Lost That Bet

Last thanksgiving my wife and I spent the holiday with her family. My father-in-law is an accountant and a very proud chess player. He regularly challenges anybody at the house and takes pleasure in reminding us all he has placed in some tournaments and has been undefeated at family gatherings for years. I have always avoided playing him to the point where everyone has accused me of being a poor sport. On the Friday after Thanksgiving my wife, Jen, even begin teasing me about being afraid to play with him. Jen taunted me by saying mockingly that if I won she would do "anything" I wanted for a day; since it was a sure bet I would lose.

Jen knew I had played chess in college but she wasn't aware I was pretty good and keep in practice with occasional late-night online games. The big game was Saturday evening and after two hours Jen's dad resigned but not before pleading for a best two out of three competition. Jen took me aside and begged me to give her dad a chance to redeem himself. I looked Jen in the eye and said, "If I win you'll commit to do anything I ask for a full weekend?" Jen promised, "Anything." After three hours of chess on Sunday Bob graciously conceded the third game and apologized for haranguing me over the years.

Jen was impressed, very surprised, and a little chagrined. That evening when we turned in, I gave Jen a passionate kiss good night as I ran my hand down the curves of her body and told her I was going to go to sleep thinking about all of the things I was going to do to her on her payback weekend. When she mentioned dreading cleaning chores I told her I wasn't going to waste her time on cleaning when I could have a lot more fun making her act out all my sexual fantasies. I think it was at that point that Jen began to realize the possible consequences of her gamble.

Over the next few weeks I got more and more excited about the upcoming weekend and Jen got more apprehensive. Bringing home a gift of very sexy lingerie seemed to add to her anxiety. She attempted to welsh on the deal but I was having no part of the renegotiations and told her to relax and enjoy, as it would only be 48 hours and if she had the right attitude she could have a lot of fun. Jen pleaded for me to reveal my plans. I told her the plan was simple; she was going to do everything she was asked and be a really naughty wife for one weekend in her life.

When the weekend arrived the first instruction was to meet me for lunch at noon on Friday to start the 48-hour period. Jen looked great if somewhat nervous as we had a delicious sushi lunch. I had arranged an afternoon at the spa for her. That evening I told her to get dressed wearing a particularly skirt, blouse, and shelf bra and panties I had bought. Jen looked fantastic when she returned. She had never worn a shelf bra and was very self conscious as her bare nipples on her 36B boobs bounced delightfully inside her white satin blouse. Her shapely legs were well displayed in black thigh-high stockings and tight black skirt. Her soft silky shoulder length hair framed her sweet face.

We went to dinner at a nearby lounge and had a few drinks and light dinner. Jen was self conscientious as her bare nipples left visible impressions on her blouse and the shelf bra and low cut blouse left far more cleavage than she was used to exposing. Her hair was soft and sexy and the combination of spa treatment and drinks gave her an enticing glow. Her attitude seemed a mix of excitement, apprehension and curiosity. She gradually become more relaxed and less self conscience as the dinner and drinks continued.

As we settled our tab I told her I had invited a friend over to the house to play pool. Ben is a 35-year-old divorced friend and someone who I knew would be easy prey as he has been desperately lonesome and horny since his divorce several months ago. It was about ten when we met him at the house. At my direction Jen served us some snacks and drinks and watched the play while she nursed her drink. Eventually I turned my cue over to Jen and told her it was time for her to play. Jen is a credible pool player and with the advantage of distracting the competition, she did well winning the first game. Ben enjoyed the game as he eyed Jen's sexy outfit as she maneuvered for various shots. Ben had a noticeable bulge in his slacks as he positioned to enjoy Jen's cleavage on virtually every shot and was well aware of her stockings and half cup bra as she maneuvered for shots.

Jen was a giggly drunk as she seemed to enjoy the game as it progressed. As they racked up for the second game I whispering in Jen's ear that I wanted her to seduce Ben this game.

After what I said soeked in, Jen turned to me and whispered. "If you really want a naughty wife you're going to get a really naughty wife. Are you sure?"

"Absolutely." I responded, a little surprised and excited about her cooperation. She discretely unbuttoned another blouse button then proceeded to play pool in her flirtiest fashion. As she leaned over the table in exaggerated poses her blouse exposed generous views of her brests while her hiked up skirt hugged her cute butt and revealed the stocking tops and loads of leg. Her aroused nipples strained against the satin blouse fabric and Ben struggled to concentrate on the game. After about 15 minutes Jen moved in to put Ben out of his misery by taking his cue away and practically throwing herself against him. Jen pressed her body against a worried looking Ben then told him that tonight was his lucky night. Ben looked surprised as Jen pressed her chest against Ben and said she was following specific instructions. She matter-of-factly said, "If you don't want to get in my panties tonight my husband is determined to find someone else who will."

Ben looked across the pool table at my confirming smile and needed no more convincing. In seconds he was grabbing and groping like a soldier on leave. Clothes flew as Ben excitedly unbuttoned the remaining blouse buttons and buried his face in Jen's breasts. She quickly unbuttoned his shirt and unzipped his pants. The shelf bra left Jen's nipples beautifully displayed on her firm breasts as her hands worked down Ben's pants. Her aroused nipples and frantic groping made it clear she was as excited as Ben. The two stumbled around the game room as cloths were being shed. Ben unzipped then worked Jen's tight mini-skirt down over her hips uncovering her skimpy lacy panties. In the meantime Jen had his slacks down and was groping his package through his briefs. They uncoupled long enough to step out of their pants and skirt respectively before reengaging. They kissed and their tongues begin exploring. Ben simultaneously fumbled with the hook on Jen's bra and after succeeding his hands moved instinctively to Jen's ass cheeks accented nicely by her thong panties. Jen soon freed 6 inches of rock hard cock.

In a matter of moments Ben had Jen lying on the couch and was peeling off her panties revealing her nicely groomed pussy. Jen was frantic, pleading with Ben to "do me." It wasn't long before Ben had his face plastered on Jen's pussy lapping at it like a starved man. Ben was getting the desired response as Jen was moaning and wiggling as his teeth and tongue explored her private areas while his hands fondled her ass and occasionally grabbed a boob. Jen looked fantastic as her smile gave away her pleasure and her body responded to the stimulation of a different man for the first time in years. Her skin glistened with heat and her nipples strained in full arousal as Ben now focused on her clit. Ben feasted patiently as Jen neared climax then he replaced his lips with his cock and quickly planted it deep in her wet cunt. Her whole body shook as he began fucking her. As I watched from a few feet away Jen turned and panted, "Is this naughty enough?"

Ben took long deep thrusts at a controlled pace for several minutes relishing the feeling of Jen's hot cunt clutching his tool and the sight of her boobs bouncing to his thrusts. Soon he got so excited he lost his self-control and began pummeling Jen faster and faster as he neared climax. Jen's body movements and squealing sounds were also involuntary as she climax.

Ben collapsed having unloaded deep in Jen's pussy. After a brief recovery we moved to the bedroom where Ben spent the next hour licking, kissing and fondling every square inch of Jens' body. The evening ended with me fucking Jen from behind while laying on her side in the middle of our bed while she sucked Ben's cock to climax.

After that we all relaxed and I explained to Ben about the chess game and Jen's subservience for the weekend and how I had decided to live out a few of my fantasies of seeing her with another man. I mentioned how I would like to see her get a little more action but hadn't figured out how I was going to come up with more horny safe guys. After a little late night snack of tit sucking Ben thanked us and excused himself for the evening. Jen was exhausted and fell asleep.

Early the next morning Ben called on my cell phone. I could tell he was nervous as he asked if we felt OK and were ok with that had happened the night before. I assured him we had very much enjoyed the experience and I appreciated his participation and the tenderness he showed Jen. Ben hesitated slightly then said he had an idea. He was scheduled to host a few buddies for dinner to celebrate the finalization of the divorce of one of the guys in a little divorcee support group he was part of. On the way home it came to him that perhaps his group could help me give Jen a little more action. The diner was steaks at Ben's at 8 if we were interested. There would be a few two other guys, both relatively recent divorcees; and, he added, "Handsome, clean and horny." He was going to check with the guys and I was going to think over whether or not I really wanted to share Jen another night. As I hung up I had visions of Ben fucking Jen and thoughts of seeing her with other guys racing through my head.

When Jen woke up she was all smiles and seemed invigorated from the night before. Her fear of the dreaded weekend had turned to anticipation. She asked what was planned for the day. Our Saturday was relatively routine and relaxing. Other than having Jen do some housework in her panties and bra and run some errands in an embarrassingly short skirt and tight top, I made no special requests of her. About mid afternoon she asked if I had plans for that evening. I had told her we were probably going dancing. Still undecided I didn't tell her about Ben's offer.

Recalling my parents' advice about only living once, I decided to tell Ben we would come and see what transpired. Ben said the guys were looking forward to it and asked if there were any particular requests or ground rules. I mentioned the best way to get Jen horny was Sangria and flattery.

I told Jen we had diner plans then would go dancing. I picked out some lingerie and a dress I wanted her to wear. It consisted of a silver satin bustier that hiked up her tits and accentuated her waist, a matching pair of satin panties, silver colored stockings, and a snug, plunging neckline black slit evening dress she hadn't worn in years. When Jen was dressed she looked wickedly delicious and she knew it.

We arrived at Ben's at 8:30 and were quickly introduced around. Jen was a self conscious given her sexy outfit and being the only woman around four men but figured we were going to a dance club after diner. Ben's two friends were delighted to meet her and fawned over her complimenting her on her great looks and sexy dress. Ben was grilling the steaks and Jack, the newly divorced guy, fixed Jen a Sangria. Any nervousness quickly disappeared after Jen finished her first drinks. For the next hour everyone dined and visited.

After dinner we retired to the living room and one of the guys asked Jen to dance. Jen looked at me with a quizzical look. I told her, "Welcome to Ben's dance club, where you are the entertainment." The next half hour consisted of the guys taking turns dancing with Jen which was a thinly disguised opportunity for them to do some one-on-one flirting and a little fondling as hands wandered freely. Ben discovered that Jen was wearing stockings and garter straps and each successive guy freely fondled Jens' dress seeking to confirm his discover. Jen got into it herself, teasing the guys about the bulges in their pants.

Everyone in the room was ready for more serious action. I asked Jen to do a lap dance for the newly single Jack to help him celebrate. While Jen had never done any lap dancing, she was a good dancer and had seen a few movies so she said she would try since she had promised to do anything. She moved real well to the music lubricated by several drinks and had every eye in the room glued on her as she squirmed and wiggled inches from Jack. The guys cheered Jen on telling her she was a great dancer then urged her to strip. I nodded to Jen to comply. Jen asked Jack to unzip her dress and when he discovered a stuck zipper I told him to pull hard. He split the zipper and ripped the dress apart creating a surge of suspense and excitement as Jen's dress was pulled open. Jen's sexy lingerie was soon on display and Jack couldn't keep his hands off her. He soon had his head buried in her cleavage as she squirmed on his lap on a chair in the middle of Ben's family room. Jack was completely turned on and had Jen step out of the remnants of her dress while he quickly removed his pants and underwear releasing a nice sized rock hard cock. As Jen straddled him he pulled the crotch of her panties to the side and quickly placed her moist pussy lips on his cock. He eased her down on his lap. Everyone was cheering as Jen resumed her grinding, this time with Jack's cock deep in her pussy and his hands pawing her ass while his mouth was working on her tits bulging over the top of her bustier. She was moaning to the delight of the audience. She seemed to be completely hypnotized by the attention and stimulation. There was no pretense of anything but animalistic lust as Jen focused on pleasuring herself and anyone else she could get her hands on. With each trust she grunted with pleasure with her chest heaving and hands flailing. Soon Jen had her hands and mouth full as two additional rock hard cocks surrounded her. Jack managed to rip apart the waistband of her panties and was removing the scraps of fabric while she continued to bounce on his cock. Jeff was now fucking Jen's face as he worked half his long cock into her mouth. Jen took more and more cock in her mouth as Jeff increased the pace of his stroking. Jens' cheeks bulged with each stroke of Jeff's cock. Her' hand was working Ben's cock when she could concentrate and he entertained himself by unhooked the shoulder straps on Jen's bustier and pulling down the cups so her tits popped out of the bustier cups.

Jen was completely absorbed in getting fucked, grinding her pussy into Jeff and practically inhaling the cock in her mouth. Ben, whose large uncircumcised cock was getting the attention of Jen's right hand, was first to begin warning of an impending eruption. He soon let loose landing several streams of hot cum on Jen's tits. The sight set off a chain reaction as Jeff pulled out of Jen's mouth then plastered her tits with his load. Jeff, still fully implanted deep in Jen's cunt, began jerking uncontrollably as he and Jen both reached climax.

Everyone was overcome with the intensity of the scene as Jen sat catching her breath dripping in cum. Needless to say I had never seen Jen like that before. My usually proper wife was reveling in being a complete slut. I helped her climb off Jeff and positioned her over the arm of the couch with her ass in the air. I then spread her legs and quickly entered her soaked pussy from behind and began pounding into her. With her gorgeous ass pressing into my groin and the images of her cum covered tits in my mind, it wasn't long before I pulled out and plastered her ass with a giant load of cum.

After a short rest I challenged the guys, asking who's next. Ben quickly stepped up and rubbed his cock up and down Jen's cum covered crack before beginning to probe for her asshole. Jen was panting and moaning continuously as Ben began pressing his now hard cock against her ass. After a few soft probes he had the head of his cock in position and pushed his way into Jen's asshole. She was moaning so loud I thought the neighbors would hear. Ben was ecstatic, admitting his wife had never let him fuck her in the ass. Jen's naughty wife behavior now carried over to her language as she was panting uncharacteristically dirty language, "Fuck me, fuck me, fill my ass."

Ben increased the pace of the pounding. After a few dozen strokes he came deep in Jen's bowels as she climaxed continuously from the anal stimulation. Jen's inviting ass and lustful language had tempted Jeff to line up for a turn. Jen's now stretched rear made taking Jeff's larger cock relatively easy as he slid in balls-deep with only a few thrusts. The effect on Jen was no less as she continued moaning loudly until Jack stood and quieted her by feeding her his cock and fucking her mouth as she took deeper and deeper thrusts with no complaints. Todd came first, slamming into Jen with several final thrusts. Jack lasted only a few moments longer before he announce he was coming and pulled out and unloaded his load on Jen's face. Jen's body twitched a few final times as she collapsed in a cum-covered heap on the couch, naked except for stockings and a bustier bunched around her waist.

After a rest I asked for volunteers to clean Jen up in the shower. Jack volunteered and helped Jen to the master suite. Everyone followed and the next half hour involved the guys taking turns cleaning up in the shower and taking a turn at soaping up Jen. I was the last in the shower and told Jen I was going to leave her at Ben's for the night and I expected her to make sure every guy was completely satisfied. I dried her off, took her to Ben's bed, and gave her a passionate kiss before returning to the family room. I told the guys that Jen was in Ben's bed but that anyone who wanted another turn had to make her come with oral sex first. I would pick up my wife tomorrow. As I headed to the door Jeff was undressing again and heading to Ben's room.

Sunday noon I headed over to Ben's to pick up Jen. When I arrived she was eating breakfast dressed in Ben's t-shirt. She thanked Ben for the hospitality and told me she had finished paying off the wager with the most incredible 48 hours in her life - and it was time to go home and nap. A few days latter Jen got a note and gift card from the "Divorcee Club" offering her an honorary lifetime membership and invitation to visit again anytime she felt naughty. She confided that after I left there was another two hours sucking and fucking before everyone was done and Ben had fucked her in the ass one more time in the morning.

I'm not sure when the mood for a naughty wife will strike again but I suspect it won't take much convincing to get Jen to participate.