cross-dressing and how to do it

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I decided a couple-few weeks ago that I should go in drag this Halloween. Then" Joe Namath in panty hose" ad came up on the Mad Men thread, and I thought, "I have legs like that!", and last night I dreamed I made out with Eddie Izzard. The universe is telling me something. This must be done. I did it once before, years ago, and to rather stunning effect if immediate reactions are to be believed. But I'm a 35-year old man now, with stubble that needs a lot of regular maintenance, and my body, while having not gone completely south, is not the taut skinny little thing it once was.

What I don't want to do is put on a dress and look like it's powderpuff day in high school. I want to be *pretty*. Even sexy, if at all possible. I don't want to be a man in drag, I want to be a girl for the night. If that makes sense.

Any tips? Makeup I should use? Stockings I should prefer? Places to purchase a bustier? I want to look so good that I won't even need a wig. Though a wig isn't out of the question.

kenan, Tuesday, 7 September 2010 22:39 (eight years ago) link

smh

common ppl (Whiney G. Weingarten), Tuesday, 7 September 2010 22:40 (eight years ago) link

What? You don't think I can be pretty? I'll prove you wrong.

kenan, Tuesday, 7 September 2010 22:41 (eight years ago) link

:DDDDDDDDDD

acoleuthic, Tuesday, 7 September 2010 22:41 (eight years ago) link

do the full-body shave and the rest will come naturally

acoleuthic, Tuesday, 7 September 2010 22:42 (eight years ago) link

I am sure I have already seen a picture of Kenan dressed as an attractive woman somewhere on ILX.

I am using your worlds, Tuesday, 7 September 2010 22:42 (eight years ago) link

xp I'm none too hairy to begin with, so check.

kenan, Tuesday, 7 September 2010 22:43 (eight years ago) link

fwiw I want to do this properly, preferably onstage for my band

acoleuthic, Tuesday, 7 September 2010 22:43 (eight years ago) link

sudden disinterest in seeing LJ's band

Les centimètres énigmatiques (snoball), Tuesday, 7 September 2010 22:44 (eight years ago) link

good - sort the broad-minded sheep from the humdrum goats

acoleuthic, Tuesday, 7 September 2010 22:46 (eight years ago) link

You promised innovative new music, but it's been done before!
http://blogs.villagevoice.com/dailymusto/Images/some_like_it_hot.jpg

Les centimètres énigmatiques (snoball), Tuesday, 7 September 2010 22:51 (eight years ago) link

Nobody's perfect.

kenan, Tuesday, 7 September 2010 22:56 (eight years ago) link

*reads first post and immediately starts believing in God again*

Christine Green Leafy Dragon Indigo, Tuesday, 7 September 2010 22:56 (eight years ago) link

I asked God already, and his advice was not only unhelpful and totally off-topic, but a little angry and threatening.

kenan, Tuesday, 7 September 2010 23:02 (eight years ago) link

"Thou shalt not mix plaids with stripes!"

Christine Green Leafy Dragon Indigo, Tuesday, 7 September 2010 23:04 (eight years ago) link

Actually, that SHOULD be in the Old Testament. An oversight, imo.

kenan, Tuesday, 7 September 2010 23:09 (eight years ago) link

I was trying to think of the makeup that's used to cover up scars and such, and a quick google reveals that it is commonly used by transvestites: Kenan, the Rose beige seems like it would be most suitable for your skin tone. You can get smaller sizes muuuch cheaper on eBay. here's a color chart:

http://www.dermablend.com/foundations/foundations-severe-flaws/new-cover-creme.htm

I have false eyelashes and eyelash glue. You already have enviable eyelashes, but false ones would be even more fabulous. I've got the rest of the eye makeup covered, of course. There are tons of makeup tutorials on YouTube, and I'm sure there are some on transvestite makeup too–you will probably need one for dermablend, since that stuff seems like spackle.

JuliaA, Friday, 10 September 2010 17:38 (eight years ago) link

aw I hope you two continue your discussion on ILX

acoleuthic, Friday, 10 September 2010 17:46 (eight years ago) link

I had ludicrously long eyelashes for a man. I think just some mascara would be enough. I mean, right? My eyelashes brush against my glasses when I blink as it is.

kenan, Sunday, 12 September 2010 01:07 (eight years ago) link

i HAVE, I mean. I didn't lose them in an accident or anything.

kenan, Sunday, 12 September 2010 01:08 (eight years ago) link

RIP kenan's beautiful eyelashes

I am guessing they got etaen by geese accident

Mormons come out of the sky and they stand there (Abbbottt), Sunday, 12 September 2010 19:29 (eight years ago) link

They are totally still there. Well, mostly.

http://i72.photobucket.com/albums/i191/fluxion23/eyelashes.jpg

when you've got a fist all ur problems look like faces (kenan), Tuesday, 14 September 2010 00:32 (eight years ago) link

kenan's death mask!

Mormons come out of the sky and they stand there (Abbbottt), Tuesday, 14 September 2010 00:34 (eight years ago) link

Oh I hope I get a little older before it comes to that.

when you've got a fist all ur problems look like faces (kenan), Tuesday, 14 September 2010 00:37 (eight years ago) link

you need to consider shoes! shoes are important. your choices will depend on how large your feet are, how manly your feet look, and how comfortable you are with the idea of walking in heels.

tangelo amour (elmo argonaut), Tuesday, 14 September 2010 15:57 (eight years ago) link

It's a lot easier to find large-size and wide woman's shoes than it used to be, because people's feet have gotten larger. (Garbo was notorious in her lifetime for having big feet. She wore a size 8.) Kenan, what were you planning to wear? Long dress, short dress, pantsuit?

Christine Green Leafy Dragon Indigo, Tuesday, 14 September 2010 16:03 (eight years ago) link

fwiw i have a size 10.5 foot but iirc women's sizes are (men's size + 3) so when i did this i had to look for a size 13.5 and there's not a whole lot of sexy footwear in that size range unless you want to spend $$$. i had to settle for squeezing into a size 11 women's open-back shoe which was kinda painful / hilarious / grotesque

tangelo amour (elmo argonaut), Tuesday, 14 September 2010 16:03 (eight years ago) link

but yknow i was dressed in outrageous grandma drag so my goal wasn't "sexy" really -- the overall look was described by some as "like Tyler Perry as Medea, but white"

tangelo amour (elmo argonaut), Tuesday, 14 September 2010 16:08 (eight years ago) link

I think women's sizes are actually men's +2. But the only thing I tend to see made in 11+ that's $50 or less are straight up stripper heels. (example)

Mormons come out of the sky and they stand there (Abbbottt), Tuesday, 14 September 2010 16:16 (eight years ago) link

omg can we have a sub-discussion on stripper shoes, because they are hilarious

and by "Heavens!" i mean WATERFALLS OF BIDDY (HI DERE), Tuesday, 14 September 2010 16:19 (eight years ago) link

drag is a thing that makes me wish i was a tinier person.

tangelo amour (elmo argonaut), Tuesday, 14 September 2010 16:20 (eight years ago) link

kenan you should get these:

http://www.fantasiawear.com/ImagesShoe/ps8230.jpg

along with a bunch of audio cassettes to crush

tangelo amour (elmo argonaut), Tuesday, 14 September 2010 16:23 (eight years ago) link

It's still heels for long skirts and flats (or low heels) for short, right?

Christine Green Leafy Dragon Indigo, Tuesday, 14 September 2010 16:34 (eight years ago) link

Elmo if you're ever in need of sexy lady shoes to feel man sized feet I'd head to Dorothy's on Mass Ave near Berkley: http://www.dorothysboutique.biz/

master of retardment (ENBB), Tuesday, 14 September 2010 16:40 (eight years ago) link

i wore a short dress with heels the other night and felt pretty fancy

peacocks, Tuesday, 14 September 2010 16:52 (eight years ago) link

is there a rule about that kind of thing?

peacocks, Tuesday, 14 September 2010 16:52 (eight years ago) link

haha, thx E! (tho i'm not sure i'm gonna do drag this year again -- i may just re-use my dionysos costume from this summer)

tangelo amour (elmo argonaut), Tuesday, 14 September 2010 16:53 (eight years ago) link

is there a rule about that kind of thing?

Don't tell me, this is yet another of the rules that I was raised on that everyone else stopped going by years before I was born.

Christine Green Leafy Dragon Indigo, Tuesday, 14 September 2010 16:58 (eight years ago) link

fwiw Abbott is correct re: sizing difference

tangelo amour (elmo argonaut), Tuesday, 14 September 2010 17:17 (eight years ago) link

Off-topic, sorry, re flats v heels etc: There's no rule anymore really, it's harder than that, cos it's about proportion and your body and overall image, ie with something tight and oh say '50s sex-kitten-ish, some pointy little heels (maybe even dainty?) will probably go better than flats. Yr skin-tight American Apparel hipster leggings probably look kinda slutty with heels, better w flats.

Otoh it's true that no one get-up needs all the va-va-voom while other outfits get none, so sort of...pick one or maybe two "hot" item(s) per outfit and adjust everything else to accentuate/contrast.

Q: What's small, clumsy, and slow? A: A toddler. (Laurel), Tuesday, 14 September 2010 18:25 (eight years ago) link

OTM

master of retardment (ENBB), Tuesday, 14 September 2010 18:42 (eight years ago) link

I had a friend who went to SF in high school with the goal of getting some stripper heels to fit his size 11 feet. He did not know the +2 size difference and bought some size 11W when he should have bought some size 13W. They looked like these:

http://www.fantasiawear.com/ImagesShoe/pssky309z-black-shoe.jpg

I had the first Elric novel, he wanted & he convinced me to trade the shoes for them. I went over to his house & we were going to play video games together but he said I had to wear the shoes while I did. This was a highly socially awkward night.

Now my sister wears the shoes when she vacuums her apartment...she is 5'11" top begin with so this is some serious Amazon vacuuming.

Mormons come out of the sky and they stand there (Abbbottt), Tuesday, 14 September 2010 20:46 (eight years ago) link

I should say, he was going to SF for some school thing, and his secondary goal was to attain stripper heels.

Mormons come out of the sky and they stand there (Abbbottt), Tuesday, 14 September 2010 20:47 (eight years ago) link

Vacuuming in heels is some serious amazon behavior at any height. Hubba hubba!

bamcquern, Tuesday, 14 September 2010 22:13 (eight years ago) link

Where to go in Chicago

Olde Executioner 8hundo (Eazy), Wednesday, 15 September 2010 05:07 (eight years ago) link

xp - what? how is that amazonian? i can see if you had to lift the vacuum over your head or something - or if you were converting the vacuum into a rocket - but just pushing the thing around the rooms of your standard tract home - does not require much effort at all.

sarahel, Wednesday, 15 September 2010 09:30 (eight years ago) link

No it's just that in the heels she'd like 6'6". I am sorry I did not mean she was literally doing vicious one-breasted warrioress activities.

Mormons come out of the sky and they stand there (Abbbottt), Wednesday, 15 September 2010 16:10 (eight years ago) link

Damn.

Christine Green Leafy Dragon Indigo, Wednesday, 15 September 2010 16:28 (eight years ago) link

she had a mastectomy too?

sarahel, Wednesday, 15 September 2010 16:43 (eight years ago) link

No, I did not mean that. Once again, apologies.

Mormons come out of the sky and they stand there (Abbbottt), Wednesday, 15 September 2010 17:54 (eight years ago) link

Hey, pick your pleasure.

I think I really dug the outfit.

when you've got a fist all ur problems look like faces (kenan), Thursday, 16 September 2010 00:36 (eight years ago) link

Haha I looked up "Altawoman" because of that article and it has some great selective pull quoting.

"....the most balls-out
transformations of all time!"
"... the transformation scenes are
detailed and hot!
Neal Pollack of Nerve.Com
It cuts off the start of the sentence: "The site is stupid almost beyond imagination..."

Mormons come out of the sky and they stand there (Abbbottt), Thursday, 16 September 2010 00:40 (eight years ago) link

Uh that Altawoman link is NSFW for what it's worth.

Mormons come out of the sky and they stand there (Abbbottt), Thursday, 16 September 2010 00:41 (eight years ago) link

Fifteen years ago, the fetish communities were the Internet's best source of original fiction, and the transformation people were at the top of the list. I don't know how much of it has survived, though.

Christine Green Leafy Dragon Indigo, Thursday, 16 September 2010 01:34 (eight years ago) link

six months pass...

I have realized lately that I have a real thing for cross dressers. I want to see Kenan dressed up. PICS, PLEASE.

homosexual II, Monday, 4 April 2011 17:50 (eight years ago) link

http://farm5.static.flickr.com/4015/5139040138_b60eccbce3_z.jpg

i made the earrings (it's something i do), and did his fabulous makeup, which we didn't get good pics of, sadly.

JuliaA, Monday, 4 April 2011 18:03 (eight years ago) link

<3

homosexual II, Monday, 4 April 2011 20:59 (eight years ago) link

I wish I had more occasions to cross dress, I honestly do. It's not that it has to be Halloween, or that I need a particular excuse, I just hate the feeling of being all dressed up and having nowhere to go.

DSMOS has arrived (kenan), Thursday, 7 April 2011 22:33 (eight years ago) link

You can do it whenever! It doesn't have to be Halloween. You just need to find a CD-friendly event, like maybe a gay club or a goth dance night or something. I see CD's all the time when I am out.

homosexual II, Monday, 11 April 2011 17:33 (eight years ago) link

I know you say you don't want to do Drag - but watch a couple of episodes of RuPaul's drag race. Pantyhose! Colour blocking on the cheeks! Cutting up sofa cushions to create perfect derrieres! I have picked up a few makeup tips from watching the queens. Of course I wear it a little more subtly, so that at 6'1" I am not mistaken for a biological man..

she started dancing to that (Finefinemusic), Monday, 11 April 2011 18:04 (eight years ago) link

That's such a great picture. Such pretty animals, all of us.

DSMOS has arrived (kenan), Wednesday, 13 April 2011 20:42 (eight years ago) link

FYI, manda, that pic is now on my office wall, right between Julia and Calvin and Hobbes. People find it very creepy. I find that delightful.

DSMOS has arrived (kenan), Saturday, 16 April 2011 02:15 (eight years ago) link

I'm ok with that. Glad to contribute, even :)

housedress? maxidress! (La Lechera), Tuesday, 19 April 2011 04:21 (eight years ago) link

two years pass...

Does ilx have a thread about female masking? I've looked but I can't find anything.

https://www.youtube.com/watch?v=Tf1DFXWi7GM

https://www.youtube.com/watch?v=fNDk0mpkpRQ

squeak and gibber (Eight Model Play), Wednesday, 14 August 2013 11:27 (five years ago) link

That is the meditation when one is alone: to love oneself so deeply that for the first time you become your own love object.

So in these days when you are alone, be a narcissist; love yourself, enjoy yourself, delight in your body, in your mind, in your soul. And enjoy the space that is empty around you and fill it with love. The lover is not there -- fill it with love! Spread your love around your space, and your space will start becoming luminous; it will glow. And then for the first time you will know

squeak and gibber (Eight Model Play), Wednesday, 14 August 2013 11:43 (five years ago) link

why did whiney post "smh" ?

flopson, Wednesday, 14 August 2013 23:48 (five years ago) link

good - sort the broad-minded sheep from the humdrum goats

― acoleuthic, Wednesday, September 8, 2010 8:46 AM (2 years ago) Bookmark Flag Post Permalink

<3

estela, Wednesday, 14 August 2013 23:52 (five years ago) link

I feel like this is something I'm interested in. Been wearing random women's garments that fit a more masculine style (jeans, hoodies, etc) sometimes lately but I'm considering taking it to the next level

s. cloverlandthug (The Reverend), Saturday, 24 August 2013 08:10 (five years ago) link

I'd be interested to know how that works out for you. I'm working through some gender-identity questions I'd had to put aside because, well, Alabama, but I've been able to start dressing and presenting myself a bit more comfortably over the last few years (growing my hair out, getting my ears pierced, trying to avoid obvious gender cues or at least masculine signifiers where I can) and it's made a huge difference in my ability to feel okay in my own skin.

CAROUSEL! CAROUSEL! (Telephone thing), Sunday, 25 August 2013 06:18 (five years ago) link

that's totally where i'm at too! i've been into the androgynous look for a while, and i think it's really hot when guys pull it off. my hair's almost down to my shoulders now. not sure if i want to go for the whole look or just "pretty boy" but it's really -important- to me for some reason.

chilli, Sunday, 25 August 2013 21:12 (five years ago) link

I have to be kind of conservative because I just turned 30. I look young for my age, apparently (maybe some small karmic payback for missing basically the entirety of my teens and 20s, more likely just due to avoiding things like sun exposure and drinking heavily and fun) but I have to think long-term now. There's a little leeway to experiment while I go back to school, but I'm kind of scared it's too late to figure this out.

CAROUSEL! CAROUSEL! (Telephone thing), Sunday, 25 August 2013 23:18 (five years ago) link

two weeks pass...

Got mistaken for a girl tonight in a fairly neutral outfit, even though I'm 6 foot and 155 pounds. It's still nice, though; that along with pretty much everyone I interact with being cool with my stupid gender identity shit (whether stated or not) and the discovery of a trans*-friendly unisex bathroom at my school (at a fucking community college, even) makes me wish I'd moved to this part of the country, or I guess to 2013, ten years ago, if not more.

CAROUSEL! CAROUSEL! (Telephone thing), Friday, 13 September 2013 03:56 (five years ago) link

Thread of missing Kenan.

Jeff, Friday, 13 September 2013 11:55 (five years ago) link

Thread of missing Kenan.

Jeff, Friday, 13 September 2013 11:55 (five years ago) link

No idea why that posted twice. I don't miss him that much. Only once.

Jeff, Friday, 13 September 2013 11:55 (five years ago) link

Facebook has all the thoughts and photos you need.

bad bad disco (Eazy), Friday, 13 September 2013 13:52 (five years ago) link

one month passes...

I painted my nails a few days ago but now they're all chipped to hell. >_<

old homophobic boom bap rap traditionalist (The Reverend), Wednesday, 16 October 2013 02:09 (five years ago) link

You should use topcoat too

she started dancing to that (Finefinemusic), Wednesday, 16 October 2013 02:13 (five years ago) link

Try Seche Vite top coat next time. And clean your nails with nail polish remover first to make sure there's no oil on your nails. That will help the color stick longer.

carl agatha, Wednesday, 16 October 2013 02:15 (five years ago) link

Haha xp

carl agatha, Wednesday, 16 October 2013 02:15 (five years ago) link

seche vite = gamechanger

set the controls for the heart of the sun (VegemiteGrrl), Wednesday, 16 October 2013 02:17 (five years ago) link

My new fave topcoat actually is Sally Hansen's Hard as Nails fwiw.

Tottenham Heelspur (in orbit), Wednesday, 16 October 2013 02:25 (five years ago) link

That's the one I use. It's amazing! Couldn't find SV easily here.

she started dancing to that (Finefinemusic), Wednesday, 16 October 2013 02:26 (five years ago) link

SV goes on like the nectar of the gods, but it shrinks back from the edges on the 2nd or 3rd day, depending on the exact formulas of the polishes underneath. The Hard as Nails is almost as glossy as SV but seems less inclined to pull away.

Tottenham Heelspur (in orbit), Wednesday, 16 October 2013 02:41 (five years ago) link

two weeks pass...

I bought the most adorable little dress for $5 that I'm going to wear out tonight! I'm gonna have to wear the girl jeans I already have (or maybe my skintight black men's skinny jeans?) under it cause it's too short/sheer to wear without something under and I don't have anything else suitable. Also gonna paint my nails again & wear lip gloss. It'll be so cute.

old homophobic boom bap rap traditionalist (The Reverend), Thursday, 31 October 2013 20:25 (five years ago) link

pics

ͼѾͽ (sic), Friday, 1 November 2013 03:10 (five years ago) link

^^^

set the controls for the heart of the sun (VegemiteGrrl), Friday, 1 November 2013 03:45 (five years ago) link

kate78 ended up hooking me up with some accessories

https://scontent-b-sjc.xx.fbcdn.net/hphotos-prn2/603081_10201345115244618_1819216073_n.jpg

old homophobic boom bap rap traditionalist (The Reverend), Friday, 1 November 2013 20:05 (five years ago) link

That's a good look!

carl agatha, Friday, 1 November 2013 22:11 (five years ago) link

...and a screwdriver. xpost

kate78, Friday, 1 November 2013 22:16 (five years ago) link

I love the way lanky men can sit with their legs crossed straight at the knee. I personally cannot. Just one of those things....

Tottenham Heelspur (in orbit), Friday, 1 November 2013 22:17 (five years ago) link

I can't comfortably do that wearing jeans, wasn't uncomfortable with leggings though.

old homophobic boom bap rap traditionalist (The Reverend), Friday, 1 November 2013 23:12 (five years ago) link

I love the way lanky men can sit with their legs crossed straight at the knee.

I don't think I understand this- how else would you sit with your legs crossed?

omg rev so cute. love it!

set the controls for the heart of the sun (VegemiteGrrl), Saturday, 2 November 2013 01:05 (five years ago) link

xp My top leg points sideways and often slides off the bottom leg because I'm just built that way I guess.

Tottenham Heelspur (in orbit), Saturday, 2 November 2013 01:08 (five years ago) link

my legs are too thick to really drape the way laurel is describing

homosexual II, Tuesday, 5 November 2013 20:49 (five years ago) link


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