Legendary Grinning Herald

Whether wearing a mortal guise or in its true form the first thing one notices about a grinning herald is its smile. When pretending to be a fleeting thing the fey's grin is warm, charming, almost entrancing. When showing its true colors the herald’s mouth stretches painfully wide, its pearly teeth large, flat, but holding a cleaver's edge. The fey has corpse-gray skin pulled thin over its bony body and jet-black eyes within sunken sockets. Even in its horrid form, the fey is beguiling in its intensity. Their barrel chests don’t match the rest of their scarecrow physique..

Blind Fury. Blinded after daring to spy on the Lord of Invisible Blades while the archfey was bathing, Holloweyes’ isn’t an apt description for this grinning herald, though. His sockets aren’t empty but filled with direfly hives that stretch deep into his body without doing a lick of harm. When in human form, though, the illusion of empty holes settles in that he covers with a blindfold. Holloweyes has taken this maiming in stride and even learned to master blindness as a weapon to use against others. Through magical means he robs them of sight temporarily. He has also made an ally of the foul insects within him, the swarm serving as a familiar or a stop-gap attack when he empties them all out of his skull.

Holloweyes

Medium Fey, lawful evil

Armor Class 14

Hit Points 135 (18d8 + 54)

Speed 30ft

Str 12 Dex 18 Con 16 Int 16 Wis 14 Cha 19

Saves Con +6 Cha +7

SkillsDeception +7, Perception +5, Persuasion +7

Condition Immunities blinded charmed

Damage Resistances lighting, thunder, bludgeoning, piercing, and slashing from nonmagical attacks that aren't silver

Senses blindsight 60 ft. (blind beyond this radius), passive Perception 15

Languages sylvan, all humanoid.

Challenge 6 (2,300 XP)

Direfly Nest.

Holloweyes has a swarm of direflies as a familiar. The swarm gains all the benefits of being a familiar as per the spell Find Familiar. In addition, the swarm can enter the feys's square and enter its body, gaining full cover when doing so. If the swarm is reduced to 0 hit points it can be resummoned by Holloweyes after a short rest.

Magic Resistances:

The Grinning Herald has advantage on saving throws against spells or other magical effects.

Innate Spellcasting:

The Grinning Herald's spellcasting ability is Charisma (spell save DC 15). The Grinning Herald can innately cast the following spells, requiring no material components:

At Will: Bane, Bless, Chaos Bolt, Charm Person

2/day each: Crown of Madness, Heroism, Plane Shift (self only)

Actions

Bite.

Melee Weapon Attack: +7 to hit, reach 5ft., one target. Hit: 9 (1d10+4) slashing damage.

Direfly Sting

Direfly Sting. Ranged Weapon Attack: +7 to hit, reach 30/60 ft., one target. Hit: 15 (2d10+4) psychic damage.

Change Shape.

The creature magically polymorphs into a Small or Medium humanoid, or back to its true form. Its statistics are the same in each form. Any equipment it is wearing or carrying isn't transformed. It reverts back to its true form if it dies or uses its bite attack.

Horn of Marrow (Recharge 5-6).

The Grinning Herald ushers a bone-jarring bellow in a 15-ft cone. Each creature in the cone must make a DC 14 Dexterity saving throw, taking 24 (7d6) thunder damage and is pushed 10ft away from the Grinning Herald on a failed save before falling prone. On success the creature takes half as much damage, is not pushed back and does not fall prone.

Reactions

Hollow Eyes can take 3 legendary actions, choosing from the options below. Only one legendary action option can be used at a time and only at the end of another creature's turn. Holloweyes regains spent legendary actions at the start of its turn.

Bite (1 point).

Holloweyes makes a bite attack.

Consume Sight (1 Point).

Hollow eyes targets a creature it can see within 60ft and assaults its eyes with direflies. The creature must succeed on a DC 14 Consitution save or be Blinded until the end of its next turn.

Outpour (2 points).

Holloweyes empties his body of direflies. All creatures within 10ft of the fey must suceed on a DC 15 Charisma save or take 11 (2d10) psychic damage. Holloweyes cannot move on his next turn as the direflies flow back into him.