Dressing My Age

[Martha]

I am 57 and around the house I dress very sexy with short skirts, thigh high hose, garters, and tight blouses. Underneath some lacey panties and a lacey thin bra. My wife wants to take me out to dinner for my first time out when it warms up outside. I know I should dress more conservative when out in public but the reason I wear women's clothing is to feel sexy. I don't want to dress like grandma. How sexy can grandma be? How can I look sexy, yet my age, and still have fun while out En Femme?

[Martha G]

I am 72. I try to dress my age but not like a grandma.

I make a very, very passable woman when dressed. I look 10 or so years younger. I feel that way as well.

I thoroughly enjoy dressing as and acting as a woman.

I enjoy wearing knee length or slightly above the knee skirts, pencil skirts and nice looking pants. I also have other length skirts as well.

I prefer skirts and pullovers and blouses.

I dress to look attractive and pleasant when out.

I have worn a miniskirt to a party but not out in general.

As I say, I am very passable as a woman but try not to draw too much attention.

Around the house anything goes. LOL!

[Davita]

Hi Martha,
Are you saying you want to look sexy while you are grocery shopping? Are you wanting to look sexy to attract a "playmate?" There is age appropriate and there is context appropriate as well.

Anyway, the adage if you got it flaunt it applies to all ages, but you don't do it the same way for all ages. Maybe the only exception would be legs. There are just two ways to show them off -- short bottoms or tight bottoms and the combinations thereof. If you have a nice figure, you can wear something snug without being form fitting like latex can be. Personally I think a woman who dresses smartly and shows she has a shape is sexy, but a woman dressing like she works downtown on the streets is just slutty. Look sharp with good fitting clothes that aren't extreme and go from there on how short is too short and how tight is too tight or how much sheer is too sheer. Sexy doesn't always mean you have to show more skin than not.

Look at women your age under different circumstances and see who's noticing them. As for me? I'm never going to be sexy, but I can still look good.

[Estefania]

Martha,

One thing to consider is if you will be attempting to be passing or even accepted as a woman or if you and your wife don't care for that and just want to go out wearing women's clothes you like, regardless to what people wear to the places you want to go to.

So if the goal is passing, you don't have to dress like a school marm. True, the older we get, the less people will question how we dress or how we look, wether dressed up as a guy or a woman. But you can bet a 60 yo female wearing fishnets and a micro-mini is going to be out of place in most places. People will not question her gender, but they will question her taste in clothes to say the least.

If you are off to dinner to a nice "Olive Garden"-like place, it will still be different if it is in NYC than, say, Tulsa. But at the end of the day, the only important opinions are yours, and your wife's. So I'd suggest... Since she is pretty much taking you out on a date... Why don't you check upon with her what she is planning to wear so none will be overdressed or underdressed for the place? Women do that all the time. (Checking what their friends will be wearing)

Have a good time!
Gaby

[Requal Jo]

Gaby certainly has given you a good answer to your question Martha. Women often talk between themselves about what they will wear and comment appropriately. As your wife has asked you out, ask her what she is wearing and complement your dressing with hers.

[Martha G]

I dress very smartly and nice.

I try to dress as an attractive mature woman.

No fishnets, stiletto, super short skirts or things like that. No overbearing makeup.

Though I do like knee length skirts.

I do have a very nice looking pair of legs.

I have been accepted as a woman when I am out. And that's what I want/ Not a lot of attention.

By the way I am single and straight.

Dressing as a woman relieves much stress and makes me look and feel much younger. I enjoy my feminine side.

[DonnaT]

Google images "Christie Brinkley".

She's 62.

One need not dress dowdy just because one is older.

[Lacey Hadley]

Hi Martha,

You have the right to dress anyway you like, however if going out to dinner en femme with your wife, I'd suggest dressing similar to how your wife may dress. You may choose to dress in a short skirt showing the tops of your stockings and walking with your tallest heels but if your wife dresses more conservatively you may feel out of place and draw undue attention to yourself, unless that is what you want.

I see how you may want to be more sexy and feminine and not too blah dowdie. I too if I were planning on going out en femme and knowing it takes me a good 45+ minutes to shave and do my make up I want to look feminine, cute and even sexy.

If I were going out to dinner with a wife I'd want to coordinate a style and level of dress with her. For me probably if it was a nice formal type restaurant I'd probably put on one of 'housewife' type dresses, quite like the picture in my avatar and likely with some high heel boots. That look makes me feel very cute, feminine and even lady next door sexy. If I were to go with a skirt it would not be too short, probably above the knee, black and again either high heel boots or a pair of classic spike heel pumps. I'd wear a long sleeve formal blouse too. If I went with pants, they'd be ladies dress pants and maybe a turtle neck and a button down or even solid pattern pull over sweater or maybe a pair of my tight black faux leather plants with a turtle neck and jacket, like a cropped leather jacket or my black or white cropped faux fur jackets and either a pair of zip on high heel knee boots or one of my cute spike heel ankle boots.

Getting your makeup and your hair (wig) as best as you can will likely be the most important thing though. We cders generally wear more makeup as we have to cover or blend/contour our male feature but try to keep it similar style to your wife's makeup.

Hope my 2 cents help. I hope that you and your wife have fun.

[Martha]

Thank you all for your advice. Most have said that I should dress as my wife dresses. My wife is 14 years younger. She works in business real estate and wears what I think is very sexy yet profession business attire. I wish I could fit into her clothes, but what fits her are extremely tight on me. So when we typically go out she will dress up more than she does at work. Shorter skirts, higher heels, tighter blouses, showing more legs and cleavage. So for me to match or compliment her I would be in my opinion, be dressing way to young for me. I am sure she will want to have some input on what I will wear for our first date when En Femme.

But then again, I am really not trying to pass as a women. My legs and arms are way too muscular, unless I try to be a female body builder. I may or may not wear a wig. I like the shaved head Demi Moore look. Some nice make up and some large ear rings for me would do. I think I can accept or at least hope I can, that people will look at me and instantly think that I am a man wearing women's clothes. We are use to people staring at us when we go out as a man and wife. We think they look at us because of our age differences and what is this sexy women doing with the old bald guy.

Sorry for getting off track here. I will take everybody's advice and ask the wife what she wants or expects me to wear. I will update this when possible. Thanks again everybody.


Thanks Lacey, I like the idea of the high heel boots. As I have two pairs of classic spike heels pumps, but no boots. I am thinking before I ask the wife, about the boots with a knee length fitted skirt, semi loose sleeveless blouse.


** Edited to combine successive posts, as per: http://crossdressers-haven.com/forums/v ... 65&t=10059" onclick="window.open(this.href);return false; - SL

[Eileen (SO)]

Gee, two Martha's! Love it!.
Martha, I'm not understanding why if your lovely wife wants to have dinner as two women, you don't want to present as feminine as possible? Consider your wife's feelings. Does she want to have dinner with a man in woman's clothes, or with a properly dressed woman?
A shaved head? Oh please no.

With the right clothing, muscular men can look very convincing as women. And don't have to look like a Grandma! I am one and in the mood to do so, I can turn most heads as a damn hot lady!

Just like wine, women get better with age. Let your wife help in choosing outfits and make her proud to be with you.

Eileen

[Diana Michelle]

Eileen's advice on having your wife help you with selecting an outfit is the best. Remember she has been through it all and grown into the role. You Martha are still a novice at presenting as a woman of any age. Too many girls make the mistake of dressing either too young or too old. Just because a woman is past 40 doesn't mean she has to look like the stereotype spinster school marm. Enjoy your outings and remember just because a woman is north of 40 or in your case 57 she can still be stylish dressed. As for dressing sexy, that is more a function of attitude than a short skirt.

[Martha]

OK. Maybe I am still a bit confused as to what or who I want to be. When my wife first discovered my secret, we talked for several days about what I was feeling when wearing women's clothing. What I understood at that time was that I did not want to look like a women or be a women. I just felt sexy wearing women's clothes. Now my wife has taken it a bit further by applying makeup on me on our play nights. I feel extremely sexy and comfortable in heels, stockings, panties, wearing a bra. Makeup is getting more comfortable although a pain to remove. I have had my head shaved so long having any hair on my head is not sexy. So far she has not asked me to wear a wig, just the clothes and a little makeup and some clip on jewelry. We did buy some silicone breasts and I will feel better wearing those because I hope it fills the empty top portion of my bras. I have a few pairs of the VS padded + and they alone are enough without stuffing...My point is I am not trying to pass as a women. I just enjoy wearing the clothes. Which I think my wife understands. We haven't had a chance to discuss Martha in the last few days, but will talk with her what she expects on out first night out. I will share when I can. Thanks for all the input.

[Eileen (SO)]

Martha, maybe you're not ready to be in public until you figure out who Martha is. Dressing sexy can be as either a man or woman, I mean that a man can look sexy to a woman when dressed right. Like most CD's, you prefer to feel sexy in woman's clothes, but you don't feel like looking like a woman. Your wife seems to want to dress you as a woman.
You two should sort this out before the warm season when your outing is planned.

There is more to dressing sexy than short skirts and high heels. At the ancient age of 57 (I'm 59 1/2) the right out fit will make you feel comfortable and sexy.
You're buying forms to appear more feminine but not a wig? When dressing femme, a bald head is not allowed at our home, nor is a two day beard growth.

And get you ears pierced, sweetie. It's more comfortable than clip on's.

Eileen

[DonnaT]

What I understood at that time was that I did not want to look like a women or be a women. I just felt sexy wearing women's clothes.

What part is sexy, to you?

Some like the look of their legs when shaved, in hose and wearing heels. Anything else really does not add to that sexy look.

Some like the look of lingerie on their hairless body, especially including stockings and garters.

Some like the whole looking like a pretty woman, especially with great legs, to be the most sexy.

Some find the idea of wearing sensual makeup with highly glossed lips to be the topper.

Maybe you're the leg type, and haven't tried the sexy makeup with a wig yet, because you're more enamored with your legs. Maybe if you did try, you'd find the whole look even sexier.

I mean, if you got killer legs, a more womanly shape and overall appearance may result in feeling sexier. If you like feeling sexy.

A bonus would be if your wife felt the same way. You'd get the feelings you want out of the experience and she'd get what she wanted as well. Win win, for both. And possibly more opportunities.

I don't wear makeup and a wig at home, because those things bother my wife. So I get to dress and she doesn't get pushed beyond her comfort zone. If she preferred I wore the wig and makeup, then I would. For her.

[Martha]

it's been awhile and thought I would update everyone here if interested. My wife and I have agreed that a wig is preferred on "our first date". We ordered a short blonde wig and it was here the next day. Normally, we play dress up about 2-3 times a month. Since we have been discussing Martha more lately I have been dressing almost every night, but not staying dressed, but just to try new things. We had ordered a few more skirts and tops to try. Now, I think we have come up with my outfit for "our first date" and I love it as does she.