Not me but a very distant ex
I dont mind admitting Im a newbie, so please be gentle!

This isnt about me but a very distant ex... One day I had left his in a bit of a rush and *ahem* left me thing behind (as you do). The next day I went to see him he greeted me at the door wearing them! He was a big lad so it wasnt a pretty sight... well the neighbours didnt think so... later he confessed to wearing them whenever he wanted to think of me... eugh
(Fuzzy_footed_chicken, Sat 17 Mar 2007, 23:26, Reply)

I spent the first 20 years of my life cross dressing.
Actually, that's it. It wasn't particularly funny, sorry.
( John Barrowman's laminated buttocks, Sat 17 Mar 2007, 23:19, Reply)

Feminist housemates
We need a new house to stay in. Me and my flatmate because if we don't find 3 people ourselves to sign a group contract we're on the streets. It's not looking good and I start looking for somewhere else to live. So I find a poster saying that there are two rooms available at a cheaper rate than ours at the moment. I get a phone number and ring them. I ask if they have found anyone to fill in they're two rooms, "no" she said, "do you mind if I come round and see the rooms?" I say all excited. "Umm. We're actually looking for two girls."

So it was a no. I'm thinking that I really need this place to live so my mind turns to crossdressing. I tend to stay up in my room most of the time wherever I live so I think I could get away with most of my time there dressed as a guy. The first step was to phone them up with a womans voice. So I listen to a radio play on Radio4 and try to copy the female voices. I call them up and then they offer me a room.

The problem is now I have to go and see the room. I've not done so yet but I've done a fair amount of research into fashion and cross dressing in general. Maybie I should look for somewhere else.
(WiggZ, Sat 17 Mar 2007, 22:13, Reply)

Nun
Err, just so happens I'm dressed as a nun right now. Does that count?
(......, Sat 17 Mar 2007, 20:51, Reply)

Quite a lot actually...
..I think probably due to my cousin using me as her very own doll. Her and her friend would dress me in whatever cast offs they had about and do my nails and crimp my hair (it was the 80s) then send me out to parade in front of the adults singing "he's got to be big and strong".

This probably had something to do with me dressing as posh spice for a charity thing in my last year at school, and performing a choreographed dance to Spice Up Your Life. We won too, the teacher awarding the prize looked at me a litlte too much.

Then there was the drunken decision by my friend and I to get dressed in drag while in Ibiza and go to Manusmission...which has the club Trade in the back, so to speak. Quite possibly the gayest club night anywhere. As I walked by a rather butch guy wearing a sailors outfit I said "heelloooo saiilllooorrr" in my campest voice, which I found quite funny. He then proceeded to follow me around most of the night and trying to dance with me...which I didn't find so funny.
(I-boy6655321, Sat 17 Mar 2007, 20:39, Reply)

It was just the other week...
Just last week, I was in my bedroom, parading around in high-heels, stockings, suspenders, thong and a lacy bra.

I turned round and was shocked, to see my 12-year old son looking at me from the bedroom door.

Then I remembered: I'm his mother!

With apologies to apeloverage.
(apologies_for_length, Sat 17 Mar 2007, 20:20, Reply)

Good question...
Been doing it since I was a kid. Doing it now actually. Anyone got a problem with that?
(minimalist ..., Sat 17 Mar 2007, 17:06, Reply)

Walked
into a room of naked nuns showering. They suddenly became very cross dressers.




What?
(barrycounty, Sat 17 Mar 2007, 16:52, Reply)

Aah, 1st year at uni...
It was close to hallowe'en, and it was a mate of mine's birthday, so I decided to get into my then-girlfriend's Lycra LBD (Little Black Dress), put on a pair of DocMartins, gel my hair back (a la Jamie-Lee Curtis in True Lies), put some lippy, blush and eye-shadow on, and to top it off, drew a little anchor on my arm with the word 'mum' on the side. In short: the stereotype!

But the real icing to the cake was that birthday boy in question was in the uni pub, and there was a karaoke going on, and on walks "Laura": me in said LBD, dolled up, boot wearing, with a riding crop in one hand, mike in the other, singing "I'm too sexy".

Not quite sure which was greater/wierder: me winning a prize or my then-gf telling me I looked good in it...thinkin about it, gf saying I looked good in it was probably not a good thing...
( Frisbee OG wanker, Sat 17 Mar 2007, 16:38, Reply)

stolen..

I've never cross-dressed, but once when I was playing chess my pawn went all the way, and became a queen.
(apeloverage committed the vile act of onanism on, Sat 17 Mar 2007, 15:39, Reply)

actually true story

I knew a young and fairly small and weedy, but good-looking guy - he was also a few years younger than the rest of us.

Once we were at a party and he 'got with' a woman, they were snogging for a while. Later I saw him without her and asked where she was - he said she'd thought he was a girl.

He was very disappointed - but it's closer to red-hot lesbian action than most men ever get.
(apeloverage committed the vile act of onanism on, Sat 17 Mar 2007, 15:37, Reply)

Err..
Not really on topic but I found it funny.

Years back I used to work with a psycho in a computer shop. Said psycho knew nothing about computers but was ace at stock control and finance but he should be really kept away from people.

One day this geek came into the shop and said to psycho:

"Excuse me mate - do you sell gender-benders-"

"Are you asking for kick in the bollocks?" growled psycho just before I jumped in and saved the confused geek and took him over to the rack with male-to-female serial converters.

Cheers
( Legless Mister Stabby - shanks for the memory, Sat 17 Mar 2007, 14:38, Reply)

We came in peace for all mankind
she was not happy.
(abignumber, Sat 17 Mar 2007, 14:33, Reply)

A man as a woman as a man?
Despite being male, well over 6 foot tall, weighing in at nearly 300 pounds, and (in my humble opinion) not looking feminine at all, for most of my life since my late teens I've been mistaken for a woman on and off. My style of dressing changed over the years, my hair went from longish to short to very long, beard stubble came and went, but still I get at least one "madam" in there per year.

World's ugliest woman, you say? Last year at a gallery opening photography great and über womaniser Michael Ward mistook me for a woman, and even complimented me on my handsome looks before the fierce stare and unmistakably deep voice corrected him. This from a man who was a legend as seducer of great and glamorous women in swinging London in the 60s, and has been up close and personal with the likes of Julie Christie and Barbara Windsor.

Perhaps I should just give up and go for drag?
(fugue Humming along to the music of the spheres., Sat 17 Mar 2007, 13:13, Reply)

My son showed me some photos of himself and his nice friends
on the 'net.

One was of a group of bizarrely-dressed people having a great time. I couldn't pick him out, so he pointed obligingly.

'That's me on the right. Crouched on the floor in the gimp mask.'

Also wearing, well, nothing I'd knitted for him.

Parents - DON'T send your kids to Oxford. They'll have FAR too much fun.
(Juan Quar is clinging to her front teeth on, Sat 17 Mar 2007, 12:52, Reply)

On the Jewish festival Purim, it's traditional to dress up in costumes.
I haven't really bothered since year six (Wore a flowery dress. Carried a plastic windmilly thing. Called myself a flower bed.) but some of my friends convinced me to come down to the synagoge last year. I'd just cut my hair quite short, so I spiked it, drew on a moustache in eyeliner, wore my normal clothes and went as Leonardo DiCaprio, to whose geeky Russian half-sister I bear a passing resemblance. If you squint. While on acid.

Two days later I went to a Goth themed party in a long black number and lots of mascara, with the same people. This prompted the following comment:

"Wow, Maggie, you're so versatile. Two days ago you were a man!"

Thanks, mate. I try.
(Lieutenant Colonel Oblivious brought to you by intravenous sugar, Sat 17 Mar 2007, 9:54, Reply)

Stealing Strippers Stuff
About 3 years ago my friend Chris and I went out one Sunday to a really seedy strip pub. We got bladdered and whilst watching the ladies take their clothes off we hatched a daring scheme, we decided to steal their clothes. This being a really seedy cheap and nasty pub there was no doorman so the next time two girls came out and did their thing when they started walking round with their collection pot we grabbed their stuff and legged it. Unfortunately for me it doesn't end there as we thought for a laugh we'd wear them down our local that night, we got there and went into the bogs and I put the dress over my boxers and came out to wait for Chris. Chris emerged looking stunning in a blue sparkly dress but then suddenly grimaced and hoiked his dress up where I was treated to a sight of pure evil. He'd got her thong on as well and I could see his balls hanging either side seperated by a large string of nylon like two huge bells. Aaaaargh the memories hurt me
(sugardannyoh, Sat 17 Mar 2007, 9:53, Reply)

So, there's a bunch of about 25 of us regulars
at my local who all do stuff together - 4th July party, Superbowl party, Thanksgiving etc.

About 8 of us are female.

One of the girls decides to have (the equivalent of) an Anne Summers party for the ladies, grand idea!
Ladies only night, with lots of alcohol and sex toys. Sounds good to me.
And sounds good to two of the guys.

One of them, his wife was in the hospital undergoing stem cell treatment/replacement for lymphoma, so he was stuck at home all night.
He roped his best friend into both of them dressing up as women and turning up at my friends house about a 1/2 hour afte the party started - long flowery dresses and blond wigs.

Yes, we let them in. No, we didn't let them try any of the sex toys.

Length? Girth? Try a 10' inch bright pink dildo with a clit vibrator.
( Batshitmentalist is sane for once, Sat 17 Mar 2007, 3:22, Reply)

Just thought of a good one:
I used to work at an electronics retail chain. There was a blindingly obvious full-time transvestite who used to come in every so often and buy stuff. I helped him find what he was looking for a few times.

I swear to God, all he ever bought was stuff for his TV. His TV. Including several MALE TO FEMALE CONVERTERS.

I had to go into the back room for ten minutes to stop laughing.
(The Ghost of Stephen Foster, Sat 17 Mar 2007, 3:09, Reply)

Cross Dressing
Ever since I got caught chugging one out in a history class I've always had a problem getting into a girls knickers :(
(Fatima Whitbread's hardon drugs and the causes of drugs, Sat 17 Mar 2007, 2:46, Reply)

Rocky Horror, hoorah!
I'm already a girl anyway, but like that shakespear play, decided that I was going to be a woman dressed as a man dressed as a woman.

It was quite fun being all tarty, but I had me a long coat. Wearing suspenders, corset and feather boa in Glasgow at night = probably not a good idea.
( vix0r was not Matthew on, Sat 17 Mar 2007, 1:58, Reply)

mrcrabby's just reminded me
of a time i was shopping for trousers (aged about 14) and accidentally picked up a pair of lady's, the shop assistant came over and asked what size i wore as she wore 12 and thought i looked about the same size :(

edit: after reading fatima whitbread's hardon's post, i think i went to school with that lad
(cs192 is sucking on a Koala at, Sat 17 Mar 2007, 0:50, Reply)

Back in the day...
When I was at school, we had the annual 'House Music' competition - it was an absolutely fantastic night, with hours of singing, dancing, and general hilarity. One thing which was very frequently occurring however, was cross dressing. This was generally confined to the sixth formers (of which I was one at the time) - it was rare to get through a the night without someone prancing about in a rather nice man-thong whilst wearing a pair of comedy breasts.

In my last year, we pushed it further, splitting our 70ish strong choir into two halves - boys and girls. Not that impressive, till you mention it was an all boys school. Cue 35 boys & men dressed as women, and 35 boys & men dressed as... Well, men prancing about on stage - impressive but not massively embarrassing. Unfortunately that part of the story is related only to me.

I was wearing a rather nice (and very short) skirt, which, in the absence of a proper skirt, as just a 30cm bit of material pinned round my waist. Underneath, I was wearing baggy boxers. This would not have been problematic normally, but I was also playing the drums (with great style, it must be said). We all file into the hall, and I sit down behind the drum set. *Riiiip*. Oh shit. My skirt is now open. Glance down. And oh, look at that. My left testicle is hanging off the edge of the chair I'm sat on, swinging gently. And hairily.

So there you have it - due to an unfortunate cross dressing incident, I exposed my left testicle to the whole of my school and their parents. "Oh cock" seemed an oddly appropriate comment after the moment...
(Merrep, Fri 16 Mar 2007, 23:56, Reply)

I'm a lady!
No, I really am. I look like one, I dress like one, got all the relevant ladybits/long hair/boobs, it says so on my passport, etc.

Doesn't stop me being mistaken for a man in drag.
I was walking to my mate's house in one of the more 'local' areas of my uni town (Lincoln, Sincil bank, if that helps set the scene), and two bald, thick-necked, chavvy gentlemen appeared and were walking behind me. I had on a black leather trenchcoat, a purply long skirt on underneath, very long hair loose, and big boots with big heels. I overheard them talking as it was a pretty quiet street, they were having some jolly dispute about what time it was, or where some pub was, or something. I then heard one of them say "let's ask that dude there. That's a man isn't it? That's got to be a bloke." This pissed me off, as you can imagine, so I turned around and yelled "I'm a bloody woman, you retard!" And stomped away as fast as my New Rocks could carry me (this is not very far or fast). The man seemed genuinely sorry about their mistake and so then tried to chat me up.... Well, asked for a titwank or something similarly charming. I think I really did run then.
Nice dating strategy, that, when you discover that someone you thought was a man is actually a woman, try and hit on them. "Oooh, a woman, eh?? Get in!" *rubs knees*
(Ryuken-Kai, Fri 16 Mar 2007, 22:48, Reply)

Reading Festival '02
Not quite sure how it happened. We'd just returned from a hearty breakfast and several midday pints in Reading town centre and were stumbling back in the general direction of the festival site when I had the somewhat deranged idea of us all buying flowery dresses from British Heart Foundation, replete with chunky necklaces and handbags, and heading back to the festival.

And so, some 30 minutes later, SIX young men stroll side by side down the street in such clothing, not unlike that scene from Reservoir Dogs. Except with dresses.

Got a few chuckles throughout the afternoon. Best moment was all 6 of us running like the clappers the entire length of the arena (some without underwear) to catch Andrew WK on the main stage.

Embarrasing? Probably.

Fun? Most definately.
(BeardyMat, Fri 16 Mar 2007, 22:08, Reply)

What a coincidence
Found a wee picture of my boyfriend in an old dress this evening.

Doesn't he look pretty?
(greenycrimson I stole the from pyschotherapist, Fri 16 Mar 2007, 21:28, Reply)

Fondled
A while back now in the history of everything that's happened to me I was in a grotty pub in Reading watching a local rock band, and someone started to caress my hair, all down my back. This was a nice thing. I am a 6'5" bloke with long blond hair and after five minutes of being fondled turned round with a smile to look straight in the eye of a Hells Angel, scar across his face and the Blue Oyster leather look. He stopped and said, "Uh, sorry mate I thought you were a girl.". Brain said 'Run Away NOW' and I laughed and turned back round, shuffling sideways. As I went out the door, I turned and saw him talking to a massive fucking bloke with a bald head and two snakes tattooed on his temples, looking at me. I ran like fuck as whatever they had in mind, it wasn't going to be a pleasant experience. I was also wearing my girlfriends pants.
( Brandy_Bumwinkle, Fri 16 Mar 2007, 20:54, Reply)

For a while I went out with a gorgeous bird called Natalie - jet black hair, green eyes, fit as fuck.
I'd got the hint that she was into transvestism (is that a real word?) as a result of a couple of fancy dress parties I went to with her. One of which turned out not to be a fancy dress party but instead a perfectly normal school disco type night where I was the only bloke dressed as a schoolgirl.

Anyway...

I've always had a bit of a thing for those sexy satin chemise style nighties. (This sort of thing)

One Valentine's day I had bought Natalie a really nice scarlet ankle length one. I was REALLY looking forward to seeing her in it. She had known what I was buying her and had actually gone out and bought me exactly the same thing (and was apparently very much looking forward to seeing me in it too)!

Obviously she talked me into wearing it for her and I have to say that snogging a sexy bird while you're both wearing lipstick is an interesting feeling but it's amazing when you're both wearing matching satin nighties!

I can't believe I just admitted that. This QOTW has certainly brought back some rather interesting memories from that relationship!
( Afinkawan Yes I can hear you Clem Fandango, Fri 16 Mar 2007, 20:33, Reply)

Names changed to protect the humble
A friend of mine qualifies as a full-on tranny chaser, so much so that she eventually married one. She spent ages trying to persuade me to get glammed up for a fancy dress party with a theme of 'Khaki, Kinky & Kitsch'. I agreed on the promise that it was an effective pulling technique.

The evening came around and I went over to hers for some serious preparation. (Mr Steve is occasionally likened to Sean Bean, but craggier.) Two hours later and we're ready to set off, all piling into my chums little car. She's driving in a very fetching Lara Croft get-up. (She's blessed with impressive norks.)Her then boyf is in the passenger seat in combats and a red basque. In the back we have three of us crammed in rather tight. My idjit lodger who has worn the only khaki thing he owns: some kind of Indian pyjamas, a gay mate who is unwisely dressed for the inclement weather in a series of studded straps, very big boots, and little else. And I dahlings?,I am resplendant in a spray-on tube of black lycra, I huge wig, about a ton of 'slap' vertigo-inducing heels, and a tortuous corset.
Suffice it say that lodger boy is feeling decidely uncomfortable squeezed between the leather queen and the drag queen.

At the party - a hired out bar in the City near the Barbican - all is in full swing. Despite having trouble with the heels, I get pissed and attempt to dance, falling on my arse at least twice. The downside of all the beer is the frequent trips to the gents, which involves hoiking the ankle length dress to waist level to display the now bruised arse to any chaps using the facility. I get a few comments from beered up tossers, but no worries.

And of course there are gate-crashers! A bunch of beery louts (city wallahs rather than chavs) come lurching down the stairs and start throwing their weight around. Predictably I jump into action, shepherding and goading the twats out. Halfway through this I realise I'm dressed up like a big tart, and not terribly intimidating! However the lager louts move on, and the party heaves a sigh of relief.

A nice young lady comes up to me and thanks me for dealing with the 'crashers. In no time she's feeling me up, which I have to admit was a very erotic experience. Give it a try folks, honestly it works for me!

The drawback was that the young lady only wanted to get jiggy if I was wearing a dress, which was fine for 'jiggy', not so good for a social occasion.

Retelling this story to other girls has always produced the desired results, they're nearly all turned on by it. Guys in Frocks are the future I tell you.

The bastard shoes on the other hand, I can do without...

Length? an extra 4" in those bastard heels. The corset took care of the girth!
(Mr Steve is jobless and fancyfree!, Fri 16 Mar 2007, 19:57, Reply)