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?

[friedgreentomato]

Help him he is trusting you to do the best by him - so help him to the best of your ability.

[Sharingan]

I think it's lovely that he trusts you to share this new side to himself. just be friendly and supportive and take your cue from him how much he wants you to be involved.xx

[ummmm]

Help him.

[Sqad]

Let's see........
You go into a shop with your male friend and you help him try on bras and knickers...........that shouldn't cause a problem....seems natural to me..................LOL......LOL.......LOL.....LOL

Don't forget SILK blouses and little knickers....for .....hmmmm! your friend.

[andy-hughes]

If you are comfortable helping him, I see no reason not to.

It says much for your friendship that he is able to share this very private and intimate aspect of his life with you - I would feel very special if someone felt that close to me.

[society]

I now understand why you named yourself 'AlwaysConfused'. :)

[Sqad]

society...LOL

[magsmay]

His whole world has turned upside down -the things he defined himself with -partner, parent, pet -all gone in a short space of time and he probably feels like he's lost his identity. If this helps him cope then support him -charity shops might be your best bet as it may be this is a phase and he doesn't want to be left with a wardrobe of expensive womens clothes. There is a possibility of course, that these feelings have always been there but suppressed -I know of two males who married had children, then in their late forties 'came out' and are now happy in homosexual relationships. Whatever the outcome support and be non-judgemental -which you seem to be doing already so keep up the good work !

[magsmay]

Ah! Sqad -thats what you were doing in La Senza last week -trying on women's knickers -think you will find woman haven't worn 'knickers' since 1960 - oooo matron...;-)

[Sqad]

http://www.dailymail.co.uk/femail/article-2313384/Would-YOUR-man-wear-frilly-knickers-HommeMystere-launch-lingerie-line-lacy-thongs-bras-MEN.html

Seems perfectly natural to me........

[AlwaysConfused]

Cheers mags. He has had a lot to deal with lately. He used to take great delight in buying his wife pretty dresses, I just don't know if he is missing her more than he is letting on, or if these crossdressing urges have been there for a while. Yep, I will support him. You've all made my mind up! I'm still gobsmacked by his revelation, though!

[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.

[RATTER15]

Go help him, He will need a lot of help im sure, he probably has little idea womens clothing. Also advise him on makeup, that will be a minefield for him im sure, assuming he is also going down that road.

[AlwaysConfused]

Ermm, I'll help him with dresses Sqad, but I wouldn't help anyone choose underwear! Cheers for the link, though!

[magsmay]

Sqad - send me your address and I'll buy you the blue knickers -to remind you of the war ;-)

[Canary42]

Hardly a case for mockery and laughter - especially from one who should know better.

I agree with sharingan.

[RATTER15]

Tony, I never understood why Women do that, so inconsiderate!! Leave it up!!

[tonyav]

I know Ratter, bloody inconsiderate imo !

[AlwaysConfused]

Tony, he wears a bag so that's those tell-tale signs out of the way! No, he's not girly at all. The only female trait he displays is his ability to chat chat chat!

[magsmay]

I think you may have a point with him enjoying buying his wife dresses and him missing that. Years ago a colleague who was a bereavement counsellor came to me in a professional capacity worried that an old man she was counselling kept bringing her chocolate when she went to see him for therapy sessions - I advised her to ask him not to do it anymore as it was 'against the rules' -when she asked him not to he admitted that every week he bought these particular choccie bars for his wife and buying them and giving them to the counsellor kept her memory fresh. You can buy underwear on line -then take him shopping and perhaps suggest he enquires about bereavement counselling -just someone to talk to who is not a friend sometimes helps enourmously.