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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.

Ho hum, no need for *me* to cross-dress...
Went into the Jobcentre when I was fresh out of uni and a scatty man who worked there was running amok looking for someone whose name was on his clipboard.

He looked me square in the eye and asked tentatively, 'Jonathan..?'

Now, being of the female persuasion, if it had been a non-gender-specific name I wouldn't have been quite so offended...then again I might not have been persuaded to pluck my mini-beard and monobrow (I jest...

...it was more of a unibrow definitely).

On a different note, to the man from Glastonbury 2004 who wore a big fat nothing under his kilt and felt the need to hitch it up until someone threatened to have your bollocks for breakfast - skirts are NOT FOR YOU BUDDY.
(, Thu 15 Mar 2007, 21:56, Reply)
the first day back for year 10
I was struggling to adjust to getting up after a summer of sleeping till noon and beyond. Rather than subject my sleepy eyes to the bright light beyond the curtains I chose to dress in the dark.

When i got to school i realised i was wereing blue trousers. Now at my school this was girls uniform and tantamount to wearing a skirt. Being 15 evryone picked up on it.

"lolzors, willenium why did you dress as a girl for the fist day of the most hormonaly charged year of school?"

me:"it was dark and i was tired fuck off"

No one would belive that it was a genuine accident and i had to wait for two girls in my year to get pregnant for the focus of gossip to change away form my wardrobe malfunction.

I fucking hate mornings btw
(, Thu 15 Mar 2007, 21:52, Reply)
here we go (this is me)
(, Thu 15 Mar 2007, 21:50, Reply)
dog food
for a tiny gig at a friend's birthday party, me and my band were to play, so i spent most of the day using duct tape and a big dog food bag crafting a nice skirt.

the show went badly and we ended up calling it quits as a band mid-song, me still garishly clad in a short, tight dog food bag skirt.
(, Thu 15 Mar 2007, 21:15, Reply)
Dirty Ride
not me, my friend who we shall name garry the goth.

He got taken to a new bar that opened by his girlfriend and her two gay friends. he was chatted up by an elderly gentleman wearing what he describes as the shortest skirt ever. how was he chatted up i hear you cry?

"I bet your a really dirty ride!"

followed by at a later point in the evening when garry was with said girlfriend;

"this your girlfriend? she's rubbish, i'm more woman than her....."
(, Thu 15 Mar 2007, 20:34, Reply)
Another story
From another party. During this rather drunken party, I swapped clothes with this girl, and she tried to epilate my armpits (ow ow ow ow - it drew blood). Anyway, more drink was drunk, and pictures were taken (I don't have them, sadly) but anyway, a couple of weeks later, the guy who took the pictures was showing them to another friend, came to this picture of a girl in a red dress, said "this is the girl I really fancy" zoomed in on his camera, and it was me. Cue much back tracking.

Also, I noticed I'm getting an awful lot of hits on my website from my message below, I'm wondering whether people are hoping for pictures. If you really want to see, send me a message, and if you're nice to me, I'll send you a link.
(, Thu 15 Mar 2007, 20:32, Reply)
I would like to
reply, belatedly, to the guy who said, "I'm gay and you would never even see ME dressed up like that" to the bunch of chaps in old ladies dresses hanging around out the front of Oxford Street mcdonalds a couple of years ago.

Granted, someone easily clearing six feet and build like a shed*/ a fat bastard* wearing a floral dress tailored for the sensitivities of a septagenarian, paired with army boots, and his similarly attired chums, may look a little ridiculous but at least I've never KISSED ANOTHER MAN ON THE MOUTH!

There, I win.

*delete as
(, Thu 15 Mar 2007, 20:18, Reply)
You know what they say
You know what they say
If a Man builds a hundred bridges and sucks one cock, people dont call him a bridge builder.

Click i like this and i'l show u a pic of the bridges :P
(, Thu 15 Mar 2007, 19:45, Reply)
unfortunately the last time i put on women's clothing was when i was a kid
prancing around in mum's shoes, but a friend of mine once got caught by his dad weiring his sister's song...he'd taken out of the wash!!!

never was quite the same relationship with his dad after that night.
(, Thu 15 Mar 2007, 19:37, Reply)
I wear a shirt under a trendy jumper
And with it I wear a scarf and some trendy jeans.

Please help me, I'm turning gay.
(, Thu 15 Mar 2007, 19:29, Reply)
My fragile young mind
My first experience was at 14, and was not my own choice. Our English teacher was taking us for some lessons in drama, so we could enact her own mini-play. I had never acted before, but boy, she'd found the perfect part for me!

"There's only one female part in this production I'm afraid - and I want Stephen to play the role"

"But why miss!?" came the confused/disturbed reply from the girls in my class. From the look of the rest of the boys in the class, I think they had even less desire to see me dress up as a woman.

"Because he's got the most child-bearing hips" was her flattering reply.

Well, I could hardly resist a compliment like that. So she took me into the clothes cupboard and picked out not only a lovely long blue dress for me, but also a flowing blonde wig. I put these one and took one look in the mirror, and bloody hell! She was RIGHT! I passed for a girl much better than most of the girls in my class - and I was HOT!

So I came sauntering out in this saucy number, and took part in this little play she had written for us. After my part was done with though, I decided I didn't want to change back for a while, so while the rest of the play was being filmed, I snuck out of the room and began dancing round the school waving my hanky at all the boys in school. I stood outside one first year class winking and blowing kisses at all the kids in the room. Some laughed - one screamed, so I had to scarper.

Another teacher encountered my nonsense and asked me just what I thought I was playing at. "Oh you silly!" said I, and pranced off back to class.

Said teacher apparently still has this video of me playing a beautiful young lady apparently. She was so proud, she played it to several other classes.

Now I actually reflect upon this, it may explain why I never got asked out by girls at my school.

(, Thu 15 Mar 2007, 19:17, Reply)
i like
manly men, guys who are very effeminate don't really do it for me.

but oh my GOD when i went to see the rocky horror show years ago, the guy who was playing frank n furter, the one who struts around in corsets and stilettos and fishnets? jeeeesus christ.

not a dry seat in the house, not even for a moment.

(although sympathy for my friend, we were about 16 and we ended up going with my parents who had last minute spare tickets. she was sitting next to my dad during that scene when he scarfs down not only his own spunk but brad's as well...)
(, Thu 15 Mar 2007, 19:11, Reply)
whether male -> female cross-dressers look like women

the funny thing is that men tend to say they don't, whereas women tend to say they do.
(, Thu 15 Mar 2007, 19:07, Reply)
If I put on a dress, I look like a dyke in a dress...



But if I work at it, I can pull it off... (the lesbian wearing a dress thing, not the dress itself)
(, Thu 15 Mar 2007, 19:05, Reply)

Putting clothes on always makes me angry.

I'm the crossest dresser I know.

Boom! Boom!
(, Thu 15 Mar 2007, 18:58, Reply)
The last time
that I cross dressed was for 'pink day' at college, most people had brought something pink to wear but me being me I only looked in one shop for a pink feather boa and could only find red or black so I didn't bother. So one of my female friends put a pink hair clip of hers in my hair, which is quite long. I was on my way to a lesson that day when I walked past some guys and I swear one of them said "is that a girl?". That was the easiest cross dressing I've ever done. At work I get mistaken for a girl every so often, it's pretty funny.

Best time was last weekend when a child asked his mother "What's that man doing?" and she snapped "How do you know that's a man?" at him. Shows who's the most intelligent there.
(, Thu 15 Mar 2007, 18:47, Reply)
Not once, but twice!
Have I been mistaken for a girl. Both times at work.

The first I was up the ladders, moving stock about when a young mum and her pain-in-the-arse toddler sauntered over. After a few minutes of idle childish chit chat I heard the mum say to her little girl, "Go on, ask the woman where #### is kept." I spun around and told them where the product they were looking for was kept. The mum went beetroot red, made her excuses and then dashed out of the aisle in the complete wrong direction.

Second time I was walking along the shop floor killing time when I heard a raspy Geordie voice say "Scuse me love?" I turned around to see a big, butch fella with a shocked look on his face. He apologised profusely and buggered off without asking me anything.

Length? Well, truth be told my hair wasn't even that long.
(, Thu 15 Mar 2007, 18:46, Reply)
Unfortunately, I managed to get a reputation during my first two terms at Uni as some sort of pervert. I've only done it twice, but admittedly, it wasn't exactly compulsory at the time. The most recent time was a "P" party. I came as a policewoman. This gave me the opportunity to go around berating/sodomising people with my truncheon, and handcuffing them to each other. By the end of the night, there was a condom on the truncheon, which lead to this wonderful picture of my friend.

I'll be honest, that story was true, but largely an excuse to include that photo.

Anyway, the first "incident" was when at a school uniform theme. I was pressganged (honest) into going as a schoolgirl. Unfortunately, having completed the short and mildly humiliating walk to the venue, I found out that, unaccustomed to wearing a skirt, I had forgotten my ticket. "Woe is me" I cried, and asked who would walk back with me to get my ticket. My friend volunteered, and as we walked back, I started running. He started running behind me. So now there's a 6 foot 4 schoolboy chasing a 6 foot 2 schoolgirl through the streets, with the schoolgirl deciding yell "Ohh don't chase me! Oooh!" and other such girly exclamations.

Oh, and a gay guy bought me a drink. I think it was a fairly good night all told.
(, Thu 15 Mar 2007, 18:30, Reply)
My NHS computer records say I'm male.
several letters and calls later...

It *still* says I'm male. Despite numerous appointments prescribing me the contracpetive pill, gynecological referals...

I may need to quiz my parents one day.
(, Thu 15 Mar 2007, 17:44, Reply)
my drag names, should I ever have occasion to use them.

Monique Depressive

Cyn Willingly

Cassandra Complex

Constance Craving.
(, Thu 15 Mar 2007, 17:44, Reply)
Alright son..
Not quite the same, but when I was 14 at a slayer gig I fell sideways in the mosh bit, and some bloke caught me. Patted me on the head and said "alright son?" Gutted.
...used to dress one of my my brothers up in my communion dress. He later blamed me for turning him into the flamboyant young man that that he is today..used to put makeup and a kilt on the other brother. Didnt have the same effect. He stays in his room mostly.
(, Thu 15 Mar 2007, 17:44, Reply)
I'll post some stories tomomrrow now as, well, I can't be arsed just now...

But, I can scarily pass myself off as a woman - Without trying. It's my smooth, soft skin, good legs, nice ass and the fact that I can walk like a woman.

I'm actually not joking. As I've been told this.

And no, I'm not gay, transexual or into anything odder than hetero.

Being told, however, by a large, scary-ass Steel worker who'd locked me in a room with him that I was "pretty" and "shouldn't end up in prison" really, really, doesn't count. shudder - Thank feck for mobile phones is all I have to say.

No, there was not (and never has been) any violation of me
(, Thu 15 Mar 2007, 17:43, Reply)
I don't tell that many people that I am actually a transvestite
Although most of my mates know now.

But if I get a legitimate excuse, try stopping me. Went to a fancy dress dressed as Agent Scully, and got amazingly drunk. On the way back to pick up some stuff from my car before jumping in a taxi, two guys were walking towards me. One of them wolf-whistled. I think they're taking the piss, and say "thanks guys" in my normal blokish voice, to which he replies, shocked "is that a bloke?!" I laughed and laughed.

And to Fothermocker and any other doubters, I've been told by many many people (of both sexes) that I look great. The only reason I don't do it more often is that I'm scared of being killed with sticks.
(, Thu 15 Mar 2007, 17:29, Reply)
I'm having nun of it.
At my 6th form, we were having a dress up day, all the usual sorts in like doctors nurses/sluts etc.
Previously i had bought A sexy nun outfit one size fits all (but not 6ftish well built men) which due to my unfeminine body just stretched over my package. Coupled with fishnets, I was sexy nunness personified.
With the help of my costume me and two friends won battle of the bands (singing its raining men) flaunt what you have!

Wore the outfit twice more before it got ripped, first was at a party, drunken tore my fishnets. Third time I was a slave at school for my psychology teacher. Went into town for midmorning snacks (saw how lazy it was being a teacher :p). However lunchtime was another story; same short skirt style, standing in a hall full of uniformed idiots. The girls grabbed my arse, nearly tearing my fishnets bitches! And the guys tried to look up my skirt THEN call me gay, haha.

I actually still am called Ian the Nun in that town :d (Even my a random kid who i'd never seen and went to a primary school)
(, Thu 15 Mar 2007, 17:24, Reply)
Girl for day (come on - it was inevitable)
A few years ago, I was in the improbable position of actually being a girl for one day. What could I do with this unique opportunity? Attempt to fully understand the female psyche? Make men understand both sides? Stay in bed and play with my tits all day? No - I decided to go out, get trashed and be a slut.

I should add that I really was girl, with all the biological parts. And what wonderful parts they were, too. Large, firm breasts that stood alone and required no bra; a pert arse that swelled provocatively and just cried out for doggy, and - I admit it - a good, tight snatch that could have peeled a banana if I'd wanted it to.

What to wear, what to wear? I tried to think what men like, and decided not to be subtle. So - miniskirt, self-supporting black stockings, a miniscule g-string and a skintight top that barely held my tits in. I got my sister to make me up, a bit heavy on the eyes and something semi-slutty for my lips. I should point out that as part of this highly unlikey transformation, I had actually developed a yearning for cock. Not just a yearning - more of a consuming desire.

The first pub we hit, I felt what it's like to be devoured by men's eyes the way I had always looked at women. I could virtually feel them undressing me. My nipples perked up (which caused more attention) and I fel my newly-acquired clitoris flaring up in those see-through pants. And I realised I didn't have to do a thing. Just stand there and look pretty and wait. No need to play cool or coy - I'd be a man again the next day.

A guy walks up to me. He's handsome, but a total tosser and obviously a hit with a certain kind of girl. Never mind. "Let's forget the chat-up," I said to him. "Shall we just fuck?"

His was was a mask of amazement, but I took him by the hand and led him to the ladies, where I dragged him into a cubicle and levered his cock out of his jeans. It swelled in my hands and I helped it along by swallowing it. The sense of power over the guy was phenomenal. He should have been on HIS knees. In fact ... "On your knees!" I instructed, I sat on the toilet and he ripped my panties clean off before applying an electric tongue to my drenched hole. I can tell you, the sensation was something special and put me in the mood for a vigorous shafting.

So I stood up, turned around and bared my delectable arse at him. He soon got the message. The feeling as he pushed his considerable tool into my sweet, tight snatch was unbelievable. Each thrust was a shudder of ecstasy up my spine and I reached down to grab his balls as he pumped me relentlessly. Just as sounded like he was going to come, I slipped off his cock and took the glistening rod deep in my throat to feel the hot jizz gushing down in salty spurts.

But I hadn't yet come. "Have you got any mates? Go and get them!" I demanded, looking at my watch. In no time I had a mouthful of cock and another in my ass. I came like a hurricane and left the club with jizz in my hair and my 'reputation' ruined. Time well spent, in retrospect.
(, Thu 15 Mar 2007, 17:19, Reply)
i knew a guy who cross dressed
his name was jesus.
(, Thu 15 Mar 2007, 17:19, Reply)
Music Soc at Uni had a number of themed parties through out the year. Best of all was the annual end of term beachwear party.

Happened the last Wednesday of summer term starting at 7:30pm prompt in the Old Bar, then onto the Poly Bop followed by massive house party off Victoria Road (10 out of 10 if you've guessed the city).

James (because that was his name) was convinced that it all started at 6:30pm (and why not?)

So 100 or so undergrads arrive in assorted Hawaiian Shirts, Wetsuits and Snorkels at 7:30pm to find James sat alone on a barstool at the bar - which at the time was the largest bar in Europe. He was on his 3rd pint, staring intensely at the bottom of his glass, dressed only in a borrowed fetching skin tight pastel blue one-piece female bathing costume and a flowered swimming cap.

He said later that it was the longest hour of his life.
(, Thu 15 Mar 2007, 17:18, Reply)
Well, it's kinda cross-dressing...
Not me, though- my girlfriend. You see, she has rather long legs and a small butt, so her jeans are about the same size as mine. (I wear Levis, 36 waist and 34 length.) So there have been a few times when we've gone out to the store or to do yardwork and she's found her pants falling down- because they were mine.

Conversely I was struggling to get into a pair of jeans one day, cursing my fat ass, when I discovered that they were size 12...

Does it count that she wears my bathrobe and I sometimes wear her tee shirts?
(, Thu 15 Mar 2007, 17:16, Reply)
ooooh, it's been a while...
An ex of mine was at Sheffield Uni while I was down in London. I used to visit a lot (obviously) and at one point everyone thought it would be a good idea to put a band together for the student band competition. I pitched in, and on the night of the gig thought it would be a good idea if I turned up in one of her little summer dresses over a shiny leopard-print top (albeit with jeans underneath...it was cold!) and eyeliner (although that was usual for me at the time...and I always looked fit in it). We turned up at the union and I started to explain that I wasn't actually a student when the bouncer just said "it's alright mate, you're obviously in one of the bands"



We lost the competition, but I did get to flounce around all night in a dress without being hassled. In fact, for all the years that I used to wear eyeliner, skinny Ts, hairslides and plastic kiddie jewellery I never once got hassled about it...nothing to fear but fear itself.
(, Thu 15 Mar 2007, 17:03, Reply)
Sort of Hijack....
In response to Bulldog Ugly 'you'll never have more of a laff.'

Please take in to consideration i have seen a blind man walk into a lamp post. Actually properly walk into it, arms either side. i felt like i was going straight to hell for laughing so much. He was okay though, so no worries.

On the subject, I was pretty 'famous' in our household for wearing my mums shoes (im a chap) and lippy and all that gubbins. I must add that this was as a youngster, im not still doing it now..... honest.

Anyway, so i used to dress up in this garb, but some twunt once got a photo. That does the rounds when the laydeez pop in to meet the family - 'look at him, in those heels, what was he thinking.' I think that is the ONLY photo of me as a child that makes me cringe.
(, Thu 15 Mar 2007, 16:57, Reply)

This question is now closed.

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