What was your first experience like?

My sister let me wear her poodle skirt and petticoat and she took me to a local dress store and paraded me around for all to see how sissified I was.

Once, many years ago, I went for a stroll at night, fully dressed. It was very late and no one was around. I saw no one. I guess I just wanted to do it once to say that I did. I've never had the courage to do that again, and never at a time when there would be others about. I'm thinking of making an appointment for a femme makeover though. I'm scared. I'm still a closeted CD.

hey there!

Well, this was a few years ago with a friend of mine. Went to a local transgender club near where I live. It was a wonderful experience to be completely truthful. I was dressed in a long black sleeved top and a long black pencil skirt completely with dark-brown wig. Would love to do it again sometime. Hope that helps.

Today I took a small but big step.  Got fully dressed, hair makeup etc and went out.  Just a couple of little things.  Gassed the car up at a packed filling station, and swung through a Wendy's drive through.  Not even a 2nd glance while filling the car with people walking by and filling up next to me.  The folks at Wendy's were very nice although I have to believe my voice was not passable lol.  But who knows, the people at the windows were very friendly and smiling so just maybe.....  All in all very exciting and nerve wracking at the same time, but oh so glad I did it!

Unfortunately, my first experience out was so many years ago, all the details are fuzzy.

I can recall getting dressed, wearing a brown romper....and having to pysch myself up to get out the door. I remember walking through our back field, into town, and going into Tesco. Then scurrying home....so scared that I had been "Outed".

Looking back, as I type this, little did I know, but I was already outed.

Cookie 🙂

I know how scarey it is at first girls but once that is behind you it is so much better. Now I love taking my newbie friends from the clubs out in public for their first time and watching their reactions to everything. I feel like a mother escort but love doing it

Mine was with a friend, a girl when we were 12 or 13. Over 50 years ago. We were dressing up and I dressed up in my older sisters dress, it was yellow with some black design on it, and a pair of white cotton bloomers, part of her school uniform. I had a scarf around my hair and her shoes fitted me.  It was a fun thing to do but I then wanted to stay that way. My parents noticed that I later collected a few bits and pieces of female clothing like socks and unisex things and they took those away and said nothing. But that started something that has never stopped. Dressing fully as a woman feels more natural than dress as a man now. That first time, when I think about it now, wasn't hard to do. I saw the clothes there and just dived in. It was like suddenly finding part of me.

My first experience was 30 years ago, when I was 4. It was my mom the one who tried a petticoat on me, I still remember that day. I thought it was too soft, too beautiful, that I couldn't stop wearing her clothes or my little sister's anymore!

The first time I dressed in public was when I decided to go to "drag night" at the local gay club. I wore white stockings with pink lace cut panties. Had a knee length black silk dress and white strappy heels. I couldn't believe how great it felt going out like that. Had a great time!

My first time I went out in public was terrifying and exciting at the same time. I was a teenager and had the weekend alone as all the family was gone. I wore a wig my sister had, a pair of shorts and a tank top with a bra and undies. I had little body hair a the time and had been using my sister's and mom's makeup when I dressed at home, and had it down pretty good. I wore a pair of heels that belonged to my sister and had been practicing walking in them for awhile and had that down pretty good too. That night I left out of the rear of our yard so the neighbors wouldn't notice me and walked down the alley to the end of the street, then walked around the neighborhood to a local strip mall. As I walked past the mall, some guys at a 7-11 started whistling at me but I just ignored them and walked on. Several drivers who passed me honked their horns and stared but kept driving. When I got home my feet were killing me but my heart was pumping and I was so excited. After that night there was no going back. I later realized I was kind of dressed up like a hooker with the short shorts and heels and walking the streets at night so I started wearing flats or sneakers instead.

My first time was when my parents dressed me as a girl on Halloween of all times. I was 11 or 12 and I was in a dress and even had boobs, stockings or something stuffed in there. I was brought to all my parents friends and, no one knew but it was an experience I didn't understand. I knew I was embarrassed but I knew it was something I couldn't forget, nor did I ever.

My first real outing dressed (not counting the fetish boutique makeover 20 years ago - was too controlled and fake) was an afternoon tea at a friends.   She invited me to attend as Sarah if I wanted.   So I turned up under dressed and slipped into a blouse, skirt and heels there.   Had about 2 hours of chatting like normal but with me dressed.   Was great and seemed so natural.   Was worried at first and almost didnt come out when I was dressed but I did and had a good time.

its been wonderful i talked to my wife about telling my 1 daughter out of 3 so far.we invited her over 3 days before christmas and my wife talked to her while i was dressed and hiding .when my wife called me and said its ok come on out i was so excited and also scared of what was going to happen even that i knew it was ok because she said come out as you are.i came out and my daughter gave me a smile from ear to ear and came and gave me a good hug and said i love you and very proud of you.that was a big relief, so she asked me if she could buy me some things and give to me in private and i said yes you can . she didnt like my wig so we sat down and picked out the one im in now and we try to have a girls night once a week.they have been helping me with my makeup and yesterday i was feeling so good that we went to taco bell drive through i ordered and paid for our food as my first time out the girl at the window looked at me and took the money and gave me my change then she went on working and never looked again till she gave me my food i knew then i passed and it was wonderful love you all and thats enough for now xoxoxo

Jennifer and Sarah: that's awesome for both of you! Yay!

Jennifer, your daughter sounds amazing! And your wife, of course. I hope "coming out" to your other kids goes just as smoothly.

Margie: That reminds me. Huh. When I was around that age, I got dressed as a girl scout for Hallowe'en. We borrowed a friend's uniform, and my mom did my hair and makeup. I don't remember wearing a wig, though maybe I did. It would've been the early 80s or so, so I had shaggy hair that maybe could've been styled a little bit. I haven't "forgotten" about this, but yet I never really think about it when thinking about when I got started dressing.

Not counting that, my first (and so far only) time was last fat a support group for transgender and CD people. I got dressed there, then changed before I left to come home. The only thing I did in advance (other than underdressing, of course) was I did my nails. And I was certain that everybody was staring at them while I was driving to the meeting. Of course, they weren't. But paranoia is a weird thing...

I'd love to go out shopping or to dinner. But for now, I won't be because I'm quite hesitant to leave my house dressed, with the chance of neighbors seeing me.