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Boss's Private Assistant date idea illustration

Boss's Private Assistant

Duration: 1 hour

Indulge in a steamy roleplay as a powerful boss and your seductive secretary. In this scenario, you hire a personal assistant who captivates you with their confidence and sultry demeanor. As they take charge of your schedule and tasks, their flirtatious behavior ignites a thrilling office romance. โ€ฆ

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  • You, a successful and powerful businessman, have been feeling the pressure of your demanding job. As a remedy, you decide to hire a personal assistant, someone who can ease your workload and cater to your every need. Enter your partner, a confident and seductive secretary. They stride into your office, dressed to impress, with a tight pencil skirt and a blouse that hints at their curves. Their hair is neatly tied, and they carry a notepad and pen, ready to take your commands.
  • You, the boss, sit back in your leather chair, taking in the sight of your new assistant. You introduce yourself, but before you can say more, they confidently take charge. "Mr. [Your Last Name], I'm here to ensure your every need is met." Their voice is smooth and sultry, sending a shiver down your spine. You can't help but feel a surge of excitement as you realize this assistant is more than just a professional asset.
  • The secretary begins by asking about your day, taking notes on your schedule and tasks. As they lean over your desk, you catch a glimpse of their cleavage, a deliberate tease. You clear your throat, trying to maintain a professional demeanor, but your mind is already wandering to more intimate thoughts. "I'll make sure your calendar is organized, and I'll handle any tasks you need assistance with," they assure you, their eyes holding a mischievous glint.
  • As the day progresses, the secretary's tasks become more personal. They bring you coffee, taking care to brush their hand against yours. They whisper suggestions for your upcoming business trip, their breath tickling your ear. You find yourself eagerly anticipating their every move, craving their attention and the promise of something more.
  • Finally, as the workday comes to a close, you decide it's time to take charge. You stand up, towering over your assistant, and whisper, "Stay after hours, I have a special assignment for you." The secretary's eyes light up with excitement, and they nod in agreement. You close the office door, ensuring privacy, and begin to reveal your true desires...

Preparation steps:

  • To set the scene, create a makeshift office space. This can be in a home office or even a corner of a bedroom. Set up a desk, a comfortable chair for the boss, and a smaller chair or stool for the secretary. Ensure the desk has a phone, a notepad, and a pen, as these props will be essential for the roleplay.
  • Costumes are key to this scenario. As the boss, consider wearing a well-fitted suit, perhaps with a tie that can be loosened as the roleplay heats up. The secretary should dress to impress, with a business-like outfit that hints at their sensual side. A tight pencil skirt, a low-cut blouse, and a pair of glasses can all contribute to the fantasy.
  • Set the mood with lighting and music. Dim the lights to create an intimate atmosphere, and consider playing soft, sensual music in the background. A jazz or blues playlist can set the perfect tone for this steamy office encounter.
  • Prepare a list of tasks and scenarios for the secretary to handle. This can include taking notes, organizing your (fake) schedule, bringing you coffee, and even roleplaying a business trip with some naughty twists. The more interactive and engaging the tasks, the better!
  • Don't forget the props! A briefcase, a laptop, and even a bottle of wine (for a 'business dinner') can all add to the realism and fun of the roleplay. Be creative and think of items that will enhance the experience and allow you both to fully immerse yourselves in the roles.

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Some tips:

  • Communication is key! Discuss boundaries and desires before starting the roleplay. This will ensure both partners are comfortable and excited to explore this fantasy.
  • As the boss, remember to be assertive and commanding. Take charge of the situation, but also allow your secretary to tease and tempt you. It's a delicate balance of power and desire.
  • The secretary should embrace their role as a confident and seductive assistant. Use body language, eye contact, and subtle touches to convey desire. Tease your boss, but also be attentive to their needs and commands.
  • Consider incorporating elements of BDSM if both partners are comfortable. The boss can give the secretary 'punishments' for 'mistakes' or introduce rewards for a job well done. This can add an extra layer of kink to the roleplay.
  • Remember, the goal is to have fun and explore each other's fantasies. Don't be afraid to get creative, add your own twists, and make this roleplay truly memorable. Enjoy the power dynamics and the steamy office affair you've created!

Dialogue ideas:

  • Secretary: (Teasingly) Oh, I'm all ears, sir. What kind of... relaxation do you have in mind?
  • Boss: I want you to take charge, show me what a naughty secretary you can be. I'll be your obedient boss for the night.
  • Boss: You know, I think we should discuss some... private matters. After all, you're not just my assistant, you're my... personal confidant.
  • Secretary: Oh, I'd love to assist you with anything you desire, Mr. [Last Name]. I can be very... thorough in my duties.
  • Boss: I've been thinking, perhaps we could... unwind after a long day. A private meeting, just you and me.

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