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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.

a uni story.... (/unlurk)
aren't they all?

way back in my second year of uni, the friday night union party ran themes, and one week the theme was cross dressing. given that i'd done every theme that term, i wasnt about to shirk now, depsite being a chunky, hairy sort who should never been seen in a skirt.

i'll set the picture... the world's shortest white rar-ra skirt, and a top several sizes too small. unshaved legs, and topped off with trainers, in a look lily allen has since stolen. one wig and a bit of lippy later, i was a confirmed "15 pinter" according to all my mates.

ok, so blokes didnt go for me, but girls sure as hell did... all night i couldn't keep random ladies hands off me, much to the disdain of the then-girlfriend, and much to my own surprise (female attention not being something i'm known for).

one girl was particularly attentive, not that i minded, she was very cute.. however she went too far and started trying to unzip my skirt while i was queueing for the bar, and in a moment of sudden clarity that i'm incredibly proud of given a) my drunken state and b) the quality of the line, i turned to her and said

"i'm sorry, i'm just not that kind of girl"

her disappointment was palpable.
(, Tue 20 Mar 2007, 10:52, Reply)
A few years back I was mistaken for my cousin Chris. Christina that is.

She's my height, build, etc - but she has a womanly walk and figure and I, well, don't. (Although that's not what gay men tell me - meh).

Does that count???

I mean, I was wearing her coat and all that, but our hair was totally different - I even had a "Fresh Prince" flat top and everything.

Well, so did she....

And yes, I looked like a proper twat.


Make this painful QOTW end!!

It's my birthday soon :o)
(, Tue 20 Mar 2007, 9:30, Reply)
bloody philistines!!
I got battered because of a traaaansvestite once.
Back when I was running public houses I was manager of the largest and newest place in town, so it was always busy.
Not long after we opened, we started to become frequented by a six foot two pre op guy in full-on lady regalia.

The locals around here are a manky-wanky bunch at the best of times, so he/she was considered fair game.

I, being the responsible landlord. took umbrage to this, and proceeded to tell the small minded buggers to pack it in.

They kicked me all over the effing shop next time they saw me out on my own.

But I'd bloody well do it again.

Dirty manky Telford scum pikey gyppos.
(, Tue 20 Mar 2007, 9:27, Reply)
Technician at Cardiff Uni Engineering department
Can't remember what its name was, but this thing (I will not assign a gender) was freaky.

It had gone all the way as far as I remember and there was even disciplinary action threatened amongst the staff if they referred to it by its male name.

This thing looked like it lived under a bridge and gobbled billy goats, but had slipped out and donned a bob wig and a skirt and stomped around the computer rooms muttering (think Foul Ole Ron from Terry Pratchett's Discworld) and stinking (think Foul Ole Ron from Terry Pratchett's Discworld)

(, Tue 20 Mar 2007, 9:13, Reply)
Once,I made a shit pun on a QOTW instead of letting people tell their funny anecdotes.

Then I made a joke about length.

Go back and compare this thread to the "best" of the Poo Stories - that's actually funny. This is rubbish.
(, Tue 20 Mar 2007, 2:55, Reply)
Cross Dresser

I once nailed a transvestite Jesus to a crucifix and covered him with balsamic vinaigrette.. Even then this joke wasn't funny as I was angry at having to clothe myself.

I guess that makes me a dangerously unfunny wanker
(, Tue 20 Mar 2007, 2:18, Reply)
They get right on my tits.
(, Tue 20 Mar 2007, 1:55, Reply)
I once poured on balsamic vinaigarette.
Instead of blue cheese dressing.

Oh, boy, was i cross!
(, Mon 19 Mar 2007, 23:12, Reply)
That would be an average Saturday night then...
I've been to university, so blokes in dresses became rather common for me. However at the Student Union Cross-dressing night, despite being a girl I wore a skirt. It seemed appropriate, seeing as I hadn't worn one for the preceding 18 months.
(, Mon 19 Mar 2007, 22:54, Reply)
i always thought it was strange that my mum had a beard.
(, Mon 19 Mar 2007, 22:19, Reply)
I was in church one Sunday and I was looking for a place to hang my coat. I eventually found this big bit of wood with a couple of sticky out bits which looked like arms which was perfect for me to hang my jacket from, so I put my jacket over the arms, wrapped my scarf around the neck and put my woolly hat on the top bit... From that day forth, I was a cross dresser.
(, Mon 19 Mar 2007, 20:42, Reply)
I have worn a dress on a few occasions. Once I had to wear a dress for a whole weekend rugby tour. It was white with green and purple and yellow flowers on it. Lovely. And amazingly enough, I still managed to pull a young lady. However she may have been a very drunk lesbian.

Anyway, being a kilt wearing Scottish personage, I'm sort of used to the sensation anyway. It's not that bad. At least I don't sit and get all concerned about whether or not I've been wearing "boy-shorts" or not. I mean the phrase "boy-shorts" is probably the gayest thing I have ever heard. No, in terms of underwear, it's sandpaper in the y-fronts or nothing for me.
(, Mon 19 Mar 2007, 20:26, Reply)
I once pretended

to be a member of the Socialist Workers Party, when really I'm a member of the Revolutionary Socialist Party.

It felt very dirty.
(, Mon 19 Mar 2007, 20:23, Reply)
Cross Dressing?
I once made vinegar on a salad very annoyed....
(, Mon 19 Mar 2007, 20:14, Reply)
Hello, my name's EricPhillips and I'm a cross-dresser
Contrary to what my username might suggest, I'm actually a girl. However, I am a 6'1" girl with an interest in amateur dramatics. Now in our area, amdram seems to be about as popular with men as ballet is with builders, so I have oft played men. Most recently I've been a male convict, a neurotic Irish hangman and a policeman.

However, my first experience of crossdressing was for a club night at The Hippo Club in Cardiff (god rest it's techno soul) where they had tranvestite DJs and anyone cross-dressing got in free. A workmate of mine and I went as a couple - he in a pretty lacy cardigan, curly auburn wig and tiny miniskirt with Cat boots and I in one of my dad's suits with a drag-king moustache. Whilst we both got in free, he had a better night than me as after about an hour I lost him only to later find him exchanging oral fluids with some woman in the corner.

It was only later that he told me that the woman in question was a) e'd off her face, b) a lesbian and c)so shocked when she reached under his skirt and found his cock that she nearly knocked him out.

In the copping off stakes, I don't know if that counts as a good result or not?
(, Mon 19 Mar 2007, 20:13, Reply)
Boy Shorts
I like them. I also like french knickers. They're just hotter than thongs and briefs and blah blah. Since I'm a straight bloke, they clearly are for girls. So there.

I have not worn girls underwear. Have worn a dress on two seperate occasions, though. Yes, you do get a lot of female attention. In my case, though, they were all ugly. Typical.
(, Mon 19 Mar 2007, 18:37, Reply)
boy shorts
i have to agree with the lovely chickenlady, i also have a couple of pairs of lacy boyshorts and they've always got the right result when flashed under a short skirt or revealed under jeans/suit trousers! i'm not brave enough to post a picture though.

also, as they are pink or red, i don't think they fulfil cross-dressing...

but my obscenely fit friend always wears boys' boxers. she loves them. doesn't seem to have put anyone off yet, either!
(, Mon 19 Mar 2007, 18:15, Reply)
Rocky Horror Picture Show, Halloween, 1990.
I still had hair then, and I teased it up, put on a leather skirt, red sweater, full make-up and 44-DD bra stuffed with socks (I'm a guy, by the way). I didn't shave my legs, so in panty hose they looked like uncooked bratwurst. I also couldn't find mens size US12 high heels, so I had to go in tennies.

On the way to the theater, there were a couple guys walking behind us. I guess they heard me talk because suddenly they burst out in disgusted laughter. To prevent contraband, they had men patting down the men and women patting down the women at the door. I got patted by a woman. She nearly fainted dead away when I asked her if she wanted to check my purse. She just hurredly waved me in, looking a little ill.

Before the show, they had all the Rocky virgins go up front. Several eyes popped out in the front row with exclamations of "you've got balls!"

All through the show, my girlfriend kept reaching up my skirt. "Now I know why you guys like these things. Grroowwwwll!" "Stop that!" I said, slapping her hand away.

There are pictures somewhere, just waiting for me to run for President.
(, Mon 19 Mar 2007, 18:00, Reply)
Derek Acorah’s Spirit Guide Sam
Erm, I wear boy shorts, the lacy ones, and rather nice they are too….Yes, they are like hotpants, frilly hotpants…And I don’t find they ride up either….
And yes, here's a picture….it’s blurred I know….There is a better one that can be found on someone’s Live Journal….if you’d like to see it gaz me and I’ll send the link…….
(, Mon 19 Mar 2007, 18:00, Reply)
Boy Shorts
In all the frilly lady knicker shops, you can buy lacy man-pants called boy shorts.

I CANNOT understand why any lady like myself would buy these. If you want sexy and frilly, get a thong or some french knickers (if you dont want string up your behind).

If you want man pants, WEAR man pants, not these freaky net curtain wrap around hotpant affairs. Anyway, they ride up under jeans and give you a wedgie.

Men, if you find boy shorts sexy on a woman you are strange. I mean BOY SHORTS! Could they make them sound any more like a choirboy's holiday wear!? They sound like they come from the 70s and should be light blue with fetching brown flowers (even THAT sounds homoerotic) over them and worn by hairy builders in Benidorm.

They. Are. Not. For. Girls.
(, Mon 19 Mar 2007, 17:29, Reply)
Cock in Dress
I meandered towards my (now ex, read on for why) boyfriend's room and opened the door without knocking.

Did I find him in female attire? No.

Did I find him perusing the man-ladies on the internet? No.

I found him preening his hair with coloured hair gel and bobbing his head slightly so that my butterfly hairgrip's wings flapped and twinkled in the light.


But it was when I took my sparkly cocktail dress home from his to wash and found it stretched to Vanessa Feltz size did the truth hit me.

I'd interrupted the sacred pre-tranny ritual.

We are no longer together.
(, Mon 19 Mar 2007, 17:14, Reply)
Dragged Up
I'm a girl, and quite a well endowed one chest wise. I also have long hair. I look girly. None the less, I'm often mistaken for a boy (and a very young one at that). I was once refused by a cashier in Waitrose when I tried to buy a bottle of gin. Me - 24 year old girl. She assumed I was male, and underage. I was outraged. She served me the gin pretty quick after that.

I have used this boypower to my advantage - I was at Brixton Academy watching a gig, standing on the side near the boys toilets. Couldn't be arsed to get all the way to the other side to go in the girls toilets, so I fooled the bog-bouncer by putting on my boyfriend's hoody and carrying his pint in with me.

Didn't miss much, and I remain happily lacking in length/girth.
(, Mon 19 Mar 2007, 17:05, Reply)
Themed Fancy Dress Party
I once got an invitation to a fancy dress party, where the theme was cross-dressing. I decided to be witty and only put one of my arms in the armhole of my shirt and act bitter for the whole night, so I didn't have to embarrass myself dressing up as a woman. Surprisingly, I was the only person there with this idea. Unlike this QOTW, where everyone's doing it.

However, I discovered something very exciting lurking at the party -- women in suits. They look so very proper, but you know they're well-and-truly gagging for it. In particular, there was this tall brunette dressed up as a policeman. Her hair looked quite abundant, tied in a well sized pony tail trailing down her slender back towards her shoulder blades, while her black-rimmed glasses sat pleasantly at the end of her nose just in front of a pair of pearly blue eyes. With the policeman's cap cocked playfully to the side on the top of her head, she already had my attention, and I felt my member begin his respect for her authority.

I couldn't take my eyes off of her, and before I knew it I was admiring her tall form. She wore a black jacket, hung loosely around her shoulders, over a gleaming white buttoned shirt that was obviously a bit too small for her. Her large, rounded breasts were pressing heavily on the silky fabric that, like me, looked ready to burst. They were also incredibly firm, as she was clearly wearing no bra and the superlative jubblies stood as proudly and pertly as a head choirboy.

The shirt was tucked into her belted, black trousers that were sitting at the top of her shapely waist, and they dangled comfortably around her long legs. I could just picture the exciting boxer shorts she would have on underneath, perhaps with a jokey picture on alluding to possession of a penis, while all along it not-so-secretly hides her glorious mound of pleasure. Just looking at her, I ached to know her. Somehow, after a good few cocktails and glasses of wine, we got chatting.

Her name was Lucy, and as she talked her nose wiggled in a surprisingly buoyant yet curiously attractive way, while her small, spongy tongue eased the syllables past her luscious red-lipsticked lips. Surprisingly, she liked my outfit, as it advertised my burly figure and she had no interest in chatting to a bunch of "ill-adjusted cross-dressing freaks". I took this as permission to compliment her on her outfit, and I did so commenting on how incredibly sexy she looked. All of a sudden, her demeanour changed, and she grasped me firmly at the scruff of my shirt in a mildly aggressive manner.

"How dare you talk to an officer of the law that way! You're going down,", she said. Then, with a sly wink, she promptly dragged me up the stairs to one of the vacant bedrooms, and threw me down on the bed. She took off her hat and dropped it carelessly onto the bedroom floor, before letting her hair down. The streaks of brown radiant hair dangled over her shoulders and back and she looked purely animal. She climbed on top of me, setting her legs around my waist where my engorged manhood was happily waiting beneath my jeans.

"You have the right to remain silent," she growled enticingly, "but there'll be no chance of that", and she let her jacket slide off her arms and around my ankles, then leant forward and pressed her body against my bare chest, and her erect nipples pressed delicately through her silk shirt into my skin. She kissed me passionately, and I tore her clothes off of her body, revealing her wonderful, white, siky skin and began to kiss it willingly. She took her trousers off, and I saw she was wearing a neat pink g-string, although not for long as I pryed it off with my teeth and pleasured her generously.

Her moans of delight reverberated about the bedroom, and I climbed on top of her. She grabbed me by the waist and swung me around onto the mattress and sat atop me again, eyes fierce like a lion. "I'm the ranking officer here," she commanded as she guided my twitching ardour inside her, "so do as I say. Don't stop until the bed breaks" and she started grinding away ferociously, grabbing her hair and leaning back at the same time, presenting the full shape of her voluptuous figure to me. What followed was the most mindblowing sex ever had, obeying her every desire as she dictated position after position until I exploded my burning ejaculate into her tight lips and collapsed onto the bed, sore with satisfaction.

She stood up and got dressed. She looked at me sternly, and uttered "If you tell anyone about this, I'll see that you get the chair" and walked out, leaving my ragged form tired and broken on the bed.

So, cross-dressing, I'm all for it.
(, Mon 19 Mar 2007, 16:19, Reply)
one of my close friends...

Photo Sharing and Video Hosting at Photobucket

my boyfriend...

Photo Sharing and Video Hosting at Photobucket

The friend was dressed as the worst saloon hooker in history for the National Student Rodeo, and the boyfriend was wearing a Drinking Dress during a pub crawl in York. I'm still not 100% sure why.
(, Mon 19 Mar 2007, 16:17, Reply)
although I've already answered, I'd just like to say...
kudos to all those ladies with enough balls to post pics ;-)

[shameless votewhore: click ILT if you agree :P]
(, Mon 19 Mar 2007, 15:52, Reply)
I don't understand g-strings
They come with a bit of fabric at the back which covers my bum and some string at the front which only seems to serve to tie around my......

Oh, hang on.......
(, Mon 19 Mar 2007, 15:47, Reply)
I don't understand boxer shorts
It's great that they come with a hole in the back for shitting out of, but I pee a lot more than I poo. Surely a hole in the front would make more sense.
(, Mon 19 Mar 2007, 15:16, Reply)
The Holyrood Tavern
For those who live (or have lived) in Edinburgh, I'm sure the landlord of the Holyrood will stick in their minds. It's a shabby rock pub (cleaner than it used to be- it now comes with seats in the chairs) with decent beer in the old town, often frequented by students, festival tourists and rockers. I have seen it set upon and drunk dry by Hell's Angels.

But back to the landlord. He's an absolutely lovely chap with long white/grey hair, decent face-hugger of a beard and the slight tendency to dress as a lady. On the mild days you can expect a little bit of nail varnish, perhaps some eyeliner and/or eyeshadow on an otherwise unremarkable man in a checked shirt and jeans.

One day I wandered in for a quiet pint and he was wearing a T-shirt and kilt; normal in Scotland? Not when it's a girl's mini kilt that doesn't come halfway down his thigh. Thankfully, no hairy plums were seen escaping.

During the Fringe, that wonderous festival that invites loonies to crawl out of the woodwork, I've seen him resplendent in tight black PVC bodice, slashed to the thigh skirt, stockings, heels and more slap than Dame Edna.

If you're in the city near the Cowgate at any time I heartily recommend you going in- the food's good if their chef hasn't run away again.
(, Mon 19 Mar 2007, 15:01, Reply)
There is a trannie that works at M&S in Nottingham and she/he/it wears a red wig. I think she/he/it's a legend. I am surprised that M&S went for the whole gender-bending thing though, they've got quite a conservative image and a 6'3" man in a ladies' uniform isn't really in line with their corporate branding.
(, Mon 19 Mar 2007, 14:51, Reply)
I have never cross-dressed myself
but once again I can relate a lovely story about Stalker Boy.

Stalker Boy, or so I hear even though I haven't seen or heard from him in nearly a year (woo yay!), is well known in his uni town (Nottingham) for being the "six foot three fat bastard who walks around in ladies' clothes from Oxfam thinking he looks like Emily Howard*". The mind boggles. I understand he has a parasol and everything. He also openly admits to enjoying tranny porn.

The roots of this probably came in school, when they formed a gospel choir. Someone decided we were going to sing Oh Happy Day like they did in Sister Act, and Stalker Boy, who at the time would have been about 15, had the wonderful idea that he was going to dress up as Whoopi Goldberg. With the dreads and everything. For one wonderful moment when we performed it looked like he was going to bottle it and just come out with the rest of us and be moderately humiliated, but it was not to be.

I think he's quite deserving of the words of Eddie Izzard: fuckin' weirdo transvestite!

* Little Britain character for the unaware.
(, Mon 19 Mar 2007, 14:16, Reply)

This question is now closed.

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