Ms. Date’s New Boss
She had only worked in the private office for a short time, nine weeks to be exact. She was hired as a part-time personal assistant to handle the phones, filing, correspondence and anything else her employer needed; while he logged in hours of computer time barely taking a moment to grab meals for himself. Her desk was a spartan table and chair positioned, just outside his own office, facing his door that was rarely closed. Due to the office structure she was frequently required to enter his space to deal with files, take notes and generally keep things organized on his massive floor length tiger oak desk. The large beautiful piece of furniture faced the entrance to his office, and subsequently her desk, giving him a commanding position in the room. With his large screen laptop permanently in position at his fingertips, she often felt as alone as she maneuvered through her days’ tasks.
Her new boss was a large man, well over 6 foot, and his broad frame filled the custom leather chair in a commanding way. Aside from the few instructions he gave her and the few phone conversations that he was required to handle he was, more often than not, a quite man. When he did speak his voice was smooth, even and deep. It struck her, from the moment she interviewed for the position, that she could easily be coerced into doing almost anything if he would just use his voice to ask. He was even handsome, which made spending her time around such a workaholic that much more difficult. Not only did he dedicate his time to his work he did so with a discipline she had not witnessed before.
She decided that she wanted to catch his attention today, make his work days more enjoyable, so she began to hum as she worked about the office flitting from task to task. The more furrowed his brow became the more she made it a point to work nearer to his desk humming away with a giant smile on her face. That is until he pushed his laptop away, for the first time since her interview, and simply stared at her. As she felt the weight of his stare a blush bloomed in her cheeks. When she came within his reach, he grabbed her wrist and pulled her firmly toward him and said quietly while simultaneously snaring her eye contact “What do you think you are doing Ms. Date?” Captured by his voice, his eyes and his hand, now more gently grasping her arm running his thumb slowly up and down the inside of her wrist, she swallowed hard to try and regain her voice and moisten her suddenly dry mouth. “H…Humming Sir? I… I only wanted to make you h…happier,” she stammered “you looked so frustrated and…” His tension eased a bit at her words as he interrupted her. “In that case, in the future I will let you know when and how to make me happy Ms.Date.” With that statement he released her and pulled his laptop back into position and continued his work.
Escaping to the private bathroom, down the hall, she sat down breathing hard and surprisingly excited. She could feel the moistness in her panties from just that one encounter, despite it’s lack of overt sexual nature… ‘or was it there after all?’ She asked herself as she let her fingers wander over her swollen breasts, kneading them, and tugging briefly at her hard nipples. Her hand slid down to her trousers and slipped into her panties to feel the confirmation that she was indeed soaked. She relished in the lubrication coating her fingers as they glided over her clit and lips while closing her eyes suddenly wishing it was him touching her. She couldn’t dare to orgasm in here, she thought, since he would surely hear her with such close proximity to his office. She put herself back together and purposefully didn’t wash her hands. She liked the smell of her arousal and decided it would make an interesting twist in their day. Regretfully it did nothing. He continued to work without distraction, unlike her, and 5 o’clock arrived much too swiftly. Time for her to leave. Mournful that her plan failed she decided to step up her game for the next day she was scheduled to work.
That next morning she showered, slid on her thigh high stockings, attached her stays, pulled on her short tight black skirt, cinched her Demi bra in place and slipped into her white silk blouse. The heels she chose were still a bit precarious to wear, for a woman so accustomed to flats, but she decided that it would be entirely enjoyable to land in his lap ‘accidentally,’ she grinned, as she fastened the buckle. Cinching the belt on her favorite red-orange double breasted trench coat, she was half tempted to remove everything but her stockings stays and bra then throw her coat back on. ‘Another day’ she quietly convinced herself, smiling at her idea. Walking out the door to her apartment made her heart flutter with anticipation. Today was going to be full of surprises.
When she arrived he was already in his office, miles away yet, sitting right there. She wanted his reaction, his attention, as her coat came off. Although she could see his eyes, they were both firmly glued to the computer screen as she passed back and forth getting her purse stowed in a closet and checking the voice mail messages. When she finally gave up, she turned around and peeled the belt loop from about her waist. The moment her outfit was revealed she though she heard him growl yet, when she turned, his eyes appeared to never have left his screen and his face remained set. She sighed as she walked up to pull a hanger from the closet and hung her coat.
“Ms. Date” she jumped at the sound of her name, “Yes Sir?” “I need you in my office… now.” His voice sounded serious but her secret smile was hard to contain. She walked in, as outwardly professional as she could muster, and paused once she entered the room he had called her into. “I have a list of errands that I need accomplished before the day’s end today.” Without looking up he handed her a piece of paper with hours of tasks . “I will require lunch as well; however I will leave that up to you to decide from where you will pick that up. Thank you, I will see you around noon.” She stood for a moment staring blankly down at the list with her mouth slightly agape. With his list in hand she walked back to her desk, pulled her coat and purse from the closet, opened the door and left without another word.
Readjusting her plan she set out for the first task. By reordering the list she knew she could accomplish more that half the duties before noon. Each involved picking up a package from a variety of stores throughout town. The odd part was that, each place she visited, there was at least someone at each business who was openly looking her up and down. She felt somewhat on display and as a result she refused to remove her trench coat, preferring to keep her outfit choice private. By the time 11 o’clock struck she was almost finished but oddly keyed up from all of the flirtatious attention that had been afforded her. The last thing on the list was about 15 minutes away and luckily there was a nice restaurant next door that she knew well and could also pick up his lunch. The air was crisp, and cooled her heated cheeks, as she drove to her final destination. Upon arriving she popped into the restaurant to order before picking up the last package. Once again she was given an overly attentive welcoming and again she smiled, courteously thanked this last shop owner and headed back to the restaurant.
The crowded eatery was like a gauntlet for her already tight skin. She managed to maneuver up to the counter, pay and retrieve the order then make her way back out without losing her mind. Twenty minutes later, a bit calmer and with 10 minutes to spare she placed his lunch on the edge of his desk. In just 3 short trips with arms loaded she had all of his packages in from her SUV and on her desk. Again she removed her Trench Coat, with very little ceremony this time, hung it in the closet then walked over to her bag, pulled out her yogurt and spoon and sat to enjoy her own lunch. Today’s flavor was her favorite, Chobani’s Passion Fruit. The tangy sweet flavors burst vibrantly on her tongue intermingling with the natural greek yogurt flavor as she slowly spooned each moist dollop into her mouth. She moaned a bit over how fulfilling the flavors and textures danced on every tastebud.
She hadn’t realized she had closed her eyes until she heard him clear his throat mere feet from her chair. Her eyes sprang open to see him standing over her. “Sir? Is there something wrong” From his positionshe knew he could see straight down her blouse. He chuffed and then said “I want all of these boxes in my office now Ms. Date, not on you desk. When you are done your” he wrinkled his nose at the yogurt container “lunch, you may go out and finish my list.” She quickly placed her cup on her desk and scurried to place the boxes in his office. She knew bending over would reveal her stocking tops and even possibly her absence of panties so she chose to place them on the floor next to his desk as he hovered watching her next to her own desk ominously. After her third trip, and all of the boxes were settled, she turned to find him in the doorway. “Ms. Date, did you complete my entire list this morning?” “Yes Sir.” She couldn’t tell if he was impressed, frustrated or proud of her from the look on his face. “I was expecting that to take you all day. I don’t have any more tasks for you today, you may go home.”
Her heart fell at the thought of leaving. “Oh… OK” she muttered as she moved to walk past him. “Unless” he paused. She looked up with anticipation. Their bodies close “Yes Sir?” He leaned in “Do you still want to make me happy Ms. Date?” Her eyes lit up and she said enthusiastically “OH, YES Sir!” A wicked smile broke on his face and he said “Wonderful, now be a good girl and lock the door then come in my office and close my office door behind you.” Her heart sped up as she rushed over to the front entrance and turned to latch then breezed past her desk and into his room pulling the door closed behind her. When she heard the final click of the handle she stood with her back to the door. Her excitement had sped up her breathing and her breasts rose and fell straining at her blouse with every inhale. Her skin felt tight and ached to be touched.
He approached her slowly and said “What am I going to do with you?” She quickly said “Anything you like Sir.” His eyebrow cocked and he questioned her “Anything? That is a VERY broad term, I havent even told you what would please me. It could be very uncomfortable for you. I hardly want to have you calling the police or suing me for harassment.” “No Sir, I agree. Please tell me, what is that you want? How can I please you?” He strolled around his office like a shark getting closer to her with every pass until he stopped directly in front of her, leaned in and growled “Well first I think you need a spanking for neglecting to wear your panties today. I can’t have you traipsing about exposing yourself to my vendors and clients.”
“No Sir, of course not, that is why I wore my Trench Coat the entire time I was gone.” she confessed. “Well that was unexpected. Were you not treated respectfully?” he inquired. “Oh yes, I was treated with a great deal of kindness. It was even a bit embarrassing. I felt so ‘In the Spotlight’ everywhere I went. I am in no way an individual used to excessive compliments so I just tried to get in and out of each business as efficiently as possible. They were all very nice.” then she looked him directly in the eye and said “But if you still need to spank me… ” her lids lowered to stare at his lips as she licked and nibbled her own. What happened next happened suddenly like a strike. First he was in front of her, Then next his tongue was in her mouth and his hands were on her, one holding her hands above her head and the other roaming free.
She sighed as his hand coasted down her shoulder, pausing to roughly grope her breast and nipple then drift down her leg to the hemline and retrace it’s path along her inner thighs over her stocking tops, onto her bare leg and to the crux of her core. She widened her stance to allow him better access to her needy flesh. He moistened his fingers in her flow of excitement before he slowly inserted two long fingers deep inside her. “Now Ms. Date,” he began “I would like to ask you a few questions.” Her gasps for air, as his fingers moved in and out of her, clouded all practical thought. “Sir?” she struggled to speak as her body leaned heavily against the door.
“Ms. Date did you, by any chance, wear this outfit today in an effort to get my attention?” and with that question his fingers tapped rhythmically on her inner walls stimulating her arousal further. “YES!” she panted wildly. “Now is that a yes to this?” as his fingers literally plucked at her pleasure center, “or were you saying yes in answer to my question?” Her back arched and with a strip of sanity left she said “Both!” He whispered “Good girl” and she felt he climax rush through her body.
He quietly waited for her to regain a modicum of composure before his next statement “Are you prepared to take responsibility for your actions?” On an exhale she said “Yes Sir.” His hand snaked into the base of her hair and grabbed a healthy portion and then leaned in and whispered right into her ear. “I am going to march you over to my desk, bend you over and spank you very hard. Do you agree Ms. Date that you do indeed ‘deserve’ these consequences for your actions?” With her eyes cast down, her nose swimming in the heat and scent coming from his neck, her post-orgasmic state told her to lick his neck so she did. She paused to say “Yes Sir” before she kissed and sucked this time. “Mmmmmmm” It was in that moment he pulled reluctantly at her hair, detaching her mouth from his nape, and marched her to the opulent desk. He had already cleared it prior to her locking the door. Even in her dazed state she realized that in order to clear his desk everything must have been filed and his massive wooden furniture was always full.
In the moment it took to traverse the room and throw her down on the desk, with her ass in the air, his own climax began to test his limits. The first smack was capricious. Only one person knew how hard it was going to be and it wasn’t her. The pain in his own hand was an initial balm for the threatening precum seeping from his cock. Throwing up her skirt, picking up a rhythm and alternating a pattern he stimulated her cheeks to pinken. The initial shocking chirp that erupted from her lungs after the first blows to her ass turned quickly to moans. She tried to remain still but with every blow she jumped and arched her back to feel the delicious blows closer to her center. Her own juices flowing and seeping down her inner thighs she was already close again.
The absent sound of his hand cracking down upon her flesh was followed by the feel of his palm smoothing over her heated ass, brushing teasingly through her dripping folds only to leave again to massage her cheeks further. She tried to follow his palm with her ass aching to have his fingers caressing her sensitive crux to no avail. Despite the heat radiating off of her reddened ass when his hand stopped she shivered as if the loss made her cold when, if anything, she was on fire. She jumped again when she felt his hands on either side of her hips. Without any other formality his cock pressed unnervingly slowly into her. Once he was fully seated inside her, he held for the moment relishing the spasms of her muscles desperately trying to gain friction as well as purchase on his slippery member. Instead of giving her the expected withdraw, she was clearly waiting for, instead he pushed in farther anchoring her between the desk and his own hips and began rotating his hips while fully buried.
The pressure of his cock swirling inside her created the simultaneous sensations of his base stretching her opening and the tip caressing her cervix like a slow dance. He was so deep her legs shook. The long low moan that erupted from her throat was what he was waiting for. He withdrew for the first time as slowly as he entered her until only his sensitive head remained within and feeling her desperation grasping him, begging for his thrust, as his own lust took the forefront. With his pause he warned her to grasp the edge of the desk to either side of her hips. He could hear her nails scrape the underside of his desk in anticipation. His cock twitched the moment before he slammed into her. The wet sound of slapping as well as her breath sawing in and out filled the room as the humid smell of her sex seeped into his nostrils. She felt the bloom of a bruise building on her thighs as he pounded her up against the desk over and over welcoming the pain in contrast to the sting on her ass and the throb in her tight wet sheath. A fine coating of sweat coated her forehead as he began to buck and thrust irregularly. She felt him swell further and the repeated battering of his balls on her clit sent her into a second more powerful climax. The clamping pressure sent him over the edge as he pumped his seed deep inside her staying there until it was all delivered.
He leaned down and whispered in her ear “Stay.” Laying across his desk, legs limp and catching her breath she closed her eyes recovering from the assault to her body. Her affirmative moan made him chuckle as he opened his office door and walked down the hall. She recognized the sound of the faucet turning on in the bathroom and heard him through the wall saying, “I know everything that goes on in my office Ms. Date, you should keep that in mind next time you touch yourself.” Her eyes opened in shock at how clearly his voice came through. Even the wringing out of the water was heard with little dampening. She scanned the wall for an explanation for the ease of communication. She saw no grates, no vents that would be a clear reason but accepted her underestimation of her new employer. In fact, she was aware at how quickly everything changed since that one act and how his simple command to “stay” was said to demonstrate a portion of his omnipotence.
She heard him return to the room but decided to keep her eyes closed. Unable to find a reason for it matter what happened from here, on she remained still and sated. She felt the warm soft damp terry cloth gently swipe across her sensitive skin followed by a fluffy towel patting her dry. The sound of a knife being dragged across the top of a box and the dual pop of tape breaking, something scraping along cardboard then a snap of a lid like a bottle of lotion. She felt a cool ointment smoothed over her heated ass cheeks with his fingers messaging it into the muscle. A slow smile spread across her face at his tender care and clear homage to her ass. A second box was popped opened and a soft brush against the inner walls was barely discernible except for the stillness in the room. “I need you to stand Ms. Date” She found her legs and rose. “Please sit” He had folded and placed a fluffy red towel in his own big leather chair and was inviting her to have a seat.
Once comfortable, he knelt at her feet and slowly unbuckled her steeply heeled shoes massaging each sole till she groaned in relief. “You may NOT wear these to work again… are we clear?” Responding meekly she replied “Yes Sir.” After removing her stockings, he rose and went to the pile of boxes again and opened a third. She clearly remembered picking up this box from a shoe store and when he turned presented her with a pair of elegant flats which he slipped on to each foot suspiciously confident of their perfect fit. Glancing back at the pile of boxes she became more and more curious as to the contents of each one. Six more boxes remained. “Please stand, I want to be sure they fit correctly.” Standing, her legs still shaky and unsteady, she took a few steps away from him and stopped. Lowering her head, looking down at the most beautiful and most comfortable shoes her eyes filled and spilled over. She wept silently at his generosity. She could feel the heat emanating from his body at her back, felt his hands on her shoulders then turned her to face him and pulled her chin up to see her face. His brow furrowed at the falling tears. Gathering her into his arms, pulling her back into the chair with him, into his lap, he held her tight as she began to weep openly, rubbing her back allowing her to bare herself.
When she recovered she began to apologize “I’m so sorry…” at which he stopped her “No. You will not apologize for expressing yourself. That goes for all emotions. You will, however, communicate with me why you believe you are experiencing this, when you are ready, but I want you to be open and you deserve to have a whole range of emotions.” She rested her head back on his shoulder, closing her eyes and sighed deeply. A sudden realization hit her and she pulled away. “How is this going to affect…” Again he interrupted her “You have several options available. You may carry on your duties as per usual, if you want to continue I will need see you outside of the hours we have deemed office hours. If working for me is a problem you are welcome to end your employment at any time and if an intimate relationship with me is an issue then you may end it here, just say the word. Just know this, I want you and if you want me as well then I will want to do things like this to you often.” His words had trailed off in a low lustful tone that renewed her arousal.
He had been soothing her, running his hand up and down her thigh. With the spoken words hanging in the air his grip had become more rough, more like a deep muscle massage and edging back up to her sex. Her gasp as he worked his thumb into the bruise that had yet to bloom was followed by a moan as he eases a finger between her thighs to tease her sensitive clit. “I already need to use you again” he growled into her ear. “Yes…please” she whispered. With her submission he jumped up holding her close, whipped the towel off of his chair and placed it onto his desk in back of her. Pulling her roughly into another passionate kiss he yanked her skirt down, tore her shirt open and wrecked her bra getting her naked. He then backed her up to the desk and guided her to sit close to the edge. Breaking their lip lock and holding her neck he guided her to lay back. She felt awkward with her legs hanging to either side of his hips. Dragging his hands over the newly exposed skin of her torso, down her breasts tweaking her nipples and over her belly as he pulled his chair back to the desk.
Raising her head she watched as his he opened the top drawers to either side of him, picked up each leg and placed her feet into each drawer edge. With a palm on each ankle she felt them skate up her shins then tuck his fingers under her knees and lay her wide and open to his inspection. His eye contact never broke. When he lowered to lick her moist folds her head fell heavily to the desk with a thud. Drunk on lust the dull pain from the back of her skull receded quickly in the light of the tongue stroking, licking and tasting her to a rhythm that made her toes curl and go numb. Her hips began to rock against his face to get him closer, deeper then he thrust his tongue into her aching pussy. The moans she had been trying to suppress were suddenly set free. She was close and he knew. He pulled away and heard her very audible opposition to his decision. “Please” she begged fruitlessly. Hearing another box open she looked up to find him inserting batteries into a dildo with a vibrating hummingbird. I was the exact one she had at home so she knew precisely how it would feel and her eyes went wide in anticipation.
From the same box he pulled a bottle of lube pouring some into his hand he began stroking his cock. Watching him made her breathing hitch and speed up to a pant. Placing his cock on her flesh he guided it down and down picking up more moisture as it descended. Placing it at the opening to her ass she jumped until he settled her with his reassurance. Holding her firmly he presented the toy, let her watch him turn it on and place it inside of her. Her previously cooled impending orgasm came screaming back as he kept stroking his own cock pressing firmly against her tight bud. Just as her orgasm began to crest he thrust inside of her ass. Her breath left her in a whoosh at the sudden feeling of over fullness. He stayed there deep inside as he increased the vibe level on her clit. Lifting her knees to spread and tilt her hips farther up he began working the rubber cock in and out of her as he began to move slowly, allowing her to adjust to the new sensation. The vibe increased again and she felt the climax again rushing in and began bucking as her muscles wound tighter and tighter. Her scream was followed by his own series of bucking as her he fucked her clamping ass until he filled her tight hole.
Both panting and exhausted he unceremoniously fell back into his chair and placed her feet carefully back into the drawers her legs falling open sated and limp. When he recovered himself he again said “Stay” before leaving the room, as if she was going anywhere. He had destroyed her silk top and bra and she had no clue what she could wear home other than her skirt and trench coat. She giggled to herself about her earlier thought of arriving so scantily clad. She was still giggling from the combined thought as well as the adrenaline dump subsiding in her blood stream when he returned. “Something funny? Remember, I can hear everything you know.” Her smile brightened and she said “I was just laughing at the thought of having to move when you ordered me to ‘Stay’. Where would I even go, my clothes are destroyed and when I imagined putting on my trench coat and being naked underneath I remembered that this morning I actually had contemplated coming to work in just that with only my stockings, bra and panties underneath.” Crooking his eyebrow with a sly grin he inquired “Is that so Ms. Date?” Blushing furiously now she averted her gaze and said “Yes Sir.”
Pulling her up from her reclined prone position and offering her his hand for stability he guided her to stand and escorted her to the door of his office. She hesitated a moment, knowing the outer door was clear glass and anyone passing would see her nudity from across the often crowded parking lot. “Do you trust me?” With a shaking voice she said “Yes Sir.” “Then open the door.” She turned the knob and swung the door wide despite her fears. Looking to her right, light filtered weakly through edges not magnetically attached opaque fabric laid carefully over the glass. She looked down to see the lengthy thin box she had almost dropped trying to maneuver it into the office. She glanced back to see him carrying the most fragrant of the boxes picked up from the Lush store. Drooling over the lotions and bath bombs she almost cried having to leave the store without buying something for herself, but she knew her time frame was close and left on a broken sigh. Now curious, with his hand at the small of her back he directed her to the left, down the hall passed the small powder room to a door at the end of the hall.
Leaning in close he reached around her and turned the knob. The open door lead to a set of steps going up. She had not realized that he had access to the second floor or what was up there. As she ascended the staircase the sound of water caught her ear. Once at the top the space opened up to beautiful hard wood floors. With his hand once again at the small of her back her steered her toward the sound of water. The humidity increased as they approached the steamfilled room. A large tub with jets sat to the back of the room. “Go on, I want you to soak.” He opened the box in his arm and tossed in a fizzy pink bath bomb with a tiny rose and began placing Shampoos, Conditioner and Lotion within her reach as she sat on the edge and swung her legs into the hot bubbly fragarent water. Once again her eyes filled with tears at the humble feelings she felt. “Thank you” was all she could say around the knot in her throat. “You’ve more than earned it Ms. Date.” “Please Sir, please call me Zoey” she begged. “I will call you what I like but if you prefer Zoey I will make an effort to incorporate that into my vocabulary but I can’t make any promises… especially when I am fucking you.” Her breath caught. “Now, if you will please excuse me I must retrieve a few things and allow you to soak before I take you again.” Leaning in he grabbed her face, kissed her passionately and tweeked her nipples making her moan again before pulling away and walking out of the room and sutting the door behind him.
Immersing herself into the heavenly warm liquid she pampered her skin and hair, allowed her fingers to become pruny and soft, closed her eyes and let her muscles turn to gelatin. A soft knock on the door roused her from the dream. She opened her eyes to find more red towels in his arms inviting her to be swathed in cottony soft pillows of terry cloth. “Come” was all he said before she rose. Carefully drying every inch of her skin the perfume of the Lush products clung to her body like a light aura. “Let’s go out.” He pulled the door open and the remaining boxes were set in two piles. One large to the left and two medium to the right. “Please choose.” She tried to recall the stores she visited. The haze of her afterglow left her mind blank as she looked from left to right then back agian. “You realize that, either way, they are all yours anyway. I will not hesitate to choose for you.” With a smirk on her face she said, “Do your worst.” Stalking toward her he replied “Oh, you definitely shouldn’t have said that!”