Jackie Pt. 03


This story is being written by Jackie as a narrative of her progression from sexually inactive, to widower, to sexual active, to millionaire.


The Weekend before the Grand Opening

I walked over to Shannon’s Saturday morning to have breakfast and ride with her to Anna’s.

“I saw you and Edward walk out last night so I know your plan worked. How was it?” Shannon asked.

“I had a fantasy that was beyond what should be expected for a 50-year-old grandmother. And it beat my expectations. It was out of sight. Indescribable. Why were you there so late?”

“I was worried about you. But when I saw you and Edward walking arm in arm to the car with your ass beet red, I knew it was good.” I could only smile and wink at her. Shannon was happy for me. “Did you get a package from Edward?”

“I did.”

I had a package with a $5000 check and a note Friday night when I got home. It said the money was a bonus for the initiative taken at Phantoms and that it should be invested not spent. Shannon’s showed me her note saying almost the same thing. The only difference was it said Shannon should talk to me about what to do with the money.

“My notes said to invest it,” I started. “Monday when I went to see Edward he was on the phone talking to someone about an investment he is making in a company called Solvent Pharmaceutical. I think he is telling us to buy that stock. On the phone he said he had knowledge that a drug would be approved with 4 weeks and the stock could go from 1 to 10 dollars on the announcement.”

“I think we should do what he wants,” Shannon said pensively. “Remember Anna said he helped some people without calling attention to it. Let’s open an online brokerage account, deposit the check, and buy the stock. We can do it tonight when we get back from Anna’s.”

“Sounds good to me. I don’t feel right about taking the money but it is Edward’s money and we should do with it as he wants. Yes, let’s pick up sometime to eat, a bottle of wine, and have stock purchase party.”

We went to Anna’s. Again spending most of the day picking out outfits. We got 2 more outfits we could wear during the week and spent most of the time finding something to wear to the open house. After a lot of tries I picked a Halston Heritage tulip green evening gown. The V neckline plunged to the waist. It had stays and padding that kept my breast in place. It pressed them together so there was a mound of flesh on my chest. The back also plunged to waist showing almost all my broad back. Anna thought it looked glamorous. Shannon’s was very similar but blue. They were second hand so it saved Edward a little money and kept us well under Edward’s budget.

Anna also helped be with a pair of designer’s jeans. They molded to my ass and looked quite sexy. I also picked out a white tube top that did not come close to covering either the top or bottom of my breast. Was not sure where I would wear it but who knows.

Anna also convinced us to try a pair of micro thong, three strings really, that had dangling glass stones hanging over the pussy lips. Anna said, “Edward will probably like this as much as no panties with really short skirts. But he may also spank you.”

Again we wanted a swimsuit and gym outfit. Shannon pick a gym outfit that look a lot like a red bikini. The top did have more support than normal bikini. I struggled to find anything. I kept going to a sports bra. Then Anna showed me a yoga outfit that fit like a second skin. The top of the outfit had a deep U neckline that showed a lot of cleavage but plenty of support. It was dark blue with strips along each side that accentuated my hour glass figure.

Anna said as I looked in the mirror, “That is sexier than showing skin. Edward is going to love it.”

“I agree,” Shannon said.

I wanted a 2-piece swimsuit this time. None of the bikinis had enough support on top. So Anna but together a bikini bottom with a cotton bustier bra that could be worn with or without straps. They were both black. The bottoms covered my pussy nicely but left most of my butt exposed.

Shannon got really daring as she chose a nearly see through orange glow micro bikini. The material covered her tits and pussy but it was almost see though dry. I was sure wet it would be see through. Shannon was really in this now.

We thanked Anna, collected our stuff, got dinner and a bottle of wine, went to Shannon’s condo, had dinner and opened an online brokerage account for each of us.

Lunch with Tiffany

On Sunday, my wild child daughter had arranged for us to have lunch at a restaurant between where we lived. She made it clear it was her treat. Tiffany had really changed her attitude toward me the last few months. Instead of avoiding me, she seemed to want a relationship.

“Hi mom,” Tiffany said as I entered the restaurant. “Boy you look good. In fact, you are gorgeous. I knew you were working out but man I did not expect this.”

“Thanks dear. And you too antep escort bayan but you have always been gorgeous. So how have you been?”

We ordered a glass of wine each and a light lunch. The food was very good leaning more to tasty low calorie. Tiffany had chosen well. Most of the lunch we spent making small talk. Every time we got to our jobs the conversion got stranded and vague. We had a second glass of wine and kept talking after the dishes were cleared.

Finally, Tiffany said, “Mom, I want us to get closer and if we don’t open up to each other about what we are doing, I don’t think we can have the relationship I want.”

“You are right. Let’s show each other our cards. Want to come to my condo so we can talk openly?”

She paid the bill and followed me to the condo. It was about 3pm. I fixed us each a cup of tea and we sat on the patio. It was a lovely day in Florida and my patio was in the shade.

“I will go first,” I said. So I told her all about the club and my role in it. The only thing I left out was my tryst with Henry and the punishment by Edward. I ended by showing her one of our flyers with me in the leather outfit being led by Edward. “That is me,” I said pointing to me in the picture.

“Mom!” Tiffany yelled and laughed simultaneously. “You are a vixen.” I smiled and laughed with her.

“Would you have ever imagined me in a picture like that?”

“No! You and dad were so straight. However, it does help me understand me. We are more alike than I would have ever known which makes it easier for me to tell my story. Let me start with an apology. I wasted your money by going to college for that year. All I did was party and of course my grades showed it. I really am not that dumb.”

“I know dear and no need to apologize. That is part of being a parent.”

“I really did feel guilty so I was not going back to college but I had no plan. I decided I had to get away from Detroit. I did not want to embarrass you and dad. More than that I wanted the freedom to do what I wanted without guilt. So I moved down here. It was almost by accident. I could not believe it when Francis moved down also. The first couple of years I worked in strip clubs making good money but I wanted more. I became friends with one of the bouncer at my primary club. His name is Early. Over a period of a few weeks we discussed starting a business together. I had sex with a few guys but was very selective about my clients and only he knew I was doing this. I only dated rich guys that I trusted. They paid me $1000 per night and usually it was to show off a beautiful woman in a sexy dress. Yes, I would have sex but it was part of the evening and was occasional. I did not do drugs. Early and I agreed to a 50/50 partnership. We put in equal amounts of funds to start the business.

“We hired a lawyer to work through the legal documents, formed an LLC called TifEarly Escorts, and hired three girls and one guy. I was in charge of the talent, developing new business, and he did security and accounting. We rented a small office space in a high end location and off we went. Long story short the business took off. To start with, I kept my 3 regular clients which helped with cash flow. I had a couple other guys who wanted services and the 3 girls brought in some business. Of course Orlando is convention heaven. The hardest part was vetting the potential clients. But we managed it. The business made money from the start and Early and I have added more and more services. One of our most lucrative is bachelor and bachelorette parties. We have even done some swinger parties but charge a very high rate for it.”

“Tell me more about the bachelor parties?”

“It can take many forms, but usually there is a strip show with a lap dance for the groom and best man. Many times we then offer lap dances and many times the girls will have sex with the attendees for a price. This is one of the few times we charge separately for the sex act. We make a lot of money at these. Why does that interest you?”

“Finish your story dear and I will tell you. I want to think while you finish.”

“So I am now 25 and co-owner of a very successful business. I am mostly management now although I still do shows occasionally for the right client. I live in a large house and it is time for you to see it and how I live. I have one more thing to admit to you. But before I make this last admission I would like a glass of wine and give you an opportunity to berate me.”

“My baby girl, I have only admiration for what you have done. You are a smart business woman who used the assets she had. In fact, I think you and I are doing the same thing. So no judgment on my part. It is close to dinner time. Do you want to stay with me tonight and drive home tomorrow? I would also like to invite Shannon over to discuss a business opportunity for your company. Is that OK?

“Fine by me but I am intrigued,” Tiffany said.

Shannon said she would araban escort bayan be happy to come over at 6:30 for a salad, meet my daughter, and discuss a way to do Tyler’s bachelor party.

We got a glass of wine and went back to the patio. “Mom this is the hardest thing for me to admit. When you called me to tell me dad was dying, something kicked in that incented me to have a child. I really can’t explain it but that just seems to be the way I work. But I did not want to get married. So I asked Early if he would father my baby without the need to get married. The business could afford for me to manage only for a year anyway. When I came to dad’s funeral I was 3 months pregnant. I had a baby girl named Carly 6 months ago. Of course she is named for dad.”

I started crying. Tiffany came over and hugged me saying, “I am so sorry.”

“Sorry!” I exclaimed. “I could not be happier. I just regret that we are so busy it will be next Sunday before I can see her. Baby girl, nothing could make me happier that reconnecting with my daughter and finding a second grand baby especially a girl.”

We hugged and cried together for a little. Finally, I said, “Let’s fix dinner.” We both needed something to do to get us back to normal. But I was on cloud nine. This was one of the best days of my life. We were just finishing three big salads when Shannon knocked on the door.

I introduced Tiffany and Shannon said, “I would have known this was your daughter from a mile away. It is uncanny. I am so happy to meet you.”

“And I you. Mom said you were her best friend although I am going to give you a run for that position.”

“Oh no competition. I could never replace you but Jackie is big hearted enough to share.”

“Yes, she is,” Tiffany said.

“Hey, I am standing here.”

We discussed Tyler’s bachelor party. Tiffany had a lot of good ideas. It seemed clear that TifEarly Escorts could help us do the bachelor party in two weeks. We soon turned to how The Swinger Club and TifEarly could partner together on other special events. We talked until almost 10pm, when Shannon walked back to her condo.

As Shannon was leaving she said, “Tiffany can you be there at the meeting at 9 with Edward and discuss this with him?”

“I am going to follow Mom to The Swinger Club and swim lap with you tomorrow morning and attend the meeting. I have to leave right after but I am sure we can get the agreements done next week if Edward approves.”

“It was great to meet you,” Shannon said as hugging Tiffany.

Tiffany proposes a partnership between TifEarly Escorts and The Swinger Club

Tiffany slept in my second bedroom. Tiffany dressed in my Red Cross swimsuit from the week before. She looked great. I wore the new one from Anna’s. “Mom I can’t believe you are now wearing these suits. Not in my wildest dreams could I picture you in them. But I have to admit you look great.”

“You look good in it also,” I said.

We got to the locker room with Shannon as Edward was leaving. “Edward this is my daughter Tiffany.”

“Nice to meet you Tiffany. I would have picked you out of a line up as being related to Jackie. Although I would have guessed younger sister. That is your mother does not look old enough-. Ok let me stop digging.”

I laughed and said, “Shannon and I have an idea of how to do the bachelor party for Tyler with Tiffany’s help. She will be joining us at the 9am meeting. Ok?”

“I look forward to it. I really want to do it but on the verge of saying forget it.”

“Us also,” Shannon said, “but Tiffany, I think, will convince you we can. Want to see the new suit options?” We all three removed our beach covers.

“While, it is hard to pick but I have to give the nod to Shannon’s suit. What does it look like wet? I mean there is only the hint of cover dry, will it all show when wet?”

“I think so,” Shannon said. She looked like she knew it was a knockout.

“Don’t get me wrong, Tiffany and Jackie look extremely sexy but Shannon’s suit is unique. What is it called?”

“It is called a Micro Thong Bikini by FantasiaWear. Anna has a line of these. This one is not the most provocative. I am thinking we should have a day of modeling these. I think it would be a hit.”

“Great idea, let discuss after the Tyler Party decision. See you girls at 9.”

So we did our laps and dressed for the day. Shannon and I wore one of new outfits from the last shopping trip to Anna’s. Tiffany wore her outfit from the day before which was a business suit, far more conservative that the outfits we wore.

“Is this the way you guys dress everyday?” Tiffany asked.

“Yes it is,” I said. “Remember the motif of the club and what we are trying to project.”

“It makes sense,” Tiffany said. “But it is not often I am the least provocatively dressed.”

“Just don’t wear underwear,” Shannon said.

“What?” Tiffany said.

“Edward does not like panties,” gaziantep arap escort bayan Shannon said. “It will impress him if he checks you.”

Tiffany looked at me and all I could do was shrug. “Ok,” Tiffany said as she removed her panties.

It was just us three in the meeting with Edward. “Ok, what is the big idea?”

Tiffany said, “Let me start by explaining my company.” She then repeated a description of her company. As she talked I could see Edward knew where this was going. Tiffany was also very polished in her presentation and she could see that Edward was sold. So she cut short many of the details she and Shannon had discussed.

She ended the monologue saying, “Shannon and I have discussed a lot of details that would make this party a success and make The Swinger Club a premiere option for Sexually Oriented Parties. My proposal is to let our lawyers work through the legal details this week. I will give Shannon my phone number and we can work up details for the party.”

“Well, you are very persuasive. You and your mother have a real head for business. Please step outside so we can discuss it.”

“No problem,” Tiffany said as she stood.

“Before you go, describe your panties.”

“What?” Tiffany said as if she had not expected it.

“I know it is a strange question in a business discussion but I find the answer is a good indicator of good business relationship. I assume the party is the first step in a partnership with The Swinger Club.”

“It is a strange question. I do see this as a lucrative partnership for both companies. The answer is why would you think I am wearing panties at all? After all, why would you cover a beautiful part of my body with panties.”

“Exactly. Can I see?”

“Sure, after all if we go into business together you will see it plenty.” Tiffany raised her skirt and showed him a bald, beautiful pussy that had a landing strip in the V of her groin. Tiffany was smiling and said, “Do you like?”

“Who wouldn’t?” Edward said. “Thank you Tiffany.” Tiffany left the room.

“What do you think Shannon?” Edward asked.

“This is a gift. I am certain with Tiffany’s help we can do this event and many more. It is a perfect partnership for us.”

“I agree; it is a no brainer. Jackie is this really OK with you. I mean this is your daughter you will likely see prostitute herself. My concern here is your relationship with your daughter.”

“Thanks for asking but this is a no brainer. I have found out in the last few weeks that Tiffany is my daughter from head to toe. I know myself better now than ever and Tiffany is me. This partnership will bring us closer together not apart. I love my daughter and this is what we want.”

“Then easy decision, let’s do it. Shannon call Tiffany back in.”

He reached out his hand to shake. Tiffany shook Edward’s hand saying, “Let our lawyers work out the details. I think my lawyer can help make it very difficult for either of us to have legal problems. Let me also say it is ingenious how you have put this together. I don’t think you can be touched.”

“I want this agreement to be a long term basis of our relationship with the party being the first step.”

“Me too,” Tiffany said as she stood close to Edward. “I have a superstition also. I like for my potential business partners to kiss my ass. What about it?” Tiffany winked at me.

“My pleasure,” Edward said. He reached for Tiffany’s hip, pulled up her skirt and kissed both cheeks.

“Shannon?” Tiffany said. Shannon smacked Tiffany’s ass raised her skirt for Tiffany to reciprocate.

“Let me get a little of that love also,” I said as I slapped Tiffany’s ass.

“I will call you tonight Mom, and Shannon call me anytime. Lots to work out.” With that Tiffany left and I was so proud of my youngest daughter.

“You 2 girls have done great. This is going to work. I have a sense this was the final significant piece falling into place.”

We agreed. The rest of the week was phone calls and meetings for me. Shannon was busy getting the club ready for the Open House and talked to Tiffany every day about the party. Both were coming together.

The Open House

The night came for the Open House. I had 154 people respond that they would be at the event. We had to keep this night PG and mostly it was to be presentations from Edward, Shannon, myself, and Bruce about the club. Shannon and I worked most of Saturday on the room in jeans and tee shirts with Edward’s permission. He also wore jeans. It was to be first class food, well dressed waiters and waitresses, valets, the works. Edward, Shannon and I showered together at 6pm with guests to arrive at 7. Shannon and I wore our Halston Heritage gown and Edward a tuxedo.

Before we left the locker room Edward said, “I could not be prouder of what we have done together. You are both beautiful and have exceeded all my expectations. You both have grown since we started. Now let’s go present our best.”

Shannon and I were both touched by his statement. I knew he meant it.

As the guest entered, I checked their names against my list and gave name tags. I remembered many of them as they entered and did not have to ask their names. Shannon, Edward and Bruce introduced themselves and greeted each after me. Then the servers got them drinks and snacks.

This story is being written by Jackie as a narrative of her progression from sexually inactive, to widower, to sexual active, to millionaire. Edited by DRGRIFFIN The Weekend before the Grand Opening I walked over to Shannon’s Saturday morning to have breakfast and ride with her to Anna’s. “I saw you and Edward walk out…

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