Bard
Base Class: Bard

Drag queens are entertainers of the highest caliber. The makeup, wigs, and glamor are just the beginning. While many begin their career lip-syncing in small taverns, a select few have gone on to become household names throughout the realm, gaining renown as adventurous singers, dancers, comediennes and more. 

Drag Persona

At 3rd level, you master the near-magical techniques used to put yourself into drag and create the illusion of another gender altogether. Without expending a spell slot, you can cast Disguise Self once per long rest to transform yourself into your drag persona. While thus disguised in your drag persona, you gain advantage on all acrobatics, deception, and performance checks. Advantage is only granted when you cast Disguise Self using this feature.

Reading is Fundamental

Also at 3rd level, you learn the classic art of reading: how to use your wit to hilariously and cuttingly sap others of their confidence. When a creature that you can see within 60 feet of you makes an attack roll or ability check, you can use your reaction to make a performance performance check in opposition to their roll. If your roll is higher than the creature's, the creature takes 1d4 psychic damage. Your use of this ability has no bearing on the success or failure of your opponent's roll. You cannot use this ability on a creature that cannot hear you.

The amount of damage increases to 1d6 at 5th level, 1d8 at 10th level, and 1d10 at 15th level.

Dip

Dips--known in some circles as death drops, 5000s, or shawhams--are a striking dance move that can inspire awe in any who see them. Beginning at level 6, you may use a bonus action to perform an acrobatics check (DC 15). Upon a successful check, a number creatures you can see within 30 ft. equal to your charisma modifier become charmed. At the end of each of their subsequent turns, affected creatures may make a Wisdom saving throw against your Spell Save DC to remove the condition. The effect ends if you or any of your companions do anything harmful to the affected creature. If you fail your acrobatics check, you fall prone and the targets experience no effect.

Lipsync

Starting at 14th level, when you are required to make an ability check, you can expend one use of Bardic Inspiration. Instead of making the required check, you may make a deception check instead.You can choose to do so after you roll the die for the ability check, but before the DM tells you whether you succeed or fail.

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