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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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accidental txting
i did once wear a fake stick on tash....... er, it was a novelty gift! but anyway, i snogged my then boyfriend whilst wearing it, and, well, it was, er rather arousing actually, i can see why some men get off on cross dressing! the slightly embarassing part was remembering this incident some weeks later and txting my bloke to inform him of such..... and sending it to my sisters bloke instead.... whoops!
(, Fri 16 Mar 2007, 19:08, Reply)
Monty Boyce
Come on then, show us both piccies!
(, Fri 16 Mar 2007, 18:23, Reply)
Sexy nun fun
I went a bit over board cross dressing.
I dressed up as a sexy nun, however this included fishnets, thong, an awesome make up job and a wig.

We went to the bars got pissed, then later stumbled in to a random poorly lit club. I managed to pull a bird, however when she was kissing me she pulled the wig off accidently. She slapped me, her mates slapped me, the bouncers then hauled me out and "slapped" me. I later found out that I had pulled a dyke in a gay club! Damn you cross dressing antics!!!
(, Fri 16 Mar 2007, 18:16, Reply)
I used to go out with a guy...
He lived over 300 miles away, and when I first travelled down to meet him, one of the first things he confessed was his love of ladies clothing. More presisely his love of wearing ladies clothing.

In the bedroom.

I had to go back home the next day, but it was a rather eventful evening. With his mum and dad in the next room and him wearing a get up that would have made Dame Edna blush.

Split up not long after though, he looked better in most of it than I did.

Couldn't do his make up for shit though. Ha.
(, Fri 16 Mar 2007, 17:38, Reply)
I'm totally flabbergasted
by the guy telling the girl that he's into tranny porn.

Fine, you're into ladies and ladyboys. But basically, you're telling a woman "you know what'd make you really cool - if you had a huge cock and balls."

Even I know that that's unlikely to make the ladies feel special.
(, Fri 16 Mar 2007, 17:28, Reply)
Bastard hairdresser
When I was 11 a hairdresser thought that I was a girl and said to my mum "Do you think she would like a bob?" I had to meekly say "I'm a boy".

Bastard! It was probably my hippy-ish shaggy blonde hair.

Slightly off topic, but there you go.
(, Fri 16 Mar 2007, 17:02, Reply)
I cross-dressed today
As it's Red Nose Day, my school let us come in fancy dress...so me and my friend went as women. My dress and hat cost a total of £4.98 from the Oxfam shop. I took some pictures too :)

I'm the one in the red dress.
Picture 1
Picture 2
Picture 3
Picture 4

You can't actually see, but my hair (as it is quite long) is tied back with a flowery scrunchie. I'm also wearing blusher, eyeshadow and lipstick. The guy with the red tint glasses wears those for medical reasons too...Elton John jokes ahoy.

What can I say? I felt pretty.
(, Fri 16 Mar 2007, 17:01, Reply)
The Shame
This isn't quite on-topic but close enough I hope...

I have two embarrassing gender confusion tales to recount, dating back to the 80s when I was a fresh faced long-haired hippie type.

I was in a pub once and my mates overheard me being described as 'the roughest bird I've seen all year'.

Second one was me trying to go off on holiday to Canada several years later (when I had a shaved head but my 80s passport still showed me in full hairy glory) - nearly didn't get out of the UK because 'this is a lady's passport sir'.

So not exactly cross-dressing but I don't need to try it to know that I'd make an ugly bird.

Ah well
(, Fri 16 Mar 2007, 17:01, Reply)
What is it with people?
Looking at the answers to this question of the week, it seems quite common that real girls are being mistaken for blokes. And they all say they have D cups, or ample bosoms or the like.


I know the obesity epidemic is resulting in a lot more "moobs" on display, but come on, general public, persons with long hair and large breasts are usually female.

[Homer Simpson mode]

Mmmm - large breasts...!

[/Homer Simpson mode]

(, Fri 16 Mar 2007, 16:19, Reply)
This QOTW Reminds Me Of...

A drag queen (6'2" plus high heels) was running a trivia night at the local pub (long story...). Gets heckled by a drunken backpacker on the way back from the bar with some really imaginative line such as "you faggot". S/he puts him right in his place with:

"I am more of a woman than you'll ever get, and more of a man than you'll ever be!".

Not my story so don't click "I like" but worth a retelling methinks.

(, Fri 16 Mar 2007, 16:04, Reply)
I wasn't cross-dressing
I am rather petite male and went through a speed-induced Goth/gay faze in my teens. My hair was long and black, I had a full length black suede coat complete with fur collar. Flares. Platforms. I'm also naturally fair, so I had to tart myself up every morning so I didn't look like some odd gollum-type thing with no facial hair. With hindsight I was asking for trouble, really.

Anyroad, one summers afternoon after a rather hectic 48 hours of partying - read no sleep - I was walking through the town centre of a city in the South West when I somehow upset a vagrant by not getting out of his way when our paths crossed. He was undoubtedly in a great hurry to haul his shitty self into a Spar to buy some Special Brew.

I'm British, so I apologise.

He responds by calling me a vacuous hussy.

Hussy I took offense to. Getting home an hour later and finding out what vacuous meant in the dictionary made me livid.

I can't bear a verbose tramp on a comedown.
(, Fri 16 Mar 2007, 15:43, Reply)
i guess I should pitch in
I did dress when I was a bit younger quite a lot - i've probably got photos somewhere still, but they're not interweb enabled at the moment. I can probably dig one out at a push though.


clicky 1

clicky 2

At one party, there was me and a girly in fishnets, so we took a leg-only photo. 75% of those polled couldn't tell which pair was mine, and half actually said my legs looked better, so I guess that was a boon.

I never felt i was that passable, but lady friends thought I was.
(, Fri 16 Mar 2007, 15:41, Reply)
The Good, The Bad, and the Fugly Woman
Kind of related, but probably amusing.

Many years ago, pretty much the year after leaving the continuous drink and drug binge I like to refer to as "the time i was in further education", a mate and I had been out on the lash for much of the day following a failed job interview (stinking of 5 pints of dutch courage, weed and the remnants of bedding down on a mtes floor).

Walking back home via a road that acts as a sort of border between suburbia, and a hellish council estate, a group of three youths ran up, one with a knife held threateningly at my gut, the other two coralling off my mate.

To explain, my mates 6 year over indulgence in weed has left him rather slim, he also at the time had long hair, and was wearing a long coat, from behind, appearing to be a tall lass, imagine our would be muggers suprise when this lass, spins round to regard our would be assailants, sporting a full face beard and eyes with the level of blood shottedness reserved for those of Keith Richard level inibriation.

They didn't get a penny incidentally, once we realised they weren't mates of ours messing about, my mate involked his "tramp style" kung fu while i beat my pen knife wielding yob about the head with my NRA.

We only had a fiver...

That was us night caps sorted!

Length, Girth, Skill?
A Jedi needs not these things!
(, Fri 16 Mar 2007, 15:02, Reply)
People are very, very stupid.
A while ago, I got my once arse/ass-length hair chopped off to about shoulder-length. The bastard refuses to grow very quickly now.

Despite the fact that I'm close to being a D-cup, people have referred to me as "young man".

I carry sharp objects with me now, yes...
(, Fri 16 Mar 2007, 14:37, Reply)
Huh. 0.o
Sorry to say it's near-impossible for me to crossdress myself, seeing as to how I'm female and never wear "girly" clothes. Ever.


One of my really good friends (Piotr) just got married (in Massachusetts) to someone who is...tadaa...also a man (Mickey). Mickey is...ah...very effeminate-looking. Long blonde hair, blue eyes, you get the picture. More than once they've gone out on the town with Mickey in a skirt, just to see how many people mistook him for a girl.

...I think forty-three is our record.
(, Fri 16 Mar 2007, 14:25, Reply)
excuse me mister
I'm always getting mistaken for a bloke - I do have very short hair and I'm 5'11. Although not so much in the summer when my ample bosom is more noticable. I buy mens jeans - because they fit me better - mens t-shirts and sweatshirts - and I only buy womens clothing when a wedding or funeral is due.

I really must embrace my feminine side again - If all you men can wear womens clothing then I don't see why I can't give it another go.

Wish me luck!
(, Fri 16 Mar 2007, 14:24, Reply)
Sometimes I put my head in the arm-hole
Then I'm cross, dressing.
(, Fri 16 Mar 2007, 14:19, Reply)
equal rights for the boys in tights
I love transvestites.

when i was 16 i was moved from my abismal foster carers into my own bedsit in a block of flats specifically made for vunerable people.
(security on the door, help when you needed it etc..)

well, it just so happened that the majority of tennents were transvestites. I lived next door to a 'hooker looking' one called Fiona. (red high heels, red lipstick, short mini skirt etc..)

and actually... they were really nice! I locked myself out of my flat once and being a scared 16 yr old girl, they all rallied around and helped me get back in my bedsit!

thus the start of my love for transvestites.

I did a design course at college, and one of the projects, you got to pick any subject you wanted.

I decided to design posters for a 'transvestite nightclub' and took pictures of my male class mates in drag...

I think they thought it was more fun dressing up than I did photographing them! (all men secretly want to look like woman if only for an hour).

below is one of the photos i took of my mates, and one of the posters i designed (including my own 'storm' logo design)

by the way, some poster header ideas are as follows:

1) equal rights for the boys in tights
2) god save the 'queen'
there was many more, but you get the jist.

Image and video hosting by TinyPic

Image and video hosting by TinyPic
(, Fri 16 Mar 2007, 14:10, Reply)
Eat Your Heart Out Oedipus
Turns out that dressed as a woman I look exactly like my mother (discovered at an ad agency party dressed in black fishnets, short black skirt, red blouse and black lipstick). Not that my mother tends towards goth, but dressed like that she'll be one fine looking woman. *I* was.
(, Fri 16 Mar 2007, 13:46, Reply)
Wolf whistled
6:45am. Yeovil. Wandering back to my hotel from a hotel that I shouldnt have been in, barefoot, wearing a size 8 mini-dress, I got wolf-whistled by the entire crew of a dustbin lorry.
I cheekily asked if they wanted sucking off, at which point they beat a hasty retreat. Which is better than 'beating one off' I guess.
PS I'm no gayer, wearing dresses is a superb bird-puller. Try it.
(, Fri 16 Mar 2007, 13:41, Reply)
Good timing
I just had my new kilt delivered about an hour ago and have just noticed this QOTW.

One of the blokes I work with is always desperately trying to find the flimsiest excuse to cross dress 'for charity'. He goes on about it waaaaaay too much.

Just wear a dress if you want to mate.
(, Fri 16 Mar 2007, 13:40, Reply)
Wit Woo!
This QOTW isn't very lady-friendly :(

The only story I have of a little relevance is when I was out walking on a dark snowy night, dressed in my brother's massive baggy jumper, combats, a beanie and DM's. From the nearest Tesco Express I was wolf-whistled at by a pack of chavvy teenage girls. Hey ho, nice to know I could still pull, should I decide to turn lesbian.
(, Fri 16 Mar 2007, 13:27, Reply)
More nuts than a King Size Marathon
Back in The Day, when I was a long-haired Heavy Metal Guitar Hero (as opposed to the fat slaphead I am now), and my life revolved around alcohol, I naturally used to hang around with a gang of likeminded wreck-heads.

So, one of these idiots, sorry, my friends, was seeing a model. A gen-u-ine model, a regular in The Sunday Sport (back in the days before it became a Daily) illustrating some story she just made up, and, well, not exactly a rocket scientist. A lovely gal though, very docile.

Now, on the night in question, 6 of us ended up after the pub had shut round at her flat. Having woken the entire building by rampaging round doing Celtic Frost death-grunts, she was desperate to quieten us down.
"Look boys, look at all my sexy clothes" she declared, throwing open the door to the biggest wardrobe I have ever seen. It may well have simply been one room, it was immense, and we all hushed, as one imagining her in some of the frilly and lacy delights that greeted us.

There was all manner of wierd and wonderful things in there, it was like Mr Benn's secret dream. Dresses, nighties, uniforms, wigs, thigh-high PVC boots, more shoes than Imelda Marcos (mostly ridiculously high and made of clear perspex), underwear a-go-go, you name it, it was in there.
Suddenly the spell was broken:
"Fookin ell, let's dress up!!" from one of my comrades as he dived in, followed by the rest.
And me, I'm ashamed to say.
We were like kiddies, but at least we weren't playing human pinball listening to Slayer in her living room, so she was happy.

Some time later we emerged, dressed like Danny La Rue's sickest fantasy. Even today, my brain keeps most of the details suppressed, but I can recall I had a baby-doll on, and a Madonna-style metal bra over the top. I was dressed conservatively compared to the others. There was nurse, a dominatrix, plus assorted cavemen in dresses.

Suddenly, some bright spark decided it would be a hoot if we traipsed up to the 24-hour garage "to scare the queers" who worked there, so off we set, teetering on badly fitting over-high heels. Who knows if we actually got to the garage, but I do know that at some point a car pulled up alongside and 2 girls leapt out and took photos, and I distinctly remember they knew our names. I have no clue who they were, and no-one has ever owned up. I just know that one day, when the keys to No 10 Downing St are within my grasp, they will re-surface, pics in hand.

The worst thing, the thing that is seared into my memory, is Tommy, wearing a WPC tunic, hat, and erm, lingerie:
"Hey, hey, look at this.........Evening all!!"...... bending his knees in the time-honoured Rozzer fashion. It was the sight of his nuts hanging out of his split-crotch panties as he did it that haunts me.........
(, Fri 16 Mar 2007, 13:24, Reply)
I can confirm this is true. Genetically neither Flibbley nor I were ever intended to look as passable versions of the opposite sex.

I am not sorry.
(, Fri 16 Mar 2007, 13:00, Reply)
My parents dressed me as a girl all my life.
When I was a teenager they used to force me to have sex with all the men in the village so I could bring them a grand daughter.
But I only ever gave birth to a substance that looked like upside down top deck chocolate.
(, Fri 16 Mar 2007, 12:54, Reply)
Unintentional flashing in drag
One summer morning I was indulging in lazy ruderies with a lady of my acquaintance who was still living at home. Said lass thought it extremely funny to hide all my clothing in the bathroom so I was left bollock naked.

Obviously I was somewhat anxious to get my kit back, especially as I couldn't really drive home in the nip, so I picked up her nightie and used that for the purposes of covering my dignity while I retrieved my clothes.

En route I passed the open doorway of her thirteen year old sister, but as I did so my then g/f walked up behind me and yanked the fucking nightie up and slapped my arse.

Just great, my tackle was suddenly swinging out in full view of younger sis, it's a wonder that the sight of that didn't result in some emotional trauma. Good job social services didn't hear about that otherwise I'd still be doing time now.
(, Fri 16 Mar 2007, 12:48, Reply)
Post RHPS many years decided to order a pizza - GF and I swapped clothes for fun and frollicks and forgot the pizza order. As I was wearung the most I was sent to the door. Poor pizza boy he grabbed by proffered cheque and flung the pizza at me before leaping on his scooter and heading for the main road. I swear the bus missed him by less than an inch!

Length? None showing if tape up properly ;-)
(, Fri 16 Mar 2007, 12:45, Reply)
once walked into my mad old grandad's lounge and he announced,

"by 'eck that lad looks like our rswipe".

you'd think the DDs and the shoulder length dark hair would have given him a clue. or possibly the denim miniskirt and boots i was wearing. or even the mascara-lengthened lashes and glossy lips. but obviously not...

i shudder to think what the average "lad" must look like in halifax!
(, Fri 16 Mar 2007, 12:33, Reply)
Naturally, not me, but a "friend"...
A mate of mine who's now in his fourth year claims that the first time he had sex (or at least, the first time he had sex with his current girlfriend) he was in drag. Full drag. Make-up and all. As a schoolgirl.

I'm assured he had most of it off by the time they got around to the deed, but it does beg the question of whether or not she would still have bedded him had he not been dressed as a woman. So you've got to ask yourself... would you cross-dress for sex? Even if she only wanted you for how good you look in a skirt? (Of course, it's about the only way to actually be involved in some hot lesbian action, I suppose)

EDIT: One I forgot, reminded by the Rocky Horror post below. Fancy dress party, most of us are going as random things (I was a Union soldier from the American Civil War, I think). Anyhow, one of my friends decides to go as a prostitute. But not only does he get the tights, miniskirt, wig and boob tube, but also shaves his legs and gets high heels. It was bad enough when he went around trying to wrap his legs around everybody (including the father of the girl whose party it was). It was worse when he got himself so drunk, that on the way back home, in the back seat, with me sitting next to him, his stomach decides that it wants to cleanse itself, all over the driver, all over the back seat. God knows how I managed to avoid getting any on me.

We all jump out the car, outside some houses, with the driver (dressed as a Mafioso) screaming "What the Funk! Funking hell! Aww, funking hell!" for a good 10 minutes, waking up the dogs in the houses (Sean of the Dead censoring in effect there, btw). Anyhow, we get back in the car after more puking on the pavement, except the driver refuses to wear his seatbelt, as it's covered in vomit.

So we drive back, with a horrible alarm ringing in our ears (one of those clever cars which tells you that you're being irresponsible and not wearing your belt), the prostitute still spewing slightly, the two sober people in the car gagging from te smell. The filthy ho had also managed to puke up between his legs, so that it all squished into the tights and up his skirt.

We get back to the prostitute's house, but his parents are out for the weekend. I ring my dad (who was a policeman) to find out what to do with a catatonic prostitute covered in vomit. We grab a sheet, throw it over a leather sofa, get th drunken arse onto it, cover him up, leave him a cup of water etc. The absolute worst bit of the night was seeing half his face (and the wig) caked in drying vomit, and the feeling of pity at him having to wake up to the aftermath of Aliens.
(, Fri 16 Mar 2007, 12:31, Reply)
I have a friend, let us call him Mike, who really went the whole hog when it came to fancy dress parties. While the rest of us would spend our hard earned teenage money on the cheapest, cheeriest outfit we could lay our hands on, Mike would turn up in proper, shop hired or bought attire.

So this one time, one of my friends parents were away for the weekend - so naturally a Rocky Horror party was to be thrown. Now, whereas most of us just went for the gothic clothes, big hair and makeup - Mike went for the proper Tim Curry, Dr Frank N Furter suspenders, black knickers, corset and afro-esque wig.

He proceeded to get absolutely wankered, doing the usual "I love you, I do" to all and sundry. Eventually we dragged him into a taxi to head to his house where we were all staying the night. After an eventful ride home (He proudly exclaimed to the driver "I live at number 66 - one more 6 and it'd be the house of the devil") we arrived in one piece at his parents house.

7 pissed teenagers trying to enter a house quietly in full tranny garb at 3 in the morning was never going to happen, and his parents (who were, bless them, very understanding) came down the stairs in their dressing gowns, followed by his brother and sister, and then his extended family (grandparents, uncles etc) who were visiting.

Mike's mother lightly chastised him for making a noise, and his response? He grabbed his little black knickers and pulled them down to his knees - exposing himself to his entire family for at least half a minute of shocked silence, before we bundled him into the other room to sleep it off.
(, Fri 16 Mar 2007, 12:27, Reply)

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