested in creating!
RP’ing the Lord
Think King Zog of Disenchantment mixed with Stede Bonnet of Our Flag Means Death. He’s self-obsessed and thinks his title puts him above all others in the town, so his self-esteem is obliterated when everyone laughs at him for walking through town naked. Deep down, he is insecure because a lordship in this town feels meaningless and wants everyone in the town to like him, to levels that disgust some of the townsfolk.