The Jake Chronicles Ch 03

Letter from the Author: This story is about a very dominating young man who takes advantage of older vulnerable women. There is humiliation and degradation in it. It is just fiction. It is not about hating women or anything of the like. It turns me on to write and read about this, and I hope you too. If this is not your cup of tea, please find another story. If it is, I hope you enjoy. Feedback is always welcome, good and bad, as long as it is constructive.

Goamz86

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Over the next few months Jake enjoyed his two latest conquests on a regular basis. Trish was passive, and available at his request, as she continued to battle her demons. Debbie however, was getting more and more aggressive. She would constantly approach Jake at work and proposition him. He was enjoying the attention, but she was beginning to get on his nerves. He had awoken a sexual monster. No matter how much he ignored her, or humiliated her when they were together, she just continued to beg for more. She was getting more and more risky with her behavior, and he was beginning to fear he would lose his job. He needed to get rid of her and he needed to do it soon. He formulated a plan to get Debbie fired, thus eliminating one headache in his life. Jake knew Trish would not fire him and his devious mind always found a way to get what he wanted and it usually was accomplished in a sexual way.

One day Debbie approached him as he went about his business. She snuck up behind him and whispered in his ear, "My ass is craving you big fat cock."

Jake heard her and decided this was the day his plan would be implemented. He turned to her and told her, "You can only have it if I can take your ass on your boss' desk."

Debbie froze. She had not expected anything like that, but it was not much riskier than many of the other times they had done it at work. She got a devilish look in her eye and told him she would e-mail him later and tell him when to meet her in Trish's office.

Debbie talked Trish into taking a long lunch to do some shopping and cheer her up a bit. Then she e-mailed Jake and told him to meet her in the office at 12:15. Jake read the message and when lunchtime rolled around he waited until he saw Trish leave, then about ten minutes later he called Trish and told her he wanted to meet her in her office at 12:45.

"I have a surprise for you." He told her. Then he proceeded to go to Trish's office to set his plan into motion.

Debbie was waiting in the office as he expected. When he entered, he found her bent over Trish's desk. She was spreading her ass wide with her hands and it was glistening from the lube she had rubbed all over it. When she heard him come in, she looked over her shoulder and said, "Come split this ass with your lovely cock."

Jake was a ready for action. He pulled out his already stiff dick and drove it all the way to his balls. Debbie moaned appreciatively. He then began to pound her ass relentlessly for the next 15 minutes. Debbie moaned and groaned and begged for more the whole time.

"Oh my, yes, fuck me in the ass like the dirty slut I am. Fill my ass with your cum baby. Tell me how bad I am, I need to hear it."

Jake talked to her like she wanted. "You filthy tramp, you love it in the ass don't you? You don't care that your boss could come in here and catch you fucking her lover do you?"

"No!" she answered, "Fuck my ass harder."

Jake had her going good now. He was expecting Trish any minute and he was going to be able to get rid of Debbie and her clinging ways for good.

"Tell me I'm better than her." Debbie begged. "Tell me she can't make you feel like I do."

Jake just fucked her in silence.

"Tell me, please." Debbie begged. "Tell me you don't need that big titted cow anymore. Let me take care of all your needs baby. Get rid of that bitch. I can do anything she can do."

Debbie's body tightened and she came for the first time. Jake just rode her ass the whole time.

Debbie was not finished insulting her boss though. She wanted Jake for herself and she continued to talk, "Would that cow do this for you? Would she do you in her boss' office?"

Jake just stayed silent as he saw Trish walk in the door. Debbie was talking and enjoying herself too much to notice.

Jake looked at Trish and smiled as he talked to Debbie, "Who's a big titted cow?" he asked.

"Trish is." Debbie told him. "She's a whore, and she dresses like a tramp. You deserve more. I'm better than her. Oh my, fuck me harder.

Jake motioned for Trish to remain quiet. As always, she obeyed, even though she wanted to rip Debbie's head off in a jealous rage. Jake treated her poorly, but Trish still felt the green monster of jealousy raging inside her. Jake grabbed Debbie's hips and drove his cock deep inside and emptied his balls into her. He grunted and groaned as his sensation enveloped him.

"Oh yea, cum in my ass baby. I love that." Debbie told him. Jake finished and pulled his cock from her rear passage. Debbie spun around as she said, "Does she make you feel that good baby?"

Before she could realize what was going on, Trish answered her question, "Yes as a matter of fact this big titted cow does make him feel that good."

Debbie was stunned. She wasn't expecting company. She instantly began apologizing to Trish.

Trish just raised her hand to her and said, "Get out! I will send your belongings and last check to your house later."

Again Debbie tried to apologize. Trish just pointed at the door. Debbie pulled her skirt down and left the room as Jake's cum drained from her ass. When she had left the room, Trish began to scold Jake.

"How could you? With my secretary? You are unbelievable."

Jake just stood there as she continued to scold him.

"This is the surprise you had for me?" she said with disgust.

Jake just stared at her and said nothing. Trish walked passed him and headed for her chair. Jake quickly moved around the desk and positioned himself behind her. As she tried to sit down he grabbed both of her wrists from behind and pushed her up against the wall so her hands were above her head and sandwiched between the wall and his hands.

"What the hell are you doing." She spat at him.

"Didn't you like the show?" he asked as he pressed his half naked body against her back. His cock was still hard and it pressed against her ass.

"NO!" she hissed.

"Liar, I know you enjoyed watching me fuck your secretary." He returned.

"I'll bet you pussy is all wet right now." He spoke into her ear as his hand slid down her side and found its way under her skirt.

As much as Trish wanted to deny his allegations, her dripping pussy gave proof of her arousal. Jake slid a finger between her pussy lips and said, "I knew it. You filthy whore. You got hot from watching didn't you?" he asked as he continued to manipulate her pussy with his fingers.

Trish was hotter than a pistol at this point. Jake's hand in her cunt and the feel of his cock pressing into her ass was more than she could take. She could not resist any more. She laid her head back against his shoulder and answered, "Yes." in a breathy voice. "I loved watching you fuck her in the ass. It turned me on. Please, fuck me like you just did her. Take me in the ass right here up against the wall. Shove that big hard cock deep inside my fat ass." She begged.

Jake got a big smirk on his face and knew she would do anything now. He pulled his finger from her pussy and lifted her skirt over her large round ass. Then with the juices from her pussy covering his fingers he slid three of them up her dark rear entrance

Trish moaned loudly as she pressed her ass out against her intruder. Jake slid his other hand down to squeeze one of her large tits. Trish again moaned approvingly. He slid his fingers in and out of her ass and mauled her tit at the same time.

"You want it in the ass?" he asked. "Well you will have to clean my cock before you can have it in there."

Trish didn't hesitate. She quickly spun around and dropped to her knees and sucked in his rigid shaft. As always, Jake grabbed two handfuls of hair and began to fuck her face with great pleasure. Trish had no shame. She enthusiastically devoured his cock. She deep throated it several times and stroked it with her hand as she sucked it too. Jake pulled her off his cock and stood her up. He unbuttoned her top and raised her bra up over her tits so they dangled below it. He didn't remove any of her clothes, just exposed all of her womanly features.

Stepping back, he began to humiliate her some more. "Look at you, you are a filthy tramp. Standing in your office half dressed just begging to be fucked in the ass, and you just sucked the taste of your friend's ass from my cock."

Trish had no reply. She couldn't believe it herself, she should be putting a stop to this right now, but she couldn't. No matter how badly he treated her, it just turned her on more. Her body was on fire, and all she could think of was how much she wanted him to fuck her in the ass.

Jake ordered her against the wall again. She did as she was told. She placed her hands against the wall and pushed her round ass out for him. Jake grabbed her hips and mounted her roughly. He instantly began to pound her ass like a man possessed.

Trish just took it and enjoyed it the whole time. Her tits slapped against her body with each thrust as they dangled below her pushed up bra. She moaned and squealed with delight. Not long after he started, Jake leaned against her back, reached around her body and started to pinch her nipples roughly as he endlessly drove his cock deep into her bowels.

The nipple stimulation was all Trish needed. She bit her lip to keep from screaming as the wave of orgasm swept through her. Jake assaulted her ass for a short time more before he felt his orgasm coming. He pulled out and ordered her to her knees. Then he stroked his cock to orgasm and pelted her open mouth, face and tits with his spunk.

Trish again cleaned his cock and he left with a smartass comment. Trish just sat there as she always did after sex with Jake, humiliated, but thoroughly satisfied.

That afternoon, Jake left work and found Debbie at his car. She told him she was happy that Trish knew about them, now they wouldn't have to hide. When Jake told her it was over, she was crushed. As hard as she tried to, she was not able to convince Jake to take her back. Jake never hooked up with her again.

A couple of months later, Jake was beginning to get bored with Trish. He needed some new meat. He was at his friend Josh's house one day. They had just come home from playing basketball at the park. They walked in and Josh's mom was doing some house hold chores. She turned to greet them when she noticed Jake. She had seen him before, but standing there with a layer of sweat and now shirt, she felt a small twinge in her groin. Jake noticed the look and as always, took advantage. He approached her and extended his hand to greet her.

"Hello Mrs. Turner, always nice to see you." He said.

Leigh Turner extended her hand and greeted him back, "How are you Jake?"

Leigh Turner was an easy target. She was forty-two and not the prettiest woman Jake had met. She knew that because her husband of twenty years made her aware of it the whole time they were married. He pointed out every good looking woman he saw and gawked at them all the whole time they had been married. It had crushed any confidence she had in herself when he decided his young hot secretary would make a better wife then Leigh. The extra pounds she had gained in her maturing years filled out her ass, tits and thighs, but her stomach had stayed relatively flat, no rolls or pooch to it. Since the divorce, she had hardly dated at all and she was ripe for the pickin'.

Jake felt a slight tremble in her hand, confirming his allegations that he was having an affect on her. He gently shook her hand and cleverly winked at her. Her knees got a bit soft and she tried not to blush like a schoolgirl. She let go of his hand and quickly turned to hide her face. Once she had regained her composure, she turned and asked the boys what they were up to. Josh explained he had come home to shower so they could go catch a movie with some other friends.

The boys went to Josh's room and Josh headed for the shower. He was in the master bath, when Jake decided he needed to pee. He went to the bathroom in the hall, but his effort to close the door failed and it stood partially open. He was standing holding his semi hard dick waiting to pee when Leigh opened the door unexpectedly.

She was shocked to see Jake standing there half naked, and immediately apologized, "I'm so sorry, the door was open, I didn't know anyone was in here."

She began to leave when her eyes caught Jakes cock. She was frozen for a second. It was big, and looking at him hold it in his hand made her a bit flustered. Jake noticed her stare and played it off.

"That's ok; I didn't close the door all the way. Leigh snapped back to reality and left quickly.

Jake finished his duty and went to find her. He needed to strike while the iron was hot, before she could come to her senses. She was in the dining room leaning over as she dusted the wide oak table. Her ass jutted out and the small sweat shorts she was wearing rose up to expose some of her cheeks. Jake moved quietly behind her and pressed his body against hers and leaned over to whisper in her ear.

"Did you like the sight of my cock in the bathroom?" he asked

June was startled, but didn't stand up. She just lifted her upper body off the table. She turned her head slightly and surprisingly to Jake, answered him in a naughty voice, "Yes, it is quite large."

Jake was stunned, he was expecting a confrontation. However, it didn't take him long to react right back. He reached around her and grabbed hold of her dangling tits. She had not been expecting any visitors, so she was only wearing a long t-shirt and no bra. Jake found her nipples and tweaked them a bit as he ground his stiffening cock between her ass cheeks.

Leigh arched her back and enjoyed the sensations. She moaned a bit and turned to talk again, "if you are going to fuck me with that thing, you better hurry. My son won't be in the shower all day."

Jake needed no further encouragement. He dropped his shorts and ripped her down to. She was not wearing any panties. He instantly pushed his entire cock up her moist love canal. Leigh moaned and pushed her ass back against his thrust. Jake began to fuck her fast and deep, pumping her pussy like a jackhammer. Neither one of them spoke. It was only about two minutes before Jake was grunting and depositing his cum inside her hot hole. He pumped all he had inside her and when he was done, he pulled his shorts up.

Leigh stood, and then bent over to pull her shorts up as the seed of her son's friend began to escape from her. She pulled her shirt down over her shorts and walked by Jake saying, "You are going to have to last a bit longer if you plan to satisfy a real woman, stud." Then she walked away.

Jake was astonished. He never expected her to be so willing and confident. He was totally turned on. He had to have her again and soon. He almost chased her to her room. As he entered her room, he heard the shower stop. Lowering his voice, he asked Leigh when he could see her again.

"Easy cowboy, don't get too ahead of yourself, who said we would see each other again?" She quipped.

Jake was flabbergasted. No woman, let alone an old broad like her had ever told him that. He had to prove that he was not a quick cumming little teenager. Josh opened the door and looked at them oddly, wondering what Jake was doing in his mom's room. He blew it off and he and Jake went to his room.

Leigh was giddy. She had never taken that approach with a man. She liked the fact that Jake was asking to see her again and she was playing hard to get. The only problem was that she was still turned on. She had not gotten to orgasm, and the little game playing after, was making her hot. She wanted to go in and attack Jake right now. However, she obviously couldn't do that. Her nipples were rock hard, and every move caused her t-shirt to rub on them, stimulating them more. She reached down and touched her pussy through her shorts. It was so aroused, she could feel the heat. She gently rubbed it and enjoyed the stimulus. Her knees got weak. She pushed her shorts to one side and slid a couple fingers inside her moist hole. Slowly she slid them in and out as she massaged her heavy breasts with her other hand. She pinched her own nipples and let out a whimper.

"Are you thinking about my cock?" Jake whispered into her ear.

Leigh had forgotten to close the door. Jake excused himself from Josh's room, saying he needed to go to the restroom. He was delighted to see Leigh in this state, and took advantage.

Leigh let out a small yelp of surprise. Then, realizing it was too late to have any dignity she looked him in the eye and answered, "Oh yes." Then just as quickly she asked where Josh was.

"He's getting dressed." He answered. "You want my cock again don't you Mrs. Turner?"

Leigh answered without hesitation, "Yes, but Josh is right in the next room. Get out of here."

Jake grabbed one of her hands and placed it over the raging hard-on in his shorts. Leigh squeezed invitingly, massaging it slowly for a moment.

"You want it in your naughty pussy don't you?" he teased.

"Yes." She replied.

Jake had her now. He reached out and pinched both of her nipples through her t-shirt. "Josh is going to that movie with our friends; I will be back in a half hour. Be ready for me." He told her. Then just as quickly as he had entered, he left. Jake told Josh he was not feeling good, and said he was going to skip the movie and go home.

Leigh heard him leave and she lied down on her bed. "What am I doing?" she thought to herself. She realized that all the power she just had over him 15 minutes ago was gone. How was she going to get it back? She decided she would tell Jake "no" when he returned. After Josh left, Leigh lay on her bed formulating her speech to Jake. When the door bell rang, she went to answer it, however, Josh had not locked the door, and Jake let himself in. He met her just outside her room and she was caught by surprise. Before she could say a word, Jake spun her around and guided her to her bed.

Leigh feebly tried to protest. She sat on the edge of the bed and he ordered her to get undressed. June refused. Jake unzipped and removed his pants and then his shirt. Grabbing his fully erect cock, he walked up to her, stopping with his cock inches from her face.

"You know you want this." He quipped. "You want me to fuck your nasty cunt senseless with it don't you?"

Leigh tried to resist, but his demeanor and his naughty words were getting to her.

"You want to take it in you mouth right now and suck it dry don't you?" He asked.

She did want to take it and devour it, but she didn't.

"Come on Mrs. Turner, you know you want it. Open your mouth. Let me slide my cock down your throat." He teased her some more. Slowly he began to stroke it in front of her face. "Open your mouth, take it in you know you want it. Suck my cock Mrs. Turner."

Leigh could resist no more. She opened her mouth and reached out to grab his big throbbing cock. She slid it deep into her mouth. The feeling was ultimately arousing. Her whole body tingled at the thought of her devouring this young hard cock. She began to slide it in and out quickly. Jake grabbed a handful of hair and began to encourage her, "Yea, suck my cock you nasty old slut. Take it all."

Leigh was not inexperience. She had sucked lots of cock and fucked lots too. She however had never had someone talk to her or treat her like this. She did find it a bit arousing. She took his cock deeper and deeper until it was sliding down her throat. Jake pushed harder and got more aggressive. All that made it more exciting. Soon he pulled it from her mouth and ordered her to turn around and bend over the bed. Leigh stood and disrobed, then turned around and did as instructed. Like before in the dining room, Jake instantly buried his cock deep inside her and began to fuck her silly. He grabbed hold of her hips and pounded her pussy for what seamed like forever, Leigh screamed obscenities and begged him to continue.