Mistress of the Web (Variant Rogue)

The dark elves are a race of cunning, manipulative creatures made all the more so by their ruthless upbringing. Some drow rogues, however, are exceptionally devious, honing their talent for scheming into a weapon of incredible potency. Some are well known and others are whispers only spoken of in the highest circles, but all are masters of first-hand knowledge in the Underworld. These clever drow run crime syndicates, hold courts of nobles in their grasp, and are the masters of felonious goods and services wherever they dwell. While these beings are mostly known as Mistresses of the Web due to females tending to have the dominant positions in drow society, it is not wholly unknown for males to follow this profession.

In the tongue of the drow, people with this calling are also known as drulaiak’thekwar—which roughly translates to “mistress of honeyed words laced with poison.”

Creating a Mistress of the Web

As you create your mistress of the web character, consider the character’s relationship with the byzantine power structures and constantly changing “laws” of the chaotic drow society. Did you have run-ins with the powers-that-be? Did you own slaves? Why have you taken up adventuring? Has your syndicate been squashed or did you need to escape drow lands? What was the trigger that made you abandon the cutthroat society? If you are a drow, what’s your social status before and after taking up adventuring? If you are not a drow, how did you take up this profession? Perhaps you were raised by drow or never saw eye to eye with the ruling caste, the priests or other powerful forces. How do you approach non-drow and other races? Perhaps you are an elitist, manipulating them without regret, or perhaps you wanted to use your talents for means not afforded by drow society.

Quick Build

You can make a mistress of the web quickly by following these suggestions: First, Charisma should be your highest ability score, followed by Dexterity if you plan to emphasize stealth and infiltration, Intelligence if you want to play a character more akin to an investigator.

Second, choose the charlatan background.

Hit Points

Hit Dice: 1d8 per mistress of the web level
Hit Points at 1st Level: 8 + your Constitution modifier
Hit Points at Higher Levels: 1d8 (or 5) + your Constitution modifier per mistress of the web level after 1st


Armor: Light Armor
Weapons: Simple weapons, hand crossbows, longswords, rapiers, shortswords
Tools: Thieves’ Tools
Saving Throws: Dexterity, Charisma
Skills: Choose four from Acrobatics, Athletics, Insight, Intimidation, Investigation, Perception, Performance, Sleight of Hand and Stealth


You start with the following equipment, in addition to the equipment granted by your background:

  • (a) a rapier or (b) a shortsword
  • (a) a shortbow and quiver with 20 arrows or (b) a shortsword
  • (a) a burglar’s pack or (b) a dungeoneer’s pack or (c) an explorer’s pack
  • Leather armor, two daggers, and thieves’ tools
Table: Mistress of the Web
Level Proficiency Bonus Deceptive Attack Feature
1st +2 1d6 Master Deceiver, Expert Linguist
2nd +2 1d6 Cunning Action, detect thoughts
3rd +2 2d6 The Serpent’s Tongue
4th +2 2d6 Ability Score Improvement
5th +3 3d6 The Tongue of the Multiverse
6th +3 3d6 Deceptive Uncanny Dodge
7th +3 4d6 Evasion
8th +3 4d6 Ability Score Improvement
9th +4 5d6 The Tongue of the Multiverse
10th +4 5d6 Ability Score Improvement
11th +4 6d6 Reliable Deception
12th +4 6d6 Ability Score Improvement
13th +5 7d6 All of your Heart’s Desires
14th +5 7d6 Blindsense
15th +5 8d6 The Tongue of the Multiverse
16th +5 8d6 Slippery Mind, Ability Score Improvement
17th +6 9d6 Deceiver’s Gambit
18th +6 9d6 Elusive
19th +6 10d6 Ability Score Improvement
20th +6 10d6 Your Heart and Soul, The Tongue of the Multiverse

Class Features

As a mistress of the web, you have the following class features.

Master Deceiver

At 1st level, you gain skill proficiency in Deception and Persuasion. Your proficiency bonus is doubled for any ability checks you make that uses either of these two proficiencies. At 6th level, you can choose two more proficiencies (in skills or with tools) you have to also get this benefit.

Expert Linguist

Also at 1st level, you have realized the importance of language to get what you want. Your studies render you a true polyglot. You gain an additional language of your choice that you can speak, read and write. At 3rd, 5th, 7th, 9th, 11th, 13th, 15th, 17th and 19th level, you learn an additional language. You need to have had some sort of exposure to the language either via writing, communication or similar means to be able choose a language.

Deceptive Attack

Beginning at 1st level, you have learned to sow doubt in your foes. As either an action on your turn or as part of using the Dodge or Disengage action, you can make a Charisma (Deception) check against the attacker and manipulate the target. The DC for this check is equal to the target’s AC or 8 + the target’s proficiency bonus + the target’s Wisdom modifier, whichever is higher. If you succeed, you have sown enough doubt within the target to make it susceptible to your deceptive attacks for a number of turns equal to your Charisma modifier. Once per turn, you can deal an extra 1d6 damage to a creature thus affected that you hit with an attack. The attack must use a finesse or ranged weapon. The amount of extra damage increases as you gain levels in this class, as shown on the Deceptive Attack column of the Mistress of the Web table.

You need to be able to speak with the target creature and share a language with it to use this ability.

Cunning Action

Starting at 2nd level, 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.

Detect Thoughts

Also at 2nd level, you gain an almost supernatural awareness of other creatures and their inner workings.

You learn the detect thoughts spell. You can use this spell a number of times equal to your Charisma modifier before requiring a long rest to recharge. You do not need a material component for the spell. Your spellcasting attribute is Charisma.

The Serpent’s Tongue

At 3rd level, you learn to worm your way into the hearts and minds of those foolish enough to allow you to speak to them. A non-hostile creature listening to you for 1 minute or longer must make a Wisdom saving throw against DC = 8 + twice your proficiency bonus + your Charisma modifier. On a failure, the creature becomes charmed by you until it has completed a long rest. Since this effect is not magical, it cannot be countered or dispelled, and it can only be thwarted by reasoning with the target. Similarly, the target continues to consider you a friendly acquaintance even after completing a long rest and continues to do so until given sufficient reason to doubt your intentions. Obviously self-destructive requests made from charmed creatures result in this effect immediately ending. Similarly, witnessing you betray one charmed creature automatically ends the charmed condition on all creatures you have charmed with this ability that can witness the betrayal.

If you use deceptive attack to attack a creature you have previously charmed with this ability, the stunning realization of your betrayal lets you inflict deceptive attack’s bonus damage against the target with all your attacks for a number of turns equal to your proficiency bonus plus your Charisma modifier.

Ability Score Improvement

When you reach 4th level, and again at 8th, 12th, 16th and 19th level, you can increase one ability score of your choice by 2, or you can increase two ability scores of your choice by 1. As normal, you can’t increase an ability score above 20 using this feature.

The Tongue of the Multiverse

At 5th level, you have learned that language is not necessarily only conveyed through words, but also gestures, facial expressions and the like.

With expert zeal, you have started applying the deceptive craftsmanship of your trade to this form of communication as well. Choose two monster type from the following: Aberration, Beast, Celestial, Construct, Dragon, Elemental, Fey, Fiend, Giant, Monstrosity, Ooze, Plant, Undead. You can use your deceptive attack class feature against creatures of this type without sharing a language. At 10th, 15th and 20th level, you can choose an extra monster type.

Deceptive Uncanny Dodge

Starting at 5th level, when an attacker that is an eligible target for your deceptive attack hits you with an attack, you can use your reaction to negate the attack’s damage.


Beginning at 7th level, you can nimbly dodge out of the way of certain area effects, such as a red dragon’s fiery breath or devastating spells. When you are subjected to an effect that allows you to make a Dexterity saving throw to take only half damage, you instead take no damage if you succeed on the saving throw, and only half damage if you fail. If the effect is prompted by a creature that is currently an eligible target for your deceptive attack feature, you may substitute your Charisma saving throw for your Dexterity saving throw before rolling the saving throw. If you do, however, the target ceases to be an eligible target for your deceptive attack and has to be deceived again.

Reliable Deception

By 11th level, you simply make no glaring mistakes when manipulating people and are similarly hard to manipulate or undermine. Whenever you make a Charisma (Deception) or Charisma (Persuasion) check, you can treat a d20 roll of 9 or lower as a 10. Additionally, whenever you need to make a Charisma saving throw, you can treat a d20 roll of 9 or lower as a 10.

All of your Heart’s Desires

At 13th level, you have learned to capitalize on the discord and doubt you have sown and turn enemies into allies. As an action, you can promise all of a creature’s heart’s desires to help you—whether you intend to keep your promise or not determines whether you use Deception or Persuasion when using this feature. The DC for this check is equal to the target’s AC or 8 + the target’s proficiency bonus + the target’s Wisdom modifier, whichever is higher, and you may only target creatures that are eligible targets for your deceptive attack or currently charmed by you. Creatures thus affected must make a Wisdom saving throw against DC = 8 + twice your proficiency bonus + your Charisma modifier.

On a failure, they switch allegiances and fight for your cause. This is a nonmagical effect and as such has no duration, but having to go against one’s convictions, attack erstwhile allies, etc. allow the creature to reroll the saving throw. Similarly, heartfelt arguments roleplayed by other characters may allow for a reroll, subject to the GM’s discretion. If you fail to deliver on your promises, the effect will end as well. A creature that successfully saves against this ability cannot be affected again until you have completed a long rest. Since these promises usually entail morally questionable suggestions, it is not uncommon for creatures that have resisted you to become weary of you. If you use this ability on a charmed creature and it successfully saves against it, the creature is no longer is charmed and becomes immune to your deceptive attack feature until you have completed a long rest. Note that this ability also allows you to end charm effects of other creatures; the victims may actually be grateful to you.


Starting at 14th level, if you are able to hear, you are aware of the location of any hidden or invisible creature within 10 feet of you.

Slippery Mind

By 15th level, you have acquired greater mental strength.

You gain proficiency in Wisdom saving throws.

Deceiver’s Gambit

When you reach 17th level, you have become adept at striking for maximum effect after deceiving creatures.

You can take two turns during the first round of any combat that you initiate or that begins due to a creature successfully saving against one of your class features.

You take your first turn at your normal initiative and your second turn at your initiative minus 10. During this round, all creatures are considered to be eligible targets for your deceptive attacks and you gain advantage on attack rolls made against such creatures. You can’t use this feature when you are surprised.


Beginning at 18th level, continuous escapes from those you deceived bear fruit. No attack roll has advantage against you unless you are incapacitated or restrained.

Your Heart and Soul

At 20th level, your dominion over those that listen to your promises becomes absolute. Whenever you manage to inflict the charmed condition on an adversary or use your all your heart’s desires class feature, you gain permanent and unswerving devotion from the affected. No amount of reasoning can reverse the process or grant additional saves. The affected creature is willing to die and even condemn its soul for you. Magic is powerless to break your hold over a creature thus affected, with the exception of direct divine intervention or the wish spell. Creatures saved from your domination forevermore are immune against being charmed by you.

Section 15: Copyright Notice

Underworld Races and Classes © 2017 AAW Games LLC; Designers: Thilo Graf and Mike Myler