Courtesan

Courtesans are masters of subtlety, infiltration, manipulation, and assassination, all stemming from their ability to use intimacy and trust from their patrons to their own ends.

Saving Throws. Some of your features require your target to make a saving throw to resist the effect. The saving throw DC is equal to 8 + your proficiency bonus + your Charisma modifier.

Level 3: Undeniable Allure

Level 3 Courtesan feature:

To an extent, when combat begins, you're just too pretty to hurt. Either through your physical attractiveness or your force of personality, enemies are reluctant to harm you. When wearing no armor nor holding a shield, your AC is 10+ your Dexterity Modifier + your Charisma modifier.

Once per short rest, as a Reaction, you can appeal to one creature you select that attempts to harm you with an attack or spell attack. The creature makes a WIS saving throw. On a failure, they become Charmed by you until the beginning of their next turn.

Level 3: Irresistibility

Level 3 Courtesan feature:

Whether it’s just stunning physical appearance, enthralling personality, or another ethereal quality, you stand out from the masses. Beginning at 3rd level, you can use an Action and attempt to charm one humanoid that you can see within 30 feet.

The creature must make a Wisdom saving throw, and does so with Advantage if you or your companions are fighting it. If it fails the saving throw, it is Charmed by you for 1 minute, or until you or your companions do anything harmful to it. The charmed creature regards you as a friendly acquaintance.

You can use this feature a number of times equal to your to your proficiency bonus. Regain all uses on a Long Rest.

Tools of the Oldest Trade

Level 3 Courtesan feature:

Courtesan’s are not merely merchants of flesh, but of companionship and entertainment. You gain proficiency in an instrument and gaming set of your choice.

Your secondary line of work also calls for covertness and discretion. You gain proficiency with the Poisoner’s Kit.

Level 9: Enrapturing Presence

Level 9 Courtesan feature:

Your attentions have a lasting impact on others, and with some subtle persuasive action, you can wrap folk around your finger.

Beginning at level 9, if you spend at least 30 minutes interacting with a creature in constant, close proximity (within 10 ft), you may attempt to garner its favor to your own ends. As an action, you may make a Persuasion (CHA) check contested by the creature's Insight (WIS) as you you ask one reasonable favor of the creature.

If you succeed the check, the creature becomes Enraptured by you for up to 24 hours, and will do its best to comply with your request. This condition ends if you attack the creature.

If you fail the check, the creature becomes immune to being Enraptured for 24 hours, but otherwise does not change its opinion of you (up to DM discretion).

The favor may be to share information, to act as an armed escort, or to start a fight with someone in a saloon, but must be able to be completed within 24 hours. Once a favor is completed, you may attempt to ask another favor while the creature is Enraptured, with another contested roll, but the creature gains a +5 bonus to its Insight roll each time you attempt it, unless you spend another 30 minutes in close proximity. The creature's memory of any favor granted while Enraptured will seem reasonable and consensual.

If your favor is something that will directly result in the creature's death, or something opposite to what would seem a rational course of action to it, the creature will refuse, laughing off the idea as a joke, but will remain Enraptured. You may request another favor after this refusal one time. A second refused request will necessitate another contested roll to ask a new favor.

After the initial 24 hours have passed and the Enrapturement ends, the creature will treat you no differently.

Additionally, when you are targeted by an attack or a spell, any creature Charmed or Enraptured by you will automatically attempt to defend you as a Reaction, interposing themselves between you and attacks or harmful effects. The creature must expend no more than 10 feet of movement to do so, and if there is no available space between you and your attacker, will push you 5 feet away from the attacker, forcing you to make a Dexterity saving throw (DC 10+STR bonus) to avoid being knocked prone.

Level 13: Cruel Mistress

Level 13 Courtesan feature:

Love can indeed be a cruel mistress, and you take loving and cruelty to their extremes.

You have advantage on attacks against creatures Charmed or Enraptured by you.

When you successfully Sneak Attack a creature that you have Charmed or Enraptured, it becomes vulnerable to all the damage you deal with the attack.

Upon landing a successful attack on a Charmed or Enraptured creature, you may attempt to explain your behavior so as to avoid retaliation; make a (CHA) Deception check, with a DC equaling 15, or half the damage dealt, whichever is higher. On a successful check, they will remain Charmed or Enraptured for the remaining duration. You may use this ability only once on any creature while they are Charmed or Enraptured, and the creature gains a +10 to any subsequent ability check or saving throw to avoid being Charmed or Enraptured by you.

Level 17: Heartbreak

Level 17 Courtesan feature:

Creatures emotionally entangled with you are blind to the possibility of your betrayal, and are dazed with disbelief when you strike.

You may reduce the Initiative roll of any creature Charmed or Enraptured by you by a number equal to your Proficiency Bonus plus your Charisma modifier.

Additionally, if you successfully Sneak Attack any creature Enraptured or Charmed by you, they become Paralyzed until the end of their next turn.