Dear Annie: After wife retires, longtime crossdresser feels he’s lost the space to be himself
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By Annie Lane
Published on April 18, 2026.
Longtime crossdresser, who has been married and a longtime cross-dresser for 26 years, feels he has lost the freedom to be himself after his wife retired and has little time left to express himself. His wife, who supports his hobby, is not keen on participating in the hobby but is OK with him dressing as a woman when she's not around. This arrangement worked until her retirement, but now she has limited time to express herself. The author suggests an honest conversation with her wife about making room for him to still be himself and compromise on agreed-upon time or space to dress, or still go out without straining the relationship. She also mentions that her husband, who is known for his openness and openness, overshares his personal information, especially his health information, which breaches trust.
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