Jackie Pt 06

This story is being written by Jackie as a narrative of her progression from sexually inactive, to widower, to sexual active, to millionaire. Some of the primary characters are older so you may not like stories about older people.

Edited by DRGRIFFIN.

The 5 female executives compete for sexiest swim suit

Monday I went in to swim but spent the rest of the day with Francis and Teddy. This was the first day of voting for the sexiest swimsuit by the executives. Shannon and I dialed our suits back to being regular bikinis. We did not want to interfere. The five ladies were now all in very nice bikinis. The suits were all cut in normal cut bikini style. I thought Gloria, the amazon Latino lady and Beth the short overly endowed girl were the ones that showed best with these cuts. They had more to show so even with modest suits they stood out.

Even though we had not advertised this competition, there were more gawkers. Today 10 guys stood around. And the vote had Gloria first and Beth second. We decided not to tell anyone but I think word was spreading.

On Wednesday, the game began to turn. Nancy and Clarice knew they were behind Beth and Lizzie, so they came wearing string bikinis. These still cover all the naughty bits but revealed more skin. The tops were triangles of material that rode below the breast and ended where the breasts started, leaving all the cleavage exposed. The cut of the bikini covered their pussies but ended about 3 inches above the slit. It was connected to the back with strings which left about half of each cheek exposed. Lizzie, Beth and Gloria noticed and I think knew what was going to happen.

This time there were 15 guys waiting to observe and vote. This time Nancy was first and Clarice was second. I did not think Lizzie had a chance. She was very small and at most a small B cup and a boyish butt. With the tally combined Gloria was still first but Nancy had moved to second and Clarice and Beth tied but still with a chance. I thought it would be very interesting to see what happened Friday. The rule was that they could not be completely uncovered either top or bottom. They also had to come Friday night and model their selections at Friday night dinner where the winner would be announced.

Friday, the girls pulled out all the stops. Nancy wore a micro string bikini. It was made of yellow glowing string less than ¼ inches wide. The top was one string around the neck that expanded to three strings at the top of the breast and joined the string around her torso beneath her breast. Two string were on either side of each breast and the center string pressed on the nipple but did not cover the areola. It caused her C cup to mound on either side. The bottom had a string just above her slit with 3 stings leading under her pussy and merged to one string that fit in the crease of her ass. The two strings along the sides of her pussy pressed in causing the pussy lips to mound in the middle and the center string pressed into the slit causing the lips to mound to the side. The result was to show her bald pussy lips as puckers on either side of the slit.

Clarice wore a similar suit except it had 2 instead of 3 string. This showed all her areola and her pussy lips to hang down in the middle. She had dangly pussy lips anyway which hung down at least an inch.

Beth had a bikini of flesh colored transparent materials similar to the one Shannon wore. It hardly hid anything. She also had her black pussy hair waxed with the exception of short clipped pussy hair above the slit in the shape of Hitler mustache and dyed purple. It stood out.

Gloria the amazon wore a monokini made with string that wrapped around her neck, extended between her legs and tied around her waist. The string was completely impaled in her ass cheeks so from behind she looked naked. There was small tear drop shaped material over each nipple that did not completely cover her areola and over her pussy lips which did not come close to containing this large women's twat. It was very thin material and extremely sexy.

Lizzie had gone all out. She wore a sling monokini that was only string. She was small B cup but she had large puffy pinkish red areola. The string hit and cut the areola in half. The string went between her legs and impaled between her pussy lips and ass crease. The string pushed the pussy lips to the side and caused two mounds of flesh. She had her pussy adorned with piercings. She had a Horizontal Clitoral Hood Piercing with a diamond studded ring in the opening. There were also 2 Outer Labia piercings along each side of her pussy with the same rings. The piercings were at the top and bottom of the Labia leaving the middle inviting to a dick. She had both nipples pierced and bars in the opening. These were obviously long standing piercings.

I thought now it was a toss up. We all swim our 30 minutes of laps. When we came out of the water 16 guys and 3 women were waiting. This time the girls were not satisfied with just a parade. Each decided to work the crowd. They each picked someone to dry them off. They kissed and encouraged guys and gals to feel the merchandise. It was clear they were all excited. Before I knew it they were giving blow jobs. We had a rule that they had to keep their suits on but neglected to think about this. Each girl had laid a towel down and unzipped the fly of men mostly dressed for work in suit and ties. The guys and girls were lining up for their favorite girl. The 3 women were raising their business skirts and each was sucked and fingered to a quick orgasm before they left for work. It was a scene.

Shannon and I managed to get all 19 votes in this chaos. When all were serviced, voted and left, the girls were giggling and all agreed it happily got out of hand. They were also very excited about exhibiting their purchases at the dinner that night and finding out the winner. There was much talk about who won and what the challenge would be. Shannon and I instructed them that they would model each of their 3 outfits in the order they wore them for 30 minutes each. Anna had descriptions and price on a glossy for each. Anna was going to make money off this. We wished the girls good luck as they left.

When Shannon and I tallied the vote. Gloria, the amazon, won but just barely. Lizzie had made a come back and the difference between winner and losers was 4 votes.

Edward admits to a problem

That Friday afternoon Edward called Shannon and I into his office. Edward said, "Monday the FDA will announce approval of the medication developed by Solvent Pharmaceutical. I am going to sell all my shares and buy a small chip company that I believe is up for sell. It is LUV Technology, symbol LUVT." He talked a little longer before seeing Shannon and I. "Come on in girls." He hung up after saying good bye.

"I have some bad news girls. I think you probably wondered why I have changed in the last few weeks."

"We thought you did not like us anymore," said Shannon.

"No, I love both of you now more than ever. You have made this dream of mine a reality. I can never repay you. I have a medical problem. I am now 68 years old and have developed a circulatory problem that can not be cured. As a result of the medication, I can not get it up anymore and am tired and weak a lot. I will probably live for some time but I am going to have to cut back my schedule. I can work for a couple of hours in the morning but that is it. And I am not sure how long that will last."

Shannon and I were both crying, so Edward stopped to let us get control of ourselves. After a little I managed, "What can we do to help?" I asked.

"I want to make Jackie the assistant GM. Shannon you are too critical as the event manager and Jackie is almost done recruiting. What are the counts now Jackie?"

"We have 85 members and 52 associates."

"So in about a month we will have the membership complete. I think we were right with the need to limit to 100 members. Besides we make a boat load of money at that level. In effect, we three will manage the club. I want to change your agreement that will give you both 25% of the business in a year. Girls don't feel sorry for me. I have had a great run and have time to manage the end the way I want. My only regret is that I did not get to swing with you both. But how can I complain. I have had it all."

Shannon and I looked at each other not knowing what to say. Finally, I said, "We owe you so much. We will make this, your last vision a success, we promise. And we will make sure you are cared for."

"I have not doubt but I have people who will take care of me physically but your love only you can do."

"You have that forever," Shannon said. "Can you give us one last spanking or would that tax you too much?"

Edward laughed and said, "My doctor would probably not approve but I think I can manage one last paddling."

Shannon got the paddle and handed it to Edward, pulled up her skirt, bent over extending her naked hard ass to Edward. Edward gave her 6 licks with the paddle. As he finished he rubbed her tush, fondled her clit and said, "That is one beautiful ass that will make many men crazy for it. I wish I had gotten to fuck it."

I was crying again but managed to bend over, raise my skirt, and bare my big broad naked ass to Edward. He gave me 6 licks, rubbed my red ass and fondled my clit. He said, "That beautiful ass was the last one I fucked and the last was the best."

We hugged Edward and left crying. Shannon and I went to the bar for a stiff drink.

The 5 executives model suits and winner is announced

Shannon acted as hostess while I managed the 5 executives and servers. We had only 19 couples tonight and I think they were in for a treat. We had 4 servers tonight 2 males and 2 females modeling tennis outfits. The tennis outfits were not as sexy as the swim suits, i.e. not as revealing.

After everyone was settled and first drinks served, I explained what was happening tonight. After that I said, "First we have Nancy modeling a nice yellow bikini. She will come by each table and give you close up view of the merchandise and a flyer. These models enjoy close up inspection. Let your server know your interest. This week we ran a contest to determine which of our models tonight displayed the sexiest suit or who was the sexiest model. At the end of the evening I will announce the result. The losers will have a task imposed by the winner."

With that I announced each contestant in 5-minute intervals. The first set of bikinis got modest attention and little close inspection but I suspected good purchases. The next round with the string bikinis got more attention and far more close inspections primarily butt rubs and bra adjustments.

The diners were now finishing their main dishes and on to after dinner cocktails. "Now for the last and most revealing round. First we have Nancy in this stunning micro string bikini. Isn't she stunning." This time there was a lot of interest. Nancy was being fondled by each table and enjoying it. This time it was taking quite some time to go from table to table. Each contestant got a combination applause and course hooting.

Lizzie was last to reveal. Her body piercings got a lot of looks and discussion. As she went from table to table the men were certainly interested but the women also asked a lot of questions. I heard, "Does it hurt? Does it make orgasms more intense? Does it make your tits and pussy more sensitive? Does it get infected?" There was a lot of touching the rings in Lizzie's labia and clit hood. Lizzie seemed to enjoy the attention. I could see moisture coming from her pussy. By the time the last table finished there was no doubt the moisture was running down her legs.

When Lizzie was finished everyone was interested in the winner. I held up an envelop saying, "In this envelop we have the winner from the Jackie and Shannon counting firm. And the winner is Gloria." Everyone applauded and whistled while Gloria hopped around like a runner making a touchdown. Nancy looked pissed and the other girls clearly did not like to lose. But to their credit they surrounded Gloria and hugged and congratulated the beautiful amazon.

"Gloria, do you know the task the girls get to do?" I asked.

"Yes, we are going to invite the group of 19 people who voted for us to a party where we serve and entertain."

"You too?" Nancy asked.

"Absolutely, you girls can't have all the fun. Shannon and Jackie are going to help me plan the activities and they will be a surprise to you."

"That does sound like fun," Nancy said.

Anna sold a lot of the swim suits the girls wore that night.

On the following Monday Shannon and I sold our shares of Solvent Pharmaceuticals for $50k and bought LUVT. In less than a month LUVT was rumored to be a buy out candidate and went from $5 a share to $15. We sold making our portfolio $150k. By the end of the year, we had a portfolio of about $500k each with the help of Edward's tips.

The Biker Bar night

Gloria came by a couple of times to plan the party. We had the names of the 19 people who had voted and wanted to find a night all 24 people could attend. It was hard but we hit on a Thursday night in a couple of weeks. We decided that the night would be 'Biker Bar' night. We wanted to act like 2 biker gangs came together at one biker bar and would compete at various events.

We had a couple of weeks before the event, so we let the participates know the motif and asked them each to dress like a Biker. Gloria decided on micro denim skirts and halter tops for the executives. We advised them to buy well worn micro denim skirts and halter tops. We left it to the 3 females voters to come up with their own version of what a Gang owned Biker Babe would wear. One gang would be called the Black Hearts and the other the Red Hot Gang. Gloria picked the boss of each gang and let them do a school yard pick requiring 4 girls per gang. We asked the girls to dress with black tops for the Black Hearts and Red for the Red Hot Gang. We found body stencils for gang symbols and asked all 24 to place their gang stencil on their necks.

The 5 female executive arrived early and they were hot. The denim skirts were definitely micro not mini. The width of the skirt varied by girl. Beth and Gloria were big butted girls and their micro did not completely cover the crack of their ass top to bottom. Pulled down you could see the start of their ass crack and the little fine hair. Nancy and Clarice, more average sized girls the ass was covered but it barely dropped below the crease. Lizzie was better covered because of her boyish figure. The skirt extended below the pussies but no one wore panties. No one could bend over without showing everything. All skirts were tight. Lizzie had dangling chains in her labia rings. The chains were about 2 inches long and you could see little brass balls at the end of the chains just below the bottom of her shirt. All five chose halters that were at least a size too small. In the case of Gloria and Beth, a lot of tit hung out the side and lot of cleavage showed. The girls were still competing and probably always would.

They all had their body stencil for their biker gang on their necks but these girls had other things stenciled on. I saw the word 'SLUT' a lot with barbed wire stencils. Gloria, Shannon and I went over how the night would go with the girls. Alex was the bartender for night which made Nancy happy. Also Penelope was going to help but we made it clear the 5 lady executive were to serve and entertain the crowd. Shannon had a bachelor party going in another room so I was to be the bar owner and keep the party moving. I borrowed the outfit that Tiffany wore at the Pajama Party, black leather bustier, boy pants, and thigh high boots.

The group started to arrive. All the guys had tight jeans either leather or denim. Most of the guys had no shirt and an old leather vest. The 3 voting girls were dressed this way; one with denim shorts with the ass cut out and halter top, one in an American flag monokini, and one with a bikini. All had the gang stenciled tattoo and their own painted fake tattoos.

The pretend gang separated the room, the Red Hot Gang on the left and the Black Hearts on the right. The girls worked hard to get everyone a drink. In this case since they belonged to the gang they also got themselves a drink. Everyone including the girls were drinking beer, bourbon, or tequila shots. After the group was relaxed I announced the first activity of the night.

"Tonight we have two gangs, the Black Hearts and the Red Hot Gang. The bosses have agreed that instead of fighting tonight they are going to compete in the Biker Bar activities. First up is an opening round pool match among the Biker Babes. The first round will be Lizzie against Mary." Mary was the voter wearing the American Flag Monokini. Neither girl had ever played pool, so only 4 balls were used. With each time they bent over to make a shot their ass and most of their pussies were visible and the crowd reacted. Of course the crowd hooted each time. Lizzie would play with her labia rings and chains at any opportunity. Lizzie somehow made her 2 balls and won. She jumped up and down making her chains even more interesting.

"Lizzie gets to spank Mary because she lost." Mary bent over the pool table with her nice firm ass ready. Lizzie gave her 6 whacks with my paddle. She did make her butt red. Lizzie rubbed her butt before she raised up and gave each cheek a kiss.

"Next up are Sue and Terry." Sue was the voter wearing the denim shorts and Terry had on a bikini. They also had 4 balls and some how Terry won. Terry gave Sue her 6 whacks, and she too gave her ass cheeks some soothing kisses only more than one.

"Ok Terry enough. Now up is Nancy vs Clarice." They had 4 balls each and clearly they had played pool before. Nancy and Clarice cleared their first 3 balls in their first round. Clarice and Nancy both pulled their tight skirts above their hips to bend in the proper position to use the pool queue. Nancy made her ball and won. She too bounced up and down and one of her tits came out of its too small halter. The crowd hooted. Clarice bent over the pool table and Nance gave her 6 hard whacks and her butt was clearly red. Nancy instead of kissing Clarice ass played with her very visible clit. Clarice was moist from the thought of so many people seeing her ass and the paddling. I suspected it turned her own. I let Nancy work on her pussy until I saw Clarice had a small orgasm.

"Ok Nancy, that is good. Now we have Gloria versus Beth." These were both big butt and breasts girls. Their halters barely contained their large orbs. Gloria was a good 8 inches taller. They also had 4 balls and finished quickly. Gloria won. Beth bent over and showed her broad fleshy ass to Gloria. Gloria gave her the 6 whacks and did Nancy one more. Instead of playing with Beth's pussy, she tongued her ass and pussy with a long tongue. Again I let it go until Beth had a small orgasm and a very wet pussy and ass.

The next round pitted the winners of the previous round against on the guys. Lizzie had no chance and she knew it from the start. She concentrated more on showing off her jewelry than making a shot. She happily bent over and her pussy already glistened before the first lick and was wet after her 6 whacks. I wasn't sure that she had not had an orgasm during the paddling. Her opponent licked her pussy until it was clear she had enjoyed it.

Terry also lost and took her 6 whacks and her ass kissing. Then came Nancy against her male opponent. She cleared her 4 balls on her first round. The crowd cheered and Nancy hooped up and down with enthusiasm. "Ok, remove your pants," said Nancy. He had his pants off before I could rule and was bent over waiting for Nancy to give him his 6 whacks. Nancy enjoyed this very much. This guy had a long dick which hung down as he bent over the table. Nancy after the 4th whack gave it a good squeeze which made him hard. After the 6th whack, Nancy kissed his ass and licked his ass hole while gently squeezing his hard dick. I had to stop them.