I’ve modified the original very hot story from by the very talented jdrew2001 which I originally read on literotica.com to my own kinks and tastes. All of the credit for goes to jdrew2001. Have a look at my pics in the galleries section that related to my particular kinks. I’ve also posted another story on this site. Hope you enjoy!
My wife and I were monogamous for several years after we married but then even though we still loved each other intensely our sex lives had become routine and stale. We each craved the excitement that came with having sex with someone new. The different touch, the different sounds, the different taste. Because we were always open with each other we talked about our feelings and eventually concluded that the answer was to open our relationship to other sex partners and have done so for the past umpteen years. Having such an open relationship has allowed us to maintain a special relationship between us as a couple while at the same time being able to enjoy a variety of other sex partners.
I guess over those years my wife, her name is Jennifer, has gotten the better of the bargain. Like many women who are in an open relationship she has had a multitude of sex partners, more than I, largely because women have the advantage of being able to fuck for as long as they want to while we men can only cum a few times before we are done for the night.
We always practice safe sex with our other partners and we do not have intercourse, whether vaginal or anal, without a condom except when we have written proof that our partners have been tested.
Before moving on, let me describe Jennifer. She is 5'2" tall and weighs 115 pounds. She has brown eyes and medium length brown hair that at times looks reddish in certain light. Her skin is very pale and she has a lot of reddish freckles on her tits and shoulders. Her breasts are a natural B cup topped with light brown/pinkish nipples which get about a half an inch long when she is aroused. Her nipples never get fully soft so if she goes braless you can usually get a glimpse of her nubs through her top. Jennifer has a very, very thin waist which gives her a classic hourglass figure and an ass to die for. We never had children so Jennifer's pussy is nice and tight.
My wife is also very competitive and into sports like football and we often argue about which team will win a particular sporting event. Over the years we have made many bets against each other for various stakes, both sexual and non-sexual. Jennifer knows sports better than most guys I hang out with and her bets are well thought out. It is this betting that led us to where we are for this story.
We were cleaning up after a poker game at our house when I sat down at the table, started to shuffle the cards loudly against the table and said, "One hand, winner takes all."
"What's all?" Jennifer asked as she walked over towards where I was sitting.
"If you win I will buy you that necklace we looked at yesterday," I said.
"And if you win?" Jennifer inquired.
"If I win, you cut the cards and have to have sex with the number of men that is equal to the number on the card you drew," I told her as I continued to shuffle the deck.
"What if I draw a picture card?" Jennifer asked.
"Aces count as one and then the suits go up to 13 for the kings and to make it more interesting let's say that hearts mean you have to fuck the guys, diamonds mean blow jobs, clubs mean anal and spades mean all three," I said.
"Wow, pretty specific aren't we," Jennifer said, "You must have stayed up late thinking all of that out."
Actually I don't know where that idea came from, whether I read it somewhere or it just popped into my perverted mind.
Jennifer pulled out a chair and sat down across from me at the table. "Deal," she said.
"Five card draw," I Jennifer announced as I dealt each of us five cards.
The game went very quickly because there was no betting as the stakes had already been set. The end result was that I would up with a pair of aces which beat Jennifer's pair of nines.
I collected up the used cards and put them back into the deck, shuffled it a few times and placed it in front of Jennifer.
She looked over at me for a moment and said, "Well here goes nothing," and cut the deck about half way down. Jennifer turned over the top half of the deck and we both saw that she had drawn a five of hearts. That meant that she would have to fuck five guys.
We both realized that we had not been specific enough in setting up the rules as one glaring omission was how long Jennifer had to perform her task. We talked about it and decided that it would be fair to give her until the next poker night at our house which was four weeks away.
As Jennifer and I had been in an open relationship for several years she really did not have any trouble hooking up with five guys and getting fucked by each of them. In fact, she had finished with the fifth guy and still had a few days to go before the date of my next poker game.
The night of the next poker game came and my four friends showed up as usual. We had been playing for years and wanted to keep the game friendly so we agreed early on that we would quit at midnight so no one felt pressured to keep playing and that we would each buy in for $50 to start the night. When your $50 was gone you were busted and done for the night. Jennifer went out with a girlfriend of hers to a movie or something and got home just as the last guy was leaving.
She walked over to the poker table, picked up the deck and said, "Do I get a re-match?"
"Of course," I said and we agreed on the same stakes as before.
Another quick game except that this time Jennifer won and I got her the necklace the next day.
Same story the following month and Jennifer had a pair of matching earrings to go with the necklace.
Each time we played the game we thought of another aspect of the rules that we had not covered so as time went on the rules got more and more detailed and specific. For example, we added a forfeit that Jennifer would have to do if she lost and was not able to perform all of her tasks in the allotted four weeks. We also added two jokers to the deck and if Jennifer drew a joker she would take the next card and double it. The stakes also increased as well in terms of what Jennifer got if she won.
Eventually over time we dispensed with the card game between us and got to the current set of rules which were as follows:
1) Jennifer would draw one card from the deck on the first day of the month. The value of the card would be the number of guys she had to have in the coming month. If Jennifer drew a joker she would take the next card and double it. Once a card was drawn it would not be replaced in the deck.
2) Aces would be ones going up to 13 for kings. Hearts meant she had to fuck the guys, diamonds were for blow jobs, clubs were for anal and spades meant all three.
3) A guy counted against the goal if Jennifer got him to come in her mouth, ass or pussy, as applicable. In the case of hearts, diamonds and clubs, Jennifer could do more with the guy than the required activity but it was her choice.
4) A guy could only count once in any given month and I did not count.
5) In the case of spades for a guy to count Jennifer had to get him to come in each of her openings or he would not count. Because not all guys can come three times in a single session the three times could be over more than one session.
6) Jennifer could take the guys on individually or in whatever groups she wanted but no more than a third of the guys could be at a single session at a sex club and there could be only one sex club session in a month.
7) The game would run for eight periods of six months each (leaving four cards that would not be drawn) with a new prize and forfeit at stake in each.
8) Jennifer had one put back in each period where she could draw a card and if she did not like it she could put it back in the deck and draw again.
9) Jennifer was allowed one "do over" each period if she missed her goal in any one month but she would have to add five to the goal she had missed.
We went back and forth about these rules for a while until we were in agreement and decided that the game would start the first of the coming month. All we had to do now was to come up with the prize and the forfeit.
Jennifer said that she wanted a new car, specifically, a Mini Cooper Convertible, and I breathed a sigh of relief because when I heard "new car" I was thinking "Mercedes" or "BMW" would be the words that followed.
For the forfeit I told Jennifer that she would have to have her nipples and clit pierced. She blanched and tried to talk me out of it until I challenged her saying, "Well if you are chickening out then I suppose we will just not play the game."
I knew that her competitive side would not let her walk away from a challenge even though she dreaded the forfeit.
I was right as Jennifer quickly said, "I am not chickening out. Just keep your checkbook handy because you will need it at the car dealer."
A couple of days later the first of the month arrived and I got a new deck of cards out of the cabinet where I kept the poker chips and other assorted paraphernalia. I unwrapped the box and took out the cards.
Jennifer came over and sat down next to me and watched as I checked to make sure the deck had all 52 cards plus two jokers in it. Once I had verified that the deck was complete I started to shuffle it and did so for a couple of minutes to be sure the cards were well mixed. As with any new deck the cards came arranged by suit from low to high and I wanted to be sure that the cards would be in the deck randomly.
I finished shuffling and then laid the deck in front of Jennifer and said, "All yours."
Jennifer looked at the cards for a moment and then at me and smiled. She reached for the deck took it in her left hand and then fJennifered out the cards. She thought for a moment and then picked a card about two thirds of the way in. Jennifer turned the card over and we both saw that it was a four of hearts.
"Piece of cake," Jennifer said.
I knew she was right because with our swinging/swapping it would not be a problem for her to fuck four guys during the next month. It wasn't. Nor was it a problem for Jennifer the next two months as she drew a six of diamonds and a three of clubs.
With Jennifer drawing so many low cards I was beginning to think that she should audition for Deal or No Deal but I knew that the deck was still filled with high cards and that no spades had been drawn as yet.
In month four her luck ran out and she drew a jack of diamonds. We both knew that even with our regular swapping partners Jennifer would have to hustle up a couple of more cocks to suck in order to get to eleven for the month.
Jennifer solved the problem by going to one of the swing clubs we go to from time to time. She dressed up in a garter and hose with CFM heels and put a raincoat over that so from the time she checked her coat at the club all of her assets were clearly on display. She used a bright red lip gloss which highlighted her luscious lips.
After her swapping partners and two other guys she picked up she needed only three more guys for the month and needless to say she did not have trouble attracting enough men at the club to put her over the top for the month. Jennifer looked so hot dressed (or undressed actually) the way she was and with her on her knees sucking loudly on a guy standing in front of her it did not take long for a small line of guys to form hoping that she would service them as well.
But that was not Jennifer's style and after the third guy she got up, smiled at the guys waiting and said, "Maybe later."
For whatever reason despite her having had numerous partners and participating in several gang bangs with up to six guys Jennifer was not into scenes where she would service one guy after another after another. She said that although she knew that all of her extramarital activities definitely made her a slut that a woman who just serviced a line of guys was a cum dump and she did not want to be a cum dump. I thought that the distinction was pretty nuanced but for Jennifer it was important so I never made an issue of it although like with anything you do not have I did want to see her be a cum dump at least once.
Month five saw Jennifer's luck return and she drew a two of hearts. As I said, put this woman on Deal or No Deal.
Month six yielded the nine of clubs and I thought that there would soon be a new car in Jennifer's side of the garage but Jennifer procrastinated and let things go. With a few days left in the month she was still a couple of guys short when we got a call that her sister had been in an automobile accident. Jennifer left immediately to be with her sister and could not really do anything sexually while she was there and ran out of time.
"I get a do over if I need it, right," Jennifer asked me on one of our phone calls.
"Yes, you do but you have to add five to the number so that makes it 14," I replied.
"Can we postpone things a month because I have to stay with my sister another few weeks?" she asked.
"Sorry, there is nothing in the rules about time outs so you are on the clock as of right now."
Jennifer whined and moaned about that being unfair but I would not yield. I finally saw the opportunity to win and have her do the forfeit of having her nipples and clit pierced.
When we started this bet and negotiated the rules I thought it would be harder for Jennifer to find enough guys when the cards got high especially if they were spades and since she had to go six for seven (counting one do over) to win I thought the odds were in my favor. I guess I totally underestimated how easy it would be for an attractive woman to get guys to have sex with her. I was also counting on some spades being drawn but they were all still hiding somewhere in the deck.
Anyway, Jennifer did not get back home until there was only a week left in the month and she got to work getting her ass fucked. She connected with several guys from our swing group but several others were out of town because it was the summer. Our two regular sex clubs were also closed, one for renovations and one while the owners took their summer vacation. Jennifer was clearly running out of time and options.
With only four days left in the month Jennifer said to me, "I'm going to talk to Paul."
"Are you sure you want to do that?" I asked.
"I really have no other choice unless I want to see my nipples and clit pierced."
Paul was a good looking black guy we met at one of the sex clubs we frequented. He was also a dominant who trained women to be slaves. He also put on a bdsm show a couple of times a year at the club. He had hit on Jennifer wanting her to do a bsdm scene with him but she had always turned him down although she did let him fuck her once.
Paul was also part of an all black gang bang crew that offered their services on the internet to women who wanted to be banged by a group of black men. The guys were all tested regularly for STDs, well endowed and offered a safe experience for interested women and couples.
We both knew that there would be a price for Jennifer to pay for Paul's help and that price would include submitting to him.
Jennifer got up off of the couch, walked into our home office and closed the door. I could hear her talking on the phone for a few minutes but could not make out what she was saying.
The office door opened and Jennifer walked out and went over to the bar, got a glass from the shelf, dropped some ice in it and filled it almost to the top with some of our best scotch. I could see her hands tremble as she raised it to her lips.
"What did he say?" I asked.
"Paul said he would arrange it but that he had some conditions," she replied.
"His conditions are that I take on the full crew one after the other and that I be restrained during the process. The crew will also be allowed to fuck my mouth and pussy after they have fucked my ass. He will give me a safe word and a slow word to use if things get too intense and I have to participate in his next bdsm scene at the club," Jennifer related.
Jennifer continued, "He said that he would get at least nine guys to be there including him (nine was the number Jennifer needed to get to her revised monthly goal) but if he got more I would have to take them all up to 14. He said that because all of the guys would be currently tested no condoms would be used."
I could see now why her hands were shaking as she again raised the drink to her lips.
"So what did you tell him?" I asked.
"That I would think it over and let him know before noon tomorrow."
Jennifer spent a restless night and I could feel her tossing and turning on the bed next to me. She looked tired the next morning at breakfast and as I read the paper while nibbling on a muffin she quietly said, "I'm going to do it."
I looked over at her and nodded.
"What Paul and his crew are going to do to me scares me but I am more scared of the pain of having my nipples pierced and especially my clit because you know how sensitive it is," Jennifer said.
We left for work and Jennifer called Paul on her cell shortly before lunch.
He told her that he would set things up for Saturday night and that we should come over to his place around 4PM so that he could prepare her. He told Jennifer that she was to shave so that she had no hair anywhere on her body other than her head. She was to wear only heels and a trench coat.
Jennifer spent most of the day Saturday getting ready and really looked hot. Her skin was smooth and hairless and glistened with the lotion she had put on herself. I walked over to where she was standing in front of the mirror and ran my hands over her body. I rubbed her right breast with one of my hands and my other hand slid down to her pussy. When I started to finger her I was amazed at how wet she was. She moaned as I slipped one then two fingers into her.
"Hmmm, the thought of being ass fucked by Paul and his crew must be turning you on," I said.
Jennifer replied, "I am still scared because I know that all of the guys will be hung as I looked at their website and I hate the thought of being restrained and being a cum dump but somehow that fear and trepidation has turned me on something fierce."
I continued to finger Jennifer for a few moments and she started to hump her pussy back onto my fingers. A few moments more and she had what she later told me was her third orgasm of the day.
Jennifer finished her makeup and put on her black CFM heels. She walked over to the foyer closet, took her trench coat, put it on and said, "Let's go, before I change my mind."
We did not speak during the five minute ride to where Paul lived and I parked a few doors down from his house. We got out of the car and I had to hurry to keep up with Jennifer who was walking fast because she said she felt very conspicuous wearing CFM heels and a trench coat in the middle of a nice summer day.
We walked up to the door and I rang the bell. Paul opened the door a few seconds later and shook my hand. He looked over at Jennifer and said, "Lose the coat before you come in."
Jennifer looked around nervously to see if anyone was going to see her ****** herself. She opened the belt on her coat, slipped it off her shoulders and handed it to me. I could not believe how incredibly sexy she looked standing there naked except for a pair of CFM heels. The vision did not last long as Jennifer turned and walked into Paul's house.
Paul was waiting just inside the door and said to Jennifer, "Kneel." She was startled and after a few seconds dropped to her knees. "Spread your knees wider," Paul said and Jennifer slid her knees further apart ******** her pussy even more. Paul walked over and stood in front of Jennifer.
"OK, here is how it is going to go. From here on out you are to do what I or the guys in my crew say. If you want to quit, your safe word is 'red.' If you say 'red' whatever is happening to you will stop and you will be free to go. Tomorrow morning your husband will take you to have your nipples and clit pierced," Paul said.
"Your slow word is 'yellow' and if at any time things get too intense you can stop the action for thirty seconds by using your slow word. You will be allowed to use the slow word twice," he continued.
Paul finished by saying that from then on Jennifer was to address him and any member of his crew as "Sir," and to do what they said without question or hesitation
"Do you understand what I just told you, Paul asked.
"Yes," Jennifer meekly replied.
Paul reached out and took Jennifer's left nipple in his fingers, squeezed it hard and twisted it saying, "Yes what?"
Jennifer cried out at the abuse of her nipple and quickly said, "Yes, sir."
"Very well then," Paul said, "Let's get started."
Paul turned and started to walk away and said to Jennifer, "Follow me."
Jennifer obediently followed Paul down the hall. He led her into his master bathroom and she gasped when she saw the enema bag hanging from the wall. Jennifer later told me that she did not know what to expect when Paul said he was going to prepare her and thought he would just fuck or otherwise use her before taking her to wherever her anal gangbang was going to take place.
"Over here," Paul said as he motioned to a spot on one of the rugs.
Jennifer walked over and stopped. "Get down on your hands and knees," Paul said. Once Jennifer was on the floor Paul pushed her shoulders down and positioned her so that her ass was sticking up in the air.
"Spread your cheeks and show me what we are going to be fucking tonight," Paul said.
Jennifer slowly reached behind and pulled her ass cheeks apart. My heart skipped when I saw how lewd she looked with her ass open and ******* the way it was.
Paul saw me looking and said, "Take a good look because her little asshole is not going to be that little when we are done with it."
Paul then got a tubular metal bar from the countertop that had four leather cuffs attached to it. He took the bar and put Jennifer's ankles into the outer cuffs and locked them in place. He told Jennifer to put her hands through her legs and he then cuffed her wrists to the inner two cuffs. She was now fully restrained and had no choice but to remain in her ass up humiliating position.
But Jennifer did not as yet appreciate how humiliating things were going to get.
Paul then took a tube of lube and greased up Jennifer's ass forcing first one then two of his long fingers into her nether hole. Jennifer grunted at the invasion.
Satisfied that her ass was sufficiently lubed Paul then took a double balloon bardex nozzle off of the counter. I could see Jennifer's eyes widen as she had never seen one before. Paul saw the look on her face and said as he held it in front of her, "The larger balloon goes inside of you and then we inflate both. Once they are inflated whatever solution I put inside of you will stay there for as long as I want it to."
While he was saying this he inflated both balloons and Jennifer whined when she saw and understood what would soon be inside of her.
Paul deflated the balloons and got behind Jennifer. He slowly forced the larger balloon into her ass and when it was seated properly he closed the valve and began to pump the bulb. Jennifer was silent for the first two pumps but said "oh" with each of the last three pumps as she felt the balloon expand. Paul then closed the valve on the outer balloon and then pumped it to its maximum. Jennifer groaned as the two balloons tightened towards each other effectively sealing her up.
Quickly Paul stood up and got the hose and connected it to the nozzle. When he was satisfied everything was tight he said to Jennifer, "Try and relax as much as possible, you are going to feel very full."
He then opened the valve and the solution began to flow into Jennifer. She grunted when she felt the first blast of the warm solution flowing into her bowels and as the flow continued she started to groan. Because of her ass up position the flow was unimpeded and she started to fill up quickly.
We could see that she was getting uncomfortable and Jennifer started to beg and plead with Paul saying, "Please, Sir, no more. I cJenniferot take any more."
"Actually you are only about half way and there is still over a quart to go," Paul said.
"Noooooooo," Jennifer whined and pleaded even louder.
Paul stopped the flow for a moment and said to Jennifer, "You can always use your safe word. I talked with your husband and he is in a no lose situation. If you go through with the black anal gangbang he gets to watch and see you used as a cum dump. If you use your safe word he gets to have your nipples and clit pierced. I also win because regardless of what happens you are going to do a bdsm scene with me at the club later this year."
I knew that Jennifer realized what her two alternatives were but when Paul explained them to her this way I think she really understood how bleak her two choices were.
"OK, here we go again," Paul said and he opened the valve again.
Jennifer immediately grunted and kept grunting and moaning as her bowels filled to capacity. She did not beg or plead however so she must have decided that going through with her anal gangbang was the better alternative.
We finally heard the sound of the bag reaching empty. Paul shut the valve on the hose and said, "Now we will just leave that inside of you for a few minutes."
He and I went into the kitchen to get a beer and left Jennifer in the bathroom. Jennifer later told me that she felt very uncomfortable as she was cramping almost constantly and felt incredibly full. She also felt totally humiliated being restrained as she was with the bardex nozzle sticking out of her ass.
Paul and I finished our beers and we returned to the bathroom.
He walked over behind Jennifer and released her hands from the cuffs and then did the same to her ankles. He helped her to her feet and then showed her how to release the air in the balloons and then said, "We will give you some privacy for this part. Wash up the nozzle and shower when you are done."
We walked out of the bathroom and closed the door behind us.
Paul and I were on our third beer when Jennifer finally walked into the kitchen. She was naked except for her black CFM heels.
"How do you feel, Jennifer," Paul asked.
"Exhausted," Jennifer said and then as Paul reached for her nipples, "Exhausted, Sir."
"Well, you may want to have a drink in any case," Paul said and Jennifer asked for a vodka tonic.
After another round Paul looked at his watch and said, "We better get going."
Jennifer thought that we were leaving and said, "What about my coat, Sir?"
Paul said, "We're not leaving yet. We are going to go into the bathroom for your rinse. We want you nice and clean because the boys are all tested and do not have to use condoms some of them may want to go from your ass to your mouth."
Jennifer shuddered at these words and I thought she may call a halt to things but she somehow held herself together.
Jennifer later told me that she decided to try to get through the anal gangbang by getting through each step one step at a time. She said that what was most disconcerting was when Paul threw another unexpected step into the process which he did more than once.
About half an hour later Jennifer padded into the kitchen. She was naked except for her CFM heels. I was actually surprised that she had remembered to put them on but this woman continued to amaze me with her toughness and resiliency.
Paul had a vodka tonic ready for her and she shakily brought it to her lips. You could tell that Jennifer had a rough couple of hours and we all knew that more tough times lie ahead.
Jennifer came over and sat down next to me and I put my arm around her shoulder and idly fingered her right nipple. It hardened almost immediately and I knew that despite everything that had been done to her Jennifer was still smoldering under the surface.
We sat and talked for a while and then Paul looked at his watch and said that it was time to go. I asked where we were going and he said that he had arranged with the owners of the sex club that was closed for their vacation to use it. Jennifer immediately perked up and asked me if the rule about only a third of the goal being able to be satisfied at a single session at a sex club would apply and I said that it was a technicality about whether it applied since the club was closed and that I would give her the benefit of the doubt and waive that rule for tonight.
Jennifer appeared to like my answer and finished her drink.
Paul got his car keys and said that he would drive and opened the door down to his garage. Jennifer got up and walked down the stairs to his car never once asking if she would be allowed to wear any clothes. As I said, an amazing woman.
Paul put Jennifer into the passenger seat in the front and we were off. She just sat there calmly even when he reached over and parted her legs so that a trucker that had stopped next to us at a traffic light could get a better look.
It was almost as though Jennifer had decided that since she was off to have nearly a dozen black guys fuck her in the ass what difference did it really make if some truck driver saw her naked.
As we got closer to the club Jennifer's demeanor changed from the confident to the less so. She reached her hand to the back seat and took my hand in hers and held on tight. I could tell she was thinking and worrying about what was going to happen to her when we got to our destination.
We got to the club and Paul pulled into the parking lot and stopped the car. I got out and opened the door on Jennifer's side and she stepped out without hesitation, took my hand and walked towards the door. Naked as the day she was born except for her heels Jennifer walked deliberately across the parking lot to meet her gang bang crew.
Paul opened the door to the club and stepped inside. Jennifer and I followed. It took us a few minutes to get used to the darkness and then we moved to the middle of the club. Jennifer could hear approving voices as the members of the crew saw her naked body stroll into the center of the club.
Paul raised his hand and the voices stopped. He said, "Let me introduce you to Jennifer our gangbang anal slut for this evening," and he gestured towards Jennifer. I could see Jennifer shudder at his words as if the reality of what she had agreed to do had finally fully hit her.
Jennifer looked over at the bar area and saw ten guys standing around in several small groups. Including Paul that meant that her gang bang crew would be a total of eleven.
All of the guys were black with skin tones ranging from the lighter to the truly black. All appeared to be in shape and ranged from about 5' 10" up to around 6' 4" in height. You could tell that all of them were looking forward to fucking Jennifer in the ass and possibly in her mouth and pussy.
Paul then explained the bet that Jennifer and I had made and said that Jennifer had to have at least nine guys cum in her ass for her to win and get her new car. If she failed for any reason she would have to have her nipples and clit pierced. Hearing this the guys realized that they would not have to hold back and you could hear comments like, "We are going to tear up that tight white ass."
"Jennifer has two safe words," Paul said. "The word 'yellow' means that whatever is happening stops and she gets a thirty second break and 'red' means that the whole scene stops. Jennifer can use the slow word twice," he continued.
"Once the scene starts Jennifer has to do everything she is told by any of us and her only way out is to either finish the scene or use her stop word. The scene starts now and Jennifer is ours until one in the morning," Paul said.
I glanced at the clock behind the bar and saw that it was just 8PM. Jennifer was going to have a tough five hours.
Jennifer knew from talking with Paul and looking at his crew's web site that all of the guys were hung, a solid seven or eight inches with a few almost nine and very thick. The guys also all had great stamina and could fuck long and hard. We also learned later than many of them took Viagra or one of the other ED drugs before scenes like this. Those drugs in younger guys had the effect of making their erections even larger due to the increased blood flow and allowed them to get hard again sooner. Apparently those drugs have become popular in the porn industry for those reasons.
The guys started to strip and soon a group of four of them surrounded Jennifer. Even in her 4" heels the guys dwarfed her and she looked so tiny and vulnerable standing among them. The contrast of her pale white skin against their darker complexions was also stunning.
In seconds, Jennifer had hands all over her body and her tits, ass and pussy were getting mauled. Fingers probed her two lower openings and she bucked and writhed at the invasions.
Soon she was pushed down to her knees and presented with a large cock to suck. As she took it into her mouth its owner said, "We didn't get a fluffer so you are going to have to do the work and get us nice and hard so we can fuck your pretty white ass and pussy."
Jennifer struggled to get the cock into her mouth as the guy pushed deeper and tried to get into her throat. He could only get part way in but it was enough to block Jennifer's ability to breath through her mouth and she was soon sputtering from her nose trying to get her breath.
The guy sawed in and out of her mouth for a few minutes and then another guy took his place followed by another and another.
Paul then stepped in and helped Jennifer to her feet saying, "Time to get you set up."
He led Jennifer over to a padded bench and when she saw it Jennifer knew that she was looking at the place of her defilement. She knew that she would be tethered there for the rest of the night and used and abused with her safe words her only escape.
Paul adjusted the bench so that it was about waist high and then bent Jennifer down over it. "It's cold," Jennifer said as her tits touched the flat part of the bench. "Don't worry," Paul said, "You will be warm soon enough."
The bench had a slight downward angle so that Jennifer's head was a bit lower than her butt. Two of the other guys started to strap Jennifer to the bench. They put cuffs on her ankles and chained her legs wide apart. Larger cuff connected to another set of chains were put just above her knees further insuring that Jennifer would not be able to close her legs. Another pair of straps was put over her waist and shoulders securing her torso to the bench. Finally, Jennifer's hands were pulled out to either side and secured with wrist cuffs.
Jennifer's head hung over the front of the table but not for long. Paul came around and got a U shaped device that was padded with the same material as the table and slid it into a slot at the front of the table. He adjusted the sides so that they pressed against the sides of Jennifer's head thus immobilizing her head as well and putting her mouth at the perfect angle to service the many cocks that would soon be pushing down her throat.
When I looked at Jennifer's face I could see her eyes wide with fear but as I looked closer I thought I also saw some lust in her eyes. Jennifer later told me that she had a multitude of feelings as she was being secured to the bench ranging from fear that morphed into more and more lust as each strap was put into place and she was secured for her night of service. She said that although she never wanted to be a cum dump she began to understand what women who were had experienced as they waited for their body to begin to be used by man after man.
Paul went around behind Jennifer and started to lube up her ass. You could hear Jennifer grunt as he forced first one, then two and finally three of his fingers into her little puckered hole. "Three fingers are small compared to what is soon going to be in your ass," Paul said as he withdrew his fingers from Jennifer's ass.
Jennifer was definitely no stranger to anal sex but she had only had one or two really big cocks in her ass and now she was strapped down with a room full of very well hung guys lining up to fuck her ass.
The first guy, who was still hard from Jennifer sucking him earlier, stepped up behind Jennifer, lined his cock up with her ass and drove it in to the hilt in one strong push. "Arrrrrgh," Jennifer yelled and begged him to start slowly. Her pleas were ignored as the guy started to fuck her ass hard right from the start. Hard thrust after hard thrust plowed into Jennifer's upturned ass and she could do nothing but take it and verbally express her discomfort and displeasure. But she did not do that for long because a few moments after her first ass fuck started another guy got in front of her and fed his cock into her mouth.
Like the fellow in her ass the guy in Jennifer's mouth did not waste time and started to fuck Jennifer's mouth and throat hard. She was now getting it from both ends and could not even use her safe words if she wanted to because her mouth was too full of cock for her to say anything intelligible.
The cocks continued to saw in and out of Jennifer's mouth and ass for several minutes and Jennifer continued to make mewling noises and other unintelligible sounds. After a couple of very hard thrusts the guy fucking her ass said, "Here it comes baby," and fired his load deep in Jennifer's bowels. He pulled out. The guy in Jennifer's mouth did the same and took his place in her ass. Jennifer thought that she would get at least a small break in between ass fucks but her ass was empty for just seconds before a second large cock was forcing its way into her. Like the first guy this guy immediately fucked her hard and to the hilt.
"Oh, oh, oh," Jennifer said with each stroke but her words were soon cut short as another cock was pushed into her mouth. After a few minutes the second guy dumped his load into Jennifer's ass as did the third a few minutes after that.
Jennifer told me later that for the first three guys all she could do was to try to hang on as it felt like they were ripping her ass open and she had to just get through the pain. Somewhere towards the end of the third ass fuck she said that her ass must have gotten used to the size because she started to feel a tingle in her pussy. She said that she was also able to press her pelvis against the bench a little and this increased the pressure and sensation on her clit.
Half way through the fourth ass fuck Jennifer had her first orgasm. We could hear her moans even around the cock in her mouth and saw her body and legs tense up as she came. That opened the floodgates because Jennifer told me that she came at least once with each of the next three guys that fucked her ass.
Jennifer now had eight loads of cum in her ass and needed only to take one more guy before she would win our bet. The ninth guy would not be easy however.
The ninth guy had the biggest cock of the crew, he later told us it measured nine and a quarter inches and it was thick, not coke can thick but thicker than any cock anyone had seen other than in porn flicks. Even Ron Jeremy only beat this guy by a half of an inch.
He stepped up behind Jennifer, took aim and thrust his way into her ass. Jennifer's mouth was not occupied and she shrieked in pain. "Take it out, it's too big," she cried but he continued to push in to the hilt. He then started to pull out and Jennifer gnashed her teeth and said that she thought he was pulling her guts out. He pushed in again, faster this time and Jennifer yelled, "Yellow, yellow."
The guy stopped but did not pull out and gave Jennifer the thirty second break she was entitled to. He started to again fuck Jennifer's ass and she continued to beg him to take it easy but he was picking up the pace.
"Yellow, yellow," Jennifer yelled again.
The guy stopped and gave her another break and Paul came over and reminded Jennifer that she had used up her slow words.
Jennifer was panting trying to get used to the fullness in her ass and I tried to imagine what it would have been like if she had not already had eight guys to loosen up her ass before this monster pushed its way into her.
The time for the break was over and the guy said, "Hang on honey, the next time I stop is after I come in your little white ass."
The guy really started to let Jennifer have it and she continued to yelp and beg. One of the other guys got in front of Jennifer and was going to put his cock in her mouth to quiet her but the guy fucking her as waved him off saying, "Don't give her anything to take her mind off of what is happening to her ass."
With her mouth empty Jennifer continued to be vocal and the huge cock continued to fuck her ass hard. Somewhere along the way the pressure in Jennifer's ass must have gotten through to her clit because her cries started to turn to moans of pleasure. Even strapped down as she was we could see her valiantly try to raise her ass up to get more of the monster cock into her nether passage.
She continued to pant and moan and then on one particularly hard thrust Jennifer yelled, "Oh, God, I'm cumming," and exploded into an impressive orgasm. She was silent for a few seconds as the guy continued to piston his cock in and out of her ass and then yelled, "Shit, I'm cumming again."
The guy wrested three more orgasms from her before he finally blew his load into her ass.
Jennifer had made it, she had taken nine guys in her ass to win our bet but Paul and one other guy had not yet used her ass and the deal was that she would take the whole crew. By this point Jennifer was exhausted and did little more than moan softly as Paul and the last guy took their turn at her ass.
After the last guy had dumped his load Paul came over and gently ran his hand through Jennifer's hair. He said, "We are going to give you a little break to get cleaned up but remember we have you until 1AM."
Jennifer looked at the clock behind the bar and saw that it was just ten thirty. She had been getting her ass fucked for nearly two and a half hours. She also knew that she had a couple of hours more to go.
Paul and another guy undid the straps holding Jennifer to the bench and helped her to her feet. Her ass still gaped open and when she stood up a large dollop of cum came out and rolled down the inside of her right thigh. Paul held her up as she got her bearings and when she had steadied herself Jennifer walked through the club and into the changing room the club had off of the lobby. The changing room had a shower and a toilet and Jennifer said the first thing she did was to sit down on the toilet and let the cum flow out of her ass. She said that she could not believe how much cum came out of her.
Jennifer then took a shower and bushed her hair and otherwise made herself as presentable as possible. She put her heels back on and walked back out to where we were all waiting. The clock said ten fifty and after glancing at it for a few seconds Jennifer walked over to the bench and positioned herself to be strapped down again. You gotta give that woman credit, she is certainly game.
Two of the other guys did the honors and Jennifer was again soon immobilized. The fucking started again and Jennifer took on the crew a second time but this time they mostly came in her mouth and pussy. A couple of them had a third go at her.
Six of the guys fucked her ass a second time despite her pleas to, "Please use my pussy," making a total of seventeen ass fucks on the night.
At a minute to one in the morning Jennifer took two more loads, one in her pussy and the other in her mouth. We let her remain tethered to the bench for a while as the sperm oozed out of her ass and pussy and ran down her legs. There were also globs of cum on her face and in her hair.
The straps were unfastened once again and Jennifer went to clean up for a second time.
About 20 minutes later Jennifer came back in to the main room and asked for a drink. One of the guys prepared it for her and we all toasted to a fun evening.
A few of the guys had gotten dressed and left but many of those who remained were still naked as was Jennifer but as she had no clothes to put on she really did not have any choice. Eventually Jennifer wound up talking with the guy with the huge cock who was the ninth to fuck her ass. I could see her casting furtive glances at his tool which hung limply between his legs. Even soft it was an impressive specimen.
They continued to chat for a while and eventually Jennifer reached down and started to stroke his cock. It started to spring to life and the guy, whose name was Jayson, said, "Don't start what you won't finish."
Jennifer continued to stroke his cock and got down on her knees and took the head in her mouth. She took another inch or two but that was it. The cock was just too wide to fit into her throat.
After a few minutes of licking and stroking his cock Jennifer had it fully erect. She stood up and said, "I must be crazy for doing this but I never came as hard from a cock in my ass as I did when you fucked me the first time with it. My ass is sore from all of the fucking I did earlier tonight but I just have to feel that cock in my ass once more."
Jennifer then took Jayson by the hand and led him over to the bench. She draped herself over it and when two of the other guys started to put the straps on her she said, "I won't need those."
The guy who was about to fuck her ass said, "Yes, you will. Remember the first time when you used your slow word twice and screamed and begged and pleaded before you got used to it. I told you if you started you would finish and the way to make sure is to strap you down."
Jennifer said, "OK, if that's what you think."
"It ain't what I think, it's what I know. I have only found one lady in my whole life that has been able to take me in her ass without a lot of hollering and screaming at least at the beginning. People think having a huge cock would be great but it's a mixed bag because even though I can make women come hard with it there are a fair number of women who just cJenniferot take it in either their ass or pussy or who see it and freak out without even trying."
Jayson nodded to the two guys who had started to put the straps on Jennifer and they got back to work. They secured her legs to the side of the bench, locked her hands in the cuffs and put the straps across her waist and shoulders. They stepped away when they were done.
Jayson picked up the tube of lube and forced a dollop into Jennifer's ass. He used first one then finally three fingers as he stretched the tight ring of her ass. Her ass yielded easily to his invasion because Jennifer was still a bit loose from the night's earlier activities but she was not loose enough to take something as big as his cock easily.
"OK, baby, here we go," Jayson said and started to push his cock into Jennifer's ass.
"Aieeeeeeeeeeeeee," Jennifer shrieked as it popped through her anal ring.
Jayson pushed forward and in to the hilt and Jennifer kept shrieking in pain. "I changed my mind," she sputtered, "Take it out."
"Sorry sweetheart, I told you if we started that we would finish and that's what we're going to do."
"Noooooooo," Jennifer yelled, "It feels even bigger than it did the first time."
"That's cuz the first time the eight other guys had loosened up your ass and it's just closed up some since then but I will take care of that," Jayson said as he gave Jennifer a couple of strokes.
Jayson again pushed in to the hilt and Jennifer raised her head a bit and said, "Oh, it feels like it is going to come out of my throat."
Jayson started to pull out and Jennifer kept blustering and protesting and yelling. Jayson stopped and said, "Your getting exactly what you asked for so shut up and take it," and he slapped Jennifer's butt hard with his right hand.
"Eeeeowwww," Jennifer yelled. In just seconds you could see the handprint on her butt from where he had spanked her.
Jayson brought his hard down even harder on Jennifer's butt twice more and said, "Either way you are getting your ass fucked. It can be with a spanking or without one. I am going to keep spanking you as long as you keep yelling."
"But it hurts," Jennifer wailed and Jayson gave her two more hard spanks. You could now see several fiery red hand prints on her pale white butt.
Jayson had his hand up ready to give Jennifer another spank when Jennifer said, "Enough, I'll be quiet."
Jennifer was true to her word and although she continued to sob softly you could see her biting her lower lip obviously trying to muffle the sounds.
Jayson started to piston his huge member in and out of Jennifer's ass and although she continued to grunt and moan it was clear that she had decided that whatever the pain of her ass fucking she was going to do what she could stay quiet enough to keep him from further blistering her butt.
He continued to fuck her ass hard for a few more minutes and then said, "That's it baby, now you're getting into it," and we could see Jennifer almost imperceptibly moving her butt back a little to meet his thrusts. With the straps she could not move that much anyway but she was moving as much as the straps allowed.
Just like the first time, we could also hear that her moans of pain were becoming moans of pleasure.
Jayson continued to fuck her ass and Jennifer did what she could to help the process. Because Jayson had already cum twice this evening he had very good stamina and Jennifer's ass took a real pounding.
Stroke after stroke went in to the hilt and we could see a sheen of perspiration forming on Jennifer's body as she got close and closer to orgasm. As one particularly hard stroke hit its mark Jennifer screamed, "I'm coming you fucker."
Jayson stopped thrusting for a moment and let Jennifer just cum on his cock that was buried fully in her ass. A few strokes later Jennifer yelled, "Fuck, I'm coming again."
Jennifer came twice more before Jayson finally reached the end of his stamina. His last couple of strokes were so hard that the bench actually moved forward an inch or two on each. "Here it comes baby," he moaned as he dumped his load into Jennifer's ass.
He stayed planted in her ass for a couple of moments and then pulled out with a loud pop. Jayson walked around to the front of the bench and put his cock in front of Jennifer's mouth. "Clean me up," he said.
I thought Jennifer was going to freak out as she had never done ATM before but she just opened her mouth and started to suck and lick him clean. She later told me that she was still on such a high from how hard and often she had come that she would have done anything he had told her to do.
Watching Jayson ass fuck Jennifer had gotten three of the guys who were left hard and they approached the bench. When Jennifer saw the hard cocks jutting from their bodies she said, "Oh God, just please do not fuck my ass."
Jennifer could do little more than mewl softly as they took turns fucking her pussy. She later told me that she felt like she was floating in and out as they fucked her cunt and although she did not come she said it was pleasurable.
Seeing no more hard dicks in the room Paul walked over to the bench and said, "Congratulations, you have fucked out everyone in the room," and he loosened the straps and helped Jennifer to her feet.
She went to clean up for a third time and while she was doing that the rest of the crew left leaving only Paul and I waiting for her.
When she came out she was carrying a T-shirt that she had found in a box in the changing room. It was new and had the name of the sex club on it along with some other promo type stuff.
Can I wear this?" Jennifer asked.
"Sure," Paul said and Jennifer slipped it over her head.
She almost looked sexier with it on than she did naked because it fit her fairly tightly which caused her still hard nipples to clearly jut out in the front. It was only long enough to reach part way down her butt and her pussy peeked out invitingly.
"I will drive you home," Paul said, "We can get your car back to you tomorrow from my place."
Jennifer and I were no sooner in our front door when she took me in her arms and said, "There is just one more cock I want in my ass tonight."
We were naked in what seemed like only seconds and I bent her over the back of one of the chairs in our living room. I did not need lube as her ass was still slick from before.
We fucked hard for a few minutes before we both came just about simultaneously. I held Jennifer for a few minutes as my cock softened.
Jennifer led the way upstairs and I could not help but marvel at how sexy her ass looked as she walked up the steps in front of me or how sexy it had looked getting fucked by Paul's crew.
When we got to the top of the steps Jennifer turned around and greeted me with a kiss and said, "I hope my new car has soft seats because my ass is going to need them for a while."
My wife and I were monogamous for several years after we married but then even though we still loved each other intensely our sex lives had become routine and stale. We each craved the excitement that came with having sex with someone new. The different touch, the different sounds, the different taste. Because we were always open with each other we talked about our feelings and eventually concluded that the answer was to open our relationship to other sex partners and have done so for the past umpteen years. Having such an open relationship has allowed us to maintain a special relationship between us as a couple while at the same time being able to enjoy a variety of other sex partners.
I guess over those years my wife, her name is Jennifer, has gotten the better of the bargain. Like many women who are in an open relationship she has had a multitude of sex partners, more than I, largely because women have the advantage of being able to fuck for as long as they want to while we men can only cum a few times before we are done for the night.
We always practice safe sex with our other partners and we do not have intercourse, whether vaginal or anal, without a condom except when we have written proof that our partners have been tested.
Before moving on, let me describe Jennifer. She is 5'2" tall and weighs 115 pounds. She has brown eyes and medium length brown hair that at times looks reddish in certain light. Her skin is very pale and she has a lot of reddish freckles on her tits and shoulders. Her breasts are a natural B cup topped with light brown/pinkish nipples which get about a half an inch long when she is aroused. Her nipples never get fully soft so if she goes braless you can usually get a glimpse of her nubs through her top. Jennifer has a very, very thin waist which gives her a classic hourglass figure and an ass to die for. We never had children so Jennifer's pussy is nice and tight.
My wife is also very competitive and into sports like football and we often argue about which team will win a particular sporting event. Over the years we have made many bets against each other for various stakes, both sexual and non-sexual. Jennifer knows sports better than most guys I hang out with and her bets are well thought out. It is this betting that led us to where we are for this story.
We were cleaning up after a poker game at our house when I sat down at the table, started to shuffle the cards loudly against the table and said, "One hand, winner takes all."
"What's all?" Jennifer asked as she walked over towards where I was sitting.
"If you win I will buy you that necklace we looked at yesterday," I said.
"And if you win?" Jennifer inquired.
"If I win, you cut the cards and have to have sex with the number of men that is equal to the number on the card you drew," I told her as I continued to shuffle the deck.
"What if I draw a picture card?" Jennifer asked.
"Aces count as one and then the suits go up to 13 for the kings and to make it more interesting let's say that hearts mean you have to fuck the guys, diamonds mean blow jobs, clubs mean anal and spades mean all three," I said.
"Wow, pretty specific aren't we," Jennifer said, "You must have stayed up late thinking all of that out."
Actually I don't know where that idea came from, whether I read it somewhere or it just popped into my perverted mind.
Jennifer pulled out a chair and sat down across from me at the table. "Deal," she said.
"Five card draw," I Jennifer announced as I dealt each of us five cards.
The game went very quickly because there was no betting as the stakes had already been set. The end result was that I would up with a pair of aces which beat Jennifer's pair of nines.
I collected up the used cards and put them back into the deck, shuffled it a few times and placed it in front of Jennifer.
She looked over at me for a moment and said, "Well here goes nothing," and cut the deck about half way down. Jennifer turned over the top half of the deck and we both saw that she had drawn a five of hearts. That meant that she would have to fuck five guys.
We both realized that we had not been specific enough in setting up the rules as one glaring omission was how long Jennifer had to perform her task. We talked about it and decided that it would be fair to give her until the next poker night at our house which was four weeks away.
As Jennifer and I had been in an open relationship for several years she really did not have any trouble hooking up with five guys and getting fucked by each of them. In fact, she had finished with the fifth guy and still had a few days to go before the date of my next poker game.
The night of the next poker game came and my four friends showed up as usual. We had been playing for years and wanted to keep the game friendly so we agreed early on that we would quit at midnight so no one felt pressured to keep playing and that we would each buy in for $50 to start the night. When your $50 was gone you were busted and done for the night. Jennifer went out with a girlfriend of hers to a movie or something and got home just as the last guy was leaving.
She walked over to the poker table, picked up the deck and said, "Do I get a re-match?"
"Of course," I said and we agreed on the same stakes as before.
Another quick game except that this time Jennifer won and I got her the necklace the next day.
Same story the following month and Jennifer had a pair of matching earrings to go with the necklace.
Each time we played the game we thought of another aspect of the rules that we had not covered so as time went on the rules got more and more detailed and specific. For example, we added a forfeit that Jennifer would have to do if she lost and was not able to perform all of her tasks in the allotted four weeks. We also added two jokers to the deck and if Jennifer drew a joker she would take the next card and double it. The stakes also increased as well in terms of what Jennifer got if she won.
Eventually over time we dispensed with the card game between us and got to the current set of rules which were as follows:
1) Jennifer would draw one card from the deck on the first day of the month. The value of the card would be the number of guys she had to have in the coming month. If Jennifer drew a joker she would take the next card and double it. Once a card was drawn it would not be replaced in the deck.
2) Aces would be ones going up to 13 for kings. Hearts meant she had to fuck the guys, diamonds were for blow jobs, clubs were for anal and spades meant all three.
3) A guy counted against the goal if Jennifer got him to come in her mouth, ass or pussy, as applicable. In the case of hearts, diamonds and clubs, Jennifer could do more with the guy than the required activity but it was her choice.
4) A guy could only count once in any given month and I did not count.
5) In the case of spades for a guy to count Jennifer had to get him to come in each of her openings or he would not count. Because not all guys can come three times in a single session the three times could be over more than one session.
6) Jennifer could take the guys on individually or in whatever groups she wanted but no more than a third of the guys could be at a single session at a sex club and there could be only one sex club session in a month.
7) The game would run for eight periods of six months each (leaving four cards that would not be drawn) with a new prize and forfeit at stake in each.
8) Jennifer had one put back in each period where she could draw a card and if she did not like it she could put it back in the deck and draw again.
9) Jennifer was allowed one "do over" each period if she missed her goal in any one month but she would have to add five to the goal she had missed.
We went back and forth about these rules for a while until we were in agreement and decided that the game would start the first of the coming month. All we had to do now was to come up with the prize and the forfeit.
Jennifer said that she wanted a new car, specifically, a Mini Cooper Convertible, and I breathed a sigh of relief because when I heard "new car" I was thinking "Mercedes" or "BMW" would be the words that followed.
For the forfeit I told Jennifer that she would have to have her nipples and clit pierced. She blanched and tried to talk me out of it until I challenged her saying, "Well if you are chickening out then I suppose we will just not play the game."
I knew that her competitive side would not let her walk away from a challenge even though she dreaded the forfeit.
I was right as Jennifer quickly said, "I am not chickening out. Just keep your checkbook handy because you will need it at the car dealer."
A couple of days later the first of the month arrived and I got a new deck of cards out of the cabinet where I kept the poker chips and other assorted paraphernalia. I unwrapped the box and took out the cards.
Jennifer came over and sat down next to me and watched as I checked to make sure the deck had all 52 cards plus two jokers in it. Once I had verified that the deck was complete I started to shuffle it and did so for a couple of minutes to be sure the cards were well mixed. As with any new deck the cards came arranged by suit from low to high and I wanted to be sure that the cards would be in the deck randomly.
I finished shuffling and then laid the deck in front of Jennifer and said, "All yours."
Jennifer looked at the cards for a moment and then at me and smiled. She reached for the deck took it in her left hand and then fJennifered out the cards. She thought for a moment and then picked a card about two thirds of the way in. Jennifer turned the card over and we both saw that it was a four of hearts.
"Piece of cake," Jennifer said.
I knew she was right because with our swinging/swapping it would not be a problem for her to fuck four guys during the next month. It wasn't. Nor was it a problem for Jennifer the next two months as she drew a six of diamonds and a three of clubs.
With Jennifer drawing so many low cards I was beginning to think that she should audition for Deal or No Deal but I knew that the deck was still filled with high cards and that no spades had been drawn as yet.
In month four her luck ran out and she drew a jack of diamonds. We both knew that even with our regular swapping partners Jennifer would have to hustle up a couple of more cocks to suck in order to get to eleven for the month.
Jennifer solved the problem by going to one of the swing clubs we go to from time to time. She dressed up in a garter and hose with CFM heels and put a raincoat over that so from the time she checked her coat at the club all of her assets were clearly on display. She used a bright red lip gloss which highlighted her luscious lips.
After her swapping partners and two other guys she picked up she needed only three more guys for the month and needless to say she did not have trouble attracting enough men at the club to put her over the top for the month. Jennifer looked so hot dressed (or undressed actually) the way she was and with her on her knees sucking loudly on a guy standing in front of her it did not take long for a small line of guys to form hoping that she would service them as well.
But that was not Jennifer's style and after the third guy she got up, smiled at the guys waiting and said, "Maybe later."
For whatever reason despite her having had numerous partners and participating in several gang bangs with up to six guys Jennifer was not into scenes where she would service one guy after another after another. She said that although she knew that all of her extramarital activities definitely made her a slut that a woman who just serviced a line of guys was a cum dump and she did not want to be a cum dump. I thought that the distinction was pretty nuanced but for Jennifer it was important so I never made an issue of it although like with anything you do not have I did want to see her be a cum dump at least once.
Month five saw Jennifer's luck return and she drew a two of hearts. As I said, put this woman on Deal or No Deal.
Month six yielded the nine of clubs and I thought that there would soon be a new car in Jennifer's side of the garage but Jennifer procrastinated and let things go. With a few days left in the month she was still a couple of guys short when we got a call that her sister had been in an automobile accident. Jennifer left immediately to be with her sister and could not really do anything sexually while she was there and ran out of time.
"I get a do over if I need it, right," Jennifer asked me on one of our phone calls.
"Yes, you do but you have to add five to the number so that makes it 14," I replied.
"Can we postpone things a month because I have to stay with my sister another few weeks?" she asked.
"Sorry, there is nothing in the rules about time outs so you are on the clock as of right now."
Jennifer whined and moaned about that being unfair but I would not yield. I finally saw the opportunity to win and have her do the forfeit of having her nipples and clit pierced.
When we started this bet and negotiated the rules I thought it would be harder for Jennifer to find enough guys when the cards got high especially if they were spades and since she had to go six for seven (counting one do over) to win I thought the odds were in my favor. I guess I totally underestimated how easy it would be for an attractive woman to get guys to have sex with her. I was also counting on some spades being drawn but they were all still hiding somewhere in the deck.
Anyway, Jennifer did not get back home until there was only a week left in the month and she got to work getting her ass fucked. She connected with several guys from our swing group but several others were out of town because it was the summer. Our two regular sex clubs were also closed, one for renovations and one while the owners took their summer vacation. Jennifer was clearly running out of time and options.
With only four days left in the month Jennifer said to me, "I'm going to talk to Paul."
"Are you sure you want to do that?" I asked.
"I really have no other choice unless I want to see my nipples and clit pierced."
Paul was a good looking black guy we met at one of the sex clubs we frequented. He was also a dominant who trained women to be slaves. He also put on a bdsm show a couple of times a year at the club. He had hit on Jennifer wanting her to do a bsdm scene with him but she had always turned him down although she did let him fuck her once.
Paul was also part of an all black gang bang crew that offered their services on the internet to women who wanted to be banged by a group of black men. The guys were all tested regularly for STDs, well endowed and offered a safe experience for interested women and couples.
We both knew that there would be a price for Jennifer to pay for Paul's help and that price would include submitting to him.
Jennifer got up off of the couch, walked into our home office and closed the door. I could hear her talking on the phone for a few minutes but could not make out what she was saying.
The office door opened and Jennifer walked out and went over to the bar, got a glass from the shelf, dropped some ice in it and filled it almost to the top with some of our best scotch. I could see her hands tremble as she raised it to her lips.
"What did he say?" I asked.
"Paul said he would arrange it but that he had some conditions," she replied.
"His conditions are that I take on the full crew one after the other and that I be restrained during the process. The crew will also be allowed to fuck my mouth and pussy after they have fucked my ass. He will give me a safe word and a slow word to use if things get too intense and I have to participate in his next bdsm scene at the club," Jennifer related.
Jennifer continued, "He said that he would get at least nine guys to be there including him (nine was the number Jennifer needed to get to her revised monthly goal) but if he got more I would have to take them all up to 14. He said that because all of the guys would be currently tested no condoms would be used."
I could see now why her hands were shaking as she again raised the drink to her lips.
"So what did you tell him?" I asked.
"That I would think it over and let him know before noon tomorrow."
Jennifer spent a restless night and I could feel her tossing and turning on the bed next to me. She looked tired the next morning at breakfast and as I read the paper while nibbling on a muffin she quietly said, "I'm going to do it."
I looked over at her and nodded.
"What Paul and his crew are going to do to me scares me but I am more scared of the pain of having my nipples pierced and especially my clit because you know how sensitive it is," Jennifer said.
We left for work and Jennifer called Paul on her cell shortly before lunch.
He told her that he would set things up for Saturday night and that we should come over to his place around 4PM so that he could prepare her. He told Jennifer that she was to shave so that she had no hair anywhere on her body other than her head. She was to wear only heels and a trench coat.
Jennifer spent most of the day Saturday getting ready and really looked hot. Her skin was smooth and hairless and glistened with the lotion she had put on herself. I walked over to where she was standing in front of the mirror and ran my hands over her body. I rubbed her right breast with one of my hands and my other hand slid down to her pussy. When I started to finger her I was amazed at how wet she was. She moaned as I slipped one then two fingers into her.
"Hmmm, the thought of being ass fucked by Paul and his crew must be turning you on," I said.
Jennifer replied, "I am still scared because I know that all of the guys will be hung as I looked at their website and I hate the thought of being restrained and being a cum dump but somehow that fear and trepidation has turned me on something fierce."
I continued to finger Jennifer for a few moments and she started to hump her pussy back onto my fingers. A few moments more and she had what she later told me was her third orgasm of the day.
Jennifer finished her makeup and put on her black CFM heels. She walked over to the foyer closet, took her trench coat, put it on and said, "Let's go, before I change my mind."
We did not speak during the five minute ride to where Paul lived and I parked a few doors down from his house. We got out of the car and I had to hurry to keep up with Jennifer who was walking fast because she said she felt very conspicuous wearing CFM heels and a trench coat in the middle of a nice summer day.
We walked up to the door and I rang the bell. Paul opened the door a few seconds later and shook my hand. He looked over at Jennifer and said, "Lose the coat before you come in."
Jennifer looked around nervously to see if anyone was going to see her ****** herself. She opened the belt on her coat, slipped it off her shoulders and handed it to me. I could not believe how incredibly sexy she looked standing there naked except for a pair of CFM heels. The vision did not last long as Jennifer turned and walked into Paul's house.
Paul was waiting just inside the door and said to Jennifer, "Kneel." She was startled and after a few seconds dropped to her knees. "Spread your knees wider," Paul said and Jennifer slid her knees further apart ******** her pussy even more. Paul walked over and stood in front of Jennifer.
"OK, here is how it is going to go. From here on out you are to do what I or the guys in my crew say. If you want to quit, your safe word is 'red.' If you say 'red' whatever is happening to you will stop and you will be free to go. Tomorrow morning your husband will take you to have your nipples and clit pierced," Paul said.
"Your slow word is 'yellow' and if at any time things get too intense you can stop the action for thirty seconds by using your slow word. You will be allowed to use the slow word twice," he continued.
Paul finished by saying that from then on Jennifer was to address him and any member of his crew as "Sir," and to do what they said without question or hesitation
"Do you understand what I just told you, Paul asked.
"Yes," Jennifer meekly replied.
Paul reached out and took Jennifer's left nipple in his fingers, squeezed it hard and twisted it saying, "Yes what?"
Jennifer cried out at the abuse of her nipple and quickly said, "Yes, sir."
"Very well then," Paul said, "Let's get started."
Paul turned and started to walk away and said to Jennifer, "Follow me."
Jennifer obediently followed Paul down the hall. He led her into his master bathroom and she gasped when she saw the enema bag hanging from the wall. Jennifer later told me that she did not know what to expect when Paul said he was going to prepare her and thought he would just fuck or otherwise use her before taking her to wherever her anal gangbang was going to take place.
"Over here," Paul said as he motioned to a spot on one of the rugs.
Jennifer walked over and stopped. "Get down on your hands and knees," Paul said. Once Jennifer was on the floor Paul pushed her shoulders down and positioned her so that her ass was sticking up in the air.
"Spread your cheeks and show me what we are going to be fucking tonight," Paul said.
Jennifer slowly reached behind and pulled her ass cheeks apart. My heart skipped when I saw how lewd she looked with her ass open and ******* the way it was.
Paul saw me looking and said, "Take a good look because her little asshole is not going to be that little when we are done with it."
Paul then got a tubular metal bar from the countertop that had four leather cuffs attached to it. He took the bar and put Jennifer's ankles into the outer cuffs and locked them in place. He told Jennifer to put her hands through her legs and he then cuffed her wrists to the inner two cuffs. She was now fully restrained and had no choice but to remain in her ass up humiliating position.
But Jennifer did not as yet appreciate how humiliating things were going to get.
Paul then took a tube of lube and greased up Jennifer's ass forcing first one then two of his long fingers into her nether hole. Jennifer grunted at the invasion.
Satisfied that her ass was sufficiently lubed Paul then took a double balloon bardex nozzle off of the counter. I could see Jennifer's eyes widen as she had never seen one before. Paul saw the look on her face and said as he held it in front of her, "The larger balloon goes inside of you and then we inflate both. Once they are inflated whatever solution I put inside of you will stay there for as long as I want it to."
While he was saying this he inflated both balloons and Jennifer whined when she saw and understood what would soon be inside of her.
Paul deflated the balloons and got behind Jennifer. He slowly forced the larger balloon into her ass and when it was seated properly he closed the valve and began to pump the bulb. Jennifer was silent for the first two pumps but said "oh" with each of the last three pumps as she felt the balloon expand. Paul then closed the valve on the outer balloon and then pumped it to its maximum. Jennifer groaned as the two balloons tightened towards each other effectively sealing her up.
Quickly Paul stood up and got the hose and connected it to the nozzle. When he was satisfied everything was tight he said to Jennifer, "Try and relax as much as possible, you are going to feel very full."
He then opened the valve and the solution began to flow into Jennifer. She grunted when she felt the first blast of the warm solution flowing into her bowels and as the flow continued she started to groan. Because of her ass up position the flow was unimpeded and she started to fill up quickly.
We could see that she was getting uncomfortable and Jennifer started to beg and plead with Paul saying, "Please, Sir, no more. I cJenniferot take any more."
"Actually you are only about half way and there is still over a quart to go," Paul said.
"Noooooooo," Jennifer whined and pleaded even louder.
Paul stopped the flow for a moment and said to Jennifer, "You can always use your safe word. I talked with your husband and he is in a no lose situation. If you go through with the black anal gangbang he gets to watch and see you used as a cum dump. If you use your safe word he gets to have your nipples and clit pierced. I also win because regardless of what happens you are going to do a bdsm scene with me at the club later this year."
I knew that Jennifer realized what her two alternatives were but when Paul explained them to her this way I think she really understood how bleak her two choices were.
"OK, here we go again," Paul said and he opened the valve again.
Jennifer immediately grunted and kept grunting and moaning as her bowels filled to capacity. She did not beg or plead however so she must have decided that going through with her anal gangbang was the better alternative.
We finally heard the sound of the bag reaching empty. Paul shut the valve on the hose and said, "Now we will just leave that inside of you for a few minutes."
He and I went into the kitchen to get a beer and left Jennifer in the bathroom. Jennifer later told me that she felt very uncomfortable as she was cramping almost constantly and felt incredibly full. She also felt totally humiliated being restrained as she was with the bardex nozzle sticking out of her ass.
Paul and I finished our beers and we returned to the bathroom.
He walked over behind Jennifer and released her hands from the cuffs and then did the same to her ankles. He helped her to her feet and then showed her how to release the air in the balloons and then said, "We will give you some privacy for this part. Wash up the nozzle and shower when you are done."
We walked out of the bathroom and closed the door behind us.
Paul and I were on our third beer when Jennifer finally walked into the kitchen. She was naked except for her black CFM heels.
"How do you feel, Jennifer," Paul asked.
"Exhausted," Jennifer said and then as Paul reached for her nipples, "Exhausted, Sir."
"Well, you may want to have a drink in any case," Paul said and Jennifer asked for a vodka tonic.
After another round Paul looked at his watch and said, "We better get going."
Jennifer thought that we were leaving and said, "What about my coat, Sir?"
Paul said, "We're not leaving yet. We are going to go into the bathroom for your rinse. We want you nice and clean because the boys are all tested and do not have to use condoms some of them may want to go from your ass to your mouth."
Jennifer shuddered at these words and I thought she may call a halt to things but she somehow held herself together.
Jennifer later told me that she decided to try to get through the anal gangbang by getting through each step one step at a time. She said that what was most disconcerting was when Paul threw another unexpected step into the process which he did more than once.
About half an hour later Jennifer padded into the kitchen. She was naked except for her CFM heels. I was actually surprised that she had remembered to put them on but this woman continued to amaze me with her toughness and resiliency.
Paul had a vodka tonic ready for her and she shakily brought it to her lips. You could tell that Jennifer had a rough couple of hours and we all knew that more tough times lie ahead.
Jennifer came over and sat down next to me and I put my arm around her shoulder and idly fingered her right nipple. It hardened almost immediately and I knew that despite everything that had been done to her Jennifer was still smoldering under the surface.
We sat and talked for a while and then Paul looked at his watch and said that it was time to go. I asked where we were going and he said that he had arranged with the owners of the sex club that was closed for their vacation to use it. Jennifer immediately perked up and asked me if the rule about only a third of the goal being able to be satisfied at a single session at a sex club would apply and I said that it was a technicality about whether it applied since the club was closed and that I would give her the benefit of the doubt and waive that rule for tonight.
Jennifer appeared to like my answer and finished her drink.
Paul got his car keys and said that he would drive and opened the door down to his garage. Jennifer got up and walked down the stairs to his car never once asking if she would be allowed to wear any clothes. As I said, an amazing woman.
Paul put Jennifer into the passenger seat in the front and we were off. She just sat there calmly even when he reached over and parted her legs so that a trucker that had stopped next to us at a traffic light could get a better look.
It was almost as though Jennifer had decided that since she was off to have nearly a dozen black guys fuck her in the ass what difference did it really make if some truck driver saw her naked.
As we got closer to the club Jennifer's demeanor changed from the confident to the less so. She reached her hand to the back seat and took my hand in hers and held on tight. I could tell she was thinking and worrying about what was going to happen to her when we got to our destination.
We got to the club and Paul pulled into the parking lot and stopped the car. I got out and opened the door on Jennifer's side and she stepped out without hesitation, took my hand and walked towards the door. Naked as the day she was born except for her heels Jennifer walked deliberately across the parking lot to meet her gang bang crew.
Paul opened the door to the club and stepped inside. Jennifer and I followed. It took us a few minutes to get used to the darkness and then we moved to the middle of the club. Jennifer could hear approving voices as the members of the crew saw her naked body stroll into the center of the club.
Paul raised his hand and the voices stopped. He said, "Let me introduce you to Jennifer our gangbang anal slut for this evening," and he gestured towards Jennifer. I could see Jennifer shudder at his words as if the reality of what she had agreed to do had finally fully hit her.
Jennifer looked over at the bar area and saw ten guys standing around in several small groups. Including Paul that meant that her gang bang crew would be a total of eleven.
All of the guys were black with skin tones ranging from the lighter to the truly black. All appeared to be in shape and ranged from about 5' 10" up to around 6' 4" in height. You could tell that all of them were looking forward to fucking Jennifer in the ass and possibly in her mouth and pussy.
Paul then explained the bet that Jennifer and I had made and said that Jennifer had to have at least nine guys cum in her ass for her to win and get her new car. If she failed for any reason she would have to have her nipples and clit pierced. Hearing this the guys realized that they would not have to hold back and you could hear comments like, "We are going to tear up that tight white ass."
"Jennifer has two safe words," Paul said. "The word 'yellow' means that whatever is happening stops and she gets a thirty second break and 'red' means that the whole scene stops. Jennifer can use the slow word twice," he continued.
"Once the scene starts Jennifer has to do everything she is told by any of us and her only way out is to either finish the scene or use her stop word. The scene starts now and Jennifer is ours until one in the morning," Paul said.
I glanced at the clock behind the bar and saw that it was just 8PM. Jennifer was going to have a tough five hours.
Jennifer knew from talking with Paul and looking at his crew's web site that all of the guys were hung, a solid seven or eight inches with a few almost nine and very thick. The guys also all had great stamina and could fuck long and hard. We also learned later than many of them took Viagra or one of the other ED drugs before scenes like this. Those drugs in younger guys had the effect of making their erections even larger due to the increased blood flow and allowed them to get hard again sooner. Apparently those drugs have become popular in the porn industry for those reasons.
The guys started to strip and soon a group of four of them surrounded Jennifer. Even in her 4" heels the guys dwarfed her and she looked so tiny and vulnerable standing among them. The contrast of her pale white skin against their darker complexions was also stunning.
In seconds, Jennifer had hands all over her body and her tits, ass and pussy were getting mauled. Fingers probed her two lower openings and she bucked and writhed at the invasions.
Soon she was pushed down to her knees and presented with a large cock to suck. As she took it into her mouth its owner said, "We didn't get a fluffer so you are going to have to do the work and get us nice and hard so we can fuck your pretty white ass and pussy."
Jennifer struggled to get the cock into her mouth as the guy pushed deeper and tried to get into her throat. He could only get part way in but it was enough to block Jennifer's ability to breath through her mouth and she was soon sputtering from her nose trying to get her breath.
The guy sawed in and out of her mouth for a few minutes and then another guy took his place followed by another and another.
Paul then stepped in and helped Jennifer to her feet saying, "Time to get you set up."
He led Jennifer over to a padded bench and when she saw it Jennifer knew that she was looking at the place of her defilement. She knew that she would be tethered there for the rest of the night and used and abused with her safe words her only escape.
Paul adjusted the bench so that it was about waist high and then bent Jennifer down over it. "It's cold," Jennifer said as her tits touched the flat part of the bench. "Don't worry," Paul said, "You will be warm soon enough."
The bench had a slight downward angle so that Jennifer's head was a bit lower than her butt. Two of the other guys started to strap Jennifer to the bench. They put cuffs on her ankles and chained her legs wide apart. Larger cuff connected to another set of chains were put just above her knees further insuring that Jennifer would not be able to close her legs. Another pair of straps was put over her waist and shoulders securing her torso to the bench. Finally, Jennifer's hands were pulled out to either side and secured with wrist cuffs.
Jennifer's head hung over the front of the table but not for long. Paul came around and got a U shaped device that was padded with the same material as the table and slid it into a slot at the front of the table. He adjusted the sides so that they pressed against the sides of Jennifer's head thus immobilizing her head as well and putting her mouth at the perfect angle to service the many cocks that would soon be pushing down her throat.
When I looked at Jennifer's face I could see her eyes wide with fear but as I looked closer I thought I also saw some lust in her eyes. Jennifer later told me that she had a multitude of feelings as she was being secured to the bench ranging from fear that morphed into more and more lust as each strap was put into place and she was secured for her night of service. She said that although she never wanted to be a cum dump she began to understand what women who were had experienced as they waited for their body to begin to be used by man after man.
Paul went around behind Jennifer and started to lube up her ass. You could hear Jennifer grunt as he forced first one, then two and finally three of his fingers into her little puckered hole. "Three fingers are small compared to what is soon going to be in your ass," Paul said as he withdrew his fingers from Jennifer's ass.
Jennifer was definitely no stranger to anal sex but she had only had one or two really big cocks in her ass and now she was strapped down with a room full of very well hung guys lining up to fuck her ass.
The first guy, who was still hard from Jennifer sucking him earlier, stepped up behind Jennifer, lined his cock up with her ass and drove it in to the hilt in one strong push. "Arrrrrgh," Jennifer yelled and begged him to start slowly. Her pleas were ignored as the guy started to fuck her ass hard right from the start. Hard thrust after hard thrust plowed into Jennifer's upturned ass and she could do nothing but take it and verbally express her discomfort and displeasure. But she did not do that for long because a few moments after her first ass fuck started another guy got in front of her and fed his cock into her mouth.
Like the fellow in her ass the guy in Jennifer's mouth did not waste time and started to fuck Jennifer's mouth and throat hard. She was now getting it from both ends and could not even use her safe words if she wanted to because her mouth was too full of cock for her to say anything intelligible.
The cocks continued to saw in and out of Jennifer's mouth and ass for several minutes and Jennifer continued to make mewling noises and other unintelligible sounds. After a couple of very hard thrusts the guy fucking her ass said, "Here it comes baby," and fired his load deep in Jennifer's bowels. He pulled out. The guy in Jennifer's mouth did the same and took his place in her ass. Jennifer thought that she would get at least a small break in between ass fucks but her ass was empty for just seconds before a second large cock was forcing its way into her. Like the first guy this guy immediately fucked her hard and to the hilt.
"Oh, oh, oh," Jennifer said with each stroke but her words were soon cut short as another cock was pushed into her mouth. After a few minutes the second guy dumped his load into Jennifer's ass as did the third a few minutes after that.
Jennifer told me later that for the first three guys all she could do was to try to hang on as it felt like they were ripping her ass open and she had to just get through the pain. Somewhere towards the end of the third ass fuck she said that her ass must have gotten used to the size because she started to feel a tingle in her pussy. She said that she was also able to press her pelvis against the bench a little and this increased the pressure and sensation on her clit.
Half way through the fourth ass fuck Jennifer had her first orgasm. We could hear her moans even around the cock in her mouth and saw her body and legs tense up as she came. That opened the floodgates because Jennifer told me that she came at least once with each of the next three guys that fucked her ass.
Jennifer now had eight loads of cum in her ass and needed only to take one more guy before she would win our bet. The ninth guy would not be easy however.
The ninth guy had the biggest cock of the crew, he later told us it measured nine and a quarter inches and it was thick, not coke can thick but thicker than any cock anyone had seen other than in porn flicks. Even Ron Jeremy only beat this guy by a half of an inch.
He stepped up behind Jennifer, took aim and thrust his way into her ass. Jennifer's mouth was not occupied and she shrieked in pain. "Take it out, it's too big," she cried but he continued to push in to the hilt. He then started to pull out and Jennifer gnashed her teeth and said that she thought he was pulling her guts out. He pushed in again, faster this time and Jennifer yelled, "Yellow, yellow."
The guy stopped but did not pull out and gave Jennifer the thirty second break she was entitled to. He started to again fuck Jennifer's ass and she continued to beg him to take it easy but he was picking up the pace.
"Yellow, yellow," Jennifer yelled again.
The guy stopped and gave her another break and Paul came over and reminded Jennifer that she had used up her slow words.
Jennifer was panting trying to get used to the fullness in her ass and I tried to imagine what it would have been like if she had not already had eight guys to loosen up her ass before this monster pushed its way into her.
The time for the break was over and the guy said, "Hang on honey, the next time I stop is after I come in your little white ass."
The guy really started to let Jennifer have it and she continued to yelp and beg. One of the other guys got in front of Jennifer and was going to put his cock in her mouth to quiet her but the guy fucking her as waved him off saying, "Don't give her anything to take her mind off of what is happening to her ass."
With her mouth empty Jennifer continued to be vocal and the huge cock continued to fuck her ass hard. Somewhere along the way the pressure in Jennifer's ass must have gotten through to her clit because her cries started to turn to moans of pleasure. Even strapped down as she was we could see her valiantly try to raise her ass up to get more of the monster cock into her nether passage.
She continued to pant and moan and then on one particularly hard thrust Jennifer yelled, "Oh, God, I'm cumming," and exploded into an impressive orgasm. She was silent for a few seconds as the guy continued to piston his cock in and out of her ass and then yelled, "Shit, I'm cumming again."
The guy wrested three more orgasms from her before he finally blew his load into her ass.
Jennifer had made it, she had taken nine guys in her ass to win our bet but Paul and one other guy had not yet used her ass and the deal was that she would take the whole crew. By this point Jennifer was exhausted and did little more than moan softly as Paul and the last guy took their turn at her ass.
After the last guy had dumped his load Paul came over and gently ran his hand through Jennifer's hair. He said, "We are going to give you a little break to get cleaned up but remember we have you until 1AM."
Jennifer looked at the clock behind the bar and saw that it was just ten thirty. She had been getting her ass fucked for nearly two and a half hours. She also knew that she had a couple of hours more to go.
Paul and another guy undid the straps holding Jennifer to the bench and helped her to her feet. Her ass still gaped open and when she stood up a large dollop of cum came out and rolled down the inside of her right thigh. Paul held her up as she got her bearings and when she had steadied herself Jennifer walked through the club and into the changing room the club had off of the lobby. The changing room had a shower and a toilet and Jennifer said the first thing she did was to sit down on the toilet and let the cum flow out of her ass. She said that she could not believe how much cum came out of her.
Jennifer then took a shower and bushed her hair and otherwise made herself as presentable as possible. She put her heels back on and walked back out to where we were all waiting. The clock said ten fifty and after glancing at it for a few seconds Jennifer walked over to the bench and positioned herself to be strapped down again. You gotta give that woman credit, she is certainly game.
Two of the other guys did the honors and Jennifer was again soon immobilized. The fucking started again and Jennifer took on the crew a second time but this time they mostly came in her mouth and pussy. A couple of them had a third go at her.
Six of the guys fucked her ass a second time despite her pleas to, "Please use my pussy," making a total of seventeen ass fucks on the night.
At a minute to one in the morning Jennifer took two more loads, one in her pussy and the other in her mouth. We let her remain tethered to the bench for a while as the sperm oozed out of her ass and pussy and ran down her legs. There were also globs of cum on her face and in her hair.
The straps were unfastened once again and Jennifer went to clean up for a second time.
About 20 minutes later Jennifer came back in to the main room and asked for a drink. One of the guys prepared it for her and we all toasted to a fun evening.
A few of the guys had gotten dressed and left but many of those who remained were still naked as was Jennifer but as she had no clothes to put on she really did not have any choice. Eventually Jennifer wound up talking with the guy with the huge cock who was the ninth to fuck her ass. I could see her casting furtive glances at his tool which hung limply between his legs. Even soft it was an impressive specimen.
They continued to chat for a while and eventually Jennifer reached down and started to stroke his cock. It started to spring to life and the guy, whose name was Jayson, said, "Don't start what you won't finish."
Jennifer continued to stroke his cock and got down on her knees and took the head in her mouth. She took another inch or two but that was it. The cock was just too wide to fit into her throat.
After a few minutes of licking and stroking his cock Jennifer had it fully erect. She stood up and said, "I must be crazy for doing this but I never came as hard from a cock in my ass as I did when you fucked me the first time with it. My ass is sore from all of the fucking I did earlier tonight but I just have to feel that cock in my ass once more."
Jennifer then took Jayson by the hand and led him over to the bench. She draped herself over it and when two of the other guys started to put the straps on her she said, "I won't need those."
The guy who was about to fuck her ass said, "Yes, you will. Remember the first time when you used your slow word twice and screamed and begged and pleaded before you got used to it. I told you if you started you would finish and the way to make sure is to strap you down."
Jennifer said, "OK, if that's what you think."
"It ain't what I think, it's what I know. I have only found one lady in my whole life that has been able to take me in her ass without a lot of hollering and screaming at least at the beginning. People think having a huge cock would be great but it's a mixed bag because even though I can make women come hard with it there are a fair number of women who just cJenniferot take it in either their ass or pussy or who see it and freak out without even trying."
Jayson nodded to the two guys who had started to put the straps on Jennifer and they got back to work. They secured her legs to the side of the bench, locked her hands in the cuffs and put the straps across her waist and shoulders. They stepped away when they were done.
Jayson picked up the tube of lube and forced a dollop into Jennifer's ass. He used first one then finally three fingers as he stretched the tight ring of her ass. Her ass yielded easily to his invasion because Jennifer was still a bit loose from the night's earlier activities but she was not loose enough to take something as big as his cock easily.
"OK, baby, here we go," Jayson said and started to push his cock into Jennifer's ass.
"Aieeeeeeeeeeeeee," Jennifer shrieked as it popped through her anal ring.
Jayson pushed forward and in to the hilt and Jennifer kept shrieking in pain. "I changed my mind," she sputtered, "Take it out."
"Sorry sweetheart, I told you if we started that we would finish and that's what we're going to do."
"Noooooooo," Jennifer yelled, "It feels even bigger than it did the first time."
"That's cuz the first time the eight other guys had loosened up your ass and it's just closed up some since then but I will take care of that," Jayson said as he gave Jennifer a couple of strokes.
Jayson again pushed in to the hilt and Jennifer raised her head a bit and said, "Oh, it feels like it is going to come out of my throat."
Jayson started to pull out and Jennifer kept blustering and protesting and yelling. Jayson stopped and said, "Your getting exactly what you asked for so shut up and take it," and he slapped Jennifer's butt hard with his right hand.
"Eeeeowwww," Jennifer yelled. In just seconds you could see the handprint on her butt from where he had spanked her.
Jayson brought his hard down even harder on Jennifer's butt twice more and said, "Either way you are getting your ass fucked. It can be with a spanking or without one. I am going to keep spanking you as long as you keep yelling."
"But it hurts," Jennifer wailed and Jayson gave her two more hard spanks. You could now see several fiery red hand prints on her pale white butt.
Jayson had his hand up ready to give Jennifer another spank when Jennifer said, "Enough, I'll be quiet."
Jennifer was true to her word and although she continued to sob softly you could see her biting her lower lip obviously trying to muffle the sounds.
Jayson started to piston his huge member in and out of Jennifer's ass and although she continued to grunt and moan it was clear that she had decided that whatever the pain of her ass fucking she was going to do what she could stay quiet enough to keep him from further blistering her butt.
He continued to fuck her ass hard for a few more minutes and then said, "That's it baby, now you're getting into it," and we could see Jennifer almost imperceptibly moving her butt back a little to meet his thrusts. With the straps she could not move that much anyway but she was moving as much as the straps allowed.
Just like the first time, we could also hear that her moans of pain were becoming moans of pleasure.
Jayson continued to fuck her ass and Jennifer did what she could to help the process. Because Jayson had already cum twice this evening he had very good stamina and Jennifer's ass took a real pounding.
Stroke after stroke went in to the hilt and we could see a sheen of perspiration forming on Jennifer's body as she got close and closer to orgasm. As one particularly hard stroke hit its mark Jennifer screamed, "I'm coming you fucker."
Jayson stopped thrusting for a moment and let Jennifer just cum on his cock that was buried fully in her ass. A few strokes later Jennifer yelled, "Fuck, I'm coming again."
Jennifer came twice more before Jayson finally reached the end of his stamina. His last couple of strokes were so hard that the bench actually moved forward an inch or two on each. "Here it comes baby," he moaned as he dumped his load into Jennifer's ass.
He stayed planted in her ass for a couple of moments and then pulled out with a loud pop. Jayson walked around to the front of the bench and put his cock in front of Jennifer's mouth. "Clean me up," he said.
I thought Jennifer was going to freak out as she had never done ATM before but she just opened her mouth and started to suck and lick him clean. She later told me that she was still on such a high from how hard and often she had come that she would have done anything he had told her to do.
Watching Jayson ass fuck Jennifer had gotten three of the guys who were left hard and they approached the bench. When Jennifer saw the hard cocks jutting from their bodies she said, "Oh God, just please do not fuck my ass."
Jennifer could do little more than mewl softly as they took turns fucking her pussy. She later told me that she felt like she was floating in and out as they fucked her cunt and although she did not come she said it was pleasurable.
Seeing no more hard dicks in the room Paul walked over to the bench and said, "Congratulations, you have fucked out everyone in the room," and he loosened the straps and helped Jennifer to her feet.
She went to clean up for a third time and while she was doing that the rest of the crew left leaving only Paul and I waiting for her.
When she came out she was carrying a T-shirt that she had found in a box in the changing room. It was new and had the name of the sex club on it along with some other promo type stuff.
Can I wear this?" Jennifer asked.
"Sure," Paul said and Jennifer slipped it over her head.
She almost looked sexier with it on than she did naked because it fit her fairly tightly which caused her still hard nipples to clearly jut out in the front. It was only long enough to reach part way down her butt and her pussy peeked out invitingly.
"I will drive you home," Paul said, "We can get your car back to you tomorrow from my place."
Jennifer and I were no sooner in our front door when she took me in her arms and said, "There is just one more cock I want in my ass tonight."
We were naked in what seemed like only seconds and I bent her over the back of one of the chairs in our living room. I did not need lube as her ass was still slick from before.
We fucked hard for a few minutes before we both came just about simultaneously. I held Jennifer for a few minutes as my cock softened.
Jennifer led the way upstairs and I could not help but marvel at how sexy her ass looked as she walked up the steps in front of me or how sexy it had looked getting fucked by Paul's crew.
When we got to the top of the steps Jennifer turned around and greeted me with a kiss and said, "I hope my new car has soft seats because my ass is going to need them for a while."
