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Ann Loses The Bet, But Enjoys Her Loss

"Ann's ass becomes red hot when her team loses."

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3.6k words 3.6k words

Ann and Will were an older couple that enjoyed sex and exploring their fantasies. Since meeting on Lush several years ago, they had gone from cyber-lovers to physical lovers. As they became physically connected, they had found many ways to enjoy each other. They never failed to try something new in their relationship if one or the other wanted to try it. This had broadened their sexual appetites in many ways and found them always stretching the boundaries of what each other would do. Today was no different.

Will and Ann were both college basketball lovers and always debated what team was better. They would put some heat into their arguments as was happening today, Will was pulling for the underdog in the matchup and Ann was pulling for the favorite. Will always looking for a way to get the better of Ann suggested a little bet. Knowing Ann had been fantasying about being spanked, Will thought this was the ideal way to break through her reluctance of actually trying it. He felt offering up a spanking for the loser was an ideal icebreaker. He knew Ann couldn’t back away from the bet because she was sure she would win. Will decided if nothing else he would get spanked and that might lead to other fun. He figured if worse came to worse, his ass could handle it.

They were settling down on the couch to watch the game when Will said, “Ann, I have a bet for you on this game if you’re interested?”

Ann turned her head to look at him, “So, what is the bet that you are going to lose today?” she smirked.

“Loser gets spanked by the winner. I get the underdog and the points against your team. The loser gets spanked the number of times the difference between the winning score and losing score.”

Ann thought for a second and laughing, finally said, “Sure, but we better limit the number to a max of ten spanks. I’d hated to bruise my hand on your ass when you lose by twenty or thirty points today.”

“Okay, ten it is, but remember if I lose by ten on the scoreboard I get the points, which is six. That means I only get four slaps on the ass, deal?” he said.

“You are on luv. I’m going to enjoy spanking that bare ass,” Ann said with a huge smile, figuring she had this in the bag.

Will, thought for a second, “Bare ass it is babes! I always like your ass turned up to me anyhow.”

They quickly got some snacks and drinks before the game got going. Ann cuddled up to Will in the corner of the sectional. They had spent many an hour there since meeting and many an hour naked after being cuddled there. Today might not be any different, but somebody's ass may be a little spanked a little red in the process.

Ann laying back against Will had on a thin oversize t-shirt with no bra and no panties on. When she stood it would come down mid-thigh. She loved being dressed like this in the house. If truth be known, Will loved her to be dressed like this as well for obvious reasons. Will was just in a tank top and a pair of loose fleece shorts. This was his favorite outfit to hang around in the house as well.  Ann favored this on him too. They both acted like sex-starved teens and always wanted each other accessible.

The game came on and the favorite team ran up a ten-point lead from the start. The game stayed pretty steady after that, but Will had other things on his mind. He slid his hand to Ann’s thigh and was tracing his fingers on her bare skin. Ann didn’t complain, just shifted her leg to give him better reach. He slowly worked his hand to her inner thigh, tracing his fingers to the edge of her pussy. Ann squirmed a bit at his touch but didn’t say anything. She was trying to be intent on the game. With only a few minutes left in the first half, her team was still up by eight points.

Working his fingers on her pussy, Will started stroking up and down her slit. He would trail his fingers over her from the perineum to the top of her clit and then work his way back down. He could feel the heat coming from her and the moisture building as he stroked her. She squirmed against him but was trying really hard to concentrate on the game. Will decided to make this even tougher as he parted her lips and slid a finger into her pussy. He gently started sliding his finger in and out. He was in no rush, just enjoying touching her. He was paying more attention to her labored breathing as he fingered her than he was the game.

Suddenly she turned away from him causing his finger to slide from her. As she whirled around to face him, she grabbed him by his hair and pulled his mouth to hers, kissing him hard. She let go and leaned back on the couch, pulling her shirt to her breasts saying, “You wanted to excite me, now finish what you started before the game comes back on,” open her legs to show him her pussy in full view.

Never one to pass up an offer like this, Will positioned himself in front of that delicious pussy and kissed it. He ran kisses all over her pussy as she began to squirm in need. Finally giving into her, he lowered his mouth to her and slid his tongue between the lips of her pussy, pushing it deep before dragging it along her soft inner walls. He loved the feel of her inner flesh, it was so soft and supple to his tongue. She tasted so good to him as he lapped at her free-flowing juices.

He moved to her clit and kissed and licked it as he slid two fingers into the sopping pussy. He worked his fingers in and out, splaying them open to fill her full. She was so wet he added a third finger as he continued to play with her clit. He would suck it between his lips and then let it go to lick it in broad swipes of his tongue, all the while working her pussy with his fingers.

Sensing how wet and excited Ann was, Will decided to try something on her he had always wanted to. He worked his fourth finger into her pussy, slowly moving it in and out with the others. To keep Ann distracted until it was too late, he continued his manipulation of her clit. When he felt he had her relaxed enough he curled his thumb into his palm as he’d seen in the videos. Slowly pushing against her pussy opening, he felt his hand sliding in. just as he was close to being fully in, he sucked hard on her clit causing Ann to moan loudly and raise her hips. This was just the perfect moment for Will to slip his fist into her.

Ann, let out a moaning gasp as his hand slid into her pussy. She rolled her head back and was moaning out loudly as he started to move his hand back and forth inside her pussy. He had it balled up into a fist and was pushing as deep as he dared before drawing it back to her opening. Every time he did this, Ann would shiver and moan louder. WilI continued fisting her for just a few more minutes before her body tensed up and she screamed out she was cumming! Her pussy tightened on his fist and he held still, not wanting to hurt her as she orgasmed on my fist. He couldn’t withdraw until she had relaxed.

She had a large amount juice flow from her over my arm and onto the couch. He had watched videos of a woman squirting and though he don’t think this was it, she surely had a larger release than ever before. WilI had juices dripping from my forearm and could see it running down her ass to pool on the couch under her. He was amazed at what just happened. As Ann started coming down from her powerful orgasm, he opened his hand to slide it out of her pussy. He was gentle as possible and she was so wet he slid right out with an audible squishing sound as juice trapped behind his fist came running out adding to the mess on her and the couch.

Grabbing for the first thing he could reach, Will grabbed a towel that was had on the couch for our snacks. He quickly ran it over her swollen and engorged pussy, drying up some of the mess left on her. He ran it across his arm and hand. Then finally dropped it on the huge wet spot created on the couch.

By this time, Ann was recovering from her overwhelming orgasm and trying to sit up but was a bit wobbly. WilI reached out and offered her a hand, the same one that had just been pulled from her pussy. She gasped and then instantly pulled away looking at it.

“Sorry Luv, here.” He offered her my other hand and she took it, pulling herself to a seated position.

“My God Will, what did you do to me. I felt so full and overwhelmed at the same time.” She knew what he had done, but it was just not settling into her brain yet she had just been fisted to orgasm for the first time.

Will looked a little sheepishly at her and replied, “Slid my whole hand into your pussy and fucked you with it.”

She just sat there and stared at him for a full minute before leaning forward and kissing him. She pulled back after a quick forceful kiss saying, “That felt so amazing!”

They both had forgotten about the game they had the bet on until they heard the announcer say that the underdog team had just taken the lead in the game with less than five-minutes to go. They both looked over and saw the score was just about even. Will looked at Ann and smiled. She looked at him and glared.

Will stood up and offered his clean hand to Ann to help her up. She took it and stood facing him, leaning forward giving him a kiss before saying, “I think I need to clean up.” Looking at the couch and the mess hiding under the towel, she said to Will, “I think you need to clean up as well,” and she walked off towards the bathroom. Will picked up the towel and looked at the big wet spot and decided that would get cleaned up later with the shampoo cleaner and he went to the kitchen to wash his arm off and get them fresh drinks to finish watching the game. He hoped to be the winner!  

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Will and Ann settled back down to finish watching the game. Ann was screaming at the television within minutes because her team was losing and the points gap was getting bigger. Will wisely stayed quiet but was jumping up and down on the inside. He just couldn’t wait to get Ann bent over bare-assed and spank her luscious ass. She was a woman that had just enough meat on her bones to give her that perfect ass to stare at as she walked away, but at the moment, Will was more interested in spanking it.

Ann was on her feet now screaming so loudly at the television that the neighbors surely heard her. The game was down to the last seconds and her team was losing seven points. She knew that meant she was in for ten whacks on her bare ass and Will was going to gladly apply them to her. She was still screaming as the last second clicked off. Doing the quick mental math in her head, Ann realized she was saved by the few last minutes points her team scored. Will with his six points added to the score, left her getting seven whacks on her bare ass. Her team lost, but at least it was only by one.

Finally turning to look at Will, she could see him smiling like that the cat that ate the canary. “You bastard, you are going to enjoy this aren’t you?” she snarled.

Will just smiled and rubbed his hands together. Ann just stood there watching him with a very apprehensive look on her face.

Finally speaking, Will asked her, “Would you like to get this over with now or later?”

Taking a deep breath before answer, Ann finally said, “Now and you better not enjoy this to damn much buster!”

Will stood up and slid the ottoman over in front of the couch. “You can bend over this. It’s just the right height that you can rest across it with your knees on the floor and your ass in the air.”

Resigned to the fact Will was actually going to follow through on the bet, she lifted her t-shirt off and dropped it to the floor. This caused Will to almost forget about the bet and go for better things. He just couldn’t take his eyes off her standing there. Her breasts full and heavy from age were the perky little things the young chicks flaunt, but he loved to play with hers. Her nipples were so sensitive that he had almost driven her to orgasm by just playing with them. He moved his eyes downward, she had a bit of paunch, but hell, so did he, but the real icing on the cake was hidden by her natural blonde bush. Her pussy was so like heaven to him. He could spend hours eating, licking and sucking that sweet nectar from that pussy.

Being caught ogling her, he heard her say, “Nimrod, are we going to finish this or what?” She was starting to kneel down over the ottoman facing away from him with her ass lifted to him. He moved his hand to his cock and shifted it some in his shorts.

Walking over to her he was trying to decide the best angle to get a full swing on her ass. “You ready?” he asked.

“No, but get it the fuck over with!”

Thinking to himself, in for a penny, in for a pound, and with that he landed the first of his seven whacks on Ann’s right cheek causing her to let out a yelp. The second blow landed on her left cheek and this brought a louder yelp from her and the realization that he was going to carry through on the bet. No sooner than the thought made through her mind the third whack landed on the right cheek. This time she cried out and had tears starting to form in her eyes. The fourth landed on her left cheek causing her to start sobbing as tears ran down her face.

Ann never thought he would spank her, let alone do it with such force to cause her to cry out. Ann knew she still had three more whacks to go and saw no chance he wouldn’t deliver them, but one. Weakly she said, “Please Will, I’ll do anything you want if you stop now.”

Will was just about to bring his hand down again when she turned her head and asked him to stop. “Why should I? You would’ve enjoyed doing the same to me if I had lost.”

With the break in the moment, Will looked down at her ass. It was red and the left cheek had a solid impression of his hand. Then looking when he moved a bit he could see the side of the ottoman. It was a light brown in color and had a huge wet spot spreading down the side of it. Looking even closer he could see Ann’s pussy glistening with her juices. He decided then that she was getting her last three whacks. He quickly administered them before she could recover, applying them as equal as possible to each cheek.

Finally finished, he knelt down next her and rubbed her low on her back with one hand and her face with the other as she recovered. As he stroked her face, calming her, he was slowly working his hand on her lower back to her ass, rubbing each cheek. Ann was calming down still half laying over the ottoman as Will slowly worked his one hand over ass until he made contact with her pussy. He could fill how wet she was. Whether she would admit or not, the spanking had turned her on.

Will slowly started tracing his fingers over her pussy. This caused Ann to jump and moan, but she looked at him without speaking, but with a look on her face that said, “Really, you are going there?”

In reply to her look, he slipped a finger into her pussy as deep as he could. This caused the reactions he knew it would, her moaning and pressing her face into his hand. Then finally pushing her pussy onto his finger as far as she could, which wasn’t far. He already was as deep as the position allowed. He pulled it out a short way before thrusting it back in. He was steadily repeating this and Ann was responding by moaning, no longer angry over the spanking. She let her head drop from his hand and hang as she moaned to his rhythm of fingering her.

Will, not having had any action today, kept his finger fucking motion going, but moved behind Ann. He used his free hand to push his shorts down his legs and kicked them off. Ann was moaning so hard now, she never realized Will was stripping behind her. He pulled his finger from her and she flexed her ass up, trying to find that finger. Instead, she felt Will pushing his cock into her. A prolonged moan escaped from her as he pushed all the way in.

He started thrusting into her harder, he stripped his tank top off to be totally nude as well. Finally placing both hands on her hips, he pulled her back just a bit, making a better angle to enter her pussy faster. He was pulling almost all the way out before plunging back in, over and over. Ann was moaning and pushing back at him, trying to meet every thrust, until suddenly she screamed, “I’m Cumming!” arching her back to get Will in as deep as she could. Will for his part, pushed all the way in, feeling her pussy tighten around him. He knew how strong her orgasm was because he could feel her juices running down his thighs.

As soon as she calmed down and relaxed, Will went right back to fucking her hard and fast. He was as mercilessly fucking her, just as he had shown no mercy spanking her. He stopped long enough to roll her over to her back. Leaving her resting on her back, pulled her legs up and over her shoulders, plunging his cock back into pussy. His pace was fast and hard. Ann was squealing through another orgasm as Will kept banging her pussy.

Will could feel his orgasm coming on quickly and pulled from her pussy. He moved around to her head that was hanging off the side of the ottoman. Ann seeing his intention, reached out over her head and grasped his cock. She guided him to her mouth, taking him instantly deep. In the position she was in, it allowed her to slide him into her throat before pushing away. Reaching for Wills' hips, she moved him in and out of her mouth and throat at a pace she controlled.

Will was beyond control and thrust his cock deep into her throat one final time, unleashing his load of cum straight down it. Ann gagged and pushed Will back just as another rope of cum shot from his cock. Not being able to handle any more in her mouth, she let it drool out the side, streaking it down the side of her face. Will, sensing she needed him to pull back, withdrew from her mouth just as the last of his cum shot out, landing on her forehead and running down into her hair.

Ann rolled to her side and coughed hard, spitting some of Will’s cum on the floor, before dragging in a deep breath. Will seeing her having a problem immediately knelt down next to her asking, “Are you okay babe?”

Ann, taking a few deep breaths before finally replying, “I’m fine, just got a little choked on you.”

Will cradled her head and helped her to a sitting position on the ottoman. Ann rested there for a minute before looking up at Will. She had cum all over her left cheek where she had let it drool out, cum on her forehead, streaked to her hair and some on her chin from spitting it out on the carpet. Will thought she looked a mess but was sexy as hell and couldn’t be happier to have her in his life.

 

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Written by Road_Runner
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