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The CEO's Personal Assistant date idea illustration

The CEO's Personal Assistant

Duration: 2 hours

In this thrilling office roleplay, a shy worker, Emily, is summoned to the CEO's office for a 'personal meeting'. As the powerful Mr. Johnson towers over her, their encounter takes an unexpected turn, blurring the lines between boss and employee. Will Emily succumb to Mr. Johnson's charms or maintaโ€ฆ

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  • It's a hot Tuesday afternoon in August, and Emily, a shy and introverted office worker, has been summoned to the CEO's office for a 'personal meeting'. She's been working for the company for only three months, and she's heard rumors about the CEO's, well, let's say 'hands-on' management style. As she knocks on the door, she can feel her heart racing with anticipation and a hint of fear. Suddenly, the door opens, and there he is - the powerful CEO, Mr. Johnson, standing tall with an air of confidence and authority.
  • Emily's eyes are fixed on the floor as she enters the office, trying to avoid Mr. Johnson's piercing gaze. But she can't help but notice the way he towers over her, his broad shoulders and chiseled features making her feel like a tiny, insignificant speck. He gestures for her to take a seat, his deep voice commanding her attention as he begins to discuss her 'performance' in the company.
  • As the conversation progresses, Emily finds herself becoming more and more flustered, her face burning with embarrassment as Mr. Johnson's words cut deep into her confidence. But then, something unexpected happens. He reaches out and gently brushes a strand of hair behind her ear, his touch sending shivers down her spine. It's a small, intimate gesture, but it's enough to make Emily's heart skip a beat.
  • From that moment on, the 'meeting' takes a dramatic turn. Mr. Johnson's demeanor changes, his voice taking on a more sensual tone as he begins to 'mentor' Emily in ways she never could have imagined. The boundaries between boss and employee begin to blur, and Emily finds herself torn between her desire for Mr. Johnson's approval and her own inhibitions.
  • As the encounter reaches its climax, Emily realizes that she's never been so turned on in her life. She's not sure what's more thrilling - the rush of adrenaline or the thrill of being dominated by the powerful CEO. One thing's for sure, though - she'll never look at Mr. Johnson the same way again.

Preparation steps:

  • To set the scene, transform your living room or bedroom into a sleek, modern office. Invest in a large, wooden desk and a comfortable, leather-bound chair for the CEO. Add some plants, a few pieces of abstract art, and a luxurious area rug to complete the look.
  • Dress the part! The CEO should wear a tailored suit, complete with a crisp, white shirt and a tie. Emily, on the other hand, should dress in modest, office attire - a blouse, a pencil skirt, and a pair of heels. Don't forget to add some sexy, polished makeup and a few strands of pearls to complete the look.
  • To get into character, consider writing a backstory for your characters. What motivates the CEO? What are Emily's deepest fears and desires? The more you invest in your characters, the more believable and immersive the roleplay will be.

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Some tips:

  • To heighten the sense of anticipation, consider having the CEO send Emily a series of mysterious, flirtatious messages before the 'meeting'. This will help her get into character and build up the tension long before the roleplay begins.
  • Remember to communicate with your partner throughout the roleplay. Make sure you're both comfortable with the level of intimacy and the direction of the scenario.
  • Don't be afraid to improvise! The CEO's 'mentorship' can take many forms - perhaps he'll 'accidentally' brush against Emily's shoulder or 'instruct' her on how to properly take notes. The key is to stay in character and respond naturally to the situation.

Dialogue ideas:

  • You're so shy and introverted, but I bet there's a wildcat hiding beneath that surface. I want to bring her out and make her purr.
  • Don't be afraid of me, Emily. I just want to help you reach your full potential. But if you want my help, you'll have to be willing to follow my instructions... no matter what they may be.
  • You know, I've been watching you from afar, Emily. And I must say, I'm impressed. You have a certain... je ne sais quoi that I find very appealing.
  • 'You know, Emily, I think you have a lot of potential. But potential means nothing if you don't know how to unleash it. And I think I can help you with that.'
  • You're trembling, and I can see the fear in your eyes. But I want you to know that I'm not going to hurt you. At least, not too much.

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