Training a Housewife Ch. 03

Trent looked down at his prize. The soft white skin of Rebecca's bubble butt marked red with his hand prints felt incredible against his swollen cock as he grinded back and forth against it. After 5 years of leering and fantasizing, he finally had the busty milf right where he wanted her. Bent over, her wet pussy begging to be ravished over and over again. He gripped her hips with his strong hands, pulling her back and forth under his rock hard member. He gave her ass a rough slap, deepening it's shade of red as Rebeca let out a sharp moan.

The ex-police officer enjoyed how easy it had been to bring Rebecca to this point. Obviously the financial insecurity of the Jackson's; in addition to the life line he could provide, was a powerful motivator, but Rebecca's submissiveness to his devilish desires reflected something in her that only Trent could see and understand. Something about herself she may not be able to admit. Yet.

After 30 years on the force, Trent could read people and knew instinctively how far he could push them. And Rebecca, even if she wouldn't admit it to him or even herself, was a masochist. And Trent was well equipped to satisfy that side of her.

He began to press the tip of his cock into her moist pussy lips. Rebecca moaned from the sensation but resisted giving herself completely to him. "Please, Trent. Not that, we can't."

Trent in response grabbed her ponytail, yanking it back. "I thought I told you to call me sir!" He spat at her. 
"S-Sorry sir. Please..sir.. I can't keep going." Rebecca pleaded with him.

Trent had a sly grin on his face. He let go of her pony tail and started running his hands up and down over the toned housewife supple ass, admiring it. 
"Yeah? You know, from where I'm standing I think you're full of shit." He said as he ran his fingers through and into her pussy. He leaned forward, and wiped Rebecca's juices across her face, proving his point. "I think you're just afraid you're going to like it." He said, whispering into her ear.

Rebecca had a disgusted scowl on her face. "How could someone enjoy something as violent and perverse as this?" She said to herself. But as she asked herself that question, while Trent began again to grind and slowly press himself into her, she felt her hips respond. Moving with his, against her wishes.

Trent could see her responding to his touch and smiled. "You're my slut now. You got that."

He grabbed the leash still dangling from her neck and wrapped it around his knuckles, shortening it's lead. "By the time the 3 months is up you'll be begging me for it." He said as he started pushing with force his entire length into Rebecca's sensitive cunt. Rebecca's eyes went wide at the intrusion and couldn't help the loud gasp pass her lips. Trent pulled on the leash, forcing Rebecca's head back. He started thrusting into her pussy with long forceful strokes, his cock reaching further into her than she thought possible.

The pleasure was unlike anything Rebecca had ever experienced. She could feel the walls of her vagina stretching to accommodate Trent's size as his member pressed against her womb with each deep push. And while she struggled to breath, every time he slammed into her she couldn't suppress the sharp moans leaving her lips


Trent placed his free hand on her lower back, spreading out his fingers so that his thumb rested on her gaping asshole. He used his strength to guide Rebecca's hips back and forth, matching the rhythm of his own thrusting. Ripples were sent across her ass cheeks as Trent mercilessly pounded Mrs. Jacksons pussy. Her big tits swinging in motion.

Rebecca could feel another orgasm building up inside her without her consent. Without realizing it, she began to move her hips, matching Trent's motion without his own hand forcing her. Trent wailed his hand down on the milfs impressive ass. Rebecca's moans were mixed with cries of pain as the brute had his way with her body.

"Tell me you want to cum, cocksleave." Trent growled, bringing his hand down hard once again against the housewives bare asscheek. Rebecca couldn't think straight, she was in way over her head as each thrust from the large man's cock inside of her seemed to scramble her brains further.

"I-I want. To.. Cum." She managed to get out. The sound of her ass smacking against Trent's pelvis nearly drowning out her own voice. 


Trent pulled the leash back signalling his dissatisfaction with her answer. His thumb pushing into her asshole.

Through the pleasure Rebecca tried again. "Please. Sir. I. I. Want to. Cu-AHH."

Rebecca didn't have time to finish her sentence before Trent lifted her lower back off the floor. Still inside her, he gripped her by her waist and wrapped her legs around his own. Rebecca's arms remained on the floor as Trent held her in a wheelbarrow position. Trent steadied himself before Rebecca could and he began thrusting faster and harder than before. Rebecca screamed in pleasure.

"Cum for me slut!" Trent yelled, he could feel her pussy gripping his cock. He maneuvered one hand underneath her belly; easily supporting her frame with his strength, and his skilled fingers found her raw clit, still sensitive from her previous orgasm. He started playing with it while continuing to impale her cunt over and over again. Rebecca's whole body jerked violently from the profusion of pleasure but was no match for Trent strength.

"No! Pl-Please Sir It's too much!!" Rebecca begged, she felt like her pussy was on fire as her body reacted wildly. Her head was spinning and she could feel herself losing consciousness again. Her mind was breaking as Trent had his way with her. And, putting up no resistance this time, once again her orgasm took control. It erupted in her loins and spread through her whole body. Trent could feel her climax as the walls of her cunt convulsed, gripping him tighter. Rebecca body finally went limp from satisfaction as Trent pulled himself out of her and dropped her to the floor.

She laid there. Dazed and fatigued, her leg still shaking. She could have passed out right then and there; her naked body covered in sweat and a mixture of Trent's and her own bodily fluids, but Trent had other plans. He scooped up his milf and threw her over his shoulders like a rag-doll and carried her to his bedroom like a warrior claiming his bounty.

He dropped her onto his bed. If Rebecca's perception hadn't been muddled by the multiple shattering orgasms she may have noticed the rope and various toys indicating her torturer was not yet through with her. But instead, she put up no resistance to her new master as he forced her into his desired position. It wasn't until the ball gag was forced into her mouth that reality came crashing back and her tired eyes grew wide once again. She looked into her captors eyes, searching for remorse but found none.

Her muffled protests didn't bother Trent as he pushed her legs back towards her head so that her knees were shoved up against her ears. He then grabbed each of her arms and interlocked them with her corresponding legs, tying them together. Finally, he secured both to the backboard behind her. He leaned back, admiring his work. With her arms and legs up above her head, her cunt and asshole spread them selves involuntarily for his gaze.

Rebecca's breathing picked up as panic set in once again while Trent watched her fat tits heave dramatically. He grabbed two small metal clamps from behind him, each one with a thin chain leading to a small weight. He dangled them in front of Rebecca's fearful eyes with a mischievous grin on her face.

He grabbed her right nipple, twisting it forward while Rebecca let out an obstructed squeal. He held her massive breast in place as he clasped the metal toy to the nipple. It's teeth digging into her sensitive udder causing her to howl in pain. He proceeded the same way with her other breast. Rebecca's face was beet red from the discomfort and attempts to scream.

"It's time I make you mine my little whore" Trent teased as he lightly tugged on the dangling weights, stretching her fat cannons out in exasperated discomfort. "Are you ready to take my seed, slut?

Rebecca glared at Trent with a new fear unlocked. She shook her head, her eyes pleading with this monster who could care less.

He grabbed another toy from beside him, a small pink egg with a wire string leading to what looked like a remote. He turned it on and Rebecca could hear the motor inside it vibrating. Trent rubbed it over the milfs wet and severely sensitive pussy. Rebecca jerked as if being electrocuted shaking her head and pleading with Trent best she could with the ball gag disrupting her ability. Finally, the small toy settled on her asshole as Rebecca felt Trent's finger pressure it inside of her. He pushed it, deep, deeper into her tight hole as his long finger guided it in. She squirmed in even greater discomfort as Trent pulled out his finger and increased the motors speed.

"I'll make a deal with you," Trent said, gripping her chin between his hands. "If you can manage not to cum in the next 60 seconds, I won't cream pie you. How does that sound?"

Rebecca tried to say something but her struggles just made Trent chuckle to himself. "I'll take that as a yes, princess."

The egg felt strange as it vibrated between the walls of her virgin asshole causing Rebecca's whole body to wriggle in response. Trent mounted his slut again, angling his large stiff cock into Rebecca's spread pussy lips. He let out a moan of his own as he slowly pushed through her. Rebecca felt like she was going to tear open as his cock pressed deeper into the canal of her abdomen. Her eyes rolled over from the pain.

Trent started slowly thrusting. He couldn't believe how tight she was, how her insides hugged him. Finally, he grabbed the toy on the bed, a large Hitachi wand. Rebecca, her eyes still closed, felt the head of the wand press against her sore clit. Before she could react the vibration sent her body into convulsions.

Trent laughed as he watched her body flail helplessly. Her tits, and the weights attached to them, bounced around causing even more pain for the tied up milf. Rebecca couldn't control herself. She started crying as drool dripped down her lips. Trent kept up the assault.

"40 seconds left!" He chirped as he increased the speed of the wand.

Rebecca was helpless and couldn't stop the mounting orgasm willing itself on to her. Her whole body was tired and every muscle ached as she tensed up once again. She couldn't hold on any longer. She flung her chest and pelvis forward, her fat tits sticking out. She could feel her legs shaking while fighting their restraints.

"Ooooh too bad baby girl. 10 more seconds and you woulda won," Trent said condescendingly. "Now it's time for my prize."

Trent tossed aside the wand and used both hands grin Rebecca's ass cheeks. He started pounding her more forcefully. "God, your slutty pussy feels so good." He said as he closed his eyes, enjoying his new toy.

Rebecca was nearly unconscious but could feel his cock twitching inside her. She once again pleaded desperately with Trent to stop but he had since blocked out the milfs complaints. Finally, after one more deep thrust, she felt his thick, powerful load shoot into her. She could feel rope after rope paint the walls of her beat up pussy as Trent let out a satisfied moan. He pulled out of her and his cum slowly dripped out of her sloppy cunt.

Trent took a deep breath, finally satisfied. Rebecca's body still slowly twitched as she laid their in defeat.