Jackie Pt. 05

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

Edited by DRGRIFFIN.

I go see Bob and Virginia

As we walked up to the club for our morning swim were Clarice, Nancy and Beth wearing beach covers. In the locker room Nancy and Clarice could not wait to show off their new bikinis. They were hot women. Last night was no mirage, when these girls decided to show off and what made them sexier was the confidence they had in themselves. They both had on modest bikinis that covered their assets but were sexy. Beth had on a one-piece conservative probably expensive suit. I was wearing the bustier bra suit that looked like a lot of suit in comparison. Shannon had on her see though micro string bikini which was the real winner.

"Well ladies I think Beth and I are the clear losers," I said. "We will make a come back though, won't we Beth?"

"You better believe it. This is round one," Beth answered. "Did you buy those last night at dinner?"

"Yes we did," Nancy said. "You should go. We had a blast last night

As we walked to the indoor pool, 4 of the early gym guys met us, dropped their jaw and did cat calls. Nancy and Clarice ate this up and wanted more.

We did laps for 30 minutes and as we exited the pool, two of the guys were waiting with towels. They were in business suits and obviously going to be late for work. "We just had to see this again and wet y'all are more memorable."

"Take a good look fellows and eat your heart out," Clarice said. "Better yet think about it all day."

"We will be late but it was worth the wait. We are going to see what it looks like walking away."

We walked away and glanced behind us. Nancy threw them a kiss as we entered the locker room.

In the shower, Clarice started bragging about making her server cum the night before. She glowed with the remembrance.

Shannon followed me to my office while I filled her in on the evening's festivities. She was very pleased. Edward knocked on the door and wanted to know the same thing. He finally said, "Let's make sure to get the survey out this morning, and the updated schedule. Do we still think we will be ready for the Pajama Party?"

"Absolutely," Shannon said. "I think I am going to need an assistant however. Jackie has filled me on last night's activity and has agreed to manage this coming Saturday night but there are just too many nighttime events."

"Yes, I agree," Edward said. "You two are going to burn yourselves out and that is the last thing I want. Shannon, you lead the effort to find your assistant. I took a quick look at the take last night and it was very impressive. At this rate we will be cash flow positive within a month and my investment will be mostly paid back. Jackie thanks for helping Shannon out. What are the counts now?"

"We have 65 primary members and 37 associates. I have 5 more scheduled for today. It looks like we will likely be at 75 primaries by the end of the week."

"Outstanding girls. Thank you so much for the effort," Edward said.

When Edward left Shannon asked, "Does Edward seem off to you?"

"Now that you mention it, yes. He seems to have lost interest in how we dress and has gotten to be all business. More than that he seems to have lost energy."

"Exactly, I am wondering if he is sick," speculated Shannon.

"No, I don't think so. I think there is just so much to do he wants to focus on the work. And honestly we have done pretty well so far. This thing is working."

"It is working and I am having a ball. I am glad to get a little help however," said Shannon.

"I am ready for a Monday off. So you are going to do Friday night and I am going to do Saturday, both off Sunday. I may take Monday off and spend it with my Grand Kids."

Marilyn came by the office a little after 1pm. "Hi, girl friend. Want to talk now?"

"Absolutely, what are you doing today?" I asked. She was wearing a tennis outfit so I thought I knew.

"I have a tennis lesson with Bruce at 2pm," Marilyn said smiling.

"I bet. I know that will be fun. He is easy on the eye isn't he?"

"I had not noticed," she said laughing. "I am dying to hear what you want to discuss."

So I spent some time telling her the situation with Bob and how I had lost my husband.

After my monologue Marilyn said, "I think you have it all correct. John and I do know Bob and Virginia. They are straight as can be and about as good people as you can find. Bob does need this. We can help him and you are the right one to go see his wife. His wife is doing a selfless thing and we need to help her. How can I help you?"

"Well I am going to convince Bob to come to the pajama party with me. I feel like if he has a good time at that first event he will take the initiative on his own afterwards. I also plan to go see Virginia on occasion."

"Would you like for me to go with you?"

"I want to go alone the first time since I don't know her but after that let's talk."

"Ok, good plan and I will bring John up to speed. He can help with Bob. What else?"

"You really enjoy anal don't you?"

"I do now but it did not start that way. I wanted to do it because I thought John would enjoy it and he does. I had someone help me to start with. Want me to show you?"

"Would you?"

"Sweetie it would be my pleasure. Want me to start now?"

"Why not?"

"Do you have some hand lotion?"

"Sure do."

"I used butter for the first time last night and that really worked well. But you need some kind of lube."

"That was the best butter money can buy," I informed her.

"Worth every penny. Make sure my table has a few extra pats from now on. Take your panties off, and bend over your desk."

"I rarely wear panties," I said as I bent over the desk.

"First thing is make sure you are clean. If I know that anal is on the agenda, I do an enema. The premixed ones from the drug store work fine. Second thing is use plenty of lube. If you can get an anal lube that is best. But almost anything slick will work. I am going to stick one finger in with a no lotion. Girl you have one of the prettiest big asses I have seen. Men must love it."

She inserts her index finger. She left it there for a short period of time. "How did that feel?"

"It hurt."

"Yes, I am sure it did and my finger is no where the size of a penis. The key to this is to relax everything from the waist down. Is there any thing that is guaranteed to make you wet?"

"Getting paddled. There is a paddle over there if you want to use it."

"Girl, you are full of surprises." Marilyn got the paddle and asked, "How many?"

"Three per cheek should do it." Marilyn rubbed my ass and put lotion on my ass cheeks and pussy. First lick on the right cheek, then the left, then 2 more times each cheek. She checked my pussy and said, "Girl friend you are wet as you can be. Let me work on that pussy a little. While I do that concentrate of relaxing like just before a bile movement."

She knelt down and tongued my clit and rubbed my ass at the same time. I climaxed once and felt like I was relaxed. "Now let me put a finger in but don't think about that. I am going to use lots of lotion with the finger. Think about the orgasm you just had." She put the finger in and asked, "Does that hurt as much?"

"No."

"You are more relaxed but not the way you need to be to enjoy it. I am going to leave my finger in and I want you to alternate between pushing up and in. I did and I was beginning to get the feeling of relaxing my anus. She took her finger out, put more lotion on my ass hole and pushed 2 fingers in much easier than before. "Notice that went in much easier and that is with 2 fingers. You have more lube but mostly more relaxed. Tighten and loosen your sphincter a couple more times." I did as she took more lotion and shoved 3 fingers in and started to manipulate my clit with the other hand and I had a big orgasm. "See, that is all there is to it."

"You are a great teacher. We should give classes. That last orgasm was more intense because of the pressure in my ass."

"Exactly. Now home work. Get a small anal plug, some anal lube and masturbate with the plug in and focus on relaxing and the exercise I showed you. You will be an anal maniac by the Pajama Party."

"I think you are right."

"I need to run. That made me hot and Bruce may be ready to help me out. You owe me. Maybe paddling you and having John take your anal cherry as payment."

"Sounds fair. Let sit together at the Pajama Party and I will pay off. I am sure Bruce will take care of you but if not I will."

"Thanks for off but got to run." She left as I was wiping myself off.

The rest of the week was spent signing up new members. By Friday afternoon I had 82 primary members and 49 associates. There were 29 couples signed for Friday night dining and 33 signed up for Saturday night dining and lingerie modeling.

Saturday night Flexible Clothing Dining and Lingerie Modeling

On Saturday, I went to see Bob and Virginia. Virginia was in very bad shape. It brought back a lot of bad memories. She was barely strong enough to sit in a chair. She was very thin, pale, no hair, and obviously in pain. She, however, had on make up and a very nice dressing gown. My heart broke that she had made such an effort for me a stranger.

Bob answered the door saying, "Good to see you Jackie."

I hugged Bob and said, "And you too."

Virginia was waiting for me in a sitting room. The house was huge and beautiful. You could see Virginia's hand in every piece of furniture and picture. Bob was 55, balding black hair, small but still in good shape. He owned and still ran his construction firm.

"I am so glad to have you come by and see me," Virginia said. "Did Bob offer you anything to eat or drink?"

"I am fine thank you."

"Bob told me about your experience with your husband's cancer. It helps so much to have people who will share their experience."

We spent some time discussing how cancer affects people's lives. Then we got around to discussing the club. Virginia had several questions about how the club operated. I answered until I thought she fully understood what the club was about. I asked, "What is your honest opinion about the club and Bob membership in the club?" I could see Bob squirm.

"Bob and I have never considered anything like this. Our relationship has been very traditional with 2 grown children, that have been a delight. However, I am dying and have been for some time. Who knows how long I will be here and I am ready for the end. Bob has been terrific to me for 30 years but particularly in the last couple when I needed him. I just hate that he has sacrificed so much for me. He has sacrificed business and personal life. I want to still be Bob's wife when I die. But I want Bob to have a normal life as much as possible and sex is a part of life. So I want Bob to try this but not become involved with anyone until I pass. I trust that Bob will stay loyal to me no matter what he does. Does that answer?"

I was crying too much to answer for a minute. Bob handed me a Kleenex. After I composed myself I said, "That is one of the most insightful, thoughtful and loving answers you could give. I would like your permission to take Bob to next Saturday night's Pajama Party under exactly the parameter you described. When Bob told me the situation, my thought was he would benefit from the club. So if Bob goes with me and decides he can not get the benefit I think from it, we will refund his money with no hard feelings. Can I have your permission?"

"You have my permission, if Bob will do it. I have encouraged him but maybe he just needs someone like you to pull him. I appreciate you asking."

"Bob, will you go with me next Saturday night?"

Bob looked at Virginia, she slightly nodded and said, "Yes."

"Good," I said. "Virginia I would like to come see you periodically. Is that OK?"

"I would like that. But I get so tired."

"I know there will be times you are asleep but it helped my husband to have people there even if nothing was said. It is funny but we found our real friends the sicker he got. I want to be your friend."

"Thank you."

"I know you are tired and I will leave now but I will be back," I said as I kissed her forehead.

Bob walked me to the door and asked, "Can I buy you something for the event?"

"If there is something in particular, sure, but the club gives me a clothing allowance for things like this. So just up to you. Just meet me at the club at 8pm next Saturday. To make it clear, I have no desire for any other relationship other than to be friends with you and Virginia. She is a very impressive lady. I wish I had known her before."

"Ok will see you next Saturday and thank you Jackie." I hugged Bob again with tears in my eyes. But I was happy. I thought the club could do some good here.

Saturday night I supervised the Flexible Dress Dining and lingerie modeling night. This time I did only supervised and did not participate. It was a roaring success with a lots of lingerie purchased, as well as a lot of alcohol. I did pick out my outfit for the Pajama Party if Bob did not send something.

All 5 of the lady executive were there; Nancy, Clarice, Beth, Lizzie, and Gloria. They were dressed to impress and wanted my opinion who dressed the sexiest. These girls were competitive. Beth was the youngest, 35, and one of those short about 5 feet tall very stacked girls who looked great if she could keep the weight off. Big breast and ass, stumpy legs, and a little paunch at the stomach. Lizzie was 41, short, 5 feet, maybe weighed 100 pounds with a boyish figure. Gloria was Hispanic, 48, 5 feet 10 inches tall and big all over but not fat. They were all nude before salads and stayed that way until the end of the dinner. They swapped partners at least once and I was convinced left with different guys than they came in with. Their dates were young hunks and interchangeable. These girls could party and all planned to be at the Pajama Party.

Tiffany could not make it but she did send 4 girls and 4 guys. They modeled through out the night, with the outfits getting more and more brief. The last round had all the girls in crotchless panties and shelf bra or hole cut for the mammilla or translucent and the guys in variously designed socks covering their penis only. They distributed business cards and I would be surprised if they did not get work for the Pajama Party.

I spent Sunday and Monday with the grand kids. Tiffany and I did discuss telling Francis what we were up to but decided to procrastinated.

The Girls decide to compete for sexiest swim suit

When Shannon and I arrived to swim all 5 of the Lady Executive were there. Nancy, Clarice and Beth were wearing their purchases from Anna's. This was Lizzie's and Gloria's first trip to the lap pool with the girl and hence wore a standard one-piece conservative swim suit. Nancy, Clarice and Beth were all three in very stylish bikinis that were very sexy but could be more revealing. You could tell Lizzie and Gloria were envious of the other girls.

I heard Lizzie whisper to Gloria, "We are going to have to pick up our game."

"Yes we are," Gloria whispered back. "Let's go shopping after work."

"Done."

After the swim, there was a group of men hanging around the locker room, obviously wanting to see what the ladies were wearing. Nancy, Clarice and Beth strutted and got lots of attention. Lizzie and Gloria looked jealous again. No one said anything but no one had to.

On Friday, Lizzie and Gloria were now wearing swim suit about the same of the other 3. "You 3 aren't the only one that can dress in sexy swim suit," Lizzie said. "The guys are going to pay attention to us today."

"We will see," Nancy said.

This was all good natured competing among the ladies. We did our laps and on the way back again there was a group of men waiting to see the parade. All 5 girls walked by with a purpose. And the guys were obviously interested.

In the shower Nancy said, "We need to find out who looks the sexiest in their swim suit."

"Let Jackie and Shannon decide," Gloria said. All 5 looked at us for the answer. I looked at Shannon and we both knew that we could not answer.

"I think the guys need to answer this question," I said. "Shannon and I will ask the gawkers guys next week who wins and we will tally and announce the winner."

"What does the winner win?" asked Beth.

"The winner gets to name a dare for the others," Clarice suggested.

"Done," they all said.

The Pajama Party

Bob had a night gown delivered for me to wear to the party from Neiman's. It wasVintage Powder Baby Doll with black lace over the top and a scalloped plunging neckline. The powder was a mesh that was somewhat see through. The panties were old style powder bikini cuts with ties on the side. There was a note from Virginia that said, "Show Bob a good time but send him back to me. Thank you."

Shannon and I were there all Saturday afternoon getting the room ready for the night. There were 45 couples coming. We gave them the opportunity to say who they wanted to share a table with. The way we were arranging the room was to use the love seats arranged around a large round coffee table with movable screens so it was like rooms. Except they were not closed off so you could see what is going on around you. We also had a dance floor set up and a DJ.

Around 6pm Edward arrived, so Shannon and I could get something to eat, take a shower and get dressed. Tyler had invited Shannon. She was dressed to kill. She dressed in a red teddy that snaps at the crotch, showed much of her ass and barely covered her breasts. We went back up early enough to make sure everything was ready. We met with the servers, 4 males and 4 females. We assigned the servers to each table.

"Alex, want to take on Nancy and her entourage?" I asked Alex.

"I would love to. Those ladies are fun and a challenge."

"I think you need to be prepared for what comes. They are competitive."

"I am ready." Alex said. He was wearing a sock with strings that tied. "See," he said as he untied the string and the sock came off easily.

I assigned Penelope to us as she knew Marilyn, John and I. All the servers were in very sexy lingerie. We were ready.

Henry arrived with a stunning drop dead young blonde that could have been a playboy model. She was dressed in a sexy baby doll with a thong for panties. I greeted them and seated them in our room. The 5 women executive arrived, all with young studs. I recognized the ones with Nance and Lizzie as being Tiffany's escorts. Tiffany arrived with one of our members and I seated them in one of the unassigned rooms. I whispered to Tiffany, "Have fun, I am."

She whispered back, "Always."

Then Bob arrived. He was dressed in silk black and powder pajamas that matched my outfit. I hugged him, "So good to see you. Let's have fun tonight."

"You look beautiful."

"Thank you, Bob."

John and Marilyn arrived at the same time. Marilyn removed her wrap and revealed a very revealing see though mesh gown that clung to her body. The material showed her brown areola clearly and already hard nipples. She was wearing a crotchless string thong that pushed her pussy lips together and clearly visible through the dress. I escorted John and Marilyn and Bob to our room. I now let Edward take over the hosting duties. Penelope followed us to our table. She was wearing a thin bra that left the top half of her perky B cups exposed. She wore a pair of crotchless panties that showed her pussy. Her pussy was waxed except for two strips that were dyed pink shaped like small bunny ears above her clit hood. It was very alluring. I knew she was going to be fucked by someone. This was allowed as long as the guest initiated the episode.