Dressing Your Age

Greetings to you, dear readers. I hope life is progressing well for you. Have you noticed that life as a crossdresser is a journey? It certainly is for me. The further I go, the further I have to discover things about myself – all things good, I’m happy to report.

So today, I’d like to discuss age differences in who we feel ourselves to be. What age do you feel yourself to be in your crossdressing life? That may seem like a weird question but think about it. Do you feel yourself to be a young girl? Did you perhaps start crossdressing by wearing your sister’s bras, panties, and skirts and other things? You know – the frilly socks, Mary Jane shoes, the schoolgirl uniform with a skirt and blouse, like the Teacher’s Pet Uniform from Xdress you can see here.

Some of you, I know, remember how luscious it was as a young boy to fantasize about being a girl in those wonderful school uniforms, training bras, and panties. Don’t forget to add some nice black stockings, like the Simple Seamed Stocking you can see here. If you like, you can go to a brick and mortar store and find thigh-high hosiery. Or, if a bit more daring, try a garter belt with the hose. XDress has several choices. So, do you see yourself as a young girl dressed in those innocent clothes of a prepubescent girl?

On the other hand, you might have started your crossdressing life by wearing your mommy’s clothing. My mom had a pair of shoes I loved. They were penny loafers cut so cute. They fit me perfectly, and I asked her if I could wear them. She was fine with that, and I wore them a lot – even in public. I tried her high heels, but they didn’t work for me. I am partial to flats, as heels don’t work for me, as I already said, but perhaps they will work for you. All shoes are really attractive – I just wish I could wear them all!

Having taken to my mom’s clothing, I am particularly drawn (given my age) to the 1950’s housewife dresses. Think Donna Reed, if you are old enough to remember her –the housewife full skirt and dress kind of look. Of course, you must also wear proper hose and shoes, as well as a corset. You can find proper corsets from XDress here. How could we forget wearing a proper bra with proper housewife clothing? Go here to see some wonderful examples of bras that fit just right for our gurly build. It’s also a lot of fun to go shopping in a brick and mortar to find other bras and panties. I should know – my wife has bought more of my bras and panties for me than I have!

On the other hand, some of you may prefer the Goth look. What led you to that? Why do you prefer black everything, including nails, makeup, and clothes? What led you to that?

So, what is your preferred age and style of clothing? I personally prefer an age-appropriate dress, given my great admiration for my mom and wanting to look like her. Perhaps yours is younger or edgier? Warm-up that keyboard and tell me about your age/style preference. As you know, dear readers, I love to hear your stories.


Fond regards,

Angie

35 comments

O.K. Please allow me to take a moment and comment directly to “Mikey”.
Mikey, Dear,
Please take your own advice and do not waste another moment of your time to enjoy the things you truly like. I am in my seventies and I would love to be as young as you are now.
The other thing I want you to do is to stop right now with the negative thinking and remind yourself of all the positive qualities you have that help you achieve a feminine look and feel. There are plenty of cis women who don’t look all that great but I would be hard pressed to not be able to find SOMETHING about any woman that wasn’t pretty or feminine.
I am sure there is lots you can do to enjoy your feminine side. If you want to go out dressed maybe you could wear a ladies plaid skirt as if it were a kilt. Only YOU will know about the pretty panties underneath or the cute bra you have on.
I have to get to work now but I will have more to say to you about this later and I ask the others on here to send you a note as well. I think you will be surprised how many of us are older now and still dressing. All at various stages but all having a great time doing something that gives us immense pleasure.
Do not give up trying and do you best to enjoy yourself and stop worrying about what other people think. Yes stay safe and be careful but you can do it and have fun. You don’t have to be a raving beauty to please the most important person in your life ,which is YOU!
There is nothing shameful about a man wanting to dress and act and just be like the most beautiful creatures the good Lord ever put on this earth.
I adore women and all feminine things
I would like for you to treat yourself like a Lady.
Best wishes to you and all the struggling inner girls amongst us.
Life IS short . Enjoy it
Cordell

Cordell April 01, 2020

All I’d like to say is, please enjoy every moment you can, however you decide to dress. I left it too late, I’m 60, very big and have always, my whole life, wished to dress in the wonderful underwear, and pretty dresses that women get to wear. Now, I just look like a fat twat in a dress. Don’t leave it like I did, live it and enjoy, every silk, satin, lacy moment.

Mikey March 31, 2020

Hi Angie and everybody.
Thank you all creating this site and allowing some of us crossdressers to have a chance to explore others experiences and to express our own feelings and desires for our feminine side.
When I was first attracted to wearing skirts at about five years of age ,I instinctively knew it was something I should keep to myself. I had three older brothers and little opportunity to dress in a skirt. It was one I made for myself and quickly out grew it anyway. Family circumstances changed when I was ten and I was sent to live with an aunt and uncle who had children all a bit older than me. Two of which were girls. It was a religious family and again I knew wanting to be a girl or wanting to dress as a girl would not be understood.
However I adored the pretty dresses and little strappy shoes the girls wore to Sunday school and places that allowed for more formal wear. I loved the way the sunlight shone through their dresses and showed the little panties underneath. Sometimes the wind would provide a great view of panties or the girls (not just cousins )would sit in a way that provided a chance for a glance.
I wanted so much to be pretty and wear cute things like the girls all wore as well, instead of being (as I felt) like a plain boy dressed in the same drab way all the time whether for Sunday school or wherever.
Living and working on their farm didn’t allow much time or opportunity to do much as far a crossdressing went in those days. In fact I didn’t even know there was a name for it.
But one day I found a couple of frilly crinolines in a place I was able to slip one on and tuck it down into my jeans and then take a walk by myself way out in a pasture and then remove my jeans so I could walk around and run and flip up the pretty crinoline /slip and feel the sun and the breeze blowing it around my legs. I was truly in heaven and needless to say I slipped (no pun intended) it away again every chance I got.

I love wearing panties and skirts etc. all the time now and my dear wife is very accepting of my girlie side but it was hard won. But more on that later. Please stay safe everyone and remember…..there are lots worse things we could be into than indulging in our sweet feminine desires and fantasies. Warmest regards to all Cordell

Cordell March 23, 2020

Ally, I am so with you. A miniskirt during hot weather is so much better than shorts. Absolutely bare legs. Who in their right mind would wear hose in hot weather? Sandals are good in summer – especially if you have a pretty color of polish on your toenails. Personally, I’m partial to flats and ballet slippers. Thanks for your post.

Fond regards,
Angie

Angie March 19, 2020

Hi Angie – well I do have a denim mini that I wear around the house during the summer. Usually with bare legs and flats or cork platform sandals. That’s just because it’s cool and comfortable though. Much better than shorts on a hot day.
Ally x

Ally March 17, 2020

Ally x, I’m pretty much with you. As I’ve gotten older, my style of dress is pretty moderate and age – appropriate. Having said that, I still love a miniskirt on a hot July day!

Angie

Angie March 16, 2020

Hello again. just want to add a further comment. I fell in love with femininity at a very young age. I adore all things feminine and just want to immerse myself in it. I love wearing panties and skirts as well as nylons and heels. I like to fantasize about actually being female ,but not really as that would probably take the fun out of it.

Cordell March 15, 2020

Hi Randy, you were very lucky to have a mother that accepted you for who you are. I love to crossdress from time to time and find it very exciting. I do it in the privacy of my home when my wife is away. She knows I do it but doesn’t care for me doing it. But I just keep telling her that I love but this is who I am.

Jaclyn March 14, 2020

It’s great to hear other older readers offering their experience of feminine dressing. What comes across so much is the importance of not wasting your life. Experiment and find others to support you as you dress the way you want to.
I have no age thing when dressing. Each to their own. As I’ve mellowed I’ve just adopted a more moderate and mature style that I think suits me.
It is so lovely to be able to have this conversation here.
Ally x

Ally March 13, 2020

Cordell
Welcome
Glad you found us here. You and whatever your expression of self is, is welcome here. We all have a story to tell and a journey. This is a safe free place to discuss it. Big thank u to xdress Angie and all who created it support it and make it happen
Thanks to this site i am so much more comfortable with myself
Stevie
Wear something pretty today, I am

Stevie March 13, 2020

Hello again and thank you for the warm welcome
I have a lot to add but for now just a short note to say, Angie, I too love the young girl look in pretty dresses and ruffles and frills. It is indeed such a sweet look.
Thank you as well Peter
But just let me say for now that something I have learned is that other people don’t really seem to care that much what somebody else wears. The trick ,I find<is to be confident and sure of yourself. If is is O K with me ,then it seems to be fine with them. I have many experiences going out in public wearing a skirt and ladies sandals often with nylons. I have been in places like the grocery store ,movie theater. Princess Auto, the bank and other places wearing a skirt . Not trying to look like a woman …..just a guy in a skirt. Be confident….be brave ..have fun. Above all be true to yourself. Don’t wait until you are old to live your life like you want. I am sure nobody else worrie about what you think of their clothing choices.
BTW Sallie I will tell you all about my dressing as a French maid in another note. I love that look as well.
Again,thank you all for letting me have somebody who truly understands what it is like being a crossdresser. Personally I LOVE it

Cordell March 10, 2020

Hi again all. I just love reading your stories! Cordell, do please share more with us. I suspect that our experiences parallel each other, as do those of many others who are contributing to this thread. Keep those comments coming!
Fond regards,
Angie

Angie March 10, 2020

Welcome Cordell, thank you for sharing your story. I love to read stories that show how others were influenced when growing up that lead to our “dressing age”. I mentioned that my dressing age is definitely on the younger side. I was mainly influenced by schoolgirls at my local catholic high school hiking up their school uniform skirts to make them look like mini skirts, almost showing their panties, and I loved the look of white knee high socks in Mary Janes. Everyone must have a story, and I look forward to reading more!

Peter March 09, 2020

Hi everybody.
I really love reading your stories of how you all started enjoying the wearing of sweet girly clothes .
I lived next door to an elementary school in the early 1950s and about the age of four or five I was treated to the wonderful sight of pretty girls wearing lovely dresses or skirts and showing their pretty panties as they skipped rope or used the swings in the school yard. That was when I was first attracted to skirts and wanted to see how it felt so I made my first skirt from a pair jeans by cutting off the legs and crotch material. From the first moment I put that on I was hooked for life. I agree that crossdressing is a journey as I progressed from wearing skirts to include panties and more as time went on . I remember vividly the first time I sneaked a pair of my cousin’s nylons and the exquisite sensation I felt when I first pulled them up my legs at about twelve years of age. Then at the age of sixteen I scavenged a complete outfit of hers from panties and little grey skirt to nylons and garterbelt and strappy open sandals. it was Halloween and I could hardly contain my excitement as I shaved my legs and dressed completely as a girl for the first time in my life. Yes I appeared in front of family but they all just thought it was a one off ,just for Halloween . In my seventies now and still love being dressed as female. I would love to elaborate if anybody else would be interested in hearing about the rest of my crossdressing experience.
I loved reading all the comments for you fellow crossdressers. So nice to know there are others of you and that I was not the only one who liked wearing panties and skirts which is what I thought for so long when I was young

Cordell March 09, 2020

I would like to wear more feminine outerwear items as well as panties and camis, but I don’t think I would pull it off (I am 6ft 2" and in my 40’s and reasonably well built). I do wear short womens althletics shorts and leggings, and recently have fallen in love with very short cap sleeve T shirts with wide necks. These show my muscular arms and chest off well, and I really don’t know why these aren’t made for men (hint to bodyaware) My back yard is reasonably private so I can wear these there, and have occasionally run out to the mailbox, but only under cover of darkness. So I would say my dress age is late teens or early twenties. My wishlist would include a short miniskirt with knee high white socks, mary janes and a strappy bra top under a cropped cap sleeve T.

Peter March 06, 2020

Dear Krystin
Thank you for the encouraging words, I m not trying to pass either but love the femme fashion
Underneath and unisex looking jeans will have to do for now, lol
I hope for the day when a man in heels is just a different fashion choice
Stevie
Wear something pretty today
I am

Stevie March 06, 2020

Hi Stevie,
Yes, I live in a large city and there are various places I can go without any hassle. Some are LGBQT friendly and others are not, but they still are very accepting. As I mentioned in an earlier post, I usually dress androgynously but with definite femme emphasis, though I couldn’t pass as a genetic girl and don’t really want to. Thankfully my GF not only supports me but is actively involved with my dressing, giving me advice on outfits and makeup. Also, most of my co-workers are women and they are on board with my dressing, which I usually do a couple of days a week and on special office functions

Still I can relate to your wanting to go on a dressing binge. Sometimes I feel like doing the same thing and actually trying to pass as a woman. Maybe someday soon crossdressing will be just another kind of fashion choice and people will hardly notice. Until then, wear something pretty underneath!!

Kyrstin March 06, 2020

Hi nathan angie krystin
I envy those of you that can dress how you want where u want
Is there anyplace that you know of where a person could go on a dressing binge? Just asking because the desire is so strong for some of us and its almost painful sometimes
Sometimes the underdressing isn’t enough
Wear something pretty today, I am: pretty tan/ brown nail polish with black cotton brazillian cut panties
Stevie

Stevie March 05, 2020

I agree with Stevie and Kyrstin. Most of the compliments come from women but men do occasionally show interest as well. It’s such a wonderful feeling isn’t it? To me it makes me feel so much more confident!

Today I’m wearing a classic; leather skater skirt with black hose, a plain black tee and 5" heeled boots. It’s such a cute outfit! Keep the comments coming, this is a great conversation!

-Nathan

Nathan March 04, 2020

Hi “Gurlz”??!
I find women more accepting, my best friend is a woman who accepts me and comments on my pictures and gives me advice. She has agreed to go to an LGBTQ meet up (that our employer has set up) with me while I am dressed
I ve told her i ll be a little conservative at first, maybe skinny jeans stillettos bra panties cardigan and a little make up

Stevie March 04, 2020

Jase

Oh definitely girls are more accepting by about a 3:1 margin I’d guess. Most of those sideways glances I mentioned were from guys, but I’ve also had positive comments from a few males too. I wondered if they were secretly wearing panties haha!

Kyrstin March 04, 2020

Kyrstin, I wonder if its more girls than guys that give you compliments? Generally I find girls are more accepting

Jase March 03, 2020

It’s fun to read all the styles each of you enjoy wearing. I can get away with a sort of feminine leaning androgynous look at work, 2” heels/boots, skinny jeans, light makeup, that sort of look. Weekends out with my GF, I tend to be a bit bolder, with mini skirts and 4” pumps along with a femme top and jacket. We’ve got a few sideways looks but no one has ever been rude, and I’ve even received a few compliments!

As Stevie says wear something pretty today!
Kyrstin

Kyrstin March 03, 2020

Angie
Just a further comment I wish I had come of age now in my day I would have been run out of town for crossdressing .Actually my ex told my children I liked to dress I have never confirmed or denied its no ones business and again young girls frills and ruffles will forever be my favorite its such a sweet place to be

micki March 03, 2020

I wonder if anyone else like wearing French Maid outfits?

Sallie March 02, 2020

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