Last of the Year

Story Info
She made a deal with him for one last orgasm for the year.
7.5k words
4.19
26.5k
11
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Prologue: Just one more week my boy?

She was preparing in the bathroom, he was getting himself dressed. It was going to be a good night he could just tell. She had been well tended to during the day and now they were going out for dinner at that fancy restaurant that She has wanted to go to for weeks. As She walked out of the bathroom dressed to kill his eyes scanned, the blue heels caught his attention first. But of course they would it had been three weeks since She had last allowed him to enjoy one of Her orgasms. She knew this was where his focus would be and the dark stockings that led up from those bright blue patent heels drew his attention up Her body.

his breath caught as he noticed Her knees and then the finally came to the all too short dress that She was wearing. he breathed in a shuddering breath as his eyes continued rising, the deep blue of the dress matching those shoes on the bottom and just as he came to the middle of it he found that She had worn Her new corset. The black and silver glinting in the lighting covering Her middle and pulling his attention to Her already ample bosom. This was now accentuated even further as they were pressed up behind the dark leather. he swallowed the knot that rested at his adam's apple and then his eyes rose to Her face. The smirk that She wore on her deep red painted lips was burned into his mind. She chuckled at his plight as She noticed the bulge rising in his pants.

"Oh, this is going to be such a fun night foot boy, before we go You really must SEE my heels," She taunted him knowing full well that he had already eyed them up in taking in his first view of Her on the evening, but he knew just what She meant. he sank to his knees and then leaned forward to place his palms onto the hardwood floor of Her bedroom. He crawled forward eyes kept to the floor until those shiny blue heels were in his view. The smirk on Her lips grew to a full smile that he would not see as She lifted one foot off the floor and pressed the toe to his lips. As She did She heard the moan trill through his throat. She knew he loved this and hearing him react so easily to it sent a trill up Her leg.

"Good boy," The words filtered down to him and even here in private he would blush as She pulled the toe of Her heel away replacing it with the other before crouching before him. As She did Her legs part displaying the fact that She was in-fact not wearing any panties, her nether lips parting slightly showing off a glisten that showed She was just as aroused as he was. Along with the view of Her recently shaved sex he noticed that the stockings went all the way up Her thighs to be held in place by a garter. Her hand then pressed to his cheek and pulled his eyes up, cupping the cheek and beckoning him to rise and stand before of Her. As soon as his legs had straightened She leaned in kissing his lips passionately and reaching down to grasp Her property.

"Are You wearing Your panties like i ordered You to until the end of the month?" She felt him shiver and nod before he responded to the affirmative. She let out another chuckle and squeezed Her cock once again. "Who knows maybe someone will find out about those silky panties that You are wearing tonight," She teased him like this often but thankfully in his mind She had never let that particular cat out of the bag when She made him wear them.

Once She had finished with giving him a hard time She turned, tugged at Her cock gently and told him it was time to go to the restaurant, their reservation was for a half hour from now. They both got in the car, him driving of course and made their way to the restaurant. As they pulled up to the valet station he made his way to Her side, opening the door for Her before the valet could even think to do so. As She slid Her legs out of the car he whimpered softly under his breath as he once again caught sight of Her stocking tops. She took his hand and stood once again praising him with his favorite phrase, "good boy." he smiled and turned offering Her his elbow to take as they made their way inside. The maitre'd greeted them and walked them to a central table, the long table cloth hanging almost to the floor.

As they approached the table he stepped in front of Her pulling Her chair out and allowing Her to sit daintily on the seat. he tipped the maitre'd and asked for the sommelier to be sent over. Ordering a pricey bottle of wine they sat perusing the menu for a moment, though for him that was very short lived as She leaned forwards, Her toes sliding up his leg and then pressing into Her property daintily. he let out a moan that drew a little attention before he regained some semblance of control and only shook in deep desire instead. Her toes and the ball of Her foot manipulated the hard on that he now had as She had fun forcing his breath to be deeper with catches and gasps.

Once the bottle of wine came over and was deemed worthy by Her, the waiter came by her boy felt the ball of Her foot press hard into him as he was about to speak and order and instead She ordered for him. he blushed a little once again and noticed that a few of the nearby tables were once again looking at the two of them. She smirked across from him and then spoke again, "i know what you would want off the menu anyway, boy," She stressed Her term of endearment and accented it with a stroke of Her cock beneath the table, "Now after such a lovely surprise coming here for dinner i have a surprise for you" Her eyes twinkled a little and he asked what She could have possibly got him.

"Well My boy, i have decided that you," again accenting that She was talking to him by pressing into the hardness that was now leaving a wet circle on the silken panties that he wore, "are to have one last orgasm for the year." He let out an unwanted to moan as She stroked at Her cock under the table and his eyes rolled back in his head before he looked into Her eyes and thanked Her, She smiled a wiley smile as She brought him right to the edge. "I haven't decided when yet but it will happen, I do hope that you enjoy the teasing until I choose to allow you to enjoy once more." he shivered and then She withdrew Her foot just in time for the appetizer to be delivered.

The rest of that evening was a blur to him, She teased him senseless and then after they got home he thanked Her orally, over and over again. She couldn't wait, just a few more days and it would be new year's eve, She knew he would be delirious by then after a month of being so severely denied.

Chapter I: Getting Ready

A little over a week later he found himself kneeling next to the bed, his head buried between Her thighs listening to Her muffled moans as he serviced Her. Her fingers knotted in his hair as She pulled him in directing his mouth just where She needed it. The raging hard on that he sported had been that way most of the time that he wasn't in the office (and much of the time that he was for that matter). For the past week She had been sending him a steady stream of provocative pictures, suggestive texts, and orders during times She knew he was on break. he was so horny right now that the simplest little suggestive phrase turned him into a ball of desire.

As Her screams echoed in his head once again Her thighs gripping his skull and Her heels digging into his back he moaned in response into Her throbbing sex. She came on his tongue again and as Her legs slacked one pulled away from his head Her toes pressing into his shoulder telling him that She had finished. "Mmm those were a very delicious set of orgasms foot boy, I love how well your tongue works when you have been waiting this long." She always teased him and reminded him just how good that orgasms felt when he was this horny. She looked down at him and smirked as She could see it written on his face that he wanted to cum so bad. She chuckled at him and sighed heavily, "Well it is four o'clock foot boy, I think it is time to get ready for tonight, crawl into the bathroom and draw me a bath, you know my favorite preparation, I will be there soon."

his knees scraped along the floor as he obeyed the veiled command and crawled his way from the bedroom and into the master bath. he gathered the coconut bath salt and ran Her a hot bath filling the tub about half-way as he waited. She was only a few minutes behind and as soon as She stepped in She reached down swiping Her fingers under his nose and leaving Her scent there for him to smell while he was bathing Her. "Now foot boy You are to clean me we will start at the bottom and You can work Your way up, in and kneel in the water."

he nodded and replied with a simple yes Mistress and moved inside of the tub, kneeling at one end before She moved into the tub and then sank slowly into the water. One leg slipped between his legs drawing a moan out of him so easily once again as the toes slid over the length of his shaft. "Mmm My cock is so hard still i will bet my boy cannot wait to enjoy the last orgasm of the year that I promised him." Her toes danced along the bottom of his shaft and he shuddered meekly answering to the affirmative.

The leg that was outside of his legs lifted from the water, the tinkling of the water droplets piercing the surface of the water. he lifted his arms with the loofa and began to clean Her toes, and the sole of Her foot, Her ankle and all the way up Her leg as he reached Her womanhood She gave him the look to stop and pulled the leg away dipping it back beneath the water to replace the other leg and once again tease another few seconds of moans and increased want out of Her foot boys throat.

She smiled an innocent smile and taunted him a little more, "is there something wrong foot boy?" he shook his head as he replied to Her and She wiggled Her toes a little more cloyingly replying once again "are You sure, You seem to be distracted." Her foot now resting on his shoulder waiting to be washed by his hands before he struggled to grip the loofa that he hadn't realized he dropped when Her toes tormented him once again.

his trembling hands retrieved the loofa and began to cleanse Her body, sensually making his way up Her leg once again. As he reached Her thigh beneath the water he looked up this time She did not stop him but instead spread Her legs allowing him to wash between them. Her eyes locked on him and She cooed gently and then abruptly She ordered his hand to stop what he was doing. his hand pulled back and She smirked, "good boy," She once again rewarded him and he smiled breathing in deeply his nostrils filling mostly with Her scent though the mixture of coconut and lavender from the bath was also lacing the air now.

Her hand reached down and guided his hand to Her stomach and She nodded which he understood meant to continue his current duty in cleansing Her for the evening. She leaned Her head back as his hands made their way slowly up Her torso and wiped away the feeling of sweat from the day's events. Once he reached Her breasts Her eyes popped open as the sensitivity of Her nipples was piqued a gasp from Her lips though his hands only momentarily stopped there. he was being so good today that She almost wanted to give him his 'present' right now.

She squirmed a little and then pulled back, slowly standing and turning around allowing him to look up the back of Her body before Her orders were made clear and he began washing the back of Her legs up to Her bottom. From there his hands continued working their way up, slowly washing over the small of Her back. As his hands reached as high as they could he stood slowly, cleaning up Her back and over Her shoulders just below where She had raised Her hair to keep it dry.

A few moments later She stepped away and turned to look at him, the smirk was back on Her lips as She reached down, gripping the hard piece of flesh between his legs. She pumped it a few times his throat filling with a desirous moan before She pulled her fingers away leaving it throbbing a few drops of pre-cum falling from its tip. "Get yourself cleaned off foot boy, we have a New Year's party to make an appearance at." She stepped out of the bathtub leaving him standing there his breathing heavy and still filled with the mixture of scents. he shuddered fighting the urge to take matters into his own hands, though he knew that would be unfair to his Mistress. he bathed himself as best he could by himself, and then stepped out of the shower, grabbing the towel that She had left for him and drying himself off. As he stepped back into the bedroom she smiled and pointed to the bed. A grey three-piece suit laid on Her bed next to Her own silver knee length dress, his dress socks and shoes waited next to the suit. Her boots sat on the floor on the bed a pair of full-footed tights and a pair of boot socks that would accent Her calves and would drive Her foot boy batty that evening. Her crotchless panties and a push up bra laid on the bed, next to which were a pair of deep red satin panties that he assumed were going to be on his body for the evening.

She chuckled a little as She saw the catch in his breathing as he looked over what was to be worn for the evening, and then reached down to grab Her bra, sliding it onto Her arms leaving the clasp undone at the front. Her eyes were locked on his as he watched Her hands slowly running over Her breasts teasing Her nipples to harden. Then She spoke once again, "Over here boy, clasp my bra for me." he moved over to Her his hands shaking once again and She could see that his reaction was exactly as She had wanted it. Her cock once again standing at attention, as his hands reached up to clasp the bra She leaned in and whispered in his ear, "Good boy" the cooing combined with her fingers lightly giving that hardness a few firm strokes as he stumbled to try and clasp the front clasp and snap it into place.

Her hot breath on his ear sent a bolt through him and then Her hand pulled away just in time, a dribble of precum fell off the tip of Her cock and spattered onto the floor next to Her boots. She looked down and then pointed to the floor. he was quick to drop to his knees knowing that She meant for him to lick up the mess that was just made. On his hands and knees he leaned forward and lapped at the single drop on the floor and then suddenly he felt pressure Her foot pressing down on his head holding him there. She leaned into the bed picking up Her dress and sliding it so that it cascaded down Her body, and then She pulled Her foot from the back of his head adjusting the dress and then sitting down onto the bed. "Now it is time for you to finish getting me ready foot boy," Her toes slid under his chin and She directed his face up so that he could see She was holding her panties out towards him.

he reached out grasping the wisp of fabric and lowered them so that She could slide Her foot into them, though as She did the foot lifted and pressed into his lips. A moan escaped as he leaned into the ball and toes, and She squeezed his nose playfully. Her cock continued to respond as it had all day and for the past week, leaping to full arousal before She slid her other leg through and pressed the ball of Her foot hard into his lips again garnering another kiss before he was allowed to lift the panties into place. As he did, he felt the heat radiating between Her legs and his fingers brushed softly over her shaven lips reminding him that these were crotchless, the dampness on his fingers now. She moaned above him and then reached down pulling the hand that had 'offended' away and She forced those fingers into his mouth. She smirked as She could see Her taste was once again eliciting the desired response and then released his hand.

"Tights now, foot boy," She held them out to him and watched as he bunched up the left foot's bottom and held it out for Her to slide Her toes into. As She slid those toes into the fabric She extended Her leg pointing Her toes and allowing him to start sliding the tight nylon up Her legs and then She heard the tell tale gasp, Her toes pressed a bit harder into his hardness and then pulled away long enough for Her to lift the right foot to repeat the process right down to the sharp intake of air from Her foot boy. As She settled both of Her feet onto the floor and stood up She reached down completing the task before handing him the light grey socks would pop between the black boots and black tights.

The grey cable knit socks felt weighty in his hand as he took it from Her and then he repeated the process of sliding them up Her legs, they rested just below Her knees and would provide just the look She was looking for and even from across the room would speak to Her desperate foot boy. She smirked once again as he finished pulling the second sock to Her knee and then ran the top of Her foot under his balls and let Her toes stroke once up the length of that hardened cock that She owned so completely.

Those lips still held a smirk as She looked down at Her boy and Her voice lilted as She ordered him to put Her boots on Her. his hands picked up the boot and undid the side zipper sliding them onto Her legs one at a time, zipping them up gently and tightening the straps. She grinned widely as he did so and noticed the lock and key charm that adorned the outside of each ankle. "Now a kiss and then it is time to get You all dressed up for the evening foot boy." A simple nod as he bent forward and pressed his lips to the leather, he could already feel it warming through from the heat that Her feet would emanate throughout the evening. Once he had kissed each of Her boots he leaned back and awaited Her order to prepare himself.

She smiled as She watched 'Her' cock throb twice before She ordered him to stand. he gasped as he did and his hardness stood out just in front of Her smirking lips. She breathed out hotly across the skin and then leaned forwards, Her tongue snaking between Her lips and then circling the head of the hardness hanging before Her. Her lips part and She took him into Her mouth all the way to the base of Her cock.

he moaned once again his voice quivering, as Her mouth took him he thought this was going to be it, he thought. She continued moving Her mouth, Her tongue, Her lips and then She pulled back with a pop Her mouth left him. he groaned deeply as Her cock bobbed wanting just a little more, and She smirked back up at him grabbing the red pair of panties and moving Her hands to the floor beckoning him to step in. Once he stepped in She pulled the panties up slowly and then as She neared Her property She leaned back in pressing Her lips to his sensitive aching balls. he moaned again just as She pulled the panties over the entire package and then patted the portion that was covered, She knew by the time that he finished getting dressed that it would subside just enough to be covered.

She stood then and leaned in kissing his lips deeply, pressing Her breasts into him and leaving him light headed. As She stepped away once more the smirk playing on Her face, "I am going to put my makeup on foot boy, finish getting ready and then go get the car." She left him a quivering mess and he reached for the undershirt to finish dressing. She hummed happily as She entered the bathroom once more, he was SO easy like this.

Chapter II: Getting Ready

he sat in the car waiting for Her to join him when his phone buzzed for the first time. It was a message from his Mistress as he opened the text there was a single word "Stroke" followed by a pic of Her extremely low angled as though he were looking up Her body he assumed from only a few moments ago. The smirk on Her lips omnipresent as he studied the image, he tapped out the reply 'yes Mistress' and then began to run his hands over the bulge that had already formed.

She laughed out loud in the bathroom as She saw the reply and then chewed on Her lower lip, tonight was going to be so fun for Her. So long as he was this obedient throughout the night, not to mention this malleable. She shivered a little from the power thrill of it all and began snapping some more photos. These would become useful throughout the night, She thought to Herself. Once She had finished with Her makeup and the photographic prep work She checked herself in the mirror and then made Her way to the car.

12