Courtesan

Though it's a fancy name for a prostitute, you worked in a finer establishment than the standard tavern or brothel.  You have serviced clientele of the highest echelons of society, though you're still willing to serve anyone who can pay the right price.  Because of the many nuances involved in your trade, you've developed a keen insight for other people's body language, speech, mannerisms and more.  You know how to read people and discover their desires, but even more, you know how to fulfill those desires.

Some courtesans use their particular set of skills to their own advantage, or have been trained by their employers to do other tasks.  Spies, assassins, and thieves have often used the "oldest profession" to further their own aims, and it is not uncommon for a client to suddenly find themselves at the sharp end of a dagger, missing their belongings, divulging sensitive secrets, or dead from a mysterious poison slipped into their drink.

As a courtesan, take the time with your DM to work out some of the details of your background - where did you work?  Who was your employer?  Do you still employ your trade, or have you experienced some kind of reformation that allows you to still utilize your skills at reading people?  Did you leave your trade because of an abusive client who is still hunting you, or have you struck out on your own to establish your own business?  Are you an assassin for hire, a spy for your homeland, or a con-artist looking to loosen coin purses at the same time as you loosen their trousers?

Whatever you desire... the courtesan can find a way.

Skill Proficiencies: Courtesans have mastered the ability to read and manipulate their clientele into both revealing and experiencing their deepest desires and fantasies.  As such, courtesans are proficient in Insight and Persuasion.

Tool Proficiencies: Working with your DM, you may choose a proficiency in two tools from the following options: Disguise Kit, Forgery Kit, Gaming Set, Herbalism kit, Musical Instrument, Poisoner's kit, or Thieves' tools.

Languages: Courtesans are adept at adjusting to their clients' needs.  In the time you've spent in your trade, you've gained one additional language of your choice in addition to Common and whatever racial languages you may already know.

Equipment: You carry a dagger for self-defense, in case of the occasional unruly client.  Additionally, you possess either a costume or a set of fine clothes, a vial of perfume, and your choice of one set of tools related to the proficiencies you have chosen.

Suggested Characteristics

A good courtesan knows both how to smile like a saint and curse like a sailor - like the charlatan, courtesans are colorful characters with a true inner self hidden deep within.  They are social chameleons who know how to adapt quickly to reflect the desires and attitudes of the people they seek to charm, seduce, and please.  But behind all the makeup, costumes, and tricks, every courtesan has someone else who they truly are - whether a dreamer, a schemer, a realist or a martyr, the true nature of a courtesan is a diamond in the rough.

d8	Personality Trait
1	I love attention and will go out of my way to receive it.
2	I try to blend in with whatever crowd I'm in.
3	I love meeting new people because of the challenge of learning their desires.
4	I've been wined and dined by the finest of society, and look down on more ordinary fare.
5	I harbor deep dreams of rising above my profession to become something greater.
6	I'm always ready in case a client turns nasty.
7	I have a hard time making close connections and real friendships, but am fiercely loyal to those whom I have chosen.
8	I occasionally forget my situation and use bad etiquette or say the wrong phrases for the wrong place.

d6	Ideal
1	Aspiration. I dream of truly being one of the "upper class" instead of having to pretend that I am - even for just one day. (Any)
2	Adaptability. The only way to succeed is to be whatever the customer needs you to be. (Chaotic)
3	Opportunistic. I take every advantage given to me to get myself what I really want. (Chaotic)
4	Power. I use my position and abilities to manipulate people and gain leverage. (Evil)
5	Realism. You have to do what you can to survive in this world. (Neutral)
6	Pleasure. Pleasing other people brings me fulfillment. (Good)

d6	Bond
1	I sell my body to provide for my family. I have sickly parents or a young child who desperately needs my support.
2	I am pursued by a wealthy, jilted client who now has it in for me.
3	I am trapped under the thumb of a cruel pimp.
4	I love the finer things that this life provides and strive to find a way to make them my own.
5	I have been so many things to so many people that I'm starting to forget who I really am.
6	I fell in love with one of my clients and I have to find a way to make them love me in return.

d6	Flaw
1	I'm convinced that I can fool anyone into believing anything about me.
2	I'm driven to steal from the people I service and collect trophies from each of them.
3	I have very little sense of personal space.
4	I am obsessed with appearance and will take whatever time I need to look my best.
5	I have a rival whom I'm driven to outdo at whatever cost.
6	I like having any advantage so much that I will even use it against my own friends.