Halloween costume

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.
From that point on, I no longer worried about being outside, fully dressed as a woman. The only thing I worried about, now, was driving in those high heels! They placed my feet at a completely different angle to the accelerator and brake pedals and the first few minutes were a bit shaky! I soon adjusted, though and managed the drive to the Day Care without incident. Arriving there, I parked my car in the lot, grabbed my purse and walked to the Center. Walking toward the main doors, I stopped and lit a cigarette. Pulling the smoke down deep into my lungs relaxed me a bit. As I walked towards the doors, my mind was going two hundred miles an hour, and the familiar action of smoking was a much needed tension reliever!
I stood outside the doors, finishing my cigarette and, as I stood there a couple of the residents arrived at the center. They smiled at me and I nodded back at them but I saw NO light of recognition in their eyes! A couple of the workers came down to meet the arriving residents and I got the same response from them! They didn't recognize me either! All of a sudden, I began to relax. This WAS going to work for me! The workers and residents went inside and I finished my smoke and went inside, smiling.
Now, I hadn't worked on my walk very much, but those boots, slightly tight and with the three inch heels, forced me to take smaller steps and as a result, my walk was somewhat feminine. I didn't try to emphasize the sway of my hips nor did I try to restrain it. I just went with what seemed to work and didn't think about it anymore. I hung up my coat and slung my purse back onto my shoulder and walked into the day room where all the residents and workers would be.
As I entered, I could see faces looking at me questioningly as if saying, "Who are you? You don't belong here, do you?" I went into the back room where the employee's break area is and was greeted by the same kind of looks by my co-workers! Finally, after a couple of tense minutes, one of the women workers stepped close to me and looked at my face intently for a couple of seconds and then, she lost it! She began to laugh so hard I thought she was going to fall down!
The others looked from me to her, and back to me, wondering, I knew, what she was laughing at! When she finally recovered enough to choke out a few words, she said, "OH MY GOD! Don't any of you recognize who this is???"
Well, then they all began to look more closely at me and it wasn't more than a couple more minutes before they all finally realized who I really was and that started the damndest session of laughter and admiring remarks that it has EVER been my pleasure to be part of! EVERYONE was talking all at once but the gist of it was that they couldn't BELIEVE how good I looked! Now they were all in costumes as well, but none of them appeared to have gone to the time or trouble that I had. After a few minutes of that, it was time for me to clock in and begin work. I stashed my purse where the other women (OTHER WOMEN!) Stored theirs, and walked out into the day room.
It took about 20 minutes for word to spread through the day room and I felt a lot of curious eyes on me as I went about my business of getting coffee for people and socializing with them. What with those activities, and meeting people down by the main doors to escort them to the day room, I almost forgot the way I was dressed and felt very normal and comfortable! It wasn't until my first smoke break until my clothing difference made itself known again.
When I went outside to light up, my Boss was already out there and she hadn't seen me yet! I dug my smokes out of my purse and proceeded to light one and, as I stood there smoking, she was looking at me very intently as if trying to remember where she had seen me before! Finally I couldn't stand it any longer and I started to laugh! Now, I have never been able to imitate a female voice so my laugh came out in my normal male baritone/tenor and, when it did, she clapped both hands to her face and said, "Oh MY GOD! Mike! Is that really YOU?" And she was off into a laughing fit! I joined in with her and before too long, she was asking me a hundred questions, it seemed. How did I do this, how long did it take, where did I get the nerve for it and a lot more came out of her mouth.
I tried to answer as many of her questions as I could without giving her the idea that I was actually enjoying the way I was dressed and that I had done it before, in private, hundreds of times! We stood there and talked for about 15 minutes and, as a joke, I tried to hold and smoke my cigarette the way I have seen women do it. I guess I must have done it well because I could see her eyes following my movements and she even said, "Look at you! Standing there smoking like that!" I shrugged it off, saying,
"Hey, I'm only imitating what YOU are doing!" and laughing a bit to give her the impression that I was only putting her on. Little did she know that I WAS "going to school" on her! I WAS imitating her movements, trying to add to my repertoire of feminine movements! She seemed to buy my explanation, though and, when we finished our smokes, we went back inside together, our heels tapping on the hard tile floors. I was inwardly THRILLED to hear those sounds and to feel the skirt brushing against my legs but I tried not to let it show.
We entered the break room area and she dug into her purse for her compact and lipstick to freshen up, so, with a look at her, I did the same! She darned near got lipstick all over her face when she started laughing at me standing there with my compact open, freshening my lipstick and powdering my nose and chin!
Oh what a feeling it was for me, though. To be standing there with a real woman, putting on makeup in full view of her, with her knowing that I was really a guy was a kick I can't even begin to describe!
Well, the rest of the day went pretty much like that.
Eventually, all of the employees and residents of the Day Care finally recognized me and I was subjected to comments like "How GOOD you Look!" and, "Look how well she, I mean he, walks in those heels!" And, "You look lovely!" It was a day full of "ego candy" for me and I was getting more and more confident with each passing moment. Strangely enough, I wasn't feeling uncomfortable or "out of place" in the clothing I was wearing! It was almost as if I had forgotten that I was wearing a skirt and heels and makeup!
At lunch break, I went outside and smoked a couple of cigarettes with some of the other workers and all of them were marveling and commenting on how good I looked and how well I was carrying off what had to be a difficult costume to wear. "Costume!" I thought to myself. "If they ONLY knew!" After lunch, we all went back in and the "gals" and I freshened our makeup, which started a whole new round of laughing AND compliments on how well I did it!
The party itself began about 15 minutes after everyone was done with lunch and we took the wheelchair bound people down to the large hall first. I had no problems on the high heels, pushing the wheelchairs and, within about 15 minutes more, everyone was ready for the party to begin. We had spent the whole morning helping the clients get into their costumes and they were looking great! Everyone was smiling and having fun and then the band fired up and the party began.
We spent the better part of two hours at the party with the clients having a marvelous time and everyone who could, was up dancing. Now, I don't normally dance unless it's a slow dance and I like to be the one who leads, if you get my drift! From out of nowhere, one of the workers from another Day care center that was there sharing the party with us, came up behind me and tapped me on the shoulder! I turned around to see who it was and what they wanted and found myself staring at a guy who was, obviously, asking me to dance!
I was speechless! Hadn't anyone clued this guy in on who I really was? I looked around at my co-workers and they were all studiously ignoring what was going on! Now I was on the horns of a REAL problem! If I went ahead and danced with this guy, then he would be embarrassed and probably hate me for fooling him! If I turned him down, then he would still be embarrassed because he would get kidded about not even being able to get a guy to dance with him, much less a woman! It seemed that, no matter which way I went with this, he was going to come out a loser and I was going to have a problem with him in the future as I was certain he would try to get back at me!
I thought about it for a few seconds, standing there with him looking at me, expectantly. Suddenly, I had a flash of inspiration and I leaned in and whispered in his ear. "Listen, Arnie. It's me, Mike! Don't let on that I have told you anything. I think the rest of the workers are trying to put one over on both of us so how's about we turn it around on them? Play along with me and we'll give them a dance to remember! Otherwise, we are BOTH going to be embarrassed and probably end up hating one another!"
His eyes got REALLY big and he stepped back slightly to take a better look at me. Then, a look of recognition came into his eyes and he stepped back towards me and whispered, "Okay. Damn, Mike! I swear, I thought you were a woman! I'm sorry!" I whispered back, saying,
No sweat, Arn. I appreciate the compliment! Now, if we are gonna do this, we gotta do it right, so just follow me and don't worry! I started towards the front of the room where the band was set up and got the attention of the bandleader. He came over to the edge of the bandstand and leaned down to hear what I was saying to him. I asked him to, at the end of the song they were presently playing, start a slow number and explained what Arn and I would be doing and why. His eyes lit up as he realized that I was a male and he understood what we were going to do! Then Arn and I walked to the center of the dance area and waited the few seconds it took to end the song the band was playing.
They started the next song and I looked at Arnie and he got my unspoken message. He and I took the standard pose for a guy and a girl for dancing but reversed! I took the lead role, and Arn followed as best he could! I peeked around and saw that EVERYONE's eyes were on us and so I played it up just a little more! I whispered to Arn, "Don't lose it here, I'm gonna dip you!" and I chuckled a little bit.
I'll give Arn a lot of credit, he took that dip like a man, or rather, like a woman! It went beautifully and everyone applauded us when the song ended! I walked over to the bandstand and asked for the microphone and, when the bandleader handed it to me, I said, "I know that all of you," and here I pointed at my coworkers, "put Arn up to asking me to dance! I'd like to thank you for that. He's a great dancer, and I had fun!" With that, I handed the microphone back and did a curtsey to the entire hall!
Again, Arn followed my lead and he bowed to the hall full of people and then we joined hands and walked off the dance floor with our heads high! I caught a couple of admiring looks from the other employees and one or two shamefaced lookaways from one or two others. Arn and I walked over to those shamefaced ones and just stood there, hand in hand, looking at them. Finally, I said to them, "I think you owe both Arn and me an apology, don't you?
Well, they both kind of stood there, not looking at either of us and Arn surprised me again by speaking up, saying, "No, Mike, they don't owe us any apologies! If anything I owe them a thank you!" I looked at Arn, a bit puzzled but didn't say anything. He continued, "That was the most fun I have had dancing in a long time and, knowing that we were putting one over on these two made it just THAT much better!" And then Arn started to laugh! He looked squarely at the two would-be jokesters and finished by saying, "I hope you learned something here, today! If you didn't, see me after work, outside, and I'll continue the lesson!" And he held up a fist to emphasize what he had said!
I grabbed his fist and forced him to open it and said, with quite a bit of heat in my voice, "Look, Arn, there's no need for that!" Pointing at his now open fist. "They've learned their lesson, I think. Now, lets all shake hands and stay friends, okay? No hard feelings, you two," I finished and held out my hand. They looked at one another, then at me and at Arn and, finally, they did shake hands with us! I said, then, "Okay, then. That's the end of it then!" and turned to walk away but Arn had one more surprise for me!
He put out his hand, stopping me from leaving and then he grabbed my hand again. He looked at me for a second or two and then finally said, "You just saved me from a REAL embarrassment and I owe you one! I would NEVER have heard the end of it if you hadn't stopped me from what I was trying to do and clued me in on who you really are!" And then, he HUGGED me! Not a boy, girl hug, mind you, but a man to man kind of hug! When he let me go, I was a bit shaken and a little bit unsure of how to react but I finally recovered and we parted company as better friends than we had started the day as.
Well, the rest of the party was sort of anti-climactic but fun, nonetheless. I got a lot more compliments on how good I looked and for how I had handled the Arn situation though and I had a lot of fun at the party.
At around 2:30, it was time for me to leave and, I clicked my way back up the hallway to the break room where I took a few minutes to freshen up my makeup. Then I grabbed my purse, went down and got my coat and headed out the door, lighting a cigarette as I went. Holding it delicately between my fingertips and taking a long drag on it, I tilted my head back and blew a long stream of smoke at the beautiful, sunny day and started to laugh a little bit! "OH!" I remember thinking, "I wish EVERY CD/TV could have a day like I am having!"
I opened the door of my car and tossed my purse on the seat and slid in, remembering to sit down first, smoothing my skirt under me and then swung my legs in.
I sat there for a minute, finishing my cigarette and savoring the events of the day so far. Curiously, there hadn't been a single time during the whole day that I had felt even the slightest bit of sexual excitement, which usually accompanies the times I dress! Instead, I felt a sense of rightness, of contentment and I was as relaxed as I have ever been!
I looked into the rearview mirror and checked my makeup and then I started the car and drove home. I stopped on the way to pick up a couple of packs of cigarettes and got no real weird looks from anyone until I opened my mouth to ask for them. The woman at the service desk, where the cigarettes are kept, even asked, "Can I help you, Ma'am?" I LOVED IT! When I DID speak up to ask for my brand of smokes, her jaw dropped and she got the silliest look on her face and I started laughing! I paid for the smokes and left the store, still chuckling and went on home.
When I arrived there, I parked my car and visited the neighbors, figuring, "in for a penny, in for a pound!"
To my absolute amazement, they loved my outfit and, at first, couldn't believe that it was me! Then, when they finally accepted the fact that it WAS me, they kept commenting on how good I looked and acted! I had three hours to kill before my therapy appointment and I used all of it visiting the neighbors and talking with them. I'm certain that none of them realized that, the way I looked right then, was the way I'd prefer to look EVERY day!
When it came time for me to head downtown for my appointment, I didn't even hesitate! I climbed back into the car and checked my makeup and drove downtown.
I couldn't find a parking place anywhere near the building my appointment was in so I had to park about 4 blocks away. Again, I didn't even hesitate, I just parked, got out of the car and locked it, hoisted my purse onto my shoulder and began to walk the four blocks!
It was an incredible feeling, being out in Broad Daylight, fully dressed as a woman and not worrying about being "read"! I felt free and excited but, at the same time, calm and confident. As I walked towards the medical building, my heels clicking on the sidewalk, I felt totally in control and I don't recall getting even one strange look from passers by! Maybe I did get looks and maybe I didn't, I don't honestly recall. What I DO remember is that I didn't CARE if I got looks!
When I arrived at the medical building, I still had a few minutes until my appointment so I stood outside and smoked a cigarette, the same way as I had been doing all day, in the most feminine manner I could manage. When I finished, I went inside and rang for the elevator and waited while it took it's sweet time getting to my floor. When it arrived, I got in, pushed the button for the proper floor and stood back and waited while it did it's thing. Arriving at the proper floor, I exited the elevator and walked over to the reception desk and presented my card to the receptionist, and waited for her response.
She looked at the card, looked up at me, looked back at the card and said, "Thank you Mike. The therapist will be right with you. Why don't you take a seat and wait out here?" I took back my card, stuck it in my wallet which I then returned to my purse and found a comfortable chair to wait in. I made sure, once again, to sweep my skirt out from under me and sat down, as gracefully as I could. I found that I couldn't cross my legs in the feminine manner. I'm sure I don't have to explain why, but let's just say that I tried, and it hurt! Nuff said?
I only had to wait for about 5 minutes until my therapist came out and called my name. I stood up and moved towards her and I could see a bit of confusion in her eyes until I spoke up saying, "Hi, it's me!" Then she got a funny kind of half smile on her face and escorted me to her office.
I won't bore you with the details of what we discussed but I DID tell her all about my day and all the feelings I had been experiencing and I noticed that she took about three times as many notes than she usually did!
When my session ended, I stood up and got ready to leave. My therapist asked me one final question, though. She asked me, "How do you feel right now?"
"I feel great!" I told her. "I feel natural and complete and in control!" She looked at for a minute more and then said,
"Okay, session is over. See you next week at the same time?"
"You bet!" I replied. "Although I can't guarantee that I'll be dressed this way!" She chuckled a bit at that and then told me,
"Well, you can if you want to, or need to. It makes no difference to me and it isn't illegal!"
I left the building feeling like I was walking on air! I lit a smoke and enjoyed it while I walked back to my car and I played it up just a little bit, putting a little extra swing in my hips and enjoying the sound of my heels on the sidewalk. It IS tough to remember all of the things that make up a normal walk for a woman, when you are really a guy! There's the hips thing, then there's the arms and where they are held and used, while walking, and there's the head up, shoulders back thing as well! I didn't try to force anything but I must have been fairly convincing because I again noticed no one looking at me as anything but what I appeared to be!
When I got back to my car, I unlocked it, got in, and headed home. I stopped at a Mickey D's and grabbed some fast food for supper and, when I got home, my housemate/landlady was home with her little girl. She, my housemate, knows about my crossdressing and it doesn't bother her and her little girl thinks it's funny so I wasn't worried about them seeing me this way. I sat with them and talked while I ate my Mickey D burgers and fries, telling them about my day.
When I finished eating, I headed up to my room and fired up the computer so I could tell my internet friends about my wonderful day as well.
At around 1 o'clock in the morning, I signed off the internet and went into the bathroom to wash up and get ready for bed. I slept, that night in my long, lacy, black, silky nightgown and awoke in the morning before the alarm went off. Then I got dressed in my normal drab guy clothes and went to work.
All that day, I kept getting remarks and comments about how good I had looked and how well I had done. That was my Halloween for 2000 and it was DEFINITELY one I will always remember!
There is an aftermath to this as well.
Thursday, when I went in to work, I found that the clients of the Day care had circulated a petition to have me come back as Cathy for regular visits! My immediate boss was all for it saying that she thought I had a better figure than SHE had and if the clients wanted it and if I would do it, she didn't see anything wrong with it! The higher-ups nixed it though. They said, "It wouldn't be appropriate!" Oh well. I guess they are probably right about that but it sure was exciting to think that I had been THAT close to having permission to "dress" for work, whenever I wanted to, and who knows? Maybe in the not so distant future, they might just change their minds!
I'll be sure to let you all know when and if that ever happens.