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This is a question Cross Dressing

The last time I wore a skirt was not as liberating or exciting as it could have been. I'd lost a drinking game and had been given the task of running from the bar, across the road and back again whilst wearing a friends clothes as a forfeit.

Easy, I thought. I hadn't reckoned on them getting every person in the pub to block my way back to the bar whilst I was outside. I had to FIGHT my way through. And I'm not much of a fighter.

Your own thoughts on cross dressing for fun, pleasure or profit are most welcome.

(, Thu 15 Mar 2007, 15:05)
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etiquette is important...
For the celebrations revolving around my 21st birthday I decided to have a 60's party. No other reason than I had procured a nude suit and a Hugh Heffner costume and had convinved numerous women to come dressed as my bunnies.

Anyway, one friend, a 6ft 4' lanky architect, decided to come as a bopper type woman. Loud colours, bobbed blonde wig, make up, the whole bit. He looked fantastic and was a hit with my token gay friends.

Anyway, his costume fell down at the shoes. They were entirely appropriate, but he couldn't find any heels that were fitting his massive, manly clodhopppers. So his size 11 feet were crammed to bursting into some size 6, or so, white kitten heels. Chunks of his feet were literally spilling over the sides and it was by all acounts very very painful.

So he was chatting to one of my girly friends at some point and was complaining about his sore feet. My lady friend informed him that in polite society it was acceptable for women to remove their heels after midnight.

Amazed, my friend hopefully checks his watch.

"Sh*t... it's still twenty minutes to". And proceeds to waddle around wincing for the next 20 minutes so as to successfully fulfil the etiquette imposed requirements forced on all women of certain standing.

What dedication!

My own cross dressing story takes place very early in my life when I convinced my Grade 3 class (about 8 y.o. I think) to perform Robert Palmer's, Simply Irresistable for the Christmas concert (I don't know. Don't ask). And we got the girls all in 80's suits and the boys all dragged up in miniskirts with tennis balls down their halter tops, gyrating around oversized pencils in front of their parents and the entire school community.

I'm amazed I'm not more messed up. Especially since there is a lot of photo and video evidence to remind me, my family, friends, girlfriends, family friends, family friends girlfriends, nieces, nephews, passersby, of the auspicious occasion.

Length: I was 8, but it still had to be squished firmly between my legs to avoid the disctubring bulge in my miniskirt.
(, Fri 16 Mar 2007, 11:29, Reply)

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