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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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Never again
When I was on a badly planned 18-30 holiday to Benidorm there was a stag and hen night party. The blokes went on one pub crawl and the girls on another and you met up later that night at the same club, however you could go on the hen night if you were a bloke but you dressed as a girl. Sod it thought I it might be a laugh so I borrowed the goods from the girl in the next room, it turns out she was a bouncy at a club in Moss Side ( scary lass and I can tell you she ate me alive ) and voila there I was short white dress, and black thong, lippy, perfume and whatever you do guys never let a woman near you with eye lash curlers. Never before have I been so shocked! they were drinking me under the table, random women were coming up to me in the street lifting my dress and taking photos of the old fella sometimes behind an unsubstantial thong other times tackle out. The girls were downing drinks, being sick, starting fights and getting off with each other ( which was fine by me ). When we eventually met up with the blokes it turns out they had a shite night. The moral os this is Women are animals when they are out on their own in a group they hunt in packs and are ruthless. It also raised the ulitmate question of where do they keep their money. Remeber white dress and a load of pesatos stuffed in the thong. But it also answered the question of why us fellas always have to buy them drinks.
(, Fri 16 Mar 2007, 8:54, Reply)
I'm a straight non-girly woman
and I really hate skirts. I can do a frock for a couple of hours but skirts, wtf are they about? You have to choose something else to wear with them, and it has to 'go'. That's twice the clothing effort!

So I can't understand why men would want to wear kilts or sarongs. Why wear something that might fall down in public, or otherwise embarrass you?
(, Fri 16 Mar 2007, 8:47, Reply)
I saw a transvestite in a wheelchair at the station. I was somewhat taken aback to say the very least.

Looking back at it, I can't figure out quite why I was, but there you go.
(, Fri 16 Mar 2007, 7:58, Reply)
I humbly apologise for the last 2 posts. Well, I don't really.


I've a real story - it relates to the now ended Sheffield pyjama jumps (see earlier post www.b3ta.com/questions/crossdressing/post74605/)

I was conned (well, it actually didn't take much doing) into wearing a tartan mini skirt, tights, bra and rather a sassy top (God, did I really type sassy) - I was wearing a blonde wig for about an hour, but it was just a little too realistic...

I apologetically admit that it wasn't an entirely unpleasant experience.

Anyhoo - the fun part began when we all got sh*tfaced (it took about 4 minutes as I recall) and I was in my local - O'Hagans just off Division Street for those in the know (Much missed as it was knocked down and is now a block of flats).

I saw a lecturer - I'll omit her name as, well, I just will. So I decided that, well, she must want me to grope her. A lot. shakes head. She took it in the spirit of the night and didn't say/do anything.

Note: I will, shamefacedly, admit that I did hit on her again at a Uni ball (while drunk of course) - something I had to formally apologise for. Took me about 5 years for my mates to let me live that one down....
(, Fri 16 Mar 2007, 7:51, Reply)
I met her in a club down in old soho
Where you drink champagne and it tastes just like cherry-cola
C-o-l-a cola
She walked up to me and she asked me to dance
I asked her her name and in a dark brown voice she said lola
L-o-l-a lola lo-lo-lo-lo lola

Well Im not the worlds most physical guy
But when she squeezed me tight she nearly broke my spine
Oh my lola lo-lo-lo-lo lola
Well Im not dumb but I cant understand
Why she walked like a woman and talked like a man
Oh my lola lo-lo-lo-lo lola lo-lo-lo-lo lola

Well we drank champagne and danced all night
Under electric candlelight
She picked me up and sat me on her knee
And said dear boy wont you come home with me
Well Im not the worlds most passionate guy
But when I looked in her eyes well I almost fell for my lola
Lo-lo-lo-lo lola lo-lo-lo-lo lola
Lola lo-lo-lo-lo lola lo-lo-lo-lo lola

I pushed her away
I walked to the door
I fell to the floor
I got down on my knees
Then I looked at her and she at me

Well thats the way that I want it to stay
And I always want it to be that way for my lola
Lo-lo-lo-lo lola
Girls will be boys and boys will be girls
Its a mixed up muddled up shook up world except for lola
Lo-lo-lo-lo lola

Well I left home just a week before
And Id never ever kissed a woman before
But lola smiled and took me by the hand
And said dear boy Im gonna make you a man

Well Im not the worlds most masculine man
But I know what I am and Im glad Im a man
And so is lola
Lo-lo-lo-lo lola lo-lo-lo-lo lola
(, Fri 16 Mar 2007, 7:45, Reply)
Cruised into a bar on the shore
Her picture graced the grime on the door
She a long lost love at first bite
Baby maybe you're wrong, but you know it's all right
That's right

Backstage we're having the time
Of our lives until somebody say
Forgive me if I seem out of line
Then she whipped out her gun
And tried to blow me away

Dude looks like a lady

So never judge a book by it's cover
Or who you're going to love by your lover
Love put me wise to her love in disguise
She had the body of a venus
Lord imagine my surprise

Dude looks like a lady

Baby let me follow you down
Let me take a peek dear
Baby let me follow you down
Do me, do me, do me all night
Baby let me follow you down
Turn the other cheek dear
Baby let me follow you down
Do me, do me, do me, do me

Ooh what a funky lady
She like it, like it, like it, like that,
Ooh he was a lady

Dude looks like a lady

/apologies :-)
(, Fri 16 Mar 2007, 7:42, Reply)
Young lady.
On more than one occasion I have been called "young lady" by elderly gentlemen when they're trying to get my attention. This is fair enough as I have long wavy hair, and from the back I might look female in the eyes of an older generation.

What confuses me, though, is that these events usually happen when I'm wearing my motorcycle gear; boots, leathers, Pink Floyd t-shirt. I don't get it. Were there a lot of women bikers in the 1950s?
(, Fri 16 Mar 2007, 7:34, Reply)
Drag queen
I'm fat, and I used to be fatter. I was invited to my sisters' now-ex's 21st, which was to be a cross dressing party. I'm always amazed by how easy it is to get tradies to frock up. Anyhoo, as a fat woman with F-cup bazooms, the usual female-to-male options were largely closed to me (footy player, schoolboy etc), so I did the postmodern thing and went as a drag queen. I wore a huge sparkly turquoise polyester frock, teased my hair and put my eyeshadow on well above the level of my real eyebrows. Given that I have eyebrows like Bob Menzies this was quite an achievement.

Just to show you how long ago this was, Mum and I looked in the shops to find some glitter to put on my face, and couldn't find any. Now you can't buy lipstick that hasn't got asphalt in it.
(, Fri 16 Mar 2007, 5:20, Reply)
croc_mad's ex
croc_mad's ex looks exactly like Amanda Keller!

Also, vote 1 greenycrimson. I'm sitting here in trackies and trainers and I feel soooooo liberated. I'm in touch with my chavininity.
(, Fri 16 Mar 2007, 5:11, Reply)
Unfortunately (or fortunately, depending on who you are), I've done the cross-dressing stint. I've always imagined that any musical instrument will make great demands on your mental and physical faculties, but this beats the cake. For a concert, I had to play a trombone piece as part of a trio.

This may not sound all that hard to do, but here's what we had to don:

1) Take a choice of three tutus. I got the blue one. My (slightly disturbing at the time) friend pounced on the pink one.
2) Pull on a pair of stripy footy socks
3) Wear glow-in-the-dark streamer-type hair

I wouldn't have minded really if I didn't feel like a tit standing up there, most of my hairy leg on display, and looking like a ballerina going to seed (alongside two other guys just as grotesque).

Apparently some people still have video footage of the performance, though why on earth they'd want that I don't know...
(, Fri 16 Mar 2007, 4:37, Reply)
I agree greenycrimson
I hate wearing dresses or skirts. I only wear them when forced (weddings/funerals). You would normally have to kill me and put the dress on me to get me to wear one. Then I'd just come back as a zombie and strip. Better naked than in a dress.
I hate high heels. How the hell are you supposed to walk in them?
Pockets are a must. I hate purses. My mom's purse is the size of Godzilla. Seriously, I expect it to attack Tokyo any day now.
(, Fri 16 Mar 2007, 3:16, Reply)
Does it count if I'm a girl?
I'm sure I'm not alone on this one; I'm a girl and I don't wear skirts. It's fair to say I don't 'do' girly. Ever.

I own one skirt and that's been worn once in the past 4 years. I live in filthy jeans. I'm happiest in a pair of baggies with huge pockets. What do you want a handbag for? I need pockets. Strappy little tops and kitten heels to go out in? I've got 3 pairs of very stompy boots and T-shirts are comfy. I wear less make up than most male teenagers.

So when I have to go to a formal do in a dress I really do mean it when I say I feel like a transvestite. A transvestite with breasts, but still a grade A tranny who isn't sure how to walk in the pointy, strappy things on her feet.

I'm not alone on this one, am I?
(, Fri 16 Mar 2007, 3:05, Reply)
School uniform
I went to a fancy dress party some years ago, and what with my goatee, long hair on the head and much in the way of body hair, thought it would be best to dress as a schoolgirl. Asked my friend from high school if I could borrow his sister's school dress. No probs, wore it to the party, had a great time.

A few months later, his sister asked about the dress. I refused to give it back, figuring it would lead to more comedy value at future parties and the like. Especially since you can't bend over or sit down in the thing. Have worn it a few times since for various events, and has always been well received.
(, Fri 16 Mar 2007, 2:18, Reply)
Mates birthday in the first year of uni saw us all dressed up as things begining with the letter of her flat; P.

She baggsied pirate and my flatmate quickly nabbed paedophile so that was out. I don't know any nuns so I couldn't go as a penguin and there was no way I was going as a penis (I have some dignity, honest.)

So prostitute it was. A quick trip round the charity shops and a delve into my ex's draws and I was ready to go out (but not before polishing off the bottle of white lightning you see elegantly modelled below:

Thankfully for us all you can't really see my face but yep thats 6'6" of pure man-whore.

We went to some swanky club night, which involved lovely confrontations with bouncers, the hand-cleaner guy in the toilets who wanted to kick me out for being a tranny, and just various fucking weird people you generally meet oon a night out. While I'm sure there were hilarious consequences to amazing anecdotes in there somewhere, I was white cider infused powerdrunk so I have no real details.

I guess both genders of clown come together into some monogendered creature of pure evil. I am twunting terrified by clowns, which also acts as my late entry for last weeks 'when were you last scared.' Good excuse to post a picture of the tattoo my mate just got done, neatly depicting what I believe they deserve.

But don't I just wear those suspenders? You want me.
(, Fri 16 Mar 2007, 1:22, Reply)
Maybe the frilly ones would have been better
Borrowed a girlfriend's (just a friend who is a girl) undies, as mine were filthy after a night of partying. Bloody uncomfortable! Who the hell wears women's undies for pleasure?! In fact, why the hell do women wear them? The commando club's got a lot going for it, and not just ease of access.
(, Fri 16 Mar 2007, 1:00, Reply)
Cross Dressing

The night my boyfriend came over, fooled around with me in bed and 'got his' without so much of a sniff of an orgasm for me, then asked me for a lift home

I've never been so cross to be getting dressed.
(, Fri 16 Mar 2007, 0:36, Reply)
Cross Dressing
Has anybody else wore a lampshade before? they make cracking mini skirts.
(, Thu 15 Mar 2007, 23:49, Reply)
Hot cross dressing
I'm a welder, so I guess that I've been cross-dressing for my entire career. Welding jackets, coveralls, etc. just aren't made to fit women. If they fit around the breastular area, they're just too big everywhere else. I can't count the number of articles I've had to rework so they fit properly so that I don't get showers of sparks up sleeves, down necks, etc. Don't even get me started on gloves. It's nearly impossible to find any small enough, and my hands aren't THAT tiny. I don't know how convincing I am as a man in my welding kit, however: the breasts and waistlength hair tend to be a bit of a giveaway.

It's very frustrating, and not at all sexy (despite how it looked in Flashdance).

Length? My lack thereof is the problem...
(, Thu 15 Mar 2007, 23:43, Reply)
I'm wearing my girlfriend's shirt right now. And damn good I look in it too.

I think there is actually a generation of crossdressers coming up. Every single 13 year old boy with a myspace wears his sisters clothes, sounds pretty transvestite to me.
(, Thu 15 Mar 2007, 23:34, Reply)
Red Nose Day nearly killed me...
1988 or so... one of the first red nose days... me and my friends (half of which are cool, funny, good looking girls) decide the Saint Trinian outfits will be perfect dressing up amusement for a comprehenisive 4th form.. ie. 14/15 year olds... we turn up in the girls gym skirts with US flag boxer shorts, net tights and white shirts with ties to be a bloke-ish aside to the bright red lipstick... you know... irony...
Not so welcome in Rothwell, Leeds... old pit town that had just gone through years of mining and teacher strikes...

Jeans went back on at lunch...

I had a couple of beatings at that school...

Funnily enough.. I'm still wiser, happier, more worldly and RICHER than them all... I admit I'm shallow... still don't get laid enoug though!

I didn't like the tights... but I'd kill to defend any of those twats that ridiculed me if they did now.

Duality is a bitch!

P.S. I have lived in London for 8 months... odd place.

(, Thu 15 Mar 2007, 23:31, Reply)
Cross Dressing
The day I stopped wearing skirts in public was the day a squirrel ran up my leg looking for nuts.
(, Thu 15 Mar 2007, 23:25, Reply)
has anyone made a token mention of kilts yet?
they don't feel feminine and they weigh a feckin tonne ... skirts: not all gay, 100% fact
(, Thu 15 Mar 2007, 23:15, Reply)
I was a boy once...
This is touchy for me... I was NOT a cute kid. I had a mullet, and what's worse, I had to wear my brother's hand-me-downs. Everyone thought I was a boy. One time in particular, me and my dad went to an auto parts store to get a part for my dad's car. The guy behind the counter said, "Oh my Jonnie, I didn't know you had another son."

Fucking scarred me for life, that mullet did.
(, Thu 15 Mar 2007, 23:01, Reply)
is my ex-boyfriend. Dressed as Courtney Love.

I went on a first date a few weeks back with a guy known as 'Mouse.' It was going well until he casually mentioned he was into "Tranny Porn. The classy stuff mind (seeing the look on my face.) - chicks with tits and dicks, no old men or anything..."

Look out for more stories, I've got far too many to add to this QOTW than is healthy.

Edit: The same guy just sent me this: www.jassminejames.com ... apparently that's one of "the better ones." NSFW or anyone of a nervous disposition.
(, Thu 15 Mar 2007, 22:55, Reply)
I played a woman in a school play once.....
but that was years ago. chavs (teenage scum) nowadays look extreamly alike, thay all wear the same clothes.

not to mention that most of the young women in the calder valley look like men anyway (and fight like them)

... then there was one time on a cadet camp where about 20 of us got dressed up in drag
(, Thu 15 Mar 2007, 22:52, Reply)
A few years ago, while doing my A-Levels, I had to come to a venue in central London for a day of tedious lectures. Afterwards I decided I'd visit a few shops and in walking down Oxford Street I saw in the space of two minutes a woman walking into a building wearing a painted on football shirt (yay) and a piss stinking tramp wearing a faded, stained, pink dress (boo).

Given the anecdote posted in posing this question I can assume that the site is either run by tramps or men only wear womens clothes if they are drunk.
(, Thu 15 Mar 2007, 22:47, Reply)
I have on occasion..
I've done the obligatory schoolgirl at the back to school party at uni - Wig, skirt, suspenders and stockers etc. Had a good time, went back to my room with my (then) partener at the time. We get down to funny stuff, but I'm too lazy to remove the stockings... and it felt rather good.

Move on a few more years, and I'm performing as Frankenfurter in a local version of Rocky Horror (great fun!), and I'm being driven home by my (current) girlfriend... bedroom activities occur, and again I'm too lazy to remove them. After, she says that she rather likes it.... and I have to admit, so do I. So I now have my own collection of stockings for assorted bedroom fun for the two of us (which she keeps nicking when she's over here!).
(, Thu 15 Mar 2007, 22:41, Reply)
I don't cross dress
I'm a bloke.

*downs pint and has a wank*

though my hair is exceptionally long.
(, Thu 15 Mar 2007, 22:35, Reply)
Funnily enough...
I'm sure I'm not the only person on here who actually *is* a crossdresser/tranny/whatever the hell you'd like to call people with certain...hobbies.

And in response to both Big-girls-blouse and Fothermucker (for opposite reasoning) have this.
(, Thu 15 Mar 2007, 22:28, Reply)
Apparently I'm a size 16
My internet Mrs (who at the time was my internet bird) had a load of clothes she wanted rid of, and I'm a great customer/supporter of charity shops so rather than just get shot of them I said I'd take them to my local Oxfam. Sorting them into bags I came across a "little black number" as I believe the ladies call them, in velvet, so I thought I'd put it on and when she came round it greet her at the top of the stairs with an Audrey Hepburnesque "I feel fantastic!!" whilst leaning over the banister in a a 50's film star stylee. Brilliant laugh I thought. So I'm listening out for cars to pull up and getting into position, car pulls up, footsteps up path, my flatmate's shape through the frosted glass. Bugger! Leg it into bedroom and put dressing gown on, act normal (albeit with tighter gown than usual), he says he's just popping to Safeways, no probs, bye. Phew! Relax again, resume listening, car pulls up, stand at top of stairs looking wistful, footsteps up path, flatmate's girlfriend's shape through the frosted glass. Bugger! Leg it into bedroom and put dressing gown on, act normal (albeit with tighter gown than usual, again), tell her that he's just popped to Safeways, no probs, bye. At this point the whole sponteneity of the wizard dress gag starts to fade until another car pulls up. Resume position, my girlie's shape appears through the glass, door opens, "I feel fantastic!!" I say, and she just laughed at me. At that point I realised I looked a complete tit as opposed to the comedy event of the evening. To this day she is good enough to remind me that if I have an idea it's probably going to end in humiliation, tears and disaster.

Which is nice.
(, Thu 15 Mar 2007, 22:23, Reply)

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