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CEO's After-Hours Assistant date idea illustration

CEO's After-Hours Assistant

Duration: 2 hours
Budget: any

Deliver papers to the CEO's mansion and try to resist your growing attraction as the evening unfolds in this steamy roleplay scenario.

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  • As the sun sets on this Tuesday evening in May, you, the CEO's assistant, arrive at his sprawling mansion, papers in hand. You've been working late to finalize the Johnson report, and your boss requested you deliver them personally. You can't help but feel a flutter in your chest as you step out of your car and onto the driveway. You've admired your boss from afar, and the thought of being alone with him in his opulent home sends a thrill through your veins.
  • You ring the doorbell, and the sound echoes through the grand foyer. Your boss answers, looking every bit the powerful executive in his tailored suit. His eyes narrow as he takes in your appearance, and you feel his gaze like a warm touch on your skin. 'Ah, excellent work, as always,' he says, his deep voice sending shivers down your spine. 'Come in, I'll review the papers in my study.'
  • As you follow him through the lavish hallway, you can't help but notice the way his suit accentuates his broad shoulders, the confidence with which he carries himself. You feel your palms grow sweaty, and your heart races with anticipation. What will happen once you're alone in his study?
  • The study is dimly lit, the only sound the crackling of the fireplace. Your boss gestures for you to take a seat, and you do, trying to appear professional despite the growing arousal between your legs. He begins to review the papers, his brow furrowed in concentration. You can't help but wonder if he'll notice the way your nipples are straining against your blouse.
  • As he looks up, his eyes lock onto yours, and you feel a spark of electricity. You know, in that moment, that you're both thinking the same thing. This is not just a routine delivery; this is an opportunity for something more.

Preparation steps:

  • Set the mood with some soft, sultry lighting. Dim the lights, and light some candles to create a warm, intimate atmosphere.
  • Dress the part: the assistant should wear a professional outfit that accentuates her figure, perhaps a fitted skirt and blouse. The CEO can wear a tailored suit, complete with a crisp white shirt and tie.
  • To add an extra layer of realism, have the assistant bring a folder with some papers and a pen, complete with some scribbled notes. The CEO can have a glass of scotch or whiskey nearby, to add to the 'after-hours' vibe.

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Some tips:

  • To really get into character, practice your professional assistant persona beforehand. Walk into the room with confidence, and try to maintain that composure even as the situation becomes more heated.
  • Don't be afraid to improvise. The CEO can 'accidentally' brush against the assistant, or the assistant can 'accidentally' leave her hand on his as she hands him the papers. The key is to keep the tension building.
  • Remember, consent is key. Make sure you and your partner are comfortable with the scenario and the boundaries you've set. Communication is essential to a fun and sexy roleplay.

Dialogue ideas:

  • Your house is even more impressive than I imagined, Mr. CEO. But it's not the only thing that's caught my attention,
  • Oh, I'm glad you're pleased with the report, sir. I've been thinking about it all day... and other things too,
  • You know, I've always wondered what it's like to be more than just your assistant. To be your partner... in every sense of the word,
  • I've never been one to mix business with pleasure, but I think I'm ready to make an exception. For you, sir.
  • I've been feeling a little... restless lately. I think I need something to take my mind off work,

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