Need help with some dressing details

[Paula Elizabeth]

Hi all!

I am a 56-year old straight MWM with a fantasy that I can finally live out.

I have crossdressed on and off since my teens, usually just in lingerie and just for my own gratification in the mirror. I used to get so jealous of my girlfriends with all of the sexy finery that women get to wear while guys just basically have underwear, sock, pants and shirts. Yes, dressing sharp is great but women just are so lucky to have so much beautiful, comfortable, and sexy attire to choose from. I have bought lingerie and dresses, worn them in private, purged for a while, then started over again. At my old office job I used to wear satin panties under my suit but that's as close as I got. I did go out with some lesbian girl friends while in college, but that was only on occasion and quite a few years ago! Otherwise Paula has just dressed in and stayed in the closet.

I totally purged a few years ago but fate has put me at that starting over point again.

In a few months I will have a business opportunity to be away from home for a couple of weeks, visiting Las Vegas for a trade show and then to a vendor's training session in San Jose. I have decided that it is time for Paula to finally go out on the town.

I have always loved the classic (retro I guess it would be these days) 50's housewife look. To that end, I have bought some dresses, lingerie, shoes, and accessories on eBay. I am putting together some complete outfits for a few glorious nights out. I know the look that I want, I just need some suggestions on the correct finishing details.

My general accessories are: (earrings) pearl with a single pearl droplet, silver leaf dangles, gold hoops, diamond. (Necklaces) pearl, diamond, gold chain, silver chain. (Bracelets) pearl, silver charm, diamond. (Brooches) pearl flower and turquoise alligator. (Anklets) silver, gold, and diamond.

For shoes I have a pair of blue open-toe 2" pumps, matte black 2" pumps, black patent leather 2.5" pumps, black strappy 2" sandals, blue strappy 2" sandals. I have three purses, all evening clutch style, one black, one silver, one blue.

I am a natural red-headed ginger so have two red wigs, one straight shoulder-length (for a ponytail look) and one short with light waves.

I have two dresses, one mid-calf medium sleeve green polka-dot, one knee-length sleeveless blue. I also have a mid-calf denim poodle skirt with a long sleeve white and a long sleeve pink blouse.

I won't bore you with all the lingerie assortment, here are my planned outfits:

1 - (This is my prized outfit, the one I am oh so very looking forward to wearing) Green dress with pearl earrings, necklace, brooch, and bracelet. Silver anklet, black patent leather pumps, black clutch purse. Pink blush lipstick, eye shadow, and nails. Short wig with waves. My question is lingerie... Should I go with a simple white cami bra/lace panties/garter and very sheer white stockings. -OR- The same lingerie set in black. -OR- The same lingerie set in a pale green. I kinda think that all green is just too much. Maybe black or beige stockings instead with that option. I am kinda sorta leaning towards the white lingerie with beige stockings.

2 - Blue dress with either pearl or diamond accessories, blue strappy sandals or pumps, blue or silver purse. Red nails, medium red lipstick, pale blue eye shadow. The wig could go either short or long. Oh my, blue is just so easy to work with! My question again is lingerie... I have the bra/panties/garter/stocking set in light blue, white, and black. Any would work... Would all blue again be too much? Or just right?

3 - Blue poodle skirt with either white or pink blouse. Silver or gold accessories, blue purse, blue pumps, pink blush lipstick/eye shadow/nails... Would the white lingerie or black lingerie be best??

I have a few sexy sleepwear options that I -hope- to meet someone and exercise, but seeing as I am a virgin in that department, will have to see if my nerves hold out. I have never been with a man (and am not particularly attracted to them,) but I feel that if I am dressing as a woman, I should be with a man. I would consider a night with another TG or CD, but only as the submissive woman in the bedroom. If I'm going to be a lesbian, I want to be the pillow princess!

So those are my outfit options. I am open to any and all suggestions, comments, and constructive criticism... I just want to be as passable a woman as I possibly can and experience a few nights of being a woman. I want to walk that mile in a woman's shoes. I have 5-6 nights to go out and a few days to get all the makeup and nail polish removed and go back to just being plain ol' me before heading home.

For those who wonder, my wife knows nothing at all of "Paula" and would NOT be pleased, impressed, or accepting. I would be out on the street with no discussion.

Sorry for the length of my note, it's just that I am so excited to be able to go out as Paula for the first time since college. And to have a couple of weeks... I am as giddy as a schoolgirl at prom! LOL

Thank you ladies for all your help!

Hugs and kisses,
Paula Elizabeth Davis

[Thictoria]

Hi paula, if its the retro style your going for i would go for nude stockings as thats what they wore with white or black undies:)

[ReineD]

It depends on your ultimate goals: to be noticed and (likely) read, or to blend in and pass under people's radars.

If you don't mind being noticed, then by all means wear everything you've described. It sounds lovely! And it doesn't matter what lingerie is underneath, no one will see it while you are out in public. And believe me, guys don't pay attention to the color of your undies when sex is in the picture. So just go with what you love!

If you don't want to draw attention to yourself, I'd use a neutral eye shadow in earth tones and ditch the blue. The goal is to use light and shadow to give the illusion of reshaping your eye so it looks more feminine. You also might rethink the poodle skirt and I'd definitely use nude stockings with all your outfits. I would also wear the black shoes and purse with all your outfits, you don't want to be too matchy-matchy. Contrast provides interest. And the brooch ... do women still wear brooches? But this last one is just a minor point.

[DIANEF]

Hmmm, interesting post Paula. Your first line claims you are a straight man, but later you say that dressed as a woman you should be with a man, or even act like a lesbian(?), you sure your'e straight (I'm not judging BTW). I think your partner might be less impressed with this than finding out you CD. As for your clothes, sounds like a good selection, but what you wear may be secondary to how you look, how you act, how you hold yourself and how you interact with other people. (again, not judging..). Good luck with your trip.

[Rachelakld]

I just want to be as passable a woman as I possibly can and experience a few nights of being a woman.

Over here, the classical "house wife" look is long gone, wearing a brooch is like having a pokemon stuck on your nose, you will be noticed.
50+ women here try to look like 35 year old women, so trying to look like a 50+ will also get you noticed.
I'm still hoping for a "Rock n' Roll" or Elvis party as an excuse to dress like that

[Teresa]

Paula,
Some nice outfits, you will have fun but also stand out.

You may consider the first night just to blend and see how it goes, I know you're going to live a dream but it may turn sour if you have unexpected responses .

After a week it's going to be very difficult to stow it all away and go back to drab for any length of time, I can see a need to want more and it build up inside until you want to come out about it all. It is a pity that you feel you can't , I know what it's like but now I can get out socially it has brought a balance to my dressing. If you want to wear those outfits when meeting others no one will stop you, and you can enjoy wearing them to your hearts content, eventually you would find you would reach a balance .

[Jenniferathome]

Paula, I think it is far more wise to dress based on where you are going out. Even in Las Vegas people dress for the where. Lastly, no one wears a poodle skirt unless they are in costume. You write that you want to pass but nothing will attract more attention than being dressed from another time.

Plan your "where" and dress for that.

[NicoleScott]

Only you can resolve the conflict between your desire to pass and fulfilling your fantasy, if there is such a conflict. For many crossdressers passing IS the fantasy to be fulfilled, so no conflict. Killing two birds with one stone.
How about dressing to pass when you go out, and doing your fantasy dressing in private? So what if it takes two stones?

[BrendaPDX]

Paula, All these comments are right. Bring passable cloths to walk around in, people watch, see what you have or, go to a local thrift store and find something special that passes. It sounds fun, and I envy your time as Paula. Bring back some good stories and of corse pictures. Have a great time. Brenda

[docrobbysherry]

Paula, remember this when asking for fashion advice:

One picture is worth 15 paragraphs. And, even MORE!:daydreaming:

[Paula Elizabeth]

Thanks for all your comments!

When I received the poodle skirt and tried it on knew that wasn't going to work. Looks nice but like you said, would only work for a themed event. I am putting it back up on eBay. :) I did just buy a nice denim A-line skirt to replace it, it looks fantastic. Especially with the blue strappy shoes!

I don't mind being noticed or standing out in my dress, I mean, isn't that what we all really dress up for? I like the look and feel of the housewife look so will stick with that for my dresses. The skirt and blouses I'll dress a little more ordinary and blend in. As Teresa suggested, my first couple of nights will be very... modest... in a simple skirt and blouse... to get a feel for things before spending half an afternoon getting my dress and makeup just right.

Thanks for your thoughts, DianeF... That is something that I have struggled with a bit, just how far do I want to go with "being a woman"... As I said, if my nerve holds out, we'll see. I am just looking at this as my chance to just go all out, one big time. To "walk that mile" as a woman. Whether it includes a bi or gay or whatever interlude... I don't know. It would certainly have to be with the right person, who attracts me enough to give it a go. I'm not looking to just dress up and get laid, that certainly is NOT the point of this. I will just have to take it moment by moment and see where things lead me. As far as my wife, her attitude of me dressing would be that I would only be doing it to be gay, so sex and dressing would just be one in the same, and as I said, not even remotely tolerated by her. If I don't keep this totally out of her sight, it would certainly destroy an 18-year relationship.

ReineD, I guess I want a little of both. LOL From comments on here and other forums I've asked, I am changing my dressing up a bit. I am going with a simple all-white foundation with nude or white stockings for the dresses, when wearing one of my skirts will most likely match the bra to the blouse and stay with white panties/garter and nude stockings. I found a beautiful pair of blue strappy medium heels that look great with the skirts, I just need a purse to go with them now!! LOL Seems like I keep buying things to match things and then buy more to match that! I'm going to need an extra large footlocker to store all this stuff in! LOL

OH!! How long did it take you all to get comfortable walking in heels? I have a weak right ankle so stilettos or high heels are out of the question. Rolling my ankle off those heels would definitely ruin my night! All three pairs of shoes that I have are medium block heels (2"/5cm). I am spending a half-hour or so a day just walking around my shop in them to get used to them. I thought I sized my shoes correctly but they are a little loose. Some moleskin on the inside will fix that. I wear a 9-1/2 wide in men's, every chart I've seen translates that to an 11 wide in women's. I did try an 11 normal width but that was too tight. I haven't seen any half sizes past 10-1/2... I'm looking more at strap or slingback pumps now since I can tighten up the strap to keep them from slipping on my feet. Thoughts on that?

I will post pics of the clothes I have bought so far, as you have said, a pic is better than a description! No pics of me yet, still have some hair issues to get rid of. I want you all to see me as a woman, not as a guy in a dress, you know? :)

Thanks again ladies!!
Hugs and kisses,
Paula

- - - Updated - - -

OK, here are my dresses. I have not purchased the red one -yet- but am thinking hard about it. :)

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[Paula Elizabeth]

Here are my skirts and a couple of blouses...

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[Krisi]

..........For those who wonder, my wife knows nothing at all of "Paula" and would NOT be pleased, impressed, or accepting. I would be out on the street with no discussion.........

I am left wondering, if your wife doesn't know and would not approve, where are you keeping all these clothes, wigs, etc.?

I didn't see a mention of breast forms or hip/butt padding. Without these, you won't get far as a woman regardless of the outfits. I hope you have the good time you're looking for but I would be selecting clothing that fits in with what women are wearing where you will be. Buy stuff off the rack at Kohls or JC Penny and you will be on the right track.

[Jenniferathome]

Just two comments Paula:


...I don't mind being noticed or standing out in my dress, I mean, isn't that what we all really dress up for?...

No. "We" do not dress for this reason. "Some" do.


... As I said, if my nerve holds out, we'll see. ... Whether it includes a bi or gay or whatever interlude... I don't know. ... As far as my wife, her attitude of me dressing would be that I would only be doing it to be gay, so sex and dressing would just be one in the same, and as I said, not even remotely tolerated by her. If I don't keep this totally out of her sight, it would certainly destroy an 18-year relationship....

So how do you think having an extramarital sex would affect your relationship? Better or worse than telling her you cross dress? I suspect that discovery of you having gay sex would be even worse.

[Jamie Erikson]

I'm in much the same boat as Paula, except my wife knows that my ears are pierced although she perfers I don't wear earrings around her.

I have a few places at home where I store my ladies stuff.

[JenniferMBlack]

If you want to stand out in Las Vegas wear those outfits

[Paula Elizabeth]

Hi again all and thanks for the comments!

Krisi, I live in a deed restricted neighborhood so I am "forbidden" to work on my car in my driveway. I have a nice shop about a half-mile away that I have set up a small office and workshop in. I have a nice cedar wardrobe that stores away all of Paula's clothes and accessories. It's about 60' long so I have enough room to put on my heels and practice walking. It is not air conditioned so I can't dress there, no way am I going to get my clothes and finery all sweaty!

I didn't mention the silicone accessories before but I do have two pairs of breast forms. I started out with a C but it just didn't look right so bought a pair of D. I like the way they fit in my bra and like the way my clothes hang off them. My wife teases me that I "have no ass" so have some silicone hip pads, too

By the way, I am 6', 220 pounds. My dresses are 22W, 44-46 C/D bra, and 3x lingerie. I do have a below the breast corset but it is a bit too tight. I'm trying to drop another 10 pounds and with the corset I think I can manage a more girly figure. I need to lose a bit of the "6-pack" abs anyway so this is a win-win. My ears aren't pierced and all my earrings are either clip-on's or magnetic.

Thanks again, all!
Hugs and kisses!
Paula

[Alice_2014_B]

That blue dress!
Where did you find that!?
That is my choice, hands down!
:)

[Krisi]

If you are 6', 220 pounds, you should model your choice of clothing, hair and shoes on what "big" girls would normally wear. You will find that women that size tend to dress more conservatively than those who are 5' 4" and 120 pounds.

Also, isn't there a chance that your wife might drop in on you at your shop sometime and catch you dressed?

[reinasblack]

Visit Amy at Glamour Boutique (Just for you)and get a makeover.
You will love the way you look after

[docrobbysherry]

Paula, I hope u won't be offended. But, u mention not wanting to "look like a man in a dress" as the reason u don't post pics of yourself. Then, u post pics of outfits from the 50's/60's and say u r 220 lbs.

Let's start over. I think u should dress the way u like in the outfits u like, in private. And, if u like the way u look, that should be all that matters!:daydreaming:

But, if u post pics of yourself here or go out dressed like that, that's entirely different. Because folks will tell u what they think here. And, u can tell by the raised eyebrows, gaffaws, and the, "OMG! That was a man"s, when you're out that others don't see what u do in your mirror!:eek:

[ReineD]

I don't mind being noticed or standing out in my dress, I mean, isn't that what we all really dress up for?

Not really, unless you have the body of a hot 30 year old and the age to match. :)

Seriously, the more noticed you are due to your clothes, the more time an onlooker has to also notice that you are indeed a male who is dressed as a female. That said, most people keep their opinions to themselves and if you stick to well-lit areas with plenty of people around, you don't need to worry about your safety. Still, it all depends on how many people you wish will read you as a male. If you don't want to be read immediately, then dress a little more under the radar and by this I mean try to dress like the other GGs present.

I'm glad you've ditched the poodle-skirt, although this would be great fun at a 1950's party.



As far as my wife, her attitude of me dressing would be that I would only be doing it to be gay, so sex and dressing would just be one in the same, and as I said, not even remotely tolerated by her. If I don't keep this totally out of her sight, it would certainly destroy an 18-year relationship.

Then wouldn't a potential hook-up with anyone (whether they are male or female) chance destroying your relationship? And wouldn't you feel guilty about lying to your wife?



By the way, I am 6', 220 pounds. My dresses are 22W, 44-46 C/D bra, and 3x lingerie.

Given your body type, I wouldn't go for the dark blue, boat-neck dress. The green and floral are fine, and are good to wear during the day. The red is best at night and is appropriate for your age and size.

And all the skirts and blouses are good.

[Paula Elizabeth]

Paula, I hope u won't be offended. But, u mention not wanting to "look like a man in a dress" as the reason u don't post pics of yourself. Then, u post pics of outfits from the 50's/60's and say u r 220 lbs.

I haven't posted any pics of myself because, well, I don't have any! I hope to remedy that at some point and then will post the best one on my profile. :)


Krisi, I don't dress in my shop because there is no air conditioning and I don't want to turn my clothes into a sweaty mess. I only practice walking in my heels. With the door shut and locked. Should wifey drop by, it would be easy to ditch the shoes and answer the door.

Reine, I already have had to come to grips with the "guilt" of hiding Paula from my wife. Everything else just has to go with it. Thanks for the thought on the blue dress... I love it but wasn't sure about it. The picture has the bottom flared out a lot more than it really is but being sleeveless and boat neck... I'm a little afraid of it... My plan was to wear the skirts to hit the casinos, maybe an early dinner, then change into one of the dresses and go see a show. Maybe later go to one of the local bars just off the strip. I don't have plans yet for San Jose, I still need to get online and find what and where I want to do. I like the red dress but was going to pass on it, I'll get it now and look for another like it since you think that would suit me better. Thanks! :)

A few comments have been made about dressing or trying to look younger. I'm 56. I don't really see myself trying to look like anything other than a middle-aged woman. I think it would be easier for me simply look my age than to try and shave the years off with makeup or clothing.

And for the couple of you who sent me notes of support in PM, thank you!

Thanks again all for your thoughts and comments!
Hugs and kisses,
Paula

[reinasblack]

Body of a 30 year old Please!

A Body of a 21year old.
Even 23 in Bunny years is up there.