A Delightful Arrangement

by Carolyn

Part One

   

I remember sitting alone in my house 8 months after my wife passed. It was a strange quiet to which I had sadly grown accustomed. I missed her desperately and had not ventured into any social life, preferring the solace of home. For amusement, I reverted to an old habit – spending many hours of my solitude dressed as a woman.

Yes, I had cross dressed throughout my marriage. Not often but enough that my wife realized I enjoyed it. There were costume parties where we would switch genders just for fun. One year I was an airline stewardess and she a pilot. We had some dear friends, Mark and Mary, who regularly held Halloween parties and it had become an ongoing topic of conversation discussing what female disguise I would wear.

Mark and Mary were quite well to do, not that you'd know it. They were a wonderful, down to earth couple. Their parties were legendary. They always hired a bartender and a maid so that they could enjoy their guests, not be bothered with cleaning and serving.

Now that I was on my own, I indulged in dressing frequently. I never went out in public, of course, but would spend days as a female, relishing the silky softness of woman's clothing. I had learned to do wonders with my hair, which I had grown out, of course. I spent hours perfecting makeup. Learning to do my own nails was very difficult for me. I was ok lacquering my left hand but doing the right took lots of practice.

Any way, there I sat, wearing a long sleeved sweater and a matching skirt, wondering where my life was going. I worked from home and actually did quite well. It seemed as though dressing was the only excitement in my life. I know it could have been worse.

The phone rang and it was my friend Mary. She and Mark had been so kind to me in my loss and regularly checked up on me.

"Alex, how have you been," Mary said when I answered.

"Hi Mary, I've been ok. Things are fine."

It felt odd to be fully made up, dressed and coiffed while I spoke with her on the phone.

"I just called to remind you we're having our costume party for Mark's office. You remember they're celebrating 20 years in business and it's going to be a super bash. You must agree to come!"

"Oh Mary, I don't know. I hate going to parties alone and really have no interest in escorting anyone. It just isn't the same any more."

"I understand, dear," Mary replied. "I didn't expect you to come but I know how much fun you used to have at our parties and just hoped you'd reconsider. The party will be so much fun although I just learned that our service will not be able to provide a maid for us this year. Such a bother! I guess I'll have to putter about keeping up with the clutter."

"Can't you find another service? I find it hard to believe there are no maids available."

"Oh Alex, I've tried. I've been on the phone all morning. Apparently at such short notice, no one is available."

My mind, of course, had been racing as she spoke. What a fun idea to be the maid for their party! It would help my friends and I knew I'd have such a great time being out after all these months, especially at a costume party dressed as a maid!

"Mary, I have an idea. You know how much I enjoyed your parties and how I often wore a female disguise at Halloween."

"I remember Alex. We all think you enjoyed that a bit more that you should have."

"You're such a good friend, Mary. I'll admit to you that I do enjoy dressing up sometimes and those parties were always great fun for me. How would you like me to come to your party after all? I will be happy to dress as your maid and provide the service a maid would provide."

"Alex! I can't let you do that! I desperately want you to come but won't take advantage of you. Let me find a date for you. I know lots of women that would love to come to the party and would be thrilled to have an escort."

"Mary, listen to me. I would have a ball being your maid and promise to do a good job for you. It is a costume party, after all, and this will be a fun costume for me. After all the kindness you and Mark have shown me, this is the least I can do. It's a win-win!"

"Well, if you're sure you want to do this, I'll be glad to accept. You've solved a big problem for me!"

"Great, Mary. I know you won't be disappointed. I know your maid used to arrive early to help set up so you could get into your costume. What time shall I get there?"

"Well, the party starts at 8:00. Can you be here by 6:30?"

"You bet! I am looking forward to it. It will be fun for all of us!"

With that we rang off and I sat back with a smile. A night as a maid! I had lots to do to prepare. The party was in three days.

I went to my closed and tried to find an appropriate costume. I had a nice black skirt and a delicate white blouse, long sleeved with a princess collar. I decided to try them on to see if I looked suitably maid-like.

I had amassed a nice collection of underwear and a few pair of shoes. I decided on a one piece to hold my figure in. Stuffing the cups, I put on a full white slip. I put on a pair of sheer black pantyhose and then the blouse and skirt. Shoes were going to be a problem. Most of what I had were 3 or 4 inch heels. I enjoyed wearing them but wasn't sure they would be practical for a night of serving guests. I put on a pair of black heels to check out the look.

All together, the uniform was fine. I would need to buy an apron and probably should check Payless for a lower pair of heels. Other than that I was ready to go!

I changed into male clothing, stripped my nails of polish and scrubbed off my makeup. I had to really work on my hair to make it look manly! I had begun styling it regularly to the point where it had developed more waves than a guy would wear.

Finally I was ready and left to shop. I found a frilly but practical white apron at a local department store. Naturally no one expected I was buying it for myself. I went to the Payless Shoe store I had visited in the past. I liked the fact that I could try on shoes in relative seclusion because of the way the aisles were arranged. I knew my size and found a cute pair of 2 inch club heels with a lace up, tie style. I slipped one on and was surprised at how comfortable and feminine they were.

Checking out a Payless was always easy. I learned long ago that the clerks thought nothing of a guy buying a pair of women's shoes.

As I drove home I couldn't help but smile at what the day had brought me! I knew there wouldn't be any people at Mark and Mary's party that I knew but that was fine. After all, I would be there to serve, not socialize.

The next days passed quickly. I decided to spend them fully dressed to get even more inured to my female side. I really liked the shoes I had purchased. They were so comfortable and I enjoyed the lace up style.

The day of the party I waited until early afternoon to shower and shave. Of course I shaved my legs and armpits. I decided to have a nice soak and filled my tub with hot water and scented oils. It seemed a good way to get into the role I was about to play.

I put on a robe and went into my living room to do my nails. I selected an iridescent pink, understated but making a statement nevertheless.

Afterwards I spent some time on my hair. It was shoulder length and I was able to style it with a flip at the ends ala the old Mary Tyler Moore style. I dressed slowly. Getting dressed is almost as much fun as being dressed!

When I had put my slip on I went into the bathroom to apply my makeup. I decided to be reserved, given my position, for the evening: soft foundation, some subtle color on my cheeks and just a hint of eye shadow.

I did use eyeliner and mascara to enhance my blue eyes. I waited to apply my lipstick until I was fully dressed.

It was time for my blouse and skirt. I just love the feel of a skirt and was becoming pretty excited about the evening ahead. I pulled on my pantyhose and laced up my shoes. Finally, I put on my apron.

For accessories I was again conservative. I wore a plain gold bracelet and two gold rings on one hand. For earrings I chose a small gold hoop set.

I went to the mirror and applied a soft pink lipstick with just a hint of gloss. I felt pretty. Even though I appeared to be a relatively plain woman, it was a wonderful feeling to be fully dressed and made up.

I was getting pretty nervous. It had been a long time since I had been out in public dressed as a woman and this was my first time solo. It was warm enough to eschew a coat so I started to the door. Suddenly I realized I hadn't thought about a purse. I found one which I stocked with essentials including my lipstick and gloss.

Finally I was at the door, ready to head to Mary's house. I took a deep breath and walked to my car. My house was at the end of our street and my yard had bushes and trees enough to shield me from nosey neighbors.

As I climbed into the car I purposely tucked my skirt under as I sat facing the road. I lifted both legs into the car together in a ladylike manner.

As I began to drive, the sensation to driving in heels was a rush! I'd forgotten how different it felt and recalled how surprised I was the first time when I realized it wasn't at all difficult. The magnitude of the adventure hit me as I motored down the side streets. How lucky to have a legitimate chance to be publicly dressed. I felt sensational!

When I arrived at Mark and Mary's I took my purse and went to the door. Mary opened it and let out a little whoop.

"Alex! You look fantastic. My goodness, how much time did you spend to capture your image. Even your hair! Is that your own? How do you feel in this costume?"

Her questions and comments seemed unending. I smiled and told her that I wanted to look just right for my role.

"After all, Mary, I am your maid tonight. And please, don't call me Alex! For tonight, I will be Carolyn."

"Ok, 'Carolyn'. Why that name?"

"Well, many years ago I knew a Carolyn. She is no longer with us but I used to admire her. She was a kind person, always perfectly groomed and a delight to be with. I guess when I'm portraying your maid I will channel my memory of her. Is that ok?"

"Of course, dear, I'd forgotten how much you used to enjoy dressing up for our parties. I'm so glad you've come and that we have a role for you to play that obviously will be fun for you. And let me add how much I appreciate your help. I hope you're prepared to be a busy lady tonight!"

We went into the kitchen and she explained the preparatory tasks she wanted me to handle while she dressed for her party. There was nothing difficult. I immediately went to work preparing dishes that would carry hors devours. Soon I was alone in the kitchen, moving about as my heels clicked on the hardwood floor. It was a wonderful experience. I was looking forward to an evening of servitude.

Mark came into the kitchen and whistled playfully at me.

"So, I'm to call you Carolyn tonight, right? You certainly don't look at all like a man, Alex. It seems you've gone a bit overboard with your costume."

"Well Mark, you know me. I enjoy playing a woman's role and I figured it would be fun to serve you and Mary tonight without letting on that I'm a man. Since I don't know any of your guests, maybe I'll fool them."

"There's no doubt. If you continue to carry yourself like this and don't slip up by raising your voice, I will be surprised if anyone will see through your disguise. They'll all expect a woman filling your role and likely won't give you a second thought."

"Great, Mark. Just don't forget to call me Carolyn! I'll be busy cleaning and straightening and will just be in the background while you all have fun at the party. Believe me; I'll be having my own fun!"

"It's a deal, Carolyn. I just came down to tell you how much we both appreciate your help tonight. I'm surprised how convincing you look and act but it is fine with me. I think this is the happiest I've seen you in months. I'm really glad you're here with us!"

With that he left to put on his costume. Guests would be arriving soon. I was to greet them at the door, take their coats and put them in the guest bedroom. My night of fantasy was about to begin. I was shaking with excitement!

  

  

  

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