Jackie Pt. 05

"What would you like to drink?" Penelope asked.

"I would like a Henrytail," Henry said. All decided to have the same.

Bob was very uptight and Marilyn knew this. She is a chatter box anyway but tried to make him talk, getting John and Henry engaged in a discussion about sport. She also was showing plenty of pussy to whomever wanted to see and Bob was definitely staring.

Penelope came back with our drinks, making sure that the guy saw her perky ass and tits as she bent to deliver the drinks. Henry and John slapped her ass as she left. People were milling around to start the evening as the DJ started playing music and everyone was seated. Nancy and Clarice came by to say, "Hi." When they saw Bob, Nancy sat in his lap while Clarice sat next to him.

"So good you are here," Nancy said as she kissed him on the neck. Clarice was rubbing her tits against him to let him know she was there. It was obvious that they had done business together.

Before Nancy got up she invited us all to their 'room' later, kissed Bob and said, "See you all later when we have on less clothes." Truthfully Nance and Clarice could hardly wear less without being nude.

We continued to talk and have people visit us as we had our first drinks. Henry already had his date nude. She enjoyed being nude.

Penelope came by asking about a second round. I wanted wine and so we got a bottle of white for the three girls while the guys had a gin and tonic. She picked up Henry's date's outfit and hung it on the love seat hanger. Again Henry and John patted her ass. She looked at Bob saying, "Don't you like my ass?"

"I like it very much."

"Then please give me a pat." Bob did and enjoyed it.

Our wine came with the guy's drinks. This time Bob rubbed Penelope's ass as she served. "Thank you, sir," Penelope said to Bob. Bob was loosening up. Henry already had his finger in his date's pussy.

I nuzzled Bob's neck and rubbed his leg trying to get him to connect. He finished half his drink and asked, "Do you want to dance?"

"Sure," I said.

So we went to the dance floor with several other people. Clothes were already being removed. While no one started with much, half the guys were shirtless and I was the only one left with panties on. We danced one dance and at the start of the second dance, I started unbuttoning Bob's pajama shirt. I took both his hands and put them on my ass cheeks. Bob soon found the string ties that held the panties on and had them removed. He was kneading my ample ass and I slowly moved my hand into his pajama bottoms. I easily unsnapped his bottoms and he let them slide off. Penelope came out of no where and picked up our clothes and removed my top. Before she left she kissed Bob and let him feel her up. We returned to our dance nude. So was everyone else on the dance floor. We danced like this for 2 more dances. "Time for a drink," Bob said and kissed me long and hard as he fingered my now wet pussy.

We went back to the table; Henry was fucking his date for all she was worth in a missionary position on the love seat. John and Marilyn were watching as they masturbated each other. Bob finished his drink with his finger playing with my clit and I drank my glass of wine. After we finished I straddled Bob, inserted his hard penis in my pussy. I did a slow move back and forth. I was having steady orgasms. I heard Henry make a primal like sound as he planted his sperm in his playboy model.

Bob was close to having an orgasm so I picked up my rhythm and squeezed a little tighter. "Can I cum in you?" Bob asked?

"Yes, please do." Bob had a massive orgasm. He overflowed my pussy and it spread all over the both of us. When he finished I wrapped my arms around his neck with his face between my breast. We stayed there for some time. When I released him he was crying. Penelope was there with a wet towel and cleaned both of us.

"Thank you Penelope," I said. Bob patted her ass.

"Drinks?" Penelope asked. We ordered another bottle of wine and the guys ordered another drink.

"Did you enjoy it?" I whispered to Bob.

"Yes, thank you."

As Penelope came back with our drinks up came Beth, and Gloria wearing nothing leading their boy toys with them. They greeted all of us. "Just wanted to see what was going on," Beth said. "Looks like you guys are having fun."

"It looks like you are enjoying yourselves also," Henry said. He reached around Beth's waist and pulled her pussy to his face. She did not object.

Gloria sat in Bob's lap saying, "So good to see you here Bob. I think the next time we hire your firm this will be the way we do it."

"I agree," Bob said. He was getting into this.

I saw that Bob was getting hard again. If Gloria did not watch out she would be impaled by Bob. Gloria's big tits were in Bob's face. I think she wanted him to screw her. She curled her finger to her boy toy and pointed at her pussy. He took his finger and inserted it in her pussy while kissing Bob. Bob was now getting very hard. Bob looked over at me and said, "Is it OK?"

"Go for it big boy," I said. Gloria slid off Bob's lap and started sucking his dick while her boy toy fingering her pussy. We all just watched this. When Bob was very hard, Gloria straddled Bob, put her tits on either side of his face and started fucking him. She pointed for her boy toy to enter her ass. He took lube that was sitting on the table, slicked up her ass hole, and easily slipped his dick in her ass.

I moved over to Henry. Henry sat me on the love seat next to Beth and started sucking my pussy as he played with Beth's. Beth motioned her boy toy to come over so she could suck his penis while Henry serviced both of us. John and Marilyn watched while playing with each other. Beth's boy toy kneaded my tits while Henry sucked my pussy.

Gloria had changed position where Bob was still seated and she faced away from him with his dick in her ass. Her boy toy was now pounding away at her pussy.

Henry knelt between my legs and entered me as Beth's boy toy did the same to her. Both men were pounding away at us. I reached over to play with Beth's soft tits. She was short but very curvy.

I could hear Bob have his second orgasm of the night as he came in Gloria's ass. She kept him in her ass while her boy toy was reaching his orgasm.

Henry came with a final push into my very wet pussy. This was the second load of the night. As he finished, he stayed there until Beth's guy finished.

Gloria slid off Bob to sit by him. She kissed him as he fondled her tits.

"Jackie, I hope that was OK with you," Gloria said. "We have all known Bob as a good businessman for some time and I wanted to be the first in our group to do him."

"No problem as long as Bob enjoyed it," I said.

Gloria looked at Bob hoping for an answer. "I absolutely did."

"We need to get back to our group," Beth said to Gloria. "We sure enjoyed the hospitality."

"I guess I need to go find out who is fucking my date," said Henry.

I moved to be next to Bob and snuggled in his arms.

"Let me clean you guys?" Penelope said. She took her wet towels and wiped both Bob and I. She then pored us more wine. "You guys want a refill on drinks?"

"Sure," both guys said.

"Jackie, you remember you owe us a treat?" Marilyn said.

"I do remember, let's have another drink and I will be ready to pay off." I explained to Bob that I promised Marilyn I would get spanked and Bob would take my anal cherry.

"Well, I am afraid I don't have another hard on for the night but I want to see this," Bob said.

We finished our drinks before I said, "I am ready."

"Jackie lay in John's lap with your ass in the air," Marilyn instructed. John penis was already hard as he had waited while the rest of us fucked. I laid on John's lap with my naked ass sticking in the air. "John, give her 4 whacks," Marilyn instructed John slapped my ass four time, 2 on each cheek. Marilyn then stood over me and gave me 4 whacks.

"Bob you turn 2 per ass cheek," Marilyn commanded. Bob stood over me and gave me 4 whacks. Marilyn knelt and sucked Bob dick while he was whacking me. Bob was starting to get hard and as usual this treatment was making me hot again. Marilyn said, "Bob, lick Jackie's pussy. John rub her red ass." Bob and John both worked on my red ass and pussy while Marilyn sucked on Bob dick trying to get him hard. She liked a challenge.

"John, give her 4 more whacks." John again smacked both cheeks twice. Marilyn then gave me 4 whacks. "Bob now you give her 4 more whacks." My ass was beginning to burn. "John take some of this lube and rub it on her ass and in her asshole while Bob sucks her pussy." I was now burning so the lube felt good. I was very relaxed so John easily got 3 fingers in my butt hole while Bob manipulated my pussy.

"What about me?" Henry said.

"Henry, you can give her 4 whacks," Marilyn said. Henry gave me 4 hard swats. "Ok Jackie, time for your cherry to be broken. Kneel on the floor with your torso on the bench. Bob spread her ass cheeks. John get positioned behind her to enter and I will guide you." We all did as instructed. I was ready for this. Marilyn took John's penis in her hand and guided him to my loosened ass hole. She first let him entered where the tip just past the sphincter. "Jackie, how does that feel?" Marilyn asked me.

"It feels good."

Marilyn reached under me and found my engorged clit and manipulated it until I had an orgasm. She pushed John forward until I could feel his balls against my ass. "John, let her get used to it then have your way," Marilyn said to John. "I am going to let Bob fuck me. Don't you want your lovely wife get fucked by Bob?"

"Yes I do," John said.

"What about me?" Henry said.

"John, I am going to let Bob have his way with my ass while Henry fucks your wife's pussy. What do you think of that?"

"I think I love my slut wife. I want to see her taken by both my friends at once."

This was turning me on so I said, "John, fuck my ass hard, I want it to be hard now." John picked up his pace but I could feel he wanted to wait until Marilyn was impaled in both holes.

Marilyn had Henry sit on the bench next to me, while she faced him and slipped his dick in her pussy. Once Henry was in she said to Bob, "Bob put lube in my pretty little butt hole and stick your dick in."

John was hardly moving while watching these two men take his beautiful wife. Once both men were in Marilyn said, "Can you see how these men are abusing your wife? Does it turn you on?"

"Yes baby it turns me on."

"Bob fuck me harder. I want to hear your ball smack me hard," Marilyn continued to direct. I could hear Bob pick up the tempo banging her ass. As he did, John started picking up the pace. I had one hand inserted in my vagina, manipulating myself to have one orgasm after another. As my ass muscles got more active I began to notice that the orgasm became more intense.

"John, slap Jackie ass while you pound her. She likes to be spanked." I started to object because it was hurting. But then she was right, it intensified my orgasms. "Bob fuck my ass harder and slap my butt," Marilyn instructed.

I looked over and Penelope had removed her skimpy panties and had her hand in her pussy getting herself off. "Marilyn, have Bob take care of Penelope," I said. "She needs to be rewarded for her service."

"Bob, fuck our sweet server." Bob pulled out of Marilyn's ass. Penelope grabbed Bob's dick and slipped him into her tight young pussy. Marilyn lifted off Henry and knelt beside me and had Henry enter her ass. "Henry, slam my ass hard." Marilyn looked over at me, smiled and whispered, "Isn't this fun?"

I whispered back, "It certainly is." John was the first to come. He overflowed my tight ass hole. Then came Henry while John and I watched.

"Baby, do you see this bad man is filling your wife's sweet little ass hole with his jism?"

"Yes, baby, I see he is tearing your butt up. You are such a slut to have him do that to you."

When they finished, we watched Penelope and Bob finish. She was obviously enjoying being fucked by this man who could be her father. And Bob was loving getting to fuck this young girl. Then Bob had his third orgasm of the night. He kissed Penelope saying, "Thank you, young lady."

"The pleasure was all mine," Penelope said. "I love being of service." She grabbed wet towels and wiped us all clean including herself. She put on her panties then helped us redress in our pajamas. "Do you guys want a night cap?"

We all said that we had enough to drink. "I will bring you all some water. I am sure that work out made you thirsty." Bob smacked her on the ass as she left, Penelope looked back and smiled and winked at Bob.

Tiffany came by with her 'date'. It was the first time I had seen her that night. She was wearing a black leather bustier, leather boy pants, and thigh high boots. Her 'date' had on a cloth sleeve over his genitals with a band around the base of his penis and balls making it all stick out more than ordinary. Attached was a leash that Tiffany was holding, leading him around. This was one of the first executives that joined and he portrayed himself as a tough guy.

"This is my slave Johnnie," Tiffany said. "Don't look at them, they are too beautiful for you to see unless you do something good." Johnnie averted his eyes. "I came by a couple of times and you were involved. Looked like everyone was having fun?"

"We had a blast," Marilyn said. "Looks like you have also."

"It is always fun to train a new slave. Johnnie just needs to be pulled every once in a while to show him who is the master." Tiffany gave a small pull on his leach which tighten around his balls. Johnnie winched.

"Jackie, it looks like we have something in common," Tiffany started. We did not want to advertise that Tiffany was my daughter even though I am sure most people could figure it out. "You like to be paddled and I like to paddle. Maybe we should hook up sometime?"

"Hey, that is my job," Marilyn enjoined. We all giggled but it put thoughts in our heads.

"Say good night Johnnie by kissing everyone's hand but don't you dare look at them." Johnnie kissed both male and female hands. "Good night all."

It was now almost midnight and everyone was fucked out, even the competitive executives. Henry's date did come back and we spent a little time recuperating and talking about the evening.

I walked Bob to the door, he kissed me for a long time, then said, "Thank you. You were right. I think this will make it easier for me to take care of Virginia knowing that I have the club as an outlet."

"Good. There is an escort service that you may want to use, TifEarly Escorts. You need to be careful not to get attached."

"I will but I think Nancy's group would be safe for me also."

With that we said good night. Marilyn and John came and gave me a collective hug saying, "Let's do this again."

I rubbed my still red ass and said, "Next time not so many licks."

Henry walked up and said, "Next time twice as many licks. That pretty ass of yours looks so inviting." He kissed me and Marilyn as he left.

With all the guests gone Edward, Shannon and I thanked the staff. The server had looked at the tips and they were extremely happy. Penelope and Alex, I found out later when the billing came out had killed it. Edward did not look good. I knew something was wrong but wanted to wait for him to tell us.

We all went home. I spent Sunday and Monday with Francis and Tiffany. Tiffany and I again said we had to tell Francis what we were doing but decided to put it off.