The Boss and the Secretary date idea illustration

The Boss and the Secretary

Duration: 2-3 hours
Budget: $100-$200

Experience the alluring task of flirting at workplace with your partner as the powerful Boss and the seductive Secretary. The complexity of maintaining professional demeanor and the clandestine flirtings would create a memorable evening.

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  • You and your partner take on the roles of the influential Boss and the charming Secretary respectively. As the boss, you have an important meeting to prepare. You need papers, files, and your secretary to get everything ready. However, you can't help but be distracted by her. You come up with ways to keep her close by, not letting her leave the room until she’s completed her tasks.
  • She plays along, always trying to color outside the job-description. She raises questions, doubts, requests only to gain your attention, even as she completes her assigned duties.
  • Imagine a late working evening, when all the other employees have left and it's only the two of you in the dimmed office light. There’s attraction that builds with every lingering gaze and touch. Respect the boundaries yet flirt without crossing the line. Embark on this thrilling and forbidden journey

Preparation steps:

  • The important aspect of this roleplay is the atmosphere and costumes. Start by setting your own house like an office. Arrange a desk, stationeries, laptop etc. Make sure the room has dimmable lights. For the costumes, the Boss could wear a formal suit and the Secretary could slip into a pencil skirt with a blouse or a body-con dress with stilettos.
  • Work out some key dialogues beforehand which would be used during the roleplay, moreover it is very important to set boundaries, as this role-play tends to go out of hand sometimes.
  • The scene begins with the leaving of last employee. Leave a time gap between each dialogue and movement, this would create sensuous tension and make it more appealing.

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Some tips:

  • Discuss and respect one another's comfort levels before middle and even during the roleplay, this would make both of you comfortable and enjoy the scenario better.
  • Remember that this is just a roleplay. Keep in mind not to relate this role-play outside of this scenario, as it may affect in real life professional environment.
  • If this is your first time roleplaying, don't worry about saying or doing the 'right' thing. This scenario is all about having fun and exploring new aspects of your relationship together. Relax and enjoy!

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