The Holiday BLSB Cartoon Series by Sissy Demi
Click Read More to view Part 1

Though not dated on the actual image, I created this one Halloween 2001 for Crystal's StorySite. I just recolored the Sailor Moon outfit used in Part 5 of the Original Cartoon Series and added a a little witch's hat.

Halloween has always been a crossdresser's paradise. It is often the one time of the year we allow ourselves to dress openly with little fear of people finding out our true nature. Though, sometimes, it is just this open airing of our desire that allows others find us out.

Growing up I went door-to-door in traditional Halloween costumes: sheet ghost, hobo, cowboy, construction worker, werewolf, and the like. There were three times, however, where tradition became untraditional.

The first I do not remember at all. Only a fading Polaroid in the family album lends credence to the story my mother tells me. In it, I am just nearing my third birthday and and surrounded by my sister and her friends. (She was seven then). One was a ladybug. Another, a boy, was a spaceman. A third is dressed like a nurse. My sister sported a girl-cat costume of headband ears with a bow, cute girly kitty face make-up, a black leotard with flouncy short skirt, and black tights.

The story goes I cried and threw tantrums because I wanted a costume exactly hers. This went on for days until my mom caved in and made me one, too.

So there I stood, in a cute girl cat costume, grinning to the camera as my sister looks down at me with a look of mixed aggravation and amusement. Her friends don't seem to care.

I wish I remembered all this. *sigh*

My second girl costume was when I was about seven. The parochial school I was attending was doing a Thanksgiving production. My mother, being the artistic person she was, was in charge of costumes and scenery. She had started early October preparing, and both my sister and myself were often used as dummies for her to work on the costumes. Yes, I wore the oft-recognized pilgrim outfits, male and female, as her dress dummy. As well as various Indian garb (we didn't yet call them Native American).

With Halloween upon us, and mom so tied up in costuming, she had no time to make me something, as she usually did. Buying one was out of the question for our relatively low income family. I wanted to go as a pilgrim, but there was no way mom was going to allow one of the costumes out and about on Halloween. They were too time consuming to make and funds were limited.

However the Indian costumes were cheap to do, and she had extra beads and feathers. She also had a single extra Indian girl costume ...

I was secretly excited when she told me I was going as a squaw (again, before the derogatory meaning of the word was open knowledge). However, I put up the expected fuss, and went a little far (for mom, happy for me). She then said I was going to have some make-up on as well as the faux leather, fringed and beaded dress and the feathered headband with yarn twin braids down to my shoulders. It wasn't much make-up; some rouge, lipstick, and mascara. No extra moccasins, either, so I wore a pair of my flip flops. ^^;;

The third time dressing in a girl costume growing up was in the seventh grade.

I was attending a private Christian school (mom swapped religions a few years earlier) and we were having a Fall Festival. (It's just a way for religious people to celebrate Halloween without calling it Halloween ... I never understood that). We could come in costume for the games, hay ride and haunted house. (Yeah, Halloween is bad, so let's call it different but still do everything the same ... duh).

Gwendolyn, a girl friend (not girlfriend), said she was going as a JV football player; pads, helmet, jersey, etc. With a wicked grin she asked if I'd come as her cheerleader. I may have agreed to fast because she looked at me oddly before laughing and smiling.

So, she lent me hers.

My sister, in the 10th grade, thought this was hilarious and girlied up my hair with a red headband, and put some light full face make-up on me. The red-and-white cheerleader outfit was not like you typically see, this being a Christian school. The skirt was knee length, the sweater was full sleeved and high necked, shorts were worn under the skirt. I had to wear my own sneakers, but I had a pair of socks with the little puff ball on the back. And pompoms, of course.

A few other guys came in drag, but I was the only one who was not done up in a parody style. I was teased a bit, and one senior guy pinched my butt. I think he thought I was a real girl from behind, because he had this blushing laugh when I turned around. Gwen thought this was the funniest thing.

Gwen was also the very first girl I kissed while dressed up.

We were in the haunted house and she was squealing and giggling at the cheap scares, holding my hand as we wended our way through. At one point, she dragged me into a darkened corner off the main path through the haunted house and suddenly kissed me. It wasn't a deep, soulful kiss. Just a quick, dart forward, pressing her lips hard on mine, and an even quicker release.

I was shocked and excited and scared and all floaty-feeling.

She wasn't the first girl I had ever kissed, or had kiss me, but I thought we were just friends ... and I was dressed in her cheerleader outfit!

I asked her why she kissed me. Her reply was simply, "Because you're cute."

She then pulled me back into the main path before the next kids came through. I followed in a daze, hardly paying attention to the cheap scares until we were back outside. Sarah acted as if nothing happened, and I was too scared to bring it up to her.

We finished the Festival out and I returned her outfit the next school day. She never brought it up again, and seemed a little more distant with me. She stopped sitting next to me in chapel, and in lunch she sat across from me instead of next to me like before the kiss. Every time I tried to mention it, Gwen would find an excuse to leave and became even more cold and distant.

Gwen moved just after Christmas; her dad was accepted as an associate pastor at church in another state. I was invited to her family's going-away party, along with other of her friends. It wasn't until near the end of it she grabbed my hand and asked me to go out back with her.

She started crying and said she was sorry she treated me like she did in school, that she really liked me and was scared because she never liked a boy in that way before, and because she knew she was moving soon even though it wasn't certain and didn't even tell her friends, and she said she'd write me and maybe I could come visit and ... It all came in a torrent of emotion. Words ran into words, tears streaked her face.

I just held her hands in mine and listened, a small cold ball of ... something, in my chest and throat. I was sad, and I realized I liked her in that special way, too. I told her this when she finally slowed down.

She practically leaped into my arms and we held each other for several long minutes. We may have stayed entwined for longer but her mother came out to see where she was. I could tell her mom was shocked, but she said nothing. Just a narrowing of the eyes and thin lipped smile. She cleared her throat and asked Gwen to come back in because there were other ... friends ... she should say good-bye to.

Gwen kissed me again, then. In front of her mother. Then she let me go and walked back inside, wiping her eyes and face as she did. Her mom looked at me strangely for a few seconds and told me my mom had called and was on her way to get me.

I never saw Gwen alone again in the remaining minutes I was at her house. We did chastely hug as I left; the same chaste hug everyone else got.

We wrote to each other for a few months after. But, as in many long distance relationships, things cooled between us over time and distance.

The last letter I got from Gwen said she was making new friends and liked her new school and church. She included a picture of herself in front of her new house, and wearing her old JV cheerleader uniform. On the back she wrote: "I still think you looked cute!"

I often wonder what may have happened had she not moved and we were able to get our feelings in the open sooner.

I suppose Gwen was my first real love.

It is also why I often use her as a love interest in some of my tales.

Sorry this has gone much longer than my usual anecdotes. The memories I just related are bitter sweet, but fond. I am glad I was able to share them with you.

-- SD