Getting my husban to Crossdress

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Ms. Sami: I would like to get my husband to crossdress. He made a fine figure of a woman when he was out from medication and some girlfriends of mine and myself made him up. He would be considered full figured and we put a 44 DDD bra on him red with matching red panties. We then put red nylons with matching garter on him. He always loved redheads so we put a red wig on him. We then proceeded to make up his face and while we were doing this he seemed to get hard. Then (with some difficulty) we managed to put a red dress on him. Then we took pictures and had some great laughs. Then we undressed him, however, I was almost caught the next day when he awoke with the panties, nylons and garter on him. I just stated to him that he must have dressed himself before going to be and went in the wrong drawer. He was so out of it he believed me. When I mention how good he would look dressed like a woman he changes the subject. He does like me doing him with a strapon and I feel like it would be great to change places while doing it. Jane Dear Jane, First, do you have any sisters? Sorry, I couldn’t help myself... Crossdressing is a very personal thing. Most men have no interest in it and would never ever show any interest. It is un-manly. It takes a very brave man to admit that he would even like to try. It really is risky business. If it ever got out, it could easily end your marriage and he could loose his job. This is serious. However, if he did admit that he had an interest, it would show massive trust in you. As to encouraging your husband to Crossdress, if there is no interest, there is no interest. So how do you judge the interest and get past the masculine un-manly shields? I would suggest you rent a movie with a crossdressing character like TOOTSIE (1983) with Dustin Hoffman as Dorothy Michaels. See what his reaction is to the issue. Tell him you found this web site and that you think it would be fun to dress together. And if you think the time is right, tell him you want to do it while you are both dressed up or where you both Crossdress. This could be a secret you share. But you could most likely not share it with your girl friends. If there is any chance of it getting out, he may just never admit anything even if it is interested. Please write again and I will do all I can to help further. Hugs, Sami