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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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Back in the day...
When I was at school, we had the annual 'House Music' competition - it was an absolutely fantastic night, with hours of singing, dancing, and general hilarity. One thing which was very frequently occurring however, was cross dressing. This was generally confined to the sixth formers (of which I was one at the time) - it was rare to get through a the night without someone prancing about in a rather nice man-thong whilst wearing a pair of comedy breasts.

In my last year, we pushed it further, splitting our 70ish strong choir into two halves - boys and girls. Not that impressive, till you mention it was an all boys school. Cue 35 boys & men dressed as women, and 35 boys & men dressed as... Well, men prancing about on stage - impressive but not massively embarrassing. Unfortunately that part of the story is related only to me.

I was wearing a rather nice (and very short) skirt, which, in the absence of a proper skirt, as just a 30cm bit of material pinned round my waist. Underneath, I was wearing baggy boxers. This would not have been problematic normally, but I was also playing the drums (with great style, it must be said). We all file into the hall, and I sit down behind the drum set. *Riiiip*. Oh shit. My skirt is now open. Glance down. And oh, look at that. My left testicle is hanging off the edge of the chair I'm sat on, swinging gently. And hairily.

So there you have it - due to an unfortunate cross dressing incident, I exposed my left testicle to the whole of my school and their parents. "Oh cock" seemed an oddly appropriate comment after the moment...
(, Fri 16 Mar 2007, 23:56, Reply)

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