My mom loved to dress me up and play with my long hair putting it in a French braid or pigtails. My girlfriends and wife did as well and now my daughters like to dress me up. It helped a lot having naturally feminine looks. But the girls in my family are definitely in the minority. If you have long hair and most cross dressers should, a lot of girls who will date a guy with long hair and compliments the guy on his long hair it should not be too difficult to convince them to participate in cross dressing you. In fact it has been my experience that if you look fem and have long pretty hair girls will approach you on the topic.
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