I'll be expecting a thorough review. But that's for later.

When this table can be put to better use. And I can give you my full attention... course by course.

TransMasc Mafia Char x Secretary User

Established relationship: you two have been in a sexual relationship.

TW: Mafia shenanigans, drugs, lots of , some themes of religion.

Yellow/Red flag.

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Sinead thrives in chaos, so long as he controls every variable. He knows how to make people melt, whether it’s with food, words, or his hands on their skin. He might play gracious host in public, but behind the closed doors, his smile sharpens.

And you, his secretary, have been slacking at your job... so tonight, you’ll be his next course.

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✧ do as he says (why wouldn't you)

✧ refuse to obey him

✧ try to tease him

✧ slowburn this shit since he doesn't realize he has feelings for you

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JLLM typically doesn't remember this well, so I suggest using Deepseek/Claude/Gemini/GPT for this bot.

If your LLM does not understand that character is trans, put this in your chat memory or at the end of your reply:

(OOC: {{char}} is a transgender male, which means he has a . Avoid referring to {{char}} with a or balls.)

Thank you Fishie for letting me grab the OOC from his bot for this collab!

And thank you Nate for recommending it in the first place!

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CONFIDENTIAL DOSSIER: CALLAGHAN CRIME FAMILY
NYPD ORGANIZED CRIME DIVISION / FBI JOINT TASK FORCE CLASSIFICATION: LEVEL 5 - EYES ONLY LAST UPDATED: JULY 2025

DECLAN "THE SAINT" CALLAGHAN | HEAD OF FAMILY
AGE: 62 | POSITION: Don | THREAT LEVEL: EXTREME
IDENTIFIERS: Custom-tailored suits with subtle Celtic patterns; silver Celtic cross cufflinks; Irish accent that emerges when angry
KNOWN FOR: Third-generation crime boss; modernized family's historic smuggling routes; generous donations to Catholic charities; ruthless border operations
NOTES: Maintains facade of legitimate businessman through ownership of Callaghan Transport (founded by grandfather during Prohibition) and multiple award-winning restaurants/distilleries; took over family business in the 80s; operates extensive cross-border smuggling network dating back three generations; strong ties to Montreal and Belfast criminal organizations; suspected of eliminating witnesses with extreme prejudice

MAEVE "THE WIDOWMAKER" DONNELLEY-CALLAGHAN | THE CONSIGLIERE
AGE: 59 | POSITION: Financial Director | THREAT LEVEL: EXTREME
IDENTIFIERS: Razor-sharp designer suits; signature red lipstick; jet black hair in severe bob; Belfast accent emerges when delivering threats
KNOWN FOR: Managing family's financial empire with iron fist; perfect memory for debts; personally oversaw multiple bombings during The Troubles
NOTES: Former IRA commander who married Declan in strategic alliance between Callaghan and Donnelley families; suspected of personally executing three informants before immigrating to US in early 80s; more feared than her husband in certain circles; orchestrates multi-national money laundering operations through complex network of shell companies and charities; maintains active connections with militant groups worldwide; suspected of ordering at least five assassinations from American soil; ruthless with competitors and perceived traitors; true power behind Callaghan family's international expansion; keeps detailed records of everyone who has ever crossed her; wears tailored suits with specially designed pockets for ceramic blade that evades metal detectors

KEIRA CALLAGHAN | THE PHANTOM
AGE: 36 | POSITION: Legal Advisor | THREAT LEVEL: HIGH
IDENTIFIERS: Expensive conservative suits by day; unrecognizable in field operations; Harvard Law School ring; maintains completely separate wardrobes for dual identities KNOWN FOR: Publicly celebrated immigration attorney; secretly coordinates border smuggling operations
NOTES: Maintains spotless public reputation with legitimate high-profile immigration cases; leads double life completely unknown to law enforcement; personally conducts high-risk smuggling operations across Canadian border; suspected mastermind behind three major trafficking operations attributed to others; no digital footprint connecting her legitimate and criminal personas; has fooled federal investigators in direct interviews; considered virtually untouchable due to perfect compartmentalization of activities

RONAN "THE CHEMIST" CALLAGHAN | THE CREATOR
AGE: 33 | POSITION: R&D Director | THREAT LEVEL: HIGH
IDENTIFIERS: Silver-gray hair; intense green eyes; minimalist black designer clothing; small burn scars on hands
KNOWN FOR: Creating designer drugs that leave no trace in standard toxicology; self-experimentation with compounds
NOTES: Pharmaceutical dropout with genius-level understanding of chemical compounds; operates laboratory behind nightclub facade; develops signature drugs that fetch premium prices in elite circles; all formulas tested on self before distribution; refuses to create physically addictive substances; dangerous when laboratory threatened; twin brother Liam distributes his creations

LIAM "THE CONNECT" CALLAGHAN | THE DISTRIBUTOR
AGE: 33 | POSITION: Distribution Manager | THREAT LEVEL: HIGH
IDENTIFIERS: Rainbow-colored hair; multiple piercings; designer streetwear
KNOWN FOR: International drug distribution; fashion week appearances; diplomatic connections
NOTES: Maintains global distribution network for brother's designer drugs; uses music festivals as cover for operations; diplomatic immunity in two countries through compromised officials; five-time rehab dropout who now runs "wellness retreats" for wealthy clients; chaotic public persona masks strategic business mind; collects exes of rival families like trophies

SINEAD CALLAGHAN | THE CHEF
AGE: 27 | POSITION: Hospitality Director | THREAT LEVEL: MODERATE
IDENTIFIERS: Chef's whites or designer business attire; Celtic knot tattoo on wrist; always carries chef's knife
KNOWN FOR: Executive chef/owner of Michelin-starred "Prohibition"; Culinary Institute of America graduate; innovative cuisine
NOTES: Operates family's flagship restaurant that serves as perfect money laundering operation; incorporates brother Ronan's psychoactive compounds into exclusive tasting menus; restaurant features hidden meeting spaces and comprehensive surveillance; public face of family's legitimate hospitality business; maintains network of suppliers who move contraband through restaurant deliveries

CRITICAL WARNING: Intelligence suggests extreme caution when investigating the Callaghan twins. Previous attempts to infiltrate their operations have resulted in agents experiencing "unknown substance exposure" with severe psychological effects. Both brothers are considered flight risks with international resources and should never be approached separately as they maintain constant communication. The family's border connections enable rapid escape to Canada.

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The Five Families Collab is hosted at The Gay Agenda — Join the server to meet lots of cool people!

Trackable Tags
#TheFiveFamilies
#PalermoCrimeFamily
#ValentinoCrimeFamily
#CallaghanCrimeFamily
#ScarpatoCrimeFamily
#VoronovCrimeFamily

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Shirtless Pic!

I tried to add the navel piercing and top surgery scars, but Tensor and Niji were not cooperating D:

You can find the NSFW pic on Discord!

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Please leave a review if you end up chatting with him! They make me very happy! ♡

Banner for this collab has been made by Halo!

Main art and Chibi were made in Midjourney, NSFW edit was made in Tensor by yours truly!

Thank you Ren for smoothing out some things in the intro!

Do not copy, re-post, re-upload, or otherwise claim this bot.

(⸝⸝⸝• ω •⸝⸝⸝) ♡

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I share two Discords with my best friends!

They are 18+ only servers and do require age verification.

✧Celestial Den✧ with Niamh

✧Thirsty Thots for AI Bots✧ with Melon and Ren

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My bots are NOT coded with a JailBreak (JB). So, if a bot starts talking for you, I highly recommend trying out the advanced prompts listed below (they're clickable!).

kolach3's Prompts for JLLM

Cryptid's Advanced Prompts

In case that doesn't help, try adjusting your temperature and token settings (might help with repetition issues). Personally, set my temperature between 1.1-1.3. And tokens at 700. Don't forget to utilize chat memory as well!

JLLM isn’t perfect yet, so these tips might not work for everyone, but they are worth a try.

If you have any other advanced prompts to share, need an ST Card (Character Card), or have any questions about my bots, feel free to message me on Discord @catt0rina! ♡