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Office Affair date idea illustration

Office Affair

Duration: 1-2 hours
Budget: $any

In this steamy office romance scenario, you play the boss who can't resist the charms of your new secretary. Will you succeed in making your move or will she keep things professional?

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  • It's a hot summer Tuesday in July, and you're the boss of a successful company. You've been eying your new secretary, who's been working for you for a few weeks now. You can't help but notice how her tight skirt hugs her curves, and how her blouse accentuates her cleavage.
  • You've been finding excuses to call her into your office, just so you can admire her from up close. Today, you've finally mustered up the courage to make your move. You call her into your office, under the pretense of discussing a new project.
  • As she walks in, you can't help but notice how her heels click on the floor, and how her hair falls in luscious waves down her back. You gesture for her to sit down, but you have no intention of keeping things professional.
  • You start to chat with her about the project, but your eyes are fixed on her lips, imagining what they would feel like wrapped around your cock. You know you're playing with fire, but you can't resist the temptation.
  • As the conversation progresses, you start to get more and more flirtatious, testing the waters to see how far you can push things. Will she take the bait, or will she stick to being professional?

Preparation steps:

  • To set the scene, decorate your room to look like a high-end office. Invest in a fancy desk, a comfortable chair, and some office supplies to complete the look.
  • Dress the part - you, the boss, can wear a sharp suit and tie, while your secretary can wear a tight skirt and blouse. Don't forget to add some heels and stockings to complete the look.
  • Make sure to have some props on hand, like files and papers, to add to the illusion. You can also set up a camera or phone to record the scene, to add an extra layer of excitement.

You may need

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Some tips:

  • To really get into character, research some common office scenarios and phrases to use during the roleplay. This will help you both get into the mindset of the characters.
  • Don't be afraid to get creative with the scenario - maybe your secretary is a little hesitant at first, or maybe she's been waiting for you to make a move all along.
  • Remember to communicate with your partner before and during the roleplay, to make sure you're both comfortable with what's happening. And most importantly, have fun with it!

Dialogue ideas:

  • I'm having a little trouble concentrating on the project, can you help me refocus? Maybe we can brainstorm together, really closely
  • I must say, you're looking particularly stunning today, Miss. That skirt is really bringing out the best in you
  • Don't get me wrong, this project is important, but I think we could both benefit from a little... stress relief. Maybe I can show you my stress relief techniques over lunch?
  • I love the way you take notes, your hand is so... dexterous. I bet you're skilled at many things
  • You know, I think I need a little more... hands-on assistance with this project. Would you be willing to stay late and help me out?

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