A
female
age
41-50,
anonymous
writes:My boyfriend recently confided in me that he has tried dressing in women's clothes. I admit that I had already guessed when I found oversized women's shoes in his cupboard, along with makeup and a few items of clothing. I told myself they belonged to his last girlfriend, who had larger feet than me. Anyway, now he has told me, he is keen to increase his wardrobe of female clothing and wants me to help him use makeup. I am a very open-minded person but it does still make me a little uncomfortable thinking he might do this a lot now I know. I think it is harmless from time-to-time, and a bit of excitement in our sex life, but am concerned it may become a bigger part of his life. My boyfriend is very masculine and enjoys the gym and cycling amongst other hobbies. I know he isn't gay and we have a very healthy sex life, even watching heterosexual porn together and trying out other fantasies and this really is no different. I am just not sure how I talk to him about why he does it and how long he has been doing it etc. without making him feel ashamed. Any advice?
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female
reader, anonymous, writes (13 November 2011): Thanks ironman. We did talk about it over the last few days and that is exactly how he feels. He said as a man he never gets to feel sexy and while dressing up in a suit makes him feel good, wearing women's clothes makes him feel sexy. I guess I just freaked out a bit because he pulled out a wig and makeup, and I suppose I thought just wearing the clothes would be enough. He doesn't want to be a woman or go out dressed up and it stems from nasty comments made about him at school, about not being attractive to women. It made me cry when he told me. I love him so much and want him to be happy.
I guess you are right about the novelty wearing off. He said he hasn't done it for over a year (since we have been together) because he hasn't needed to and because he was scared to tell me. He also said he doesn't need it as I turn him on so much. Despite my open frame of mind, I think it still was a bit of the unknown for me that freaked me out. I just want him to be happy. The thought of him dressing up and having sex with me disturbs me only because I am not gay and don't want to take part in that kind of role play.
Thanks again.
A
male
reader, ironman777  +, writes (11 November 2011):
ok... to be fair I was like your boyfriend - I enjoyed cross dressing and wearing high heels and things. I do it because its sexy and forbidden and to a certain extent makes me feel feminine - I guess I have a large feminine side. I dont like guys, never would have sex with one and know I would make a very ugly girl if I switched sex so no point. And I can enjoy some aspects of being a woman whilst being a man.I guess just assume its role play and he will get super horny about it. And if you do it with him, after a while the specialness of it would possibly reduce and he will do it less. But be prepared for him to try it out a lot at first. He hopefully likes being a man and will love you all the more for being caring towards him. I bet he is a good listener for you as well.Geez - I've never told anyone this before!!
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