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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My first excursion into crossdressing was when I was just eight years old. Though I can remember wondering about it from a much younger age, I tried on my first dress one day when I was home alone. I was blessed enough to have an older sister as well as a younger, the latter being born just a year after myself, so I had an ample supply of clothes that were nearly, if not exactly, my size. That first dress though, I remember like it was yesterday. The feel of the cotton nylon blend, the way it stretched and silloetted… Read more »
Like I said earlier here I didn’t get to wear my first dress til I was 11.
My mother believed boys and girls could and should wear dresses. She said all children look nice in dresses as opposed to pants which wrinkled or bunched or became tattered along the cuffs, especially if the pants wouldn’t sit properly on the body. My first dress was yellow with flowers along the bottom hem trimmed in lace. I loved it. Over the next five years my mother supplied me with lots of dresses.
Whether it was helping my mother by attaching her back garters to her stockings[arthritus],and then her helping me explore what stockings felt like on my legs[an old pair with runs]I was curious early on.And,I too had that hidden stash of old dresses in tha attic and loved to secretly put them on. My sister was[is] 4 yrs older and I was always looking to grab some of her discards….By junior high,I was feeling very jealous of what the girls got to wear.and had my hidden stash of tights,leotards,etc..But,we all go through those years and usually can't tell anyone about it.Sometimes… Read more »
I have had a few opportunities, from playing with my sister's barbie dolls and wishing I could try on her leotard from when she was in ballet to cooking oatmeal cookies with my gram. I also succinctly remember that I hung around my sister's girl scout troupe a lot when I was little. I had participated in a lot of the activities and their meetings were usually a lot more fun than my boy scout outings. I remember being very disappointed with all of the toys I got for birthdays and holidays because they were usually traditionally masculine toys –… Read more »
I was always big, and I had a little sister and a very small woman for a mother. My first memory of trying to dress that I can recall is that I couldn't even fit in any of their things because I was too big.
I must have been 12 or so. I don't remember much before that.
At age three, two older neighbor girls constantly were dressing me up as a girl, by 6 I progressed to bras and panties and girdles of my mothers. Whenever I was over to a friends house to play, say age 7 to 11, I would excuse myself to use the bathroom and would sneak into his mothers room and try on her bras and panties and nylons. Then one time playing with two sisters, we took turns playing you show me yours and I'll show you mine. I remember looking at them naked and thinking "why can't I have what… Read more »
With me it started then I was about five or six years old. I found a pair of woman’s pink gloves in a draw. I put them on just for the fun of it. I found myself imaging that I had been transformed into a beautiful girl wearing a lovely pink prom dress with my hair done all up.
Part one: Hello again, I know I wrote recently concerning how it all began for me. I have been thinking lately…and trying to disect my exact feelings and thoughts during those first times. I would really appreciate it, if perhaps Vanessa, after reading my own thoughts would comment with her own. I know a boy of five or six has little if any sexual interest. Yes, he might begin to feel those itching sensations down below, but has no knowledge of what they mean, only if touched or rubbled, it feels good. I remember when I first viewed my cousin… Read more »
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… Read more »
Part three My feelings then as I know now, were of extreme anxiety, butterflys again, and a very large guilt feeling..knowing I was again about to do something wrong. But, none of those feeling stopped me…none!!! Once I approached the drawer, opened it and saw all that I had thought of for so long (three days) My hands ran over the nylon panties, bras, and other items..and for the first time, I felt that tickling feeling between my legs. I do remember rubbing myself, just once, because again, I was doing something that was wrong. My mother had told me… Read more »