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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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This question is now closed.

a rare picture

of a man cross-dressing as a butch lesbian.

(, Wed 21 Mar 2007, 4:33, Reply)
Yall reddy fo dis?
For some reason, the 13 year old that spent my 12th year crushing my right testicle, and breaking my back by knocking my shoulderblades out of joint, decided to put me in her Mothers clothes and paint my face.  After getting this part done, she looked at me and exclaimed, "My God!  You're Beautiful!"

Fucking bitch still haunts me.  I don't talk to her except to tell her to shut up.  Sorry, I'll shut up now.
(, Wed 21 Mar 2007, 1:09, Reply)
it's pretty boring being a female in this topic, so here's my tuppence.

when I was in year 11 and getting my uniform, origionally I wanted to look good, fitted shirts, no jumper (we had a blazer and I had always worn a jumper underneath because I used to get cold) but then for some reason I decided I wanted baggy and with a jumper. Anyway. A few months in, for some reason I had no clean shirt and had to borrow my brothers. he was 3 years older than me and 6ft2 (I was only 5ft5 max). Me being the little weirdo that I was decided I preferred his big baggy, massive, boys shirts to my normal sized ones (which were too big anyway). So I wore them, lots. Anyway, one day in history one of my friends was sat next to me, and decided to tell me that, because I was wearing a boys shirt and the buttons were done differently, he could see down my top, he also told me he looked, aaandd carried on looking. Not cross dressing but hey.

EDIT: I've realised this topic is boring anyway. I remember nearly weeing myself when I read the masturbating QOTW
(, Tue 20 Mar 2007, 22:59, Reply)
New Shite Pun 'cos I've honestly not got anything better to say
My mum is a bit OCD and walks around Debenhams with a red pen marking all the frocks she doesn't like. That's right, she's a dress crosser.

Fucking hell, get this question changed NOW PLEEEAASE
(, Tue 20 Mar 2007, 21:41, Reply)
Xmas Cross Dress...
was many moons ago when one xmas, the band i was playing in decided to have the xmas gig we had booked to play, a cross dress affair...

also, the incentive was there for punters (£3 in for regular types, £2 for dole scum and £1 for anyone who came cross-dressed) to come already dressed up...

so, the stage was set...

we got one of the bands girlfiends to put our makeup on badly using the worst pound shop style face painting kits. the drummer had his girlfiends white mini-dress on, the guitarist had a netball skirt and top on....not too bad i hear you say...

well, the singer had a small pair of tie-side briefs and a matching bra...under a clear pvc mac....and me....?

as i was with a girl at the time whose entire wardrobe seemed to consist of leather/pvc/rubber (woo for me!) ...and who also had quite large feet (somewhere just smaller than me) the choices were vast....

fishnet stockings, pvc mini-skirt, black leather basque, leather choker, high heeled black leather knee boots (buckles and straps all over them) and a black fur coat....all topped off with a trowel type makeover.

i truly did look like the cheapest 'ho' and i defy anyone to find cheaper within 50 miles on that night...

the funnier thing was seeing my friends leaping off the stage in charity shop dresses and bad wigs...and girls in wartime spiv style suits with painted on handlebar moustache's...

was a great gig too (The Marys, @ the toby jug, doncaster, december 19th) i believe it was 1992, give or take a year, and should anyone who knows me read this and has pics from then, i'd love to see them as i lost touch with the one person who said she had some.... :(

length/girth? it's a nice story involving men in dresses......
(, Tue 20 Mar 2007, 21:08, Reply)
"I didn't do it... no, wait, I did... err, can I phone a friend?"
Can't say i've done much in the way of "proper" cross dressing, bar the odd piss-take with a bra in "the olden days". It's too risky - found out the kinda hard way. Anyway, the story...
... It was yet another lonely night in on the PC. Spent a while reading old QOTW's while I was in my lurking days, getting hammered on... err... orange juice (It's like an instant hangover, sans the fun part of being drunk, when you have it as un-watered down as I tend to - and hey, what can I say, i'm a lightweight). 'Tis all lonely in the XDeus household, what with everyone being asleep at this unsightly time of about 2am. Finally deciding that it's time to bugger off to bed, on account of no longer being able to see the screen, I set off up the stairs to the bedroom.
Now, this is one of those old terraced houses, and despite this lack of space, we tended not to bother with shoe racks, and leave any regularly used footwear on the stairs. Still giggling from some joke now forgotten, I saw my younger sisters shoes lying on the stairs. And, of course, something in the back of my mind decided that wearing them would be funny. However, what I didn't expect was to be able to fit my whole foot inside the shoe. And it was actually comfortable. Now, I'm a good size 10, so not only was this confusing in a Barely-Conscious way, but also in the way that finding out that your younger sister has feet almost as big as yours is. After being kinda freaked out, I slipped the shoes off again and finally went to bed.

The next morning, coming down to the rest of the family having breakfast (I was 15 at the time) and hear the sound of my mum having a bit of a shout at one of my sisters. Apparently, she'd gone and "deliberately" ripped a hole in the front of her brand new shoes, because she actually wanted a new pair (my sister was known for the numerous things that "just break" shortly after she said she wants a new one of whatever the said object was). In her defence, she said "don't worry, it won't be hard to get a new pair, I'm only a size 6. Now, with the morning brain still in gear, and memories of last night still vaguely there, I foolishly said "Size 6? Aren't you nearer a size 10?" FUCKSOCKS.

Thankfully for me, it wasn't all that bad. The caffeine kicked in as quickly as the silence, so I took the opportunity and quickly added "Well, you're shoes looked that big when you left them lying on top of my trainers a few days ago..." (she's also extremely lazy, forgetful and messy, so she never realized this was untrue, and everyone mostly believed what I said). So, anyway, she made a shocked remark at being indirectly called a "bigfoot", as I believe the term was back then, and the day carried on as usual.

However, as I was so convinced about their size, I just -HAD- to try it again with the new shoes - my mind just wouldn't let it rest. And, Lo and behold, they fit! And no rips or holes either!
So, where is this risk that I mentioned? Well, beyond that of your mouth working quicker than you're brain, I'm now convinced that women must use some special new size system for themselves that's beyond a mere man's comprehension. And, despite what I may desire to do, I now have a fear of going into a shoe store, asking for size 10 women's shoes, then finding that they're much too massive and having to ask for the smaller alternative, insinuating that my massive wooden weapon is actually a tiny toy soldier, thus spoiling the inevitable penis joke at the end of this post.

Apologies for length anyway - this far into the question I don't think anyone was expecting more than a witty retort to something else. Even if the story is crudalicious.

Click "I like this" if you also want rid of the women's shoe size code for the benefit of wannabe-tranny's and those of a curious nature all over Britain
(, Tue 20 Mar 2007, 20:17, Reply)
I was very, very drunk.
Dressed up as a proper girl in my sisters clothes for a fancy dress night once. Short skirt, make up the lot. Got absolutely bladdered and went to work next morning with terrible hangover. At work was getting some funny looks but not quite realising why. It wasn't until my bosses wife came up to me and told me that I should remove my make up before I go to bed that I realised. This was before New Romantics made it almost ok for men to wear eyeliner in public.
(, Tue 20 Mar 2007, 19:03, Reply)
Ok, ok - on topic

I was roped into doing a panto many many years ago - I forget where we were or the circumstances....

I ended up being Cinderfella - in the worst full length skirt in the history of skirts, with bad flat shoes, terrible top and naff wig.

I didn't look like a woman OR a man - I just looked rank.

The play wasn't that great anyway - Not helped by us all getting hammered first of course....
(, Tue 20 Mar 2007, 17:33, Reply)
Enough Already...
Can we break with tradition and have a new QOTW early please? Pretty please?

And to keep on topic.

Years and years ago (Christ, this'll show my age) me and a mate entered a fancy dress compo to celebrate the Queens Jubilee. He dressed up as a Northern woman AKA Monty Python style and I dressed up as a baby wearing a fuck-off nappy ( a white towel ) and a plastic football cut into the shape of a helmet and painted pink. A few slits were made in the helmet and wisps of my own hair pulled through.

We won. For "sheer nerve" as the judge put it. You should have seen the looks we got off the mummies and daddies of the brats we beat. They were fuckinh livid.

(, Tue 20 Mar 2007, 17:27, Reply)
two is not a load, two is a 'couple'.


im a pedantic dresser.

(, Tue 20 Mar 2007, 17:21, Reply)
fuck me
looks like I got a whole new load of ignores to hand out on here...unstabledan, james_tiger_woods, meet *click*
(, Tue 20 Mar 2007, 17:10, Reply)
UnstableDan is, in fact, a Dross Dresser
(, Tue 20 Mar 2007, 16:58, Reply)
i play that game where you catch the ball in a net on a stick and hurl it inot the oppositions goal.

I have to put on the full kit beforehand mind.

Lacrosse dresser
(, Tue 20 Mar 2007, 16:57, Reply)
Hag o' the Isle
For my GCSE Drama Assessment today, I had to play Sycorax from The Tempest. So I didn't just wear one skirt, on no, but two. One over my head as well. So I guess I have double the girl-power.
Why I was playing a girl I don't know. I may have long hair, but I also have a beard...
(, Tue 20 Mar 2007, 16:53, Reply)
that was shit JTW
ross dresser indeed.

what a terrible pun.

Im off to get dressed in that train station in London.........
(, Tue 20 Mar 2007, 16:42, Reply)
Just think
Someone on Friends was a Ross Dresser....
(, Tue 20 Mar 2007, 16:41, Reply)
I guess UnstableDan comes accross dressers then....

Not Sorry - apart from my spelling that is
(, Tue 20 Mar 2007, 16:39, Reply)
spent a lot f time pretending to be a female nurse.

red Cross dresser

bahdum tish.
(, Tue 20 Mar 2007, 16:37, Reply)
running out of rhyming words now.
If you put on an outfit made entirely of that stuff you use to clean between your teeth, does it mean you're a floss dresser??

next weeks QOTW had better be funny.
(, Tue 20 Mar 2007, 16:35, Reply)
dammit JTW, you beat me to it with the bros one
didn't matter, I was considered to dyslexic for that Bros' job, and was unemployed until a band comprising of 3 lovely irish ladies and their knobhead brother took me on board when they toured.

Yes ladies and gents i was a Corrs dresser.
(, Tue 20 Mar 2007, 16:34, Reply)
The Dukes
I used to work on a funky show with Daisy, Uncle, Luke, etc

Great sets, nice car, lots of banjo playing, shame I got a crap job on the show tough:

I used to be a Boss Hogg Dresser.
(, Tue 20 Mar 2007, 16:34, Reply)
I always knock one out whilst I put on my attire.

That makes me a toss dresser.
(, Tue 20 Mar 2007, 16:32, Reply)
I have lots of money and wear fancy clothes - that's right, I'm a Boss Dresser.
(, Tue 20 Mar 2007, 16:31, Reply)
I was in a plane flying across Germany - Had to Cross Dresden to get there

That's even worse than my last one FFS
(, Tue 20 Mar 2007, 16:30, Reply)
Mon oncle

On my mother's side once walked into the Houses of Parliament dressed in silk stockings, a flowing dress, white gloves and a big wig. He wasn't even thrown out when he bashed on the door with a big stick. It got filmed by TV cameras and he got a starring part in a porn film: Oh my Lord! Here comes the Black Rod.
(, Tue 20 Mar 2007, 16:30, Reply)
I only wear lichen scrpaed from stones or off the bark of trees.

Im a.......

MOSS dresser.
(, Tue 20 Mar 2007, 16:29, Reply)
scrape scrape scrape
i always used to put my clothes on whilst Tom O Connor presented that early morning quiz based on newspaper puzzles.

Im a crosswits dresser.
(, Tue 20 Mar 2007, 16:27, Reply)
The Band
In the eighties, I used to work for a band - I helped with their wardrobe.

Yes, dear reader - I was a Bros Dresser
(, Tue 20 Mar 2007, 16:24, Reply)
I've never cross dressed...
...but for a prank once, me and three mates went into the local church and put jeans and a t-shirt on a crucifix. Oh, I suppose I have cross dressed then...
(, Tue 20 Mar 2007, 16:24, Reply)
I met a famous actor and stamped on his foot - sufficed to say he was a Cross Dreyfus.

/leaves by the drainpipe
(, Tue 20 Mar 2007, 16:22, Reply)

This question is now closed.

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