How to be a cross-dresser?

In My Humble Opinion
1

Holy cow what a doozy of a first post.

Here is the basic story. I’ve been in a long-term relationship with a wonderful woman for about six years. We’re stable, caring and very comfortable with each other. We’d better be. This post is a result of a long history of cryptic hints, veiled suggestions and otherwise hidden desires. Hmm… how much back story to include? Anything? Just enough? Everything? I’ll put in some in hopes that you won’t think I’m trolling and will take the OP seriously. Well, as seriously as one can take an OP looking for cross-dressing advice.

She is … is curious the right word? We’ve watched some adult movies together, and one of the bombshells she dropped was how turned on she got from watching two women together. Wow, thought I. I daresay just about every male reading this understands what I mean by “wow.” Other little hints and suggestions arose from time to time. But, being the “good girl” that she (thinks she) is, it all remained nicely tucked away in the confines of the bedroom. Nothing wrong with that, and it didn’t come up all that often. We have quite a vigorous sex life in other ways. But it seems she is moving a bit towards indulging that side of her.

The genesis for the OP came a few weeks ago. In a rather passionate moment, she asked me if I’d be willing to wear a wig (she has one from a Halloween costume) to bed with her. Of course, given the situation we were in at the time, I would have agreed to just about anything. There is the visceral pleasure of sex, the realm of physical sensations. Yea nerve endings! Ah, but there is also the mental realm. To me, nothing, nothing is a more powerful aphrodisiac/ turn on than the sexual excitement of your partner. The wonderful synergy of it is that that in turn gets me more excited, which feeds into her excitement… ah, wonderful feedback. Yea brain! So sure, I would have agreed to just about anything.

It has evolved since then, giving rise to the OP. She wants to come home (well, her original idea was to meet at a bar, but I don’t think I could pull this off that well) to a completely different me. Started off when I asked her if she’d like it if I shaved my legs… makeup was brought up, she mentioned stockings… soon we were talking about the whole nine yards.

So here is the OP (sorry for taking so long, but as I said I wanted to avoid being called a troll if possible). How the hell do I pull this off? (OMG that doesn’t sound right. There will be NO pulling things off. Ouch!) If I am going to do this, I don’t want to do it half-assed – I want to look like the best damned woman I can. Not that I expect to be an attractive woman, mind you, but I want to look as good as I can given the underlying sow’s ear. But how? I know dressing up is a skill – it takes her a while, and she’s been doing it for years. Is there any chance of me getting it remotely close the first time?

First, there are the sizes. I am NOT going to try things on in public, and I don’t expect to be able to explain all this to the friendly salespeople. I just want to walk into Payless, grab a pair off the shelf and hustle out of there as quickly as possible. But what size shoe? How do women’s sizes translate? What about stocking size? Dress/ skirt? Lingerie? I know her sizes, which makes getting those things easy, but I have no clue what to do. And where? I’m used to getting things at Victoria’s and whatnot, but I don’t think I want to invest that much into all of this.

OK, now that you’ve helped me get shoes, stockings, garters, (oh gee… should I get a bra? How the hell do I do that?! What do I put in it?! Hmmm… like I said I really want to do this as convincingly as possible, but maybe I should draw a line somewhere) some simple lingerie and a nice frock. Maybe someone’s even told me how to get the wig to stay on. The next step is makeup.

Now there is another one of those mysteries to guys. So I hit CVS and get … what? Well, obviously there is lipstick. Just grab any random color/ brand I can find? What the hell is eye shadow? I’ve heard of it but don’t know what it is for. Mascara? Another one of those mysteries to me… I’ve seen commercials with the pipe cleaner in the tube, but how do you put it on? I’ve seen her do it a thousand times but beats me what she is actually doing. What else do I need? What’s rouge for? What about ‘foundation’? What does a basic makeup kit consist of, what do you use things for, and how do you put them on?

Oh wait, before I get dressed, I should shower. Shaving my legs is one thing, that should be fairly straightforward and easy. But should I shave my chest? I’m not all that hairy, more Sean Connery than Austin Powers (when it comes to looks, reverse that). Well, would it make a difference? And facial hair? No matter how close I shave in the mornings, within an hour or so I don’t quite have five o’clock shadow but you can tell I’m a guy. Any thoughts on cleaning that up? Papier-mâché? Thick gobs of makeup? Or just shave as well as I can and deal with it?

So, is that it? Am I forgetting anything? ANY help, suggestions, or advice you have would be helpful. I must admit that as willing as I am to do this, I am a bit nervous. I am going to have a very hard time shopping for this without blushing like a madman (Oh yeah, what is ‘blush’ anyway? Do I need that too?) so anything you offer will be welcome. Anything you can say to help me look more like your basic female impersonator and less like a freakish mockery of femininity will be greatly appreciated.

Oh, I don’t know if it makes a difference or not, but I am about 5’11" and 150 lbs.

Wish me luck!

Boy Binkley

(Did anyone pick up on the Bloom County reference? Thought it would be an appropriate SN given my first topic. Anyone know where I can find the original series of panels online?)

2

Wow.

I’m not sure how to help you, but I just had to say that I think you win the “Interesting first post” contest. Welcome to the boards! You’ll fit right in.

3

I can help you a little bit. Men’s shoe sizes are two sizes off from women’s. A men’s 8 is a women’s 10.

I admire your -uh- dedication.

4

Another poster chiming in to welcome you to the boards. Your girlfriend’s a fortunate woman. You are just adorable!

5

Your SO is extremely fortunate to have someone as devoted to her as you are.

Some thoughts (none from experience, just some deductive reasoning):
[ul]
[li]Thicker makeup may cover or slightly hide the stubble. Could a bleach or dye work as well?[/li][li]Definitely shave everything within reach. Arms, legs, chest, nether regions.[/li][li]Maybe a not-so public but open place would be a good meeting place. A secluded park, parking garage, empty playground.[/li][li]Eye-sahodw is for the eyelids. Beyond that I’m clueless.[/li][li]Mascara thickens the eyelashes[/li][li]I don’t know anything about women’s sizes. Men’s clothing is so much easier since it goes by actual measurements.[/li][li]I’m sure some internet searches could turn up some more useful info.[/li][/ul]

6

Sure…it’s your wife’s idea. I believe you, really. My wife likes it when I download internet porn late at night while drinking beer. :smiley:

Seriously, I’m sure there are plenty of internet sites that can give you suggestions. I did a quick search of crossdressing and came up with a ton of sites (I’m at work so I didn’t open them). Also, I noticed in our weekly alt newspaper that there are specialty crossdressing ‘boutiques,’ and lingerie stores advertising plus & men’s sizes. I’m sure the on-line lingerie shops feature these also.

Welcome to the board and be sure and post before and after pictures.

7

Big index of how to apply makeup

Good luck. Welcome to the boards, and Bloom County rocks.

8

Wow! You are ONE FUN DATE! To buy the clothes, just tell the woman in the store you’re looking for something special for your wife and she’s about “my” size. Same with the lingerie. They’ll scope you out and hold stuff up to you, but it’s a gift for your wife.

Pay attention to detail. Paint your toenails. What a riot. Have fun!

9

For clothing sizes, you’re going to need a tape measure. Here is a size chart, and where/how to measure. I don’t expect that you’re larger than a size 18 at your weight, so you should be fine with this chart.
I think that you should go with a bra, mabe a padded or push-up bra that you don’t have to ‘fill’.
Here is bra sizing and measurement, because bust size and bra size are not the same thing.

You should probably get some perfume that you like, is subtle, and that is noticibly different than the perfume that she wears.

10

I notice that the big make-up link above has a good guide to choosing lipstick colors. That’s good.

Fake nails are easy to apply. Basically, you paste them on with super glue, and take them off with acetone nail polish remover (you soak in it). When you apply the fake nails, try to be careful to not get your skin at the tip and at the base. If the nail attaches there, the pressure from normal wear hurts.
I think it would be an excellent touch.

11

Brut?
Kudos to you for being able to think outside the box… waaaaaaay outside the box… to keep things lively.

12

Buy the clothes first, THEN choose the makeup. You don’t want to clash! Nylons are easy to buy - they have approximate S-M-L sizes based on your height and weight. Just read the back, and when in doubt, try the slightly larger size, since it’ll be sure to fit. They stretch somewhat, but too much and they shred.

Um…do you have a wig, or are you getting a new one? That might affect your makeup choices too.

I don’t know

  • good luck!
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Oh, and if you want someone to consult with about it, styles/colors/makeup/whatever, I’d be happy to help you. Just send me an e-mail.

14

women’s clothing size chart …go get a measuring tape and see what size range works best for you. You might fit better in Junior’s sized clothing because they tend to have less allowance for curves.

15

the women’s size chart I hope it works this time.

16

Wow, thanks for the help so far! I was a bit worried no one would take this seriously. As a contender for the “Interesting First Post,” let me say that I will only use my crown for good, love children and want whirled peas. I just realized that I had thought of posting to the Very Vaguely thread (a lot of people had their first OP there) and, well, from some viewpoints this whole thing might fit (Jesse Helms I’m looking at you!).

Ok, so shoe size sounds about the easiest to grab. Just add a couple sizes and there I am. As far as I know I won’t be trotting around much, so comfort won’t be an issue. But then again, the park idea sounds fantastic! In thinking about it, that means I’ll be able to pull off a total surprise. No worry about sitting in a bar afraid someone will come up to talk to me. How long does it take to learn to walk in heals?

I’ve never dyed my hair … bleach on my face? OUCH! Haven’t there been some threads in the past about getting rid of facial hair? All I can remember is that I DON’T want to go the Neet route. From what I saw in the E-How link (thanks! I love that site but didn’t think to look up makeup. Maybe X-dressing is in there too) lots of foundation or concealer will do the trick.

Another good suggestion to shave the arms and whatnot. (It will grow back I hope.) Nice touch. Perfume is another great idea. And fake nails and painted toes… it is fall so who else will see my feet? I thought about painting my fingers, but with short nails didn’t think it would fit so well. But with press-ons? Great.

Yeah, I wasn’t sure if I should post the OP or not, but I am sure glad I did – another great suggestion I wouldn’t have thought of is the same-size comment. “Her size? Oh, I don’t know, she is maybe an inch or two shorter than I, about 130. She wears my clothes all the time, if a bit long on her.” Dropping a couple inches and keeping the weight proportional keeps the dimensions roughly the same. I’ll be looking for a dress or whatnot so the height shouldn’t matter. This will clearly help me keep my composure and not worry that the salesperson is going to push the “weirdo” button. And with the size charts here I can run into Marshalls or whatnot to grab a simple frock without going overboard. Yea the SDMB!

The bra thing seems to remain somewhat of an uncomfortable problem. “Yes, she is about my size but has no chest, so I need a padded bra. Sure.” That will take some practice to say with a straight face.

I’ve done a small bit of poking on the net, but you can imagine the number and caliber of hits I’ve been getting. That and I can’t really go to too many places on this computer…

As for whose idea this was, I’ll admit I was wondering what was going on with the hamsters inside my head. First off, after reading the replies and thinking about where to go/ get, it is also beginning to feel a lot like Halloween. Especially like those times when you have a really good costume idea and you spend a lot of time planning it out. But of course, it is all about the sex. And sex is sex is sex is sex. This is going to blow her mind – which in turn is going to lead to one HELL of an evening.

I hope I don’t sound uxorious, but if something has a chance of making her happy, I’ll do it. Sure, there are limits, but this is wayyyy inside those. Her happiness spurs mine, and the reverse is true. Yeah, that sounds quite like the inside of a poorly written Hallmark card, but there is a lot more to it than that. Pick up Aristotle’s Nichomacean (sp?) Ethics. Basically starts with a definition of happiness. Catch phrase is ‘happiness is the activity of the soul in accordance with virtue.’ He builds on that, defining different virtues, their extremes and their center (i.e. cowardice – courage – rashness). Last section? Friendship. Highest virtue of man- to be someone’s friend. The virtue rests in the reciprocal nature of true friendship; one receives joy from the other’s happiness and vice versa. Same kind of feedback I was talking about in the OP – her figure, her looks, her physical touch is pleasurable, but intense eroticism stems from her own excitement. Yeah, it’s all about the sex.

Thanks for your help so far… this will be one HELL of an evening!

BB

17

uxorious

adjective- Excessively submissive or devoted to one’s wife
I learn something here everyday.

18

Nicomachean

Noun - the correct spelling of Aristotle’s Ethics.

SDMB … all about fighting ignorance and great sex.

19

If you are trying to indulge your wife’s interest in a semi-lesbian encounter, do NOT, repeat NOT, wear press-on nails.

20

To “nots”, both in all caps. Must be serious! But not to be pendantic about it, why not? Could it hurt her? Do real semi-lesbians not wear pressons?