I am an older man. My profile says in his 40s because I always use forth of july 1976 as a birthday on any document, but my real age is sixty something. I am a child of the 1950s. That was when I grew and my earliest memories are of little girls in wide skirts with lots of petticoats.
Frilly (and then, "frilly" was everywhere) panties, and dainty little shoes were the style of the day. The street I lived on was 99% girls. I was the only boy there and all of my fiends played hop-scotch, tea parties, and with Dolls. I was the "man" in every game of House. Occasionally, while at various friend's houses though, they would play dress-up with their male victim; Me. I enjoyed the HECK out of that! Every time Mom took me in to the barber shop I fussed. I so wanted to grow my hair long like all my friends...
Like many here, I have been a cross-dresser most of my life. My first memory of it was playing dress-up in my mother's clothing with my sister age 7. it was fun. Cowboys and barbie dolls were the toys of that era and I seemed to gravitate more toward dolls then guns.
I also recall: once, we had gone to church. I must have been 7 or 8. I was in your typical little man's suit with a bow tie and it was scratchy. It must have been early spring maybe Easter but for some reason all the little girls were dressed for First Holy Communion.
Folks if you have never seen a late 1950s little girl in a Communion dress of that era's style you are in for a treat! Google it. Fussy and frills, lace, ruffles... at that time the style was above the knee bouffant skirts and sheer bodice. Slips and petticoats were lacy and lovely.
I was in awe of the confection. I turned to my mother and said (probably too loud in church), "Mom can I have a dress like that?" I say too loud because my mother blushed so I think others heard me. I was child and unembarrassed at the time. "No" she said: "Little men do not dress like their sisters". I recall being disappointed but I never never forgot that, nor those pretty pretty dresses.
For years I would only be interested in church in the spring.. Communion dresses and Easter dresses became almost an obsession. As time went on and styles changed, dresses became more plain and less elaborate. I lost interest. For years I forgot such ways and grew up basically a "normal" kid, save for one thing: I loved girl's panties. and nylon sheer nighties; the more frilly the better.
Oh well, nature handed me a different card to play so I grew up, discovered girls, got married. Got divorced, spent years bitter about that, got married again, this time had a kid. Raised a kid, had a career, eventually got a second divorce and now I am retired and, live alone. But I never forgot.
Of course all through those years I cross dressed. Mainly in lingerie. If any remember, Tosca made some beautiful sheer double chiffon baby dolls back in the day with sheer bikini panties. I had several such over the years. I was vastly disappointed when Sears Penny's and Montgomery Wards no longer carried this style. Back a few decades ago I used to travel on business. In every town I would check the malls looking for such Sometimes I was lucky (thank you Denver!).
Now, I am an old haggard retiree. I have no parent telling me what is right and proper, no spouse to nag me. I can basically do what I want. and what I want is...
I have never been the typical cross dresser (is there such a thing?). Mature women's clothing has zero allure to me (except for a few special cases). What interests me are those cute little girl dresses of my youth in the late 1950s. I soo love frilly. Petticoats, Slips. Lace socks. the style and accessories of that precious time.
Today? well today the "style" seems to be tee-shirts tattoos, piercing, and the only color co-ordination is the purple hair to match the black and blue marks a partner gives the girl. Times have sure changed. For the btter? I am not so sure.
But today is ALSO the age of the magic world of Internet. You can do Google searches for anything and I did many on frilly little girl dresses till one day I chanced on a picture of a man dressed in a divine dress. WHERE DID HE GET THAT???
I started digging. Soon I found there were others who shared my "interest". and tailors and seamstresses who had scaled up 1950s patterns or made their own and built custom little girl dresses.
I found such a tailor, sent them my size (and a wad of cash) and hoped. Soon (but NOT soon enough), a package arrived. Tearing off the tape and packing material I held up a confection in lace and lovely. Heart beating fast, I dug through my drawers for pretty underwear and put it on. Oh I was in heaven!
I looked in the mirror and saw, an old man with a silly dress on. well THAT will never do! Next I ordered: a wig, accessories, frilly lace top ankle socks... and shoes.... Yes. shoes.
Oh my yes... SHOES! I now understand the female fascination. My love is patent leather Mary Jane style. Of course in conservative black but also pretty other colors. Not so much heels, though I have a few pair of spikes and high heels, but I prefer lower heels or flats. Just like the kind those little girls wore all those years back in church. a pair in white was one of my obsessions for years... till I found some.
Thus started my... "hobby". Today, I have a collection of 3 or 4 DOZEN pretty dresses. Drawers full of lingerie (if anyone is interested I know a tailor in FL who makes WONDERFUL training bras in big boy sizes), and can now dress as I like.
My target is that what to me is the perfect age of around ten or eleven; Well old enough to be potty trained, but young enough to not face the horrors of puberty. I know you know this: at that age you understood the world. You "got it". You had figured out how adults, parents, school, generally how things worked and you were confident and looking forward to patently getting bigger and being able to become ruler of the universe. Then... hormones struck.
Suddenly: chaos. Breasts and menstruation, Hairs everywhere plus zits, voice cracking and bones too when others experiencing the same thing beat you up. Regardless of gender, I know you have been there, we all have.
Part of my interest here of course is sexual and I do get that certain frison when dressed frilly. But part is comfort. To me, dressing up is comfortable, yes even liberating. Some girls may wish to be pipe fitters. I just want to dress pretty and hug my teddy bear.
Age 10-11 were to me the perfect age; and basically, the 10-11 year olds of say 1957-1958. The styles then are absolutely charming. Fortunately there are tailors who agree with me.
Mainly these artists make "square dance" outfits but some also make sissy dresses. If anyone is interested I can give makers and supplies names and web sites. Ah the magic of eBay!! Besides them, Etsy is also a good place to look. Others have shops sorts or their own websites.
On top (or under) dresses, there are makers of petticoats and other foundation garments in big boy sizes too. I have bought many and have my opinion on the good bad and the ugly.
Wouldn't it be nice to have a cross-dresser dress reviewer? Just a thought..
I am not much into makeup. I paint my toenails (don't we all?) but my fingers I keep plain as I must in life dress as a manly man on occasion and such would provide uncomfortable questions. My style is, as I said of a little girl. Well little girl's Mommies don't usually allow them to use makeup like a painted whore so I do not.
The more virginal look is my target.
I am not sure if it is allowed here but I have created a Youtube account with videos. this is the address https://www.youtube.com/channel/UCoPagjwndQZL-W9GnSvnqqA Some say a picture is worth a thousand babbles. Perhaps a video says more. Yes pink is my favorite color. If interested, there is a video there called "Confessions of a Tranny" I do think it describes me and my way more then I can here.
Well that is me and my life. I hope others find this of some interest -Joan Cairo