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The Boss's Sunday Fling date idea illustration

The Boss's Sunday Fling

Duration: unlimited

Play out a steamy roleplay scenario as the powerful boss and your secretary, where you'll use your authority to get a rise out of her. Dictate a letter to her, slipping in suggestive phrases, and see how far you can push her.

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  • It's a lazy Sunday morning in May, and you're playing the role of the powerful boss, sitting behind your large mahogany desk in your office. Your secretary, played by your partner, enters the room, looking ravishing in a tight pencil skirt and blouse. You can't help but notice the way her legs look in those heels, and the way her hair is styled perfectly for the day.
  • As she approaches your desk, you can't help but feel a sense of authority and control, knowing that you're the one calling the shots. You begin to dictate a letter to her, your voice firm and commanding, as you gaze into her eyes, trying to get a rise out of her.
  • As she takes notes, her eyes locked on yours, you can't help but think about how much you want to bend her over that desk and take her right there. You start to get creative with your dictation, slipping in a few suggestive phrases, just to see how she reacts.
  • She begins to blush, her cheeks flushing pink as she tries to maintain her composure. You can see the desire in her eyes, and you know you've got her right where you want her.
  • It's time to take things to the next level, and you lean forward, your eyes locked on hers, as you whisper a few choice words in her ear...

Preparation steps:

  • Set the scene by creating a makeshift office in your home. Clear off a desk and chair, and add some office decorations like a clock, a pen holder, and a few files.
  • Dress the part - the boss can wear a suit and tie, while the secretary can wear a tight, professional outfit with heels.
  • To add to the authenticity, consider investing in a few props like a dictation machine, a notebook, and a pen. You can also play some soft background music to set the mood.

You may need

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Some tips:

  • To really get into the roles, try to stay in character as much as possible. The boss can try to assert their dominance, while the secretary can try to tease and tempt.
  • Don't be afraid to get creative with the scenario - the boss can try new ways to assert their control, while the secretary can try new ways to resist and tease.
  • Remember to communicate with your partner throughout the scenario, making sure everyone is comfortable and enjoying themselves.

Dialogue ideas:

  • You're doing a wonderful job taking notes, but I think you'd do an even better job on your knees, don't you?
  • You know, I think I need you to come around the desk and show me exactly how you're taking these notes. Up close and personal.
  • I'm not sure what's more impressive, your typing skills or the way your ass looks in that skirt. Maybe we can discuss it further over lunch... in my office... with the door locked.
  • I hope you're not planning on leaving early today, because I have a few... tasks in mind that require your undivided attention.
  • As I dictate this letter, I want you to imagine me sliding my hand up your thigh, feeling your warm skin beneath my fingers.

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