Portrayed by Christina Hendricks

Name: Jessilyn
Title: Madam
Alias: jess
Faction: The Bawdy Bard Brothel
Fealty: The Reach
Status Rank: Smallfolk
Occupation: Courtesan
Wealth: Wealthy


A young woman with an elvish youthful look about her. She has nearly luminescent pale skin, shining sky blue eyes, stands about 5'7" tall, and is approximately 122 pounds. Her hair is long and coppery red with a slight natural waviness.
Nearly ageless, she almost seems like she'll appear to be in her early twenties all of her life. High cheekbones bones are naturally rosy at the apples and when she smiles they grow enough to make her prim little nose even tinier on her face. Her blue eyes as well are on the slight side so they nearly vanish whenever a smile graces her face, pearly if a bit skewed teeth sparkling. In the common feminine egg shape, her face has a majestic forehead but soft chin. With a fuller bottom lip than her top lip, both are stained a lush fiery red with lip rouge. Much like the rest of her physique her mouth is thin but is curvy where it counts.

While the smallfolk woman is looking as close to a noble as one could, there is a line that Jessi doesn't cross. She manages to mix colors together that doesn't infringe on any house, at least any of the more well-known houses. She never has too intricate of embroidery that has animals or other heraldic symbols within it. She's always just shy on over-stepping in her appearance. But damn, does she walk the fine line well. Today she's wearing a forest green raw silk gown that is simple but in a refined sophisticated manner. The collar sits off of her shoulders and a square knot is used as decoration hanging off of her right shoulder. The cut of the bodice and collar proudly show off her curves and even more, attention is brought to her cleavage by a necklace she wears. A thick silver chair encircles her neck. It's heaving but elegant and is thick so that it can support the hunk of silver that's stylized into the rough shape of a heart. The point of the heart being the attention drawer as it points right down to her most ample of assets.

Brief Biography

Jessilyn was the product of a farm girl, Teena, being raped by a Wildling in the Gift up North. Teena ended up a whore in an Undercity brothel and gave Jessilyn to one of her clients, a failed maester named, Harver. The girl took up with a band of fellow entertainers and they became a Mummer Band of growing repute in Oldtown. Things were going as well as they could for a girl in her situation. That is until her mother discovered she had her first moonblood and kidnapped and sold her own daughter's maidenhood off to the highest bidder.

After that, the ruined Jessilyn was broken for a while. But in time she regained her strength and plotted and rose in fame and talent and was very soon outshining her mother and putting Teena out like an old nag. Once replacing Teena as the Madam of the seedy brothel, Jessilyn continued to rise and put much of the money she and her girls made to better all of their situations. Jessilyn turned a nameless seedy brothel in the Undercity into a sprawling den of pleasure and vice that had access to the more accessible Oldtown Square with the Undercity at its backdoor. The Bawdy Bard is a place where nobles and smallfolk alike can come and find some great entertainment and pleasure. Jessilyn makes sure that everyone feels welcomed and leaves satisfied. This is her mission in life now.

One of the things that helped along Jessilyn's rise to be a well sought after Courtesan of nobles was catching the attention of a Targaryen Prince of some poor repute, he was in Oldtown escaping his brother's wrath for something or another. The affair was glorious and the gifts and riches poured through Jessilyn into the Bawdy Bard.

Extended Biography

Teena was originally from the Gift. When it was found out that she had been raped and impregnated by a marauder wildling she was banished. Having no choice she whored her way from ship to ship, trying to get as far away from the Wildling infested north as she could. When she arrived at Oldtown she gave birth to a baby girl, Jessilyn. Having a baby made any more travel impossible so Teena settled at a seedy brother in the Undercity of Oldtown. Motherhood wasn't for Teena. She and Jessilyn never got along and Teena always resented Jessilyn for her conception.

At a very young age, Jessilyn and the local kids would play and put on performances in any nook and cranny in the town that they could. What began as child play eventually grew into something more real. They got good enough to earn coin from audiences and eventually, Jessilyn would slide some money under her mother's door from time to time. Jessilyn didn't live with her mother, she had no aim to follow in Teena's footsteps. She stayed with her Mummer friends but mostly she lived with a failed Maester, Harver, that was a regular client of her mothers and the owner of the Apothecary Shop, Toil and Bubble. Harver was the closest thing to a father she had. Until he betrayed her.

The only way her mother could find out that she had come to have her first moon blood was through Harver. Her mother suddenly set upon the daughter she barely knew for the lucrative opportunity of selling the girl's maidenhood to the top bidder. Jessilyn was drugged and kidnapped and

That is until he informed her mother that she'd become a woman. Which was, the beginning of the end for her mother. Jessilyn never believed her mother would be capable of such things. But on her mother's orders she was kidnapped and drugged and her virginity was auctioned off, all for some big party her mother threw when she became Madam of the Brothel. After the party, she was kept in a stupor until she promised her mother she would stay and work for her at the brothel. Several years passed and Jessilyn soon eclipsed her mother in popularity. Using her mummer's tricks her list of clients grew and grew and up the ladder, she climbed until she was considered a 'Courtesan' that was able to mingle at parties on the arm of nobles. Jessilyn had never forgiven her mother for her betrayal and revenge was orchestrated slow but surely. Eventually, she got her revenge by way of forcing her mother to retire and give her the brothel and title of Madam. After that Jessilyn has made adjustments to the brothel, scaling it up some without going so posh the local neighborhood would dislike it. The front of the brothel was reconstructed to expand it enough that a small stage was erected in one of the two parlors. Her old band of Mummers performs there now, every night. Putting on bawdy performances. If the price is right the shows can go from bawdy to downright explicit. All just a fun night at the Bawdy Bard Brothel.





The crazy bitch is rotting somewhere in the Undercity, good riddance.



Foster Father

Jessilyn has forgiven Harver for his betrayal but she's not forgotten it either. She brings him lunch and dinner at the shop and in exchange he gives her medicinal tonics and things that keep herself and her girls healthy.

Prince Daemon

Prince Daemon

Past Lover

They were young, wild and passionate. There was never illusions of being together forever, that very fact fueled their affair. One night he wrapped her in his cloak and they conceived, Bryn. He later had the "wedding cloak" broach turned in on itself and made into a bangle bracelet that leaves the Targaryen crest pressed into the soft flesh of her inner wrist. Not very long after his big brother's wrath subsided and he returned to court, leaving Jessilyn in Oldtown with a growing belly. Stipends and care packages still arrive for her and Bryn even through all of his banishings, marriages and such. He would visit some in the past, but not since he's married Rhaenyra.




Her beloved little dragonseed. She doesn't yet know if her choices in parenting are the best choices. But she has done everything she can to be a better mother than Teena was to her. She didn't give him away, instead raised him to be a little prince at the Bawdy Bard. Never truly exposing him to what goes on behind the girl's doors, but not raising him in naivety either. As a baby and young child, he'd be tucked away in his room sleeping anyways during peak business hours.

Ruslan Redwyne

Ruslan Redwyne


Ruslan was her first big noble client. They were both 16 when she convinced his older brothers to bring him in and give him quite the birthday present in her. The chemistry was immediate and he became her patron, and he could have very well been Daemeron's biological father for the timing of one of his visits between being at sea. He treats Daemeron like he were his flesh and blood son. "I love you so much that even though your son is not mine…the fact he is yours alone means I am willing to claim him. I love you so much that anything of you by extension I shall love too. The distance and time do not change that, my flame. I am a man of steadfast words and emotions. When I say something I meant it whether it be my hate or my love." Those words were his when he first discovered that a baby that could have been his wasn't.

Roleplaying Hooks & Quirks

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Timeline as of 123

  • 93 Jessilyn is born in the seedy brothel in the Undercity.
  • 105 Jess is kidnapped and sold at Teena's Brothel. (Jess is 12.)
  • 109 Jessilyn + Ruslan meet. Ruslan becomes Jessilyn's official Patron.
  • 110 In the later days of Daemon being King of the Narrow Sea he had begun to become "bored" and the Triarchy was breathing down his neck so he left on a bit of a pleasure cruise and landed in Oldtown. This is when he met Jessilyn and they conceived Daemeron. Their escapades included Ruslan enough that Jessilyn spent the whole pregnancy not knowing who the father was.
  • 111 Daemeron Flowers is Born.
  • 120 Daemon marries Rhaenyra and while money still arrives, it doesn't come with the love letters it once did. Daemon has severed ties with Jessilyn because of Rhaenyra.



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