Nayiss Ourobori (Level 20 Tiefling Rogue/Bloodhunter)

Heart of Darkness

Those who look into your eyes can see that you have faced unimaginable horror and that you are no stranger to darkness. Though they might fear you, commoners will extend you every courtesy and do their utmost to help you. Unless you have shown yourself to be a danger to them, they will even take up arms to fight alongside you, should you find yourself facing an enemy alone.

Formerly: Cult of the Dragon Infiltrator. You have infiltrated the ranks of the Cult of the Dragon. Having spied on the organization for quite some time, you are familiar with its inner workings and customs. You have a second identity as an initiate of the cult, enough of a facade to blend in as a simple grunt or servant.

Source of Inspiration

Inspiration Features

Fulfillment Feature: Ender of Legends (Fiends)

Creatures of the fiend creature type have one less Legendary Resistance while they are in combat with you.

Sneak Attack

You know how to strike subtly and exploit a foe's distraction. Once per turn, you can deal an extra 4d6 damage to one creature you hit with an attack if you have Advantage on the attack roll. The attack must use a finesse or a ranged weapon. You don't need Advantage on the attack roll if another enemy of the target is within 5 feet of it, that enemy isn't Incapacitated, and you don't have Disadvantage on the attack roll.

Combat Tactic: Ravager. When you hit a creature while using two-weapon fighting, you can deal your Sneak Attack damage to it, even if you don't meet the normal prerequisites for doing so. If you already do, you flourish instead. You can use this feature 6 times, and you regain all expended uses of it when you finish a long rest.

Thieves' Cant

During your rogue training you learned thieves' cant, a secret mix of dialect, jargon, and code that allows you to hide messages in seemingly normal conversation. Only another creature that knows thieves' cant understands such messages. It takes four times longer to convey such a message than it does to speak the same idea plainly. In addition, you understand a set of secret signs and symbols used to convey short, simple messages, such as whether an area is dangerous or the territory of a thieves' guild, whether loot is nearby, or whether the people in an area are easy marks or will provide a safe house for thieves on the run.

Cunning Action

Your quick thinking and agility allow you to move and act quickly. You can take a Bonus Action on each of your turns in combat. This action can be used only to take the Dash, Disengage, or Hide action.

Cunning Action: Steady Aim. As a Bonus Action, you can give yourself Advantage on your next attack roll on the current turn. You can use this Bonus Action only if you haven't moved during this turn, and after you use the Bonus Action, your speed is 0 until the end of the current turn.

Roguish Expertise

Sleight of Hand: Quick Frisk. You gain expertise with Sleight of Hand. As an Action, make a Sleight of Hand (Dexterity) check with a DC equal to the passive Perception (Wisdom) score of a target you can touch. On a success, you learn what types of objects they are carrying. If they are carrying coins, you know the approximate number. For the next 24 hours, any Sleight of Hand checks you make against the target have Advantage. If you do not exceed the DC by 5, the creature knows you frisked it. Once you use this ability, you cannot do so again until you finish a short or long rest.

Deception: Walk it Back. You gain expertise in Deception. When an ally fails a Deception check to tell a lie, you can use your Reaction to add a supporting detail, using your bonus to Deception checks instead of theirs. After you use this ability, you cannot do so again until you finish a short or long rest.

Acrobatics: Aerobatics. You gain expertise in Acrobatics. Opportunity attacks made against you by a creature whose space you move through have Disadvantage. Additionally, when you take the Tumble bonus action and exceed the DC by 5 or more, you may get your Bonus Action back. When you do, you cannot do so again until you finish a short or long rest.

Persuasion: Roguish Charm. You gain expertise with Persuasion. If you spend 1 minute talking to a creature who can understand what you say, and if that creature is not hostile, you may make a Charisma (Persuasion) check with a DC equal to the creature’s passive Wisdom (Insight) score. On a success, the creature is non magically Charmed by you for 1 hour. The charm ends early if you or your allies harm the creature. Once you’ve used this feature successfully, you can’t use it again until you finish a long rest.

Self-Preservation

Your honed reflexes and mental toughness allow you to avoid danger.

• Evasion. When you make a Dexterity saving throw against an effect that deals half damage on a success, you take no damage on a success and half damage on a failure.
• Uncanny Dodge. When you are hit by an attacker that you can see, you can use your Reaction to halve the damage from the attack.

Improved Critical

Your attacks with finesse and ranged weapons score a critical hit on a roll of 19 or 20.

Hunter's Bane (Charisma)

You have survived the Hunter’s Bane, a dangerous, long-guarded ritual that alters your life’s blood, forever binding you to the darkness and honing your senses against it. You have Advantage on Wisdom (Survival) checks to track dragons, fiends, or undead, as well as on Intelligence ability checks to recall information about them.

Blood Maledict (2/rest)

You gain the ability to channel, and sometimes sacrifice, a part of your vital essence to curse and manipulate creatures through hemocraft magic. When you use your Blood Maledict, you choose which curse to invoke. While invoking a blood curse, but before it affects the target, you can choose to amplify the curse by losing a number of hit points equal to one roll of your hemocraft die. An amplified curse gains an additional effect, noted in the curse’s description. Creatures that do not have blood in their bodies are immune to blood curses, unless you have amplified the curse.

• Blood Curse of the Fallen Puppet. When a creature you can see within 30 feet of you drops to 0 hit points, you can use your Reaction to give that creature a final act of aggression. That creature immediately makes a single weapon attack against a target of your choice within its attack range. Amplify. You can first move the cursed creature up to half their speed, and you grant a bonus +5 to the cursed creature's attack roll.
• Blood Curse of the Marked. As a Bonus Action, you mark a creature that you can see within 30 feet of you. Until the end of your turn, whenever you hit the cursed creature with a weapon for which you have an active crimson rite, you roll an additional hemocraft die when determining the extra damage from the rite. Amplify. The benefits of this curse last for 1 minute, or until you end your turn without damaging the creature with your Crimson Rite feature.
• Blood Curse of Transfusion. As a Bonus Action, you can curse your own vitality, tearing some of it forth and transferring it to an ally in need. You take 3d6 necrotic damage, and a living creature you choose within 30 feet of you regains a number of hit points equal to that amount plus 5. This damage increases to 4d6 at 17th level. Amplify. Your target regains hit points equal to twice the necrotic damage you took, including the damage taken from amplifying this curse, plus 5.

Fighting Style: Mariner

As long as you are not wearing heavy armor or using a shield, you have a swimming speed and a climbing speed equal to your normal speed. For each of these speeds you already have, your walking speed increases by 5 feet instead.

Crimson Rite (1d8)

You learn to invoke a rite of hemocraft that infuses your weapon strikes with elemental energy. As a Bonus Action, you can activate any rite you know on one weapon you're holding. The effect of the rite lasts until you finish a short or long rest. When you activate a rite, you take necrotic damage equal to one roll of your hemocraft die. This damage can't be reduced in any way. While the rite is in effect, attacks you make with this weapon deal extra damage equal to your hemocraft die of the type determined by the chosen rite. A weapon can hold only one active rite at a time. Other creatures can't gain the benefit of your rite.

• Rite of the Storm. Your rite damage is lightning damage.
• Rite of the Tarnished. Your rite damage is acid damage.

Stigmata

Few who undergo the rituals to join a Bloodhunter order survive–those who do come back changed in some way.

• Uncanny Valley. While it may not be obvious at first glance, something is off about you; perhaps you are a little too beautiful. While a creature can see you, it has Advantage on Wisdom (Perception) checks and Intelligence (Investigation) checks against you, but Disadvantage on Wisdom (Insight) checks against you. A creature immune to the Charmed condition is immune to this effect.
• Profane Cicatrix: Fiends (Ritual Scarring). You bear an otherworldly scar from the outer planes–evidence of your tampering with dark powers. When you make an Intelligence check to recall information about fiends, you have expertise in the check. Additionally, you know when a fiend is within 120 feet of you, as your stigmata burns.

Extra Attack

You can attack twice, instead of once, whenever you take the Attack action on your turn.

Brand of Castigation (1/rest)

Whenever you damage a creature with your Crimson Rite feature, you can choose to sear an arcane brand of hemocraft magic into it (requires no action). You always know the direction to the branded creature, and each time the branded creature deals damage to you or a creature you can see within 5 feet of you, the creature takes 5 psychic damage.

Your brand lasts until you dismiss it, or you apply a brand to another creature. Your brand counts as a spell for the purposes of dispel magic, and the spell level is equal to half of your blood hunter level (maximum of 9th level spell).

Once you use this feature, you can’t use it again until you finish a short or long rest.

Hunter's Moon

Your exposure to the dark side of both monster and man has caused your nights to be plagued with nightmares that wax with the moon’s cycles.

• Hallucination of Bloody Murder. Scenes of gratuitous violence plague your nights, quickening your pace at the sight of blood. When you reduce a hostile creature to 0 hit points, you gain temporary hit points equal to a roll of your hemocraft die + half your Bloodhunter level. You cannot willingly spare a creature when you reduce it to 0 hit points with a melee attack unless you spend a Flourish to do so.
• Incubus of Wanton Satisfaction (New Moon). At night, your mind swims with carnal pleasure and taboo that would give a fiend pause. You are immune to the Charmed condition. When you recover hit dice during a long rest, you must partake in hedonistic excess in the process (such as by consuming fancy food and drink, or through an Aristocratic lifestyle expense) or suffer 1 stress at the end of the long rest or you recover no hit dice.

Dark Augmentation

Arcane blood magic suffuses your body, permanently reinforcing your resilience. Your speed increases by 5 feet, and whenever you make a Strength, Dexterity, or Constitution saving throw, you gain a +5 bonus to the saving throw.

Scout Leader (Rogue)

When your party makes a group Stealth check, you may apply your result to yourself and one ally after seeing the results of all rolls. Additionally, when you are traveling, you and up to 12 allies can move stealthily at a normal pace.

Cunning Action: Fast Hands (Rogue)

You can use a Bonus Action to make a Dexterity (Sleight of Hand) check, use your thieves' tools to disarm a trap or open a lock, or take the Use an Object action.

Second Story Work (Rogue)

You gain a climbing speed equal to your movement speed. In addition, you use your Dexterity score when determining your jump distance or when taking the Jump action.

Skulker (Rogue)

You can try to hide when you are lightly obscured from the creature from which you are hiding.

Blood Tithe (Bloodhunter)

When you make an ability check, you can use your Reaction to use your blood magic to enhance your mind and body. You lose a number of hit points equal to one roll of your hemocraft die, and add that amount to the check.

Fiendish Vigor (Warlock)

You can cast false life on yourself at will without spending mana or material components. When cast out of combat, you always gain 8 temporary hit points.

Ghostly Gaze (Bloodhunter)

As an Action, you gain the ability to see through solid objects to a range of 30 feet. Within that range, you have darkvision if you don’t already have it. This special sight lasts for 1 minute or until your concentration ends (as if you were concentrating on a spell). During that time, you perceive objects as ghostly, transparent images.

Once you use this invocation, you can’t use it again until you finish a short or long rest.

Gift of the Depths (Bloodhunter)

You can breathe underwater, and you gain a swimming speed equal to your walking speed.

You can also cast water breathing without spending mana. You regain the ability to do so when you finish a long rest.

Grim Psychometry (Bloodhunter)

When making an Intelligence (History) check to recall information about a darker past surrounding an object you are touching, or a location you are present in, you have Advantage on the roll. The information gleaned often leans towards the more sinister influences of the past, and sometimes conveys visions of things previously unknown to the character on higher rolls.

New Moon (Bloodhunter)

Choose a second option from the Hunter’s Moon class feature. You gain the benefits and detriments from it.

Noxious Invigoration (Warlock)

Whenever you gain temporary hit points, increase the amount you gain by 6.

Ritual Scarring (Bloodhunter)

Choose a second option from the Stigmata class feature. You gain the benefits and detriments from it.

Mage Hunter (Skill Expert: Sorcerer)

When tracking a creature that can cast at least one spell, you can attempt to do so by focusing on the mystic energy it leaves in its wake, allowing you to use your Charisma for any ability checks made to track it.

Devil's Sight (Eldritch Adept: Warlock)

You can see normally in darkness, both magical and nonmagical, to a distance of 120 feet.

Master of Myriad Forms (Eldritch Adept: Warlock)

As an Action, you change your appearance and your voice. You determine the specifics of the changes, including your coloration, hair length, and sex. You can also adjust your height between Medium and Small. You can make yourself appear as a member of another race, though none of your game statistics change. You can't duplicate the appearance of a creature you've never seen. You can add vestigial horns, tails, wings or other features, or remove existing ones, but you cannot benefit from their game effects if you do not have them. For example, a creature with natural wings who removes them with this spell loses its fly speed. You can also add or remove arms, legs, and other functional appendages, but you can never add more arms or legs than is normal for your ancestry. Your clothing and equipment aren't changed by this trait.

You stay in the new form until you use an Action to revert to your true form or until you die.

Stygian Spite (Ascendant) | Hand Crossbow (Attunement II)

You gain a +3 bonus to attack and damage rolls made with this magic weapon. On a hit, the weapon deals an extra 3d6 acid damage.

• Whenever you roll a critical hit on your attack roll with this weapon, each creature of your choice within 5 feet of the target takes 5 acid damage.
• As an Action, you can unleash a 60-foot cone of destructive energy from the weapon. Each creature in that area must make a DC 18 Dexterity saving throw, taking 12d6 acid damage on a failed save, or half as much damage on a successful one. Once this action is used, it can't be used again until the next dawn.

Darklight | Hand Crossbow

You have a +1 bonus to the attack rolls and damage rolls you make with this magic weapon. This crossbow gets warm in the presence of celestials.

• The normal and long range of this weapon are doubled.

Demon Cannon
This unique crossbow has replaced its string firing mechanism with a single tube inscribed with Abyssal runes. When you make a critical hit with this magical weapon against a target, you may choose for your aummunition to burst, creating a 5-foot wide, 60-foot long line of dark energy behind your target that forces all creatures caught in it to make a DC 16 Dexterity saving throw. On a failure, a target takes 4d10 force damage, or half as much damage on a success.

Lash of Shadows (Exalted) | Whip (Attunement II)

This snakeskin whip ends in five animated serpent heads.

Sentience. The Lash of Shadows is a sentient chaotic evil weapon with an Intelligence of 18, a Wisdom of 16, and a Charisma of 20. It has hearing and darkvision out to a range of 120 feet. The weapon speaks through the serpent heads and can speak, read, and understand Abyssal, Common, and Draconic. A mad marilith named Sizlifeth is trapped within the Lash of Shadows.

You gain a +3 bonus to attack and damage rolls made with this magic weapon. When attuned to it, you gain the following benefits:

• You can speak, read, and write Abyssal and Draconic.
• You can attempt to poison any creature that is hit by the whip. The creature must succeed on a DC 17 Constitution saving throw or suffer the effect of one of the following poisons of your choice; once a poison other than Serpent Venom has been used, that poison can't be used again until the next dawn:
  • Serpent Venom. A creature that fails the saving throw against this poison takes 3d6 poison damage, or half as much damage on a successful save.
  • Dead Eyes. A creature that fails the saving throw against this poison is Poisoned for 1 hour. While Poisoned in this way, the creature is Blinded.
  • Ghoul's Blood. A creature that fails the saving throw against this poison is Poisoned for 1 minute. While Poisoned in this way, the creature is Paralyzed. The creature can repeat the saving throw at the end of each of its turns, ending the effect on itself on a success.
  • Cockatrice Tears. A creature that fails the saving throw against this poison begins to turn to stone and is Restrained. It must repeat the saving throw at the end of its next turn. On a success, the effect ends. On a failure, the creature is Petrified for 24 hours.
  • Special: Sizlifeth can dispense any of the above poisons freely to Nayiss, without requiring attunement. They follow the same restrictions as above, and can be further enhanced by Nayiss's abilities or turned into affliction poisons. Any poison other than Serpent Venom that has doses that have not been used becomes inert after 24 hours.

Studded Leather Armor of Acid Resistance (Attunement I)

You have resistance to acid damage while you wear this armor.

Boots of Elvenkind

While you wear these boots, your steps make no sound, regardless of the surface you are moving across. You also have Advantage on Stealth checks that rely on moving silently.

Crown of Darkness (Attunement I)

This crown has 9 charges. While wearing and attuned to this crown, and so long as you are not in bright light, you may spend an Action to expend 1 or more of the crown's charges to cast one of the following spells from it, with Charisma as your spellcasting modifier: conjure animals (3 charges and may only summon creatures of the night), darkness (2 charges), invisibility (2 charges, plus 1 additional charge for every level above 2nd), spider climb (2 charges), gaseous form (3 charges), vampiric touch (3 charges, plus 1 additional charge for every level above 3rd).

The crown recovers 1d8 + 1 charges at midnight. While wearing and attuned to the crown, you also gain Advantage on any Stealth checks to hide in dim light or darkness, and darkvision out to 60 feet. If you already have darkvision from another source, its range increases by 30 feet.

Amulet of Proof against Detection and Location (Attunement I)

While wearing this amulet, you are hidden from divination magic. You can't be targeted by such magic or perceived through magical scrying sensors.

Necklace of Adaptation (Attunement I)

While wearing this necklace, you can breathe normally in any environment, and you have Advantage on saving throws made against harmful gases and vapors.

Ring of Warmth (Attunement I)

While wearing this ring, you have resistance to cold damage. In addition, you and everything you wear and carry are unharmed by temperatures as low as -50 degrees Fahrenheit.

Smoke of Insight

This magical, hand-held smoke does not require tobacco and emits a pleasant aroma and harmless smoke when smoked. It has a calming effect on the smoker.

It has 3 charges. As an Action, you can expend 1 charge and smoke the item to get Advantage on the next Wisdom check or Wisdom saving throw you make in the next minute. The item regains 1d3 charges at dawn.