Jackie Pt. 04

This story is being written by Jackie as a narrative of her progression from sexually inactive, to widower, to sexual active, to millionaire. Many characters are older so don't read if you are looking for young.

The Week after our first bachelor party

I was signing up new members almost every day now with 52 primary memberships with 10 associates. I had scheduled 7 more sign up today.

Edward said, "John Knight, the owner of the Orlando City Soccer Club, called me yesterday to tell me he thought we were going to be successful with this concept. He said the bachelor party was the best run party he has observed. He indicated that Jackie and he had a long conversation while everyone else were otherwise engaged." He looked at Shannon and smiled. Shannon just gave him her innocent girl look. "He wants to bring his wife around 5 to discuss a membership with Jackie. He wanted his wife Marilyn to meet Jackie before they made a final decision. I know we are supposed to be off on Monday's and we will get there but this is important."

"Absolutely," I exclaimed. "I know he would be an important get." Everyone else agreed to stay until they heard from Jackie.

Shannon laid out the week of events. She planned Flexible Clothing Dining Tuesday, Friday, and Saturday. We are going to have the servers model swimwear from Anna and 2 others vendors on Tuesday and Friday. Anna will have price lists and order sheets available for the servers to distribute. Anna was beginning to stock the shop with swim suits, gym and tennis clothes. Anna was paying us a leasing fee but she kept profits from the shop itself. The golf shop had not opened yet.

We had made a policy that anyone participating in a Swinger event would be required to have a current STD test on record plus they would have to be couples. The first Swinger Night would be a week from Saturday. This Saturday night she wanted to have a combination lingerie modeling and dining. The servers would also model the things they liked. Shannon said she was discussing with Tiffany the idea that some of her crew would model and hand out cards to TifEarly. This would be lead up to the first Swinger Saturday themed as the Swinger's Pajama Party. We all thought that sounded good.

Bruce said he signing up tennis players for lessons and tournaments. He wanted our input on a creative way to spice up a tournament or league. He is thinking of a handicapping based on outfits. Any suggestions would be appreciated. The golf course was barely opened and we had just hired a golf pro. His first day was tomorrow. With that we adjourned. The remainder of the day I signed up new members.

John and Marilyn Knight arrived a little after 5pm. John was dressed in his typical business attire. She was dressed to impress any man she met. It was very similar to my red knit I wore the first day after seeing Anna. It clung to her like a second skin. It barely covered her ass and any man would think if he watched a little longer he could see her cheeks. Her ass was as broad as mine but not as fat. I was sure I would get to see it soon. Her tits were not quite as large as mine but she was not wearing a bra and there was little sag. I had a feeling John had paid for these and they were being displayed every day. The dress neck line was cut where the top half of her breast showed. Marilyn looked like Anna Nicole Smith. Broad face, wide set big eyes, and platinum blond hair.

"Good to see you Jackie," John said as he extended his hand.

"And you to," I said as we shook.

Marilyn grabbed my shoulder and gave me air kisses on each cheek, European style. "I know we are going to be friends," Marilyn whispered. "John, is so infatuated with you and so am I. You are beautiful."

"Thank you Marilyn. John has told me so much about you and I think we are going to be very good friends. Please have a seat. Tell me about yourself."

She flashed a bald pussy at me as she sat and she knew it. She talked for 10 minutes without stopping. She was a model when she met John. He had married her within a month of meeting.

She stopped and asked, "Tell me about the club."

So I spent the next 10 minutes telling her about the club. I felt sorry for John as he had heard all of this before. When I finished, "Why don't I show you around."

"Oh would you," Marilyn said with exaggerated appreciation. "That would be so sweet of you."

I first took them to see the Pro Shop. "Do you play golf?"

"I don't but John does."

We then went by the locker room. "So the men and women both use these showers and have lockers together."

"Yes, what do you think of that?"

"I think I will love it. Don't you think we should be proud of our bodies?" Marilyn cooed with a hand on her hip with a bump.

"I do."

We went to the gym and Bruce happened to be there working out with no shirt on and thin nylon short shorts. I had to admit he looked sexy. "Marilyn this is Bruce our Tennis Pro."

"Oh my, John, he is dreamy. Bruce, we are going to be such good friends. John, I want to take tennis lessons." She hugged Bruce making sure to squeeze those big tits as tight as she could against his chest.

"Good to meet you, Marilyn," Bruce managed to get out. "I would be so happy to give you lessons. Have you played much?"

"Well I have been planning for years but I am not very good. I think you can help me."

"Marilyn, do you want to join the club?" John asked Marilyn.

"Why yes. Look at Bruce and Jackie. They are already my best friends and look how beautiful they are."

"Bruce, would you mind showing Marilyn around while Jackie and I do the paper work. Marilyn is that OK with you?"

"Be glad to Mister Knight," Bruce said.

"Bruce can you show me how to use this machine?" Marilyn said. She had her feet up on a leg press showing Bruce a unfettered view of her bald pussy.

"My pleasure Marilyn."

John looked at me rolled his eyes and shrugged. So when we got back to my office John said, "I know what you are thinking. What was he thinking when he married that bimbo? The answer is I love her. She is half my age, has the IQ of an eggplant, and a dog would be a lot more faithful. I can not figure it out but I do."

"Hey, none of my business. But she will light up most of the men in this club. I hope you are alright with that."

"I would rather she get her outlet here than by chance. So let do this." We did the paper work and got the one document ready for Marilyn to sign. I went back to the gym to find Marilyn and her skirt was at her waist and Bruce was stretching her on a mat. It was a sight to see and Bruce was taking it all in.

"Marilyn we need to get you to sign one document. John is ready to go."

Marilyn got up and hugged Bruce without bothering to lower her skirt. "Bruce you are so sweet, thank you." Bruce had both hands on her ass and she liked them there.

"Marilyn, I am going to enjoy teaching you how to play tennis. So glad you are joining the club."

Marilyn let him go and walked to the door without lowering her skirt until she was out of Bruce's eyeshot.

She signed the document. I gave her a list of upcoming activities. She said, "Flexible Clothing Dining, what is that?"

"It is normal country club dining with the twist that you can be dressed any way you wish all the way from nude to priest dress. Basically, it is an invitation to show off. The servers will be dressed provocatively, this week modeling swim suits."

"We will be here at 7pm," Marilyn said without asking John.

"Ok I will put you down. I will probably see you there."

She hugged me and said, "Jackie, you are such a good friend." John and I shook hand as they left.

Flexible Clothing Tuesday

Shannon and I worked out in the gym early. We found two of the female executives, Nancy and Clarice already in gym clothes walking out to go to the gym. They were dressed in standard gym shorts and tee shirt. Shannon and I were in small nylon shorts that ended about 4 inches below our navel. I wore a very sexy short's bra that had dual straps from the neck to support underneath my breast which left most of the upper half of the breasts exposed. Shannon wore half a tank top that was low cut exposing lots of cleavage and ended about 4 inches below her breast and no bra. Her firm C's looked nice this way. Good to be young.

"Hi," I said, "good to see you at the gym."

"We decided this would be more fun than the company gym. Where did you get those outfits?"

"We shop at Anna's. Anna is stocking our shop at the club now. In fact, the next few weeks the Flexible Clothing Dining servers will be modeling swim suits, gym and tennis clothes. Tonight is swim suits. Can you come?"

"I will see if I can make it," Nancy said. Nancy seemed to be the leader.

"I will definitely make it," said Clarice.

"The newsletter is coming out today announcing the upcoming events," Shannon informed.

There were now several people in the gym, both men and women. We had just hired a Gym Manager. He was a 24-year black man, Q, short for Quintin, that had just gotten a master degree in Kinesiology. He was small, well built with dread locks. Very good looking. He had a list of yoga and classes he was scheduling. He also displayed information about his personal training options.

It was clear Nancy and Clarice knew their way around gyms, however, Q gave them a lot of attention. They were both size 8's with C cup, nice shapes, pleasant faces, and mid forties. They seemed to enjoy Q's company. There were 5 guys working out, giving Shannon and I a lot of looks. It think they appreciated our outfits.

Nancy, Clarice, Shannon and I all finished about the same time. Q gave them cards and said, "Look forward to hearing from you."

As we were walking back to the locker room Nancy said, "I saw how those guys looked at you two. It is obvious if we want any attention paid to us we have to work on our outfits."

"It looked like Q was intrigued," I said.

"He just wants us to do personal training with him. Although new outfits might help that."

"It might," I said. "Any way Shannon and I swim laps tomorrow. Want to join us?"

"Sure be glad to join you," Nancy said laughing.

As the four of us got in the shower, three guys joined us. It was very arousing and the guys had a hard time hiding there engorged member. I could see Nancy and Clarice planning to get laid in this shower. I knew it would happen. Nancy and Clarice were beautiful naked. They had nice bodies but needed to neat up their bush.

"Do you get your bush done?" Nancy asked.

"Anna's salon does it, it is located next to her dress shop," I answered.

We got dressed and all left. Nancy and Clarice noticed the no panties but did not say anything.

I got a call first thing Tuesday from Henry. "I want to attend the Flexible Clothing Dining if you will be my guest."

I had wanted to attend just to see how it went so I immediately said, "It would be my pleasure. How many licks do I have to take to be your guest."

Henry laughed knowing I was kidding, "Let's negotiate over dinner. Say 7 tonight?"

"Sounds good." I decided to pick out one of Anna's more risqué swim suits tonight.

I spent the day following up on calls and arrange more signings. It was incredible now that word of mouth was bringing us candidates. Most dropped interest when they heard the initiation fee.

At 5:30, I dropped by to see Shannon. "Are you coming to dinner tonight?" I asked Shannon.

"If you are going, I will skip. I am going to be attending a lot of these. What are you going to wear?"

"I don't know maybe just go nude," I said laughing.

"Anna sent over a few things. See if this one will work." It was a red floor length cocktail dress that was split along the side all the way to the breast. At the waist and the breast there was a small thin gold rope that ties to allow it to be sized to the person. When I tried it, if you looked from either side a broad swath was uncovered completely. In front and back there was about 8 inches of material. There were 2 gold ropes that started at the waist and went over both shoulders. In front attached to the rope was a 4 inch strip of red gathered material that started about mid way of my breasts and extended to the waist. It was made very well but showed lots of skin all over. It was also easily removed. All you had to do was slip the gold ropes off your shoulder, untie the rope at the waist, and the dress dropped to the floor. No bra was possible but it was very sexy.

"Yep this will do."

"No underwear required."

"Will let you know how it goes tomorrow. I am going to get a shower."

While I was waiting for Henry, I inspected the preparations. The dining room was set up with square tables further apart than usual. We had 18 couples on our reserve list. We had one extra table set up just in case. We were using very comfortable soft love seats with a removable covers for cleaning. The tables moved easily.

The servers were getting place settings ready. They had selected their outfits already and I was surprised by what they had chosen. We had three female servers and two males. They were all between 21 and 25 and all 5 had hard bodies. I had expected them to select conservative swim suits which for Anna would still be sexy. Two of the girls wore micro bikinis that were 3 oval patches of materials with strings. One was a orange material and the other was leopard print. The other girl wore a bikini cut suit that was flesh with material that was mesh and see through. It was almost like wearing nothing. The guys both wore thin clinging suits that were about 4 inches wide. Not sure what they were going to do if they got a hard on and I was sure they would.

"Well I don't think tips are going to be an issue. You folks are really sexy looking."

"Thanks Miss Jackie," one of the guys said. "And so do you."

"Thank you."

It all looked ready. At 6:45 the first diner arrived. It was Nancy with a guy half her age and Clarice with a guy that was about her age. There dates removed their wraps to reveal what they were wearing. Nancy was wearing a black sequenced cocktail dress that barely covered her bottom. It fit loosely and draped from the shoulders all the way to the waist. Obviously no bra and she could not bend over without showing all her ass and her tits. Clarice was wearing a yellow cocktail dress that hit about the knees by was gathered to just below her pussy. It had no back and a low V cut showing plenty of cleavage. The guys were wearing jackets with no tie.

"Good to see you Nancy and Clarice." I greeted them. "You are looking really good."

"Thank you Jackie," Nancy said. "And you are looking sexy yourself."

"Your table is ready and Alex will be your server," I said as I lead them to their table.

"Wow," Clarice said when Alex appeared. He was cut.

"Yes, indeed," I said. Alex was helping them in their seats by moving the table to allow them to be seated on each side. I could tell neither girl was wearing underwear of either kind.

"I talked to the other girls and they are coming Friday night and we all plan to come Saturday night to the fashion show and can't wait until the first Swinger Saturday."

"I will put you in the book. No need to call. You ladies have fun and if you need anything I will be here."

All the reservations were at 7pm and we expected everyone to be gone by 9:30. At 7pm, John and Marilyn arrived. Her makeup was impeccable. No doubt it was professionally applied. John removed her wrapped and she was stunning. She wore a flesh colored Midi See Through Mesh Bodycon dress with no bra and a G String with what looked like diamonds on the string at the top of her pussy. Her breasts were perfect with no sag and very full. The areola was silver dollar size and clearly visible. Her nipples were already hard from the excitement of being shown. No doubt she is an exhibitionist and I had to admit she was both beautiful and extremely sexy. John was wearing a business suit and tie.

"Oh Jackie, we are so glad to see you," Marilyn said as she again kissed both my cheeks.

"And you to," I said honestly. "You look beautiful."

"So do you. I love that dress. John can Jackie sit with us?" Marilyn gushed as she rubbed her ample tits on his arms. "Of please sit with us. It will be so much fun."

"I am waiting for my date and if it is alright with John and him, I would love to," I said and I really did want to see what this girl was going to do.

"It is fine with me," John said. "Who is your date?"

"It is Henry Soprano, the owner of the night club Phantom."

"We know Henry. Oh this is going to be a fabulous evening."

"Let me seat you and I will join you when I am finished seating people. Your server will be Penelope." I showed them to the table and one of bussers helped seat them at a table with two love seats on either side.

At 7:10 all were seated but Henry and one other couple. Henry walked in and smiled when he saw me. He kissed me on the cheek as he said, "You look absolutely stunning. I just hope you are not wearing underwear."

"Now why would I?" I said. "Do you know the owner of the Orlando City Soccer Club, John Knight?"

"Sure I know him and his wife, Marilyn. Why?"

"They want us to sit with them. Is that OK?" I asked. "I will make it worth your while."

"Will honestly, I can hardly wait to see what she is wearing. I know exactly why John joined the club. She is a hand full in all kinds of ways. I will be thinking about how you can make it worth my while. I am sure I can think of something."

"Me too."

I showed Henry to the table. Marilyn jumped you, hugged Henry, and gave him a sloppy fuck me please kiss. Henry had both hands on her ass. Henry then held her at arm length took a look up and down, spun her around 360. "Marilyn, I have always said you are the sexiest women in Orlando but tonight you have out done yourself."

Marilyn acted like she was blushing while saying, "You are so bad. I spent all day getting ready. Thank you so much."

John reached out his hand to shake Henry's hand. "Good to see you. Glad you and Jackie will join us."

"I will join you as soon as the last couple gets here. Should only be a few minutes. Penelope will take your drink orders. I am going to have a glass of white wine. Y'all should try the house cocktail to start. Would love to get your opinion."

I went to wait for the last couple who arrived just as I got to the front. I seated them and joined Henry. In walking by Nancy and Clarice, I noticed that they already had their date's dicks out and hard with their dresses pulled up to their waist.

There was none of the lady's dresses that did not show ample skin and could easily make private parts accessible. This was one sexy dining experience.

When I returned to sit with Henry, Marilyn was talking a stream. Henry and John could barely get in a word. When I sat my legs were completely exposed to the waist and it would take moving 2 inches of material to uncover my pleasure spot. The strips of material covering my breast gapped to show most of both breasts. I could see out of the corner of my eyes Henry was appreciating the view.

When Penelope came back she delivered cocktails for Henry and John and a bottle of white wine. I recognized that it was one of our better wines. She poured for Marilyn and I. Gave us the menus.

"I will come back for your order. This swim suit is one of a collection that the club is selling. Each of the server are wearing one from the collection. If you are interested in anything let me know. I am sure we have your sizes available if you would like to try them on. Be back in a few."

Marilyn looked at the collection catalog saying, "These are really sexy. Do you own any of these Jackie?"

I pointed at the red cross I first purchased at Anna and then the second week that was a bustier bra. "I own these 2 and the one that Penelope is wearing."