Courtesan

You have one foot in either extreme of society. On the one hand, you have a borderline legendary knack for coaxing favors, secrets, and a lot of material wealth out of the ruling class. On the other hand, you're captive to the trappings of your profession, and you likely have little to no independent wealth. Your lavish appearance and lifestyle belie the transactional precarity that defines your existence, and you may have to take on criminal or otherwise compromising tasks to repay or avoid debt. Even in countries where the profession is considered sacred or respectable, trying to stay above water and above board can feel like a Sisyphean task with the impossible standards and the expense of trying to meet them. On the other hand, if you're of certain fiendish lineages, it may feel like getting paid to eat, or at least like it's the best job you can hope to find.

You may have a patron who is deeply in love with you and willing to move mountains for you. You may be indebted to a powerful crime lord with whom you trade favors. You may whip a politician or religious leader in private while they excoriate your profession in public. If you have any genuine confidants other than a loving patron, they are likely to be others in bondage, outlaws, or the odd misguided missionary.

Discuss with your DM about about the legal, social, and religious status of your profession throughout the campaign setting, and if applicable, how tolerant the society is of humanoids of your species. Are you legally chattel, an indentured servant, a temple ward, an independent contractor, or something else? How freely does your status allow you to travel, and where my your presence be restricted or forbidden? In societies where it the profession is legal (or at least decriminalized), or where organized crime syndicates hold the power of a parallel or de facto governments, there often exist parallel social ladders for hereditary nobility and celebrities. In these societies, a sufficiently popular courtesan might be invited into the halls of power as a distinguished guest rather than strictly as entertainment. However, they will still typically be required to speak, act, and dress in ways that signal deference to hereditary nobility, especially to their patron and that patron's superiors.

Consult with your DM about who your patron or patrons are (or were), and what sort of leverage you and your patron have over each other. How does your patron afford your services, and where does that put them with respect to the local law, social order, or religious caste system? Is your patronage relationship public? If not, what would happen if you or your patron(s) were outed? If you have or had multiple patrons, how do they interact, if at all?

Your patron's nobility or infamy can become important features of the campaign setting.

Skill Proficiencies: Choose two from among Insight, Persuasion, and Performance

Tool Proficiencies: Choose one type of gaming set and one instrument

Languages: One of your choice

Equipment: A bottle of black ink, a box of stationary with a quill, a set of fine clothes including fashionable headwear, and a pouch containing 20 gp

Suggested Characteristics

In many countries, the training of courtesans for nobles' entertainment is an entire industry into which the "products" are sold or trafficked into at a very young age. Despite the creature comforts, trauma features heavily in the lives of courtesans, whether they were bought and trained, or in the rare event that they reached their status as an independent contractor. Depressingly similar life circumstances are often involved even in countries where a religious context gives the profession a relatively high social status. Courtesans learn early to repress their emotions and behave in whatever way maximizes their profits or status and minimizes their abuse. As a result, many are emotionally unavailable even if they want to open up, and struggle to regain their composure if they lose it. They may or may not have experience coping with squalid living conditions.

Being descended from succubi/incubi is its own source of trauma, which the process of becoming a courtesan may have compounded, alleviated, or had no effect one way or the other. A lot depends on how tolerant one's local culture is of both diversity among humanoids and the courtesan's profession.

d8	Personality Trait
1	My eloquent flattery makes everyone I talk to feel like the most attractive and important person in the world.
2	I stay calm and rational regardless of the situation. Shouting and losing one's composure only ever makes things worse.
3	The first thing I do when I meet someone is study their body language so I know who is really in control.
4	I'm a hopeless romantic in spite of everything. A lot of my clients just want someone to be vulnerable with.
5	I think everyone is a two-faced faker until proven otherwise. The most publicly prudish clergy are always my filthiest customers.
6	I can crack a raunchy joke in almost any situation.
7	I'm confident in my ability to defuse tempers and charm my way out of trouble. Perhaps a bit too confident.
8	My patron spoils me rotten. I must always wear the latest fashions, eat the finest foods, and sleep in luxury.

d6	Ideal
1	Honor. I avoid taking married customers or helping them break religious vows if they are not prepared to leave those institutions. (Lawful)
2	Freedom. I live for the day when I can earn or seize my independence. (Chaotic)
3	Justice. My job is a means to ensnare and expose corrupt nobles. (Good)
4	Greed. I will do anything for more money and higher status. (Evil)
5	Responsibility. I must protect my juniors from patrons who would hurt them and teach them the skills they need to survive in this world. (Good)
6	Beauty. I make art, I wear art, and I am art. I live for sparkle in the eyes of those who watch me. (Any)

d6	Bond
1	My parents got into debt with a powerful family, and now I'm stuck serving their head to pay it off.
2	I had a baby with one of my clients, and want to track down the other parent and/or my child.
3	I hope to have my art or entertainment skills recognized by a guild or patron so I can switch careers.
4	I convinced a decent noble to buy me/settle my debts. I'm not really in love with them, but they are my benefactor and I care for them deeply.
5	For political reasons, I'm on the run. But don't worry, I have a friend on the inside.
6	My patron thinks I'm too young to remember how I ended up in their "care". Well, you know what they say about the best way to serve revenge.

d6	Flaw
1	I'm an addict. It kind of comes with the lifestyle.
2	When faced with a choice between money and friends, I usually choose the money.
3	I'm too fond of gossip. I've let slip a few things that could get me killed if they're traced back to me.
4	Any less-than-flattering comment about my age or appearance will be met with a slap before I have time to think about who is talking.
5	I am not above hiding behind other people when faced with danger.
6	Given the excuse to torment people who look like my clients, I will do so with way too much gusto.