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. Maybe they do for you, and you can find men’s-sized shoes at XDress here. I am partial to the Sexy Ballet Flats, as heels don’t work for me, as I already said, but perhaps they will work for you. All the 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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42 comments

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

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

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

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

Would love to find out how to get started and site should have a chat room and to say all the models are a super hot guy

Edward

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