Crossdressing memories

[Paula_56]

I couldn’t sleep the other night so I began to remember, trying to find the earliest recollection, of being transgendered. These are some of the experiences that ran thru my mind. It helps to share them with others who might have had similar experiences. Please feel free to comment or share your own thoughts or experiences. These times and events bond us together into a community

I remember being very young and watching my Mom get ready for work putting on her make-up and doing her hair, the smell of lipstick and hair spray are comforting and bring me back to this time.

I thought about the wedding I went to when I was 5 years old and became so jealous of the flower girl; I still remember that yellow dress.

My first communion, wishing I was on the girl’s side wearing one of those pretty white dresses, praying the host would magically transform me into a girl.

Watching the girls in 2-3 grades go to ballet class after school and thinking why can’t that be me?

When I was 7 or 8 years old seeing a young boy dressed as a girl at a Halloween party and me becoming jealous, I still remember the beautiful, bouffant pink dress, with black Mary-Janes and white tights. He truly wasn’t happy about how cute he looked, Oh I wish I could have taken his place.

It was the spring of 1968, I know because we just got our new car, I was 9 years old and one Saturday morning I went down into my sister’s room and dressed her clothes. It was the first time I dressed as a girl. I knew I was a girl, at that moment, I knew I had to find a why to make everybody understand.

Coming home to an empty house and dressing in my Mom’s and sisters clothes from age 9 until 18.

Having crushes on girls and wishing I could be them or like them.

Feeling embarrassed changing in a locker room full of men

Feeling elated when an Aunt told me light heartedly that I would have made a wonderful girl.

Going to a go-go bar with my friends and feeling sorry for the way the women were being treated.

At 19 years old dressing as a woman for a Halloween party when I was stationed in Germany, and then making out with a guy on a couch in the basement. Holy Shit!

Cashing my first paycheck at 22 years old, and then next thing I know I had bought, pretty black dress with a white collar, pleaded skirt and red bow, and the cutest pair of patent leather pumps, with a 1 ½” heel and a bow in front.

Feeling confused and anxious when I married

Being devastated when my wife called me a pervert.

Finding the internet, and communicating with other transgendered people.

Shaving my legs for the first time

Saving $5.00 a week so I could get a make-up lesson at Vernon’s in Waltham Ma.

Being ecstatic when my wife showed the least bit of acceptance

Getting a Jamie Austin make-over Wow!

Sneaking my clothes out of the house for a business trip

My first time thru a shopping mall in Florida, a black pants suit, cute shoes, and blonde hair.

Working from home one day a week and doing it as a woman

Laying in bed sleepless, wondering……………………………

[Cristi]

I often go over a similar list in my head to try to remember all the landmarks I've passed as I've grown.

I won't do the entire list here, just he earliest memory. It is one of two things and I can't place which was the earliest.

First is watching my two sisters who'd just been given 'party dresses' (the kind of lacy princess dresses 7-8 year old girls love to play in). They got all dressed up in the dresses, tights, fancy shoes, etc and went on a 'parade' through our yard and out onto the street. I was just in my normal clothes and remember feeling extremely jealous as I followed along behind them. I don't think I'd dressed at all by this age, or was even aware of the desire... but that feeling of jealousy was surely the beginning. I think I was only 5-6 at the time.

Second (or MAYBE it happened before?) was a halloween around the same time. My mom dressed me as a 'little old lady' in a black dress, black tights, heels and a gray wig. I remember going out to a neighborhood halloween party in the outfit. A few of my only clear memories of the event are constantly tripping on the hem of the dress, which was too long, and also constantly having to pull the tights back up which means they probably belonged to one of my older sisters and were not the right size.

[tricia_uktv]

Hi Paula, I don't know how easy it is but why not go out and live it! I have forgotten the memoties now because I am Tricia. I promise it will change your life.

[Paula_56]

Tricia I am trying, this week I go to Denver on business, and plan on getting out as Paula first to a support group meeting and then shopping

thanks Paula

[Karren H]

I remember the girls in the neighborhood playing "Catch a boy and put a dress on him". I also remember not being the slowest runner but getting caught way more times than any other boy on the block.. "Ohhh noooo.. Don't put that dress on me again!" Lol.

[tinalynn]

So many memories... Every time I had an empty house my sister's and/or mom's closets were raided. Sometimes I would go outside in the backyard, which was fairly secluded, and walk around the small patio just to feel the wind and hear the sound of my heels click-clacking. Even in the Michigan winter I'd head outside to feel the snow through pantyhose! The times I was caught stand out to me - my brother finding me twice, once hiding under the bed, the other time I was hiding in the closet (go figure!). The cops stopping while I was walking past my parked car on a lonely country road, and asking why I "stole" my mother's clothing. I thought I was heading off to the local lock-up for that one, but they were just giving me the business. Walking hotel hallways on business trips without the wigs and make up wondering to myself 'why am I doing this?'...

Because it feels so good and makes for fond memories.

[Toni_Lynn]

I have had many of the same memories as Paula. Here's my list with some no doubt forgotten at the moment

Watch Bug Bunny as child and seeing him dressed as a girl, and wishing I could do the same

Going to a circus at age 7 with my dad and seeing a magician, and if I could volunteer if he asked for participants from the audience, in the hope that he would turn me into a girl

Using the girls restroom at school for the first time at age 8 while in grade 3.

Seeing other boys come around at Halloween dressed as girls and wondering why I wasn't that lucky.

Trying on my sister's panties at age 11

Getting my first bra and panties -- MINE! not someone elses -- at age 13 -- and wearing said same to school under my boy clothes.

Going to a boy scout Halloween party at age 14 and seeing one of the other scout in a girl scout uniform -- and him showing us that he was wearing a training bra -- just like one that I had! And the fact that he was proud of it!

I too dreamed of the different girls at school, being their boyfriend and dressing up with them

Getting caught, and abused by my mum, and burning everything, and then going out and buying it all again. Lather rinse repeat over the course of 7 years.

Joining a group at age 26 or so -- going out in public for the very first time, getting read, and purging .. then buying everything again

Finding my lost self at age 31, and beginning the adventure of a lifetime, that included:
-a few makeovers
-going shopping with an FTM friend
-a highly unsatisfactory visit to a pay for play girl in NYC to play gender games
-meeting my first wife and telling her on the day we separated about me
-meeting the woman I am now married to -- who makes all my crossdressing dreams come true

Huggles

Toni-Lynn

[Janine cd]

My first memory of wanting to dress as a girl was at a birthday party for a girl cousin. She had an autographed photo of a child radio actress named Bobbie.
I had heard the radio show many times before and thought that Bobbie was a boy.
When I saw the picture of a beautiful young girl in a lace pinafore dress with patent leather mary jane shoes my first impression was that a boy named Bobbie was able to be dress the way I had wished to do.
Iwas only 5 at the time, but I kept wishing that this could happen to me.

[cdjenny20]

I think my earliest crossdressing memory comes from when I was about 5 or 6 and watching my sister in a ballet class. I remember sitting there and wishing I could have worn the same things as they were wearing.