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Welcome to Sissy Assignments .com, your ultimate destination for all kind of SissyAssignments 🎀✨

Your ultimate destination for 100s of guided free and premium adult assignments designed for sissies and crossdressers. Embrace your journey with personalized tasks, challenges, and transformative experiences!

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Free Sissy Milestones Checklist

Free Sissy Milestones Checklist for you

Checkout this free Sissy milestone checklist tool which will give you scores based on what you've done in your sissy journey. It includes options to choose on:

Panties, Bras, Hosiery, Lingerie, Shoes, Body Accessories, Cosmetics, Toys, Lifestyle, Outfits, Training, Masturbation, Sex, Mental, Cyber, Public, Social, and Permanent.

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Sissy Milestones

Sissy Journey Test

Test yourself to evaluate your sissy journey

Our Sissy Test contains 99 questions that will assess your journey through the following areas:

  • Sissy Clothing and Appearance
  • Feminization and Transformation
  • Sexual Behavior and Humiliation
  • Discipline and Control
  • Sexual Services and Control
  • Chastity and Orgasm Control
  • Lifestyle and Household Roles

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Sissy Test

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