#Don Marion Anthony D'Amico

[wei-smiler]

I really think the goons or the wise guys from the Simpsons would be very great in your art style just a request :)

I tried it. I hope you like it_(:з」∠)_

[rolkstone]

The DiMaggio Crime Family info

(this is based on my AU which I have been developing with @fernikart57 and @ghosttrickfan9887 )

The Big Boss: Joel Fontana (OC by Fernikart57)

He comes from a long line of men of the same name. The first one came to the US to find a better life; his son found a much better life in crime, which he in turn taught to his own son. This current Joel is the fourth in the line and is perhaps the most bitter and angry, due to his extremely toxic upbringing and the feeling that no one likes him.

He eventually takes a seat on the Mafia Commission and spends more time in other cities, but he got his start in Springfield.

The Boss: Don Vittorio DiMaggio

His ancestor had come to the US with the first Fontana to help get them set up. Vittorio has always been a very level headed, calm, almost sweet man who found a lot of solace in his friendship with Fat Tony. He was groomed to be the boss since middle age and carefully, quietly, led things under Joel's eye. Eventually he takes over the DiMaggio crime family in Springfield and New Jersey.

He found love in his earlier age but because he was in love with another man, his father went nuclear. Vittorio had to leave his love forever. Now he continues to stay away from men romantically and collects cats.

The Underboss: Marion Anthony "Fat Tony" D'Amico

His ancestors worked faithfully alongside the DiMaggios; Tony was a sort of Mafia prince from a young age. He had everything going for him and he really embraced it. He was close with Vittorio from the start and took pride in being a good enforcer for him.

He later meets a woman named Anna Marie and they hit it off almost immediately. He later has a son with her; she dies later.

Since Don Vittorio is a very hands-off leader, Tony is seen to be the boss of the crew by many. Tony does not at all mind getting his hands dirty or helping his men do tasks that usually only peons do.

He's always been a bit chubby, but as he aged he put on the pounds. He's content with that.

The Consigliere: Armin Tamzarian aka Seymour Skinner

Seymour started his life as a criminal, but when he joined the Army, he seemed to put that behind him, especially when he met a man who inspired him to do better. He became the principal of the elementary school and an important figure in the society. But as time went by and the school funds dried, Seymour desperately turned to the Mafia for a loan.

Since he couldn't pay it back in money, Tony allowed Seymour (after having a cute meeting at a restaurant) to pay him back via tasks, like administrative or other nerdy jobs. Eventually they fell in love and a lot more responsibility was thrust upon Seymour.

He's gone through a lot with Tony, lost a lot, gained a lot. He's changed quite a bit, but is still the same sweet, deferential man he's always been.

The Co-Consigliere: Dan Gillick

He started working for the Mafia when he walked in on his old boss talking to some goons. He was threatened and promised to stay quiet. He was always good with numbers; eventually his boss "gave" him to the Mafia.

The mobsters never really respected Dan, especially as he tried to get them to curtail their spending. He had to make sure they weren't hemorrhaging money. At least because he's such a little, frail guy, no one tried to get physical with him. Don Vittorio respected and liked him a lot.

The Top Enforcer: Giovanni "Johnny Tightlips" Silencio

He was part of Carina's (more on her later) crew in New Jersey, still under the umbrella of Don Vittorio and Joel. Johnny was transferred down to Springfield after a series of gang wars took out of a lot Tony's men. Johnny was always so cool and sharp and aloof; Tony had a man-crush on him from the start and still admires him. However, the two can often butt heads as Johnny has a rather independent spirit.

Enforcer: Paulie (OC by me)

He's an older member, a middle ranking capo who's been stagnating in that rank for years now. He's bitter and resentful but decent at his niche job: making collections for the Numbers Game. He often works alongside another mobster.

Enforcer: Jimmy "The Scar"

He's been with Tony from the beginning, though in his early days he was ordered by Joel to spy on his own colleagues. This made him quite unpopular, but when he took the order to pretend to be a cop so he could spy on them, he started to regain some esteem. He's always been level headed and calm and pretty easy going; the guys end up liking him despite his ugly beginnings.

Enforcer: Max "Legs" Legman

He has an explanation for his nickname; he just never gets the chance to tell it. He's one of the few trans members of the crew, and no one knows until the information is forced out of him later. Probably due to an injury. This is partly why he is very stand-offish and touch averse.

He ran away from home at a young age and met Louie, another young runaway. They did what they had to to survive; eventually Louie was picked up by the local Mafia crew due to his Italian heritage. Legs is not Italian, but Louie made it clear they are a two part deal. Now Legs is the crew's medic, having a special talent for it.

Enforcer: Louie

Brash, thoughtless, careless, but with a good heart for a life of crime. He loves Legs but sense how he pulls away; he is constantly trying to get close, then pulling away. He's almost gotten whacked before due to his mistakes, but so far squeaks by because he's willing to do just about anything for Tony.

Peon: Frankie "The Squealer" Veloce

By all rights, he should be dead many times over. He has a compulsion to spill secrets, the more important the more it physically hurts him to keep it in. He is deeply insecure and painfully aware of how "little" he is, in many ways. He just wants to feel big; he wants to feel like he matters. His biological family has always been distant and sort of just pushed him into the Mafia.

Sometimes Tony sends Frankie to the cops to squeal about less important things to distract them.

Peon: Carmine Veloce (OC by me)

A recent member. He's trans and has no idea what he's doing. He barely passes but if the other guys realize, they don't say anything directly about it. He's usually made to do shit jobs like cleaning up and dissolving dead bodies. He's Frankie's cousin, but Frankie doesn't know about his new identity.

The New Jersey Crew

Led by Carina D'Amico, this satellite crew runs things in Newark, New Jersey for the benefit of Don Vittorio and Joel. The crews are primarily independent of each other though will sometimes visit each other or join up for battles.

Boss: Carina D'Amico (OC by me)

She was born Silvio D'Amico, and was raised as a Mafia prince alongside her brother Tony. She was sent to New Jersey as a youth to establish a crew there. She ruled her crew with an iron fist as Silvio for many, many years, knowing something was wrong but afraid to address it in this extremely toxic and macho world of the Mafia.

She started transitioning only recently. There are many in the Mafia who still know her as Silvio, though few make the mistake to call her that. Don Vittorio admires her a lot and has set the standard for his entire Family to respect her.

Underboss: Fausto

A hot headed man whore with many boyfriends, Fausto is Carina's trusted leg breaker. He's her main enforcer. He's tough and brittle, but there's a sensitive heart down there somewhere.

Consigliere: John Lawson (OC by Fernikart57) (not pictured)

More level headed, but also very cruel. He keeps the books for Carina. He is too fragile to fight physically, but his ability to run numbers in his head makes him scary to debtors.

Medic: Layla "Flake" (OC by me)

She got involved with the Mafia when her brother took a job from the wrong man and got imprisoned. She went into debt trying to help him. She met some peons who worked for Carina and eventually met Carina herself, offering whatever she could do instead of money. She's been studying to be a doctor, but was stopped by lack of funds. Carina pays her well now, but keeps her on call at all times.

Enforcer: Floyd (OC by Fernikart57)

A sensitive, careful guy. He lost his arm in a battle; however is the primary driver for the crew in their modified car.

Enforcer: Gregorio

A nasty middle aged guy. He's a smooth talker, a real lady killer, but he's genuinely violent with them too.

[littleoddwriter]

Fat Tony nsfw headcanons maybe? I feel like he would love his s/o calling him by his actual first name

Don Marion Anthony "Fat Tony" D'Amico x GenderNeutral!Reader | N/SFW Headcanons

Hi there! Thanks for the request, I hope you like these! (Also, you're absolutely right.) <3

notes; Bottom!Gender Neutral!Reader; Sexual Activities; Penetrative Sex.

Definitely touches you all over your body at any given time, but only goes into dirty territories when you're making out and you're alone. He values his and yours privacy after all; even if he doesn't particularly care if someone sees him grabbing your ass - that's slightly different for him.

Loves it when you call him by his first name; especially in a sultry tone, it gets him really going. And when you moan or scream his name during sex, he's sure to not be able to hold back much longer.

Wants you to sit on his lap at all times, basically. He just loves feeling your weight on top of him and being able to hold you, while also having the opportunity to get you off and even fuck you so easily, if no one is around.

He's very fond of making love to you. It's his favourite thing to do to let you know how much he loves you, because he feels like nothing else conveys it as well as making slow, tender love to you.