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?

More Articles by The Author

The following two tabs change content below.
I’m passionate about creating a safe space for everyone in the transgender community to find laughter and friendship on their journey. I completed my physical transition in 2011 and through it I lost everything, and gained everything. I am blessed that I was forced to gaze inward and embark on the journey to discover and live my authentic self. My deepest wish is that all who wander here may find peace, happiness and freedom.
Tags:
0 0 vote
Article Rating
Subscribe
Notify of
41 Comments
Inline Feedbacks
View all comments
Stace
10 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… Read more »

Racquel Lynn
10 years ago
Reply to  Stace

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… Read more »

Racquel Lynn
10 years ago
Reply to  Racquel Lynn

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… Read more »

Racquel Lynn
10 years ago
Reply to  Racquel Lynn

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… Read more »

Veronica
10 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… Read more »

Arthur
10 years ago
Reply to  Veronica

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….

Jack
10 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!

jeri
10 years ago
Reply to  Jack

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

Melphina
10 years ago
Reply to  Jack

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.… Read more »

Racquel Lynn
10 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… Read more »

Racquel Lynn
10 years ago
Reply to  Racquel Lynn

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,… Read more »

Robert (melodie)
10 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,… Read more »

Jillian
10 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… Read more »

Jillian
10 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… Read more »

Terri
10 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.… Read more »

Faith
10 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

41
0
Would love your thoughts, please comment.x
()
x
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials

or    

Forgot your details?

Create Account

If you don't see the captcha above please disable ad and tracking blockers and reload the page.