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exploring jam sandwich, second daughter of pinkie pie:

1.) Jam apprenticing under the world famous FlimFlam brothers

i'm sure this will go well

2.) The student becomes the master! Later, suckers!

Jamboree Jessie Sandwich has one, and only one goal in life......and that's to become filthy stinkin' rich. Jam's spent most of her life amongst Ponyville rubes, who are "content" and "fulfilled" by their cozy, quaint, utterly boring one-horse town. Jammie wants more! Adventure! Prestige! And money, mostly. Lots of money. This means Jam's been cookin' up get-rich-quick scams since she was pretty much in diapers.

Like the FlimFlam bros, Jam once hoped to form an entrepreneurial duo with her twin brother, PB Sandwich. Unfortunately, PB is less of the cutthroat business partner she needs and more of....well, an idiot. And she means that in the most loving way, really! PB is just too sweet and trusting, with the rather annoying habit of dumping their proceeds on some hungry beggar on the street. Celestia damn it. For this reason, Jam says goodbye to Peebs and goes solo, heading to Canterlot, Equestria's shiny golden capital, where the uppitiest of the uppercrust reside.

3.) the original premise of jam and artemis' relationship has long become stale to me (it was really only ever just Jam pestering Artie into dating her, ick), so i'm changing it up

Although Artemis and Jam had always seen glimpses of each other growing up, the first time they meet formally is when Jam is arrested in Canterlot. It's her first time in the big city on her own, so her schemes were admittedly a bit crude. What can she say? She was a rookie back then! She's set up a small gambling ring to prey on Canterlot nobles when she's caught by none other than Artemis, non-binary heir to Queen Luna, captain of the royal guard, and official No-Fun McFeatherface. Oops.

Artemis swiftly arrests the charlatan and leads her away for processing. Despite being informed she has the right to remain silent, the little pink pony simply won't. Stop. Talking. About the most inane things! The weather, how Artemis likes it here in Canterlot, recipes for bundt cake....and good lord, the flirting. Artemis has never met such a cheeky commoner, nopony has ever dared to cuddle up to the Alicorn of the Eventide. The impudence! The audacity!

Meanwhile, Artemis hasn't yet noticed that Jam's already shimmied her cuffed arms from behind her back to her front, and is quietly picking the locks with a bobby pin.

And so Jam gives ol' Artie the slip. Artemis spends all day doggedly pursuing her, but she always just manages to evade them and their night guard, leaving Artemis annoyed, exhausted, and..........admittedly, somewhat entertained.

Artemis wonders......after all these years, and all this boredom.....have they finally discovered a worthy adversary?

headcanon from the enchanting : So now I'm semi-retconning that one old headcanon I had about Artemis assigning their personal guard to protect Jam. Now the guards are ordered to ARREST her on sight. Jam simply evades, dodges, and throws pies at them (Eclipse's pride takes WEEKS to recover). I like to think she cheekily leaves a pie on Artemis' desk afterward with a flirty (and highly suggestive note) stating she can't wait for their next "date". And the night heir finds themselves going through several emotions...and can't quite explain the fluttering in their chest or the sudden flare of anticipation for their next encounter.

4.) Following up Jam's first few negative encounters with Artemis, she decides to don a dress and sneak into a big fancy garden party in Canterlot. Artemis, rather bored making conversation with the aristocrats, is surprised at a tap at their shoulder and an invitation to dance, from none other than the pink menace herself.

Hm. Well. Perhaps it is a private event, but Artemis' officers are on guard. Perhaps one dance wouldn't hurt. One conversation. One evening......

And so Jam and Artemis fall into a long, long game of cat and mouse, with Jam pulling off clever cons and petty crime around Canterlot, and Artemis attempting to thwart her. Sometimes Jammie comes out on top, and sometimes Artemis spoils her fun. Jam's interest in Artie is 20% just-for-funsies flirting, 80% careful monitoring of Artemis’ position so she can scheme uninterrupted. At least, that's what she tells herself. Never fall for your own con, Jammie always says! Never fall for your own con....
.

~~~~~~~~~~~~~~~~~~~~~~~~~

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Description

exploring jam sandwich, second daughter of pinkie pie:

1.) Jam apprenticing under the world famous FlimFlam brothers

i'm sure this will go well

2.) The student becomes the master! Later, suckers!

Jamboree Jessie Sandwich has one, and only one goal in life......and that's to become filthy stinkin' rich. Jam's spent most of her life amongst Ponyville rubes, who are "content" and "fulfilled" by their cozy, quaint, utterly boring one-horse town. Jammie wants more! Adventure! Prestige! And money, mostly. Lots of money. This means Jam's been cookin' up get-rich-quick scams since she was pretty much in diapers.

Like the FlimFlam bros, Jam once hoped to form an entrepreneurial duo with her twin brother, PB Sandwich. Unfortunately, PB is less of the cutthroat business partner she needs and more of....well, an idiot. And she means that in the most loving way, really! PB is just too sweet and trusting, with the rather annoying habit of dumping their proceeds on some hungry beggar on the street. Celestia damn it. For this reason, Jam says goodbye to Peebs and goes solo, heading to Canterlot, Equestria's shiny golden capital, where the uppitiest of the uppercrust reside.

3.) the original premise of jam and artemis' relationship has long become stale to me (it was really only ever just Jam pestering Artie into dating her, ick), so i'm changing it up

Although Artemis and Jam had always seen glimpses of each other growing up, the first time they meet formally is when Jam is arrested in Canterlot. It's her first time in the big city on her own, so her schemes were admittedly a bit crude. What can she say? She was a rookie back then! She's set up a small gambling ring to prey on Canterlot nobles when she's caught by none other than Artemis, non-binary heir to Queen Luna, captain of the royal guard, and official No-Fun McFeatherface. Oops.

Artemis swiftly arrests the charlatan and leads her away for processing. Despite being informed she has the right to remain silent, the little pink pony simply won't. Stop. Talking. About the most inane things! The weather, how Artemis likes it here in Canterlot, recipes for bundt cake....and good lord, the flirting. Artemis has never met such a cheeky commoner, nopony has ever dared to cuddle up to the Alicorn of the Eventide. The impudence! The audacity!

Meanwhile, Artemis hasn't yet noticed that Jam's already shimmied her cuffed arms from behind her back to her front, and is quietly picking the locks with a bobby pin.

And so Jam gives ol' Artie the slip. Artemis spends all day doggedly pursuing her, but she always just manages to evade them and their night guard, leaving Artemis annoyed, exhausted, and..........admittedly, somewhat entertained.

Artemis wonders......after all these years, and all this boredom.....have they finally discovered a worthy adversary?

headcanon from the enchanting : So now I'm semi-retconning that one old headcanon I had about Artemis assigning their personal guard to protect Jam. Now the guards are ordered to ARREST her on sight. Jam simply evades, dodges, and throws pies at them (Eclipse's pride takes WEEKS to recover). I like to think she cheekily leaves a pie on Artemis' desk afterward with a flirty (and highly suggestive note) stating she can't wait for their next "date". And the night heir finds themselves going through several emotions...and can't quite explain the fluttering in their chest or the sudden flare of anticipation for their next encounter.

4.) Following up Jam's first few negative encounters with Artemis, she decides to don a dress and sneak into a big fancy garden party in Canterlot. Artemis, rather bored making conversation with the aristocrats, is surprised at a tap at their shoulder and an invitation to dance, from none other than the pink menace herself.

Hm. Well. Perhaps it is a private event, but Artemis' officers are on guard. Perhaps one dance wouldn't hurt. One conversation. One evening......

And so Jam and Artemis fall into a long, long game of cat and mouse, with Jam pulling off clever cons and petty crime around Canterlot, and Artemis attempting to thwart her. Sometimes Jammie comes out on top, and sometimes Artemis spoils her fun. Jam's interest in Artie is 20% just-for-funsies flirting, 80% careful monitoring of Artemis’ position so she can scheme uninterrupted. At least, that's what she tells herself. Never fall for your own con, Jammie always says! Never fall for your own con....
.

~~~~~~~~~~~~~~~~~~~~~~~~~

Enjoy my content? Please consider supporting me on Patreon! It has rewards, sneak peeks, secret doodles, and early viewing of finished art for patrons! Also, for each funding goal met, I produce a new promised art and story reward!
Support on PATREON!