Jolene Listens Ch. 10

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Jolene must complete some "challenges".
6.6k words
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Part 10 of the 12 part series

Updated 11/02/2022
Created 09/30/2008
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"I'll see your ten, and raise you ten," The man to my right said as he threw in two chips. I was holding three nines, a duce, and a three. I considered whether to fold or risk another twenty dollars. I don't know why I cared, Tom had paid for my chips so it wasn't my money. I guess I just didn't like to lose. Before I decided what to do, my wife Jolene came out of the kitchen with some more beer and chips.

She was wearing a blue halter top that left her stomach bare and outlined her fine tits nicely. The black skirt was just long enough to cover her ass, but allowed a glimpse of her bare pussy when she sat down. On her feet she had on a pair of open toed sandals with four inch heels and straps around her ankles. In other words, slutty hot. And I wasn't the only one who thought so. The other men at the poker party were not shy in voicing similar opinions; of course they didn't know she was my wife, they thought she was a prostitute. A high priced prostitute, but a whore none the less.

"OK, I'm in," I announced as I tossed two chips onto the small pile in the middle of the table. Tom was next and he called, flipping his cards over. He had a full house, queens over tens. That beat my three of a kind and everybody else's hand too.

He chuckled as he raked the chips in. "Like taking candy from a baby."

Tom was ahead of everybody by quite a wide margin, and it was clear he was going to win eventually. I decided that this was a good time to change the character of this party. On the next hand I had a pair of aces and when my turn came and had to put most of my chips in to match the current bet.

"Well, well. Everyone hanging in there eh?" Tom mused. "OK, I'll see that and raise two hundred."

Everybody else folded. If this were just a poker game I would have too. "I'll see that and raise you everything else you've got," I replied.

"With what, you don't have that many chips," Tom challenged.

"I'll use Jolene as my collateral," I answered. "If you win then she's yours to entertain you until morning. That's easily worth the entire pot."

"OK then, I'm all in," he said and pushed all his chips forward. "What have you got?"

I laid down my cards. "A pair of aces."

Tom threw his head back and laughed. Then he melodramatically laid his hand down on top of the big pile of chips. The cards were in order: two of hearts, three of hearts, four of diamonds, five of spades, and six of hearts. A straight. That beat my lousy pair. But then I figured on losing because I knew everybody would win now.

"Come on over here Jo, and sit down," Tom ordered as he slid his chair back from the table.

I had my wife in her "expensive prostitute" mode, so she didn't question his order. She just strutted over to him, looking happy to be doing something other than serving drinks and getting her ass pinched. She sat down on his lap and he immediately pulled her face to his and placed a lip-lock on her. Within a few seconds of starting the kiss he had her top pushed up over her tits and was pulling on her nipples.

One of the guys apparently did not know about Jolene and started looking uncomfortable. "Well, I suppose that's the end of the game," he said and started to get up.

"Sit down," someone else said. "The party has just started. You should know by now that Tom always shares his good fortune."

The first man stopped moving only half way to his feet, a surprised expression on his face. Then he slowly sat back down, his eyes fixed on Tom and Jolene. I looked back in Tom's direction. He had broken the kiss and was now pulling my wife's top off completely.

"She's hot as a pistol, guys. Let's get this table cleared off," Tom declared.

The table was quickly cleared of poker chips and cards. Tom then stood up and lifted Jolene up onto the table. She leaned back on her elbows and lifted her hips up so that Tom could slip her tiny skirt down her shapely legs. He flung it over his shoulder and dove for her glistening snatch, burying his face between her thighs. Jolene threw her head back and let out a loud moan as Tom attacked her shaved muff with his mouth. It was a hot scene and the rest of us just stood around watching my wife toss her head back and forth as Tom pushed all her pleasure buttons.

Then he stopped and looked up at us. "What are you guys just watching for? Get on those tits and someone put a cock in the whore's mouth."

They didn't need to be told twice. The other four men surrounded them and lowered Jolene flat onto her back. Two of them started pulling and sucking on her already hard nipples while another guy tried to get his cock into her mouth. The angle was all wrong though and the best she could manage was to lick the head and pump the shaft with her hand.

It didn't take too much of this before Jolene started shaking and squealing her way through her first orgasm of the evening. Tom managed to keep his mouth on her pussy despite her bucking, slurping up the copious amounts of girl juice that was pouring out of her. When she was finished Tom suggested that they move her to the living room. He has a sofa in there that can be folded flat to make a perfect platform for multiple partner sex.

From here on out it was a six on one gangbang. The first round only lasted about twenty minutes; all the men had cum, including me, and needed a little break to recover. I took the opportunity to get some bottles of water from the kitchen. We would all need some hydration during the second round, which I knew would be much longer. I was right.

All of us men stayed hard much longer this time. Jolene was a total slut though, and took everything we could give her. For the next couple of hours she was continuously being fucked in one or all of her holes. It was incredible. In case you've never seen anything like this I'll explain how it works. There's no way six guys can service one woman at a time; it just gets too crowded and hot with that many people that close together. So we tag-teamed her. Normally there was only two or three on her at a time while the rest of us watched. When one would get tired or cum, someone would take his place. We keep up this rotation until nobody could get it up anymore.

At the end Jolene was still climaxing, so I know she had not hit her limit, if she even has one. Her body was covered in sweat mixed with cum and the room reeked of sex. I didn't know if I should be proud or shocked. Maybe a little of both.

I knew the party was over when all the men started getting dressed. I followed their lead and when I was ready I asked Tom if he wanted me to take her home that night and save him the trouble in the morning.

"No, no. The bet was until morning. Besides, I think I might like a blowjob when I wake up," he answered.

"Suit yourself," I replied and walked out the door, leaving my wife to spend the night with one of my best friends.

The next morning she returned home about ten o'clock looking much cleaner and fresher than the last time I had seen her. She confirmed that Tom had indeed demanded that she suck him off before breakfast, which she did. Then she said that they talked for a while before he drove her home.

Later that day while Jolene was out shopping for groceries (hey, the mundane shit still has to get done), Ed Jacobson paid a visit.

"Jo is out shopping right now Ed, but I can send her over later if you want," I offered my neighbor my wife just as easily as I had my friend the night before.

"Actually, I stopped by to talk to you. I have an idea that I think you will like," Ed replied.

For an old guy, Ed was quite the pervert, so of course I was interested. "What do you have in mind?"

"I have a few friends that are either widowers like me or divorced that I would like to share your wife with."

"Like that guy the other day when you had her tied up?"

"Leon, yeah, he's one of them."

"OK, but you don't really need to ask me, you know. I trust you."

"That's I appreciate that, but I'd like to make more interesting than just saying 'hey, do you want to come over here and fuck my neighbor?' I want to add some mystery and excitement."

"All right, what's your plan?"

Then he went on to explain his idea to me. I thought it sounded very fun indeed, so I agreed to help him put it into motion and provided him with the materials he needed.

The next day Ed and I tried our out new game for Jolene. We went to the gym like we normally did and when we got back I told my wife that I had some errands to run, so I just dropped her off at the house and drove around the block. I knew she would find the full-sized manila envelope taped to the door that Ed had left for her. Inside there was a transparency with some random looking words printed on it at irregular intervals which didn't make any sense. There was also a note for her that read:

"Put on your one-piece red sun-dress, some sandals, and nothing else. Then drive out to the state park south of town and park your car in visitors lot B. Bring the envelope with you and be there by 3:00. Take the walking path up the hill and follow the signs to the scenic outlook. Sit down on the bench there and wait for a man to approach you with a piece of paper that has your picture on one side and a bunch of random words on the other. Place the transparency over his paper and line up the corners. This will reveal your next instructions."

I was not running any errands, of course. I was with Ed at the park waiting for my wife to come up the trail. We had found good hiding spots where we could watch the proceedings using modest power binoculars. Several people and one couple passed by us while we waited, however none of them went to the scenic outlook. Ed had already checked it out and found that almost nobody went there anymore because some trees had grown up and blocked most of the view. That made it a perfect location for our first game.

About twenty minutes after three we spotted Jolene walking briskly up the path. I noticed she was wearing the dress I told her to and was also carrying the envelope. Despite the long walk up the hill she was only breathing slightly heavier than normal. Man she was in good shape these days. I was proud of her. Ed told me that in addition to the scenic view being partially blocked in recent years, many people just found the climb up the hill to arduous. I was surprised how well he negotiated it; for an old guy he was in pretty good shape himself.

My wife walked past our hiding place, her tits bouncing wonderfully under the thin cotton fabric, and headed down the short path to the outlook. After she was out of sight we moved to our second hiding location near the clearing where the bench was to wait for Leon. Jolene was there sitting on the bench as instructed. I wondered what she was thinking.

A few minutes a man came walking down the path towards the bench where my wife sat with her big manila envelope. Ed whispered that it was not Leon and I got a little worried; and excited. It was the chance of getting caught that made me interested in this game after all. We watched as he entered the small clearing and slowed down and stopped near the bench. It looked like he stood there for a moment, not sure what to do next. I think I understood. He expected to see a nice scenic view, but instead all he could see were trees. But then there was a beautiful woman in a little sun dress sitting there on the bench and he was debating whether he should say something.

He finally decided to say something to her. She looked up at him kind of questioningly. Probably wondering why he had not given her the page with her picture and the encrypted message. Finally she spoke a couple of words, and then a small conversation ensued. I really wished at this point that I had a directional microphone and a small audio amplifier so that I could hear what they were saying. I made a note to myself that we needed to figure out a way to get audio in the future.

After a few minutes of chit-chatting the man turned around and left. Evidentially Jolene figured out he was not the man she was waiting for and brushed him off. Good girl, I thought. A few minutes later Ed tapped me on the arm and pointed. A black man who looked to be about fifty emerged from around a small bend and was heading for the clearing with the bench where my wife sat. Ed whispered "Leon".

He went straight to Jolene and showed her the piece of paper with her picture and the random words. She smiled at him and pulled the transparency out of the envelope and handed it to him. He positioned it over his page and they both read the message. I couldn't read it from where I was, of course, but I didn't need to; I knew exactly what it said.

"Remove her dress and don't give it back until she has finished her task. That task is to suck your cock until you come in her mouth. She is to swallow every drop. If anybody else discovers your little tryst she must offer to suck them off too, male or female. Only after everyone has been serviced will you return her dress and allow her to leave. Place the transparency and the picture in the envelope. She must return it to her master to prove she has accomplished her task."

Ed had watched that spot for weeks and had only seen adults check out that particular scenic outlook, and even then there weren't many. It was just too difficult a climb up that hill for children and teens were generally too busy doing other things than wasting their time going up there. But to be safe we had Leon put a "Trail Closed" sign over the "Scenic Outlook" sign and Ed and I were positioned so that we could head off anybody long before they could see anything, if necessary.

When they finished reading the note Leon put the transparency and the page with the picture into the envelope and put it down on the bench. Then he reached down and pulled my wife's dress up. She raised her arms and he easily slid it off. She looked absolutely stunning sitting there nude in the sunshine, the breeze playing with her hair.

Then she pushed his shorts down to his ankles and grabbed his semi-rigid cock with both hands. She admired it for a moment before lowering her head and taking it into her mouth. I became mesmerized watching her pink lips make love to his ebony rod, so I startled when Ed jabbed me and pointed at the path leading to the clearing.

I looked up and saw someone heading our way. It was the young man that was here earlier before Leon arrived. I looked at Ed and shrugged my shoulders. He just smiled back. I guess we had just decided to let things play out and see what happened.

When our young stranger came around the bend and saw what was happening over on the bench, he froze in mid stride. Probably could not believe his eyes. He took a couple more halting steps forward, obviously unsure as how to proceed. Jolene noticed him then and gave him the "come here" gesture with her hand will continuing to suck on Leon's cock.

The stranger walked up to the bench and stopped within reach of my wife. Jolene stopped her oral attack on Leon's dick long enough to say something to the new arrival and then resumed her blowjob. The stranger just stood there watching them. After a few moments Jolene reached out and pulled down his zipper, but she was having problems with the button on his trousers. This woke him up and within seconds they were around his ankles.

Jolene grabbed his already hard cock and started stroking it slowly as she continued to suck Leon closer and closer to his climax. When I saw his body stiffen and his head tilt back I knew he was pumping his jism into my wife's mouth. She stayed with him through his orgasm and milked him dry. When she finally let his cock slip from between her pink lips it was already getting soft.

Now it was the young stranger's turn and she attached his cock like it was a steak and she hadn't eaten for a week. I wondered if she thought he was part of the setup too, and whether others would show up before she was finished.

Our young stranger didn't last long though and soon was adding his load to Leon's in her stomach. When she was done milking him for all his cum I noticed that he was still mostly hard and probably could have gone again. But he didn't ask for seconds; instead he pulled up his trousers and left in a hurry. Leon handed Jolene her sun-dress back, turned, and left. She slipped the small dress on and waited for a few minutes, probably waiting to see if Ed or I would show up. We had previously decided to not reveal ourselves so that she would never know if we watched her during these challenges or not.

Finally my wife stood up and headed back in the direction of the main path. Ed and I waited for ten minutes or so to make sure the coast was clear, and then returned to my car which was parked at the other end of this particular walking path.

As we drove back Ed and I talked about what we had just witnessed. We agreed that it was a very successful trial of our new game and we couldn't wait to play it again, however next time we planned to turn up the heat. When we got nearer to our houses I asked him who he thought Jolene would return the envelope to; who did she think her master was? Ed thought it would be me, but I wasn't so sure. We had intentionally left the wording vague to see what she thought.

Since the path from the scenic outlook back to my car was shorter than my wife's, we made it back before she did. I was sitting at my computer reading an Internet blog when Jolene returned home. Without saying a word she placed the envelope on my desk, kissed my neck, and walked upstairs. After a few minutes I followed her. She was on our bed, naked and pushing a big black dildo in and out of her hot little snatch.

"I guess you enjoyed your challenge," I said from the doorway.

"Oh god, I'm so horny. I wish you would have told him to fuck me."

"Maybe next time," I replied as I stripped out of my clothes. I watched her as she fucked herself with the fake black cock, stroking my own hard-on slowly. After she came I turned her over and fucked her doggie style, pulling on her hair and slapping her ass. She had another noisy orgasm before I shot my load deep into her hungry pussy. Then I sent her over to Ed and told her to fuck him dry as well.

That night Tom called up and said that his friend Ned had fixed his fucking machine and wanted to know if Jolene was available to test it. I gave the phone to my wife and she talked to Tom for a few minutes. It sounded like they were agreeing on a time.

"I told him we would meet at his place at seven o'clock tomorrow night," she informed me.

"Damn, I didn't know he was talking about tomorrow night. I already have something planned." I was meeting with Ed to plan some new adventures for Jolene, so maybe this was a good thing.

"Do you want me to call him back and cancel?"

"No, you can go without me."

"OK. I'll tell you all about it when I get home."

Sunday night I kissed my wife, patted her ass, and sent her off to visit my best friend and his crazy inventor friend so that she could test his fucking machine while they watched. As if that didn't sound strange enough, I was on my way over to my retired neighbor's house to plan some perverted challenges for her. I can truly say my life is anything but boring.

Ed and I brainstormed for a couple of hours and managed to create two additional challenges, although we did have ideas for several more. But I couldn't wait to get started on putting the next two into action. By the time Jolene returned home I was tired and getting ready for bed.

"How did things go tonight with the Tom and the mad scientist?" I asked her when she walked into the bedroom.

"Wonderful. I rode it for a over an hour while Ned recorded everything. Apparently he wants to make profiles that he can ship with it."

"How many times did you come?"

"Oh, I don't know. I lost count. Maybe ten or twelve. It's hard to tell when one just runs into another."

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