Beginnings – Day 5 – Harry's Job Offer

by Carolyn

  

When I got out of my bath I checked the time. I had a few hours before Harry was due to pick me up. I decided to just relax and play through the last few days. It had been quite an experience. I had gone through a series of steps in adopting a female persona, each of which had a part, large or small, in placing me in my current situation.

After liberal lotion, I had simply thrown on a bra and my robe and was sitting quietly in my television room. The TV played softly in the background, just white noise to complement my thoughts.

I mused on going out with Harry. There was no doubt I had become enamored with Suzy and the wonderful things we did together. I also was surprised at the stirrings I felt regarding Felicia. Why I was even interested in seeing Harry caused me pause.

As I wondered about that I thought back to that first night, a scant 5 days ago. I remembered how awkward I felt when he kissed me and how that feeling fled as we kissed more. I also remember taking him into my mouth. At the time it felt idyllic. Being dressed, accepted and treated like a woman had my head in a swirl at the time. I must admit that as I recalled those feelings, I understood why I had to move forward with my date tonight.

I had no clue what the night would bring – after all, who knew what Harry had in mind. I resolved to give it my best and see what the evening brought.

With that, it was time to get ready. Of course I shaved closely – what a bother that was.

Then I laid out my outfit. I had my new black short sleeved dress. I added a black waist cincher, a lacy black bra, a pair of black control panties, garter belt and black sheer stockings. My 4 inch pumps were simple but stylish so I selected those to complete the presentation.

I began with the waist cincher, pulling it in another inch. The discomfort of an additional inch wasn't more than I had experienced the first day I tried one of these. I switched bras and loved the feel of my breasts encased in lace. Adding the garter belt, I gently pulled on my stockings. As always, I marveled at how wonderful stockings or hose felt on my waxed legs.

Slipping on my mules to protect my stockings, I donned the control panties. I took a look in the mirror and loved what I saw. If only Harry would know what I had on under my dress and slip!

I put my slip on and went into the bathroom to work on my hair and makeup. Once again I opted for my smoky eyes look. I had learned that one well. I chose a dark red lipstick that was a close fit to my nail color.

I went to my jewelry drawer and grabbed my new hanging earrings. Carefully removing the studs, I gently put on the new ones. They were a hoop style, gold hanging down about two inches from my ear. I just loved them!

Time was running short so I put on my dress. It was the shortest I had worn, falling just at my knee. When I put on my pumps I realized my hemline had risen to the top of my knee. I went to the mirror and was relieved to see that the look, while attractive, hadn't degenerated into sleazy.

I sat back on the bed and saw that sitting was going to require concentration. My dress exposed more leg than I had expected. Without being alert, I would show leg nearly to the second shade of my stockings!

I picked out a gold necklace, three thin gold bracelets for my left hand and a chunky style for my right. I added my onyx ring on my right hand and a very thin gold ring for my left pinky.

I looked into the mirror again, (yes, I do that a lot!) and was satisfied. As always, I wasn't a knock out but frankly I was beginning to believe I looked every bit a middle aged lady preparing for a dinner at a nice restaurant.

I checked my purse to make sure I had everything I'd need: lipstick, compact and perfume. Perfume! I had forgotten. I spritzed quickly and was ready.

When the bell rang, I nearly jumped out of my chair. It was time! I opened the door and there he was. Tall and handsome, he wore a dark blue suit with a crisp white shirt and tie. We smiled at each other and he took a long, lingering look from my eyes to my toes.

"Carolyn, I must tell you, I had forgotten how attractive you are. You have done something to your hair and your breasts are so realistic!"

I grinned and made a slow turn so he could see the full woman in front of him.

"Harry darling, I decided to spend the entire time since we met as Carolyn so I would learn if I would be able to accept the position you offered. I have to tell you, I love being a girl and haven't missed wearing pants a bit!"

"Does that mean you plan to accept my job offer?" Harry asked.

"No, not yet, I have to learn more about what you have in mind. However, I am looking forward to hearing what you plan and must admit, you're looking at a hungry lady!"

We laughed and he helped me with my coat. I just LOVE that. Walking to his car, I slipped my arm through his. I had decided that, if only for tonight, I was going to play

my role as a woman to the hilt. I was his date for the night and I wanted him to be proud to be with me.

Getting into his car was dicey. I carefully sat on the seat with my legs outside the car. My skirt rose precariously and I was glad I had my coat on. Lifting both legs in together with my knees touching I settled in without incident. I felt pretty vulnerable with my short dress.

Harry drove us to a hotel that had a five star dining room. We went in and he was greeted by everyone!

After checking my coat, Harry asked me if I minded if he had a cigarette after dinner.

"Some people are quite put off by smoking, Carolyn. If it bothers you I won't mind."

"Why Harry, please don't be concerned. In fact, I have an occasional cigarette as well. Maybe I'll join you."

He gave me his arm and we walked to the small concession story. Harry bought a pack of Marlboros and a pack of Virginia Slims for me.

"Harry, honey, you are just the sweetest man!"

"Carolyn, you'll learn that I know how to treat a lady. Come on, let me feed you!"

When we reached the dining room the maître de came to attention and escorted us to a secluded table. I was impressed. This man was well known, at least here.

On the rose was a vase with two roses. I looked down and gave him a coquettish look, smiling to show that I understood the symbolism.

"Oh Harry, you are so thoughtful. I love them!"

As he pulled out my chair for me (Oh do I love this treatment!) I turned and gave him a light kiss on the cheek.

"You are a dear. Thank you for the roses, Harry."

Realizing I left a lipstick mark on his cheek, I quickly rubbed it off.

"I guess there are still a lot of things I need to learn," I laughed.

 

We had a glass of wine before ordering our dinner.

"Carolyn, I think now would be a good time to talk about what I have in mind. Would that be ok?"

"Absolutely, I'm dying to hear about your plans."

"I haven't told you this but I own 9 clubs, 5 here and 4 others in different cities. I've been slowly building my portfolio over the years and am ready to add a new one. It will be here and will be an alternative club. I'm planning on opening a transgender accepting club and dining room. Our city had one a few years ago but it closed and there is room for a new one."

"I am hoping you'll agree to manage that club for me. If you chose to do so, it would be as Carolyn. I expect you to learn the business and be in charge of personnel. Once we're off the ground, I would like you to be the hostess of our restaurant which I envision being on the second floor of the building."

I fear I was quiet for too long as I took this in. What an interesting idea! I hadn't ever thought of something like that.

"Harry, do you really think there is a market for a place like this? I don't mean to question your judgment but I must admit this comes out of left field for me."

"I really do. I've been to clubs like this in other areas of the country and used to frequent the club that was here. You'd be surprised how many people frequent an atmosphere like this. There are some gawkers but overall there are many men who enjoy dressing as women but have no place to go. I want there to be a safe place for them where they can have fun and be ladies for a night."

"But are there enough men like that? I certainly haven't seen any of them."

"Believe me, there are. You haven't seen them because there aren't many places for them to go. You could, and do, pull it off in a public environment but many can't. After all, obviously you've invested a lot of time and money to capture your look. Could have done this if you had a family? How would a wife react to a husband with waxed arms and a perm, not to mention your breast forms? They're quite nice, by the way."

I grinned and wiggled my shoulders so the girls danced for him. We both laughed.

"Ok, I'll accept your premise. Do you think you could teach me to run such a business?"

"Well, that brings me to some questions about your background. I hesitate to be too businesslike during out dinner because I don't want to spoil the evening. May I ask you a few things?"

"Of course! I'm entranced by this idea and, if I'm going to do this, I want you to know whatever you wish to learn."

"Thank you, my dear. Please tell me about your business background. Have you managed people before?"

"Why yes, I have. Presently I am a commodity trader. I work from home and have been doing this for about 8 years. I'm quite successful and earn six figures. I enjoy the freedom of being my own boss and setting my own schedule. However, this is not an easy business and I typically spend about 9 hours a day working, between research and analysis."

"Before this, I managed a large group of people who provided customer service and sales work for the part of my corporation that I ran. I had full P&L responsibility, was a go to person in the sales process to our larger clients and was in charge of budgets and forecasting. I reported to a Vice President. I had 7 managers who reported to me. They did the hiring but we worked well together to ensure that we maintained a qualified staff."

"When my company was sold, my job was eliminated so I decided to bag the corporate world and work from home."

"Wow, Carolyn, I would never have guessed. It sounds as though you have the experience to handle this job. If you can learn commodities, certainly learning to run a club should be no problem for you."

"May I ask another question, this one a bit personal?"

"Of course, Harry. I won't conceal anything from you."

"Have you ever dressed as a woman before? You certainly carry this off beautifully and I'm having trouble believing you've never done it before."

"No, last Saturday was my first time, except in getting prepared to do it then. I admit I am quite surprised at how well the role seems to fit me, mentally. I know I don't make a beautiful woman but I feel quite comfortable and believable in this role."

"Wow, I admit I'm astounded. You are right, you're not gorgeous but you are attractive, pure woman, and, as you know, certainly able to get a man's attention!"

I must have blushed because he took my hand and smiled.

"I have thought about Saturday night often, Carolyn. I remember your kisses and how it felt to dance with you. By the end of the night, you were a woman in my mind and I enjoyed our time immensely."

"However, that brings me to another issue. As much as I like being with you, I have a firm rule about relationships with my staff. I will not be in a physical relationship with you if you come to work for me. It simply causes too much difficulty, frankly more for you than for me. Your staff will not respect you if they think you are the manager because I have special feelings for you. Does that make sense?"

"On the surface, intellectually, it makes perfect sense Harry. Inside I must admit that I'm a little disappointed. I really didn't know where this evening would lead but have been curious since Saturday. Let's discuss the job some more. I will abide by your decision regarding our relationship."

"I understand, Carolyn. When I picked you up tonight I nearly changed my mind about offering you the job. I admit I'm a bit smitten with you. It isn't so much how you look, although that is a huge part of it, but it is your personality. You are a charming person who also happens to be a curiously seductive woman. However, I must remain firm on my policy. It will be up to you which direction our relationship progresses."

"Oh Harry, you are so kind. I had hoped to be attractive to you. I guess I'll have to do some soul searching. For now, let's proceed."

"Here's how I envision the process, Carolyn, if you accept this offer. I have been investigating some properties and am close to a decision. There is one building that would be perfect but will take significant renovation. However, I expected this and am not concerned. Frankly, it will buy us the time to get you indoctrinated to how I run my businesses."

"If you decide to come to work for me, I would like you to begin as soon as possible by reporting to a few of my clubs, meeting the managers and learning how they do their jobs. I have some simple but iron clad rules that everyone follows. I doubt that, with your prior experience, you'll find them unreasonable."

"I would expect you to be totally professional as a manager of the club. To me this means business wear at all times. While I love your look tonight, I would deem it inappropriate for work. Do you agree?"

"Of course, Harry. I already have two business suits and will have no problem purchasing more. I rather enjoy the professional look and will be happy to dress according to your wishes."

"I compensate my managers with a combination of base salary plus a quarterly bonus based upon the actual profit of their club. As a base I can offer you $80,000 per year. If the club turns the profit I expect, you should be able to earn between $5,000 to $10,000 per quarter. Does that sound feasible?"

"It may work, Harry. I'll have to eliminate my trading. These past few days I haven't touched my work and frankly, if I come to work for you I can't see giving you anything less than a full time effort. What hours would you want me at the club?"

"That is up to you. Most of my managers come in around noon and are there until closing. On weekends, that means a 12 hour shift. However, I insist that all employees only work a 5 day week. I know the hours are demanding but in this business there isn't much choice."

"That sounds reasonable. Talk with me about staffing."

"Good question, Carolyn. Ideally, I would like a good mix of transgendered people working at the club. I know we can't discriminate nor would I want to force anyone to adopt another gender as you have. However, I think that would add some fun and spice to the club. What is your opinion?"

"I certainly agree but I'm not sure how to go about it. It will be an interesting challenge. Do you feel that woman to male candidates would be fitting?"

"Why of course! That would be even more fun. At the same time, our focus must be on quality personnel. You can't accept prima donnas of either sex. Running a club with a restaurant requires hard work and teamwork from everyone."

"Ok, Harry. This does sound like a neat opportunity. Can I have tonight to think about it? I may have some questions that just don't pop into my mind."

"Of course, my dear. You take a day or two if you wish. Once you agree, I want to move forward quickly. For now, let's order our dinner. I'm getting pretty hungry too!"

He signaled the waiter and we ordered our food. It was as if a switch were flipped. Harry was suddenly interested in hearing about the changes I had made since we saw each other last. I told him about my breast forms, my wax and hairdo. I had fun regaling him about my various shopping sprees and most of the things I had acquired.

I decided against discussing waist cinchers, garter belts and stockings. If he was going to stick to his employee relationships rule, there was no sense in sharing every intimate detail. Certainly I would NOT talk with him about dildos!

We ate a fine dinner and had an after dinner drink. Harry ordered a scotch and I had Benedictine.

"May I smoke, Carolyn?" he asked.

"Of course, dear. I'll have one too if it is ok."

I reached into my purse and took out my Virginia Slims. It had been awhile since I had a cigarette and I was looking forward to it. Harry reached across the table holding his lighter for me. As I leaned forward, I noticed him peeking at my cleavage. Poor boy – he wasn't going to have fun with those tonight.

As I smoked I noted with a smile the lipstick on my cigarette. It was pretty sensuous for some reason.

Since we were in a secluded area, I decided to tease Harry a bit.

"I want you to know, Darling, that I understand and respect you rules of employment. If I decide to come to work for you, I am quite content to have a pure employee relationship with you. I'll work hard to be your top manager and I expect you'll be proud of me and happy that you gave me this opportunity."

"I must admit I am disappointed. I had such a wonderful fantasy for tonight. I envisioned inviting you in for a nightcap and feeling your kisses on my lips and body. I still tingle remembering them from Saturday."

"In my fantasy, I ask you to wait while I change into something comfortable. I have a beautiful while satin gown with a darling lacy robe I was going to wear. I chose white because I am a virgin, Harry. I've never been with a man."

"My hope was to seduce you into my bed and have you make love to me as a woman. I long to feel you enter me and gently rock me until we both explode. I wanted to feel you, Harry. I wanted you to take my virginity. I wanted to be your woman tonight."

"My fantasy doesn't end there. I envisioned falling to sleep in each other's arms. I would wake up before you and have your first waking thought be my mouth gently sucking you to erection. I remember the feel of you in my mouth and the ecstasy of your eruption and the delicious taste of your sperm."

"I wanted this fantasy to be come true, Harry. I really did."

I sat forward as I quietly shared all this with him. He was squirming! I could tell he was oh so ready! I smiled as sat back.

"But alas, my dear Harry", I said with a sad smile. "This will never happen. You must know now how much I respect you as a businessman."

"Carolyn, that fantasy of yours is not far from my own. You know," he said with a sly grin," you haven't accepted the job yet. Technically you are not an employee so perhaps the rules don't have to be enforced tonight."

Inwardly I smiled. I had hoped he would go down this path.

"Oh Harry!" I exclaimed. "I would never want anyone to think that I slept with the boss to get my job! How would I ever command the respect of my staff? You know you're a handsome man, dear. Running a business is difficult enough without dealing with jealousy and resentment."

He sat back and smiled. "You're right, of course. I apologize for even suggesting it. But understand, Carolyn, that you seduced me quite thoroughly. I won't be able to stand up for another five minutes! I imagine our night would have been tremendous for both of us."

He took my hand. "Let's just have one dance, my beauty, and then we should go."

We stood up and moved to the dance floor on the other side of the room. I melted into his arms and swayed as he held me tightly. I felt him pushing into me and smiled. I guess I had acted as sexy as I felt.

We finished our dance, got my coat and left. The ride home had a surprise.

"Oh, one more thing," Harry said. "I was thinking about a name for the club and came up with Club Carolyn. Of course, that's too obvious, but what do you think about CC's?

"Harry, it is a great choice. I can hear people saying 'I'll meet you at CC's.'"

When we got to my house, Harry walked me to the door.

"I'll have my attorney draft an offer letter to you, Carolyn. If you have any other questions, we can amend the letter before you sign. I hope you accept the job. Something tells me we'll make a good team, run a profitable club and have fun doing it."

"Ok Harry" I responded. "I'm leaning very seriously toward accepting the position. I'll have a lot of shopping to do but that's fun for me and won't be a problem. Have the letter delivered to me when it is ready and I'll have a decision within 24 hours of receipt."

"Thank you for a wonderful evening, Harry dear. I wish it could have been more but in the long run, I know we'll be glad we stuck to your rules. Would it be stepping too far over the line to seal our deal with a kiss?"

He smiled and pulled me to him as we stood at my door. His lips fell softly on mine. I teased him with my tongue and he opened for me. It was a delicious kiss, lasting over a minute before I pulled back.

"Thank you dear but we have to stop. It is all I can do to open this door and go into the house alone!"

"You're quite a gal, Carolyn. I can't remember the last time I felt so unsatisfied! I admire your principals but wish I didn't have my silly rule. I know in the light of day I'll be glad you are a strong woman but tonight is another story."

With that he left. I stood behind the closed door trembling. Oh how I ached for him. I knew I had done the right thing. No one night stands for this girl.

It was only 10:30. I wondered if Suzy would be home. Without changing, I called her.

When I heard her voice on the line I actually shivered!

"Suzy, I just got home. Do you feel like a glass of wine?"

"Hi Carolyn, what a nice surprise! I'd love one."

"Wonderful. Do you mind coming here? I'm dying to tell you about Harry!"

"I'll be there in 15 minutes."

"Ok dear – toodles!"

I decided not to change until she arrived. I wanted her to see my outfit. I went to the bedroom to fix my make up and spritz a light dose of perfume.

Of course, I was fully enjoying the short skirt, now that I was home. I sat down and purposely let the dress ride up to expose the second shade of my stocking. I felt sexy and was excited that my Suzy was on the way to see me. Perhaps the night would evolve into a different fantasy than I had shared with Harry.

"Carolyn," I thought to myself, "you're insatiable!"

I waited impatiently.

  

  

  

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