Quizzes & Puzzles1 min ago
Crossdressing Friend
50 Answers
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?
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?
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No best answer has yet been selected by AlwaysConfused. Once a best answer has been selected, it will be shown here.
For more on marking an answer as the "Best Answer", please visit our FAQ.I'd say he needs counselling, but probably needs some extra help. His wife was his carer up until she died, and has been too proud to ask for help since then (my friends and I do what we can around work and commitments). He has been running around after his mum for the past two months since his dad died, doing pretty much everything and also stressing about care for his sister as his mum can no longer cope.
I'm concerned that he has gone for mini skirts and stocking. How tarty! I'll have to teach him a little class :D
I'm concerned that he has gone for mini skirts and stocking. How tarty! I'll have to teach him a little class :D
tonyav - "AlwaysConfused, Has he show'n his errrrr effeminate signs in the past ?, you know, like putting the toilet seat back down after he's been for a wee wee."
Most men who cross-dress are not in the least effeminate - you are confusing the words effeminate and feminine - which rather underlines your ignorance - compounded by your 'humourous' asides.
If you feel insecure, don't worry, we're all here to help.
Most men who cross-dress are not in the least effeminate - you are confusing the words effeminate and feminine - which rather underlines your ignorance - compounded by your 'humourous' asides.
If you feel insecure, don't worry, we're all here to help.
Hiya always confused you darling friend you, i just had to sign up as i read this story with a tear in my eye at what your friend went through which isn't to dissimilar to my story which i can't really get into as i'm in a rush but will give you the basics.
I always knew i was gay but came from a very strict catholic family and my father was often drunk and violent so coming out was always a nono. When i was about 18 the mixture of hormones and the feeling of entrapment got to much and i decided to end my life which would've been pretty much the end if i hadn't met a friend who taught me that it was okay to be me and i should set myself free and gave me the guts to stand up to my father who psychologically was all my fears rolled up into one angry person. Her friendship and her giving me support is the only reason i'm still here and everything i've ever achieved is down to her, unfortunately she passed away a few years ago but i had a dream come true when i was on stage singing a duet with a famous country singer and gave an impromptu eulogy in her honor in which she and i were given a standing ovation.
^Sorry i just had a quick cry whilst trying not to destroy my mascara, anyway this could be a phase your friend's going through or it could be something else but please just promise me you'll always be there for him and support him whichever choices he makes and he'll be eternally grateful no doubt about that.
Anyway i'd love to stay and chat more but we have some promoting to do and god knows how long i'll last under this wig in the sun.
Byeee, mwa, mwa.
I always knew i was gay but came from a very strict catholic family and my father was often drunk and violent so coming out was always a nono. When i was about 18 the mixture of hormones and the feeling of entrapment got to much and i decided to end my life which would've been pretty much the end if i hadn't met a friend who taught me that it was okay to be me and i should set myself free and gave me the guts to stand up to my father who psychologically was all my fears rolled up into one angry person. Her friendship and her giving me support is the only reason i'm still here and everything i've ever achieved is down to her, unfortunately she passed away a few years ago but i had a dream come true when i was on stage singing a duet with a famous country singer and gave an impromptu eulogy in her honor in which she and i were given a standing ovation.
^Sorry i just had a quick cry whilst trying not to destroy my mascara, anyway this could be a phase your friend's going through or it could be something else but please just promise me you'll always be there for him and support him whichever choices he makes and he'll be eternally grateful no doubt about that.
Anyway i'd love to stay and chat more but we have some promoting to do and god knows how long i'll last under this wig in the sun.
Byeee, mwa, mwa.
Baldric - he looks a bit trailer trash in that one but hey I wouldn't turn him away x I prefer the pic of him in the little black dress holding his rifle in a manly and erect manner x
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OK OK! my take on this ( I am not a Psychiatrist)
His cross dressing is a manifestation of what was once called Reactive or Exogenous Depression. This is the focus for any further psychiatric management.
Fueling or supporting in any way his "cross dressing" will further deepen his depression and may result in even more bizarre mental manifestations probably resulting in him being "sectioned."
AC...keep out of it and let the medics or psychologists take over.
That's it.
His cross dressing is a manifestation of what was once called Reactive or Exogenous Depression. This is the focus for any further psychiatric management.
Fueling or supporting in any way his "cross dressing" will further deepen his depression and may result in even more bizarre mental manifestations probably resulting in him being "sectioned."
AC...keep out of it and let the medics or psychologists take over.
That's it.
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