Halloween costume-1

I had been unemployed since the end of April and had been assigned, by Social Services, to work off my cash grant from Welfare, at a Senior Citizen’s Day Care Facility. I found, rather rapidly, that I actually enjoyed being there and helping the residents. We would play games with them and keep them interested in life in general by coming up with projects for them to do. Not big projects, mind you, but small things that would test their memories and skills. Things, like I said, to keep them interested in life.

I couldn’t help making friends with them even though I knew I wouldn’t be there for long, or at least I hoped I wouldn’t. I wanted to find real work again and I had no thoughts of staying there any longer than I absolutely had to, but, as the weeks went by, I found myself being drawn into their lives and I began to realize that maybe this was what I NEEDED to be doing! Helping people through their golden years and just being a familiar, friendly face to them.

I found out that there was going to be a big Halloween party with all the residents AND the workers were encouraged to dress up and I began to make my plans. There was a huge rummage sale at the very church in which the day care was located and I went through it like my life depended on it! I took home 6 bags full of clothing the looked like it might fit and several pairs of shoes and boots that looked brand new! When I got back home with the clothes, I spent about 2 or 3 hours trying them all on, from skirts and blouses to shorts and dresses. I was even fortunate enough to have located some items of lingerie like slips and bras and, believe it or not, everything, or almost everything, fit!

Then I tried the shoes and boots and, with the exception of one pair of knee high boots, they fit as well! I was elated since, with these clothes, I had effectively quintupled my “femme” wardrobe and I wasted no time getting everything into the washing machine so they would all be nice and clean, hanging in my closet, waiting for me to find the time, and the courage to wear them.

Among the things I found, was a beautiful, long sleeved, red blouse that felt so silky I thought, at first, that it might be silk! It turned out to be artificial but, none the less, I knew that I was going to wear that blouse for Halloween! I also came up with a below the knee, length, Jeans skirt and a belt with a country look to it that went perfectly with the skirt. I had raided a box of stuff, at the rummage sale, that was marked “FREE”, and had managed to come up with 8 or 9 purses that looked like they had hardly been used at all and, of course, I took them home with me as well.
With all those things, I knew that I was going to do it, this Halloween! I was going to go to work, fully dressed as a woman and I was going to do it with some style! I already had an entire box full of makeup and jewelry and a couple of decent wigs from past Halloweens and my occasional dress up sessions at home so I didn’t have to buy any of that stuff. I had also been growing my fingernails for the last month or so and they were beginning to reach a length where they could be shaped and painted like a real woman’s could.

I had over a month till the party and I determined that I would keep growing my nails until then.
After getting all the clothing washed and dried, I carefully hung everything up or folded everything and stored all of it in my closet or dresser drawers. I had “come out” to all my friends and family over three months before this and I had no fears about someone finding women’s clothing in either place. To their credit, every single one of my friends and family had been, not only understanding about my crossdressing quirk, but were actually supportive and they all told me the same thing. “We love you and if this is part of you, then we have to accept it. We don’t necessarily approve of it, but you are our friend/brother/son and we will always care.” This, to me, was a revelation and, to not have to hide anymore was the most wonderful feeling in the world!

Through the Internet, I had also made some VERY good friends in the TG community and I had even begun to write some stories, encouraged by them. The stories had been fairly well received and this was more “ego candy” for my femme side. This Halloween party would be a sort of test for me and my femme side, Cathy. If I could do this well, I thought, I would be another step closer to understanding and dealing with my crossdressing tendencies and why I seemed to need to do it.
I contacted a friend who is a Mary Kay cosmetics representative and made an appointment with her for a makeover, for Halloween morning. I met with her and showed her what I would be wearing and also, the wig I would be using since my own hair is fast running off the back of my head. What I have left is long enough but my forehead has grown in the past few years and there isn’t enough hair left to cover all the balding spots anymore. She looked everything over and seemed to approve of my choices and we began making plans to put everything together so I could be as realistic looking as possible.

See, I didn’t want to be a clownish, heavily painted trampy looking female. I wanted to look as normal as I possibly could. I was going to make this party and the day as complete an experience that I could possibly have. I had to know if I COULD pass as a real woman! I had been in therapy for the past few months for several things, one of them being my gender issues and I had arranged for my therapy appointment to be on the same afternoon as the party so that my therapist could see how serious I was about wanting to understand and deal with my crossdressing. I also knew that, by arranging things the way I had, I could prolong my experience and make a complete day of it.
As Halloween approached, I took every opportunity I could find to practice walking and moving around in the skirt and heels. I knew that, since I don’t wear heels and a skirt everyday, I would need every bit of time I could find to appear comfortable in them.

I also practiced with makeup, knowing that I would, at some point during the day, have to repair some of what I would be wearing. I painted and cleaned my nails several times each day so I would be able to do them properly without smudges or overprinting them and ending up with nail polish on my fingers.
The week before the party, I was as nervous as a long tailed cat in a room full of rocking chairs! I had planned everything as well as I knew how to and I hoped I hadn’t forgotten anything. This was going to be a critical day for me. Not only would I be spending all day as my femme self, but I would have to be particularly convincing while going to my therapy session. The last thing I needed was that someone would “read” me, while downtown. I mean, if I were going to be a caricature of a female, it wouldn’t matter if I were “read” or not. Since I was taking the, to me, daring step of trying to appear as REAL as I could, if I WERE “read”, it would be disastrous both for my plans and for my mental well being.

The morning of Halloween, my friend arrived at my door at 830 A.M. to begin my makeover. She brought what looked like an oversized tackle box full of makeup and applicators and, well, a lot of things I had never seen before and had NO clue about! She told me to sit down, close my eyes, and follow her instructions. Well, I am many things but a fool is NOT one of them! I sat there with my eyes closed and followed orders! I can’t even begin to remember all of what she did but an hour later, she told me to open my eyes and look in the mirror. When I did, I couldn’t believe what I saw.
There in that mirror, was a woman! Now, I am not handsome and I didn’t expect a beauty to be looking back at me, and I was right. However, the person that was looking back at me was NOT male! Once the wig was in place and secured I actually did look like a woman!

I stammered my thanks and she just smiled at me and said, “Have a great day…Cathy!” With that, she packed up her stuff and left me to finish dressing.
I struggled into the undergarments, a tight panty girdle, a long line bra, thigh high hose, a half slip, and a camisole. Then I stuffed the bra with a couple of heavy duty balloons filled with a mixture of water, gelatin, and birdseed and donned the blouse. I was right about that blouse. It felt heavenly as I struggled with the opposite side buttons! Soft and silky and lovely looking, with two attached long pieces of cloth for a tie at my neck. I pulled the skirt up to my waist and secured it along with the belt and bent to put on my boots.

Those boots, brown and REAL leather, were about 1/4 of a size too small but I had been wearing them for up to 4 hours every day in the hope that they would stretch out enough so I wouldn’t be crippled at the end of the day! They had been a gift from another worker at the day care who had bought them and found that the boots were too large for her. She had worn them twice and put them in a closet and forgotten them. When she learned of my plans for Halloween, she offered them to me saying, “If they fit you, use them for Halloween and keep them! I can’t wear them and it’s too late to try to return them to the store.” I stuttered my thanks and you can bet I still have those boots and will never give them away! They have 3 inch stacked WOODEN heels and are REAL leather! They must have cost her a fortune and I couldn’t believe my luck at having them given to me as a gift!

I put all the makeup I would need, according to my friend, in a black purse along with my wallet, my cigarettes, in a case, my lighter and my keys. I also threw in some tissues, some Q-tips and a brush for my wig. Then I grabbed a heavy black woman’s coat and put it on. I stopped at a mirror on the way out of the house to check one last time that everything was as perfect as I could make it and, slinging the purse over my shoulder, walked outside my house! My only concern, at that point, was that one of the neighbors would see me coming out of the house and getting into my car. They, the neighbors, didn’t know, yet about my crossdressing or my plans for this day. Fortunately, none of them were outside and I made it to my car without being seen.