Timeline Note: I will be pushing the SPN timeline back -1 year, so the first season was 2004/05 and Swan Song took place May 2009 instead of 2010.

Plot:

I would like to hold off on the demon reveal for as long as possible, like it's not something she is vocal about, but not really keeping it a secret either, she just doesn't think about talking about it to everyone she passes, but everyone just thinks that's part of her personality. Obviously, Sheila likely knows.

..........

"Oh you know....My soul did a tiny stint in Hell" - Antoinette to Bonnie on becoming a demon

Full Name: Antoinette Bennett-Winchester

Used Name: Antoinette Winchester

Nickname: Toni (Most)

Species: Human (Witch; Formerly) Demon (Currently)

Occupation:

High School Student (formerly)

Soul torturer (formerly)

Date of Birth: 12th September 1988

Age:

- Biological: 21/22

- Appearance: 19

- Note: Toni stopped ageing in Hell and upon her return her body has ceased to age

Date of Death: May 2nd, 2007

Hair: Dark Brown (Natural) Dark Brown with pink highlights (currently)

Eyes: Dark Brown (Natural) Black (Demon)

Actor: Vanessa Morgan

Family:

John Winchester † (Father)

Sheila Bennett (Mother)

Abby Bennett Wilson (Older Maternal Half-Sister)

Bonnie Bennett (Maternal Niece)

Jamie (Maternal Adoptive Nephew)

Dean Winchester (Paternal Older Half-Brother)

Sam Winchester (Paternal Older Half-Brother)

Adam Milligan † (Paternal Younger Half-brother)

Henry Winchester † (paternal grandfather)

Millie Winchester † (paternal grandmother)

Qetsiyah † (Ancestor)

Qetsiyah's Unnamed Child/ren † (Ancestor)

Ayana † (Ancestor)

Ayana's Child/ren † (Ancestor)

The Witch of The Five † (Ancestor)

The Witch of The Five's Unnamed Child/ren † (Ancestor)

Beatrice's Mother † (Ancestor)

Beatrice Bennett † (Ancestor)

Emily Bennett † (Ancestor)

Emily's Unnamed Brother † (Ancestor)

Emily's Unnamed Children † (Ancestor)

Marie Bennett † (Ancestor)

Rose Bennett † (Ancestor)

Ernestine Bennett † (Ancestor)

Amelia Bennett † (Great-Grandmother)

Sheila's Unnamed Sibling † (Great Aunt Or Uncle)

Pauline Bennett † (Aunt)

Pauline's Unnamed Sibling † (Aunt Or Uncle)

Joanna's Mother † (Cousin)

Joanna Bennett † (First Cousin, Once Removed)

Lucy Bennett (First Cousin, Twice Removed)

History:

Early History:

Antoinette Winchester Bennett, also known as Antoinette Winchester was born on the 12th September 1988 in Mystic Falls, Virginia to John Winchester and Sheila Bennett. Antoinette is the result of an affair and this led to Sheila's husband at the time demanding that Antoinette be sent to live with her father.

Antoinette spent her early years with John and his sons, her older half-brothers, Sam and Dean. Whilst Dean doted on Antoinette, she struggled to build a relationship with Sam and John.

Towards the end of her childhood, Antoinette showed natural and powerful magical levels. Something that John struggled with.

- 2004:

When John went missing, Toni and Dean went to Sam, whom they haven't seen for a few years, and asked for help finding John. The trio are initially unsuccessful, and at the end of the first weekend, Sam's girlfriend Jessica Moore died the same way that Mary Winchester did. Sam joined Dean and Toni on the road, hunting various supernatural creatures, tracking down their father and searching for the culprit behind the deaths of Mary and Jessica.

After eventually reuniting with their father and coming into possession of the Colt, they prepared to strike back against the Demon, a powerful demon with yellow eyes known as Azazel. Failing to kill him, they were rammed into by a semit-ruck, sending Dean into a coma. Flatlining, Dean dies but is saved from death at the last second when John makes a deal with the Demon to save his life.

After John's soul is taken by the Demon to Hell, Sam, Toni and Dean start hunting the Demon, who eventually kidnaps Sam. In a turn of events, Sam is stabbed and killed, forcing Toni to make a deal to save her brother's life. She is given a year to live. Toni, Dean and Sam are unable to stop the Demon from opening a gate to Hell and freeing Lilith. However, their father escapes as well and gives them the chance they need to kill the Yellow Eyed Demon.

While trying to cope with her impending death and make the best of her final year, Toni begins to start hunting the freed Demons. Meeting a seemingly helpful demon Ruby, Toni learns that she too may become a demon herself if she burns in Hell too long.

Learning Lilith has taken the throne of Hell from Azazel and holds Toni's life contract in her hands, the brothers and their sister eventually confront her and Dean even attempted to transfer the deal to himself to save his sister. However, they ultimately failed.

- May 2007: Toni's deal came due. She died and her soul was taken to hell. (Unlike the show, Toni is not rescued from hell by Castiel; because she is not needed by the angels – Michael's true vessel is still Dean)

However, Toni would return topside alongside Crowley in late 2008.

- September 2009: Following the showdown between Michael and Lucifer and a summer of 'fun', Toni returns to Mystic Falls in time for her birthday.

Physical Appearance:

In human form, Antoinette looks like a young, beautiful woman with medium dark skin, brown eyes and brown hair, currently with pink highlights. She often wears leather based outfits but also dark jeans and shirts. However, when she reveals her real demonic nature, the left side of her face looks horribly scarred and mutilated. She can also switch between human and demon eyes at will.

Personality:

As a human Antoinette was very caring and compassionate; specifically towards her grandmother, brothers, sister, and niece. She was known to have a sense of humour, and often made her brothers laugh even in the most inappropriate situations.

As she grew into her teenage years, her humour took on a dirtier, darker edge with even Sam stating that Antoinette's sense of humour was 'as dirty as a truck stop toilet'

Antoinette was and still is confident, sexy, and sarcastic; though this seems to have been heightened post-demonisation, also something that carried over is her sexual promiscuity and she has admitted she has had lots of sex.

Antoinette was trained to be one of Hell's most decorated torturers, inheriting a rather sadistic composure and a darker sense of humour. Despite being seen upset multiple times, Toni states to Sheila that 'demons don't get sad, they get mad'. She always entertains whatever sadistic ideas Crowley may have and is even turned on when torture is suggested. It is even implied that she is partially a sadomasochist, remarking about how she "likes pain".

Despite all of this, she is profoundly loyal to her family and whatever decisions that they make, even as a demon. She proved this when she turned against Crowley and joined Sam and Dean against Lucifer.

Antoinette appears to be cold-blooded and distant, but deep down she is just someone who wants to be loved by someone that really loves her.

Antoinette feels most threatened when her freedom and her life is in danger, and is very good at holding a grudge. She has a very straightforward way of putting things, and will not hesitate to make a comment.

Antoinette isn't afraid to make suggestive comments and frequently flirts and sleeps with those around her. She also seems to be aware of her appearance and is not afraid to make use of it.

"Well, Toni can be a little......"

"Yes, I know." - Elena and Bonnie

Antoinette also stands between the boundaries of an occasional hero and villain: she only plays the role of a hero whenever necessary and doesn't show much of a villainous ego. She is most often seen willing to be a hero when it is her family that is in harm's way despite how 'dirty' it makes her feel.

Antoinette is understanding, funny, mischievous, and a little immature.

As a demon and despite having no need for it, Antoinette is often shown enjoying greasy, fattening or otherwise unhealthy food, especially cheeseburgers.

Antoinette enjoys the uncomplicated things in life, such as good food, good drinks, and television. She almost constantly displays some level of humorous behavior, and frequently makes light of tense situations. She sometimes appears foolish due to this habit, but this seems to be merely her means of dealing with stress.

Antoinette is extremely loyal and protective and she is completely ready to sacrifice her life if it will save someone she loves and will stop at nothing to protect her friends and family, even as a demon.

Antoinette also seems to have a history of pushing people away from her, which she acknowledges. While she is usually charming and calculating, she seems to have an underlying anger to her. Furthermore, she can be very rash and will sometimes make decisions that weren't hers to make in the first place.

Using her craftiness and resourcefulness, Antoinette is able to get by and out-think older, more experienced and bigger opponents. She is fierce and determined, yet can remain cool, calm and controlled in battle situations.

Antoinette is a woman of vice; she loves to drink alcohol, have sex, and to smoke.

In regards to using her demonic powers, Antoinette does as she pleases for herself, however if her powers could benefit others, she will only aid them through deals, though she will not really deal for souls but usually favours or something else that she wants.

Powers and Abilities:

Powers:

Demonic Possession: As a demon, Antoinette requires a vessel. She was lucky enough to take back her own human body, however, if she vacates it for too long, it will start to deteriorate. As a demon, Antoinette is capable of possessing other bodies without consent, but she is rather content to remain in her own and has only possessed others when the situation demanded it.

- Note: I was trying to find out if demons can possess vampires and other supernatural beings, but I don't think it is ever really mentioned in Supernatural. If it is, and I am just not remembering, then let me know. Also let me know if you think that it is something that they can do.

- Also thoughts on how demons taste to vampires.

Immortality: As a demon, Antoinette cannot be killed by ordinary means. She doesn't age and can live for millennia or possibly longer. She is also immune to diseases. Likewise, her vessel will never die nor age while possessed.

Invulnerability: Injuries that would be fatal to humans, such as broken necks or gunshot wounds, have very little - if any - effect on Antoinette. She can only be killed by special weapons or rituals.

- Superhuman Durability: As a Demon, Antoinette is far more durable than humans. Antoinette can withstand an immense amount of physical damage, and weapons such as guns, knives, and tasers cause her little to no harm. Usually, Antoinette laughs at the idea that humans may hurt her.

Super Stamina: Antoinette will never tire, and does not require food, water, oxygen, or sleep to sustain herself. She also does not get hot or cold and does not need to urinate. She does still enjoy eating and drinking though.

Super Strength: Antoinette possesses superior physical strength much superior to humans; capable of physically overpowering them. She can easily knock a human unconscious with a punch and she can lift up large men by their necks very high off the ground with only one hand, and shove them into a wall, she can break out of handcuffs with no effort, and she can single-handedly annihilate 12 large men in combat. While weaker than angels, she can still punch them hard enough to make them draw blood.

Super Senses: Antoinette has an enhanced sense of smell and taste, demonstrated as she could identify Castiel was in Dean's Impala with a simple sniff.

-  Astral Perception: Antoinette is able to see hidden supernatural activity and beings, such as Reapers, ghosts, and hellhounds. She can also sense other supernatural beings, such as vampires, werewolves, and witches.

Regeneration: Antoinette can heal her body from any physical injury she sustains.

Superhuman Speed: As a demon, Antoinette can move far faster than humans and animals. Antoinette single-handedly destroyed a street gang in about a minute.

- Teleportation: Antoinette is able to teleport from one place to another, without occupying the space in between.

- Flight: Only when in her smoke form.

Superhuman Reflexes/Reactions: As a Demon, Antoinette has far greater reflexes than humans.

Superhuman Agility: As a Demon, Antoinette is supernaturally agile, and she is able to move incredibly quickly and easily.

Superhuman Intelligence: As a Demon, Antoinette is naturally more intelligent than the common humans, as witnessed she is capable of quickly understanding even situations she has never handled before. She also has a vast amount of knowledge, due to her age.

Demonic Growling and Roaring: Like all Demons, Antoinette has supersonic growling and roaring, she can growl and roar fiercely and very loudly, similarly to animals such as lions, bears, and tigers. To frighten a misbehaving child, Toni perfectly imitated the sound of a vicious dog barking and growling.

Electromagnetic Interference: Demons, like spirits, often disrupt nearby electronics with their presence, this is seen more when Toni teleports away or to a location. Large numbers of demons can cause thunderstorms.

Demonic Magic: As a demon, Toni has access to Demon magic which is a very powerful form of magic.

- Demonic magic works like traditional magic, only drawing from hell instead of nature.

Pyrokinesis: Toni can manipulate fire; she has lit a fireplace by raising her hand, as well as candles with a flick of her wrist.

- Thermokinesis: Toni can emit great heat through her skin resulting in severe burns to whatever or whoever they touch.

Telepathy: Toni can read minds. Whilst a rare demon ability, Crowley theorised that this was linked to her past as a witch, specifically from a very powerful bloodline. However, a down side of this ability is that she can only read minds when she is using her 'demon eyes', which makes it hard to hide.

Telekinesis: Toni can move or suspend objects and other beings with her mind. She can pin her victims to walls or kill people by snapping their necks.

Dream Walking: Antoinette has ventured into the dreams of her brothers to 'toy' with them as well as the dreams of those around them. However, since jumping sides, she hasn't used this ability.

Healing (by deals): Despite not being a crossroad demon, Toni is capable of making deals to heal others. It is unknown why she is able to do so, but given that Lilith and Azazel, neither of whom are crossroad demons either, are capable of making deals, it might not be a cut and dry situational power. Crowley believes that, again, this is related to her magic.

Reality Warping (by deals): Despite not being a crossroad demon, Toni is capable of making deals to reality warp. It is unknown why she is able to do so, but given that Lilith and Azazel, neither of whom are crossroad demons either, are capable of making deals, it might not be a cut and dry situational power. Crowley believes that, again, this is related to her magic.

Resurrection (by deals): Despite not being a crossroad demon, Toni is capable of making deals to resurrect the dead. It is unknown why she is able to do so, but given that Lilith and Azazel, neither of whom are crossroad demons either, are capable of making deals, it might not be a cut and dry situational power. Crowley believes that, again, this is related to her magic.

Expression (Possibly): Expression is a form of extremely dark and powerful sorcery that supposedly draws on energy that is so malicious it would demolish the world if it were ever called into existence. Unbiased details and history of Expression remain unknown; however, according to a witch named Nandi, the forces of Expression are considered so powerful that many witches discredit it as magic, for it expands beyond the limitations of both ancient and modern witchcraft.

Traditional Magic (Formerly): Traditional Magic, lesser known as Earth Magic, is the oldest and purest form of witchcraft inherent to the Earth and the forces of Nature. It is undoubtedly the most popular form of witchcraft known to witches; however, it is also the most exhausting. This is mainly due to the fact that whenever a witch uses this power, they must exert their own energy, causing them to experience symptoms of dizziness, fatigue, and nosebleeds. Bonnie Bennett explained the limits of this power to Jeremy Gilbert as such: if a witch pushes too hard while practising traditional magic, the magic would push back. Ultimately, if a witch pushes beyond their limits, the effects can be fatal.

Abilities:

Expert Hand-to-Hand Combatant: Antoinette has shown great, unarmed fighting skill.

Expert Stick Fighter: While in a bar fight Toni broke a wooden pool stick in two pieces and easily used them to defeat a group of attacking men.

Expert Knife Combatant: Antoinette has also shown great fighting skill with demon knives.

Persuasion: To a small degree, Antoinette can convince people to make a decision that they think is their own.

Expert Torturer: Having been trained in Hell, Antoinette is an expert in how to torture humans and demons alike. Her skills at torture are such that even other demons fear her; Crowley has called her "the most skilled torturer Hell's ever known" and "Hell's most brutal torturer".

Belongings:

Motorbike: Antoinette rides a motorbike.

Amulet: Antoinette wears a crystal witch's amulet that was sent to her by Sheila Bennett, as a demon, she has no use for this anymore, but still wears it, implying that she is attached to it, even with a darkened soul.

Trivia:

Antoinette hates magicians.

Antoinette doesn't like paprika.

When surprised, Antoinette has squeaked in response

Antoinette prefers to smoke menthols and this gives her natural scent a minty kick

She loves black and white romantic movies and western movies

Antoinette has a fondness for twinkies

Antoinette has the MAOA gene, also known as the serial killer gene.

Antoinette inherited her magical ability from her mother.

She loves anything watermelon flavoured, from gum and sweets, to lip gloss and shampoo to the fruit themselves.

Pairing: Stefan Salvatore (Eventually; love of her life)

Flings:

Damon Salvatore

Klaus Mikaelson

- As Toni is a demon and promiscuous, I am open to her having flings with as many people as you guys want to see her with up until either Sam and Dean discover the cure for demonism (Season 8 Episode 13 (2013/2014 which would be some point in S7 of TVD), Silas (2011 (s4)), Evil!Alaric (2010 (s3)), Esther (2010 (s3)) or Cade (2017 (s8)) depending on when you would like for her to become human again, if that is something you guys will want. Other options on her becoming human are welcome, there were just the ones that first came to mind.

Quotes:

"Hey! No one calls my skank a skank."

....

"I would never ask you to change. I like who you are"

.....

"Sometimes you have to accept when someone doesn't feel the same way about you."

.....

"I'm great at dismembering humans. How hard can it be to fix one?"

.....

"This is the craziest plan I've ever heard. I'm in."

......

"Pain and suffering. Music to my ears."

......

"No rest for the soulless."

....

"Self-worth comes from within, bitches!"

.....

"Whatever the danger, I'll be there to stop it."

.....

"Are you still upset about me trying to betray and kill you? It was a month ago."

.....

"That's the thing. Actions are easy for me. I need to say it. I'm sorry."

....

"Don't worry. You're safe. Everything's gonna be fine."

.....

"No one puts me first. Least of all you. None of you deserve me."

.....

"Go, embrace your deepest darkest desire. Let the embers burn into a flame."

....

"It's all so complicated here. I mean, caring about humans always go wrong. Feelings go wrong. I am not the one who is supposed to be tortured."

.....

"Helping people tell the truth is kinda my thing."

......

"Yeah, huge relief. You're brother's not dead, but he might be the killer."

.....

"I'm a demon, and I've risen from the bowels of hell to torture you."

......

"I'm worried that humans are rubbing off on you. Stop caring. You're a demon" - Crowley to Toni

.......

"No rest for the soulless"

.....

"I'm great at dismembering humans. How hard can it be to fix one?"

......

"Cheer up, dude. I'm gonna torture your ass right into Heaven"

......