Before you took to adventuring, you were once a member of the oldest profession, exchanging money for the pleasure of your company. The life of a harlot is a dangerous one – only slightly less dangerous than being an adventurer – and you have survived based on your quick wits and natural charm. You may have started in the trade young, forced into the life after a childhood of poverty. Alternatively, you have only recently taken up the profession to pay for adventuring school.

Equipment: A long crimson cloak, a set of common clothes, a set of revealing clothes, & a belt pouch containing 15 sp in assorted coinage.

Welcome Company   People pay well for fine company, so you seldom have trouble finding a roof to sleep under. Even if your hosts do not fully avail themselves of your services, you know how to engage the imagination and entertain the spirit. While relaxed, people often let information slip that they shouldn’t. You can use your wiles to learn local rumors and secrets. This information tends to be unfocused and learning specific details is more challenging. You are also able to identify local harlots, who are typically willing to support fellow members of their profession. They are also able to share information they have pried from their clients and loan you mundane goods and other simple equipment.

d8	Personality
1	I remain cheerful & optimistic despite my lifestyle, as if heart were made of gold.
2	I’m bitter from painful experiences, and everything I say sounds sarcastic or cynical.
3	I’m a mimic, adept at shifting my persona to what the situation requires. I adore trying new things and being new people.
4	I like to take what I want, when I want. I loathe being told “no”.
5	Regardless of my situation, I maintain an air of class and distinction, and always remember my manners.
6	I’m a shameless flirt, and love being the center if attention.
7	I’m a little suspicious, worried about being betrayed and caution of being assaulted.
8	I’m quiet, always listening and paying attention to my surroundings.

d6 Ideal
Independence No one will have power over me again. (Chaos)
Lust: I fill my urges when and where I wish. (Evil)
Honesty One must abide by their deals and fulfill what they paid to do. (Lawful)
Money There are things I won’t do for gold… but not much. (Neutral)
Secrets Knowing someone’s secrets gives you power. (Neutral)
Loving: Everyone needs attention, joy, and love. (Good)

d6 Bond
All sex workers are my brothers and sisters, and I must defend them.
If I can only collect enough gold, I’ll be able to pay off my debts and be a free man (woman)
I protect the identity and secrets of my clientele.
I have family that I’m working to support.
My reputation determines my value and must be maintained.
I seek a relationship with the most powerful people in the land, desiring to be the power behind the throne.

d6 Flaw

I no longer believe in love.

I judge people for what they can do for me.

Once I was a slave, and I still possess the mark and the brand. If found out my freedom is forfeit.

I am fighting addiction to an illicit substance with varying success.

I can’t stand anyone who tries to be nice to me. They only want me to sleep with them.

I will do anything to raise my station in life.

You focus your training on the grim art of death. Those who adhere to this archetype are diverse: hired killers, spies, bounty hunters, and even specially anointed priests trained to exterminate the enemies of their deity. Stealth, poison, and disguise help you eliminate your foes with deadly efficiency.

 

Bonus Proficiencies

When you choose this archetype at 3rd level, you gain proficiency with the disguise kit and the poisoner's kit.  

Assassinate

Starting at 3rd level, you are at your deadliest when you get the drop on your enemies. You have advantage on attack rolls against any creature that hasn't taken a turn in the combat yet. In addition, any hit you score against a creature that is surprised is a critical hit.  

Infiltration Expertise

Starting at 9th level, you can unfailingly create false identities for yourself. You must spend seven days and 25 gp to establish the history, profession, and affiliations for an identity. You can't establish an identity that belongs to someone else. For example, you might acquire appropriate clothing, letters of introduction, and official- looking certification to establish yourself as a member of a trading house from a remote city so you can insinuate yourself into the company of other wealthy merchants.   Thereafter, if you adopt the new identity as a disguise, other creatures believe you to be that person until given an obvious reason not to.  

Impostor

At 13th level, you gain the ability to unerringly mimic another person's speech, writing, and behavior. You must spend at least three hours studying these three components of the person's behavior, listening to speech, examining handwriting, and observing mannerisms.   Your ruse is indiscernible to the casual observer. If a wary creature suspects something is amiss, you have advantage on any Charisma (Deception) check you make to avoid detection.  

Death Strike

Starting at 17th level, you become a master of instant death. When you attack and hit a creature that is surprised, it must make a Constitution saving throw (DC 8 + your Dexterity modifier + your proficiency bonus). On a failed save, double the damage of your attack against the creature.