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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.

I'll wear yours if you wear mine
Many moons ago I was away in Newcastle with work. My 2 colleages and I, lovely ladies the three of us, went out heavily drinking and partying on the thursday night, the last night of our week away.

Not being local, we didn't know where to drink or club, so started off in a random bar and asked around about where was good/cheap. It turned out that there was a massive student pub crawl on that night, with all the local unis taking part. They had paid for the privilege, and were all wearing special t-shirts. They got a free drink in every pub on the list, free entry to a club at the end, and a free bar when they reached the club.

Well, we decided we'd join in. One problem - we didn't have the t-shirts. We made it our mission to get a t-shirt if it was the last thing we did.

Well, after tracking round a few pubs, we caught up with the crawl. Blagged our way into the club for free (getting the goodie bag too) and continued on our quest.

The married member of our team was reluctant at first, but soon got into the swing of things, playing tonsil tennis with a poor wee student and trying to rip the shirt off his back without him noticing. Nearly worked, she had both arms out of the holes, just couldn't unlock the lips long enough to get it over his head.

My tactic was more direct. I was wearing a little red top which clearly had no bra underneath (being fairly perky I didn't need one). I was chatting up one guy trying to get his t-shirt, which unsurprisingly he was loath to part with (it's his ticket to a free bar, remember). I ended up offering to swap tops with him. Yes, in the middle of the club I would take off my top and give it to him if he gave me his first.

He fell for it, and whipped off the sought-after t, passing it to me in the hope of seeing some bouncy breasts [1]

I put on his t-shirt, did the wriggle we girls can do, took the top off under the t-shirt and gave it to him.

He was less than amused.

Even less amused when I grabbed my top back (from River island, I wasn't letting him keep it!) and ran off to the ladies still wearing his free bar ticket.

I got changed again, and in my soft-heartedness gave him back his t. I even gave him a flash of the breasts he'd been ogling. So he bought me free drinks all night.

Happy ending all round :o)

F x

[1] sorry, this almost turned into a Frankspencer-esque tale :)

PS: the third member of our saucy trio? We lost her towards the end, she turned up for work the next day looking shattered, claiming she'd won because she'd slept in one of the t-shirts. Fair play to her :o)
(, Fri 16 Mar 2007, 12:23, Reply)
Aston Uni Ball
Once went to a ball at Aston Uni with an ex of mine, he dressed as a french maid and I as a pirate. I must say, I really looked the part, clip on parrot on shoulder, great big biker boots and blue/white striped jeans rolled up to the knee and leather waistcoat.

After one to many, I get into the swing of things and swagger up to the bar, when over the tunes of One Step Beyond (Madness cover band) I catch someone say to me "Hello Sarah!" Not living in Brum or knowing anyone else there I defensively reply "how do you know my name?".
Transpires the guy was saying hello Sailor...was muchos embarassed.
(, Fri 16 Mar 2007, 12:22, Reply)
I cross-dressed for ten years starting in the late 1960s

and no one noticed.

(, Fri 16 Mar 2007, 12:19, Reply)
Leeds Fest 2006
Me and all my mates cross dressed. It was a right laugh. We all crowd surfed when Maiden came on.

Apparantley I looked like a skinnier, more lesbianish version of Jo Brand. Thanks alot for that comment Craig.
(, Fri 16 Mar 2007, 12:19, Reply)
Jolly Hockey Sticks
Not really my game, but got roped into playing hockey for the office team a couple of years back...apparently they were short a goalie.

Being a cricketing type in the summer, i know the damage a hard ball can do to two softer ones, so i made sure to dig out my box (cup for you merkins) to protect the existence of future progeny. This obviously required a jockstrap as well, but it became clear that mine had not been washed since the end of the cricket season 6 months ago. I may have put my cods in something smelling worse in my time, but not whilst sober, so i had to seek an alternative.

Now i am of the boxer wearing persuasion, as briefs are for woofters and Y fronts are for fat dads, so i had nothing to hold the boys in place. In a flash of inspiration i thought i'd check out the undie drawer of the gf at the time. I believe girls often refer to these as "period pants" - sturdy, unfashionable, but there to do a job. Ideal for me - a bit tight, but kept everything in order, and under trackie bums, who would ever know. Splendid. Job Done.

Alas, as i say, hockey is not my game, and hampered by the huge amount of padding i was forced to wear, i was about as manouverable as Thora Hird. First bit of action, i trip over my own leg, stumble, and land flat on my back on top of the ball. Absolute agony.

Yes, you've guessed it. Hospital. Suspected coccix damage. X-Ray. Remove trousers. Ha ha, you're not going to believe this but...

Clearly i had girls pants on. Obviously my workmates present had the good grace to treat me sympathetically and not tell other colleagues etc*

*May not be true

Length? It was a big box. More of a crate really.
(, Fri 16 Mar 2007, 12:18, Reply)
i've crossed dressed a few times
i have to say, men are fucking stupid!!!
i now know what you women go through!
(, Fri 16 Mar 2007, 12:01, Reply)
Drag Ball
The only time I have cross dressed is for an annual Drag Ball at one of my local pubs. Not one for doing things by halves I went all out glam, glitz and attitude. The sheer pink sequin dress came down to my ankles, white gloves to my elbows and the pink wig nearly touched the ceiling. I even suffered pit shaving (and plucking all three hairs out of my chest) to get the image right. Needless to say, I had to have a *couple* of drinks while gettnig ready, and a hell of a lot more during the evening.

To round it off we went to a gay club around the corner. All the drinking was starting to get to my bladder so after a bit of consideration I head off the to Lady's. I was met by several militant lesbians who gave me evils and told me to fuck off to the Gent's. Unfortunately the Gent's was upstairs - yes I did trip over the dress / heels. When I got in there were loads of blokes waiting for cubicles and milling about so I decided to use the urinal. This involve hitching the skirt up over my waist and pulling down tights. I could hardly stand up and definitely looked a right sight!

Here's the pictures:
(, Fri 16 Mar 2007, 11:50, Reply)
well said sir.

also, I dressed up as a schoolgirl once for a theme night in the pub I was runnig at the time.

And you definately would of.
everyone of you.
(, Fri 16 Mar 2007, 11:49, Reply)
Shop assistant guffaws
During my college years I had a Saturday McJob at a well known chain of newsagents. This job was as exciting as it sounds.

After three years of selling newspapers and A4 ruled pads which save for a couple of dates with one of the lasses there was the most exciting occurence there I was sat at my till on my penultimate shift prior to shipping off to uni.

It was quiet so I was people watching. My eyes were drawn to a somewhat gangly figure browsing the magazines. "Fuck me, she's tall" thought I. Then "she" got closer.

This cross-dresser had gone to huge efforts to look good, with an expensive black dress and a black choker worn around the neck to disguise the Adam's Apple. Hair had also been expensively done by the look of it and makeup had been carefully applied. However, the look was ruined by two hugely obvious things; firstly black heels in a size ten are a giveaway and secondly the day's growth of stubble didn't help either.

I mean, if you're going to the trouble of wearing a choker to disguise the bulge in your throat, but think "shall I shave? Nah, fuck it" then you deserve all the ridicule you get.

If you really, really have to go to great lengths to look all pretty and get in touch with your feminine side it should be remembered that no amount of carefully applied camouflage is going to disguise the fact that you're a hairy, bollock-scratching geezer. Heels are not designed to be worn by anyone who possesses testicles, fact.
(, Fri 16 Mar 2007, 11:49, Reply)
Aussie Rules...
On recollection I think that Aussie Rules football kit is slightly feminine...

Tight brightly coloured stripey vests?
Hot pants?
Knee highs?

Google "Wariwck Capper" if you want to see a particularly attractive example.
(, Fri 16 Mar 2007, 11:45, Reply)
The clothes making you angry joke

Leave it now.

I've worn women's clothes. This post is now on topic. Thank you.
(, Fri 16 Mar 2007, 11:43, Reply)
That's a girls thing
Back in school we'd do a little play, and as I turned out to be an awful actor, my job was to position the microphones, getting the lights and audio settings done etc.
On the evening of the show one girl who was to play one of the main characters refused to go on stage in such slutty garments. As i seemed to be the only one who knew all the text of the play i had to jump in. Somehow protesting the slutty outfit didn´t work for me... i probably could have given more resistance, though.
I even had to go on Stage in the knickers of some other girl, as my boxer shorts were coming out underneath the skirt. It felt weird to do this for the first time in front of my parents, and all my friends' parents, but ever since i moved a couple of hundred miles away from home, i have no problem with it anymore.
(, Fri 16 Mar 2007, 11:31, Reply)
etiquette is important...
For the celebrations revolving around my 21st birthday I decided to have a 60's party. No other reason than I had procured a nude suit and a Hugh Heffner costume and had convinved numerous women to come dressed as my bunnies.

Anyway, one friend, a 6ft 4' lanky architect, decided to come as a bopper type woman. Loud colours, bobbed blonde wig, make up, the whole bit. He looked fantastic and was a hit with my token gay friends.

Anyway, his costume fell down at the shoes. They were entirely appropriate, but he couldn't find any heels that were fitting his massive, manly clodhopppers. So his size 11 feet were crammed to bursting into some size 6, or so, white kitten heels. Chunks of his feet were literally spilling over the sides and it was by all acounts very very painful.

So he was chatting to one of my girly friends at some point and was complaining about his sore feet. My lady friend informed him that in polite society it was acceptable for women to remove their heels after midnight.

Amazed, my friend hopefully checks his watch.

"Sh*t... it's still twenty minutes to". And proceeds to waddle around wincing for the next 20 minutes so as to successfully fulfil the etiquette imposed requirements forced on all women of certain standing.

What dedication!

My own cross dressing story takes place very early in my life when I convinced my Grade 3 class (about 8 y.o. I think) to perform Robert Palmer's, Simply Irresistable for the Christmas concert (I don't know. Don't ask). And we got the girls all in 80's suits and the boys all dragged up in miniskirts with tennis balls down their halter tops, gyrating around oversized pencils in front of their parents and the entire school community.

I'm amazed I'm not more messed up. Especially since there is a lot of photo and video evidence to remind me, my family, friends, girlfriends, family friends, family friends girlfriends, nieces, nephews, passersby, of the auspicious occasion.

Length: I was 8, but it still had to be squished firmly between my legs to avoid the disctubring bulge in my miniskirt.
(, Fri 16 Mar 2007, 11:29, Reply)
the trousers
i have on today are a pain cos they are to small and everytime i sit down it tightens round the crotch which is annoying me , the shoes i have on also have caused me a blister and everytime i walk it hurts which also is annoying me and the the shirt i have on the collar is to tight which is causing discomfort and really pissing me off aswell, which is when i realised today i am a cross dresser...
(, Fri 16 Mar 2007, 11:20, Reply)
I have
been reliably informed that if I were ever to don a frock I would be the spitting image of Les Dawson.

(, Fri 16 Mar 2007, 11:01, Reply)
Miss HYM
My youth orchestra went on an annual tour. There was a tradition that on the last day, after we’d packed and cleared out of our hotel rooms and had a few hours to kill before departure, we would stage a tournament.

Miss HYM

Boys would be nominated to participate. They would of course resist but by the end of the week, would have been successfully cajoled, coerced or blackmailed into it. Each boy would be assigned a “dresser” – a girl who was responsible for making him look as ravishing as possible. Hair would be coiffed, make-up would be applied, legs would be shaved, bikini lines would be waxed, gargantuan quantities of alcohol would be imbibed.

The end result looked like this:


This was seven years ago and that guy on the right STILL has my sparkly pink hair slide!
(, Fri 16 Mar 2007, 10:56, Reply)
"Tranny or Granny" last week

QOTW on Crossdressing this week.

Is our Ginger Fuhrer trying to tell us something? Is s/he?

Back on topic: Taking part in a school assembly on the Ancient Egyptians, clad only in a girls' gym skirt = years of confusion. Damn you, primary school teachers!
(, Fri 16 Mar 2007, 10:50, Reply)
First week at Uni
It was that usual Soc Mart thing where you sign up to societies in a desperate attempt to make friends and integrate, only to never again attend the Society you chose because it's full of wankers you hate. But as I was walking around between the various stalls, I wandered into a room with a few people sitting around.

I cast my eyes about and soon got the message. It was a bunch blokes in drag. One of them looked hilarious - a big-boned guy who was probably in the rugby team. His make-up barely covered his stubble and no amount of haircare products had affected the straw-like texture of his hair. Another was a lanky, bony bloke with goggly eyes and big veiny hands. You'd never mistake him for a woman!

"Great! A Cross-Dressing Society! Sign me up!" I said.

The temperature dropped about ten degrees and the rugby bloke pointed wordlessly to a sign on the door behind me: "Feminist Society." They were not men.

So I joined the Cannabis Society and the zany Society Society, never again to attend.
(, Fri 16 Mar 2007, 10:47, Reply)
Mr Money Shot
I've had guns put in my face, the cold blade of a kitchen knife pressed up against my scrotum by an ex, and threatened by half of the rough looking bikers in Yorkshire due to my missus been one o' their daughters, but I have never known fear like been in a gay club, as a straight man in a leather mini skirt with nowt underneath.

one of the conversations went like this:

Me: I'm flattered fella, but i like holes, not poles.
Gay Fella: I have a hole
Me: Errr...
Gay: Giving it doesn't make you gay
Other Gay lad: No, liking it does.
Me: ...errr... whose round is it.
Gay Fella: You would enjoy it
Me: Aye, but my mam warned me about folk like you,
Gay Fella: (laughing) what did she say?
Me: She said "Watch out for them puffs, they will want to bum you".

Strangely, I never wore the skirt again

I do have a nice arse though apparently
(, Fri 16 Mar 2007, 10:40, Reply)
There are indeed a lack of women posters - but I do know women with facial hair...

(, Fri 16 Mar 2007, 10:34, Reply)
It was always when drunk....
It always seemed funny at the time...
Friends always got photo's....
Friends always bring out photo's to remind me at embarrassing times like when I have a new girlfriend.....
It always say I was just drunk and they dared me...
They always deny it
I think I looked quite good in the basque!
oh the shame, the shame.
(, Fri 16 Mar 2007, 10:32, Reply)
I'm curious
There are plenty of stories here about men dressing up as women, either for comic effect or sexual kicks ... but I'm wondering about the girls. Of course, they can wear 'men's' clothes all the time without breaking any taboos or raising any eyebrows.

Are there any girls wearing rubber cocks in their pants or sticking fake facial hair on? And if they're not, how does that affect our perspective of men who stuff bras? I've got no answers - I'm just curious.
(, Fri 16 Mar 2007, 10:25, Reply)
Bit of advice
When a visiting a foreign city, New York for example, one may encounter “a female impersonator” when out for a bout of drinking a the "boozer" or "pub". You should "test" her femininity with a quick feel of the crotch. Be warned though, it might be an actual woman with a very low voice.

Michael J. "Crocodile" Dundee
(, Fri 16 Mar 2007, 10:21, Reply)
Only once in my life...
...have I worn women's clothing. It was about 1979 I think (or whenever the International Year of the Child was, for those of you old enough to remember that), and I was appearing in a local concert thingy in aid of said charity year. I and two of my mates from the Boys' Brigade were doing a sketch, dressed as women.

So there I was sitting on stage, eye level to the audience, wearing a skirt. Sitting on the seat like a bloke. Legs apart. Thankfully I had my Y-fronts on. Probably orange and brown ones, seeing it was the 1970s.

Apparently a lot of the audience got quite a laugh, and not because the sketch was funny.

At least in the intervening years, since I've become older and occasionally wear the kilt at weddings etc, I've become more aware of how one should sit while wearing a skirt so as not to display one's bits. I'm now quite good at not showing my willy in public. Unless I'm doing it deliberately.

Length? Pretty short - I was only a kid.
(, Fri 16 Mar 2007, 10:17, Reply)
Oh dear...
I've got SUCH a good story from one of my colleauges, but he'd MURDER me if he ever found out I'd posted it on teh interweb. Woe is me...
(, Fri 16 Mar 2007, 10:07, Reply)
Surely man + Thong = NO

I mean, just consider Peter Stringfellow or Rod Stewart.

I think I'm going to be sick now..........
(, Fri 16 Mar 2007, 9:54, Reply)
and loads and loads!
dirty tranny
I'm with sack the chimp on this one, the b3ta tranny army will rise up and destroy you weaklings!
(, Fri 16 Mar 2007, 9:53, Reply)
Going for a thong
I once tried my girlfriends thong on, the back bit shot right up my arse, my bollocks were bulging out the sides and Mr Winki was poking out the top.

I remember thinking, "Well, this isn't very liberating".
(, Fri 16 Mar 2007, 9:46, Reply)
Jeans, Pockets, Heels and Boxers
I really don't like wearing skirts, I feel paranoid that everones looking at me but it still doesn't stop me owning two of them (one knee length denim skirt, and one black, belt length slutty goth one) that I'll wear if I'm feeling confident. i discovered skirts are NOT the best things to wear in hot weather as the top of your legs get clammy (I'm getting shorts this year). My dislike of skirts comes from the fact that as a kid I was a tom boy and ended up showing my knickers in skirts due to my unladylike ways, so I was banned from wearing them (fine by me).

As for pockets, this is a tough one I have an obssession with bags (i buy loads!) but apart from my uni rucksack (my ace quicksilver one I've had for 4 years) I dont seem to use them that often. I really don't like having a bag on me when I got out drinking I get paranoid that in my drunken state I might lose a bag so everything (usually cash, phone and card) go in my pockets. This is unless its a 'girly' night out, which are generally boring.

I cannot walk in heels, again as a child I wasn't to wear my mums heels. I'm getting better I can wear shoes with small heels (5cm or less) but I still prefer my adidas superstar 2 trainers. Although this is good as my feet are not fucked up.

Oh and if I'm at my boyfriends and my thongs are doing my head in (I think every girls knows how uncomfortable thongs are) I nab a pair of my boyfriends pants.
(, Fri 16 Mar 2007, 9:39, Reply)
Ahhhh cross-dressing
Too many occasions to mention and thankfully too few to actually call myself a lady-boy.
(, Fri 16 Mar 2007, 8:56, Reply)

This question is now closed.

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