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The Blackmailed Boss date idea illustration

The Blackmailed Boss

Duration: until exhaustion
Budget: any

Get ready for a thrilling roleplay where a sneaky worker blackmails their hot boss into doing their bidding. From getting coffee to giving massages, the boss must obey every command. But as the night wears on, things take a sensual turn. Will the boss surrender completely?

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  • It's a typical Monday morning in May when you, the worker, stumble upon a compromising situation involving your hot boss. You've had a thing for your boss for a while now, but you never thought you'd have the upper hand. You've discovered a deep, dark secret that could ruin your boss's career and personal life. You've decided to use this information to your advantage, and you're going to make your boss do your bidding. You call your boss into your office, a sly smile spreading across your face as you reveal what you know. Your boss tries to deny it, but you've got the evidence right there in your hand. You make your demands, and your boss reluctantly agrees to do whatever it takes to keep their secret safe.
  • As the day goes on, you make your boss do all sorts of tasks, from getting you coffee to giving you a massage. Your boss is furious, but they know they have no choice. You're in control now, and you're going to milk it for all it's worth. You make your boss wear a tight, revealing outfit to a meeting, just to see how far you can push them. Your boss is seething, but they can't do anything about it. You're the one with the power now, and you're going to use it to get what you want.
  • As the day winds down, you decide to take things to the next level. You make your boss come to your place, where you have a few more tricks up your sleeve. You've set the mood with candles and soft music, and you're ready to take your boss to new heights. You start with a sensual massage, your hands roaming over your boss's heated body. Your boss is trying to struggle, but you're not having it. You're in control, and you're going to make your boss beg for more.
  • As the night wears on, things get more and more intense. You're pushing your boss's boundaries, making them do things they never thought they'd do. You're in charge, and you're loving every minute of it. Your boss is at your mercy, and you're going to make them surrender completely.
  • In the end, you're left exhausted but satisfied. You've never felt so powerful in your life, and you know that you'll never let go of this feeling. Your boss, on the other hand, is left feeling defeated and submissive. You've broken them, and you know that they'll do anything to please you.

Preparation steps:

  • Set the scene by decorating your living room with candles and soft music. Make sure you have a comfortable place for your boss to sit or lie down. You'll also need some sensual massage oil and a few toys to help things along.
  • Make sure you're both dressed appropriately for the roleplay. You, the worker, can wear something casual but comfortable, while your boss should wear something more revealing and tight. Think short skirts and low-cut tops.
  • To really get into character, try to pinpoint exactly what your boss's secret is. What did they do that's so bad? How are you going to use it against them? Get into the mindset of a blackmailer, and don't be afraid to get a little dirty.

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Some tips:

  • To really make this roleplay special, try to improvise as much as possible. Don't be afraid to try new things and push your boss's boundaries. Remember, you're in control, so make the most of it.
  • Make sure to communicate with your boss throughout the roleplay. Check in with them regularly to make sure they're comfortable and consenting. You want to make sure you're not pushing them too far.
  • Don't be afraid to get a little rough. This is a blackmail scenario, after all. You're supposed to be in charge, so don't be afraid to take what you want. Just remember to keep it safe and consensual.

Dialogue ideas:

  • You're going to wear that tight dress and high heels to the meeting, and you're going to make sure everyone knows you're mine.
  • Get on your knees and show me what a good girl you can be. Lick my boots, boss lady.
  • You're going to do exactly as I say, or else. And if you're good, I might just let you pleasure me.
  • Take off your blouse and let me see what I've been craving for so long. And don't even think about saying no.
  • You're so wet and ready for me, aren't you? Beg for it, and maybe, just maybe, I'll give it to you.

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