The Taming of a MILF Ch. 05

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Tyler and Tommy degrade Sandra even further.
4k words
4.52
69.1k
54

Part 5 of the 7 part series

Updated 06/07/2023
Created 07/07/2015
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Sandra walked into the Country Club clenching her pussy, trying to keep Tyler's cum from running down her inner thighs. But in spite of her situation, she liked the feeling. It made her feel naughty knowing she was walking around with some young studs seed inside her. Damn that Tyler knew exactly how to push her buttons. When he had first forced himself on her, she had felt nothing but revulsion at the thought of being used as his sex slave. But since then she felt like she had been on some kind of emotional rollercoaster. One side of her hated what Tyler was forcing on her. The other side of her was drawn to it like a moth to the flame.

"Hey Sandi!" Her friend Cynthia greeted her as she approached the table. "You're late! So where were you shopping this time?" She asked laughing.

"I don't think she was shopping anywhere!" Her friend Dena chimed in teasingly. "I think she was playing with her boy toy!" The only two subjects the three friends talked about when they were together was shopping and sex.

Sandra hesitated before responding. Then she stammered slightly trying to formulate an answer. "I was . . . ."

Dena cut her off. "I knew it! I can see it on your face! You did get a good fucking, didn't you!" She almost whispered as she leaned across the table so as not to be heard by the other patrons of the club. Both Dena and Cynthia smiled at her waiting for a reply. Both ladies were pretty much in the same situation as Sandra. Wealthy husbands who kept them as trophy wives. Whenever the three friends got together they enjoyed sharing their sexual exploits, always trying to out do each other. "So did Tommy scratch that itch for you this morning? Did you finally let that boy stuff that under used pussy of yours?" Dena and Cynthia giggled as they awaited Sandra's story. They had known about Sandra's boy toy for a couple of months.

Sandra thought quickly. She decided to tell them part of the truth, but not all of it. She wanted them to think she was still in control of everything. "If you must know," she said teasingly, "it was Tommy's brother Tyler. He's quite the stud, and a lot more muscular than Tommy." The waiter stopped by and she gave him her drink order.

Cynthia leaned in when he left. "OK! So? Tell us everything!"

"We've met a couple of times. He's quite proficient in bed, and just as obedient and eager to please as his brother." She couldn't bring herself to tell them she was being blackmailed into submission to him. "It had been so long I've had a cock inside me, I decided to let him fuck me! He's quite good!" The thought of her friends knowing she was being used by some young stud was too humiliating for her to think about.

"You dirty girl! Where do you find all these young studs at?" Dena asked.

"And when are you going to share them?" Cynthia asked teasingly.

"You know they're my neighbors. Tyler is home for summer break. And NO I'm not going to share them!" She giggled as she wanted to believe her own lie. She desperately wanted to regain control of her life.

"That's not fair!" Dena scolded her. "Did you forget you promised us that you were going to share Tommy with us sometime in the future?"

"No! I didn't forget! It's just that . . . . well, things have changed. That's all."

Dena and Cynthia stared at Sandra and kept quiet. They knew something was wrong. "Are you going to tell us what's going on?" Cynthia asked.

"Maybe someday. Not today! Now let's eat something. I'm famished."

Thirty minutes later Sandra's phone chirped she had a text. She knew it was from Tyler. It was. "Be at my place tomorrow after hubby is gone. My folks will be gone." Was all it said. Sandra's stomach knotted up as she read it. Was it excitement or fear? She didn't know anymore. What she did know was that this young punk was having an effect on her she didn't like.

Sandra lay in bed early the next morning faking as though she were asleep as she listened to Sam shuffle around getting ready for his next business trip. As he was heading out the bedroom door he turned. "I know you're not sleeping. This trip will be a little longer than usual. Probably two weeks. Try not to miss me too much." He said sarcastically. Sam had often thought about divorcing her. He had even spoken to a divorce attorney. But when he was confronted with the reality of what it would cost him financially, he backed away from that idea. It was cheaper just to leave things as they were. So they continued to live their separate lives.

Sandra cried as she heard the front door close. How did their lives get so fucked up? Their lives seemed so perfect when they first got married. Then they just drifted apart like so many other couples had done and Sandra adopted new priorities. Now the most important thing to her was maintaining the lifestyle she had become accustomed to. The thought of losing her status and possessions was more repulsive to her than anything Tyler would demand of her. And she knew that Tyler knew that.

She heard her phone chirp again. She didn't care anymore. "I know hubby is gone. I expect you by 9:00. Don't disappoint me!" Was all the message said.

Sandra walked between their two backyards as she made her way to Tyler's. She wanted to avoid using the front door as much as possible. She had done so the day before and had kicked herself afterwards for being so foolish. Her heart was pounding in her chest so hard she felt a headache coming on. Was it excitement or fear?

Tyler saw her coming and opened the back door. "Why the back door?" He asked smirking, knowing the reason.

"I don't want to give the neighbors anything to talk about. At least that's what I'm trying to avoid." Sandra said as she stood on the back porch. "Are you going to let me in?" She asked as she looked around nervous at being seen.

Tyler stared at her smiling. "After you strip naked."

"WHAT!? Are you fucking kidding me?" Sandra's anger shot through the roof. "No fucking way!"

Tyler quickly slapped her across the face. Not hard enough to leave a mark. But hard enough to sting and shock her back to reality. He then reached for the top of her blouse with both hands and ripped it apart. Buttons went flying all over the porch. Without hesitating he continued to rip at her blouse until it was completely shredded and torn from her body. Sandra tried to ward off his tearing at her clothes, but it was useless. Tyler was too big and strong for her. He then ripped her bra off and threw it inside the house. "Should I keep going?" He asked her, his tone menacing. "Or are you going to do as you're told?"

Sandra stood there trembling. She began to sob as she unbuttoned her jeans and peeled them off her legs. She was a defeated woman. But she still couldn't help but look around to see if anyone was watching. Wondering who might be watching her shame and humiliation.

Tyler knew exactly what she was thinking and feeling. "Afraid of being seen?"

Sandra just nodded her head as she took off the rest of her clothing.

"Doesn't matter if someone sees you or not. Everyone in the neighborhood knows you're a worthless whore. Do as you're told and I'll take care of what the neighbors might say or think." He stepped forward and got in her face. "Defy me and I'll ruin your life." He then reached for her tits and lifted them, savoring their size and weight. Then he stepped back. "Get on your knees slut. You want to be in the house? Crawl in like the worthless whore you are." Sandra sobbed harder as she dropped to her knees and began crawling to the safety of the house, hoping no one was seeing her humiliation.

Tyler watched her crawl past him laughing. He bent over and slapped her across the ass. "Faster bitch! I think I see one of the neighbors!"

Sandra screamed and began to bawl like a baby as she scurried into the back door on all fours, causing Tyler to laugh even harder. He followed her into the kitchen as she continued to crawl. "Crawl right on into the living room and stay on your knees when you get there. Tyler poured himself another cup of coffee and followed her into the living room. He fell into his favorite easy chair and watched Sandra as she stayed in the middle of the floor on all fours. Her head hanging in shame and defeat. Her sobs barely audible now.

"Get over here." He said quietly. Sandra crawled over till she was between his spread legs. She sat back on her legs, but kept looking down at the floor. She couldn't bring herself to look at her tormentor. "Look at me!" He demanded. Sandra looked up. Her cheeks were covered in mascara from her tears. "I'd go easy on you, but somehow I think you crave this. I'm beginning to think you're a slut who needs to be taken hard, humiliated and degraded. Is that true?"

Sandra knelt silently, not wanting to answer either way. She loathed everything about what he was doing to her. And yet deep down inside there was something about the humiliation and domination that she felt herself drawn to, like an addict who needs their next fix. The excitement of the experience. The complete loss of control. The complete domination of a man over her complete being. "What is happening to me?" She cried out within her mind. "I do love this! I do! Oh god, what have I become!?"

Tyler leaned forward. "Answer me slut!" He said through gritted teeth.

Sandra had difficulty focusing on this young man who now wielded a power over her she'd sworn would never happen, her eyes filled with tears. "Yes! It's true!" She moaned softly, not wanting to hear her own words coming from her mouth.

Tyler sat back. "Then let's begin again." He wanted to humiliate and condition her at the same time. "Repeat after me! I am a worthless slut who is only good for being fucked and used!" Sandra tried to drop her head before speaking, not wanting to look Tyler in the eye as she spoke. This was only one more step in his degrading and breaking her. "Look at me when you speak!" He commanded.

Sandra looked up defeated. "I am a worthless slut who is only good for being fucked and used."

"I am a cheap whore to be used however my owner wants to use me!" Tyler said, determined to break her.

"I am a cheap whore to be used however my owner wants to use me."

"Tyler owns me and I will obey whatever he tells me to do!" Tyler said smiling.

Sandra hesitated. Tyler reached out and slapped her across her tit. Sandra jumped from the sting. "Tyler owns me and I will obey whatever he tells me to do."

"Again!"

"Tyler owns me and I will obey whatever he tells me to do."

"Again!"

"Tyler owns me and I will obey whatever he tells me to do."

"Again! And keep repeating it till I tell you to stop!"

"Tyler owns me and I will obey whatever he tells me to do." Sandra settled into almost a chant as she repeated her new mantra over and over.

Tyler sat back in his chair smiling. He had this bitch right where he wanted her and he was going to use her in every way he could. Maybe even make a few bucks off this slut's ass. After hearing her repeat her mantra for about the twentieth time, "That's enough!" He stared down at her with satisfaction. He stood. "You know what to do." Sandra reached for his buckle and loosened his pants, lowering them. Tyler stepped out of them and then sat down. "Now use those cow tits of yours!"

Sandra leaned forward and stroked his flaccid cock with her tits, bringing it to life. Tyler leaned back in his chair enjoying the sensations her warm soft tits were giving him. He watched her as she used her body the way he intended for her to be using it. He decided right there he was going to keep her as his bitch for as long as he could. For years if possible. A slut with her looks and body shouldn't be allowed to get away. He knew the only way to maintain his control over her well beyond the blackmailing was to get her to really think and believe she belonged to him. Train her like the bitch that she was. What at first started out to be a bit of revenge for what she had done to his little brother was now a deep desire to really own this woman and keep her for himself. He knew that would require the right balance of tenderness and harshness. The tenderness for when she needed to be rewarded. The harshness for when she needed to be punished. With the right combination, it would be just a matter of time before she belonged to him. Then he wouldn't need to blackmail her. He knew she needed a strong, dominating hand. He'd give her what she needed and slowly break her will, making her his bitch.

"You are a gorgeous woman!" He said tenderly, stroking her face gently like a lover.

Sandra looked up and smiled at the compliment. "Thank you!" She whispered as she continued to stroke the length of his now stiff manhood with her tit flesh.

"I've always thought you were a gorgeous woman. Since I was in my early teens. I thought you were the sexiest lady in our neighborhood."

Sandra was so taken back by the compliment she began to converse with him as though they were two lovers. "Did you really?" She giggled. "Is that why you always found something to do outside whenever I was sunbathing in the summer?" She giggled some more.

Tyler smiled. "I was that obvious? Huh?"

"Yep! But I liked it!" She wrapped her tits around his cock and pushed them together, stroking the length of it like a woman trying to please her man. "Most women like to be noticed." She now cradled his cock between her tits loving it as best she could.

Tyler reached down and cupped her chin, raising her head so she would have to look him in the eye. "I can be tender. And I can be harsh. The choice is yours. Do you understand?"

"Yes! I understand!" She said softly. But even as she spoke, a voice in her head was screaming, 'WHO THE HELL DOES THIS PUNK THINK HE IS!?' Then she realized the voice was getting softer and more distant. He was slowly breaking her down, and she knew it. But she didn't care. "I like it when you're tender with me."

"Then be a good girl and obey me! Obedience will always be rewarded with tenderness."

They both heard Tommy walking down the stairs. He had finally woken up, and he was sporting his morning erection. "What the fuck?!" He almost yelled. "How come I wasn't told about this?"

"Oh shut up and quit crying!" Tyler antagonized him.

"No! I'm serious! How come you didn't tell me the slut was coming over?"

Tyler looked down at Sandra. "Start sucking while I deal with this!"

Sandra released his cock from between her tits, dropped her head and slid his cock into her mouth.

"Damn you're good!" Tyler complimented her. His compliment only serving to drive her further in her desire to want to please him. He then turned his attention to his brother again. "First of all, this slut is mine now! So if you want to play with her at all, it will be by my good graces. They say possession is 9/10ths of the law. Well think of her as my possession now. Got it!?"

Tommy was going to put up a fight, but knew it would be useless. "Got it!"

"Good! Now, would you like to take care of that?" He said pointing to the bulge in his shorts.

"Of course!"

Tyler lifted Sandra's head with a fistful of her hair. "Let's move over to the couch." He stood and started moving to the couch as Sandra tried to stand. Tyler held her down. "No! You crawl bitch!" Sandra shuffled across the carpet on her knees as Tyler held a firm grip on her head. When he got to the couch he laid down and pulled her up between his legs. "Alright! Get back at it!" Sandra inhaled his cock again and began to suck and slurp on it with a renewed enthusiasm. Tyler moaned again with approval as he looked at his brother. "Damn this slut is good! I know she messed with you little brother. But you didn't have the balls to do what needed to be done. I did. Consider her the spoils of war. She's mine, and I don't plan on letting her get away. Now. . ." He pointed to upturned ass as she knelt on the bed sucking his cock, "have at it. It's all yours."

Tommy dropped his shorts and walked over to the couch. He ran his hand over her ass then smacked it hard. Sandra's body jumped as she squealed with her mouth stuffed full of cock. Her reaction made Tommy laugh. He smacked her again getting the same result. After several more smacks he decided to step up the abuse. He pulled Tyler's belt from his pants and doubled it over. He stood an arm's length from her ass and began to wail away on her upturned ass.

Tyler held her head firmly with both hands, not allowing her to pull off his cock. Sandra screamed as he kept his cock stuffed in her mouth. She tried to push off the couch and pull away from the assault on her ass. She was no match for Tyler's strength. She looked up at him, her mouth full, tears streaming down her cheeks, looking for mercy. Tyler looked down at her. "You shouldn't have messed with Tommy the way you did. I'm sure he'll be over it someday." He laughed. "I guess it won't be today."

Tommy continued his assault on her ass intending to inflict as much pain as possible. Tyler finally shouted. "Enough!" Getting Tommy's attention. "You scar her in anyway and I'll beat the shit out of you! I don't care if you are my brother and she fucked with you. Like I said, she's mine now! My bitch! My slut! My whore! Damage the goods and I'll damage you!"

Tommy dropped the belt and looked down at his work with satisfaction. Her ass was glowing red from the beating he'd just given her. Sandra was sobbing. Tommy's cock was rock hard from the excitement he'd experienced from the beating. He saddled up behind her ass and ran his hand between her legs. He pulled his hand away and held it up for Tyler to see. "This bitch is dripping!"

Tyler laughed. "I told you this slut craves this stuff!"

Tommy took his cock in hand and ran its head up and down her slit. Sandra groaned with the sensation. She had been driven with pain, now she was being driven with pleasure. He slipped the head of his cock into her pussy. Sandra moaned with pleasure and need. Tommy pushed his cock in balls deep. "Oh shit!" He moaned. "She is so tight!"

"I know! One of the benefits of the slut not having any kids. A nice tight pussy." Tyler laughed. He pulled her hair back so she could look up at him. "I see a lot of fucking in your future." He was going to use every opportunity to humiliate her and remind her of what she was, who she belonged to and what he had in store for her.

Tommy settled into a steady pounding of her pussy shaking her body with each thrust. He reached for both her wrists, twisted her arms behind her back and began to fuck her harder than she'd ever been fucked by anyone. "Oh yeah bitch! This is what I fantasized about all those months you teased me. This is just the first of lots of fucks you're going to get!" He smiled at Tyler. "What do you think Ty? Should we have a few friends over and have a fuckfest with her?"

Tyler smiled back. "I'm working on it!"

Sandra's eyes shot open hearing that. She tried to protest but was unable to raise her mouth off Tyler's cock to say anything.

"Let's see what her ass is like?" Tommy said as he grabbed both her wrists with his left hand to hold them behind her back. He took his cock in hand and pointed it at her rosebud. As he started pushing Sandra screamed on Tyler's cock. "Damn! Hold her Ty! Her ass is really tight." He grunted as he slowly shoved his cock into her ass. "DAMN SHE'S TIGHT!" He yelled.

Sandra continued to scream as it felt like her ass was being ripped apart. Tyler held her head firmly on his cock not allowing her to pull off. She began to grunt and pant for air as the pain intensified. When Tommy's cock was firmly inside her he stopped. Sandra felt like she was going to pass out from the pain. Then she had the sensation she was going to lose control of her bowels. She had never felt such pain before. How much more will they degrade and use her? She was about to find out.

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