Mastering Jacqueline

by Jordan Church

  Jackie sat and waited. It was torture. The boredom. The dreadful expectation. Her layers of uncertainty. Crazy eyes almost constantly staring at her.

  What really haunted Jackie were her own thoughts and suspicions. Had Jones sent her here to give Robert sexual pleasure as a random act of degradation, or because in some twisted thread of honor he really did want to reward Robert for sending Jackie into his clutches, or was it much more plotted out?

  Jones could have had her commit to a sexual interlude with anyone. He seemed to have many followers. He even could have heightened the humiliation by having it be someone disgusting, unattractive, or rude. Like that security guard Wilrey. If he’d had her get with Wilrey Jones even could have watched. Jackie could not help but wonder if Jones would have enjoyed watching her be fucked. So, why had he sent her away from him, to be defiled by a sweet intelligent gentleman, off site, where he could not watch? Was it because he could have his choice of many women and would enjoy watching them be fucked more than watching her? Jackie was oddly tempted to feel rejection, to feel a little hurt. She reassured herself that Jones had so many women at his disposal that simply viewing sex was probably a pleasure that would pale to insignificance for “King Jones”.

  Jackie flicked her eyes toward Crazy Eyes. The receptionist was staring at her as if she could read Jackie’s mind. What a horrible thought. Even a strange girl she disliked knowing those thoughts would be terribly embarrassing.

  Crazy Eye’s staring also made Jackie glad she wore a thick dark wool business jacket buttoned over her blouse. Those damn big heavy nipple rings were all too obvious in most clothing. She wondered how she was ever going to get them off. It would be mortifyingly embarrassing to seek help. As soon as she defeated Jones she’d have to take care of them with or without help. She was worried they were doing permanent harm to her tender nipples and the stretched skin of her breasts.

  Why had Jones sent her to seduce and pleasure Robert? Was it because he was actually grateful Robert sent the beautiful Jacqueline Thorpe served up to him on a silver platter? Jackie suspected gratitude was a rare emotion in Jones if he was even capable of feeling it. An image of the two slaves giving Jones oral pleasure and the satisfaction on his face flashed to mind. Appreciation, yes, gratitude, no. He expected others to be grateful to him. When things worked out well for him he seemed to think it was his “kingly” right.

  Jackie concluded he had set forth this mission purposely in order to foul the waters of her future workplace and muddy her emotional associations with her future ambitions. Once she did this, how could she look forward to a partnership in Arlington’s practice? Every time she saw him -- which would be most days -- she would think of what they did together today -- whatever those actions turned out to be -- and of Jones’ degrading manipulation of her. Jones had assigned this task in order to ruin her future aspirations, her imminent dream come true. Nothing else could accomplish that task as well as this. Evil and brilliant. Jackie felt respect and admiration for Jones’ cleverness blend weirdly with her resigned upset.

  She waited for over an hour. A few times she heard that stapler used, the one Crazy eyes suspected of being vampiric. Once she looked over when it was used and was surprised to see Crazy Eyes staring at her and not paying any attention to what she stapled out of Jackie’s sight below the wraparound desk shelf. Of course, Jackie realized Crazy eyes, unlike rational women, did not worry or care if she stapled herself. Probably even looked forward to it. After that Jackie heard stapling and a passionate gasp or two but refused to look again. Jackie saw no other visitors during her long wait.

  Eventually, Robert Arlington stepped out of his office to hand some papers to Crazy Eyes. He seemed delighted but surprised to see Jackie and invited her to step into his office.

  As she walked past the receptionist Jackie could still muster some anger. What a little bitch! Clearly, she had never even informed Robert that Jackie was in to see him. Jackie had assumed Robert was seeing a patient but that wasn’t the case. If he’d been told Jackie was present he probably would have invited her in immediately. Adding to Jackie’s anger was that the hour wait had not only been boring but was also filled with demoralizing thoughts. It had been mental torture. Crazy Eyes had effectively tortured her for an hour just to bother her or in order to amuse herself staring at Jackie. It made Jackie furious.

  About to follow Robert into his office Jackie looked to the side and down at the receptionist in order to give her a stern look. The girl’s face was lost in a dreamy expression. Jackie noted one of her hands was under the desk and her delicate forearm muscles were flexing rhythmically. That hand was definitely up to something down there.

  Dismayed, Jackie stepped into the office and pulled the ornate polished oak door closed firmly behind her.

  Robert was already sitting down behind his huge beautiful desk. Jackie approached and hesitated with her mouth open. She felt like a condemned prisoner who’d been getting by on false bravado but eventually finds herself standing on the deck of the executioner’s platform.

  “Ms. Thorpe, a lovely surprise. Have you come to update me personally on the progress of your analysis of Mr. Jones? “

  Oh, God, no, thought Jackie. The last thing she wanted to do was talk about Jones. She didn’t want to lie to Robert especially since he would probably detect it immediately. She definitely didn’t want Robert to know how little progress she’d made with Jones or how much progress Jones had made with her.

  “Actually, I wanted to visit and thank you. I am so grateful to you. I owe you for this opportunity. I have so much admiration for you and I don’t want to keep that hidden. “

  “Very kind words and much appreciated. I think it’s all going to work out splendidly. “

  Jackie knew she had to keep pushing ahead before he returned to asking her about Jones and before she backed out. She had to do this.

  Jackie wished she could be artful about this but time was against her. This had to be a speed seduction so she would have to act like a slut. Propositioning like a slut would be consistent with the slutty act she planned to perform. If she earned the partnership she could one day play it off to him as a strange atypical episode. A one time event not up for repetition.

  Jones forbid a hand job so she was going to give him a blow job. It was the lesser of two evils between that and actual intercourse. As much as she did not want Robert’s old penis in her mouth she had even less desire to have that old penis spitting semen up her vagina.

  Jackie surprised Robert by walking around his desk to him, “When I admire a man I believe in showing my appreciation. In doing what I can to help them in return. I’m sure you’ve got a certain amount of stress. I can help with that. In fact, I know just the thing. “

  Robert turned his fancy high backed leather chair sideways to the desk in order to face her as she came around. His deeply lined face was surprisingly unsurprised, his dark brown eyes flashing hunger from their deep sockets.

  As hungry as his eyes looked, Jackie knew she was the one who would be doing all the eating. Feeling near hysteria from the stress she nearly smiled at her own thought. The thought made her project ahead to when Robert came from her oral attentions. She wasn’t sure how she was going to handle that moment. She guessed she was probably just going to swallow all that old sperm. She didn’t want to leave a mess or leave the office smelling like sperm.

  Just like that she experienced a totally unexpected rush of arousal. Her actions were so bold and her thoughts were so nasty it actually made her mouth flow with preparatory saliva and her pussy begin to run with juices.

  She hesitated, her standing knees just inches from his sitting ones. Then she dropped to her knees to the carpeted floor, her hands grasping his bony knees and pulling them apart. Actually worried about rejection, she leaned forward and kissed the fly of his slacks to make clear what she was about to do and then looked up to his
face.

  He just sat and watched her and gave no obvious sign of approval or disapproval. Jackie was surprised at how stern he was but could sense the lust in the dark pools of his eyes. She would just have to dive in and hope for the best.

  She undid his belt, opened his fly, and pulled his boxer shorts down enough. She had mixed feelings when she saw his cock was already erect. On the way over she’d worried she may not be able to get it up, at least not quickly. Hell, for all she knew, he could have been gay. She was relieved that now she would be able to accomplish her mission. On the other hand, she now knew she would be accomplishing her mission. That wasn’t exactly a good thing.

  The thrill of the forbidden was percolating the liquids in her pussy. This man Robert Arlington would choose whether she would be his junior partner and heir apparent of his psychiatric counseling practice. Here she was on her knees in his office leaning her face close enough for him to feel her warm breath. He was old enough to be her father. Actually, he was old enough to be her father’s father. Grandpa Robert.

  She realized he would probably think she was trying to manipulate his decision process. Even if she pulled off the Wayne Jones analysis to his satisfaction she was sure he would always have that thought. Especially if she cut off the sexual favors as she knew she would. This was a one off. Jones had truly succeeded in permanently muddying the waters of her hoped for future business home. That clever bastard!

  Her 24-year-old mouth engulfed his 64-year-old dick. Jackie used her mouth and tongue industriously, really working that hard old cock. She felt it best to be effective in order to get this task over with. Admittedly, unexpected passion had as much to do with her fervor as strategy.

  Jackie bathed the entire cock in saliva, surrounded it with her mouth and tried to get her lips as far down as she could without gagging. Whenever it got to be a little too much she pulled her mouth off and licked firmly up and down the full length of the shafts sides and then up and down the tender underside.

  Jackie tried to lose herself in her task, pretending it was a disembodied ownerless cock. Robert’s grunts of pleasure made that mental self-deception a challenge. On the other hand -- or mouth -- the dick did not seem like an old one. It was as hard as a piece of driftwood, tasted salty like any other cock, smelled like cock, and leaked pre-come well.

  Jackie was surprised when, as she took a turn wrapping the cock in her mouth and inching her head as far down as her gag reflex would allow, Robert suddenly grabbed a handful of hair on either side of her face and jammed her mouth down. The move drove his cock up into her throat and it bent partway down to angle even further in. It happened in less than a second and with tremendous force.

  Robert held her face all the way down, his cock as deep as it could go, and would not allow her to pull back even one millimeter. Jackie was in some discomfort. The cock had pushed her tonsils out of the way and made her feel like she couldn’t breath. In truth, her nose was pulling in air just fine through the mat of Robert’s gray pubic hair. Jackie was surprised by Robert’s boldness and by her own ability to take that dick all the way in. It was odd she felt degraded but also a bit proud.

  She found her focus and used her tongue to give his cock as much sensation as possible. It wasn’t really fair because she shouldn’t reward him for being so rough but she didn’t know how long she could avoid gagging or worse and was feeling a lot of urgency. A long minute went by this way. She was feeling frustrated. Somehow, she’d thought an old guy would come more quickly -- at least while being sucked off by such a young and attractive woman. She was also frustrated sexually. The entire episode was really turning her on and her pussy wanted attention. She was determined not to humiliate herself by fingering her sex in front of Robert.

  Then Robert pulled a twist of hair painfully and used it to draw her mouth up and off his cock. Saliva drooled out of her mouth. Embarrassed, she used the back of one hand to wipe it off her chin as she looked up at Robert to see what he wanted.

  “You’ll continue in the same fashion in just a moment. First, get your cute butt under my desk. Get all of you under there and face me on your knees. I have certain fantasies and obviously you can now be of great assistance in helping me achieve one of them. “

  Intellectually numbed by the heat between her legs, all Jackie could do was obey. She knee-walked under the huge desk and backed in facing the square of light. That light was eclipsed more and more as Robert used his feet to pull the chair on rollers in place to block her into her crammed makeshift cell.

  Robert took a moment to peer down at her. His normally kindly-looking face looked quite mean to Jackie.

  “Well, Ms. Thorpe, you’re a regular Jackie-in-the-box now. Make it good and, if you don’t earn the position -- and you assuredly must still earn the partnership no matter how good of a blow job you deliver -- I’m sure I can create a position for you as my desk-dwelling cock masseuse. Now, get back to it. “

  Robert rolled his groin forward. Jackie went back to work, re-warming the evaporating spit on his cock with her hot mouth. She heard him groan in satisfaction. She marveled at how the old guy hadn’t been thrown by her slutty behavior and had quickly and fully taken control in order to make the action even more twisted.

  The silver lining to the dark hole she was crammed into was that she could now touch her pussy to her heart’s content without being seen. She could smell the scent of her pussy though it was smothered by the smell of cock and foot odor.

  Her shaky fingers got up under her skirt and down into her panties. Fingers slipping between the folds of her vulva released streamlets of juices down both her thighs. She moaned around his cock and worked her pussy against those penetrating fingers. It didn’t take long for her square of space to smell a whole lot more of pussy.

  When Jackie felt Robert begin to pull his swivel chair back out again she released his cock and hurriedly pulled her fingers out of her pussy. When she looked up the leer on Robert’s crinkled face told her she’d pulled her fingers out a little too late. That or the obvious smell let Robert in on her secret.

  “I don’t mind you fingering yourself under there just so long as you don’t lose track of your main goal, sucking cock. I also multi-task. In fact, I’m enough of a professional I’ll continue with my work. I think while you take dick-tation, I’ll call the lovely Hannah in for the more standard dictation. “

  Jackie knew he must be joking but didn’t find it very amusing. She didn’t give it much thought when he pushed the chair back in place and his cock was back inside her mouth. Her mouth had felt quite empty without it. She was actually hungry for his load. She heard him press what could have been an intercom button if he hadn’t been joking.

  “Hannah, would you please come in for some dictation. “

  Jackie was relieved she didn’t hear a response. He’d really had her going there for a second. Who knew the old coot had such a wicked sense of humor? She wondered when he was going to shoot. She was getting a little impatient. Not so much to get the event over with. She just wanted that dose of sperm.

  Then she heard the office door open. My God, was it really Hannah, a. k. a. Crazy Eyes? She’d seen Jackie enter with Robert and had to know she hadn’t left yet. There weren’t many hiding places in this office. Would she successfully conclude Jackie was under the desk?

  “Here I am, Dr. Arlington. Is it dictation you want, or dick-tation? I brought my notepad just in case you did mean dictation. “

  “You will need your notepad. It will be standard dictation this time. “

  Jackie realized then that Robert was using Hannah for sex on a regular basis. So he hadn’t been ignorant of her odd behavior. He just didn’t care. No wonder why he had the girl with the bad attitude greeting his patients. Between patients she had extra duties and that was how she kept her job. Robert must have terminated that poor older lady she’d previously seen at the receptionist
desk, just in order to replace her with someone he could use for sex. What a jerk.

  Jackie was appalled by Robert’s and Hannah’s apparent relationship though she realized she was hardly in a position to criticize, either figuratively or literally. She kept sucking and licking though she did her best to limit any sucking or slurping sounds. Hannah did not react to Jackie’s absence. Perhaps she thought Jackie must be in the connecting office she would one day occupy if all went well.

  She heard Hannah sit opposite Robert’s desk and Robert began dictating a letter. Jackie couldn’t help but wonder who the letter was for and how Robert kept his voice steady despite her fine oral attention.

  “Dear Sir, I, your humblest servant, am sending you this note to thank you for your kind and considerate efforts on my behalf. You have brought me incredible pleasure through your expert endeavors. Your first gift has seen frequent use and has worked out even better than anticipated. It’s amazing really. I’ve had such a long successful career and yet have never had as much satisfaction as now. I owe it all to you. “

  Robert paused a long while. He was thrusting up into Jackie’s attentive mouth. She felt like her efforts were succeeding. She wondered at her dread going into all this. It was actually all so simple and easy. Just please and do as she was directed. She also wondered at his dictated letter. She did have a sense of foreboding but she was preoccupied trying to keep her lips sealed around his shaft in order to prevent any slurping noises. He must know his thrusting was making it difficult for her. Surely he wanted to keep their sexual act a secret from Hannah?

  “Dear Sir, just to keep you as informed as you like, even as I dictate this letter to the slut who was your first gift, your second, the loaner, is under my desk enjoying dictation from my dick. She has a useful and proficient mouth. You really should take advantage of that oral resource. If you haven’t already, of course. “