Crossdressing Friend

[AlwaysConfused]

I received a message from a friend saying 'I have a new hobby but can't say on here what'. I was a little worried that it would be something dangerous or illegal that I would have to talk him out of, so I phoned him straight away.

He explained that he tried on a few dresses at the weekend when he'd had a few drinks and that they made him feel really sexy. Since Saturday, he has purchased mini skirts, stockings, tight fitting tops etc but not worn the new clothes yet. He told me that it was something that he had never thought of before, it was impulsiveness to try on a dress, and felt a bit weird about it.

I was more than a little shocked - gobsmacked more like. I reassured him there was nothing weird about his new 'hobby', but to avoid stilettos as most woman cannot walk in them even after years of practice! He wants my help next week to find some nice clothes for him. I'm not uncomfortable with anyone wanting to crossdress, I've known people in the past that do. I was just VERY surprised it happens to be my bestest friend who I though I knew inside out.

He's 56, so it's hardly a teenage phase. He has recently lost his wife, dad and his 12 year old pet. Is he just looking for a little escapism? Should I help him to find fitting clothes, or just let him get on and do his own thing?

[cupid04]

Wharton goes commando in a kilt.

[bednobs]

i have a friend who is living "as a woman" at the moment, He's had no bit chopped off, and is engaged to a woman whi is heterosexual, he's just changed his name to a girl's name, and personal pronouns to "she" rather than he, plus also make up, wigs and dresses.
I have found it very hard to accept that my friend is in fact now a woman to all intents and purposes, and find it hard to know what to talk to him about. I want to ask him loads of questions but feel a bit reticent about that. My husband (whose friend he actually was first) refuses to even try and accept it.

[Wharton]

Guess what I've got in my sporran, cupid pal :-)

[jim360]

May not be a teenage phase, but could still be a phase. Especially so soon after such a tragedy. Be cautious but not condemning, and I'd suggest asking him to look for medical support at some point. If he does want your help, well at least talk to him about it all first rather than just going out and buying the dresses.

[andy-hughes]

Bednobs - I'd try a few general questions to make sure your friend is comfortanle discussing the subject, and see how things go.

I always see genuine interest as a sign of support, ahd hopefully he will as well.

It's a shame your husband is taking a blinkered approach - sometimes we are frightened by such changes in people we thought we knew. It's not a fear i suffer from, but its a shame if it splits their friendship at a time when your friend will be looking for all the support he can get.

[Baldric]

Every time I see this thread in Latest Posts I keep getting this image of Walliams and Lucas in my head!

[jomifl]

If he needs help then help him. He obviously misses his wife, can you not fix up a bit of female company for him?

[magsmay]

Squad -although AC's friend may be suffering from an inappropriate state of depression precipitated by the deaths of his wife father and pet (as opposed from normal grief) he may also just be manifesting behaviour he has been suppressing for years. Without consulting with the 'patient' and coming to any definite conclusions it is unwise to advise AC to 'keep out of it'. The friend is not yet (if ever) in the process of psychiatric assessments or treatments, so I advised AC to be supportive of her friend while perhaps persuading him to seek counselling ,which invariably could eventually lead to other psychological help if this is deemed appropriate.

[Sqad]

magsmay..OK...wrist slapped ;-)

[Old_Geezer]

If he tells you it is something new and not something he's considered before then I'd say yes, it is probably an escape from this normal life to something different. If, on the other hand, it is something he's suppressed throughout life, then that is probably a different issue. But ultimately it's not really important what it is.

If you don't mind helping then why not ? It's a harmless quirk. Although I suspect the public at large may not all be so open minded. I think I'd advise him to keep it to his home unless he is prepared to accept ridicule.