The Moment of the Awakening - When was Yours?

[Anne2345]

Nothing is more precious than the innocence and wonder of childhood. With eyes wide open, brimming with curiosity, children are natural explorers. Many lifetimes ago, I was one such child, no different than any other. For the most part, I was a very happy child. I had a wonderful family, and although we did not have much, we had more than enough.

I have many fond memories from my childhood. Searching for tad poles down in the creek, catching lightning bugs during warm summer evenings, and catching falling snowflakes on my tongue, just to name a few. Of course, as I child, I absolutely LOVED Christmas! My belief in Santa Claus was unwavering, and I religiously mailed him a list of all the wonderfully exciting new toys that I just had to have.

We would travel to my grandparents’ home every Christmas, as would the families of my uncles and aunts. Without exception, it was always a family gathering, to be spent with loved ones that we rarely otherwise saw throughout the year. Not surprisingly, it was my favorite time of the year, and the closer it got to Christmas time, and the trip to my grandparents, the slower time seemed to travel. My anticipation and excitement was palpable, and could hardly be contained.

It was during one such Christmas vacation at my grandparents’ house, thick with the wonderful and distinctive smell of a freshly cut Christmas tree, that I was first introduced (albeit unintentionally so) to crossdressing. I was three and half years old. My parents, grandparents, aunts and uncles were enjoying some festive “adult” beverages while the children played. An aunt of mine, having a fantastic time herself, took me to the side, and began to paint my toe nails red. She thought it would make a cute joke. Playing along with her, I simply loved the attention she was giving me.

After a few minutes, my aunt finished her painting, advised me to be careful because it needed to dry, and with a sweet, loving smile on her face, asked me what I thought. I looked down at the results of her labor, and I was instantly struck by the color and beauty of my toes. Although quite young, I did have at least some small conception that nail polish was for girls. But instead of feeling embarrassed, I felt absolute joy in seeing my toe nails painted a bright, cheerful, and fantastically shiny color of red! I was SOOOO happy! My aunt called everyone in, paraded me around, and asked what they thought, thinking to elicit some good-natured laughs. She was quite successful in her endeavor, and all thought it was cute and funny. Shortly thereafter, I was called into the bathroom to have the polish removed. Of course, I complied, but with a heavy heart. In my child’s mind, I wanted to leave the polish on forever!

Although I did not recognize the portent at the time, I somehow knew I would never view the distinction between the two genders the same again. For me, the distinctions began to lose meaning and blur into an awareness of coalescing beauty and solace. From that moment on, I was hooked. Whether crossdressing is born from nature or nurture, I have no idea. But what I do know is that one moment of pure, blessed, innocent, wonderful joy I spent with my aunt was the Moment of the Awakening in me.

To this day, the memory is quite vivid and detailed. In fact, the memory is one of the earliest childhood memories I still retain. Before the taint of socialization, peer pressure, and conformity inevitably sank its teeth into my psyche, leaving behind indelible black wounds of self-doubt, denial, and obstinate confusion (which I have long since overcome, btw :)), I experienced the wonder and thrill of crossdressing through the innocent and curious eyes of a child. A child filled with an unadulterated love of life that had no conception of things to come, but whom anticipated the future with great excitement. This memory I treasure deeply and dearly. I shall never forget that wonderful moment in time with my aunt.

So when was the Moment of the Awakening for you? What gave rise to the recognition or acceptance that this gift of crossdressing was bestowed upon you? Was it one isolated moment that you can point to, or was it more of a gradual awakening?

[Karren H]

Awww. That's too cute!! I'm still waiting for mine! Sigh...

[Wendy_Marie]

I was around six and walked into my teenage Sisters room while she was changing into a new bra....I commented that I couldn't wait til I was old enough to get a bra and she laughed at me and told me that Boy's didn't have breasts and so didn't need a bra.
I ran out crying, Mom found me and asked what was wrong and I told her...she immediatley had dad have the "How boy's and Girl's are different.) talk with me. Again I ran away crying and yelled that he was lying to me.

[Debb]

My true awakening came when I was looking at old photos with my folks. I saw how "pretty" I was as a very young boy, and experienced this hollow feeling inside, as if I had missed my chance.

I'd been aware of my "difference" for a long time, but when I was looking at that photo of me, wrapped up in a silk throw, it was pretty much the same feeling that I used to get jumping out of airplanes. A blast of fresh air, so forceful that I could barely breathe, knowing how right it was.

It was awesome.

[Genifer Teal]

There are a few for me. The time I first tried on my sister's heels. They were a tight fit so I also put on a pair of her pantyhose. Then there is the first pair of serious heel which I bought myself. They were six inches high and I mastered them in a month. My most serious awakening was when I took off the wig. I had been CDing for a few years when someone suggested I try my own hair. It was real short but i gave it a try. I don't know what convinced me to keep it up at the time but I never put a wig on again since that day over 6 or 7 years ago. What a game changer that was. Everything became more real.

Gen

[Sophie86]

So when was the Moment of the Awakening for you?

I don't have a single moment like that. It's more like a series of incidents that all coalesced in that first time I became curious enough to willingly put on a pair a pair of panties. It's difficult for me to remember which of these happened first. I think I have them in the correct order, but the only thing I know for certain is that these all happened between the ages of five and ten.

The first time I wore panties, I didn't put them on willingly. All my underwear was in the dirty clothes, and my mom had me wear a pair of my sister's older ones. I was around five or six, I think. I knew that they were girls underwear, and I didn't want to wear them. She got exasperated, and told me it's just underwear. I put them on, and they felt weird. They made me very conscious of my genitals in a way that I had never been before. They also made me very self-conscious when my sister told her friend that I was wearing her underwear.

My mom kept her high heels in the hall closet. I remember pulling them out once because I wanted to see how it felt to wear them. It was interesting and a bit odd. The oddest part, though, was how angry my dad got. He made me take them off and put them back.

Sometime during second grade, I began refusing to get my hair cut. By the end of second grade, it was down to my shoulders. This was when boys typically wore their hair in buzzcuts with sidewalls. A few maybe let it grow down to the tops of their ears, but I had the longest hair of any boy in my elementary school for the rest of the time I was there. There were numerous incidents of being mistaken for a girl, including one time when a lady "miss" directed me, and I ended up in the wrong bathroom. My dad repeatedly tried to get me to let him take the clippers to it, but that was one battle I fought against him and won.

We used to watch the Flip Wilson Show, and I would imitate Geraldine Jones. "My name's Geraldine. I'm the cutest gal you've ever seen." The family thought it was very funny at first. Then my dad decided it wasn't funny, and made me stop.

I had a dream one night that I was a woman, and I had been in a car wreck and was hurt. For some reason the dream was very erotic.

When I was ten, my best friend's mother wanted him to dress up as a girl for Halloween. He was fighting her on it, so she called our house to see if I would dress up too to give him moral support. I had already dressed as Huckleberry Finn, and wasn't interested in spending the night intensely embarrassed. My older sister, though, was really taken with the idea, and she worked on me until I agreed to do it. She had me dress up in some of her older clothes, a pair of her go-go boots, and a platinum blond wig that my mom owned. Probably remembering that other time I had had to wear her underwear, I insisted on wearing my own. lol. It was an interesting night mainly because of what I didn't feel. I don't remember any feelings of eroticism, or girlishness. The only embarrassing moment came at the end. Somehow we had roped one other friend into joining us, and the three of us were walking alone a couple of blocks from my house. A carload of guys came by, and some jerk leaned out the window and yelled, "Hey, Baby!" at us. Not fun.

I do remember wondering whether I was attractive as a girl--more attractive than I was as a guy--and whether I would have been better off if I had been a girl. A seed was planted that would blossom a few years later, when I took that willing step.

[cassandra22]

in my time period of growing up,most girls wore dresses all the time,and i always loved catching a glimps of panties,my bad, i know.lol..anyway when i was 12, my uncle amd his kids came for a visit,my 12 yr old female cousin was very pretty and i always liked the clothes she wore,well they all went to my grandmas and left me on my own.i noticed her suitcase was open and saw the cute school girl kinda dress she had worn before,,i remember touching and smelling it and without a thought,i undressed,slipped on a pair of her panties and the dress and looked in the mirror,,i absolutely loved the feel and the way it made me look and ive been hooked ever since,and that was only 44 years ago.lol

[Miranda09]

Mine was really more of a gradual awakening, that took over 50 years to arrive at!!!! But I've arrived and that's all that matters. Loved your story Anne. I can just picture you with a broad smile as you showed off your toes. Thanks for sharing. :)

[Doodlen]

My story is a little different. Being biologically female, I wore female clothing. Usually my clothes were more androgynous, but I loved bright colours and crazy patterns. I almost always prefered guys clothes, but sometimes I just got in the mood to dress up girly (not dresses or skirts, just really nice women's formal-wear) and I loved it. But it felt... weird. And I couldn't put my finger on it. Usually I didn't like women's clothes, but it was like a fun game to play sometimes. And then one day I realized I was trans, and everything made sense. It just clicked.

[jessica renee]

I don't remember any one particular moment, but I do remember there were several times when I was caught when I was younger.

[Anne2345]

I'd been aware of my "difference" for a long time, but when I was looking at that photo of me, wrapped up in a silk throw, it was pretty much the same feeling that I used to get jumping out of airplanes. A blast of fresh air, so forceful that I could barely breathe, knowing how right it was.

It was awesome.

This is quite an amazing analogy! I love it! After reading your post, where do I sign up for skydiving lessons??!! :)

[Debra Russell]

My expierence was pretty much the same as Sophie's was. One time in high school (strict religious) a bunch of guys dressed in moo moo's for a joke on a Hawaiian day the school had -- they all got suspended, I wished I would have done it too! although none of them expected the suspension. I realized early-- about 3 yr I liked to wer my sisters silky slip, that "like" has never left..........Debra

[Debb]

This is quite an amazing analogy! I love it! After reading your post, where do I sign up for skydiving lessons??!! :)

Thanks. I was kinda trying to reflect your very nicely-written post.

Well, my initiation into skydiving was courtesy the US Air Force. Mind you, I still had to choose it, but it wasn't as they say the same thing as "real" skydiving. Lessons can be had at many smaller airports, and can be as expensive as say $400, or as inexpensive as probably $65 for a tethered jump (as you jump out of the plane, there is a tether that pulls your chute open).

[Cynthia Anne]

Anne, again you have written a beautiful thread that brings joy to my heart! I started thinking of my child hood as I was reading about yours! I guess my awakening was when I was four! My older sister would dress me up because she wanted a little sister to play with! I new then that I loved to wear dresses! I always loved playing' house' with her! Hugs!

[Frédérique]

Whether crossdressing is born from nature or nurture, I have no idea. But what I do know is that one moment of pure, blessed, innocent, wonderful joy I spent with my aunt was the Moment of the Awakening in me.

When I was about the same age as you, during your moment of awakening, I experimented with my aunt’s lipstick and makeup – she lived with us at the time, and, for some reason, I must have been fascinated with her cosmetics. This could have been a meaningful moment for little me, but my aunt was furious with this unannounced intrusion into her personal space. My mother quickly cleaned me up, and then protected me from her sister-in-law’s wrath, shoving the entire incident under the rug, but I remember this first “step” towards crossdressing with fondness...


So when was the Moment of the Awakening for you? What gave rise to the recognition or acceptance that this gift of crossdressing was bestowed upon you? Was it one isolated moment that you can point to, or was it more of a gradual awakening?

It was a gradual awakening, due to many factors that are too numerous to mention here, but I often think “what if...” If my sisters were closer to me in age, I may have been curious about their interesting clothing, especially if it was lying around somewhere. If I had been blessed with an aunt as a mentor, or if my sisters had one day come up with the idea of “playing” dress-up with their younger brother, or if one of my babysitters had a vivid imagination, I would have certainly been “awoken” much sooner. In the event, circumstances did not favor an early “coming-out,” and I regret this unfortunate wrinkle in reality every day. The opportunity simply did not present itself, but gradually, over time, my boyishness underwent a transformation that led me to crossdressing. Expression needs inspiration, and there were many sparks, all preserved as pleasant memories – I came to view crossdressing as a gift, even though I gave it to myself after a long period of self-evaluation. I really didn’t know that a boy, or a male, could do this, but once that idea became entrenched in my yearning mind, I definitely AWOKE...
:)