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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.

My God ! I'm just like everyone else
And there I was thinking I was one of a small select group of women who have a fetish for cocks in frocks - It seems I'm not as special/ kinky as I thought I was.
(, Mon 19 Mar 2007, 14:14, Reply)
v baggy hawaian shorts
was accosted in local pub whilst wearing these: I think you're very brave coming in here wearing a skirt...you're my best mate etc.

one week later, whilst barbecuing and wearing a sarong in't privacy (or so I thought)of me own garden heard: you fucking pervert!
straw poll: drunks like men in skirts, sobers don't....

(I've nibbled but not et a whole one)
(, Mon 19 Mar 2007, 13:47, Reply)
I played the Gabby Hayes character in a pantomime a few years ago. Strapped the chest down (ouch) and glued on the full length baccy-stained beard. Baccy stains were made mostly of mushed up flour paste and soy sauce, so by the end of the week's run no-one would come near me because it reeked. Peeling it off was a bugger too.

Oh, and once a year I shave my husband so he can play the panto dame.
(, Mon 19 Mar 2007, 12:47, Reply)
when i was 13 and a metal head we went on holiday to spain with good ole' mum and dad.

before going, we did the obligatory 'buy some holiday clothes' and i picked out a rather natty black shirt with pentacles drawn on it. i thought that it was the shit!

turns out that it was a size 10 blouse. i had this pointed out to me by virtually everyone that i met whilst wearing it.

blouses are definately not the look for emo-esque thirteen year old boys apparently. bitches.
(, Mon 19 Mar 2007, 12:29, Reply)
everything but the dress
at an old workplace, during training at one point we had to fill out various things about ourselves like our favourite film, favourite actor etc.

I put 'Titanic' as my favourite film. I don't really follow actors, but because I liked both 'Titanic' and 'What's Eating Gilbert Grape' I was going to put Leonardo DiCaprio - but I decided to put Kate Winslett instead.

Anyway they didn't tell us what these questions were for, and nothing was heard of it for several weeks. Then the trainer explained it: she was going to read out the answers, and we had to guess who the person was.

When it came to my answers, she read 'favourite film is Titanic' and someone said 'this'll be one of the girls, chortle chortle'.

I was glad I hadn't put Leonardo DiCaprio.
(, Mon 19 Mar 2007, 12:17, Reply)
there was a guy

who was a friend of a friend. He was fairly dark, and had odd hair - something like a top knot and a big mustache. He also wore a flowery-printed robe thing. All in all, I assumed he was from overseas and wore traditional dress of wherever he was from.

It turned out that no, the 'robe' was actually a dress, and he was just a guy that wore a dress.

The odd thing was he wasn't trying to look at all like a woman: mustache, sneakers, no stockings or make-up.
(, Mon 19 Mar 2007, 12:14, Reply)
Women's pants more comfortable???

D'you mean:

Thongs - becuase they can't be comfortable
"Hold in pants" - er, ouch
Bras - well, I spend half my time trying to get in to one - why would i wear one myself
Boy-shorts - I've got my own thank you
Big pants - Er, I'll buy mine from Next (the man's section) or something
Suspenders - Er. No.

Or am I missing something?
(, Mon 19 Mar 2007, 11:06, Reply)
This won't go down as one of the best QOTWs methinks.


There was this guy I used to play 5-a-side again - huge guy - the size of several houses - mostly muscle. A manly man. More man than, well, actually not all that much of a man.

My Mum used to work with him and I went round to see her a few years back - I remember this guy and I asked "So how's Bomber*?"

Cue a LOT of laughter from my Mum while she told me that Mr Manly Man had gone from Manly man to a flowery dress man - with facial hair. I saw him a few weeks later and he wasn't even close to looking like a woman - he didn't even seem to be trying.

It was the oddest thing, but you'd've thought he'd at least shaved.


I apologise for the lameness of this post, but I was drinking Bucks Fizz on the plane this morning and my brain refuses to fire.....

Bomber - his surname was Lancaster - get it? No, I didn't make it up and yes, it was a shit one
(, Mon 19 Mar 2007, 11:03, Reply)
The thing that I want to know is: why are womens knickers so much more comfortable than mens pants? Why can we not have pants made from the very soft material the same as knickers. OK, so they might wear out a little quicker, what with the extra strain they must bear, but let us face it, most guy's underpants have a longer life than the average boy band, so replacing them slightly more often might be a good idea eh?

(, Mon 19 Mar 2007, 11:01, Reply)
Unexpected publicity.
The local pub ran a 'Miss Bull 95' night in which all of the men folk had to dress up in their wives/girlfriends clothes. I managed to get quite drunk that afternoon and decided it would be a good idea to join in that evening.

I staggered back into the pub at about 9:00 wearing a dress, makeup, beard etc. I looked like a drunken Elizabethan trollop.

Much to my amazement I won, and then vaguely remembered having my picture taken with Liz McDonald from Coronation Street (the one with the violent Scottish husband).

The next day we went past a newsagents and my friend said 'why don't you get the local paper and see if there is any mention of the night before?'

I thought something wasn't right when several people stared at me when I walked in, but it made sense once I saw that the front page of the Lancashire Evening Telegraph consisted of a picture of me and 'Liz' with the headline 'How drunk would you have to be to do this?'

Mother was not pleased...

Yes - I have the pictures, but they are staying on my hard drive thanks.
(, Mon 19 Mar 2007, 10:25, Reply)
The things kids say...
I was obliged to escort a young cousin about town one day. The little lad was from the countryside and had led a very sheltered life (his parents have no TV and make him practise the clarinet all day.) So - we were walking past a Catholic church and a priest emerged. Cue little cousin shouting: "Look, that man's wearing a dress!" I had to explain that it was not a dress and that the man was a priest.

Later, we came across a hippy guy selling incense sticks. He had a long pony-tail. Quick as a flash, little cousin says, "Look - that man has long hair like a woman!" I had to explain to him that some men choose to wear their hair long and that he should be tolerant.

The very next hour, we saw a group of emo boys loitering outside HMV. They had long asymmetrical haircuts, earrings, make-up and the typical attire of the emo kid. "Look!" shrieked little cousin, "A bunch of attention-seeking, cross-dressing tossers who need a good kicking!"

"Good boy!" I said. Let's go for an ice-cream."
(, Mon 19 Mar 2007, 9:38, Reply)
P.E Sadistic Bastard Crossdressing Shame
The P.E Dept at our school was run like the Royal Marines All Arms course due to the head P.E teacher being an ex bootneck and a complete sadist
If it wasnt meeting out actual pain to his youthful charges he was humiliating them..
One of his favourite wheezes was to ritually humilate anyone stupid enough to forget their P.E kit.....like yours truly for instance
Id committed the capital offence of forgetting my shorts, so off I trotted to his office to see if I could borrow a pair from the sizeable collection of spares he had gathered
On enquiring if I could borrow a pair he told me that he only had girls netball skirts and that Id have to go out in one of the skirts..of course I didnt want to but my protests were met with hissed threats of 'get outside you little queer or Ill put my boot up your arse'
I did as I was told and spent the whole hour of P.E blushing red and trying to stop my testicles from escaping from the bottom of my pants
(, Mon 19 Mar 2007, 9:30, Reply)
I used to be a bit of a goth

and goth clothes for women are way more elaborate and better than those for men, and generally I find that goth women look a lot better than goth men (although that may just be my 'breeding filter').

So I'd like to wear goth women clothes, if it made me look like an actual goth woman, rather than what it would make me look like ie a hairy-armed stick insect in a corset.

Also, if I was a woman I could play with my boobies all day.
(, Mon 19 Mar 2007, 6:37, Reply)
This chap I know

There was a "rock night" at a pub in our home town that used to run every friday and was a good excuse for all the goth kids to dress "extreme" and leave the good pub alone for a night so we could all drink in peace. They all tried to outdo each other in terms of kerayzee outfits and some went to remarkable lengths.

One night said chap-I-know went down there dressed as a woman, for shits and giggles apparently. It was shockingly convincing, from the back you would think he was a woman, with a remarkably short dress, long wig, fishnets, make-up etc etc. Several guys left feeling confused, everyone else left feeling amused and a remarkably mediocre night was had by all.

The next day this chap was being remarkably positive about the whole incident and seemed to have enjoyed it a bit too much. He asked me to go clothes shopping with him, to "this ace fetish place in wolverhampton that have some really nice PVC skirts" (I said no after I had the inside giggles sorted). He brought fake nails, he never took the wig off, he started going around town in dresses...yep, the experience had turned him into a full-blown transvestite. It wouldnt have been so unnerving if, after asking me to go clothes shopping with him, he hadn't asked me out. FEAR.

He now can be found every weekend in town in full-on womans clothing with his girlfriend. They swap clothes and everything, its quite bizzare.
(, Sun 18 Mar 2007, 21:22, Reply)
Tranny Man, the greatest poofter of them all!
When I was younger, I dressed my little brother's Action Man in Barbie clothes.

My brother went mental, but I didn't hear Action Man complaining.
(, Sun 18 Mar 2007, 21:04, Reply)
Post rocky...
Went to the last night sow of Rocky Horror a few years back and was generally dolled up (red corset, stockings and suspenders, pearls, lots of makeup, big black boots and long trenchcoat).

Firstly, went to the loo just as the show finished. Picture the scene, row of urinals, 7 blokes all dolled up to the nines and one guy at the end who looked like he had just come from work.

In the hush, all of a sudden...

"who's the weirdo in the suit?", piped up one of the guys, causing all of us to crease up.

I had a few women saying hello in a "nice to see you again" kinda way (I thought maybe they were some of the girls from work...) only for my wife to point out that "I don't think you know them, they probably want a shag as they've been eyeing you up all night...."

Next it's off to the club next door. I'm chatted up 4 times before I get to the Bar and the wife ends up dancing with a group of Lesbians (all in rocky gear) who keep asking her out in all seriousness...

Stick on a dress and go to a pub=guarenteed pull (and not just by the law..:) ). Oh why didn't I realise this in my youth? :)
(, Sun 18 Mar 2007, 21:03, Reply)
African Queen
When I was a 6th former I had a part in the school production of 'Jumpers', the Tom Stoppard play. In one scene my character is playing charades and is doing the film 'African Queen'. The teacher in charge made me wear a flowery dress, black-up my face and run around screaming.

Quite a change from being a respectable scholar and prop forward in the rugby team.
(, Sun 18 Mar 2007, 20:22, Reply)
dodgy tradition
on the skiing trips at school it was a yearly tradition (went a few times) to split up into groups and dress a fella in the group in female members cloths. We were 12-14 at the time and I only realised when 15 how pervy this is for the teachers to organise :S
(, Sun 18 Mar 2007, 19:44, Reply)
Polish bananas
Poland, early Nineties, working as an English teacher in a town that had been slower to embrace change than the rest of the country, and was, shall we say, a little less than tolerant of deviants (whilst seemingly being full of people who seemed to want something very specific to do with them...)

Anyhow, a colleague decides to have a party, and to make it a little different, also decides that it should be a “Red Party”, meaning that everyone should wear something red. A friend, who, being Lucy, will remain nameless, decided that she and her friends should outdo the rest of the party, and thus eight people should go dressed as a red light district. There seemed to be some sort of logic to it at the time, but this has been lost in the mists of time and vodka.

The day comes, and the other lads take possession of the stock of fishnet stockings, skirts and bras offered by Lucy and Rachel (who will also remain anonymous). Groover J finds himself rather at a loss, as all the truly good stuff has been nabbed. At Lucy’s suggestion (there may also have been vodka involved), it is decided that going as a rent boy will complete the red light district’s charms and services.

So, off we go. Pink shirt open to the waist (with rather a camp medallion), tight leggings, clogs (clogs?), a dinky little hat, half a dozen earrings (made from paper clips), copious make-up, and, logically, a banana stuffed down the leggings. God only knows what I looked like. The vodka excuse now sounds more and more likely.

Off we go to the party, in a taxi. On the way, we had to stop at the major station to pick up cigarettes. Lucy dressed like a Soho cocktail whore, Groover J in his finery. I swear, seeing some of the looks (and unintelligible Polish comments), we could have made an absolute killing that night, there and then, at the station, if we had been so inclined (no way, as far as either of us were concerned).

Of course, we get to the party and no sod is wearing anything red, and we look like a bunch of tits. On the up side, I did get sufficiently hammered on vodka to go around asking all the girls if they’d like to feel my banana…
(, Sun 18 Mar 2007, 15:22, Reply)
We swapped clothes....
Hmm…cross dressing Army chappies….having read the illustrious Ms Swipe’s post, I am of course impelled to recount my experience of Army boys dressing up….

Some years back I had a rather (over)long relationship with a member of Her Majesties Armed Forces….red tunic and bearskin no less….So he was very familiar with dressing up on a daily basis….

Anyway, we had been seeing each other for some time and I had a uni ball to go to…so he dragged out his number one (or maybe it was number two) uniform – the smart one that wasn’t a red tunic and bearskin…

We went off to the ball, me dressed in a little black dress covered in tassels – a bit 1920s-ish, think flapper but rather shorter…ahem….

Had a lovely time, drank much wine (so what’s new?). Head off home just as the sun is coming up…

Get home and despite crashing hangover beginning to warm up, he’s feeling frisky….not usually a problem – helps to get rid of a hangover I’ve generally found….

But, here’s the killer…”Erm, Chickenlady, why don’t we swap clothes? I bet you’d look good in uniform…and I could try on your flapper dress….”

Oh….Interesting…..He was over six foot tall – but very slender, if muscular (calm down ladies, I’m trying to keep calm myself here….) I did worry, albeit briefly, if he’d ruin my dress – size 12 (UK, not huge US)….OK says I….(actually, pissed, so up for anything at that point….)

So, we swap clothes…..his trousers are too big in the waist and too long in the leg (bastard long legs!) the jacket doesn’t fit across the bust (Yay for boobs!)…so all in all I look … odd..especially as I have long hair…

However, he looks bloody fantastic! Legs that go on forever – muscular and toned (if a bit hairy, but he was blond…) Fabulous shoulders and arms (thin spaghetti straps…) and the bloody dress isn’t stretched to buggery!

Yes, shortly after that I kicked him out – how on earth could I be with someone who looks better in a frock than me? Bastard.

Mind you, that was only if you ignored his head…broken nose…hard as fuck Geordie….but the body was sublime….
(, Sun 18 Mar 2007, 15:16, Reply)
Not technically cross dressing...
I went to a "tarts & vicars" party (highly unimaginative theme, but not mine) recently. Of course, most of the lads went as tarts and most of the women went as, err... tarts! I thought there was going to be poor representation of genuine male tarts, so I went as a rentboy (think hotpants and eyeliner). It was a thoroughly lovely evening for all concerned, but due to the hosts occupation, a number of the guests were academically challenged labourers. I was chatting in the kitchen to a bunch of them when it turned out they thought I was actually a bummer! What sort of person goes to a fancy dress party as themselves for flock's sake I asked them?!

(The story hereafter is entirely fictional and NSFW)

Anyway, it turned out they were all massive YMCA loving bum funners themselves and they took turns to push their swollen members into my rusty sheriff's badge. I fought very hard but apparently they were well into "strugglers" and I got man juice all over me, it was horrible, eventually I gained the upper hand when they were relaxing with post-coital cigarillos and I killed them all. Secure in my sexuality I went home and relaxed, reflecting on what a surreal evening it had been; being penetrated by six strapping transvestites.

The end.
(, Sun 18 Mar 2007, 14:18, Reply)
Halloween 05
When I was living in Leeds I was part of a soundsystem, doing free parties, clubnights etc. I was the monkey boy, if a speaker needed moving, I was the one. Someone left a wire at home? I was the greyhound sent. My perm position was the doorman, taking the punters money, stamping them like an Austwitz guard and all that. Comes to halloween and we're doing our night in an old workmans club in Woodhouse, a very grim and chavtastic part of Leeds, locals in one room, yogurt weaving dub and reggae loving hippy trustifarians with credlocks in the other. I'm there working the working the door in the ex's denim mini, flip flops, a marker tattoo of a willy on the inside of my thigh, make up and matching gold belt and handbag (if you're gonna cross dress then at least make sure you accessorize propery peeps)

Going to get change from the local chippy with the stellared up yokels waiting for their sausage in batter and chips with me dressed like a pretty version of Victoria Beckham was fun.
(, Sun 18 Mar 2007, 11:53, Reply)
I didn't enjoy wearing my girlfriend's underwear

it was pants.
(, Sun 18 Mar 2007, 10:29, Reply)
army boys
does anyone here know why army boys enjoy cross dressing so much?

my ex oswald, despite being skinny and hairless of body and having a nose with its own postcode and generally looking more like a starving baby bird than an officer and a gentleman, had a commission to join the army after university. he wasn't actually that army-ish, but my god some of his mates were truly awful.

two occasions stand out. the first a truly shit party at a shit house down in battersea. the "boys" were in fancy dress, and as we arrived they were ignoring the sad droopy breasted stripper who was gyrating to herself in the lounge, and instead having a competition to see who could stuff the most brown m & ms up their arses. i must point out that my ex was doing neither on this occasion. do you really think i'd ever have slept with him again if he had!?

anyway. in an effort to mingalise and not to look too snotty, my flatmate said jokingly to the hairiest burliest bloke in a pink woollen mini-dress that i hope i ever see:

"i hope you're wearing underwear!"

to which loz, for this was the name of the beast, casually lifted his skirt and flopped his tiny semi-erect self into his hand.

"nope," he said proudly, as if showing us a fucking rock hard 8", "that's my cock." then ran off to grab a fistful of m & ms with which to distend his swollen hairy brown eye even further. eeeeeow.

the second occasion was at our uni bar, and all the army boys were in fancy dress "just because". my ex was wearing a skin tight black and white minidress and boots, and more eyeliner than a goth chick, and i have never seen a guy get so much attention from the ladies. again, anyone know why this is??

so he was flirting with this girl and then drunkenly said something about having bigger tits than she did. the next minute her enormous boyfriend loomed into sight, and brandished a huge meaty fist at the cowering ropey tranny in front of him. and what did oswald say?

"wait there. i'm just going to get my big mates to deal with you."

and this guy is now a major or something in the army. jesus christ. that is all.

apologies for length, as oswald sure as hell never made any.
(, Sun 18 Mar 2007, 9:57, Reply)
geographical cross-dressing

my friend was from the U.S., but secretly enjoyed dressing as a Canadian. He said he got quite aroused by being able to freely express an interest in ice hockey and say 'eh?'.
(, Sun 18 Mar 2007, 9:03, Reply)
Cross Dressing is dangerous.
One time I was in a bad mood after an argument, and pulled my jeans on too quickly. Zip... ARGH! The moral of the story is: don't cross dress; take a deep breath, sit down and count to ten, before putting any clothes on.
(, Sun 18 Mar 2007, 3:44, Reply)

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