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Dressing Up date idea illustration

Dressing Up

Duration: 2 hours
Budget: any

Catch your boyfriend in the act and take control! Discover his secret and make him dress up for you in this exciting roleplay scenario. Explore the limits of your relationship and have fun!

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  • It's a lazy Saturday morning in May, and you're lounging around the house, not doing much of anything. You decide to do some laundry, and as you're switching the clothes from the washer to the dryer, you stumble upon something that makes your heart skip a beat. You find a skirt, a blouse, and a pair of stockings hidden deep in the closet. You can't believe your eyes - what is this, and why is it in your boyfriend's closet?
  • You can't help but feel a mix of emotions - shock, confusion, but also a hint of excitement. You try to process what you're seeing, and your mind starts racing with questions. What is he doing with these clothes? Has he been dressing up behind your back?
  • You decide to investigate further and sneak into the room where your boyfriend is still asleep. You quietly approach him, and that's when you see it - he's wearing a lace bra and panties underneath his shirt. Your eyes widen in shock, and you can't help but stare. What do you do next?
  • You gently wake him up, and as he opens his eyes, you see a mix of fear and embarrassment on his face. You demand an explanation, and he stammers, trying to come up with an excuse. But you're not buying it. You're in charge now, and you're going to make him own up to his little secret.
  • You start to tease him, playing with his hair, and calling him 'pretty girl.' You can see the blush rising to his cheeks, and you know you have the upper hand. You're going to take full advantage of this situation, and make him dress up for you, just to see how far you can push him.

Preparation steps:

  • Set the scene by making sure the laundry room and bedroom are tidy and organized. You don't want any distractions from the main event.
  • Make sure to have some feminine clothes on hand, such as a skirt, blouse, and stockings. You can also add some makeup, wigs, or heels to really get into character.
  • Create a playlist with some sensual and playful music to set the mood. Dim the lights, and light some candles to make the atmosphere more intimate.

You may need

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Some tips:

  • Don't be afraid to get creative with the roleplay. The more you can get into character, the more immersive the experience will be.
  • Remember to communicate with your partner throughout the roleplay. Make sure you're both comfortable with what's happening, and that you're not pushing boundaries that shouldn't be crossed.
  • Take your time, and don't rush the experience. The more you can draw it out, the more anticipation and excitement you'll build.

Dialogue ideas:

  • You're going to dress up for me, and you're going to do it with a smile on your face. Understand?
  • You're my little girl now, and you're going to do what mommy says. Put on the skirt and blouse, and let's see how you look.
  • You look so cute in that lingerie, I almost don't want to take it off you. Almost.
  • Oh, pretty girl, you've been hiding secrets from me, haven't you?
  • I never knew you had such a feminine side, but I have to say, I'm loving it.

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