Jackie Pt. 01

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This story is being written by Jackie as a narrative of her going from sexually inactive, to widower, to sexually active, to millionaire. Many of the characters are older so keep that in mind before reading. Also Edward dominants female employees which you may find objectionable.




Hi, my name is Jackie. I am now a 55-year-old widower. I have become a millionaire in the 5 years since my husband, Carl, died.

I met Carl in college. I was a freshman in the English Department. Carl was a senior getting a BS degree in Engineering. We married as he was graduating with a job that moved us to Detroit, where we lived until Carl’s death. I was 19 when we married and not bad looking but not the prettiest girl around. I was 5 foot 6 inches tall, 36 D top, 27-inch waist and full 39-inch hips. While not overweight at all I was not small either. I had very black wavy hair, blue eyes, full lips, and a big laugh.

I became a stay at home mom with two girls. One of my girls, Francis, graduated from college, married, and moved to Florida. She was very responsible. They had one little boy at Carl’s death and making a good living in Florida.

My other girl was a wild child, Tiffany. She moved south after dropping out of college and never discussed how she made money. But to her credit she never asked for anything. She was a better looking version of me. She was more endowed up top than me at her age and worked at her looks more than I ever did.

Carl made a good living and I thought we were heading to a comfortable retirement. Our only real extravagance was belonging to a country club in Detroit. Carl loved golf and was very good at it. While I did not play golf, I did enjoy riding with Carl and acting as a caddy. Carl had a light bag that I carried on for him when he did not want to ride in a cart. His group seemed to enjoy my company and I certainly enjoyed theirs.

Carl and I had a very traditional life including our sex lives. Carl lost interest in sex as he hit 50 and seemed that I did also. It was not soon after he was diagnosed with terminal cancer with the only question being how long it would take. Of course, I know the answer now was 3 years. I was 47 and had stayed physically fit. The biggest change was to get a larger and fuller up top with my bra size becoming a DD. I also picked up a couple inches in the waist and hip.

When Carl started the chemo treatment he could not work. He did get a medical leave. He needed a lot of assistance both when he was home and several periods of weeks in the hospital. The cancer just simply ate him away and by the time he died we were both ready for it to happen. The 2 plus years I took care of Carl I let myself go. The stress was just so hard to contend with I ate all the time. I was big all over but my boobs seemed like balloons that kept growing and my ass could have its own zip code. I did not weigh but I was probably about 200 lbs.

For the last 6 months Carl had hospice care. While Carl was very sick which made me sad, it did help me as Carl wanted me to get out of the house. So I started going to the Gym and indoor lap pool at the club almost everyday. It was a great stress reliever to exercise. I also changed my eating habits. I dropped close to 50 pounds in those 6 months and firmed up all over. My boobs however stayed large, a 37G cup. My breasts were round, full, and very white which made the large dark areola really stand out. My nipple also could get large and protrude when played with. There was some sag of my breast when turned loose but I did not look like a grandmother. I was 41 to 42 in the hips with very full heavy cheeks. I had a flat stomach but my waist was 32 inches. I was what most people would call a BBW. I weighed 160, was very strong for a women and in good aerobic condition.

Before Carl died we had time to review our finances. Well, to say the least it was depressing. We owned our house but prices were depressed at the time in Detroit. The insurance had paid a lot of the cost for Carl’s care but far from all. The remainder ate up most of our savings. We agreed that I should sell the house as soon as I could after Carl died and move South to Orlando close to my daughters. Francis wanted me to move close to her. She lived about 50 miles from the wild child. That sounded good to me.

So I sold the house and moved to a small condo in a golf community close to Francis and about an hour’s drive from Tiffany. I had about $300k left after I paid everything off, moved, and bought the condo. This left me about $50k to live on until I could find a job. So I needed to find work soon. I did not want to ask my daughters for financial help, maybe pride but clearly I was too young to start being dependent.

Jackie moves to new location and starts her new life

So I was 50, blue eyes, long dark hair, shapely, somewhat attractive middle age widowed women with little social life in need of a job with no real experience. Beylikdüzü escort My sex life had been non existent for several years now. I was so worried about finding a job, I just could not think about sex. I did not even masturbate.

I started applying for every job under the sun for about 3 months. Most of the jobs I tried to get were as a secretary or clerical. I kept hearing over and over, you have no experience. But how much experience do I need? I knew how to use Word and Excel but it seemed not to matter. Out of desperation, I hired on as a clerk at a local grocery but I did not like it much and it barely covered my basic expenses.

I had two pleasures during this time; the Y was 20 minutes from the condo I bought and my grandbaby which I saw a couple days a week. The Y had an indoor pool and I really enjoyed swimming. I did occasionally see Tiffany and we were becoming friends for the first time. She always seemed to have money and always bought lunch for us and even offered me money. But even with these pleasures, I was depressed. I wanted to find something more meaningful.

For 3 months I clerked and continued to look for another job. I had rejection after rejection. I saw an ad for a local club that was opening soon and looking for an outgoing mature women capable of attracting members to the club. I did have experienced with Country Clubs, so maybe this one would be possible.

I got dressed in my most professional outfit and went to interview with the club’s owner, Edward.

Edward explained to me that this was a golf oriented club that had failed. He bought the property several years before and developed a good portion in high end single family housing.

He did not say so but I think he made a lot of money doing this, keeping the club house on about 50 acres of gorgeous land. He wanted to turn what was remaining into a more exclusive club for open minded people. When I asked what he meant by open minded, he said he was still working on that.

Edward, did want to have a small executive golf course that could be played in under 2 hours, tennis, gym, outdoor and indoor pools, and the Club House had already been modernized with rooms for entertainment, dining, cards, and a game room. He said the appeal would be to men and women that wanted to play in an open minded way.

Again, I asked what he meant by open minded. Edward finally said, “I am thinking that we would have the standard things but add something more sexual in nature. Maybe we have nights for swingers. I had thought single’s club but decided not to limit. If we have waiters and waitresses dressed provocatively or encourage a dress code of a more sexual alluring. Maybe we have theme nights that encourages exhibitionist. I am still working though the details. I have hired a few key positions and they are beginning to hire staff. We are close to opening and I have about 20 people ready to sign up for something like that.”

“What position am I interviewing for?”

“I am thinking of membership manager. I wanted someone more mature and attractive for the position and you fit the bill. I also wanted someone that is open minded about sex. If we are going to advertise an open minded attitude toward sexual activities, then the person out recruiting new members has to represent that attitude. Think you could do that?”

I thought for a long time. Edward patiently waited. I thought to myself, there is no way, you have not even had sex in years. Yes, you are attractive for your age but you are old and certainly not thin. After an extended of time I said, “Can you be more specific about sexual activity I would have to participate in?”

“I don’t mean to be a prostitute but I would expect a look that is seductive. Right now you look like an accountant not a membership manager for a provocative club. I would expect you to help the event manager, go to area gatherings, market, and talk people into joining the club.”

He looked at me expecting me to say something. “You think I can do those things?” I finally asked.

“Can you?” he asked me with a look that seemed to be reading all my thoughts.

“Honestly, I don’t know.”

“Here is what I want to do,” Edward started. “I want you to come back tomorrow morning, dressed like you think this club would like and convince me you can do this job. If you are not here by 9am in the morning, there will be no offer. Understand?”

“I understand.” I stood stuck out my hand to shake saying, “Thank you for your time.”

Edward was an older gentleman; I would guess something above 60. He was maybe 6 feet tall without an ounce of fat. I would guess about 180 pounds with a trim waist. Full head of salt and pepper hair that had a wave that looked kind of gangster when swept back. His face had sharp features, square jaw, sharp check bone and sharp pointed nose. His eye were black and penetrating. I doubted many people challenged him. He was very intimidating. He wore expensive casual clothes Beylikdüzü escort with nothing out of place.

Jackie has a unsettled night

I had an awful night. First could I really do this. I worried that I did not have the social skills to convince people to join Edward’s club. Second, I had not had sex of any kind in four years, how could I project sexuality. Third, I was afraid of Edward. What would he do to me? Fourth, I did not know how to dress provocatively nor did I have anything in my closet that would match this expectation. Fifth, I needed a job that challenged me and this certainly would be a stretch. I slept almost not at all.

At 5am, I looked in my closet for something that was provocative to wear even though I still had not decided to go see Edward versus going to my clerk job. I was supposed to be at the grocery store at 9am. I spent close to an hour looking at what I could wear. I was almost to the point of not deciding on merit but could I even put together a wardrobe which would work.

I could not eat breakfast. I tried on about 10 outfits, looked in the mirror thinking is this provocative? I finally decided on a very old sundress. It had been in my closet forever. The next closest choice was an old evening cocktail dress that was too small but definitely provocative. I hung out everywhere and decided it was more funny than provocative. It was about 8am and I had to leave at 8:30am to be on time for either the club or the grocery. I had to decide. I took one last look in the full length mirror before I called the grocery. I looked frumpy in this. I could not go through it.

So I took off the dress and looked for my grocery outfit, slacks and button up shirt. As I grabbed the slacks, I saw an old white silk blouse that was mostly see through. That would be provocative matched with an undersized black bra. I had a black skirt that would be now very tight with the 2 extra inches on my hips so I put that on. Looked in the mirror. That worked. You could easily see the black bra and because of the small size it pushed a mound of flesh above it had a touch me look. My hips stretched the skirt to its limits and because of that the hemline hiked up above the original fit. I had a pair of black high heal pumps that made my calves very shapely. I thought, you almost look sexy and I felt sexy for the first time in years. Would Edward like it? I wanted to find out because I called the grocery to take the day off.

The drive to see Edward was a mixture of apprehension and excitement. I really could not believe I was doing this. But I was to the point of nothing to lose. Worst case is it does not work out and I am clerking groceries tomorrow, bored and depressed. Which is where I was yesterday. Walking up to the club, I was so glad no one was outside to see me like this.

Edward greeted me and asked me to sit. I slowly crossed my legs making sure he got a good look at thigh.

“I am glad you came back,” Edward said. Edward showed the first emotion I had seen. I saw some level of satisfaction I had not expected. Maybe he liked the outfit.

“I still not sure why you are interested in me but I want to discuss the opportunity,” I said with fear I could not hide it.

The next 2 hours we discussed what he wanted to do with the club and much to my surprise he wanted my opinion. It was so interesting how his mind worked. He discussed a lot his thoughts on getting members and the needs in the community. He made a point that the typical country club was something of a dinosaur. He thought there was a segment that would pay a high price for golf, tennis, pool and dining if they were bundled with a specific set of social activities catered to high income individuals. He thought an open attitude to sexual activities in the club would be very attractive to a select clientele. He wanted to give members an opportunity to socialize with existing members in the most intimate way. He indicted that the 20 people that had committed already were friends and associates that were the types he wanted to focus on. They were all successful high net worth individuals with desires hard to fulfill because of their demanding jobs.

As we discuss the business, I was able to make suggestions that he seemed to like. He also showed interest in my background. He really did listen well.

It was about noon, I could not believe it was so late, and he asked, “Ready for lunch? There is a place close.”

I was panicked. Did he really mean for me to go out in public with my tits hanging out? “Oh, you mean eat here at the club?”

“The kitchen is not open yet. No let’s go to Ernie’s Deli, it has good sandwich and salad with quality wine.”

What was I going to do? Did I really want to display myself in public? Again I decided what is there to lose. I don’t know many people here anyway. “Yep let’s go.”

Heads did turn as we entered the deli. Everyone seemed to know him as he introduced me to many people. I was excited by Escort Beylikdüzü this. People stared but in a good way. My chest was a hit with all the men it seemed and most of the women noticed. I had a distinctly good feeling in my groin.

We were seated, and ordered a glass of white wine for me and a bourbon and water for Edward. We continued to discuss the business. I was buying into his vision. He really had spent a lot of time working on this plan. I realized I wanted badly to be a part of this.

“What do you think of me being involved with this venture?” I asked.

“I think you could do it but it would require a lot of work and change on your part.”

The waiter came with our lunch order and we both ordered second drinks. “I know I am not qualified for this job but working hard is not an issue. I will give it my all if you give me a chance.”

“Let’s eat, I want to think for a little.” I got the hint and shut up while we ate.

We finished our food and second drinks. I was struggling to keep my shirt down. I could see that people were staring at the spectacle of too much woman in too small of a skirt. The waiter came and cleared to table. It was close to 2pm by now.

“Want any other glass of wine?” Edward asked.

“If I do you may have to carry me out,” I said laughing. I gave him my best smile.

“Oh come on. I don’t mind having a drunk attractive woman by my side. I am going to have another. There is one more thing I want to discuss before deciding.”


The drinks came as Edward said, “I want all people who work as key members of the management team to be fully involved in the kind of lifestyle the club endorses. Do you know what I mean?”

“You mean open minded about sexual connotation the club will be endorsing?”

“Yes, but more than that I will demanding that you do things you may not want to.”

“How will I know I don’t want to do it something before I am asked?”

“You don’t and that was a great answer. What I am asking you is do you want to try for more adventure in your sex life even if I were to tell you what those are now you would probably say no. Let me ask you, yesterday would you have agreed to wear a sheer blouse with a too tight and revealing bra and a very tight skirt to a place like this?”


“And how do you like it now?”

“I love the attention and having feelings I have not felt in a long time. It has been forever since I experienced this attraction. And it feels good.”

“I will offer you $40k starting salary and increase the salary with every 5 new members until we hit 100. With that milestone you will be making $100k. Want the job?”


“Let go back to the office and sign the agreement.”

I finished my wine and walked a reasonably straight line to the door of the deli. At the office, Edward could have fucked me then and there if he wanted. I wanted sex for the first time in a long time. He handed me first a release. It released the club for all sexual harassment claims. I signed without thinking about what I was doing. Then the employment contract laid out the terms Edward had described. We shook hands and I left the club with instructions to be there at 9am the next morning. I called the grocery and quit. The manager was not surprised.

Jackie prepares for new job

When Edward showed me around the club, the gym and indoor pool were ready for use. I decided to ask Edward if I could use them but had gone to the Y that morning to swim. When I got home I was again faced with the ‘what to wear dilemma’ I had the day before. This time I decided to not worry and put on a blouse and slacks. It was nice casual.

I got to the office and started organizing my desk. I was to meet with Edward at 10. In his office was another woman.

“Jackie this is Shannon,” Edward said. “She is the new Director of Events. Shannon this is Jackie the Director of Membership. We will be working together closely the next few weeks. I want to have a Grand Opening in three weeks. I know it is too soon but let’s do it anyway.”

Shannon was about 25, tall, thin, blond, and pretty. I would guess that she was a B cup with a firm ass. She had a degree in hotel management.

We spent most of the day discussing how to attract people for opening day. In the end, I was to organize the online marketing effort and trips out in the community to get attendees and Shannon focused on getting the club ready for the opening night event. Edward wanted to make certain that people knew we were going to be a club catering to the swinger lifestyle.

“Let’s talk about name,” I said. “If I start working with the web developer on the web site we have to know the name and emphasize the nature of the club. Have you thought of a name?”

“No, what do you two think?”

“Why don’t we call it The Swinger Club?” Shannon said. “We have golf, tennis, and swinger parties.”

“I think that is perfect,” I said.

“Yep, that was my top choice,” Edward said. “The other was Anything Goes Club.”

“Why not make that our tag line,” I said. “The Swingers Club Where Anything Goes.”

“What do you think should be on the front page of the website and our marketing flyer?” Edward asked.

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