When and how did you realize you could do it?

[Brittany CD]

When you began your interest in crossdressing, when an how did you realize that you could not only wear pretty dresses, but also make the appearance of a woman?

For me, I enjoyed wearing women's clothes as a kid because I really enjoyed them as opposed to my regular male clothes. I remember looking at my female classmates and thinking how wild it would be if I could have a face and hair like theirs when dressing up. Of course, that seemed absolutely impossible. I thought the only way that could possibly happen is with expensive prosthetics that take hours to apply like on Mrs. Doubtfire.

Around 2006 when I was a teenager, I discovered YouTube. One day I just looked up crossdressing and there was a video of a guy putting on makeup. Towards the end of the video, he had his makeup and lipstick on, and I just thought that he looked like a guy in makeup. Then he put on a wig and I remember being stunned by the result. I couldn't believe that one could put makeup and a wig on and look like a woman. That is what made me think that maybe I could do it to, which I eventually did

[docrobbysherry]

The thot never entered my head until after age 50. However, in MY CASE, I looked so unfem I almost stopped CDing before I started!

The very FIRST TIME I looked in the mirror and saw what appeared to be a strange woman? What was it like? Let's see:

Fireworks on 4th of July?
Getting a shot of adrenaline?
Pitching a shut out the 7th game of the World Series?

Naw! They just can't compare! And, I still get that feeling sometimes! (Big s--- eating grin!)

[heatherdress]

My wife encouraged me to buy my first pair of heels, clothes, wig and wear make-up.

[bridget thronton]

Interest when I was 13, regularly dressing quite a bit later

[Paula_56]

Jamie Austin make-over in at the glamor boutique 1999 Thanks Jamie!!!!!!!

[Noel Chimes]

I realized I could look like a girl when my mom use to use me for a styling head for her wigs. From there it was trying on her clothes that did it. Back then i didn't really need make up. Over the years I tried to work with make up, but I failed miserably. However I kept trying. I finally went and got a makeover and WOW!!!! Now I can't wait for the opportunity to do it all over again.

[BLUE ORCHID]

Hi Katie, I've been dressing sense age 5 but it wasn't till many many years later that I got a wig that I felt I looked like a woman.

[kristinacd55]

I went on one of these makeover of your pic sites, and tried on Heidi Klum's hair and some makeup and said omg I look like a woman!! I still hadn't gone out in public, but that was the defining moment for me. Since then, I started going out in Feb. of 2011 and now it's no longer a big deal to do it.......here's the pic that did it for me

[Beverley Sims]

It is truly revealing what a little bit of makeup, combined with a wig does to your appearance.

[JeanneF]

The first time that I had someone actually show me how to apply makeup was when I realized that I could possibly pull it off. It was amazing the difference in just seeing what potential I had and what an expert could do to make me look feminine.

After that, it was just a matter of trying to replicate the initial attempt.

[katie_barns]

I have been dressing my entire life, I don't think I went out in public until I was in my late 30's.

I did write a store about my first time out. That's when I realize I could do it.

http://www.crossdressers.com/forums/...First-Time-Out

[Kaz]

I have been cross-dressing most of my life too, but pre-internet I had nothing and no-one to work on... so it was just a quick thing, on and off for decades. Bought some clothes and purged, did that again, usual story. The turning point for me was in 2006. For the few years before I had been staying away a lot on business and had tried experimenting with make-up and a wig (badly)... but then I realised thsi was a major part of me that wasn't going to go away and maybe I should invest some more time and effort in it.

You are right, make-up and a good wig make all the difference! This may have been the defining pic that changed it all for me...

[melissakozak]

I was 19 years old, and about 15 pounds lighter. Now that I am middle age, I look more like the secretary of some big corporate office rather than the teeny bopper with the big 80's hair I used to have! All of us go through that AH HA moment in the mirror where we see the femme self staring straight back at us, and this is often the point of no return for most of us. Once we see that girl in the mirror, we realize a very real part of our self is being expressed. I hate to say that as we get older, some of the magic disappears, but it does...it is called maturity....

[Madam Rose]

Bravo on your behalf. As for me, well I had to wait till my southern grandad kick the can because he wouldn't have it. But I always wanted to dress as a woman since I was a teenager. The idea was exitng. But since I was around hill billies who hated blacks, gays, and anyone who wasn't a hill folk, I new I'd never have the chance to be beautiful as I wished.

[Kyndrie]

I started around age nine. I had discovered my sisters underwear in the laundry one day and I think I decided to wear them on a whim. They felt so good that I "borrowed" them. The softness, the material, the look, the fit, these things bound themselves with my budding sexuality and I was hooked. My sister was a bit of a free spirit and even at the age of twelve and was buying lacy thongs and such. As we aged, she progressed to garters, stockings, teddies and all of that. So I had access to lots of fun things.

[Cynthia Anne]

As a teenager I was in public dressed as a girl! By the time I was nineteen I was shopping as one!

[May(be)]

I have a good build and figure for crossdressing, so I always knew that I would have the ability to pull off the illusion, but I decided only this year in May at age 26 that I needed to physically manifest and realize my feminine image before I start to lose my youth. Also, all the drinking as a way of coping was starting to ruin my figure. Now I don't binge drink, but I do binge dress.

I make movies so I have wigs and I am married so, at the time before my wife and I separated (geographically) out of necessity, I had a bag of cosmetics and a closet full of clothes that fit me (we have similar measurements, except she has amazing breasts and I do not even have pecks worth writing home about). Now I am building my own feminine wardrobe so that we don't fight about who is going to wear her new tight black number.

[Angela Campbell]

I have been wearing panties and underwear of all sorts since 5 or 6 I guess. Off sand on, purging, buying new...years. Recently I found myself living alone for the first time in years and decided togo all out. Until this point...about a month ago, I never dressed fully as a woman. This time I got a wig, makeup, top and skirt, hose, shoes, jewelry the works. I was in a hotel and did the whole thing and was just amazed. I really felt like I could go out without too much attention. No I do not think I pass completely but I do think someone who looked close would wonder....they would not be sure but that is about as good as I ever think I will get.

I did recently take a huge step and while at a hotel I left the room and walked down the hall dressed up to go to the drink machine. I was terrified but I did it. I have now found a club in my area that is for crossdressers. They meet once a month at a hotel and have a changing room so I can arrive as a boy then get dressed up there. I am going to do it and see how it goes. I will actually go out in public as a woman for the first time but I will be in a safe place with other accepting people. I am pretty excited about it.

[Stephanie47]

I started wearing my mother's attire; dresses, slips, bras, panties and girdles as a teenager. My makeup look hideous. It wasn't until much later that I experimented with trying to appear womanly. I bought my first wig in my thirties and dressed up for Halloween, totally en femme. I did get a compliment from a salesgirl at a Winchell's Doughnut shop. It made me feel great. For some reason I was more adventurous when younger than now. When I was younger I had more to lose if my cross dressing became knowledge. Older, I am secure, but, I really have no desire to mingle with the masses. I do think my wigs make all the difference is trying to look womanly. A really close shave and light makeup is sufficient for me. I just do not get really close to any mirror. Just the action of pushing my hair from my cheek or smoothing my dress when I sit down makes me feel womanly. I know what I feel is not going to be seen by anyone who see me; a guy in a dress.

[Cheryl T]

I didn't "begin my interest in crossdressing".
It just happened. I always felt that I wanted to be a girl and at about 8 I just began trying things on. That's when I realized that this made me feel happy. It just felt right.
From there it just naturally became a desire to present myself to the world and I did so (surreptitiously) the first time when I was about 19. I looked terrible as I had no idea how to use makeup. Then over time, with practice, I refined things to where I felt I was presentable and went out to meet others.
Now I go out all the time and it's just a natural thing for me.

[Julie Denier]

I was always curious since I was very young, but never dressed fully until almost two years ago, at age 38, and really liked what I saw. I could never go out, but I got to where I looked decent enough that I was comfortable sharing photos (my profile pic is my favorite).

[Alice B]

Like Sherry I did not start until late in life. Very late at 64. The first time I was fully dressed, make up and all, and looked in the mirror I did not see fireworks, or any thing like that. Just a wonderful feeling of relaxation and completion. Don't know where it came from, but do not want it to go away.

[Miss charlie]

I have been cross-dressing most of my life too, but pre-internet I had nothing and no-one to work on... so it was just a quick thing, on and off for decades. Bought some clothes and purged, did that again, usual story. The turning point for me was in 2006. For the few years before I had been staying away a lot on business and had tried experimenting with make-up and a wig (badly)... but then I realised thsi was a major part of me that wasn't going to go away and maybe I should invest some more time and effort in it.

You are right, make-up and a good wig make all the difference! This may have been the defining pic that changed it all for me...

This is pretty much where I'm at, but the turning point for me is now at 28 as I'm starting, well trying to accept this part of me and find out how far it goes. I have just started on the more time and effort side of it and am loving it although sometimes when I'm dressed I do have to look at myself in the mirror and tell myself it's alright to be me

Kaz you look gorgeous in that pic !! If I had a pic like that, it would have changed things for me too xxxx

[kimdl93]

I'm a lot older and really quite jealous of your early discovery. From my adolescence till I was in my 40s, I was confined to underdressing and lingerie intended only for the bedroom. Its only really been a few years since I first recognized that it was possible for me to dress completely en femme. The key moments for me were probably when I first acquired breast forms and my first wig. I saw potential in my appearance that I'd never thought possible and soon thereafter had a corset, some other shape ware and make up.

I am truly a bit envious of the internet generation and all the resources available to you. But I've told several of the younger girls here that I sincerely wish and pray that they will take advantage of the opportunity and live as much of your young life as possible en femme. Looking back I sincerely wish I'd started sooner...you can't get back the lost time.

[lauren_m]

I'll let you all know if/when it ever happens for me!