Dressing Your Age

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

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40 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

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

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

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

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

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