MILF Chronicles Ch. 01

The problem was, I didn't remember what it was and he refused to repeat it, so I had to give up on that round. As he kissed my wife he didn't let up on his assault one bit, and Sherry was doing a poorer job thwarting him so by the time his ten seconds were up he was squeezing a tit with one hand and had the other one up to her pussy, although I don't think he could do much with her thighs clamped together as tightly as they were. Someone called "Time!" and Sherry leaped up out of his grasp, looking very flushed and flustered.

I was down by two now and could not afford to miss another, and although I suspected my odds winning this game were not good, I determined to not let their man-handling of my wife distract me anymore. Certainly whatever they had planned for the next game it would be worse for her than what they were doing now, so I had to avoid that if I could.

Johnny was up for his second round and once he asked the question he, of course, attacked Sherry. Two things were in my favor: 1. Since he was across the table I could not see what was going on below her waist, and 2. He was not as aggressive as the others so she was able to fend him off more successfully. This allowed me to concentrate and answer the question correctly.

I only had two questions left, however Marc was the next player and from what I could tell he was the pervert of the group. Sure enough about five or ten seconds after starting to work on Sherry she squealed and tried to jump off his lap. He pulled her back down but in the brief instant that she had partially stood up I could see what her objection was -- he had unbuttoned the bottom two or three buttons on her blouse (there where only five) and was stroking her bare midriff. This completely unhinged me and I blurted out an answer, but as soon as it was out of my mouth I knew it was wrong.

"Ha! You lose!" Brian exclaimed as Marc took his ten second prize. Sherry either really liked the way he kissed or had given up because she was not fighting him anymore. Fortunately he did not try to undo the last few buttons on her blouse and satisfied himself with trying to push his hand down the front of her jeans. Due to how tight they were however, he did not succeed and he did not have enough time to attempt to unbutton them. When they finished she got up and walked over to me looking a little glassy-eyed and breathing heavy. All the kissing and groping was starting to have an effect on her, apparently, although I expected her to have more control of herself.

"All right, admit it then, you suck." Brian said triumphantly. I glanced at Alex and he gave me the 'no' sign, so I knew that was not what I was supposed to do. But I didn't know what to say at this point either.

"Maybe you'd like another chance?" Alex asked, but it was clear how I was to answer.

"Yes I would." "OK then, let's play the same game again, except how about we raise the stakes, eh?" Alex offered.

"How about we play for your wife's clothes?" Marc said with a nasty little smile. The others quickly agreed, of course, but even though Alex was signaling 'yes', I hesitated. "Well..." I stammered, to which Alex signaled 'YES!'

I had no choice, "OK." I said quietly.

That got Sherry's attention. "What?!" she demanded. "Don't worry, I won't lose this time." I assured her.

"You don't have to lose the game to get me half-stripped." she complained.

"Trust me." I said, hopefully with more confidence than I felt. "Besides you've gone to the beach in a bikini showing the same amount of skin as you would in your underwear." I reasoned.

"This is not the beach!" she objected.

I stood up, wrapped my hands around her, gave her a hug and kissed her. Then I looked her in the eye and said softly "I love you, but please just do what I ask now and trust me." She still looked uncertain, but answered me by stepping over to Brian and sitting in his lap. This brought a smile to Brian's face.

"But before we start we need to clear up a few things." Marc stated. "First, shoes, hose and jewelery does not count. So how many items do you have on Sherry?"

"Four." she answered

He continued. "Good. Second, the winning player gets to choose which piece of clothing to remove and also gets to remove it. And third, since this is a tougher challenge we will spot you another question, so now you have to get only nine out of twelve. OK?" Everybody nodded yes, including me. It only occurred to me a few seconds later that they only moved the goal posts so that should I lose, my wife would be completely nude. If she had figured this out as well, she gave no clue.

The game proceeded as before, except that they wasted no time in pawing at my wife. I got the first two questions correct. The question that Marc asked was one I just didn't know, so I guessed -- wrong. Marc selected her blouse and this time was allowed to completely unbutton and remove it.

Now Sherry was moved over to Alex, all eyes on her skimpy bra and creamy tits barely covered by it. I knew I needed to do better, because the more clothing she lost, the more difficult it would be for me to concentrate. Now Alex had much better access to my wife's tits and took advantage of it. He was almost putting his hands inside her bra and probably would have if I hadn't answered the question quickly; and wrong as it turned out. Alex just smiled and told Sherry to stand up. Then he unbuttoned and unzipped her jeans. He looked straight at me as he eased them down past her hips, revealing her skimpy black thong. As he continued to push them down her legs he leaned over and looked directly at her barely covered snatch. Blushing, she stepped out of her new jeans. Now wearing only a sexy bra and a small thong Sherry headed around me to the next player. As she passed behind me she leaned down and whispered in my ear "Enjoying yourself?" I wished I could tell her why this was happening, but I couldn't.

When she tried to sit down in Brian's lap, however, he made her straddle him, face to face. At first I thought it was to make it easier to kiss her, but as soon as the question was read he grabbed an ass cheek in each hand and pulled her into his crotch allowing him to grind his hard-on into her almost exposed pussy. A small involuntary (I hoped) groan escaped from my wife. Somehow I had to finish this game, and without Sherry losing any more clothes, so I tried not to let Brian's antics distract me and I thought about the question. It was difficult though as my own arousal was starting to build. On the one hand I was disgusted with what was happening and how we were being manipulated (literally and figuratively), but on the other I was getting turned on. All I could do was press on, so I dug deep into my memory and dredged up the correct answer. Brian was visibly disappointed as Sherry moved on to Johnny. It was no surprise that he too had her sit facing him, and she didn't even try to avoid it at this point.

The question was difficult though, and I got it wrong. "Now, now," he mused, "tits or pussy, tits or pussy?" Everybody but me gave him their opinion. After thinking about it for a few seconds he reached out and unsnapped my wife's bra, revealing her succulent 34C's to this group of testosterone charged men. She tried to hide them as she stood up and moved over to Marc, but that didn't last long. As soon as the question was asked he was all over her like a bum on a baloney sandwich. She was actually doing a pretty good job keeping his hands off her tits until he reached down and apparently, although I couldn't see, tried to get his hands into the front of her thong.

When she reached down to grab his hands he latched onto one of her tits with his mouth and started sucking on it. She loves this and will really juice up whenever I suck on her tits and flick her nipples with my tongue. Her response now was not much different. I watched my wife's eyes narrow and her mouth open slightly as this stranger suckled on her breast. Her struggles began to weaken and Marc took advantage by freeing one of his hands and grabbing her other tit with it. He was twisting her nipple with that hand and I think he hit pay-dirt with the other one down the front of her scanty undies because her eyes suddenly popped open and her whole body twitched visibly. I didn't know how much longer she would last before she orgasmed, so I gave up on the question, which I had forgotten anyway, just to end the game. I had to pick one humility over the other and I thought that full nudity would be preferable to cumming in front of these guys.

Marc reluctantly stopped his assault on my wife when I repeated my concession, Sherry's tit slipping out of his mouth with a lewd pop, his saliva glistening on it. "All right darlin, get up and be prepared to be stripped." he told Sherry.

He had to rearrange his pants to stand up, but then again, to my shame, I was in the same condition. Her small sexy thong was a bit off kilter, evidence that Marc had indeed managed to get under it. But the big surprise was the fact that it was soaked to semi-transparency! It even looked like some pussy juice had leaked down her inner thighs. My wife almost never produces that much lubricant, unless she is extremely turned on. I would have thought that her embarrassment would have precluded that. Maybe I didn't know her as well as I thought.

Marc slipped his thumbs into the string-like sides of her underwear and slowly slid them over her hips and down her shapely legs. Once they were down to the floor Sherry helpfully stepped out of them. What else could she do? She just stood there staring at me helplessly with this 'save me' look in her eyes. I was ashamed that I could do nothing to ease her humiliation and looked down at the table.

"As long as you are dressed, um, undressed for the part," Alex spoke up, "why don't you go get us some drinks."

"Like this?" Sherry gasped, motioning at her nude body.

"Sure," he answered, "everybody else has gone home, we're the only ones here." Then everybody gave her their drink orders, except me since I wanted to sober up. Maybe that would help me think of a way out of this. But Alex would have none of that; he insisted that Sherry get me a beer and a glass of wine for herself. When she looked at me for confirmation I smiled weakly and nodded my consent. With that she turned around and headed for the bar, which was down the hall and around the corner.

When she was out of the room Alex informed me that since I lost the second game, we would have to play another one, except the stakes, of course, would be going up. It would also be based on a different board game. This time it was a strategy game that was slightly modified. Basically it was an 18th century sailing game where I played the authority being pitted against the other four playing pirates. Normally the pirates plundered gold and jewels and hid in safe harbors while the authority tried to catch them and put the treasure back where it came from. The authority had a faster ship and was able to use some routes that the others could not, so in theory the game was balanced, but it depended a lot on the players

They had replaced the treasure markers with new versions that had a picture of a hand, a mouth, or a hard cock. They had also put pictures of a woman's mouth, tits, and pussy on the safe harbors. The rules were that if they could get a 'treasure' token to a 'safe harbor' they would have one minute to use their corresponding body part on my wife. If someone else was already there, they got ejected and had to return to the table. There were more hands than cocks and only one pussy safe harbor, but the possibilities made my head spin and my cock throb.

Alex made it clear that I was again to convince her that the entire thing was my idea. I also had to 'prepare' her for the game. To win the game we had to play through 30 rounds without Sherry cumming. Since I only had 15 seconds to move my ship, and they had 15 seconds (they all move at the same time), each round would take about 30 seconds, which meant the game would run for 15 minutes.

Depending on how often they got to safe harbors, that could easily be too much for my wife in her current aroused state. If she made it though, we would be free; if not, then they got to have their way with her for the rest of the night, and I had to watch but would get no relief myself.

When Sherry returned she had the drinks on a small tray and circled around the table handing them out. As she passed each man her ass, tits, and pussy were grabbed, squeezed, and prodded. When she finished she stood nervously by me drinking her wine.

There was an awkward pause and Alex broke it by announcing that I wanted to play another game. Sherry didn't say anything, but her eyes were like lasers that bored smoking holes through my soul. I coughed and said as enthusiastically as possible, "Yes, but don't worry, I picked a strategy game, and you know how good I am at that. I'll smoke their asses this time."

She didn't look convinced. I stood up and motioned her over towards the other side of the room where Alex had folded down the futon there. I was hoping I could whisper the truth to her once I was away from the other guys and let her know what was really going on, but Alex followed us.

"The stakes are a little bit higher this time, but I promise you it will be OK. Just do exactly what I say." I told her has I sat her down on the futon. Alex handed me a silk blindfold. "OK, I'm just going to put this blindfold on you." I said as I wrapped it around her head and started tying it. "Why?" she asked.

"To help you relax and add a little mystery to the evening." I answered. Then I pushed her down onto the futon until she was laying flat on her back. "Just relax" I tried to say in a soothing voice.

Now the hard part. I lifted her near arm and flopped it back so that her palm was up and lying by her head. Then I took the silk scarf that Alex handed to me and began to bind her hand to the frame of the futon. She reflexively tried to jerk her arm away, but I held on to it firmly.

"What are you doing?" she exclaimed. I leaned into her and used my sincerest voice. "I love you very much. I know you are confused and your emotions are in a jumble, but please trust me. I know what I am doing, and this is how I want it done. Just let all of your doubts and concerns go and just live the moment." Her arm relaxed and I tied it down. Alex did the same thing on the other side and gave me a thumbs-up sign.

Now the harder part. I leaned over and kissed her deeply while stroking first her arms, and then her tits. I pulled away and kissed my way down her neck. Alex was still close, so I still could not tell her what was going on, but at this point maybe that was better. She would need to take my advice and just let go if she was to survive the rest of the night, especially if I lost the game.

"I love you very much. No matter what happens, I'll always feel that way. You are the sexiest, hottest woman I know. I'm the luckiest man in the world to be married to you." As I said this I slid my hand down her trembling body to her dripping pussy. I ran my fingers through her well trimmed pubic hair, across her hot mound, and slid a finger into her. I pumped in and out a few times, stroking her g-spot each time before removing it and running it up her slit and finally over her clit, making her jump. My wife groaned at my withdrawal. Her body was covered by a thin sheen of sweat, her nipples were as hard and distended as I've ever seen them, and her pussy gaped open slightly showing the inner pink folds. Hot damn she was the sexiest woman I've ever known! I wanted to jump her right there; my cock was so hard it hurt. Turning my back on her and walking over to the table was one of the most difficult things I have done in my life.

The first few rounds of them game were mainly just maneuvering while I tried to figure out what they were up to and vice versa. On the fourth round I decided to get aggressive and sent Marc's ship back to his starting port. The other three took advantage and tried to grab some treasure. Brian got a hand and Alex got a mouth. I managed to stop Johnny from getting anything, but now I had to concentrate on Brian and Alex.

The next turn I caught Alex and I had a choice of taking his treasure or sending him home. I took the mouth token and put it back on the island it came from. This allowed Brian to get to a tits harbor and Johnny got a mouth token. Brian smiled, stood up, and went over to the futon where my wife was tied down and blindfolded. He started playing with her tits causing her breath to catch. I couldn't watch since I had to execute my next turn, but I could hear my wife's occasional soft moan.

I managed to keep the other three at bay for the next turn, but Marc snagged a mouth token and Alex got another hand. On the following turn I managed to intercept Marc and confiscate his token, but Johnny managed to get to the mouth harbor, so he went over and started kissing Sherry while Brian continued his assault on her tits. I tried to keep an eye on them to make sure they didn't cheat, but it was difficult to split my attention without making errors in my play. It seemed I was damned no matter what I did. With only two players I was able to keep them both out of a harbor for the next round, but after that Brian's ship was back in play and I kind of lost track of Alex. The next thing I knew his ship was in the pussy harbor and he was off to finger fuck my wife!

Alex must have been doing a good job because her moaning was louder and more frequent as he pushed first one, then two, then three fingers in and out of her hot hole while stroking her clit with his thumb (OK, I peeked -- I couldn't help it). The squishing sounds and the moaning was making it hard to concentrate, and as a result Johnny managed to get into a tits harbor with a mouth token. He joined Alex with my wife and started sucking on her already hard nipples. This sent Sherry into a near frenzy, her head was rolling back and forth and she was struggling against her bonds. I think the only reason she had not orgasmed yet was because of the embarrassment of being in front of these four strangers.

Most of the game went on like this, just one or two of them with my wife at any one time, and a couple turns nobody was there. At one point Marc got into a tits harbor with a cock token. It was surreal watching him climb up on top of my wife, press her tits together and fuck them.

Near the end of the game I was starting to hope that we could win. I had managed to keep down the stimulation of my wife so she had not climaxed yet and I had a handle on their individual strategies. Then they did something that I didn't expect: they started working together.

Johnny and Alex sacrificed themselves a couple of turns in a row which allowed Brian to get a mouth token into the pussy harbor. I was crestfallen; surely he would be able to make her cum with his mouth.

He casually walked over to the futon, gently spread Sherry's legs, knelt down and ran his tongue the entire length of her hot slit. Sherry let out a guttural sound and pushed her pelvis up to meet his lashing tongue. I had to hope she could hold out, even though she didn't know she had to, and continue the game. We could still win -- there were only four rounds left. They continued to work together and after two more rounds although Sherry had not cum yet, she must have been close. Then it happened: Marc got a cock token to the pussy harbor. No!

He stood up, pumping his hand in the air and hissing "Yes!".

He walked over to my wife on the futon and stripped off his pants and underwear. His cock was hard and standing out from his body slightly. It looked a little bigger than mine, both in length and girth. Sherry's legs were already parted, but he pushed them apart even further and climbed up onto the futon between them. He wasted no time in penetrating her and sank to the hilt in one stroke, she was so wet.