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Serving the Boss date idea illustration

Serving the Boss

Duration: 2 hours

Play the role of a waitress flirting with a wealthy businessman in a high-end restaurant. As you take his order, the tension builds and you can't help but wonder what would happen if you gave in to your desires.

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  • It's a busy Saturday in June, and you're working as a waitress at a high-end restaurant. Your boss, a wealthy and powerful businessman, has been coming in every week for the past month, always sitting in your section. You've developed a flirtatious rapport with him, and you can't help but notice the way he looks at you, like he owns you. Today, he's sitting alone at his usual table, sipping on a glass of scotch. You take his order, trying to play it cool, but you can't help but feel a spark of excitement as your hands touch when you hand him his menu.
  • As you're taking his order, he makes a comment about how you look particularly stunning today, and you can't help but blush. You try to brush it off, but you can tell he's not just being polite. He's got a hungry look in his eye, and you know exactly what he's craving. You take his order and head back to the kitchen, your heart racing with anticipation.
  • When you return with his food, he beckons you over, his eyes locked on yours. You lean in close, feeling his hot breath on your ear as he whispers something naughty in your ear. You try to play it cool, but you can't help but giggle, and he takes that as a sign to take things to the next level.
  • He reaches out and gently strokes your arm, sending shivers down your spine. You look around the restaurant, making sure no one is watching, before you lean in closer, your lips almost touching his ear. You whisper something back, and he smiles, his eyes glinting with desire.
  • As the night wears on, the tension between you builds. You can't help but wonder what would happen if you gave in to your desires, if you let him take you back to his office and show you who's really in charge.

Preparation steps:

  • To set the scene, find a private room or office that can be transformed into a luxurious setting. Add some candles, dim lighting, and a comfortable couch or chair to create an intimate atmosphere. You can also add some props like a desk, chair, and some files or papers to make it look like a real office.
  • Dress up in a sexy waitress outfit, complete with a short skirt, high heels, and a tight blouse. Make sure to add some provocative makeup and hairstyle to complete the look. Your partner can dress up in a suit and tie, looking like a powerful businessman.
  • To get into character, take some time to talk about your roles and what you want to get out of the scenario. Discuss boundaries and what you're comfortable with, and make sure to establish a safe word in case things get too intense.

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Some tips:

  • To make the scenario more realistic, try to stay in character as much as possible. Use your body language and tone of voice to convey the desired emotions and intentions. Remember to breathe, relax, and have fun with it!
  • Don't be afraid to get creative and improvise. The scenario is just a starting point, and you can take it in any direction you want. Use your imagination to come up with new and exciting ways to tease and tantalize each other.
  • Communication is key in any roleplay scenario. Make sure to communicate with your partner throughout the scenario, checking in to make sure everyone is comfortable and having fun. This will help you build trust and intimacy, and create a more intense and satisfying experience.

Dialogue ideas:

  • Your service is always top-notch, but I think I'd like a little extra attention tonight.
  • You look stunning today, darling. I think you'd look even better out of that uniform.
  • Let's get one thing straight, sweetheart. I'm not just buying dinner, I'm buying you.
  • You're so close, I can smell the perfume on your skin. It's intoxicating.
  • You know, I think I've had enough of this meal. But I haven't had nearly enough of you. Come closer.

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