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The Boss's Whim date idea illustration

The Boss's Whim

Duration: 3 hours
Budget: $0

Experience the intense roleplay as a powerful CEO training a stunning new employee, navigating through a day of office professionalism blurred by irresistible attraction, culminating in a seductive after-work encounter.

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  • You're the CEO of a prestigious company, and your new employee, a stunning beauty, has just walked into your office for her first day of training. You can't help but notice the way her curves fill out her business attire, and you can't wait to get your hands on her. As you begin her training, you make it clear that you're a demanding boss, and she'll have to prove herself to you in more ways than one.
  • You start by explaining the company policies and procedures, but your eyes keep drifting to her cleavage, and you find yourself getting distracted. You clear your throat, trying to composed yourself, but you can't help but wonder what she'd look like bent over your desk. You decide to take a break, and as you stand up, you 'accidentally' brush your hand against her thigh, sending shivers down her spine.
  • As the training continues, you become more and more demanding, pushing her to her limits. You make her work on a project, and as she struggles to meet your expectations, you offer to 'help' her, your hands lingering on her skin as you guide her. You can feel the tension between you building, and you know it's only a matter of time before you give in to your desires.
  • You call her into your office, claiming you need to discuss her progress, but really, you just want to get her alone. You shut the door behind her, and as you lean in close, you can smell her perfume, and your cock starts to harden. You whisper in her ear, telling her exactly what you want from her, and as she nods, you know you're in for a wild ride.
  • As the day comes to a close, you 'offer' to take her out for a drink to celebrate her first day. You know it's just an excuse to get her into a more relaxed atmosphere, where you can really let your guard down. You take her to a secluded bar, where you can be alone, and as you sit down next to her, you know it's only a matter of time before you make your move.

Preparation steps:

  • Set the scene by decorating your office with some sexy office supplies, like a leather-bound desk calendar and a few provocative art pieces. Make sure the lighting is dim, and the air is thick with tension.
  • Dress the part - wear a power suit, complete with a crisp white shirt and a tie. You want to exude confidence and authority. Your partner should dress in a provocative business attire, with a short skirt and a low-cut blouse.
  • Make sure you have some props ready, like a folder full of 'work' papers, and a pen that you can use to 'accidentally' touch your partner's skin. You can also use a glass of whiskey to help loosen things up.

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Some tips:

  • Make sure to stay in character throughout the scenario, using your dominant tone to guide your partner through the training. Don't be afraid to get a little rough, and remember to breathe - it's just a roleplay!
  • Use the office setting to your advantage - there are plenty of opportunities for 'accidental' touches and lingering gazes. Make sure to keep the tension building, and don't give in to your desires too quickly.
  • Remember to communicate with your partner throughout the scenario, making sure you're both comfortable and consenting. And most importantly, have fun - this is a chance to explore your kinkier side and get a little wild!

Dialogue ideas:

  • I think you're misunderstanding me, sweetie. This isn't about the project, it's about you proving yourself to me. And I'm not just talking about your work skills.
  • Why don't we take this conversation somewhere a little more private? I have a feeling we can come to a mutually beneficial agreement.
  • You know, I think we've had enough business talk for one day. How about we discuss something more... personal?
  • Are you sure you can handle the demands of this job, or do you need some one-on-one instruction?
  • Let me show you how it's done, my way. And don't worry, I'll make sure you're properly trained in all aspects of the job.

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