Halloween 2006, Part 1

The place where I now work has way too many people, so I could never entertain the thought of going to work as Arianwen on Halloween; however back in 2006, I was working in a small office (only about 30 people) and the company for whom I worked at that time had announced that there would be a contest and lunch provided for those who chose to "dress up" that year.

I hemmed and hawed about participating almost up to the last minute.  I had a few wardrobe choices, but I didn't think I could work up the nerve to go to work dressed up as a woman.  Several nights prior, I talked briefly with my wife about doing this and received her blessing, if not approval.  Later that day, I started to talk myself out of going through with the plan, because I didn't have exactly the right something or other.  On the drive home from work that night before Halloween, I had just about talked myself out of dressing up the next day.

Just after my son had gone to sleep that evening, W (my wife) had inquired if I was going to or not.  Just as the word "no" was about to slip from my mouth, I instead said something to the fact that I would if I could find a wig at the local drug store.  While I was searching for a decent (meaning less than $10) redhead wig, I was mentally preparing for what else I might need for the next day.

I had decided on a long red dress with three-quarter sleeves and a high neckline.  A black bra and nearly matching panties underneath, with black pantyhose (I didn't have suspenders/garter belts at this time, unfortunately) and a long black nylon slip underneath the dress.  I didn't even bat an eye as I picked out some red nail polish and lipstick at the store, but had to settle for a black witches wig.

When I got these few things home, I then started to resent the fact that one of our cats had managed to puncture the blue gel (the stuff that helps keep your stuff cool in the lunchbox) filled balloons I had been using as breastforms up until several weeks before this time.  I quickly discovered that I still had a few of the pinkish colored balloons in a drawer and decided to fill them with water, as I didn't have enough time to find enough replacement blue gel.  After filling the balloons and leaving them on a towel near the bathroom sink, I determined that I was prepared to face the next day as I had hoped to do for many years -- dressed as the woman I felt inside.

I awoke the next morning, well before my alarm would normally would have gone off, and shaved off the goatee I had been sporting for about a year beforehand.  Then, I attacked the hairs on my legs which I had allowed to grow back in from the last defoliation event several weeks prior.  After cleaning up the sink and tub where these two shaving events took place, I took a quick shower using my wife's soap, shampoo and conditioner.  Knowing that W would be needing the bathroom shortly afterwards, I wrapped the towel around myself (girlie style, of course), grabbed the two water-filled balloons, and quickly moved off into the bedroom where everything I needed was either laid out on the bed before I took the shower, or stashed in the closet.

After inspecting the room to ensure that neither of the cats could sneak up and ruin things today, I closed the bedroom door, dropped the towel on the floor, and pulled up the black nylon panties into place.  Next came the black nylon pantyhose, which successfully did their job of bringing about that little thrill that comes with running nylon over recently smooth skin.  After quickly putting on the black bra -- of course, by hooking everything up in front of me and then carefully twisting everything around 180 degrees into place, just like I had seen W do hundreds of times -- with great anticipation I placed the rather cold artificial breasts into the bra cups and had them produce a double shiver within me.  The first shiver, of course, from the temperature of the water inside the balloons, but the second one was the unanticipated excitement from filling out the bra cups completely (and thinking about how nice it would have been to be real at that moment).  Rounding out the "buzz" factor was slowly pulling the black nylon full-length slip over everything else and enjoying the few seconds where the bottom of the slip caressed my nylon-encased legs.  I then placed the red dress above me and slowly work it down, making sure that everything settled correctly into place.

At this point in time, I was very grateful that it was the end of October and not the middle of summer, as I was feeling quite warm at this point and needed a few minutes to cool down.  I picked the towel up off the floor, pulled the only pair of women's shoes I had out of the closet and sat down on the bed for a few minutes, dabbing the small beads of sweat from my forehead with the towel until I felt cooled down enough to continue.  From the closet, again, I pulled out the lipstick and nail polish from the plastic bag holding the goods from my adventure the night before, carefully attached the plain fake nails I found in W's makeup collection, and proceeded to apply the nail color to each nail (since this time, I have grown rather fond of the cool feeling of the nail varnish being applied to the fingernail).  While I was waiting for the nail polish to fully dry, I say the error in my ways, as I still had liquid foundation, mascara, and eye shadow to apply, which I had never done before with false nails.  I did manage to do rather well with the foundation, making sure to get up to the hairline and down to the neckline, and rubbed the slight excess off on the back of my hands.  The mascara was a bit more of a challenge, and I took a lot of time to apply it, especially since I had not used it in a very long time prior to this morning.  By the time it came to the eye shadow, I was running out of time and patience and didn't really try to do a perfect job -- my post-rationalization was that I needed to look like this was the first time wearing women's clothes and makeup.  After cooling off again for a few minutes, I sprayed some of W's perfume (Chanel #5) on me, put on my two-inch heeled shoes, placed the new wig on my head, stuffed a few necessities into an old black computer bag with a long shoulder strap (as near a purse as I had at the time), and slowly walked out of the bedroom to face my family.

To be continued, in Part 2.