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The Boss's Sunset Appraisal

Duration: 1-2 hours
Budget: $0

In this roleplay scenario, the man acts as a powerful boss who's scheduled a 'special appraisal' for his employee, played by the woman, in a secluded outdoor setting. The dynamic involves him asserting his dominance while maintaining an aura of public discretion.

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  • Decide on a remote yet safe outdoor location that's public enough to imbue the thrill of potential discovery without the actual risk, such as a private corner of a park or an abandoned outdoor space.
  • The boss instructs his employee to meet him at sunset for a 'performance appraisal'. He's firm and authoritative, hinting at consequences if she's late.
  • Once she arrives, he keeps her standing while he sits on a bench, reviewing her 'performance'. He lists outlandish demands and critiques her, interweaving his words with suggestive remarks.
  • The employee must defend her 'work', with each defense leading the boss to propose a more intimate 'team-building exercise'. He insists it's to improve her 'public relations skills'.

Preparation steps:

  • Agree on a safe word before beginning to ensure boundaries are respected, keeping the experience fun and consensual.
  • Dress for the part: she could wear business casual attire, something she feels sexy in, yet inconspicuous to the public eye. He should aim for the authoritative look of a boss, with a suit or smart shirt.
  • Scout an outdoor location beforehand, checking for both privacy and minimal risk of interruption to prevent any real-world complications.

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Some tips:

  • Discuss the intensity of humiliation beforehand and agree upon the extent to ensure a comfortable and pleasurable experience for both.
  • Incorporate the natural surroundings into the roleplay, using elements like the setting sun or a gentle breeze to add sensory details.
  • Hydrate and protect yourselves against outdoor conditions, like mosquitoes and sudden weather changes, to avoid discomfort.

Dialogue ideas:

  • Boss: 'Your work has been rather unsatisfactory; tell me, how willing are you to go above and beyond for your job?'
  • Employee: 'I am ready to do whatever it takes to prove my loyalty to the company, Sir.'
  • Boss: 'Good, let us begin with your ability to maintain composure under intense scrutiny...'

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