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The Italian Boss and His Intern date idea illustration

The Italian Boss and His Intern

Duration: Full day
Budget: $500+

In a Tuscan villa, a powerful CEO orchestrates a fantasy day with his naive intern, blending business with pleasure under the Italian sun. A mix of elegance and seduction awaits in this roleplay scenario.

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  • It's a sunny Sunday in June, and you, the powerful CEO, have decided to spend the day at your luxurious villa in Tuscany, Italy. You've invited your new intern, a beautiful and naive young woman, to join you for a 'business meeting' in the beautiful Italian countryside.
  • As you arrive at the villa, you're greeted by the sound of birds chirping and the smell of freshly cut grass. You've set up a lavish outdoor seating area, complete with champagne and hors d'oeuvres, to impress your intern and get her in the right mindset for the day.
  • You've been eyeing your intern all week, and you can't wait to get your hands on her. You've planned a series of 'team-building' exercises to help her get to know you better, but really, you just want to get her naked and submissive.
  • As the day wears on, you'll take your intern on a romantic horseback ride through the rolling hills of Tuscany, making sure to 'accidentally' brush up against her body and whisper sweet nothings in her ear.
  • After the ride, you'll return to the villa for a decadent lunch, complete with oysters and champagne. You'll make sure to feed her by hand, stroking her lips and face with your fingers as you do.
  • As the afternoon sun beats down, you'll lure your intern into the villa's private pool, where you'll 'accidentally' strip off her swimsuit and leave her naked and vulnerable. And that's when the real fun begins.

Preparation steps:

  • To set the scene, rent a luxurious villa in Tuscany with a private pool and outdoor seating area. Make sure to stock up on champagne, oysters, and other decadent treats to impress your intern.
  • Buy a new swimsuit for your intern, something skimpy and revealing that will drive you wild. You can also pick up some toys and bondage gear to use later in the day.
  • Set up a romantic horseback ride through the rolling hills of Tuscany. You can hire a guide or go it alone, depending on your preference.

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Some tips:

  • To really get into character, dress the part of a powerful CEO, complete with a three-piece suit and tie. Your intern should dress in a revealing business outfit, complete with a short skirt and low-cut blouse.
  • Make sure to be dominant and assertive throughout the day, using your powerful CEO persona to intimidate and seduce your intern.
  • Don't be afraid to get a little rough and dirty, after all, that's what your partner is looking for. So, grab her by the hair, spank her ass, and make her beg for more.

Dialogue ideas:

  • 'Whoops, looks like your swimsuit top came undone. Let me help you with that... or not' (smirking at her nakedness)
  • 'You look stunning today, I must say. That dress was made for you, wasn't it?' (stroking her arm)
  • 'Lift your chin, my lovely. I want to feed you this oyster just right' (feeding her)
  • 'Let's get a little closer, shall we? The view from up here is breathtaking' (pulling her onto your lap)
  • 'Where do you want to ride first, my beautiful intern? The hills or the woods?' (whispering in her ear)

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