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Online chat buddy wants to cross-dress


New Member
Not sure how I get into these weird situations, but here goes...

I've started chatting regularly to a guy online. He's very nice but, on one occasion, we were talking about the PJs I sometimes wear when working from home. When he complained that he had no PJs I jokingly said he should buy some like mine. The next time I spoke to him he told me he had ordered some. Since then he has bought tights and heels, shaved his legs and tells me I have opened up a new side to him, which he is loving. He is talking about going out dressed as a female. When I advise him against this his response is 'Should I stop then?'. He seems to want to do whatever I say which leaves me in a quandary - I believe in LGBT equality and think it's great that he has found a feminine side but I also feel that if anything bad happens to him as the result of all this it would somehow be my fault. I'm not really sure what to do. Should I be tough with him and tell him to man up or encourage him to be himself? I have tried telling him to follow his heart but he just seems to look to be for advice all the time.

We're unlikely to ever meet as he lives the other end of the country, but he seems like a really nice guy so I want to make sure I handle this properly. For some reason guys seem to latch on to me in chatrooms - maybe I shouldn't be so nice :)

Opinions welcome please.



New Member
I don't think you should encourage him as you know being himself can also be dangerous for him. If being one's own self is disastrous, I mean he maybe living in a place where he may face consequences of doing this. He should be stopped from doing this. And you can't literally stop him, but you start pointing out things and making him realize that he doesn't look good in those dress and politely showing him your wish to see him in jeans whatever male dresses.

If he is, who he is, he will identify it later again. But for now, you shouldn't be the reason or to be blamed, so stop him.


New Member
Thank you. I think you're right. I suspect he would have done it regardless of my being there but I think he's now going through some crisis of conscience and it looking to me for approval. It sounds hard but I don't want to be blamed for some major life change so I need to be a bit hard. Most of the guys I meet are cocky and self-assured so I sometimes forget how impressionable and vulnerable some of them can be.