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Sissy Surprise

Duration: 2 hours
Budget: any

As you discover your boyfriend trying on your lace panties, you decide to take control and turn him into your sissy. You give him a makeover, dress him up in your clothes, and apply makeup to his face. As the night progresses, you introduce him to various toys and roleplay scenarios, exploring his โ€ฆ

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  • As you enter your bedroom, you find your boyfriend trying on your favorite lace panties. You can't help but feel aroused by the sight of him in your underwear.
  • You decide to take control of the situation and turn him into your sissy. You start by giving him a makeover, dressing him up in your clothes and applying makeup to his face.
  • As the night progresses, you introduce him to various toys and roleplay scenarios, pushing his boundaries and exploring his newfound femininity. By the end of the night, you've created a sissy that's all yours.

Preparation steps:

  • Purchase a variety of lingerie, including panties, bras, and stockings, in your boyfriend's size.
  • Gather makeup, including foundation, blush, eyeshadow, lipstick, and mascara, to create a feminine look for your boyfriend.
  • Prepare a selection of toys, such as dildos, vibrators, and anal plugs, to introduce your boyfriend to new sensations and experiences.

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Some tips:

  • Encourage your boyfriend to fully embrace his new role as a sissy by using feminine pronouns and addressing him as 'her' or 'she'.
  • Create a safe and consensual environment by discussing boundaries and limits before beginning the roleplay.
  • Incorporate roleplay scenarios that allow your boyfriend to explore his feminine side, such as dressing up as a French maid or a naughty schoolgirl.

Dialogue ideas:

  • Oh, you look so cute in my panties! I think it's time to give you a makeover, my little sissy.
  • You're all mine now, sissy. I'm going to show you a whole new world of pleasure.
  • How does it feel to be a sissy, baby? I'm going to make you feel so good tonight.
  • Let's try some makeup, darling. I want to make you look even more beautiful.
  • Mmm, I love how you look in my clothes. You're such a pretty sissy for me.

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