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The Boss's Ultimatum date idea illustration

The Boss's Ultimatum

Duration: 2 hours
Budget: any

You're a secretary who's messed up a crucial project and now your boss is furious, threatening to fire you. But as the tension builds, you sense a different kind of emotion from him, one that could change everything. Will you do whatever it takes to keep your job?

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  • It's a typical Thursday afternoon in November, and you're sitting in your boss's office, nervously fidgeting with your hands as he glares at you from across the desk. He's been going over some papers, muttering to himself, and you can sense the tension building up. You're his secretary, and you've been working for him for a while now, but somehow, you've managed to mess up a crucial project, and now he's furious.
  • He slams his fist on the desk, making you jump in your seat. 'You're a disaster, a complete and utter disaster,' he growls, his eyes blazing with anger. 'I should fire you on the spot, but I'm going to give you one last chance.'
  • You swallow hard, feeling a mix of fear and excitement coursing through your veins. You know you've messed up, but a part of you hopes he'll take mercy on you, that he'll see the good in you, and maybe even... maybe even take advantage of the situation.
  • He leans in, his face inches from yours, his hot breath on your skin making you shiver. 'But first, you're going to have to prove yourself to me. Are you willing to do whatever it takes to keep your job?'
  • You hesitate for a moment, unsure of what to say, but then you look into his eyes, and you see something there, something primal, something that makes you feel like you're in way over your head. And yet, you can't help but feel drawn to it, like a moth to a flame.

Preparation steps:

  • Make sure you're both comfortable with the roleplay scenario before starting. You can even discuss the details beforehand to make sure you're both on the same page.
  • Set the scene by creating a mini office space in your home. You can use a desk, a chair, and some papers to create a realistic atmosphere.
  • Dress the part, too. The secretary can wear a sexy office outfit, complete with a short skirt and heels, while the boss can wear a suit and tie to complete the look.

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Some tips:

  • Remember to stay in character throughout the roleplay. The boss should be dominant and assertive, while the secretary should be submissive and eager to please.
  • Take your time, and don't rush through the scenario. The build-up of tension and anticipation is what makes this roleplay so hot.
  • Don't be afraid to get creative and add your own twists to the scenario. The more you improvise, the more realistic it'll feel, and the hotter it'll get.

Dialogue ideas:

  • You're going down, secretary. All the way down. Do you want to keep your job?
  • If you want to stay employed, you're going to have to do a lot more than just type and take dictations. You're going to have to take my dick.
  • You've disappointed me for the last time. Now, you're going to have to suck it up to keep your job.
  • You're a mistake, a mistake I'm going to rectify right now. On your knees, secretary. Show me what you're made of.
  • You're lucky I don't fire you on the spot. Now, take off that blouse and show me why I shouldn't.

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