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What got you interested in crossdressing ?

My experience is rather different . I started dressing up at the request by my then fiancé . She knew I was bi and wanted to see if she could get me to dress as a woman . Without thinking about it , I agreed . I told her that if I do it I will want my own clothes . Within 2 weeks she ha bought me 3 dresses , bras , panties , shoes , a wig and breast forms . After struggling to get dressed , I really liked how the clothes felt on me and how I looked . That was 25 years ago and I still do it to this day .
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Uniformed · 46-50, M
My experience was similar ..years ago a girlfriend got me to try on one of her big skirts as a laugh and I enjoyed it.. one day I surprised by wearing it with little white socks, and a pair of cute looking women keds copies I bought with a grey t-shirt saying "womens prison inmate".(I like the dressing up as punishment fantasy)We both thought it was funny and a turn on. I' m straight big and clumsy and not a a "sissy" by any means but still think it's fun and I think lots feel the same..