Crossdressers-Haven.com

It's still seared in my mind, even though it was many years ago. Not sure how old I was, except that I was preschool age, probably 4 year's old. I had seen a TV show the night before in which a boy wound up wearing a dress. I was fascinated by that and that night I dreamed about me being in that dress .

Sometime the next morning I went to the drawer where my mother kept her lingerie. We lived in a small flat and her lingerie drawer was in the same room that we had our TV. Any way, I took out a girdle.. one of those open bottom girdles that I still adore. I stepped into it and I remember feeling a rush of excitement as I did so. Of course it was too big and fell to the floor. Just then, my mother and grandmother, who lived upstairs, walked in on me.

They both burst into laughter and I remember my grandmother saying th it was my mother that needed a girdle, not me. I was mortified that they laughed at me and that started me on my path of secret dressing and fantasy. I didn't want to be caught again.... although at that age, I had a lot to learn about secrecy.

It must have been the first time I put on her lipstick. Wow what a feeling. I wiped it off on a towel in the bathroom and didn't do a good job of it. My lips still had some red on them and my mother asked me why they were red. I told her I had just eaten a cherry lollipop. Good thinking, LJ..... she never said anything after that but I always wondered what she thought when she saw the towel.

My early years were filled with such forays into the feminine world and they wound up being fueled by my mother's friends always saying that I was too pretty to be a boy. That really played on my psyche.

To be continued....... thanks for listening.

Laura,
Funny thing you mention seem like yesterday, I too to this day feel like it was just yesterday when I was 14 my mother walking in on me one Saturday when she was supposed to be at work all day.

There I was all dressed up from head to toe in her cloths and a face full of makeup and I still can hear to this day her words, "young lady take off my good dress" .

Welcome Laura, Nice to meet you and look forward to hearing more

Hugs,

Erica

Love the story Laura Jane! Isn't amazing how we all remember that first time like it was yesterday even though for some of us it was a long time ago.

Continuing the tale....

So there I was a little guy....... wanting to be a little girl. I mentioned in my first post that some of mom's friends told me I was too pretty to be a boy. I. Actually started to feel guilty about being a boy especially after hearing Mrs. K who lived across the street. It's the way she said it....... maybe my mother told her about my affinity for wearing her lipstick... l'll never know.

Of course, inside I loved to hear how pretty I was. One family friend used to tell my mother in my presence how she would like to have me spend a weekend at her house and she would pretty me up. OMG..... how I wished that would come to pass. Outwardly I feigned disinterest.... but inwardly I was dieing... knowing that it would never come to pass. It was the source of many fantasies over the years as I pictured myself being taken shopping for frilly dresses and nightgowns..... maybe even a makeover and a wig and my very own silky panties. Oh how I longed to be Mrs. S's little girl. I was probably six or seven about this time.

I spent my formative years dressing whenever I could get my hands on my mom's clothes. She had a slinky blue dress with white polka dots that I really loved. I can still remember the thrill of slipping that dress on.

I have many remembrances to share, but am afraid I may be getting too detailed.Suffice it to say that I thought about being a girl almost every day. These are my collective beginnings through mygrade school days. My fifth grade teacher once told me in front of the whole class that she would like to put a ribbon in my hair and put red lipstick on me, . Promises.... promises. Humiliating and thrilling at the same time. I will continue tomorrow if OK.

Thanks again for listening. This is very cathartic for me.

Thank you for your story Laura. I look forward to the next exciting instalment.

As I do too...

Hugs,

Erica

Thanks girls for the nice words

As I grew up I continued to look for every opportunity to dress... with some close calls. To be honest, I secretly wished I was caught, but always managed to stay one step ahead (as far as I know).

I got older and bolder and eventually became familiar with all the drawers and closets where my mom kept her things. One afternoon, my parents and older brother were out... can't remember if my sister was born yet, but there I was in all my finery... my favorite blue/white polka dot dress, full makeup, heels, jewelry, lingerie... the works (no wig yet.... that would take years I wore a kerchief instead). In my mind's eye. I was looking rather beautiful and I was feeling very good.

As I mentioned, my grandparents lived on the second floor of our house and the doors were always open. There was free movement up and downstairs and lo and behold, my grand father walked in to read the afternoon papers. I heard the door opening and closed the door to my mom and dad's room where I was. Their bedroom was between the rest of the house and the living room where the TV was. If my grandfather wanted to watch some TV by himself which he had done on occasion...... he and I would have gotten he surprises of our lives......

I was panicky at first but then relaxed, resolved that I was going to be found out... and I was suddenly OK with that. I stood there, making no effort to wipe off makeup or change my clothes, straightening out my dress, waiting for the inevitable. Well... he finished with the paper and went back upstairs.... no such drama that day. I often wondered how things would have turned out if he walked in on the granddaughter he didn't know that he had. What would have changed in my life? I think it may have been life altering. Certainly my desire to dress would be out in the open... no hiding from the fact given the state I was in.

Another time, I was alone and in the bathroom painting my nails..... maybe 11 or 12 y/o. I just finished and who walks in the house, but my grandmother. I heard her go into the living room and turn on the TV. I hollered out hi to her and sat there momentarily determining that I would go into the living room with my red painted nails and showing them to her. I came very close to doing that.... but finally nixed the idea. I took off the nail polish and went out to say hi to her. My grandmother might have been the one who might have understood... but again.... I'll never know. Was this a lost opportunity? In retrospect, I think yes.

Like many of us, I suppose, I condemned myself to a lonely agony / ecstasy scenario ..... not really understanding what was happening and thinking that I was all alone in the world with my predilections.

Talk about missed opportunities....... One Halloween, I wasn't planning on trick or treating. I think I was in the 6th or 7th grade and thought that I had outgrown it. Our next door neighbors were good family friends,,,, in our neighborhood, we all knew one another, all the kids went to the same Catholic school, which was a block away from my house and generally all the neighbors were pretty close. The next door family had a son and a daughter and I called their mom Aunt Jean. I was friends with the boy, who was two years younger than I was. Aunt Jean wondered why I wasn't going trick or treating. I told her my mom was napping and I didn't feel like going anyway. She then took me completely off guard when she said.... "gee, we could dress you up like a girl".... I've got a fancy dress and all, etc... etc." My head exploded inside... all white lights and all.... OMG... what a thrill it would be..." But NO...... the rational side of my brain said that I was going to be found out... that there would be no way for me to hide the fact that I enjoyed wearing the dress and looking pretty. I had to avoid that at all costs.... so I declined. UGH..... to this day I regret that.

To absolutely add insult to injury, a couple years later on Halloween, some pretty girl knocks on the door and says "Trick or Treat". I answered the door and didn't suspect at all that it was my friend from next door, wearing the dress, I'm sure that I would have worn. Oh well....

Talk to you all later. kisses...... LJ

(If this is too much, or should be in another thread, I hope the admins will let me know)

Hey Laura! It was great chatting to you this evening!

On reading your posts I really notice there being a thrill of being caught! I've often wondered about that theme. It seems to me that we dearly want to be recognised for who we really are - but it's risky isn't it!

Anyhoo - welcome to the forum!

Hugs Ginny xxx

What an amazing list of paths not taken, Laural. Opportunities left in the dust.

Everyone has regrets, but you really can choose which regrets to have: the regret of trying and having it not work out, or of not trying and never knowing.

I feel like you are asking permission to try.

You have my permission.

Just to get totally selfish, these are great posts to read. Do as many as you like, Laura.

On the subject of regret and paths not taken...When I was 9 I was selected to play Titania in the school play. I was kind of pretty as a boy.

So I did it and did have fun. And the local paper wrote it up and said I made a convincing girl. But...

Afterwards I lost the two friends I had and everyone was kind of chilly towards me. It lasted about 2 years, until I got into the school rugby team and, I guess, people were thinking about me in terms of that rather than someone who was a bit too convincing as a girl.

I kind of wish I hadn't played the role.