You are not logged in. Login or Signup
Home » Question of the Week » Cross Dressing » Page 1 | Search
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)
Pages: Latest, 12, 11, 10, 9, 8, ... 4, 3, 2, 1

This question is now closed.

School girl bash
Went out for my 21st dressed as school girls, so convincing was i that i had other men going for the muff grab all night to "double check".
Ended up having to snog a fat chick who thought i was a lesbian just to get some peace, and there ain't no need for that!
(, Thu 15 Mar 2007, 16:44, Reply)
Our School 'Non Uniform Day'
We often use to have non uniform days at ours school, but you had to give 1 to charity for the privilage. The one I'll always remember is when a guy came in dressed as a woman, wig and everything, the teachers sent him home!
(, Thu 15 Mar 2007, 16:28, Reply)
To be serious for a second
Although I grew up in a pretty conservative family, my open-mindedness have exposed my immediate family to some of the more colorfull elements of society, and they freely admit that they are better people for it.

I can't stand folk who seriously knock something without any bloody knowledge on it, diversity is fun and keeps stuff intersting.

Try it, just once do something you aint supposed to by standard conventions, you'll never have more of a laff.
(, Thu 15 Mar 2007, 16:26, Reply)
Women's problems
This is sort of related. When I was 14 I was stopped in Guildford High Street by one of those people with clipboards.
She asked me "from the below, please indicate your preferred brand of sanitary towel?"
We looked at each other blankly, before she realised with horror that I wasn't a girl. I still got a free sample though.
(, Thu 15 Mar 2007, 16:20, Reply)
Seems you're not alone
I pulled my Ex by wearing her prom dress for her.
I did get head in exchange though even if I had to wait 18 months for it
(, Thu 15 Mar 2007, 16:19, Reply)
Cross Dresser
I'm mightily annoyed...

I sit in your bedroom all day long and all you do is put clothes in me all day - There's just no respect, you open my draws and thrust your grubby mitts in them.

Have you no respect???

Yours:

A Cross Dresser


/drainpipe
(, Thu 15 Mar 2007, 16:17, Reply)
An unusually serious answer for once
Among other things I have the remarkably rare talent of being able to convincingly pass myself off as a woman; the only things which really give the game away (besides the blindingly obvious one) are the fact that I'm exceptionally tall, and I have a gravelly Yorkshire-accented voice. I've been pursuing this activity for a number of years now, and have recently got good at it. Maybe I could put it to good use, and use it to advance my career.

Few if any people know about this talent, as it's obviously not something I want to broadcast, and I intimidate people enough as it is.
However, if you really want pictures, feel free to GAZ me for them.

[Edit] what makes it even more remarkable is that I'm normally not in the slightest bit effeminate or androgynous.
(, Thu 15 Mar 2007, 16:15, Reply)
but seriously
I always used to put my sisters clothes on when I was ickle.

mainly cos it annoyed her, but also because I wanted to feel 'free' down there.

that reads a lot worse than It sounded in my head.

EDIT 'best' page 2 weeks running! it aint gonna be 3 :-(
(, Thu 15 Mar 2007, 16:13, Reply)
deliberately misread
i got up, and tried to put on my jeans.
managed to get both legs in the same hole 3 times.

then i pulled my head through the arm hole of my jumper.

it really annoyed me, and I was definately a 'cross dresser' that day.
(, Thu 15 Mar 2007, 16:11, Reply)
Bloke in a dress - yes please !
I'm the same as ancrenne

Eddie Izzard is bottom pinchingly lush.
Guys in frocks rock.

It has to be a straight or bi guy in a frock. It's the juxtaposition of masculinity and femininity all in one package - I also like butch women because of this.

In my last job I sometimes used to wear a tie, waistcoat and trousers and the guys loved it.
(, Thu 15 Mar 2007, 16:10, Reply)
Mmm, silky
Housesitting for my father, I once spilled something on my boyfriend's jeans. Unfortunately I didn't have many clothes with me, and my dad's pretty fat. So my boyfriend had to wear my calf-length silver silk skirt until his jeans had dried. Made going out for a cigarette mighty uncomfortable, what with it being October and my dad living on a cul de sac.
(, Thu 15 Mar 2007, 16:02, Reply)
It was an accident - Honest
It was after a long night of drinking, smoking and general drug taking that led to me needing a pee @ about 5am sooooooooooooo managed to shift out of bed and as we had guests, needed to throw on something to cover my cock and so grabbed some denim from the floor and popped it on.

Yep, it was the missus skirt - thank fuck no-one saw me!! (apart from the missus who sitll won't let me forget it).

Oh, and I wore her bra and panties for a sex game, but thats another QOTW.

H i Elaine!!!
(, Thu 15 Mar 2007, 15:59, Reply)
*shrug*
A female friend once accounced "You aint lived till you've been out on the lash in a leather mini skirt wi' nowt underneath"....

Ladies, Gents, Fellow B3tans.... following one of my locals accouncing a 'ladies night' involving cheap beer, I can tell you, I've lived!

(am a 6' 14stone bloke for those who managed to avoid the possibly horrific imagery)

Other BDU-flavour examples of my total lack of shame include:

Attending a gay club with some of my 'that way' mates in same leather mini skirt (which yes, i bought especially) and dubbing myself "Mr Money Shot" for the night.

Trying on a leapord print Thong in Tesco and chasing Mrs BDU round the clothing section in it.

and...

Deciding I would pad a bra for the night and wear it in an effort to get served quicker (worked a treat).

I have no shame.
(, Thu 15 Mar 2007, 15:55, Reply)
Pyjama Party
.
UMIST, in Manchester, used to hold a Pyjama Party every year in February and I used to go. My favorite outfit was a lime-green nightie which I fetchingly accessorised with Doc Martin boots and a leather biker jacket.

One year I trapped off with a wee little blonde lass, and being students, we ended up hitch-hiking across Manchester to Collyhurst (really rough, dodgy, area) at 3am in the morning wearing only nighties. That was a bit silly. But not as silly as getting the bus back to mine the next day wearing the same gear during rush hour.

Cheers
(, Thu 15 Mar 2007, 15:52, Reply)
Call me conservative, but
I think men who dress up as women for reasons other than humour are a bit mentally ill. Nothing wrong with being gay, but a man dressed as a woman is like putting lipstick on a dog. Men - apart from Asians, maybe - ALWAYS look shit as women: lumpy legs, big noses, stubble, gangling walk, big shoulders. For a man to dress as a woman is to insult women rather than praising them by emulation.

I used to live in Brighton - which must have a higher than average amount of cross-dressers - and I saw a guy there who was a perfect case in point. About 6'2", an adam's apple like he'd swallowed an anvil and a face like Richard Ashcroft. He looked like a shaved Honey Monster. And yet he had this thin, curly hair, rouge, lipstick and a dainty floral dress and heels.

Live and let live - yes - but he looked like a feckin' tosspot as a woman. As a guy, I'm sure he looked fine. If you admire women, leave it to them to dress like one.
(, Thu 15 Mar 2007, 15:52, Reply)
Cross dressing is bad mmmmmmmmmkay
After a nite of consuming certain class A pills i awoke from my slumber on my friends kelly's settee covered by a comfy blanket.

My mate Craig come through into the living room and the conversation goes like this:

Me: urgh

Craig: Morning girly

M: Girly? WTF?

C: Look what ur wearing!

I removed comfy blanket to reveal a rather fetching pair of ladies knee high boots and kells best little black dress.

IMO i didnt look to bad.
Length... Knee high baby.
(, Thu 15 Mar 2007, 15:50, Reply)
pants
I once tossed into a handful of my sister's pants. She was livid when she woke up.
(, Thu 15 Mar 2007, 15:38, Reply)
At last!
My younger brother is 'artistic'

As you may or may not care my career is in the motor industry - still a pretty masculine kind of environment.

The garage I'm working in at the time has an MOT viewing window at which there is a group of 10 or so mechanics shouting 'there's a bloke in a dress.....a bloke in a dress!'.

And there he sits. Dress on. Made up. Bastard.

That said - it's Rocky Horror in Leeds next week....try stopping me!
(, Thu 15 Mar 2007, 15:36, Reply)
Pyjama Jump
Does anyone remember the Sheffield Pyjama Jumps of yesteryear?

Thousands of students, shit faced dressed either in pyjamas or clothes of the opposite sex...

I've a few stories of my own, I just need to dredge them from memory - and suppress the trauma that comes with it. These involve, me, wandering hands and a lecturer (female) - it took me 6 years to live that one down.....

PS, let me know if you went to a pyjama jump and ended up at Roxys :-)
(, Thu 15 Mar 2007, 15:35, Reply)
Self loathing
I'm a pretty liberal girlie, with the open sunny natured sexuality of someone who is attracted as easily to women as men, and probably anything in between - Eddie Izzard in a skirt? Yes please... That man makes me realise why high heels have been deemed sexy for so long.

What I'm really not attracted to is someone who is uncomfortable with their own kinks. So it was no trouble when a ex told me he got off on wearing stockings and suspenders. In fact, it could have been quite fun... Except he had some bizarre self loathing about it, a sort of internalised kink-phobia. I'm not talking your usual sexual self doubt, but a huge dose of fire and brimstone, soul sappingly powerful. His difficulty in enjoying what he so clearly, well, enjoyed, was too much for me, so I ended it. It was a real shame. Regardless of gender, am I alone in being almost completely powerless in the presence of a nylon clad leg*?

*preferably accompanied by another one, and the rest of the body. Not just a leg. That would be WIERD.
(, Thu 15 Mar 2007, 15:34, Reply)
I hate my friends
me + holloween party + lots of alcohoul + tutu = pictures
they have been burned, and the memory drives they existed on thrown into the fires of Mount Doom.
To this day I have no idea how I was convinced to do this.
(, Thu 15 Mar 2007, 15:32, Reply)
Cross Dressing = Poverty
Working for British Gas is very boring
Bubbly People (aka 'ADD') have low boredom threshholds
Thus: www.vacant-cs.pwp.blueyonder.co.uk/1142295716.JPG
I got sacked
It made me poor and hungry :( with the silver lining that the extreme hunger meant i could fit into smaller and sexier skirts :D

huzaah! /semi-pea
(, Thu 15 Mar 2007, 15:31, Reply)
Devils In Skirts
.
Being from Northumberland I attend weddings wearing a kilt. And yes, I do wear the kilt the way it's meant to be worn, tackle-out.

It's a strangely liberating experience. Surrounded by hundreds of people when I'm wearing a skirt. But the best thing is, if anyone gives you any hassle then you whip out your sgian dubh and start picking your teeth with it. They soon go away...

Cheers

It's a fucking knife that you keep in your sock you filthy-minded bastards
(, Thu 15 Mar 2007, 15:24, Reply)
Forced Transvestism
Not a long one, got very drunk before a night out, ended up with Mascara, eye shadow and blusher on my face, glitter all over my body and my usual long straight hair curled using curling tongs.
It was the only time I've looked like a cross between Nicky Wire and Eddie Izzard.
(, Thu 15 Mar 2007, 15:16, Reply)
boy george
i am a girl. i went to a fund-raising uni cross dressing party as boy george. i did it rather too well.

no, i'm not going to show you the photos.
(, Thu 15 Mar 2007, 15:16, Reply)
B3stards!!!!
gotta check then be right back!

Edited: I don't believe it, go for a quick fag and they change the question of the week, at least I finally got the last response on the previous question [blows raspberry]

What....? something relevant to this question other than just trying to get first so the powers that be don't remove this post... errr...

I did once wear a kilt to my brother's wedding, and you know what, it felt strangely liberating to be wearing a skirt and feeling the cool fresh air around the gonads.

So much so that I was hoping the missus would put on a strap on and bend me over a table to let me know just how liberating wearing a skirt could be!

She never did, we're separated now! The bitch!
(, Thu 15 Mar 2007, 15:14, Reply)
Gurilla
Dreesed up as an army type lad, complete with drawn on khol beard and porno in me pocket.

i looked EXACTLY like my dad, except my name's Sarah, so not wonderful really.

Edit: BUGGER!!
(, Thu 15 Mar 2007, 15:12, Reply)
I like Cross dressing
Trousers are ace.

Edit : YAY I WIN!
(, Thu 15 Mar 2007, 15:12, Reply)

This question is now closed.

Pages: Latest, 12, 11, 10, 9, 8, ... 4, 3, 2, 1