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"Yes we chat quite often and get on well I do odd jobs for her sometimes but it might make things uncomfortable if I told her I fancy her! " Yeah it's always a possibility. Would you be thinking of a relationship or just a sex thing? | |||
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"I'd like it to be a friendship with the possibility of sex but not essential someone to dress with would be nice she wears lovely makeup but doesn't know I'm a cross dresser. " Maybe move the conversation on a little at a time. Compliment her a little, ask her if she'd like to share a bottle of wine one evening. You will be able to tell from her reaction if she wants to take things further. Bringing up your cross dressing might be more of a challenge. | |||
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"I'd like it to be a friendship with the possibility of sex but not essential someone to dress with would be nice she wears lovely makeup but doesn't know I'm a cross dresser. Maybe move the conversation on a little at a time. Compliment her a little, ask her if she'd like to share a bottle of wine one evening. You will be able to tell from her reaction if she wants to take things further. Bringing up your cross dressing might be more of a challenge. " . Yes I've thought along those lines maybe say something about trans issues and see how she reacts? | |||
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"I'd like it to be a friendship with the possibility of sex but not essential someone to dress with would be nice she wears lovely makeup but doesn't know I'm a cross dresser. Maybe move the conversation on a little at a time. Compliment her a little, ask her if she'd like to share a bottle of wine one evening. You will be able to tell from her reaction if she wants to take things further. Bringing up your cross dressing might be more of a challenge. . Yes I've thought along those lines maybe say something about trans issues and see how she reacts? " It's difficult to know. People are surprising in what they accept and don't. I know that if a guy started to talk to me in a general way about cross dressing I'd assume it was something he was interested in and ask him if he was. But not everyone's the same. | |||
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"I'd like it to be a friendship with the possibility of sex but not essential someone to dress with would be nice she wears lovely makeup but doesn't know I'm a cross dresser. Maybe move the conversation on a little at a time. Compliment her a little, ask her if she'd like to share a bottle of wine one evening. You will be able to tell from her reaction if she wants to take things further. Bringing up your cross dressing might be more of a challenge. " Definitely this. Give it a go. | |||
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