In the genre of crossdressing, what's your fondest memory of a milestone or, a turning point or, when you started something that you were a little leery of but now enjoy frequently.
I guess this could also include the unfortunate unpleasantries that accompany this lifestyle.
After I see a few, I'll add my own experiences.
I've waited so long for this time. Makeup is so frustrating. Shaking hands and I look so old. This was a mistake.
My new maid's outfit is cute. Sure fits tight.
And then I step into the bedroom and in the mirror, I see a beautiful woman looking back at me.
Smile, Honey! You look fabulous!
There are more than one. Wearing a lace cup underwire bra. Painting my fingernails. 🌺
Out and about at 17 and first shopping trip with my Aunt.........
Hi Carla, I think that getting my first set of foam breast forms from the
Montgomery Wards Catalog store about 45yrs. ago......
Having my ears triple pierced is AWESOME, ~~...
I can explain it to you, But I can't comprehend it for you !
If at first you don't succeed, Then Skydiving isn't for you.
Be careful what you wish for, Once you ring a bell , you just can't Un-Ring it !! !!
Hi Blue, how's Balt-y-more, Hon? Bought my first bra at Montgomery Ward in the 60's.
I've waited so long for this time. Makeup is so frustrating. Shaking hands and I look so old. This was a mistake.
My new maid's outfit is cute. Sure fits tight.
And then I step into the bedroom and in the mirror, I see a beautiful woman looking back at me.
Smile, Honey! You look fabulous!
Thanks Carla,
What's a great thread.
My turning point was joining this site and communicating online.
Now to get out and meet my new girlfriends enfemme
"I remember the first time that I ever"...stole my teachers panties!
He was so mad. Sorry, only kidding. I just couldn't resist. I guess I have strange sense of humor.
Seriously, I think it would have to be the first time I tried on heels in a shoe store. I've bought other items of women's clothing but that was the first time I ever tried something on and left no doubt as to who it was for.
Carla,
I'll miss out the starting point which is too mixed up to go into now.
Turning points , there have been a few, I think borrowing my GFs negligee set and falling asleep only to be woken by a totally turned on GF when she found me wearing it !
Getting my first full set of matching underwear ( Charnos ) with stockings and putting them on for the first time, which lead onto buying my first pair of heels !
Different sort of turning point, finally getting answers to my CDing, through counselling.
Final and most recent, putting it all together and walking out the door dressed and madeup to meet other CDers socially .
Carla,
I can't wait for your answer !
Last edited by Teresa; 06-09-2016 at 02:28 PM.
Wearing my sister's pink panties for the first time, at about age 8
The first time I pleased a boy as a teen.
First time going out fully dressed in a cute skirt and top with sheer stockings, heels, and.... no panties. The thrill of doing dangerous things, I guess
[SIGPIC][/SIGPIC] My GG GF Julie and I send you all hugs
I was about 12 years old, alone in my bedroom, wearing my ordinary male bluejeans, a bra of my mother's stuffed with socks, and a stretchy top of my mother's. I was on my bed, rubbing my "breasts" against a pillow, and moving my body rhythmically on the mattress. The more I did it, the better it felt, until it suddenly felt way way way better, and there was a pulsing sensation down there. It was a pleasure I had never felt before, but so intense, and leaving me with such an uncomfortable feeling, that it made me afraid that I had somehow damaged my body. And, I discovered, there was a smelly mess to clean up. I had no idea that was going to happen. I was scared enough to say to myself, "I need to make sure that never happens again." Of course, I got over that feeling, and it did happen again. But the first time was unforgettable.
It was the first time I achieved the look I had been seeking. Looking into the mirror, it was an "oh my!" moment I'll always remember.
The first time I went to a TG Org meeting. It was quite the adventure.
Second star to the right and straight on till morning
First time fully en femme: 7th grade, using clothes borrowed from my mother, and rolled up socks for forms. That was 55 years ago.
getting into a dress
"You're the only one to see the changes you take yourself through", Stevie Wonder
oh there's more than a few, but maybe the single most memorable moment for me was trying on my first lace front wig.
I think that was the point at which I finally looked in the mirror and said "well hello there, girl!"
there's just something about realistic hair that flips a light on in my brain I guess. It's not that I don't feel girly without good hair, but I can't really see it, otherwise.
"Why shouldn't art be pretty? There are enough unpleasant things in the world." -Pierre-Auguste Renoir
The first time I shaved my legs, donned a pair of pantyhose, zipped up my dress, and stepped into a pair of heels--all of which I had purchased for myself. Such an amazing feeling.
Putting on my first wig and seeing what a huge difference it made.
I remember the first time I put on makeup and a wig and looked at myself in the mirror. I couldn't believe it was me, I couldn't recognize myself. I wish I took a picture.
Easy. Hands down it was putting on my first dress at 12 or 13 years old. I actually questioned if putting on a dress would MAKE me gay!It didn't.
Ordering my first piece of female clothing, a tank dress, over the phone. Talk about nervous.
Tried on one of my mother's satin slips, and panties and stockings. I was five or six years old and little did I know how much pleasure that one event would bring to my life!
The most common form of despair is not being who you are. - Soren Kierkegaard
I think mine was that first public outing when at a party I went as a French Maid, it was the first time I did my own makeup.
I had fun with it and then I knew this can be fun it doesn't have to be hidden
So many firsts. First dress, first boobs, first wig. But the one that knocks them all down is the first time I saw her in the mirror. Up to that point I could tell myself anything to convince myself this was just a harmless kink that I could take or leave, but after that day I knew she had been in there the whole time and I needed to go free her.
"I'll always remember the first time that I........"
......dressed fully for the first time. Up until I first joined this site, I strictly was a "underwear" CD. That is, ONLY corsets/garter belts, panties, stockings etc. After some encouragement from some members here, I bought skirts and some tops. I was quite surprised at what I looked like in the mirror. Since then, I dress pretty much that way all the time now. It was a turning point for me.
"Taking the time to be in touch with my feminine side"
When I wore a black and white dress out for the day- it fit perfectly, and I felt happy to be me - so I didn't mind the very few stares or chuckles.
I really loved it when the friendly young women at the museum wanted to talk- I felt I had established a public niche for any man who wants to wear a dress.
We are all beautiful...!
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