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The Jordan Challenge Ch. 01: Pet’s Pets

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Ass

Ben could not remember being as satisfied with his life. He took a moment as he drove along Pacific Coast Highway to appreciate what a beautiful day it was. It was a day to play hookie. It was a day to lay in the sand, smell the ocean breeze, and watch the clouds, trying to identify the shapes before they mold into something new.

Things at the office have never been better. They were closing deals and frequently at the top of the sales board, and with that, the salary that comes with it. Henry has left them alone for a while now. Ben doubts it was possible to ever get on Henry’s bad side again, suspecting Henry would keep him on the nice list on the hopes for a second poker night even if it took years to wait out.

Stephanie has been perfect from day one and has yet to disappoint on any level, business or personal. She is his perfect symbiotic partner in all aspects of life. Ben loves and needs her completely and knows it. But that doesn’t mean that even King Midas gets bored of gold sometimes. If it is a beautiful day and things couldn’t be better, why is he no longer as happy with his success? His mind wandered and pondered as he drove, navigating and operating the vehicle almost as if on autopilot.

Looking up from his lap, “Big Daddy. Is everything ok?” Stephanie never needed to put this level of effort in a blowjob before. Especially on a morning drive. Big Daddy is not here right now, please leave a message. Without even having presence to her offerings, she pulled his semierect penis out of her mouth and looked up to him sad and confused. “You don’t seem to be enjo…”

Honestly, until that moment, he was so lost in his thoughts that he forgot she was even there, let alone sucking him off. Seeing the confused look made him guilty, he knew it was not her fault and she was obviously working hard and taking it personally. “Oh, my…. Pet, I’m so sorry. I just… I have a lot on my mind this morning for some reason and I’m not… present, I guess.”

“Is it something I’m doing wrong?” Her hand is still, well, let’s just call it ‘trying’, but there is just no response of excitement. She begins to take it personally.

“No, no… It’s not you, I promise. I’m having a great day. My head is just lost. I’m spoiled in every aspect and most especially with you. I don’t know what it is right now, but you are my whole world and I love you tremendously. I’m lost in thoughts, that’s all.”

Stephanie, never one to be unaware or one to be quiet about it, always with respect, begins to redress him and zips his fly before sitting back in her seat, tits remaining out and on display. She takes his right hand and holds it with both of hers before bringing it to her lips for a loving kiss. She closes her eyes, and you can tell it means something to her. She brings his hand down to her perfect breast and rests it there. “You know what I think?” He takes the time to ponder before shrugging his shoulders and silently shaking his head in response. “This lion needs a hunt.”

Curious to this statement, it was out of left field. As usual, he really didn’t know what the heck she meant, no matter how perfect her left breast felt. He squeezed. “Please explain.”

“You are bored. Your perfect life is too perfect.” Laughing at him being unaware to himself, she continued. “You, Big Daddy, are spoiled.” He looked over at her, both knowing she had a point and with a mask of warning her to remain respectful. She responds by forcing his hand into another squeeze. “Look. Let’s be real. You didn’t get here because you sat back and enjoyed yourself, you’re a fucking hunter (squueeeeze). You don’t thrive in success, you thrive hunting (squueeeeze) for it. You have it too easy right now and it’s been some time since you’ve had to work for it, work, me, sex, success… You need to hunt (squueeeeze).” On the last squeeze, she initiated the action but he took over and gave her a stronger grip than the others. She was talking herself into a very wet pussy. She reached down below her pant line with her right hand and glided a finger into the moistening fold, searching for, and finding her clitoris.

When Stephanie has a good idea, she knows it. When Stephanie has a good idea with slutty undertones, buckle up. Her face changed the second the idea entered her brain, and the eyes couldn’t hide it. Stephanie was entering slut mode and needed her medicine.

The idea hit her quickly. At the same time, she realized it needed to be done right. He is putty when she wanted him to be. Control is such a fun game when the two people trust each other and give into the moment.

In her best sing-song cutesy voice, “I know what you need, Big Daddy…. You need to train a new sub.” Her left hand reached back over to his newly well-dressed crotch and began to squeeze him back to life. “Just think about it, Big Daddy. What if you had a whole new filly to break in?” His eyes struck hers intently, then relaxed down and back to the road as she squeezed his now rapidly growing dick. Feeling his cock begin bursa escort to swell under her grasp encourages her that she is on the right track, literally.

Filly… Track… get it? You know, people pay good money for this level of clever writing… Ok, sorry, back to the roadhead story…

She is encouraged enough to continue. “What if we found another girl with huge tits, just like Tina? Those were so much fun to play with?!?” His eyebrows raise in interest, then shakes it off with a silent ‘nah’. She moves closer back into position, his hand increases his groping. A nipple is tugged. She unzips his pants to release his regained erection and her hand resumes pumping. “Ooh, there he is! Ok, no tits…” She ponders for a second and fixes the last statement. “Uhhm, howsabout, this time tits are not the focus” He shrugs to the compromise, moving his hand to the back of her head pulling down and close. “Oooohhh, this time, I train a sub slut. No hypnosis. I make her want it….. Would Big Daddy like that? I have my slut, who I can train to be your free-use slut and then we can train her together. We’ll get someone bitchy and make her a total whore for us.”

Her head drops back to envelop the fat cock as he ponders the moment. Man, her mouth was unmatched, her tongue was ridiculous, and she hit the bullseye lighting his fire. Stephanie had him and knew she would be tasting the salty treat soon. Substituting her mouth with her pumping fist, she looks up to him. “Redhead? Asian?? A nerd??? BLACK CHICK?!?!?” Her right hand is also now in full vigor. “What can I serve you, Big Daddy??” She squeezes his cock in her firm wet grasp, pulling up on the fat head making it purple. Turning her head to the side, flicking her tongue over the underside of the head before slurping on it with intensity. Her hand and tongue never stop.

“I mean. Damn… I mean, damn, I love tits, but whatevs… not big tits, something new, something different. I do like the make a slut idea, out of a normal anyone. Sure, someone who needs to be trained.” With his hand on her head he grabs and large handful of hair and holds her head down, shoving his cock in her throat, holding it. Pulling it back up, he is in full control of her actions. He moves her down to his balls, then back to the head for her to focus attention there for an extended moment. Removing his hand to grab on her blue jeaned ass, he gets back to his point. “No, no hotties and tits are optional, secondary… nobody who was a sex toy their whole life, let’s do a nerdy makeover. Demure, innocent… a nerd, yes, I like that, like a librarian…. Let’s slut a priss out.”

Going full speed, pumping her hand while her tongue masterfully works the head under closed lips and enough suction to lift a Buick, she feels his hand groping and squeezing her ass, so she moves to more of a kneeling position in the passenger seat. Desperate for his cum, she puts every ounce of herself into pleasing her mate. The lightbulb goes off in her head. ‘We already had an option. And he would like this one…,’she thought to herself.

Looking up from her cock using her eyes of kinky intent, he knew she had the perfect answer. He looked down for a moment to brush her hair from his view. Her tongue and saliva lapping away at his head, she spoke with her mouth full. “MMig Daddyummm…” Generating more saliva so that her hand can hold her mouth’s momentum nearing the end. She knew his landing gear was down and that we were on the final approach. “Mye Mmmnow Whommm…” Tongue flapping as she goes. “MMeady for this MmmMMmmmm…. Mormdommm!” diving down shoving the cock in her throat as she bucks and rides out her own orgasm.

Ben is truly a bit lost here. He is close to cuming, but he has no clue whatsoever what the fuck she just said. He can see she is very hot right now so it must have been a good idea whatever it was. Now in full orgasm, he needs to wait a few seconds, for her to ride that out… When she came back to the moment and realized she was on a solo journey, something was amiss. She looks up at him as though she just missed the train.

“What?” he says coyishly, holding back laughter. “I have no clue what the hell you just said.”

Pulling his cock out with a pop, she looks up at him like ‘really?’ “Jordan.” She returns to her work, just in more of a fluting style to ensure better communication.

“Who is Jordan?”

“Jordan. You know Beej’s Jordan… The babysitter, Jordan Lister from Tennessee. She must be old enough for debauchery now. She was a little nerd, great ass, decent tits, had a bit of an attitude… entitled. But I did catch her looking at you more than once, so I know she had thoughts, and well, I know everyone wants to fuck me, so that’s rarely an issue. I’d bet we can get her in the stable.”

Beej was the nickname for their now college-aged son, Benjamin Junior. Having two Ben’s in the house was hard, so they decided early on to refer to their son as ‘Beej’, being short for Ben Jr, bursa escort bayan or B.J. Ben considered the idea. He did remember his babysitter, Jordan, just not well or at first.

She did have a great ass, he remembered that much. She had to be older, like what, like mid-twenties? She couldn’t have been a young teen when she first started watching Beej and grew up before their eyes. She was never an object of attention, just someone who was around doing a job. She was young then, so it was a bend over here, or a bikini top there. Nothing against the rules. A man is a man, and things were noticed. She did have the perfect attitude to make getting her enough challenge to get him back in the mood.

Hearing the slurp on his cock’s head pulled him back to reality. Stephanie was moaning vibrations down his shaft in the form of yummy noises. He looked down and smiled. Back to looking at the road and his thoughts.

She was on the straight road to being a prissy librarian, house filled with cats. But a girl is also a girl and she had to be getting off from time to time, by flesh or battery. God only knows what dude qualified for that shit. He thought about little Jordan, all tied up. Arms straight out, legs spread, not a hair below her eyelashes. Stephanie is sitting on her face using her mouth, holding her nose with one hand, a wad of hair in the other directing. The only part of her face you see is a wildly lapping tongue, knowing she will not leave her mount until she has her signature squirt all in her pretty mouth. He walks up and feels her powerful thighs, glides his hand to her pussy, finding the nub, then inserting two fingers into her very wet folds. “Is she doing a good job, or are more lessons needed?”

Realizing his IRL hand is actually doing the same to his Pet on the road, he is overwhelmed, and his orgasm explodes into Stephanie’s dirty mouth in a huge milky load. She sucked and slurped and swallowed and cleaned his cock soft… Except it wasn’t going soft. Ben continues holding Stephanie’s head right where it was adding a hip sway to be sure he was driving it deep. “Keep your mouth open slut… No teeth… I want this next one in your throat.”

Stephanie repositions herself on all fours, getting more comfortable. Moving his hand back down to give her ass a good hard squeeze. “Pull your pants down!” She reaches down to unfasten the buttons, pulls them to her hips where they find some resistance. Pulling one side down to her knees, his hand moves back to grab her hair, guiding her head and holding it until she needs a breath, causing her a large drool. “OOOhhh. You like this idea, don’t you dirty slut?” With the head of his cock deep in her throat, Stephanie manages to create a somewhat agreeable noise. He pulls her panties over to the side and finds her pussy.

“Is this toy for me, or is this toy for you, dirty slut??” Pulling her head up by the hair to face him, he waits for his answer.

“A pet for me is two pets for you, Master…” He kisses her deeply.

“Good answer. See that trucker there… I’m going to pull up next to this dude and set the pace. I want him to see you fingering your pretty pussy. Then I’m going to cum into your throat again. Show him what a good girl you are. Put on a proper show and you will get your toy.”

Her knees widened and she looked over to the trucker as they approached his side. Ben honked while Stephanie played with her tits to ensure his attention was not only gotten but kept. A new friend was made. Once sure he was looking, she opened her mouth wide to show it was empty, and lifted a single finger to communicate the ‘hold please’ action.

Turning back to Ben and lifting her ass high, she pulls her cheeks apart for a better view. “I am always a good girl, Big Daddy. Now please cum for your little slut so I can get my new pet.”

Less than 10 seconds later her mouth was full, her end of the deal had been paid. She turned back to the trucker, opened her mouth to show whatever was not yet ingested from the pool of creamy white liquid, pulled her other tit out for him. The truck swerved. She wagged her finger like ‘no, no, no’, pinched and pulled out each of her nipples, tilted her head back and swallowed the entirety of it. Completing the move, she showed her new friend how her mouth was again empty, ta-da! The trucker honked his big horn in thanks, and they sped off.

“Tell me your plan… A contract will be needed.”

“Hi Jordan? This is Stephanie… Yes, hi. I know, too long. Something came up and I thought of you. I have a job opportunity and was trying to explain to Ben what I thought of as a perfect candidate, and every time I would describe this role, I kept wanting to say, ‘like Jordan…’. So, really, you are the only candidate on my short list. I was wondering if you have a few minutes to talk. I know you always felt like you could do more, and I wanted to offer it to you first before I opened the applications to the public. Are you working escort bayan now? Oh, you are still at the library, wow, is that fulfilling for you, or was I right in thinking that you wanted just a little more?”

Jordan was a simple read. Born as the only child to an elderly Tennessee couple, she was a natural spoiled antisocial overachiever, always expecting to sit at the CEO’s desk without needing to stop at the mailroom first. As hot as she was, she was very much a nerd as well as a bit of a brat. She was raised on a farm birthing cows, giving her an almost sugar-coated innocence. Her accent is heavy and her laugh is intolerable.

If it was easy, anyone would do it. The fun is in the journey.

Jordan is happy to hear from her old boss. There was comfort there. Somewhere between a nanny and an au pair, she knew these people and they trusted each other. There was comfort at the library, but even librarians get tired of books. At one point, no matter how great the story was, it was always someone else’s experience. The more she was lost in a book, the more of her life and herself was lost to it. She was looking for more. If not, she was on the road to being a spinster, eventually found eaten by the cats she fed for so long.

Sorry, that was dark. Some of you did laugh at that though, just sayin.

“No, Stephanie. I mean, I’m working now, but I think I can do better. Is the job like your job with Ben?”

Loving how she immediately goes for the best possible job out there, hers, Steph laughed to herself. This was going to be more fun than she thought. “Yes, well, similar. I work for Ben, I would need you to work just the same for me. This would be as my assistant, helping me, helping Ben. I will still be working with Ben, we are a very successful team. I will need someone to help me in the literal exact same capacity. I remember how efficient you were and how we trusted you, and if you were looking for something that would be a little out of the box, very well paid, we travel together, and unlike anything you’ve ever known. But like you used to be with us, you are welcome to live here as needed, if you like. We’re going to be together a lot and your freedom is not being infringed here. Live your life, please. Just know, if you decide to love this job, want to fully commit, save time and money on driving and rent, it is part of the job and we’re going to be together virtually all the time. Have you been to Paris? I have no reason to go right now but I told Ben I had a trip planned, so we can get away while he pays for it! Will we work, of course. But after the massages.”

Fish, meet bait. The method Stephanie chose here was a simple premise but will not be easy to pull off. Dangle, hold at a distance, only those who are worthy can get in, are you sure you’re worthy and how bad do you want this? The exclusivity is the ‘carrot’. The will to want to be the one selected before she needs to compete with others to get in is the ‘stick’. The real trick is in telling her she is the horse being led by the carrot, and then making her want it… knowingly.

People typically take time to come to these decisions. It was Stephanie’s goal to make her want this on her own without knowing she was ever offered a choice. She could manipulate Jordan. But even the Queen gets tired of playing with her food. She wants to be the queen and watch the food offer itself up for her to eat.

My analogies are off here, but I believe you, my readers, are smart enough to follow my point. Love you guys.

“The problem is I need someone who I can trust. It could be an easy road to replace me at the office, if things fit. So, it’s not like I cannot say this could be the fastest road to replace me with Ben. Same time, no way is that being offered here. You would need to prove yourself in a big way first. Trust me, the pay for this is generous and the benefits are unmatched. I’ve been wanting to spend less time working, but I need to have someone who knows me, is willing to literally eat, sleep, and live by my side, know how I think, and do whatever is required of me and for me, and with that eventually, be Ben’s number two, being there for him whenever he needs it.”

Jordan loves being flattered. She put the hook in her own mouth, pulled it snug, tugged the line two times to cue being reeled in. She is honored to be given the job, more than she should before hearing what most would consider a job description. “Uhm… Okay. I mean, sure. I can do that. I liked working for you guys. I remember Ben, the house was beautiful. I always got paid on time and you treated me like family. How is Beej, is he around?”

“Away at school, Senior year just started. He will be back home for the holidays. It isn’t housekeeping. So, nothing like that. It is more being my assistant. I would love to go into what would be a typical day to day, but honestly every day is different, and the in-office work can be taught to you as we go. But I’ll be working for Ben for the next few months at least. We would have time to turn the office job over to you… You’d have to earn that one, but I know you have the tools to pull it off. For now, this is just about being my girl. Follow me everywhere, every day. Help me keep appointments, take calls, oversee the calendar, travel with me, take care of our needs. “

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