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Anything The Bet ,part Two (will And Michelle Se...

"So, you want to go through with The Bet huh?" He smiled. "Oh yes!" she answered with more enthusiasm than he had expected as she reached over to her dressing table and grabbed two quarters she had placed there earlier.

"Just like that huh?" Will asked her. "Yes, lets do this.."She smiled back "..and may the winner take.....ANYTHING"

"OK, seeing as you called for the bet, I will make my call Odds, which makes you Evens...work for you?" he stated as he picked up one of the offered quarters, looking over both sides to be sure it was a regular heads and tails quarter. She laughed noticing him look "HEY, that's more like something YOU would pull!!" He smiled a little sheepishly and stuck out his tongue at her.

"On three we toss them" Michelle readying her own quarter." One.........Two...........THREE" and they both flipped the quarters into the air. Michelle's landed first , TAILS up....., then four eyes watched as Wills quarter came down.......It was....

HEADS!!~

"Odds... looks like I win." Will said with maybe a little bit too big of a smile.

"Yes. Looks like you won....so...." Michelle smiled with "that look" in her eye " what do you want?"

"What I want is, like the bet says, Anything. So, this Saturday I plan on collecting my prize." Will replied with a smile.

"Ok??... a bets a bet. Saturday then. Any 'special requests'?" Michelle asked, which was her way of asking if there was any particular way he wanted her to dress.

"I will let you know before Saturday." Will snuggled up to her "Do YOU have any special requests right now?"

"Well...."she grinned" how about putting that cock of yours in my mouth?"

"Why not?" He grinned back, moving up the bed to where she lay back on the pillows. She reached her arm between his legs as he presented his already hardening cock to her.

Cradling his balls in her hand, she licked playfully at the glistening head of his cock, then took him deeply into her mouth.
Michelle wasn't just good at sucking cock...she loved it and it showed. Will could see it in her eyes as she looked up at him. Her eyes shined with a what could only be described as a contented lust, the desire to have a cock in her mouth being fulfilled, but at the same time that was only feeding the growing flames of her lust for other things.

She worked him in and out of her mouth, his cock slick with her saliva. Her hand grasping his ass and pulling him deep into her mouth, forcing herself to take him fully down her throat and holding him there for a moment.
She was rewarded with a "Good girl" from Will as she worked hard not to choke on his thick hard cock, then sliding him back out to slip a tongue over his length before taking him in once again. He was above average in length and quite thick, so she was a bit proud she was able to take him all now. It had taken some practice that they both were happy to do.
His hips rocked in a matching rhythm to her attentions, as his hand wandered down her body. Her legs parted welcomingly when his hand sought out her pussy, which he was not surprised at all to find was dripping wet. He slipped his two middle fingers deep into her and was rewarded by the resulting moan Michelle made around his hard cock.
Will worked his fingers in deep, finding her hot button he knew was there, and began matching the thrusts of his fingers with the thrusts of his hips. Michelle moaned deeper, Wills fingers fucking her pussy as she took his thrusting cock into her mouth again and again. He could feel her stiffening, on the brink of a climax. Pressing his fingers in deep and pulling up hard, while at the same time pressing his cock deep into her mouth, he drove her beyond that brink and she trembled as the orgasm rocked through her body. Her moans felt wonderful on his hard cock as she came, and Will coaxed her orgasm along with gentle thrusts of his fingers into her now very sensitive pussy. She continued to tremble under his attentions, and he pulled his cock out of her mouth to just look down and watch her face. Her breath came in gasps as he continued to finger her hard once more, her hips thrusting upwards to urge him along.
"Gawwd ...your making me....Cum ...AGAIN!!!!" she almost screamed as another climax crashed through her. He returned to the gentle teasing rubs on her clit...each little touch making her shake. Her clit was almost too sensitive to touch now.

Will loved it when she was this sensitive. He smiled as he repositioned himself between her spread legs.
Michelle looked up almost pleading for him not to do it, but knew that would not stop him. Kneeling between her spread legs, he put his arms under her knees and pressed her legs back as he guided the head of his hard cock to the entrance of her hot box. She turned her head aside and moaned as she felt him rub his cock up and down along her slit....lubricating himself with her natural flowing juices, then with a single hard thrust of his hips, he drove himself fully into her.

She threw her head back and her body stiffened at the sudden and forceful intrusion. He pulled back and once more slammed into her hott pussy, pressing hard and deep into her. He could see in her eyes he was finding all her hot spots, she always said his cock fit her just right.

Wills hips began thrusting his cock in and out of her at a hard and steady pace, and he could see in her eyes he was forcing another climax to build within her. His pace quickened as he pounded her relentlessly, her almost animal like noises of pleasure urging him on "AHHHh... Ummmm.... Ohhhh" her noises matched pace with this thrusts as her head rocked from side to side, her hips pressed back to meet his. She could feel him growing even larger and rock hard inside of her.

"ARRRRRRRRRRRRRRRRR..yessssssssssssssssssss" she almost screamed as her climax neared, and knowing that he was nearing his own only fed her fires further. Will thrust his hips forward hard and pressed himself deep into her. She could feel his hot seed filling her as his cock pulsed and throbbed inside of her, triggering her own shuddering orgasm. Her body stiffened and trembled under him as he pressed himself deeper and almost growled his release into her. His hips pumping slightly, milking both their orgasms along. Riding them to their sweet end, he pulled out of her and lay back down next to her.

She snuggled up next to him and they just lay there enjoying the mutual contentment. It was her that broke the silence.
"So, are you going to give me any hint at all about what you want Saturday?"

"Nope, its going to be a surprise." is what he said.... what he was thinking was "I don't have a fucking clue."

He kissed her deeply and got up to get dressed. "Your really not going to tell me are you?" she asked.

"I will be sure to clue you in when you need to know" he smiled.

She was not satisfied with that answer, but she smiled as he kissed her goodbye to return to his own home across the street.

It was a short walk, but Will was already trying to figure out what he was going to ask for as his "winnings". This was a little bit like a sex genie granting you one wish. "Anything." Not to over think it , but hey, this was one of those things that didn't happen every day. He was not going to waste this opportunity.

Now someone from the outside who didn't know better, it would be so easy to pop off suggestions. "Make her give you a blow job!" yes those were quite nice, but she was more than happy to accommodate those. "Make her have a threesome with you."
HELLO.... that's like making a fat kid eat cake. Been there done that and will do again. He could not help but smile at the memory of the time she invited him to a party and there were only three other guests there,all women.(See "The Party" story) or when she blind folded a girl friend of hers and invited him over to help pleasure her. (See "Michelle Squared" story).

Ok, then, what about....Anal? Will smiled at that thought. Michelle was an anal virgin until not too very long ago. She had her own personal sexual bucket list, and being "double penetrated" also known as DP, was still unchecked when she approached Will about it.She had engaged in some ass play, and been penetrated by toys, but never "ass fucked".
Michelle and he had a great relationship, being both neighbors and fuck buddies, but they were both also swingers and had active sexual lives outside of their own relationship. It was unusual, but it worked out great for them. No drama. No expectations.
Michelle had a couple she enjoyed playing with on occasion and one day she asked him if she would help with a fantasy of hers.
To be DPed. She explained she had tried it with a couple when the gal had a strap on and it was fun, but she wanted the 'real deal', two men, two cocks, two holes filled.

Both Will and Michelle enjoyed fulfilling fantasies, others and their own, so he told her he would be happy to join the party. It was a couple of days before they could all get together, but finally Michelle said it was all set and he rode with her to the couples home.
After sitting around talking in their living room, Michelle being the shy little thing she is suggested that they all go upstairs and have some fun.
The couple started off with each other, and Will was quite happy to have Michelle give him a welcoming kiss and lay him back, working licks and kisses down his body as she made her way down to his cock. He lay back watching her take his cock into her mouth and began greedily sucking and slurping happily on him, her ass in the air. It was not long before the other gal took note of the activity and told her husband. "Look what Michelle has for you."
Will watched the man position himself behind Michelle, and could not help but notice the guy was hung. Will was above average, but this guy was a couple of inch's longer and a little thicker than he was. He could hear and feel Michelle grunt and moan happily as the man worked his cock into her nicely presented pussy. Soon he was fucking away at her wet pussy as she busied her mouth on Wills cock. The wife enjoying the show, and seemed to be fond of talking about it all. "You like fucking her pussy don't you?" he nodded in agreement.
"Look at that huge cock in her pussy." The wife grabbed a camera and started taking pictures of the scene. Will made a mental note to check for face pictures, some things he just didn't want documented.

After a bit Michelle drew back and told the guy, "I want to watch you fuck her!" He happily complied and while he repositioned himself between his wife's legs, Michelle caught Wills eye and gave him a wink. Will figured this was some of what they had been enjoying as a threesome and he was quite happy to just watch for a bit.
It was Michelle's turn to talk. "Shes so beautiful, I love watching you fuck her".
Her hands wandering between both their legs the mans legs and began stroking his cock and balls as he fucked his wife's hot pussy."You like this don't you?"

She leaned over and began licking under his balls and then upwards to his ass, kissing and licking it too. Between his wife's hot pussy, and Michelle's mouth and hand....it was all too much and Will recognize the guy was about to cum. Michelle knew it too, and literally pulled his cock out of that pussy and stroked him into finishing in her hand, her palm soon filled with his fresh seed.
Michelle licked an errant dribble from the side of her hand, but then what she did next took Will a little by surprise. "Want a taste?" she asked the man, and he nodded and happily licked and ate his own load from the palm of Michelle's hand, his wife looking on.
She caught Wills expression, and grinning wide she offered him a taste as well. He was relieved when she took his quick head shake no as an answer. It was really not something he wanted to try.
He noticed the wife looking at him so he made his way over to her side of the bed and presented his cock to her. Nice ice breaker Will thought to himself as she somewhat shyly took him into her mouth. It was always exciting to have a woman you had just met sucking your cock, and Will knelled above her enjoying the show. He glanced over to see Michelle getting a good pussy licking from hubby. With each of the couple busy the two friends smiled and it was a look that was JUST short of an actual "High Five" moment, but it was damn close. They were both having fun, and enjoying seeing each other have fun.
It was not long before Michelle told hubby to lay back. She hopped off the bed to grab something out of her bag, then returned and took his growing tool into her mouth. She could not quite get it all in her mouth and down her throat, but she got close a couple of times. It was not long before he was fully hard once more.
The wife knew what Michelle's wants for the evening included and sat up to watch as Will moved around behind Michelle. He could now see what she had grabbed, she had a tube of something called "Lickity Stiff" and she deftly squirted some out into her hand and reached back between her own legs spreading the cool feeling substance over the length of Wills cock. Kneeling behind her, he guided the head of his cock to her tight back door. Michelle never missing a stroke of hubby's cock in her mouth.
Will knew to be gentle, and began pressing himself into her. It seemed like it took a bit of pushing, then suddenly the head of his cock popped into Michelle's ass. Michelle didn't miss a beat, still sucking happily on the cock in her mouth. Will continued to push himself into her and soon was completely in her ass. Slowly he began to press in and out of her, and soon she was moaning a bit. The moans were familiar, pure pleasure. Sensing she was indeed enjoying what was happening she began to thrust in and out of her at a steady pace. Her ass felt very tight on his cock as he fucked her. Suddenly Michelle stiffened and moaned loudly, she was cumming. Will slowed his pace as she came, her moans muffled by the cock in her mouth, but she was cumming for sure. Will was not sure who was more surprised him or her. Hubby pulled his cock out of her mouth as she finished cumming, breathing deeply. Will pulled out of her, and watched as Michelle once more began sucking the huge cock in front of her, and beckoned him over to once again mount her.
With a bit more confidence, Will slipped his cock back into her ass once more, and other than a small grunt as he entered her, took it easily. After a few moments hubby pulled back, probably getting close to cumming himself and wanting to be able to accommodate his part of the DP when called upon.
Wife and hubby sat back and watched as Will fucked her from behind. It was not until Michelle announced,loudly, that "Oh my god Will your fucking my ass, and your going to make me cum AGAIN!!"
More surprised looks, this time from the couple. Michelle was taking the ass fucking "Like a Trooper" and they had actually not even realized what was going on, thinking Will was just fucking her pussy.
"Hes fucking your ass??" the wife asked a little stunned, and the look on hubby's face held a bit of jealousy Will thought. "Oh yes!!" Michelle answered, "and I am going to cum again!!" The wife reached over and grabbed a camera off the night stand and clicked some pictures of Michelle's tight ass filled with cock, all the while Michelle moaned and wiggled. "Harder!! Don't stop!!" she pleaded as he pounded her ass.

Will quickened his pace and announced he was going to cum soon. Michelle told him "Cum in my ass Will!!!" .Wife almost yelled "Hes going to cum in her ass!!" and the two of them sat and stared as Will pressed deep and released his hot load of cum he had been holding back all night into Michelle's tight ass, while Michelle rode out her own strong climax, trembling and moaning. Her second very different climax of the night, from getting ass fucked!

As their orgasms subsided, Will gently pulled back out of her and lay down next to Michelle. "I fucked your ass." he whispered. "Yes, yes you sure did. You came in my ass. I guess your name is on one more of the "firsts" on my list." she smiled.

Later on the way back home she explained she had realized she was not ready for both holes to be filled at the same time, and she also decided choosing two of her better endowed friends was not the best way to go for DP either. Will told her he could not blame her for that. "Oh" she added," I also wanted to thank you for letting me and them do our thing."

"It was a hot show." he answered, and still wondering had to ask. "So, hes a good hunter?" she looked at him funny. "You know, he Eats what he Shoots?" she thought about it a moment and laughed.
"Oh THAT...no that was part of the fantasy he wanted tonight. You see, his wife will NOT let anyone including him cum in her mouth, and says to him before when he asks her to try it, "You first". Soooo tonight, he ate a load. Idea being now, its HER turn to give it a try." she added "Offering it to you was just to see the look on your face." she laughed harder.



What a great memory that night made for. So, he already had Michelle's "ass virginity". So what WOULD he as for, for his "ANYTHING" prize? This would take a little thinking.

(End of Part Two)

End of Story