A Delightful Arrangement

by Carolyn

Part Five

  

The next two days passed uneventfully. I spent each day as Carolyn and became quite used to my new breasts and the constriction of my gaff. I went to a drugstore and bought a container of hair remover which I used to clean my arms. I thought about using it on my legs but enjoyed shaving them too much. I know most women view this task as a necessary evil but for me it is a sensuous, deeply feminine procedure.

Having hairless arms opened new options for me. I had been limited to long sleeves but since my new maid uniform sleeves were short I had to clean my arms. Now I could wear any type of top or dress without concern about arm hair.

Late Wednesday Mary called me. We chatted for awhile and I regaled her with the details of my new life.

"Carolyn, it certainly sounds like you've made quite a turnaround. You sound so happy and have really gone to great lengths to develop your new look and persona."

"You are right, Mary. This has been such a wonderful discovery time for me. Each day seems to have a new surprise. I can't tell you how much I enjoy acting as a woman."

"I have a delicate topic, dear," Mary said. "I'd love to have lunch with you and I'd like you to meet someone. You have something in common and I think you'll like him."

"Him!" I exclaimed. "Mary, I would love to have lunch with you but I don't want to meet anyone, especially a man. I'm not that kind of girl!" I blurted the last out with a silly laugh. I was taken aback by her idea.

"Hear me out, Honey. Gary is a lonely, sad friend of mine who made a terrible mistake and has been paying for it dearly for the last three years. His wife caught him with another man and promptly divorced him."

"You want to introduce me to a gay man? Mary, what are you thinking?"

"Actually, Gary hasn't been with anyone since his divorce. He confided in me that this was a one time experiment. He is so ashamed he hasn't seen anyone socially for this whole time. I know you've been keeping to yourself as well and simply thought he might be a good friend for you to cultivate. He's really quite a nice person and I'm sure you'll like him."

"What have you told him about me?"

"Actually, nothing. I haven't even discussed lunch plans with him. I think he would be happy to join us and as far as he'll know, you are just one of my girlfriends."

"Well, Mary, let me give this some thought. Let me call you back tonight. Have you told Mark about this idea of yours?"

"Yes, it actually was his idea. He and Gary have been friends for many years. Last night we were talking about you and how you've blossomed. He suggested that I introduce you to Gary hoping that each of you would benefit from having a new friend. Certainly it will be fun for you to have a friend who knows you only as Carolyn. I doubt Gary would have any intentions beyond a casual friendship. I know he needs to shake him self loose of his current malaise before he falls into a depression."

On the spot I decided to go for it: to meet this man and perhaps befriend him. I trusted Mark and Mary and knew they wouldn't put me in harm's way. We agreed to meet for lunch Thursday at 11:30.

When I hung up I sat there surprised at what I had just agreed to do. On one hand, I had no interest in meeting this man other than to perhaps help him through this tough time. Goodness knows I had just been through one like that myself. On the other hand, the idea of lunching with someone who would accept me as my new self had a delicious scent to it. I decided to have fun with the project.

I slept fitfully that night. My mind went back to the movie I had watched as I had fantasized about playing the female lead. Deep in my mind the memory of the tingles I felt when she had been kissed were closer to the surface than I cared to admit.

Thursday morning I took my time getting dressed for lunch. I brushed out my hair and set it with a face framing curl at the shoulder. I preened putting on my makeup and spent extra time on my eyes hoping to look as good as possible. I was getting into the idea of meeting this man and decided that I wanted him to see me as an attractive woman.

I selected a white cashmere turtleneck sweater that accentuated my breasts provocatively. With it I wore a dark brown skirt, nude sheer pantyhose and brown three inch pumps. My nails were red so I selected a bright red lipstick with a pale pink gloss. The combination made my lips shine!

Soon it was time to leave so I grabbed my purse and headed to the restaurant. Mary was waiting for me and was shocked at my appearance.

"My goodness Carolyn, you look stunning! Did you buy breasts? Look at you!!!"

"Why Mary, how sweet of you to notice," I responded camping it up a bit.

We both laughed as we walked to our table.

"Gary will be here soon. I told him you are one of my favorite girlfriends that just moved back to town. He protested, as did you, that he wasn't looking for a woman nor did he want me to be a matchmaker."

Mary went on to explain that Gary had recently been very depressed. Instead of rebounding from his disastrous divorce, he had been withdrawing to the extent that Mark was seriously worried for him.

"I really hope you two hit it off. I don't expect he'll want to date you so have no fear of that. I just hope you can be friends. It may be just the ticket to bring him back to his old self."

Soon Gary arrived. He was pale and seemed nervous. However, he was quite well groomed and dressed nicely. I was surprised how tall he was. Even in my three inch heels he was nearly a head taller than I.

Our lunch was actually quite delightful. As we talked, Gary seemed to brighten marginally. When I explained I had lost my spouse nearly a year ago he took my hand as he expressed sincere sympathy. I glanced at Mary and noted she had a small grin as she watched us interact.

"Carolyn, you and Gary seem to hit it off quite well. Gary, I'm so glad you joined us. Carolyn has been dealing with her loss rather well and I hope she can be an example to you as you deal with your circumstances."

Gary's response was a pleasant surprise. "You know Mary; I haven't talked with anyone new for years. I nearly didn't come today but now

I'm glad I did. This lady is such a sweetheart and seems to be entirely non-judgmental towards me. Perhaps I should stop judging myself so harshly."

"Gary," I responded, "I'm so happy to hear you say that. Mark and Mary have been such dear friends to me during my time of sorrow. They've really brought me out of my shell. I hope I can grow to be that kind of friend to you."

"Thank you, Carolyn, but there is much about me you don't know. Perhaps I should tell you what I did to cause my wife to divorce me."

Suddenly Mary stood up. "Goodness, I have a hair appointment at 2:00. The time has flown! Do you two mind if I dash off. Of course, you can stay and get to know each other."

Gary and I agreed to stay behind. Mary left and we ordered glasses of wine.

"Gary, I think it would be good for you to tell me your story. In fact, I'll tell you mine in exchange. I enjoy your company and perhaps, when all our cards are on the table, we can move forward."

He agreed and laid out his tale. Apparently he had experimented once in college with another boy. It was not an unusual story. Two horny boys with no dates for weeks were alone in their dorm. The other boy was more experienced than Gary. They had a few beers and the boy convinced Gary to let him suck him. When he was done, Gary felt obligated to return the favor. It was the only time he had done anything like that until three years ago.

"I don't know what got into me, Carolyn. I was at a bar and this guy chatted me up. We had quite a bit in common: you know sports and all. I guess I had too much to drink and before I knew it, we were walking to my car. I had parked around the corner and it was secluded. He put his arm around me and I just let him. He turned me to him and kissed me. I was stunned but strangely didn't resist."

"Just then my wife pulled up. She knew where I had planned to be and had come to have a cocktail with me. She saw the kiss and embrace and that was it. I had divorce papers in my hand the next day. She wouldn't talk to me other than to tell me what a disgusting farce of a man I was.'

As Gary told me this story his eyes were teary. I knew it hurt to tell his story but it seemed to help as well.

I took his hand to comfort him. Suddenly I was aware of who I really was and felt guilty for fooling him into thinking he was dealing with a woman.

"Gary, you've told me about yourself and I appreciate your honesty. Believe me; I don't judge you at all. In fact, what I'm about to share with you may drive you away from me."

With that said, I explained everything to him. I began by confessing that I was really a man. He was shocked but sat back to hear the rest. I told him about my wife's death and how I had found solace in cross dressing. I explained how Mark and Mary had let me serve as a maid for their costume party and how much fun it was to carry out the masquerade so well that everyone accepted me as a woman.

"I'm truly sorry if I've offended you by allowing you to think I'm a woman, Gary. I've been having such a grand time doing this that I'm afraid I lost sight of how I might hurt someone."

"You know, Carolyn, I am surprisingly not upset with you at all. I must tell you, the news comes as a complete shock to me. I'm sure you realize how what an attractive woman you make. Your sense of style is wonderful: your makeup is perfect and you have lovely hair. However, it is your personality that makes you the woman you appear to be. It's obvious, now that I know the truth that you really have gotten into the role. I'm glad you told me but even now it is hard to interact with you without feeling like I'm talking with a woman."

"Oh Gary, that is the nicest thing to say! I'm so happy you can accept me as I am."

We talked for over an hour before Gary realized how late it had become. As we prepared to leave, he asked for my phone number.

"I'd like to call you, Carolyn. I've had no one to open up to for such a long time and I feel we really connected. Strange as it may seem, I'd like to see you again."

"I feel the same way, Gary. I'm very comfortable with you and truly enjoy your company. I hope you call me!"

As I drove away, my thoughts remained on this new man in my life. He and I truly had quite a bit in common. We certainly talked easily with each other. Suddenly I was afraid he may not call me!

I ran a few errands. I decided to pick up a sweater set to wear to Anna's for the pre-party preparation. I also bought a pair of red flats. I never had any woman's shoes other than heels and thought for my work the next day, flats would be appropriate.

When I got home there was a message from Gary! How exciting. I returned the call at once.

"Hi Gary. I'm so sorry I missed your call. I was shopping after our lunch."

"Hello Carolyn. I'm glad you called back. I just wanted to tell you how great it was to meet you and spend time with you today. I definitely would like to see you again. Will you have dinner with me?"

"Yes!" I replied, probably a little too quickly. "When would you like to meet?"

"I know you are working Saturday night so how about tomorrow? I hope

I'm not being too forward but I really want to see you soon. I feel liberated from my self centered sadness and have you to thank for it."

"Saturday will be wonderful. I am working that day preparing for the party but I should be home by 5:00."

"Super! I'll pick you up at 7:00, ok? I'll make reservations. Just give me your address and it's a date."

I gave him the address and we rang off. I was almost giddy with excitement. This surprised me and I sat down to digest what had happened. After months of solitude I suddenly had a new friend that accepted me as the woman I had become. Further, my friend was a charming man who had sorrows of his own. We certainly fed off each other in such positive ways.

I tried to rationalize that it was just a friendship that we were beginning to nurture. The more I thought it through, the more I realized I was curious about what the nature of our relationship might become. Did I want him to kiss me? I hadn't been kissed for over a year. Did I want to kiss him? I know he had not had any intimacy for three years.

What a delicious predicament. It shook me as I realized that yes; I did want his lips on mine. I had never been kissed by a man before. I had no idea how it would feel or even if I would enjoy it. However, I knew that thinking about it was exciting! I would have to tone down my emotions at dinner. My goodness, who would have guessed that this subservient maid would harbor such aggressive thoughts!

The more I delved into womanhood, the more curious the experience had become. Today had been a day of revelation. Perhaps it began with my fantasy watching a woman being kissed in a movie or maybe, somewhere deep in my heart, this curiosity had been brewing for months as I hid my sadness behind dresses and heels.

As I spent the remainder of the day cleaning and getting ready for bed, thoughts of Gary were never more than a blink away. I decided to find another old movie with a beautiful heroine I could become in my mind.

Sure enough, a kiss scene came and after watching it, I closed my eyes and pictured me and Gary in the pose. Then and there I knew I wanted him to hold me. Oh my, how to deal with this!

  

  

  

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