Transsexual - In the beginning

To get where you’re going it’s critical to know where you are, and often helpful to know where you’ve been. I must confess that much of my childhood is shrouded in the fog of memory, but I will strive to share those moments which shine brightest in my mind’s eye.

Crossdressing at Age Five

My earliest memory of being different was when I was about five years old. I can remember it as if it was yesterday. I was besotted with the idea that I would wear my mother’s nightie to bed, yet knew that this desire was wrong. At such a tender age I have no idea how I knew that it would be frowned on, though I’ve heard other ladies say that they were similarly aware at a young age.

As much as a five year old could, I hatched a plan. Early in the evening I would smuggle my mom’s nightie from her room and hide it in the hallway closet. When she came to check on me before going to bed I would pretend to be sleeping, and then wait the torturously long while until my parents went to bed. Once they were soundly asleep I would sneak out to get the nightie, put it on and enjoy a night of bliss.

I must say that I’m quite surprised my plan went off without a hitch, and the next morning I changed back and reversed the “nightie from mom’s room to hallway closet” routine. I remember feelings of anticipation, excitement and then a deep abiding calm as I drifted off to sleep in her nightie.

Crossdressing in Bathing Suits

Still in early childhood I recall one day when a neighborhood girl came to play and then sleep over. In the afternoon sunshine I convinced her to trade bathing suits before running to the pool and jumping in. We bounced around in the water, and I remember loving every moment of it. I was scared that my mom would think something was amiss, yet delighted when she noticed our swap with what I can only imagine was a joyful laugh at the innocence of youth.

Later in the evening we tried to swap pajamas, but the lack of any expandable material in hers meant they didn’t fit. I grudgingly spent the night in my own PJs. My first blocked crossdressing moment, and transgender disappointment…

Crossdressing Party – It’s Allowed!

One of my fondest crossdressing memory came not too many years after the bathing suit event. I’m not sure how old I was, at best I can remember I was about nine or ten. A neighborhood girl (she who was generous with her bathing suit) was throwing a “Crossdressing Party” for her birthday. Everyone had to come crossdressed as the opposite gender, and I went as a Hawaiian hula girl, complete with grassy skirt and appropriate chest coverings.

I had died and gone to heaven and then died again and gone to heaven’s heaven. I still remember my mom telling my to “sway my hips” as we walked around their pool for the final judging. I ended up winning the prize for “best crossdressed boy” (the girls had a similar prize). I don’t recall how I acted after that, though I suspect a combination of hesitant joy and uninterested aloofness. Crossdressing was a fun thing to laugh about, not something to truly enjoy…

All I Want For Christmas

The last memory from my childhood was about a Christmas wish almost fulfilled. Like many youngsters we wrote letters to Santa asking him in our most polite and grateful way what we would like for Christmas. As was routine, we would write the letter, mom would read it and then we’d put it in an envelope and mail it to the North Pole.

I couldn’t have been much older than eleven, when I remember desperately wanting a dress for Christmas. Somehow I knew that telling my mom I wanted a dress was not a wise course of action. I had planned to wait until after she read my Christmas list and then discretely add “A Dress” at the end of the list before mailing it to Santa. After all, what harm could come if Santa brought me a dress? It would be Santa’s fault, not mine.

Unfortunately I chickened out at the last minute. I’m not sure why – perhaps I was afraid that Santa would tell my parents, or that mom would take one last look at the list before I could safely wrap it in an envelope. Whatever the reason, I remember a sense of lost opportunity that Christmas morning despite my abundance of gifts that included a really neat Capsela building kit [Hey, I’ve always been a geek in my feminine heart…]

The rest of my early childhood fades back into time. I vaguely remember times I sat longingly watching my mom applying makeup. Perhaps it was just an imagined fantasy, but I seem to recall her doing my hair or letting me play with her makeup. Things would only get more interesting when I took my first tentative steps into adolescence…

What memories do you have of your early crossdressing childhood?

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40 Comments
  1. Nikki 9 months ago

    your story was so touching and nice to hear. I am glad you have such positive experiences. The crossdressing party does sound like a dream come true. I bet it was so much fun to win that prize. It sounds like it almost vindication for you. Thanks again for the story,

    Nikki

  2. Jas 1 year ago

    Thank you Vanessa, I needed to read that first part of your article.

    “To get where you’re going it’s critical to know where you are, and often helpful to know where you’ve been”

    Love the story, I smiled reading the whole thing. Your probably right Santa would have told on you. I bet you thought about it from time to time, how happy you would have been to open a present and see a beautiful dress.

  3. Tommy 2 years ago

    Well the earliest I remember,i was around 8.. my Granny had 2 little girl frilly dresses and panty hose in a drawer. We were allowed to dress up as girls
    I thought I was pretty girl and loved every chance to wear that dress..I only recently after 30 years started going out publicly. It’s not easy I fight the urge to hide the beautiful loving girl on the inside.but am relieved after the fear passes.. I feel total calm.

  4. Why Am I Here? 2 years ago

    […] inside of me. Through the years I explored many aspects of my journey, sharing my first times pondering whether I was transsexual, beginning to take hormones, and sharing some of my thoughts after my […]

  5. Skylar 6 years ago

    I was about 7 and had my sisters pantyhose and a pair of my moms panties on one nite and got caught. Not to fun for me, but years later( 15-16) I would wear my moms panties and bras and shoes and look at my nice butt in the mirrors in the living room and masturbate. I have always known I shouldhave been a girl but girls always loved to dress me and have sex. I am very bisexual and the girls love it! Crazy stuff! I have a great gf who loves to buy panties we can share and have even been on a sex trip with others. I guess I am one of the lucky ones!! I love to wear womens clothes and lingerie It makes me feel complete as a person!

  6. berry cleanser 7 years ago

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  7. Kay 7 years ago

    My earliest story is this: The girl next door would come over and play house with my brother, who is one year older. They were the Mom and Dad and I was the baby girl. This was definitely pre-school, so I;m guessing that I was about 4. I found a little nightgown that one of sisters must of had and ran around the back yard. Maybe, someone said something, because after that I always dressed in secret and was never caught. Except maybe once, The family were all in an enclosed porch watching TV. It was a hot summer night. I went upstairs to my sisters room where one of had a cute bikini that I was dying to try on. I might have been 12-13. I put it on, slipped a bathrobe over it, exited the front door, walked around to the back, disrobed and dived into the pool. Anyone could have heard me and maybe decided to join me and I would have been trapped with no place to hide. But no one did. After my swim I reversed the process and returned to the family room. The phone rang. They asked for me. girl, maybe the one who lived behind us, said, "I saw you" and hung up. Another word was never spoken.
    Kay

  8. Leslee 7 years ago

    Wow ,so many good stories. I remember having a poem read to me about how girls were made of sugar and spice and everything nice. I was about 3 years old and I just came right out and asked my mother when could I become a girl. She really didnt know how to answer that but I soon started wearing items here and there of my moms. By age 7-8 I had purchased a few items of female cloths and was regularly wearing panties and nylons under my male cloths. She found them but alowed me to have them anyway. I remember having her say I was her special child once and I knew exactly what she was saying. I never did like sports like my brother but would much rather have engaged in more female activities.

    • Vanessa Law 7 years ago

      Wow! That's an early start, so wonderful your mom was so supportive 🙂

  9. Jillian 7 years ago

    Part two:
    This experience that night only last ed no more then perhaps three or four minutes…but in those minutes, I think my whole life changed…and to think it happened so quickly. From there as I wrote, my only thoughts were to somehow get to open my cousins lingerie drawer and look..it was like a driving force..even at six years old…those thoughts dominated me all day long, until I found the courage to wait for the chance to go into their room. How many times did i start and stop going into that room that held all that I ever wanted to see

  10. Laura 7 years ago

    Ya know, it's hard to tell which truly came FIRST, but I remember all of my early experiences VERY clearly. Up until 6th grade or so, my 2 best friends were girls. One day we'd play with my cars, the next day, we'd play girly stuff (play house, Barbie's, whatever.) I remember my one friend was big into dance, and for some reason one day I became obsessed with this pink tutu she had and I insisted on trying it on. I remember walking around her house with it on, but yet the full time somehow feeling that it was "wrong". I was probably 5 or 6 at the time. I also remember taking naps in the afternoon and to pass the time while I was supposed to be napping, I'd sneak into my mom's room, grab some of her underwear, put it on, and dance around. It was all too big for me still (my mom is tiny too, so i must've been REALLY young.) I didn't know WHY I liked it, I just did. Over the years, especially as I got older and could be left home alone, I'd fake being sick so I could stay home from school, have the house to myself, and dress up all day.

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