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. Stace 8 years ago

    I'm busy writing my life CV for my therapist. I've just finished the childhood section (all 4 pages of it…) Once you start it's amazing what comes back to you. Memories trigger other memories and a chain reaction forms.

    I've known from my earliest memories that something was wrong, and like you also knew at that time that it would be frowned upon. In a recent conversation with my mum she said she wished I had told her then so something could be done about it at the papropriate age. How she would have actually reacted 30 years ago I don't know – but it was lovely to hear that from her at least 🙂

    Stace

    • Racquel Lynn 8 years ago

      I knew as early as 2 or 3 years old that I should have been a girl, if not before that. Once I met my ex-wife, who was wonderful and supportive. We could tell eachother anything and I felt very comfortable and safe about coming out to her. I had told a couple of friends in high school, though I really wasn't "coming out" then, but this was the first girl I had been in a relationship with that I had ever told. It was early on in our relationship and before we had gotten married. She knew and still married me and we were married nearly 10 years.

      • Racquel Lynn 8 years ago

        When I realized that I could not hold back and deny myself from being me any longer, I decided to start keeping a Journal and documenting all events related to my gender identity and transformation. It could be coming out to someone and describing their reaction, or just my feelings that day, experiences I had while going out dressed as a female and how people treated me, or how it made me feel being out as myself, etc.
        I also will often just sit and write about things I would recall growing up. Feelings I had that I should have been born a girl, thoughts I had, sneaking into my mothers dresser and putting on her panty hose and other such items…sometimes getting caught…, times I was able to dress up (such as for halloween) when no one would think anything of it.

      • Racquel Lynn 8 years ago

        I have a few memories that really stick out all the time, even to this day, but then I try to think about all the things that happened or thoughts and feelings I had when I was young and usually the same ones keep popping up and I think maybe I don't have much to bring up about that, because I have always had these feelings, so putting them in my journal would just be rehashing the same thing and be boring to read. But then once I start writing I will start bringing up memories of things I had not thought of in many years, so I start writing more and then I start remembering more.
        So, I agree, once you start writing and thinking about things, so many other things will come back to you and trigger memories of even more things.

    • Vanessa Law 8 years ago

      Hi Stace,

      Indeed – the mind is a funny things, once jogged it's like a flood of childhood opens up. It's interesting that you had the same inclination to hide it, even at such a young age.

      Dear, I'm so pleased that your mom took it well – you're a blessed woman!

  2. Veronica 8 years ago

    I remember the first time I ever crossdressed is when I was six years old. Saw some panties on the clothesline, got them down and went into a field to try them on. My life changed from that moment on.

    After the first time I wore the panties I tried pantyhose. Liked those a lot better. Still remember having to crawl them up my leg cause I didn't know how to properly put them on. It was a year or two when I saw my mom putting them on that I figured out how to put them on correct. After the pantyhose I then tried full slips and then eventually dresses when I got older.

    It was hard to crossdress when growing up. I almost never had any free time to dress up until I was about eleven or twelve. But when I was alone for a period of time, I wore a dress with all the accersories. 🙂

    I now know that my mom knew but she never said anything. Even thought about one time getting all dressed up and having my mom see me just to know what she would say, but I didn't do it. I sometimes reget this now.

    Sorry for the long comment and may God Bless.

    Veronica =)

    • Arthur 8 years ago

      Hi gurls, I can remember when I was about 5 yers old…coming home from school, knowing my mother was putting my sibling to sleep. I would get my mothers bras, panties and put them on…even her dresses. Today I know that I'm a woman who needs to get out and be me….

    • Vanessa Law 8 years ago

      Lovely to hear Veronica, and even more lovely that your mom knew and let you continue. What a blessing!

  3. Jack 8 years ago

    Actually I'm 15 right now and cant find much of any way to crossdress. My mom wears only plus-sizes and too-small shoes. All I can do is wear makeup when I'm home alone and wear nailpolish on my toes under socks. I need any suggestions. The woman inside me is fighting to get out and is dieing from the struggle. HELP ME LET HER OUT!

    • Melphina 8 years ago

      Adolescent crossdressing isn’t easy, Jack, but if you look hard enough, most communities have a youth transgender community, and quite a few have meetings and programs with which to get involved. Not being one to suggest sneaking out or anything, but it’s how I coped with it at my age. If your community is less accepting of the trans community, or you just feel the need to hide in plain sight, 24 hour stores are great for trans clothes shopping. On more than one occassion I have purchased Items during the wee hours of the morning at a Walmart, ect. and the cashiers usually laugh it off as you being on a dare. Hope some of this is helpful.

    • jeri 8 years ago

      jack save some money and go to wallmart in the womens ware and try on pants and dresses ,bras , ect. find out your sizes then go to romans or within to bye your clothes

  4. Racquel Lynn 8 years ago

    I remember when I was really young that I used to have tights. I know I have always felt that I should have been a girl and always wanted to dress female, but never could really tell anyone. Although it was so long ago, I know I used to like wearing them and I knew (even if I didn't conciously realize) that they were feminine and that is why I wore them. I am not sure, but it seems like maybe I may have thrown a tantrum because I wanted them because my friends (who were girls) wore them and I wanted some too. Maybe one day I will find out if that was the case. lol But I do remember I had some blue tights and some white ones. I was really young then. I also remember being caught a few times dressing in my mothers panty hose and other things.

    • Racquel Lynn 8 years ago

      I also remember a couple of halloweens growing up that I dressed as a girl, but not how I would have liked. My "costume" looked too much like a costume. I had wanted to look like a real girl, but people trying to help me put it together and with what I had to work with, putting on a rediculous looking wig, someone else picking out a dress that I didn't like and let's not even talk about how bad the make-up job looked! The heels weren't bad and I enjoyed the bra I was wearing, and at that point, if I could even enjoy that much and at least have a night wearing a dress, even if it was hidious, I would take what I could and be greatful. It just would have been nice to have looked like an actual female and be recognized and accepted as such instead of just a guy in a funny girl costume.

  5. Robert (melodie) 8 years ago

    I unfortunately, never had a girls soft complexion. Even though I am transgendered, I don’t look like a girl/woman when dressed. Maybe it is because of my English heritage, I don’t know. My first recognition of
    feelings for feminie attire was when I was shopping with my mother. I was about 5 maybe 6. We had gone into the store and my mother was to get something for my little sister. I was in awe at the selections available, the colors and got this feeling that this is where I should be.
    I touched some of the clothing. The dresses, skirts and decorated panties seemed to be callling me, to be my true self. Of course the argument in my mind was this wasn’t right, boys were not suppose to like girls clothing, RIGHT. This feeling overwhelmed me on several other shopping incursions. I didn’t really get to wear my first dress til I was 11, but I knew from earlier I was different.

  6. Jillian 8 years ago

    My first memory of crossdressing, or feeling that I was different, involved two of my girl cousins, one twelve, the other fourteen. I was very close to them, our houses were in walking distance. I remember being taught girls games, Jacks, skip rope, pretending to cook on one of those toy stoves. I had boy friends, but spent much more time with my cousins when they were home from school. There were many times when my aunt would watch me while my mother and father had someting to do…and if they were going to be late coming home, I would spend the night with my cousins. Beings there was only two bedrooms, I slept in my cousins bed, in between them. I never really thought much about it, until one time my cousin thought I was asleep and began to undress..not entirerly, but down to her bra and panties. I rmemeber keeping my eyes barely closed and looking at her panties, how soft and silky they seemed to be, looking at her bra, with the straps and back band. That was my beginning in a younng boys interest in girls panties, and bra's. From there, I would sneak in their room and look at their panties and other items of lingerie. (first part)

  7. Jillian 8 years ago

    (second part)
    Finally one day i got up nerve to take a pair of panties into the bathroom, wonderous at their feeling, seeing the elastics bands, looking at the tiny sown in tab…..and finally stripping off my own pants and shorts, and having my breath taken away from me..for those few glorious moments. That was my beginning. From there it became something I couldn't stop, nor did I want to. I learned so many things, feminine ways of doing things, the correct way, from just watching my cousins, and of course, their friends. I never wanted anything more, then to become feminine.
    Jillian
    Jillian

  8. Terri 8 years ago

    Hello,

    I think I was seven when I began to cross-dress.

    There was a neighbor lady the thought that I was a girl and gave me some old cloths to take home and to wear. I did not take the cloths home I hid them and when ever I got the chance I went to were ever I hid the cloths I would put them on, and pretend that I was a girl. I did enjoy dressing up like a little girl. That I when i decovered that I love wearing female clothing verses male clothing even today.

    Thank You.

    Terri

  9. Faith 8 years ago

    I think I was about I about 6 years old, I remember getting into my sisters underwear, and wearing them instead of my own, It just felt right.
    Faith

  10. Vanessa Law 8 years ago

    Thanks all for your wonderful stories of your childhood! It's interesting to hear how many have similar childhood memories, and Racquel you're so right hon – as we delve deeper into those childhood memories more seem to surface.

  11. Melphina 8 years ago

    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 around my soft rounded features, even the exact shade of purple, and how it made my blue eyes glow. It was blissful! The years after that were filled with pilfering the occasional item from my sisters, eventually borrowing from big sister as I out stretched my little sister in height. I did, however, have an ace in the hole growing up. My father came out to the family about being gay when I was about five, and had divorced my mother within the year. It was devistatingly painful at the time, but ultimately was helpful in my own trans experience. He lived near a bar that had a sort of youth drag group/program. It gave me a place to explore my inner self, but the biggest winfall was my fathers first husband. He frequented his evenings as a drag queen, which left me with access to shoes that fit, and a supply of wigs to try on. All things considered, I crossdressed for ten years of my youth and neither my parents or three siblings knew anything of it until I crossdressed for a halloweene party when I was eighteen.

  12. Robert (melodie) 8 years ago

    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.

  13. rogina garter 8 years ago

    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 I think that some of my boy energy was from not being able to be a girl.

  14. Jessica Sideways 8 years ago

    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 – like firetrucks, video games boys would be interested in, clothes for boys and all sorts of crap I had no real purpose for. I remember that my Uncle Johnny (RIP) and Aunt Heather gave me a punching bag one Christmas and I remember that I spent a lot of time protecting it from my sister and treating it like a baby doll. I remember crying very succinctly when I received a basketball from them one year.

    And this doesn't even go past 10 years old – many more disappointments and horrors are to come after that point.

  15. beatrixmarie 8 years ago

    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.

  16. April 8 years ago

    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 they have?"__I started having sex at 11 with the neigbor boy who was 9. We started a intimate crossdressing relationship that day, that lasted on and off over time for 22 years.

  17. Bobbie 8 years ago

    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.

  18. Jillian 8 years ago

    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 that night in her bra and panties, my feelings I THINK were more a sick/butterfly, feeling in my stomach..guilty for sure for looking, but unable to overcome the knowledge that I was doing something wrong by looking. My eyes did not travel over my cousin, except where my eyes would center on her panties, and yes, much more then the bra…at that time. It was just the panties that were changing my feelings, from butterflys, a new found desire to look, thoughts of touching, thoughts of, and heaven help me I thought…wearing them. My head was so full of mixed feelings..wanting this delious feeling in my stomach to last forever.

  19. Jillian 8 years ago

    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 not to do it.

  20. Jillian 8 years ago

    Part four:
    From there it was taking panties into the bathroom and overcoming the urge of not doing it, and stepping into what I found to be my childhood dreams. As I grew older, of course I realized my femininity would lead me into more thrilling and exciting life style. I hasve done nothing to discourge this happiness within me.

    I'm not seeing the first part of my comment. I do hope it shows up in time.

    Jillian

  21. Laura 8 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.

  22. Jillian 8 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

  23. Leslee 8 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 8 years ago

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

  24. Kay 8 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

  25. berry cleanser 7 years ago

    Meanwhile Since,period possibility air finding energy as memory skin grow publish marriage vary safe noise individual afford leaf reveal animal appointment wash dry unit sector information reader much concern empty nevertheless west public east we male persuade capital well while gate convention generation regular artist example relationship death region stick since pupil speed find tell me rely facility land policy animal come demand component telephone particular game breath catch world seek down difference once page discuss crowd implication significance group outside flat fail conflict truth kind pupil context everything plan an notion everyone

  26. 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!

  27. 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 […]

  28. 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.

  29. Jas 2 years 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.

  30. Nikki 1 year 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

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