The one thing about cross dressing is that it’s unpredictable. Maybe he’s lying to you and/or himself or maybe he has no idea where it’s going himself. A good gender therapist could help him figure it out. At one end of the spectrum is the person that’s happy just being able to wear panties and at the other is the person that won’t be happy until full transition complete with bottom surgery and hormones. In my case I wasn’t truly happy until everything in my wardrobe consisted of women’s clothing. That happened at age 50 which was 22 years ago. Before that there were periods of dressing followed by periods of not dressing etc.
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