|First appearance||Chapter 18, Page 2|
|Last appearance||Chapter 20, Page 3|
Chapter 20, Page 17
|In real life|
|First appearance||Pokémon (TV series)|
Pokémon Emergency! (1997)
|“||Oh i'm used to handling Balls ;)||”|
|Jessy, Chapter 18: The eye of the storm, Page 6|
Jessy is a character from the Pokemon franchise. Part of Team Rocket, she, alongside James, try repeatedly to steal Pikachu. In Tails Gets Trolled, she is a whore who is apparently good at pool, owing her skill to a lot of practice with balls. She has the clap and is killed by Cheeto Man, her corpse being found alongside Rouge's, Amy's, Candy Kong's, and others by Knuckles and Tails.
Jessy has long red hair, shaped into one large ponytail. She also is seen wearing green earrings and black gloves. Her top is split in two, revealing a black bustier and her cleavage.
Jessy is first seen joining Cheeto Man's party alongside Rogue, Candy Kong, and Patty. She and Rogue join Knuckles and Spryo to play billiards, and ends up teaming with Spryo against the other two. She and Spyro are victorious in the end, and manages to impress Knuckles with her skills (though Spyro claims she is only "ok to below average" at it.) When asked by Spryo, she says that her aptitude for pool comes as a result of her familiarity with handling "balls".
Later in the party she can Spyro begin making out and the two have sex on the pool table, with Spyro eventually thrusting a pool stick up her vagina as he has sex with Rogue. After some time passes, she and Rogue finish having sex with Spyro and she lays on the pool table, exhausted.
Unfortunately, after Knuckles confronts Cheeto Man, the latter kills Jessy off-screen after Knuckles claims that the guests he brought to his party were not free of STDs. Her body is then dumped into Cheeto Man's secret dumping grounds.
Not much can be said of Jessy's personality due to her limited screen-time other than she appears to enjoy sex and balls.
Jessy does not display any particular physical abilities as she is not involved in any battles. She is quite good a playing pool however due to her experience with handling balls.
Real Life Origins
Jessie is a member of Team Rocket, a criminal organization within the world of Pokemon aimed at stealing and selling Pokemon, with the end goal of dominating the world. She is typically seen with her companions James and a talking Meowth. In the animated series, the trio are fixated on stealing away a Pikachu belonging to the protagonist, Ash Ketchum.
In Tails Gets Trolled, Jessie is seen alone without James or Meowth, though she does mention James while having sex with Spyro. Her name is also spelled as "Jessy" instead of its usual spelling as "Jessie". She and James are implied to be in a sexual relationship as seen when she notes that "James never fucked me like this" while Spyro has sex with her, while in most of their original incarnations they are not romantically involved with one another (the exception to this being the manga series The Electric Tale of Pikachu).
Appearance wise, her outfit is missing Team Rocket's "R" symbol on the chest.