A Delightful Arrangement

by Carolyn

Part Six

  

Friday morning I awoke with energy. It was a good thing since today I was going to help prepare for Anna's party. I showered, shaved and prepared to dress. I wore my new breasts, of course along with my gaff.

I knew I was going to be working hard so I chose a loose fitting blouse and a knee length skirt that wasn't too tight.

Prior to dressing, I remembered that my nails were only allowed a touch of color. The bright red on them now would not do! I cleaned them and applied a pale rose that I hoped wouldn't offend. I just couldn't bring myself to not having any color at all.

That task completed, I put on a slip and added the blouse. I chose a pair of nude pantyhose and then stepped into my skirt. Finally, I selected a pair of red flats that would allow me to work quickly and be easy on my feet. After slipping them on and standing, I realized how long it had been since I had NOT worn heels. I missed them immediately but realized that this was a job, not a fashion show.

Adding some conservative makeup with just a touch of pale rose lipstick, I was ready to go to work. Grabbing my purse, I walked slowly to the car. I realized that without heels to remind me, I would have to be alert to the fact that I was not just a guy in woman's clothing but a man who was portraying a woman's role. As far as Anna knew, I was the woman whom she met at Mark and Mary's party: the woman who provided such subservient yet professional maid services. It was quite a joy to be in this role.

When I arrived, another girl was there. She had already begun the preparation. After introducing ourselves, we dug in and worked quite well as a team. Within a few hours, our jobs were done and we were ready to leave.

Anna came to inspect and was totally satisfied with what she saw.

"You ladies did a fine job. Carolyn, I am very pleased to have discovered you. It appears you take pride in your work and are not one of the many ostentatious women my agency has tried to saddle me with. I don't understand why so many of the girls that are assigned here feel the necessity to wear revealing clothing and whorish makeup. Thank you for paying attention to my rules."

"It is my pleasure ma'am. I am so happy for the opportunity to work for you, both today and tomorrow. I hope you'll be happy with my service and allow me another chance in the future. As for your rules, I find them quite logical. I am not here to impress anyone with my clothing or style. My job is to serve you and your guests in the manner you expect."

She really seemed to like that response. I was a bit surprised at myself. I normally would never reply in such a passive manner. In fact, it seemed to me that I was being a bit submissive in my answer.

Of course, that was what she wanted to hear but instead of phrasing my comment to meet her expectations, I actually meant what I said. I had certainly accepted my role as a servant and frankly, I enjoyed my status. It dawned on me that I enjoyed it because my status was entirely female in her eyes. How nice it was to be accepted in such a role.

We left shortly thereafter and I buzzed home, my mind fully focused on my dinner date with Gary. While I did not expect it to be anything more that a "let's get to know each other" evening, deep in my heart I had to admit that fantasies were spinning!

When I arrived home it was barely 2:00. I had a full five hours to prepare. My thoughts leapt to what I would wear. Should I try to dress provocatively? My goodness, I had never thought that way before. What a silly girl! I didn't have clothes that were designed for enticing a man. My entire wardrobe, aside from my working woman attire, was selected for me! I enjoyed dressing and acting as a woman but until last week, never with an eye for how my attire would affect anyone's opinion of me. All I cared about, up to now, was that I was accepted as a woman.

This line of thought gave me serious pause. What in the world was I going to do to balance these new emotions against my realistic understanding of whom and what I really was?

I decided a nice hot bath would help me relax and focus on the evening ahead. As I soaked, it dawned on me that tonight was not a make or break date. (Yippee! I was going on a date!) No, this was merely an evening to spend with a very sad and needy man who I assumed was looking to me to become a friend with no strings to the past. As I pondered this I realized that indeed I would be thrilled to play such a role in a person's life. Actually, I could use a friend with no ties to my past as well. A fresh start would likely be beneficial to both of us.

When I had climbed out of the bath and toweled dry, I applied scented lotion and started on my hair. I still was waffling between a flip outward and the inward flip that I had worn the last few days. I decided on the inward style as I enjoyed the way it framed my face. I wasn't unhappy with my hair color although I realized that it wasn't vibrant at all: just a plain brunette. Perhaps I should look into some highlights?

I also did not want to wear pale nails tonight. While I didn't want to try to look like I was on the make, as it were, I certainly felt that a brighter color would be appropriate. Before choosing the hue for the evening, I deemed it wise to decide what to wear. After all, no sense in sporting nails that clashed with my outfit.

I had been thinking about a plain black dress I had acquired a few months prior. It was short sleeved and, before cleaning the hair off my arms, I had never really enjoyed wearing it. Now that my arms were femininely bereft of hair, it would be a great selection.

I had saved most of my late wife's accessories. Her clothes didn't fit well and I had given them to our thrift shop. However, all of her jewelry, purses and scarves were still neatly tucked into drawers. She had a beautiful silk shawl what would be a colorful accent to my dress.

It was full sized and had a mix of pastels in its design. The overall theme was pink with soft yellow and blue accents.

I laid it out on the bed and pulled a few nail polish bottles out. I finally decided on a fairly bright pink that matched the shawl nicely. This, of course, would set the tone for the rest of my makeup.

I gave thought to wearing stockings but decided that pantyhose would be more appropriate. Frankly, stockings gave me chills, not only as I put them on but usually unexpectedly as I wore them for a period of time.

They are quite feminine, if not flat out sexy feeling.

I did wear a corselet over my gaff and after tucking in my breasts, I put on a full black slip. It didn't matter if I needed a slip or not: I loved them and wore one nearly every day. I slipped on my pantyhose, having selected a sheer black pair that would work well with my dress.

I had obtained a pair of strappy three inch heels that I simply adored. As I put them on, I reveled in the slinkiness they added to my look.

Finally I stepped into my dress. It zipped up the back and it clung to my body quite nicely. I went to the mirror and loved what I saw. I added a simple necklace with a small black stone that hung just to my cleavage. I thought dangling earrings wouldn't be too garish and they were perfect! A pair of gold bracelets on my left arm along with a gold ring on my right hand seemed to balance the outfit well.

I put the shawl over my shoulders and it fell gracefully over my breasts. Frankly, I had to admit I looked pretty good. All that was left was my makeup.

I took off the shawl and applied foundation and cover up. I decided to add just a hint of pink toner and selected a pale pink eye shadow. After lining my eyes and applying mascara, I brushed on the eye shadow and was thrilled with the image. I used a tube of pink lipstick and added some pink gloss on top. Smacking my lips, I shivered with delight at the taste and feel of them. If men only knew what they were missing! Lipstick is the most sensual part of the entire makeup routine.

I stepped to the mirror again and donned my shawl. I was quite satisfied with my appearance. I hoped that Gary would be!

It was nearly 7:00 and I sensed he likely would be on time. I spritzed on some perfume and selected a purse for the night. It was a small bag but had room for necessities: lipstick and gloss, perfume, mints and my keys.

As I waited for Gary, I forced myself to calm down. The process of dressing, this time for a date, had excited me. I couldn't help but hope that Gary was attracted to me as I had really worked hard to be as pretty as I could be. I had to remember that we were just friends and that our dinner was likely nothing more that adding to the foundation of that friendship. However, a girl can dream, right?

When the doorbell rang, I jumped. I had been miles away in my mind, pondering all the possibilities. Suddenly, here he was.

When I answered the door, Gary took a long look at me and whistled softly. Oh my, what a shiver charged up my back.

"Carolyn, my goodness, you look stunning."

"Why thank you, dear. I'm so glad you think so."

He smiled and offered me his arm as we walked to his car. I clutched it rather tightly. I had never held a man's arm before. It felt incredibly good.

He opened the car door for me and I demurely sat and swung my legs in together. As I waited for him to walk around the car my mind was flying. It felt wonderful to be out with a man. I felt entirely female and allowed myself to luxuriate in the role.

Gary entered the car and we began our drive to the restaurant.

"I hope you like basic food, Carolyn. I've picked a spot I used to enjoy but I haven't been there in a few years. It used to be comfortably predictable but I have no idea what they'll be offering tonight."

"No problem, Gary. I am just so happy to be having dinner together. I certainly enjoyed meeting and talking with you. I hope we can build on what we've started."

"Thank you, Carolyn. I liked our talk as well and certainly have grown fond of you already. You're not like other women.........." With that he blushed.

"Don't worry, dear. I know what you meant. Of course I'm not but that won't matter tonight. You make me feel 100% girl, through and through. That's one of the things I like about you!"

We both laughed off his minor faux pas. Inwardly, I was entirely pleased that he saw me in comparison to "other women". I was growing very interested in this man.

When we arrived at the restaurant, Gary helped me from the car and I held his arm as we walked in. No heads turned in the room. I suppose most women would be disappointed but not this girl. I loved being accepted as the woman on Gary's arm. Frankly, the only head I cared to turn was his!

We sat and ordered some wine. The menu was perfect: steaks, seafood and pastas. I ordered a baked halibut dish and Gary chose a t-bone steak.

"I have to tell you, Carolyn, that I was pretty nervous today. I couldn't believe that I had the nerve to call you and to make this date.

It has been a long time since I've had the courage to do this. I still don't know why I did it but as of right now, I'm very happy to be here with you."

"Oh, Gary," I responded. "I'm happy too. You and I have spent too many months, in your case years, in solitude. It has done me a world of good to prepare to go out with you tonight. I was nervous today as well but you certainly have calmed me down. You are a lovely evening companion."

We continued to chat while we enjoyed our dinner. The food was lovely but the companionship was so much more than I had dared hope. Gary was a great talker, once he got going. We stayed away from our sad pasts and focused on the present. Before long it was time to leave.

"Carolyn, I hope I haven't bored you tonight. I really enjoy being with you and hope we can do this again."

"Bored me!" I replied. "Oh my goodness, Gary, this evening has been wonderful for me. I hate to see it end."

"Me too," Gary continued. "I haven't felt this relaxed and comfortable with anyone for such a long time. You are great therapy for me not to mention a wonderful dinner date."

As we walked to the car, Gary took my hand instead of offering his arm. I wallowed in the wonderfulness of the gesture. Driving home, I decided to take a bold step.

"I've enjoyed this time with you, Gary. Would you consider me too forward to invite you in for a nightcap? It still is early, you know."

Gary paused and I could have kicked myself. "You blew it girl" I thought to myself.

"I was going to ask you if you wanted to stop for a drink, Carolyn. I'd love to come in for one at your place if you don't mind. I agree with you, this night has been too nice to let it end this early."

I reached over and squeezed his hand. "I'm so glad, Gary. I truly love being with you."

When we got to my house, he gallantly opened my door and asked for the house keys. Holding my hand, he led me to my door, unlocked it and stepped back for me to enter.

As I turned on the light, I turned to him and we collided! I didn't realize how closely he was standing behind me. Our faces were so close I could smell his aftershave. I looked up at him and he down to me. Without thinking, our lips met, ever so briefly. It was my first kiss from a man and I nearly swooned. I grabbed onto his arms just to catch my balance.

"Gary, I'm so sorry. You just caught me off guard and took my breath away."

He backed off, apologetically.

"I am the one to apologize," he said. "I shouldn't have done that, Carolyn. You just looked so kissable and I'm afraid it just happened."

"Gary, don't misunderstand. I loved it. Please do it again."

He took my arms and pulled me to him. This time the kiss wasn't spontaneous but it wasn't any less thrilling. His lips pressed to mine for minutes, so it seemed. Finally we broke apart.

"Gary, I've thought about this very minute since the day I met you. You know about me. Are you sure you're comfortable with such intimacy with a man in woman's clothing?"

"Carolyn, I have been forcing myself to remember you are a man all night long. You look entirely female. You act like a woman and you have a definite female personality. I'm afraid I view you as a woman wearing woman's clothing. As for kissing you, it's been on my mind for days as well."

"Oh Gary, I can't believe this. Yes, I feel like a woman as well and am thrilled to have you treat me as such. You are a wonderful kisser, by the way."

What I didn't tell him was that I wanted more of that mouth on mine! Fantasizing about this moment had no prepared me for the reality. I felt the bones in my legs had turned to spaghetti.

"Why don't you sit down and I'll get us some wine."

I had to do something or I would simply collapse into his arms then and there. He sat on the couch and I went to the kitchen for the wine. I stopped to catch my breath. Looking in the mirror I saw my lips were smudged.

"I'm just going to freshen up, darling," I said at the kitchen door. "Make yourself comfortable."

In the bathroom as I applied fresh lipstick and gloss, I looked in the mirror. Eye to eye with this new person I had become, I gave my hair a shake. "Ok girl, tonight you are a woman and you may as well go with it. He likes you, you like him. Don't be shy. Just have fun." These thoughts ran through my mind as I primped to look as attractive as I could. Straightening my dress, I went back into the living room.

Gary had poured our wine and was standing near the couch, waiting for me.

"You have a lovely home, Carolyn. I'm glad you invited me in."

"Thank you, darling. I'm so happy you are here. I am learning to like you more and more as our evening is progressing."

He took my hand and led me to the couch. We sat and toasted our relationship. As I held my glass to his, I noticed how nicely my braceleted bare arm with the red nails at my fingertips contrasted with his manly hand. I felt a rush of femininity.

We sipped our wine and he reached for me. Setting our glasses down Gary wordlessly took me into his arms and started a gentle but probing kiss. I responded carefully. I didn't want to be too aggressive but I certainly wanted Gary to know I was enjoying his tongue tangling with mine. It was a gorgeous moment. My hands gently held his head as I ruffled his hair and massaged his neck. The kiss was deep and thrilling.

When we finally parted, he looked directly into my eyes.

"Carolyn, I am really turned on by you. I can't remember being this enchanted with a woman nor being so aroused by one. Please forgive me if I'm being too forward."

"Gary, dear, I feel you from my scalp to my toes. I have never been kissed by a man before and there are no words to describe how you've made me feel. Don't ever ask me to forgive you for being too forward! You're the man, darling. I await your advances."

He kissed me again and this time pulled me even closer. I could feel his arousal and it excited me beyond words. In all my fantasizing, I hadn't gotten beyond a kiss.

I put my hand on him and his groan was seductive. I, of course, had never felt another man's penis before. I was at once curious and aggressive. I had to have more than the feel of it in his pants. My hand went to his zipper and I pulled away from his mouth. As I gazed questioningly into his eyes, he smiled and, with a nod, pulled me back to him.

Unzipping his pants, I reached in and felt his strong erection. It nearly popped out of his pants for me! Stroking it was driving him wild. I certainly did not have a calming effect on me!

Without thinking, I ducked down and started to nibble. Soon my nibbles turned to licks and before I knew it, he was in my mouth. Gary's hands were on my back and dropping. He moved slowly in rhythm with me. Soon my head was bobbing as I explored the joy of his maleness. He began to moan and was moving with me. I sensed his imminent eruption and prepared myself for the explosion I knew was near.

When it began I nearly swooned. My mouth was engulfed with his cum and I knew that a proper girl swallows everything. It wasn't as easy as I had thought - Gary had so much for me! My cheeks were bursting but I gamely kept it all in until it finally went down my throat. It was the culmination of my entrance into womanhood.

As he slowly subsided, I continued to caress him with my lips and tongue. I didn't want him to slacken but, of course, I knew he would. Men!

Finally I sat up. I'm sure I was a mess but Gary didn't seem to think so. His kiss was no longer slow and sensuous. His mouth was hard on mine, our lips spread and our tongues darting. I held him closely so he wouldn't see how I was shaking. I had done it! I had pleased my man.

When we finally sat back gasping for air, I looked up at him through my tousled hair.

"Oh Gary," I sighed. "I must be a wreck!"

"Carolyn, you are beautiful. That was so wonderful. I thought you said you had never been kissed by a man. Clearly you are more experienced that you let on," he replied with a smile.

"Honestly darling, I've never done that before. Did I do ok?"

Asking this was clearly trolling for a compliment. The result of my loving had certainly been fully evidenced by his incredible climax.

"You are superb! I haven't had sex in over three years and can't remember it ever being this good. Carolyn, you are one hell of a woman."

I stood up and headed to the bathroom. He could say anything but I knew I had major repairs to do. Indeed, my face was full of lipstick and my hair was everywhere. Quickly I made myself at least presentable and returned to him.

He knew I had a full day ahead so we agreed that we should call it a night.

"You know I have to see you again, Carolyn. I'll have your face in my mind forever!"

"You're so sweet, Gary. Of course we will be together again, soon. I can't wait to be in your arms again."

He kissed me at the door, a lingering kiss full of romance and intimacy. Weak at the knees, I closed the door behind him and collapsed on the couch. What a night it had been. I examined my feelings. While I had clearly become enveloped into my female role, I frankly had not anticipated that I would get so carried away by it.

I was surprised at myself. I realized how aggressive I had been, how passionately female and how sensuous. I knew I had fully satisfied Gary and was surprised how satisfying that was for me. I recalled how I had strained at my gaff while sucking him. Even now I was painfully aroused yet enjoyed the feel of my clothing holding me in.

I laughed as I realized I still had my heels on! Kicking them off, I massaged my toes. I knew I should get to bed but for some reason, I couldn't leave the couch - our couch - quite yet. The smell of our sex was pungent. The memory of Gary deep in my mouth was delicious. I could still taste him!

I stretched out and let sleep slowly wash over me. What a night.

  

  

  

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