Memories of putting on your first dress that fit,So Wrong yet so Right and so Fun

I don't know if it is just me or if all CDs have very vivid memories of some of their earliest CD experiences ? I think its very hard for even our supportive SOs to understand just how much fun this was for some of us growing up to see how we looked and felt wearing girl clothes, and just how addictive it could become

My first time actually sneaking into my sisters closet was triggered by my mother and one of my sisters. One of my sisters and her friend were helping my mother to bake cookies for their Brownie scout meeting they were all headed to. Well I mentioned it sounded fun that they were then going to decorate the cookies and then eat them. Well my mother giggled and said something like well sorry but you have to be a Brownie to attend. Then she left and came back minutes later with my older sisters old Brownie dress and beret announcing to the girls that it looks like we have a new Brownie joining us ! Well everyone was laughing but me as my mother tried to convince me jut how ADORABLE i would look in the dress. At one point she was literally chasing me around with it. Well after the fun was over and they left the dress was still laying on my older sisters bed with the door wide open.
At that point i just knew I had to put the dress and beret on ! When I looked in the mirror I just thought it was so fun and funny to be in the uniform and how much i looked like a girl. I then went and got socks and shoes to put on and just kind of acted girlish for about 15 minutes. I knew it was wrong but it was so much fun. I wasn't hurting anyone.
Trully I felt joy so yes some of my first experiences in Girl clothes were some of my best.
If you had some fun memorable experiences of some of your first times in feminine apparel that you would like to share that would be great !

My first forays into women's garments had nothing to do with dressing as a girl. My mother and father were homophobic, so there was no chance either one of them would have initiated or tolerated any dressing in female clothing. My mother use to hang the laundry to dry in the hallway of our apartment. I had to pass by the clothesline to get to the bedroom wing. As I past by the clothesline I had to duck and weave through the drying laundry. I felt my mother's nylon slips and loved the feel of the fabric. Nylon was like none of my boy clothes. I must have been still under ten years old. I would caress the nylon. She also hanged the slips from a drying rack which was positioned over the bathtub. At first I use to leave the slips on the drying rack and slip as much of my body into a slip as possible. Eventually, I succumbed and began taking them down and trying them on in the bathroom. I also discovered her long nylon gown and tried that on also. In my bedroom that I shared with my slightly older brother there was a closet which had the dirty laundry bag. I would pull the nylon nightgown out of the laundry bag and slip into it under my bed covers. I always had to wait until I was sure my brother was asleep. I had no desire or longing to be a girl. It was just the feel of the fabric.

I was into bras and girdles and nylons and at age 7 my mothers fit me well enough. But one night I got into her pink baby doll nightie with matching frilly panties. I put them on over the bra and girdle and nylons and was I heaven! My first dress that fit was the one the neighborhood girls used to play Catch The Boy and Put a Dress on Him. I have told this way too many times but I used to get caught way more than the average neighborhood boys did. That old dress fit me like a glove. I was around 9 or 10.

For me at a young age it was about lingerie. That's what got me into this game. Finding some of my mum's stuff. A body, some knickers and some tights. They just felt so lovely to wear. When I was in my 20's I bought some more lingerie for myself and found that wearing stockings was a revelation. It's not until my 30's that I became interested in dresses and skirts and general outerwear. Now, I love the lot!

Being FULLY dress, undies and all, came about for me around 2006. (Remember I was born in 1943). Yes, I did do partials long before that, but never bras, panties, or hose. I loved the feel of the Materials. Soft and silky, not the male hart and thick male things.
But then in 2006. it happened. Two of my photo models did it to me as a lesson so that I would know what they went through to get ready for a photo shoot. I don't know were they got the heels in my size. I think I have one of those photos around here.
Will have to look in the over 100 CD. That is how I used to keep them. That was before DVD. Befor that it was floppies.

I'll never forget trying on my mom's nighties/lingerie for the first time, heaven!! A huge adrenaline rush!

I?ll never forget my first experience dressing. At a young age, one rainy day, next door sisters invited me to join them to play dress up. I?d never been asked or thought about it. At first, it was no big deal, until I slipped on a pair of nylon stockings. It was instantaneous. Next, I tried high heels. Fantastic. The rest is history.

Other than my wife's nightgown (I've related that story many times) putting on my first dress that fit was actually my own - and I still wear it! I took my own measurements, went online and bought a form fitting burgundy peplum pencil dress, the sort I always admired in others, to go with my heels and pantyhose I had purchased earlier. I slipped it on and it fit perfectly - almost. I needed breast forms and a hip shaper girdle to properly fill it out, so I got those - it was then both sensual and euphoric to put on, but wait - I needed a wig, so I got that, but then makeup to complete the look, and other dresses and different kinds of outfits...

and here we are today!

The first that actually fit?
Well that was some time ago. It was a chocolate brown, cowl neck dress with long sleeves and knee length. I mustered the courage and went to a shop that sold tall sizes and found it for $25. It was perfect !!
I wore it with my matching coffee lingerie including coffee pantyhose and 3" heels. I have to say I was in love with that dress. I'm sorry to say that a purge took it from me and I still wish I had it. I looked awesome in that dress.

The first 2 dresses I purchased fit but not well. They were a tad too tight. One was a maid's outfit and the other was a pink dress with bows. I bought them from Amazon and realized dresses needed to be bought in person. If they don't fit, returning them is easier. The 3rd dress I purchased fit quite well and remains my favorite dress. Of course, my wardrobe is limited to only 5 dresses. The dress that's my favorite is a black lace dress with 3/4 sleeves I purchased at Ross.

Like a lot of us, I started with lingerie, bathing suits, and leotards when I was about 12. The first dress I ever wore was a LBD of my stepmother's. I had a bra, panties, and stockings on with it and I had the bra stuffed with some of her shoulder pads (this was the 80s). When I saw myself in the mirror, I was completely stunned how absolutely gorgeous I looked and felt. There is no way I could pull off that look today so it is just a cherished memory. That being said, my own first dress was just this week. It was such a wonderful feeling to see that it fit and to see myself in it. I can't wait to fully dress in it.

Having played dress up from the age of five, I was 13 when I found myself home alone one Saturday evening. Knowing that this would be for the next 3 hours at least, I went into my sister's room and changed all of my clothes. This was the first time ever that I had dressed entirely as a girl. Leaving the bedroom I saw myself in a full length mirror, and that was my epiphany. From that day onwards I would dress at any and every opportunity. The rest is history.

My first one (and I still have it) is a black satin dress that has the appearence of being a wrap around dress but is not, free flowing and lovely to wear

Mom was a figure skater and had a closet of skating dresses. I spent so many hours standing in front of a mirror before anyone came home.

Christie, you lucky dog.
My mother was a Judy Garland look-a-like. Both were, height (4'.11") and weight (100 lb). but back then, I was a very short person. After mom and dad divorced, I started to grow. I went from 54" tall in 1956 to 72" in 1961. that is 18 inches in just 5 years.
I never wore out clothes, I just outgrew them. But I kept growing out in the middle.

I didn't have any females in the house that were my size, so my first dress was about 10 years ago. I had bought it at Target. Of course I didn't fill out the bust line so that was disappointing so I had to buy a bra, and then pantyhose and I just kept on rolling along!

Funny, I have memories of trying on different items of lingerie, but not a dress and I adore dresses.

I remember the first dress I put on when I was 12 or 13. My mom had 2 one baby blue and the other tan. Both alike except color. Anyway I called her to ask of she had a newer picture of my sister who had passed away at 19yrs old. My picture was her in 11th grade. So my mom sent me a large envelope with lots of pictures. One photo had her in that dress. Talk about crashing going down memory lane.

I had experienced pantyhose for a couple years when my dad bought the remnants of a group garage sale for us to sell at our home. There were any number of dresses in it, but it was a little dark purple dress -- I remember it so well; short puffy sleeves with elastic gathers at the ends, high neck, thin wavy white lace trim in a rectangular pattern on the chest, zipper close. I could put it on and zip it up all the way (with a short wire to help) and, while it was very short, it fit! Any others I tried didn't fit like that. That was the last time a dress with a zipper fit.

Quote:

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Originally Posted by Karren Hutton

I was into bras and girdles and nylons and at age 7 my mothers fit me well enough. But one night I got into her pink baby doll nightie with matching frilly panties. I put them on over the bra and girdle and nylons and was I heaven! My first dress that fit was the one the neighborhood girls used to play Catch The Boy and Put a Dress on Him. I have told this way too many times but I used to get caught way more than the average neighborhood boys did. That old dress fit me like a glove. I was around 9 or 10.

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LOL ! I believe for boys there is no coming back once you put on a silky babydoll nightie with panties with ruffles on the butt!

Well my first time wearing a dress was not an actual dress, but a cosplay outfit. I was wearing a Princess Peach outfit, a dress that covered me from the neck down, all the way past my feet. I knew darn well I was wearing something that was meant to be worn by women, even though I knew it was not an actual dress. I waited until no one was in the house, then I would dress up in it, with a blonde wig and all. The feelings I got from wearing this dress did indeed make me feel girly, feminine, and just plain good in general. At this pint in time I did not feel I was a crossdresser because it was only a costume, and the thought of wearing real women's clothes just did not appeal to me at the time.
It wasn't until I got my first real dress that things really began to fall into place and my true crossdressing journey began. When I put on my first dress, I felt real good about the woman in the mirror staring back at me. I realized right then and there that I was a crossdresser, and that there was no going back. Thinking about it only made me happier and excited, and I couldn't wait to buy more.

Alas I don't recall my first dress. Most likely belonged to my elder sister or one of my cousins. We used to all play dress up together when I was 6 or 7 ish. I have 5 cousins all girls and two sisters. Honestly, what chance did I have of not being a cross dresser with all that girly fun at such a young age. So lucky to be me.:battingeyelashes:

I remember about age 14 or 15 trying on my best friends moms bra's and panties
felt so good.

I am not sure I remember the first dress that fit, but I remember in my adolescence one of my sister’s that was the brand Gunne Sax. It was long and satiny and fit me well and I adored that dress and always enjoyed putting it on. It was one that she had only wore a few times for formal dances or such and she was off at college at the time, so it was “safe” in the upstairs closet.

Now, the informal/rebirth or sort of first again answer is a couple of months ago, as I posted early on here, there was a dress my wife ordered for a upcoming wedding that was sized too big, but fit me! Of course we returned it, but it instantly rekindled lots of feelings and ultimately led me to go online (never had that opportunity in the late 70s and early 80s) and step up my game and likewise discovered this site. That “first dress that fit” was about 40 years after the last one that truly fit.