Sir Amelio Ferretti
Dossier file on Cell Knight Sir Amelio Ferretti AKA the Whipmaster. Contains elements from TES IV Oblivion.
Filename: Sir. Amelio Ferretti
Morphology: Standard Human
Race: Imperial Briton
Sex: Male
Current Age: 32
Occupation: Head Jailer and Torturer
Current Residence: Castle Skingrad
Faction/s: County Skingrad Guard
Background: Sir. Amelio Ferretti was born in County Anvil to parents who's identities have yet to be determined. The parents appear to have taken steps to disavow this individual due to being a deviant. He is a very reclusive individual so getting information on him has proven difficult.
What we were able to dig up was that when he was 10, he witnessed the whipping of a thief and that was when his deviancy manifested itself. By age 13 Amelio began to express interest in being a guard at the Anvil Castle Dungeon. His parents thought this was odd but didn't suspect anything devious.
He got the job at age 20 but was fired when one of the other guards discovered his deviant behavior. When his parents learned about this, they sent him into exile and took steps to disavow him. Amelio then made his way to County Skingrad and applied for a job there. The Count of Skingrad who is suspected for being a vampire though this has not been confirmed, gave him the job of being the head jailer of the castle dungeon after the previous one left the county for unknown reasons.
Ever since he took the job, the sound of whips cracking could be heard coming from the dungeon followed by screams. When other guards went down to check, prisoners were discovered have their backs reduced to a bloody mess of cuts and welts. It has been determined that some of them have died as a result of this. After preventing a group of prisoners from escaping, Amelio was knighted by the count however he was not granted any land and just lives in the castle.
Current Status: Sir. Amelio performs his duties wearing a suit of plate armor with a
visored helmet. When it comes time to interrogate a prisoner, he will
have it taken to a torture chamber and he follows carrying an 8 foot
bullwhip. What exactly happens next remained unknown until one of our
sources inside the Jailers provided us with details of an interrogation
of a captured bandit.
According to our source, Sir Amelio had the bandit chained to a stone pillar and his bare back exposed. As he was questioned about the location of his leader, Amelio would crack the bullwhip on his back in three lash intervals. He wielded the whip in a was that suggests that he must practiced whipping people for at least three years. It didn't take long for the bandit to start bleeding. It was after 6 lashes.
Sir Amelio's whipping technique involves making sure each lash is given in the opposite direction in order to make the whip marks criss-cross over each other. The bandit started screaming at around the 30th lash. It was noted by our source that Sir Amelio appeared to take some sort of sadistic enjoyment in whipping the bandit. It took three separate sessions of 100 lashes each to finally get the location of the bandit lair out of him. By that time his back looked like that of a rebellious slave.
Our source also revealed that Sir Amelio would frequently whip other prisoners in order to "keep them under control". However he would sometime lose control and accidentally kill some of them.
Addendum 01: Apparently the report by our source got leaked out to the public somehow. Because of this Sir Amelio has been nicknamed the "Whipmaster" by the public and the guards. The threat of being at the whipmaster's tender mercies appeared to deter a significant amount of crime in the county. So the Count doesn't seem to mind that a few prisoners get whipped to death every once in awhile.
Addendum 02: After further examination of Sir Amelio's behavior and the fact that his own family considers him a "deviant", we conclude that this man has some kind of Sexual Sadism mental disorder. It is recommended that he be removed from his position as Head Jailer and committed to an insane asylum.
Addendum 03: Following some "persuasion", we managed to secure an interview with Sir Amelio himself. What he revealed was...interesting.
First off, he confirmed the information we collected in this file except for the mental disorder addendum. Which is not surprising since crazy people don't realize they are crazy. He has forgotten the names of his parents and has no wish to remember due to being disowned by them after his..."interest" in flagellation was discovered. So uncovering his roots has practically hit a dead end. When pressed further on this "interest" we got some very interesting details.
Apparently he is unable to experience any "pleasure" without the lash. (No wonder he was disowned. Who on earth would want to hook up with him except for cultists who worship evil deities?) He showed us his favorite whip and gave us a demonstration. After washing the blood splatters off of ourselves we asked him why he always wears that helmet on the job. He said that it was so that prisoners cannot identify him as he knows his cruelty might get him onto a hit list if someone were to recognize him. Considering what we just saw, his paranoia seems justified.
Sir Amelio is not fond of the nickname "Whipmaster" though as it makes him sound like a slaver. He has asked us if we could identify the person who leaked out the report. However we have no idea who that person might be due to the complete lack of clues. His resulting infamy makes him nervous that some other knightly orders might decide to go after him if there is not already at least one that is hunting him down. We currently do not know of any knightly orders that would want him taken out.
When we asked him if there was any other job he would be willing to accept, he responded that as long as he got to whip people, he would take it.
Addendum 04: It has come to our attention that he has gone with a group of adventurers on a quest to escort an Agony Demon to The Ethereal Delves. It seems that there is a portal that only this demon can open that can be found in a hidden chamber somewhere in those ancient tunnels. Supposedly he is only there to keep the demon fed by whipping it.
End of line.
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? Responses (2)

I would like to offer some advice.
Appearance - we know nothing about what this guy looks like. No visual cues, no personality clues, nothing to guide me on how I would use him as an NPC outside of a dungeon.
Backstory is pretty good, he's been obsessed with whipping people since he was a teen. What I don't know is how much do people know about this, do they know that he carries out his job in a sadistic manner, or is it just a guy doing his job, and maybe if people didn't want to get lashes, they wouldnt do no crime. Is the whip his one true love, does he have a family? Was there any compensation with his title or is he a landless knight, a member of the gentry?
Another question I have relates to the nature of the NPC. Does his enthusiasm for whipping come from a sadistic desire to cause pain, or is it rooted in a brutal discplinarianism?

I added two addendum to this post. Hope this helps.