Compliment her fashion sense: Show genuine appreciation for her style and fashion choices. Compliment her outfits, accessories, and overall appearance. This will help create a positive rapport and show her that you value her opinion.
Express curiosity about her wardrobe: Ask her about her collection of clothes and express interest in trying out different outfits. You can say something like, "I've always admired your wardrobe. Do you think I could borrow something sometime? I'd love to see how certain styles would look on me."
Seek her advice and guidance: Approach her as a fashion mentor and ask for her suggestions on clothing, colors, or styles that would suit you. This can make her feel valued and involved in your transformation process.
Offer to assist her with her own dressing and styling: Volunteer to help her with selecting outfits, doing makeup, or styling her hair. By showing your willingness to contribute to her personal grooming, she may be more open to reciprocating the favor and assisting you in return.
Initiate a makeover session: Suggest a fun makeover session where both of you can experiment with different looks. Frame it as a playful activity rather than explicitly expressing your desire to crossdress. You can say something like, "I've always wanted to have a makeover session with someone. How about we try it out and see how creative we can get?"
Share your curiosity about trying new things: Talk about your desire to step out of your comfort zone and explore new experiences. Mention that you've always been curious about how it feels to dress up differently and ask for her support and guidance in trying it out.
Show appreciation and gratitude: Whenever she helps you with dressing up or makeup, express your genuine gratitude and joy. Let her know how much you appreciate her assistance and how happy it makes you feel. This positive reinforcement can encourage her to continue supporting you in the future.
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