Halloween and my Childhood

A Remembrance of a National Holiday

by Annie

(ORIGINALLY PUBLISHED HALLOWEEN '99)

For the thirty second straight year, I won't be in any sort of costume
tonight. It wasn't always this way, you know. In fact, once upon a long ago,
Halloween used to be my favorite time of year. My earliest memories of
crossdressing and arousal are all connected with it.

My mom always had a way of picking out EXACTLY the costume I DID NOT want to
wear for Halloween. Two years in a row, she tried to get me to put on the
dreaded cowboy outfit. God, did I protest! I HATED it, and all things
masculine (which I never really expressed out loud). ANYWAY, she got a
brainstorm that year, I believe it was my 9th, that she'd pretty me up in
one of her going out nightclubbing dresses. I still remember it vividly.
This was black and glass beaded, and weighed a half a ton. A very exotic
dress for my initial foray into womanliness.
So, here was the genesis of my crossdressing in earnest, as well as the
first connection for me between sexual excitment and having a dominant woman
feminize me. To this day this persists in me, in SPITE of my being aware of
its origination.

I can still recall as she went ALL OUT, even down to her underwear and
strange support garments (mama had a big butt) that I had my first ever
tingle of eroticism, and an overall feeling that at long last I was in the
correct clothing. I felt serene and excited simultaneously.
Apparently, Mom was also that night playing out one of her favorite
fantasies.

I was second born in our family, after my brother. My mom told me when I was
6 or 7 that she had wanted a boy first, and then hoped the next child (me)
would be a girl. I think she may have been disappointed at my birth that I
wasn't born female. In all honesty, so was I. I HAD to have picked up on her
vibes.
Even my dad called me "Babs" until I was four years old, when my sister came
along. So, I guess they both wished for it.
I was too young to remember, but perhaps I was even treated as a daughter by
them for those formative years, that is, until Carol's birth. All I can say
with any certainty is that I always from my earliest memories thought of
myself as a girl, which would cause me immense grief later on. When their
third child came along, the game for them suddenly stopped, and I was
expected to play by different rules. BUT, once a girl, always a girl, even
now.

So there I was, getting all dolled up for the first time, right down to a
pair of low heels (kinda big) and stockings that attached to the girdle
(remember THOSE?). The finishing touches, and the cementing for me of this
part natural/part erotic experience came with the placement on my head of
one of her wigs, some perfume spritzed here and there and then her skillful
application of full makeup. Having lipstick applied for me is STILL one of
my biggest turn-ons, probably because it was the last thing she did that
night before I got the chance to view myself in a full length mirror.
I looked (to my young eyes) TERRIFIC!

To heck with the candy I collected that year. For me, just being able to
express my true tendencies and not catch hell for it was wonderful.

This began a lengthy pattern of clandestine crossdressing throughout my
childhood. I'd steal an old abandoned bathing suit of my mother's, or an
undergarment of some sort, and stash them away somewhere.
I used to spend hours in the bathroom borrowing mom's makeup and practicing
with it.
After I reached the age of 12 or so, my family would go to church on Sunday,
and then out to visit relatives, and I'd stay home and be "Barbara" (Babs?)
for a few blissful hours.

Here it is, over thirty years later....another Halloween, another Sunday
morning.
I typed this story out while sitting here in a cranberry colored VERY short
nightie. My breasts are real, thanks to 20 months of ongoing HRT, and the
feminine feelings, genuine. I know clearly who I am, how I got here, and
most importantly, where I'm going.

The last part is incredibly satisfying.

I wish for you much happiness and all the love you truly deserve.

Annie