So, I cross-dressed last night...

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...and I really enjoyed it. This could potentially become a habit forming. Here's a photo. (with my ex dressed in a manly way) I don't know what it is that appeals to me so much about doing this. I guess some part of me craves the kind of self-attention required to really dress yourself up.

I did it for my friends 21st birthday party. The dress code was "slightly silly", but I took it to an extreme. It was really interesting guaging peoples reactions. A cab driver discreetly asked my friend (out of my earshot) if we'd been at a fancy dress party. The guys in the service station didn't bat an eyelid. Some middle-aged men at the party were devoting way too much attention to my figure (I waved back faux-shyly).

So, who else here has cross-dressed? Got any photos? Interesting stories? Do any of you do this on a day-to-day basis?

― Andrew (enneff), Sunday, 10 August 2003 13:09 (twenty-two years ago)

Back when I was in College, I made my then boyfriend dress up as a 'naughty nurse' for a fancy dress party and despite the fact he was a 6ft 4ins hairy rugby player, he really enjoyed it (though I suspect this was because he was drunk and also most of the other guys had dressed up in something silly too). I even painted his nails and did his makeup for him.

After this party, a few of us stopped to get some chips at a nearby chip shop. We had all been served except one guy (who was dressed as a fairy) when they ran out of chips and had to cook some more. It was a hot summer evening and we said we'd all wait outside for him but then this taxi turned up so we all jumped in that and went home leaving the poor bloke stood there in a tutu, with a queue of drunks and social misfits behind him. I haven't actually ever seen him since, so I hope he was all right.

― C J (C J), Sunday, 10 August 2003 13:51 (twenty-two years ago)

I was a nurse for Halloween once!

― s1utsky (slutsky), Sunday, 10 August 2003 15:36 (twenty-two years ago)

I cross-dressed for a party once. I wore a little black dress. Unfortunately I would now have to wear a BIG black dress.

― Nick Southall (Nick Southall), Sunday, 10 August 2003 15:44 (twenty-two years ago)

only did it when we had to do a little video presentation on _Metamorphosis_ in senior year of high school. I played Gregor's mother.

― Kingfish (Kingfish), Sunday, 10 August 2003 15:57 (twenty-two years ago)

Hot damn!

I tend to cross-dress when I go into dyke mode, but I've no photos that I can post here *making mental note to break out camera next time*.

I'm all for cross-dressing ... gives each gender insight into part of what life is like as the other sex. And (big surprise here) I like the sexual thrill that comes with gender-bending.

To be honest, I put a lot more effort into looking masculine when I'm dressing as contrasted with looking feminine most of the time (no make-up, no heels, etc.)

Andrew, you did a fine job!

― I'm Passing Open Windows (Ms Laura), Sunday, 10 August 2003 22:42 (twenty-two years ago)

I used to totally require my boyfriends to crossdress. Well, I don't know about 'require', but they all agreed pretty quickly so it didn't matter much. obv it is the rox0r. Bravo Andrew! It's so fun to dress up, and girls' things are so much prettier. You can really indulge yourself, and it is soooo sexxxxy!

― teeny (teeny), Sunday, 10 August 2003 23:11 (twenty-two years ago)

Looking good, Andrew! I've only done this rarely but it was fun -- also like getting my nails done.

― Ned Raggett (Ned), Sunday, 10 August 2003 23:45 (twenty-two years ago)

best thread title evah, btw

― M Matos (M Matos), Sunday, 10 August 2003 23:46 (twenty-two years ago)

the drummer in our band is a cross dresser and at this party we attended on sat pm he had a beautiful orange crimplene two piece ensemble that he wore with a black and white polka dot blouse and stunning high heeled boots. he looked amazing. i was dressed as a boy , hoody and jeans and my $1 adidas 70s trainers... but not intentionally. i have been wearing clothes like this for a while cos i cant be bothered doing the girl thing right now.

― hellbaby (hellbaby), Monday, 11 August 2003 04:27 (twenty-two years ago)

I wore a lace teddy once. It was fucking ridiculous. That was the end of my career as a corssdresser right there. It's been mentioned more than a few times that I'd make a terrible woman. Andrew: Nice tits.

― Millar (Millar), Monday, 11 August 2003 04:33 (twenty-two years ago)

I wore a (blue) nun's habit to a Halloween party once, but that's as far as I go.

― nickn (nickn), Monday, 11 August 2003 05:15 (twenty-two years ago)

very convincing in a weird kind of way!

― Pinkpanther (Pinkpanther), Monday, 11 August 2003 08:37 (twenty-two years ago)

I first cross-dressed when I was 17, I had a skin-tight pink dress borrowed from a friend, and another (male) friend also wore a short skirt when we went to see the Midsummer bonfire. We looked rather silly and got laughed at, but we had fun.

Later on, for many months, I used to wear a long black skirt quite regularly. It looked good on me, but then the guys-wearing-skirts became sort of a mini-trend, and I didn't want to appear trendy. I got some nasty comments, obviously, but many folks also seemed to be genuinely delighted seeing me in a skirt. I still have it, but nowadays I only use it when there's some special occasion which requires dressing up. I've never owned a pair of suit trousers, so I combine my suit jacket with the skirt.

― Tuomas (Tuomas), Monday, 11 August 2003 08:54 (twenty-two years ago)

Is dressing up as a boy/girl for fancy dress the same as cross dressing? I mean 'cross dressing' implies more some how.

― Pinkpanther (Pinkpanther), Monday, 11 August 2003 08:56 (twenty-two years ago)

A side question: when you walk around town cross-dressed, do you fear you'll get beaten up? I initially feared this, especially when I was walking alone, but nothing ever happened, so I eventually got over it.

― Tuomas (Tuomas), Monday, 11 August 2003 08:58 (twenty-two years ago)

Is dressing up as a boy/girl for fancy dress the same as cross dressing? I mean 'cross dressing' implies more some how.

Yeah, I was wondering the same, since most of the folks here are only talking about dressing up for costume parties. Even though I used to wear a skirt throughout the week, I wouldn't call my self a cross-dresser, since I had no "deeper" urge to do it, I just wanted to try what it would be like.

― Tuomas (Tuomas), Monday, 11 August 2003 09:05 (twenty-two years ago)

That kinda rocks, Tuomas. I on the other hand am merely growing my nails.

― Andrew Thames (Andrew Thames), Monday, 11 August 2003 09:40 (twenty-two years ago)

I was around the streets and stuff the other night and didn't really feel unsafe. I live in a very transvestite-populated area though.

I think 'cross-dressing' merely implies wearing clothing usually designated for the opposite sex. Be it once or many times. I think 'transvestism' is the term that signifies what you're talking about, Pink.

― Andrew (enneff), Monday, 11 August 2003 10:14 (twenty-two years ago)

Oh no, i didnt necessarily mean to that extent, just more of a way of life as opposed to just dressing up for a party!

― Pinkpanther (Pinkpanther), Monday, 11 August 2003 11:12 (twenty-two years ago)

I was around the streets and stuff the other night and didn't really feel unsafe. I live in a very transvestite-populated area though.

Helsinki, sadly enough, isn't big enough a city to have safe areas for transvestites or for other "perverts". A male friend of mine, who doesn't cross-dress, but has a long hair and wears feminine clothes and make-up, has often been in danger of getting beaten. Luckily for him, there's usually been me or some other friends around to stop this. One time, however, when he was alone, he was beaten up outside a bar by skinheads. After that, I have also been wary of walking alone while wearing feminine clothes and/or make-up.

― Tuomas (Tuomas), Monday, 11 August 2003 14:05 (twenty-two years ago)

i often dress as marc bolan. i'm not sure if it really counts tho, cos he's pretty femmey. andrew you make a pretty lady.

http://www.geocities.com/lucylurex/bolan2.txt

hope that worked.

― The Lady Ms Lurex (lucylurex), Monday, 11 August 2003 19:40 (twenty-two years ago)

Goddamn, now there's the Jeepster! :-)

― Ned Raggett (Ned), Monday, 11 August 2003 19:47 (twenty-two years ago)

I fantasize none to seldom about xdressing, which includes glamming it up w/ makeup properlike. I haven't the faintest about makeup application, hence the "fantasize." Definite kink involved, anyway.

― Leee (Leee), Tuesday, 12 August 2003 04:27 (twenty-two years ago)

Erm, you could ask for someone else to do it. I'm not good at make-up either, but that's never stopped me. When we had the Finnish equivalent of Prom Dance at high school, I had a white suit and Valentino make-up done by friend of mine, and I looked dazzling (well, better than I usually look, anyway).

― Tuomas (Tuomas), Tuesday, 12 August 2003 12:40 (twenty-two years ago)

I was 8yrs old when i agreed to sub for my sister after she fell down the back porch stairs and fractured her leg the day before a figureskating show. My cousin and sister were doing a pairs number that I knew very well because I was my sis's practice partner all summer. I didn't want to but my mom and aunt and the rest of the family begged me until I agreed. Fortunately the skating dress and tights fit perfectly and I didn't have to wear any make up or anything. My mom and older sister worked on my hair to make it look bushy and made my eyebrows darker with a pencil of some sort. When I looked in the mirror my stomach started to spin and I got all red and tingly. Everyone laughed a little and encouraged me by saying I looked beautiful and that no one would look twice once we were at the rink. Once we got out of our apartment and onto the sidewalk, the feeling of the wind on my tights covered lege and the skirt swirling and rustling aginst me got my heart pounding and a rush of adrenaline that had me on pins and needles the rest of the day. The show turned out great, and everyone we knew there said I had more guts them anyone they ever knew and that I looked awesome as well. I had more fun that day dressed in that skating dress then I had ever experienced before and my mom let me stay dressed the rest of the day. I enjoyed wearing skating dressed so much that my mom and sisters let me wear their practice dresses and tights until I was about 14 and started to out grow my sisters in size. My older sister Janine who was in college, came home for Christmas the next year with a beautiful black Danskin sleeveless skating dress with a v neck and a pair of Danskin toast colored tights for my X-mas present saying that she knew I was secretly wishing for one. We all laughed when we opened our gifts and everyone saw mine. Naturally I couldn't wait to put it on and model it. When I did, the sensations were every bit as intense as I remembered. I still wear a skating dress and tights when I rollerblade along the lakefront paved trails here in Chicago. And I still don't wear make-up. I have years worth of pics for those interested.
Thanks for giving me a forum to tell my story. Jacky

― Jackie Kolodnicki, Tuesday, 12 August 2003 15:38 (twenty-two years ago)

I had to read the start of that sentence several times before I realized -- by getting to the end of it -- that "sub for my sister" didn't mean what it might've meant.

― Tep (ktepi), Tuesday, 12 August 2003 15:40 (twenty-two years ago)

To be honest, I have clitoris envy.

― Leee (Leee), Tuesday, 12 August 2003 16:15 (twenty-two years ago)

only once for halloween but i really enjoyed it. i was an older lady but i had quite a nice rack for a grandma

― ron (ron), Tuesday, 12 August 2003 23:11 (twenty-two years ago)

di is either (a) marc bolan; or (b) slash. i suspect the former.

― Tad (llamasfur), Tuesday, 12 August 2003 23:15 (twenty-two years ago)

To be honest, I have clitoris envy.

*blink*

Thanks. I needed to read that.

― I'm Passing Open Windows (Ms Laura), Wednesday, 13 August 2003 02:44 (twenty-two years ago)

If this Jackie person is for real (I'm not so sure about it), that's one great story.

― Tuomas (Tuomas), Wednesday, 13 August 2003 09:17 (twenty-two years ago)

i doubt the authenticity when the name is spelt differently in the post & then the name. Still, those skating dresses..

― Pinkpanther (Pinkpanther), Wednesday, 13 August 2003 09:21 (twenty-two years ago)

My story is a true one and I would have added a photo or two as well but I don't know if it's possible. I think my masculine emotions were at the forefront when I signed my story. All I can say is that it's as exciting today as it was all those years ago. Thank god the thrill of wearing one of my skating dresses and tights to skate or blade in hasn't deminished.
Jacky

― Jackie Kolonicki, Wednesday, 13 August 2003 18:36 (twenty-two years ago)

six months pass...

I wore a womens one piece last year to the beach. It was hot!! I felt so sexy. Can you put a pic on here and should I?

― Speeds man, Saturday, 6 March 2004 06:00 (twenty-one years ago)

please no

― anthony kyle monday (akmonday), Saturday, 6 March 2004 06:33 (twenty-one years ago)

Please do! I just drank a chocolate milkshake and I feel the need to purge.

― Kenny Blankenship (Bryan), Saturday, 6 March 2004 06:39 (twenty-one years ago)

ah yeah one piece
http://archives.eyrie.org/anime/Artwork/one-piece.nami.jpg
not sure I'll watch the whole serie.
Or are you talking about that beautiful word that is *monokini*?

― Sébastien Chikara (Sébastien Chikara), Saturday, 6 March 2004 06:43 (twenty-one years ago)

I've been mistaken for being a girl on a couple occasions. Once by some drunk girl who asked me if I was a girl, and another time by some little children who thought I was definately a girl (I think I was wearing a purple shirt). I kind of like the idea of looking androgynous (which is a different thing from crossdressing), but I haven't really put much effort into doing it.

― A Nairn (moretap), Saturday, 6 March 2004 07:00 (twenty-one years ago)

I'm not really sure how to go about doing that either.

― A Nairn (moretap), Saturday, 6 March 2004 07:11 (twenty-one years ago)

When I had longer hair -- it was about down to my chin -- I would get called "ma'am" a lot, particularly in Walmart. Telephone solicitors call me "ma'am" all the time, too. I guess I speak in a generally higher register than most men, but I don't think I sound terribly feminine.

― Prude (Prude), Saturday, 6 March 2004 07:15 (twenty-one years ago)

yeah, I get the "ma'am" thing a lot too. That kind of bugs me, mostly cause that word sucks

― A Nairn (moretap), Saturday, 6 March 2004 07:17 (twenty-one years ago)

You're right, it's not a very nice sounding word. It implies a certain amount of dowdiness, too. If I'm going to be sexually indeterminate, I might as well be attractive, dammit!

― Prude (Prude), Saturday, 6 March 2004 07:20 (twenty-one years ago)

Any one know how to upload pics on here?

― Speeds Man (Speeds Man), Tuesday, 9 March 2004 02:06 (twenty-one years ago)

Yes.

― luna (luna.c), Tuesday, 9 March 2004 02:10 (twenty-one years ago)

That anime pirate whore has my hair.

― Allyzay, Tuesday, 9 March 2004 02:20 (twenty-one years ago)

How do you put pics on luna?

― Speeds Man (Speeds Man), Tuesday, 9 March 2004 03:13 (twenty-one years ago)

Thumb-tacks and Tylenol.

― Tep (ktepi), Tuesday, 9 March 2004 03:15 (twenty-one years ago)

See the FAQ, link at foot of page.

― Martin Skidmore (Martin Skidmore), Tuesday, 9 March 2004 11:39 (twenty-one years ago)

Boyle to thread!

― the bellefox, Tuesday, 9 March 2004 13:04 (twenty-one years ago)

three years pass...

that andrew was some kind o' somthin'

― That one guy that hit it and quit it, Thursday, 3 January 2008 11:28 (eighteen years ago)

How do you put pics on luna?
-- Speeds Man (Speeds Man), Tuesday, 9 March 2004 03:13 (3 years ago) Bookmark Link

― Dom Passantino, Thursday, 3 January 2008 11:34 (eighteen years ago)

In before LJ

― StanM, Thursday, 3 January 2008 13:24 (eighteen years ago)

dammit stan

― Just got offed, Thursday, 3 January 2008 13:52 (eighteen years ago)

hahaha

― HI DERE, Thursday, 3 January 2008 13:57 (eighteen years ago)

wow @ "Jacky"

― Tracer Hand, Thursday, 3 January 2008 15:17 (eighteen years ago)

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