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The Boss's Dirty Little Secret date idea illustration

The Boss's Dirty Little Secret

Duration: 2 hours
Budget: any

Get ready for a steamy office affair in this roleplay scenario. Play the boss who can't resist their sexy secretary, and indulge in a forbidden encounter in the office. Will you get caught?

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  • It's a typical Tuesday morning in June, and you, the boss, are sitting at your desk, sipping your coffee and going over some important documents. Your secretary, who is also your partner, walks in with a notepad and pen, ready to take notes. But as she approaches your desk, you can't help but notice how sexy she looks in her tight business attire.
  • You try to focus on the task at hand, but your mind keeps wandering to the dirty little secret you've been keeping from your colleagues - your illicit affair with your secretary. You can't resist the temptation to call her over to your desk, allegedly to discuss some work-related matters, but in reality, you just want to get your hands on her.
  • As she leans in close to take notes, you can't help but whisper naughty things in her ear, making her blush and squirm in her seat. You know you're taking a risk, but you can't resist the thrill of doing something forbidden in the office.
  • The tension between you builds, and you know you need to find a way to release it. You tell her you need to discuss something in private, and she follows you to your office, her heart racing with anticipation.
  • Once you're alone, you can't contain yourselves anymore, and you indulge in a passionate, hurried encounter, trying not to make too much noise and get caught by your coworkers.

Preparation steps:

  • To set the scene, you'll need a suitable office space. You can transform your home office or a spare room into a professional-looking office with a desk, chair, and some office supplies. Make sure to add some props like files, papers, and a notepad to create a realistic atmosphere.
  • Dress the part by wearing business attire, like a suit and tie for the boss, and a tight business dress or a blouse and skirt for the secretary. You can also add some accessories like a tie clip, cufflinks, or a statement necklace to complete the look.
  • To add an extra layer of realism, you can create a fake company name and logo, and even set up a fake meeting or appointment to 'discuss' during your roleplay.

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Some tips:

  • To really get into character, try to establish a clear power dynamic between the boss and the secretary. The boss can be more dominant and assertive, while the secretary can be more submissive and obedient.
  • Use the office setting to your advantage by incorporating office supplies into your play. For example, you can use a pen or pencil to tease and tantalize each other, or even use a stapler as a makeshift sex toy.
  • To make the roleplay more believable, try to stay in character throughout the scenario. Avoid breaking character or using your real names, and instead use your character names and titles.

Dialogue ideas:

  • I hope you're ready for a long, hard meeting, because I have a feeling it's going to be a wild ride.
  • Oh, I think we need to discuss the Smith account in private, don't you, darling?
  • You're looking particularly stunning today, secretary. I think you need a little...motivation to get through the day.
  • Your notes are always so thorough, but I think you might be missing one or two...vital points. Let me show you.
  • Come closer, baby, I need to whisper something in your ear. Don't worry, it's just a little office secret...

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