Infidelity Revisited Ch. 08

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He challenges her to a game and they both win.
3.4k words
4.62
47.7k
11

Part 8 of the 19 part series

Updated 11/01/2022
Created 09/27/2002
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When she got to her room, Charmaine pulled her cum-stained shirt off, becoming naked except for the kerchief in her hair and a brown colored sports-bra. She took the kerchief out of her hair and her long hair fell down around her shoulders. Unbeknownst to her, Ryan was stripping behind her.

“Take off your bra and let’s lie in bed naked, and watch TV.” He said, mischievously as he turned on the television in her room. Still a conservative woman, she felt very uncomfortable being naked with this man in a non-sexual environment. She hesitated.

“C’mon!” he encouraged. “Let’s see how long we can keep our hands off each other. First one to touch the other’s private parts loses!” She smiled, relaxing a little. Her pussy tingled.

“What do I get if I win?” she asked. Ryan appeared to think for a moment.

“Anything you want. I’ll be at your service for a week.” He replied, “No matter what I’m doing, no matter when. I have to have sex with you whenever you want.” It was an easy concession, since it’s probably the case anyway!

“And if I lose?” she asked, cunt buzzing a little more urgently.

“We try anal sex again.” He answered, as if that was his plan all along. Actually, he had just thought of it, and thought it would be a fantastic prize!

Charmaine smiled, and nervously reached beneath her breasts and pulled up her bra, freeing them. She pulled it over her head and dropped it on the floor. Completely nude, she hopped onto the bed. ‘SQUEAK!’ There goes her bed again! It was a good thing nobody else was home!

Ryan pushed down his shorts and underwear, freeing his semi-hard dick. He lay down beside her and they watched TV, smiling happily. He wouldn’t have stood a chance if he hadn’t cum twice in the past hour. Now, he felt like he could easily beat her!

As the minutes rolled by, she found herself glancing down at his penis more and more. It was fully soft now, but even in that state, it was still quite big.

She squirmed a little, squeezing her legs together. The show was boring, she began to change the channel. Boring, boring, boring. She finally left it on the original channel. Her eyes again strayed to his cock. She could feel herself getting wet again.

Ryan, meanwhile, made the mistake of looking over at her. That gorgeous body of hers captivated his gaze. His eyes trailed up and down, taking in every inch of her body. He could feel movement down below. He looked at the clock. It had been a little over thirty minutes. He had to be strong. He really wanted to try anal sex with this goddess again.

She caught him looking at her, and she smiled. He kissed her, lips smacking. She kissed him, holding her mouth against his. Her tongue forced its way inside. They kissed passionately, tongues exploring. It took all his strength to not caress her breasts.

Charmaine turned to him a little as they kissed, and she placed her hand on his taut stomach. Her touch sent bolts of electricity through him, and his cock responded. Out of the corner of her eye she could see his dick grow rapidly. As her tongue rubbed along his, his manhood grew to full hardness. It was sticking up into the air, pointed towards them.

Almost out of habit, she reached for it, before she caught herself. He wasn’t going to win that easily! She closed her eyes, forcing herself not to look at that beautiful penis of his. That was best way to resist temptation.

Ryan broke the kiss, his breathing labored. It was impossible to not touch that perfect body of hers! He had to stop kissing her or he would lose for sure. She was watching him as he tried to watch TV. If there was something of interest on, maybe the game would have lasted a bit longer.

Neither could take it.

Charmaine desperately wanted him to be her slave for a week. And she was beginning to think that letting him in her ass again isn’t all that bad. She turned to him.

“Do you want to just say we both win?” she asked, smiling.

“Fuck, yes!” he said, pushing her onto her back. The bed let out a loud squeak again, their every movement could be heard. He squeezed a leg in between hers, and Charmaine opened her legs for him allowed him to mount her. His mouth was on hers, and the head of his penis was rubbing along her slit on its own accord.

As she sent her tongue into his mouth, she rubbed her pussy along the shaft of his dick until her entrance gripped his tip. He pushed hard, animal instinct taking over. His manhood eased into her tightness, sliding most of the way inside in one stroke.

“MMMMPH!” she moaned into his mouth as her warmth gripped him. He pulled out of her a little before sliding his entire organ deep inside her tunnel. She wrapped her arms and legs around him, holding him tightly, keeping his big, thick cock inside her needy cunt.

Ryan broke the kiss and looked down at her. She was looking at him with such need, such desire. The heat of her pussy held him tightly, and his cock seemed to grow even harder at the sensation.

Charmaine could feel every inch of that rock hard penis inside her. It was so big, it stretched her so wide that she could tell just how fully hard he was. It was like having a thick dildo made of stone inside her!

His eyes trailed down her amazing, tanned body. Her chest was heaving, her beautiful breasts rising and falling. Beneath her smooth belly he watched as he slid his long pole out of her horny pussy. The cool air hit the moisture on his penis. He slowly slid back inside her warmth.

“Ohhhmmmph!” Charmaine’s moan was cut off by his mouth as he kissed her soundly. He began to slide his manhood in and out of her. She slid her hands down his body to his ass, and her feet slid up his legs to his thighs as he entered her over and over. She could feel his ass tense up in her hands every time he clenched, thrusting his big cock into her needy hole.

‘SQUEAK! SQUEAK! SQUEAK!’ Normally the bed’s loud squeaking would be cause for distraction, but the lovers were so involved in the heat of passion that it was but an afterthought.

Ryan paused briefly, reaching down and sliding his arms under her legs, putting them up on his shoulders. Now Charmaine was truly at his mercy.

Her feet were on either side of his head and over nine inches of his cock was in her tight little cunt. He looked down at her as he pulled his cock back, almost to the point where it popped out of her. The mushroom head of his organ was stretching her pink lips wide.

He smiled down at her, teasing her as he held her at the edge of heaven. She was dying to have him sink that pole all the way back into her. She was begging him with her eyes. He turned his head and kissed the inside of her foot. He turned the other way and did the same thing to her other tanned foot.

Suddenly, he rammed his penis into her. “UNH!” she cried so loud it drowned out the noisy squeak of the bed. He was sheathed inside her warmth, but not for long. He pulled most of the way out of her before slamming himself back in. “UNGH!” she moaned, eyebrows raised. Bolts of pleasure violently shot up her body at the incredible sensation of his dick sliding into her so hard.

He fell into a rhythm, and it wasn’t a slow one. He fucked the helpless girl for all he was worth. Charmaine’s ankles were on his shoulders and all she could do was take everything he was giving. Her tits were bouncing, she was crying with every thrust.

‘SQUEAK! SQUEAK! SQUEAK!’ went the bed. To make things even louder, the headboard was ramming against the wall!

She didn’t care. All that was happening in her world was this huge cock was slamming into her needy pussy so hard it was driving her to the edge very quickly. “UNH! UNH! UNH! OHH! UNH! … OHHHHHHHHHH…OHHHHHHH!” Charmaine yelled, cumming. Her heart was pounding, she could feel her entire body grow hotter. She nearly knocked the big man off of her with her exertions!

She was wincing, gritting her teeth as the inner walls of her pussy convulsed around him. Ryan continued to pound into her pussy mercilessly, rocking the bed with his hard thrusts.

Finally, he slowed down, allowing her legs to fall from his shoulders. He kissed her open mouth as she gasped for air, still sliding in and out of her at a calm, steady pace. She was in heaven. Orgasm after orgasm he gave her that day, and he still felt so wonderful inside her! After a few moments of making love slowly, Ryan pulled his long organ out of her vagina. He kissed her softly on the mouth.

“Get on your stomach.” he whispered. Charmaine’s heart dropped. She was more than a little frightened. The time was almost at hand. He would try, once again, to enter her ass. Her pussy seemed to grow wetter at the thought, but she still could not stop the fear. She was his slave, she realized. Everything that she did was to please him. She rolled onto her stomach. Ryan caught his breath.

There it was.

The nicest ass he had ever seen. Perfect size, shape, skin tone. There was even a tasteful tattoo just above it, purposely creating a flaw to bring out the perfection. He kissed her ass cheek. He kissed her other one. He grabbed a cheek in each hand, squeezing them, caressing them.

He began kissing all over her ass as his hands kneaded her cheeks, spreading them apart. His kisses drew closer and closer to the crack of her ass. He spread her cheeks wider, exposing her asshole to him.

Charmaine felt so helpless as she felt him kiss, and manipulate, her ass. She felt flattered, though, and his attentions turned her on nearly as much as his body did! She could feel his lips kiss along the crack of her ass, and her heart sped up.

Ryan stuck out his tongue, and ran it around the entrance to her tight little anus. She sighed, squirming beneath him. He slid his tongue into her tight little hole, his hands still holding her cheeks apart. She was still not used to the sensation of feeling his nimble tongue roll around the inside of her ass – but she liked it. The feeling sent tingles into her pussy, and that was always welcome!

He kissed her ass again, and kissed up her spine, sending chills through her body. Her legs were parted slightly, and she could feel him run the head of his cock down her ass to her pussy. She was lying flat on her stomach, head turned to the side as he kissed her cheek, running his thick penis down her slit.

He forced the tip of his penis into her, and she gasped. Ryan continued pushing, and Charmaine could feel her vagina stretch open wide as his penis squeezed inside inch by inch. He kept going until he could go no further. He was sheathed entirely inside her pussy. He lay that way, on top of her, inside her, kissing her cheek.

“Can I go in your ass?” He breathed.

“Yes.” She replied. He really had her all worked up, and she found herself wanting more than his tongue in her ass. She didn’t think she was ready to try again, but she desperately wanted to.

“Do you have Vaseline?” He asked.

“Yes, in the bathroom in the cabinet.”

Ryan pulled out of her wetness with an audible ‘slurp’. She suddenly felt so empty! She needed him back inside her!

When he walked back into the room (after what seemed an eternity), he noticed that Charmaine was still lying on her stomach. His cock was sticking straight up in the air, and it noticeably twitched when he saw that amazing ass of hers.

He set the jar of Vaseline on the nightstand and knelt between her legs. He grabbed her by the hips and gently raised her to her knees. Her heart was pounding.

She was very excited. She had no idea what he was going to do next! Oh, she knew she was getting it in the ass at some point, she just didn’t know when – or if he would do anything else to her first!

He bent and kissed her ass cheeks again – he couldn’t get enough of it! He spread her cheeks once more, revealing her puckered asshole. She was breathing laboriously, bent over before him as he stuck his tongue out and licked from her pussy, up the crack of her ass. He slipped his tongue into her tight little hole again. “Ohhhh…” she moaned softly, squirming before him.

Kissing her ass one more time, he got up behind her, holding his rock hard dick out and placing it at the entrance to her vagina. He pushed forward. Charmaine was so wet that her pussy sucked him inside hungrily.

“Ohhhh God yes!” she sighed as his long penis slid into her all the way in one solid thrust. He grabbed the soft sides of her ass and held her still, pulling his cock halfway out of her. He pushed back in, and began to take up a steady pace of sliding in and out of her.

‘slap slap slap slap slap’ her ass cheeks shook each time his groin slapped against them. “Unh! Unh! Unh! Unh!” she moaned as her cunt filled with cock over and over. Her breasts rocked back and forth beneath her as she moved with the rhythm of their sex. Ryan slid inside her all the way, holding himself there. He reached above her to the nightstand, grabbing the jar of Vaseline.

Without using his hands, using only his hips, he resumed fucking her from behind. At the same time, his hands opened the jar and he scooped some lubricant onto his finger. He set the jar down, reaching between them with his hand.

He pressed his finger against her anus as he held his groin back out of the way, his cock remaining halfway inside her. His finger slid into her ass, coating her hole with the lubricant.

“UNHMH!” she moaned, eyes closed, wincing. And that was only his finger! Maybe she wouldn’t be ready…no, she decided, the pain wasn’t as bad, and the pleasure was definitely much more apparent this time. She would stick it out.
Ryan pulled his penis out of Charmaine’s vagina, and his finger out of her ass. His cock was already lubed with her juices, but he rubbed a bit of lubricant on it anyway.

Heart pounding, she bent over further before him. She knew it was coming now. He likely was not going to beat around the bush anymore! She opened her legs a little further and tried to relax. Her entire body was tingling with anticipation, and a little bit of fear.

He placed the fat head of his penis against the lubed up hole of her ass. He pushed forward. Harder. A little harder still. Charmaine’s asshole opened up and allowed the head of his cock inside.

“UHHHHH!” she cried out, wincing. She tried to stay relaxed, but he was splitting her body in half!

“Go slow!” she grunted. Ryan was so hard. He looked her sexy body up and down. From the bottoms of her tanned feet on either side of him, up her smooth legs to her amazing ass. Her asshole made the top two inches of his dick disappear. Above her ass was a little tattoo. He pulled his dick back out of her. She felt relief, yet despair. She actually missed having him in her ass!

He put it back at her entrance and pushed forward again. This time it went in much easier, and he slid a tiny bit further inside.

“Ohhhhhh fuck!” she swore, face clenching. It felt so good! The pain was there, but in the background this time!

Ryan began to slide three or four inches of his cock in and out of her asshole, at a slow but steady pace. Her anus was gripping him so tightly! He was having a hard time just getting a few inches in there! He reached around her, cupping her pussy with his hand. His finger began to diddle her clitoris.

“OHHHH…” she cried, bolts of pleasure shooting up her spine. She now felt absolutely no pain. Her ass felt incredible. Her pussy felt incredible. Her orgasm was rising rapidly from within.

Sensing this, he went a little faster, easing a bit more of himself into her ass as he did so. More than half of his dick was sliding into her anus now. “Oh! Ohh! Unh! Unh! Ohh!” Charmaine moaned, her head was resting on her arms as she stuck her beautiful ass up at him.

“OHHH…UNMHHHH!” She groaned, cumming. Her pussy was convulsing as his hand rubbed it. Her ass was convulsing as his dick fucked it. Her entire body was on fire, her heart was pounding a mile a minute as she came violently. Her orgasm was so intense that she didn’t notice Ryan sliding a sixth, and then a seventh inch into her asshole.

He was now inside her further than he had ever been. He was using long, slow strokes, most of his manhood gliding in and out of her tight ass.
Charmaine whimpered before him, trying to recover. Her bum was hurting again. He was really going in her deep! She could not deny, however, that it still felt amazing, despite the pain.

Ryan was watching his penis glide in and out of her beautiful ass, and he pushed into her a little bit further. “OHHH!” she moaned. “So big…” She tried to relax, eight inches of manhood sliding in and out of her anus.

He did not yet dare to use long strokes, keeping it in her ass fairly deep and using short thrusts. For the next minute or so, all that could be heard was their heavy breathing and the squeaking of the bed. Charmaine was focusing on the feeling, trying to ignore the pain and embrace the pleasure. She was succeeding.

He took a chance, pushing his penis all the way inside her tight asshole, holding his groin against her ass for a moment. “Ohhhh fuck!” she cried, grimacing. His entire cock was buried in her anus!
He slid most of his manhood out of her ass and slid back in. “OHHHH…OHHHHHHGOD!!” she yelled, an orgasm washing over her, catching her off guard. Danny, Charmaine's boyfriend of four years, has never felt what Ryan was feeling that very moment - what it was like to be inside Charmaine's ass.

Ryan had a tight grip on the sides of her ass, using long, steady strokes as he slid in and out of her backdoor.

Her heart was pounding, her eyes were closed, helpless as she got fucked up her ass. He was moving faster now, sliding most of his cock out of her before jamming it back in. Her ass cheeks were shaking every time he bumped into them. He was losing it himself, overwhelmed by the sight and feelings. He fucked her faster, his thrusts long and hard.

“UNH!” he moaned, jamming his penis hard into her little ass and holding it there. Charmaine was gasping for breath, on her hands and knees before him, wincing in pain and ecstasy as his dick jerked violently in her asshole.

She couldn’t have pulled away if she wanted to. He was holding onto her ass tightly as he ejaculated inside it. His cock spasmed again, another thick load of cum firing deep in her ass.

Ryan nearly collapsed on her as the last of his cum trickled into her. He pulled his softening penis out of her ass, and she fell forward, moaning. Her ass hurt, but she felt really good. She needed to be fucked, and he gave it to her three times! For the first time since she met him just over a week ago, Charmaine was actually completely satisfied.

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AnonymousAnonymousabout 3 years ago
excellent sequel

This chapter is not a stand-alone story. It continues directly from the previous chapter, and makes little sense on its own. To those readers who regard Charmaine as nothing more than a "slut", this reviewer recommends reading My Girlfriend's Best Friend, to see what Danny is up to at the same time that Charmaine is with Ryan. Danny is shown to be no innocent victim, and, unlike Charmaine, has far less inner turmoil about what he is doing than has she. The complexities of the relationships in this saga, and the ongoing emotions and inner turmoil involved, make for a gripping drama, of which this chapter is a small part.

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