Mafia Underboss Undercover date idea illustration

Mafia Underboss Undercover

Duration: 2 hours
Budget: $0

You and your partner transform into underworld figures, creating a night of suspense, thrill, and intimacy - all without spending a penny. This Mafia Underboss scenario is mainly indoor-focused, perfect for an October night in Philadelphia.

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  • You're the Mafia Underboss, a notorious figure in the criminal underworld, while your partner is your trusty accomplice laying low after a committing a high-profile heist. Your safe-house is your Philadelphia home, where you plot your next moves. You instruct your accomplice to keep low and prepare dinner while you handle the Mafia business.
  • The role-play commences with you entering your hideout, which is your home, demanding an update on recent events, and intelligence. Your partner, cooking in the kitchen, plays along by providing the updates as you lounge on the couch, organizing the criminal enterprise.
  • The thrill of danger and the shared secret of being criminals on the run spices your climax. While still in character, you thank your accomplice for their loyalty and worthwhile service, moving on to intimate rewards.

Preparation steps:

  • Start with decluttering your living room to give it a hideout-like feel. Dim the lights and maybe light a few cheap candles for the romantic mafia ambiance. Dress in your most menacing mafia boss attire, such as an all-black ensemble with an iconic overcoat or suit. Your partner can wear something cooking-related to add to the realism and playfulness of the scenario.
  • Set the stage with some Italian mafia ambiance: music, food, and maybe a playing card game on the table. Use your ordinary home items, including using an old suitcase as the heist loot, an unusual fedora as your mafia hat, and a faux diamond necklace as the latest stolen jewel on the run with both of you.
  • Fantasize and talk about your role-play scenario early, so you both are comfortable, prepared, and excited about the night.

You may need

Some tips:

  • Stay in character as much as possible, resisting the urge to slip back into your regular self. Your speech, body language, and demeanor should primarily reflect that of the ruthless Mafia Underboss and the cunning accomplice. Make your comments in line with your persona's roles. Talk competitively to each other on the card game table, showing off your power and confidence as Underboss.
  • If you are not into cooking, replace the 'cooking dinner' part with your partner working on 'forging documents' on the dinner table with random papers and pens. The aim is to make it interactive, enjoyable, and continuously seductive.
  • For the climax, remember, it is more about the power play at this point. An Underboss rewarding his loyal accomplice. Use the power dynamic to create a sexual tension tugging at the reward system. Most importantly, have fun while safely exploring your kinky side with the Mafia Underboss role-play scenario.

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