The Grim Tickler is from the Island of Perpetual Tickling. He only appears in Esther… The Girl Who Became Queen. He is known across the land of Persia as the officer of one of the most dreaded punishments to ever exist: banishment to the Island of Perpetual Tickling.
From top to bottom the character wears a dark brown robe that is so long it drags to the floor, giving him a Grim Reaper look. His hood is down and covers most of his face, but those who look closely will only see the body of a slender & green vegetable with a nose. Tan stitches hold the coat together near the neck of the robe, keeping the wearer tightly concealed and ever so menacing. This punisher's choice of torment is a huge, soft white feather. This one seems different from anything else you'd ever see in terms of feathers, since this feather seems to hold the ability of easily tickling anyone it comes in contact with through their clothes. The Grim Tickler also seems to have the ability to summon extremely eerie organ music whenever he opens a door, and a boost in power being able to bust any door open with some serious force. I'm guessing those trained to be Grim Ticklers get extra protein during training.
In terms of personality, the Grim Tickler shows no emotion as he mercilessly tickles his victims out the door and right to the Island of Perpetual Tickling. Gotta wonder how much these guys get paid to do this, what are the hours of each shift, and what is their life like outside "work". A theory is shown in this video https://www.youtube.com/watch?v=idcLkXULl58
As far we know anything, Grim Ticklers are cold-blooded tormentors who will never stop the ticklish torment for anything. Not for tears of laughter, not for agonizing screams to end the pain of laughter, and not for the endless begging and crying that ensues when prisoners are broken on the inside and out. The Grim Ticklers will not stop until their victims stop moving, dead from laughter. The deceased are removed, and more room is made for the next victims of the island's eternal torment.
The layout of the island could be many things. It could be just an island where you run through the forest to escape Grim Ticklers scattered throughout the island, never being safe day and night as they always know where you are. The island could hold a prison, where prisoners are chained to the walls to serve their everlasting punishment in front of a feather. For all we know, the tickling is just for show and prisoners are actually brutally slaughtered behind closed doors, loved ones never being able to see those who were banished ever again.
Must be interesting to know what it's like to see such horrors carried out by something enjoyable. To see the eyes of prisoners who will die with smiles on their faces. To hear their last words choked by screams of inescapable torment. To know that you will join the dead whose bones still rattle with giggles from Hell.