Office Boy Pt. 02

She smiled and picked up the butt plug considering Brian in front of her, now almost fully at her mercy. Of course, he could still run away, very awkwardly, she thought, smiling a bit to herself at the thought, toying with the butt plug in her hands. Though the state of his cock standing at attention told her that was not in Brian's thoughts.

"Bend over," Kelly commanded.

Brian slowly, and awkwardly, bent at the waist. His arms strapped up behind his head forced him to fight for balance. He was finally able to find some permanent stability with his head almost all the way down between his knees.

Kelly picked up the bottle of lube and moved behind him. Slapping him hard on the ass she commanded, "Legs straight!"

He did his best to comply, finding his balance once again. Kelly lightly caressed his ass then ran her hand up and down his taunt quads from behind. Finally, Brian felt a finger trail up from his balls to his tight rear hole where it stopped and circled applying just a bit of pressure.

"Mmmmm..." he moaned as is cocked twitched to Ms. Jones' touch.

"Oh, you like that, do you boy?" Kelly taunted, "Do you want me to push my finger into your ass and milk you until you cum again?" Still teasing his ass with her finger.

"Ohhhh...Yes miss, please."

Kelly pulled her hand away, "Oh there is much more to come for you boy, but first we have to get you prepared."

Brian's cock twitched again as he thought of what more could be coming. Meanwhile Kelly was applying a generous amount of lube to the butt plug out of his sight. He then felt the cold tip of the plug on his tight asshole as Kelly applied somewhat more than gentle pressure.

Reacting to the cold as well as the pressure Brian tried to pull away, his legs bending and lurching forward. Kelly caught him with her free hand on his ass. "Legs straight boy!! Don't make me add to the list of punishment," she commanded.

He straightened his legs again, "Yes, miss."

Kelly pressed harder against the resistance of his tight hole. "You seemed to like this yesterday, boy."

"I...aaaahhh...that was just your fing-aaaahhhh..." Brian gasped as the plug began to push into his ass.

"Just relax boy," Kelly soothed, pushing the plug and further widening his hole. She then reached around and gripped the head of his straining cock softly in her opposite hand. Circling the tip with her thumb she felt the pre-cum that had issued from it smoothing it around the head, she continued, "besides, it seems you are still enjoying this."

The plug started to break through his resistance and Brian could begin to feel it reach to those pleasurable spots inside of him, "Aaaaaahhh-mmmmmm...yes, miss, mmmmmm-aaaaaaahhhh..." he alternated between gasps and moans.

Still the plug pushed into him, up to its widest point. Brian's cock began to twitch, and pulse and he felt as if he was near cumming the pain and pleasure intermingling in his hole stretched, "Ooooohhhhh God!!" he screamed as the plug was pushed past its widest point and his asshole clenched back shut around its narrow base.

"Seems as though you almost came there, boy." Kelly prodded, her left hand still on Brian's cock, her right slightly tugging on the butt plugs base to ensure it was seated properly in his ass.

"Mmmmmm...yes miss." Brian moaned out, responded to the feelings as Kelly manipulated the plug in his ass.

Kelly pulled both hands away, and slapped his ass, "It's good that you didn't."

"Yes, miss." He responded.

"Stand up, boy," Kelly grabbed the collar between his wrists and helped Brian back upright. The plug felt different in his ass than his boss's finger. Now standing it seemed to press down directly on the pleasure zone around his prostrate. Brian moaned as he stood and tried to adjust to this new feeling. His cock still twitched and strained in front of him.

She moved back around in front of Brian and faced him. "Oh, I do love playing with your ass, boy."

"Yes, miss."

Kelly pulled herself up on her desk to a sitting position just on the edge. She ran one foot up the inside of Brian's thigh until his balls and cock rested on her instep. "I'm glad to see you seem to enjoy it as well." She teased, gently bouncing Brian's erect cock on her foot.

"Yes, miss," Brian moaned out.

Kelly leaned back on her desk as her other foot ran up the outside of Brian's thigh then around, she hooked his ass with her heel. She moved the foot from under his cock and around his other hip, hooking that side of Brian's ass as well.

As her legs spread, sitting on her desk, Kelly's skirt was pulled up around her waist. The wet gusset of her silk thong now exposed the scent of her heat wafted up to Brian's nose and he looked down between her legs. Kelly began to pull Brian closer to her with her feet as she further pulled her skirt up around her waist, exposing her soft but tight stomach above her panties.

Brian stumbled forward under the pull of Kelly's legs. She reached down and guided the head of his cock up, past the dampness of her underwear, the underside sliding across the smooth fabric under her hand.

"Mmmmmmm..." Kelly moaned, feeling his cock slide over her clit separated by just the thin fabric of her panties. She pulled Brian in tight with her feet. The head of his cock reached up past the waist band of her panties poked across her smooth stomach to near her navel. She leaned her head back and began to massage her breast with her other hand, through her professional top and bra.

Brian looked down at his boss, his cock pressed under her small hand against her silk clad mound. He moaned, almost in disappointment, as he realized that she was there for the taking but he was at her mercy with his hands still clasped behind his head.

For a moment, Kelly rubbed Brian's cock against her silk panties and clit beyond.

"Mmmmmm..." Brian now moaned his head tilting back. He embraced this feeling but imagined what it would feel like to press into his boss. His ass flexed forcing his hips into hers and reminding him of the newly inserted plug.

Kelly then stopped, released both her breast and Brian's cock and pushed him back with her feet. He stumbled away, his hips thrusting into air, his cock looking for stimulation. He opened his eyes and looked back down at Ms. Jones laying back on her desk just as she lifted her hips and pushed her panties down her thighs, then kicking them to the floor.

For a moment she just laid there, and Brian looked down at her. Kelly's pale bald mound was exposed and her moist lips below that. Her skirt pulled up past her waist, she ran on hand back down over her thigh and briefly swirled a finger around her clit before pushing it further down and inside of her.

"Oooohhh..." Brian moaned with desire at this action. He thought he was to be punished.

Kelly pushed her finger deep inside of her pussy and moaned, the palm of her hand pressing down on her clit. Again, she spread her legs around Brian's hips and began to pull him close with her heels. He stumbled forward again, unable to brace himself his arms restrained behind his head, as she still manipulated her own pussy with one hand. Kelly's other elbow propped herself up slightly and she watched as Brian wetted his lips with his tongue in anticipation.

As Brian neared, Kelly pulled her hand, now coated with her own heat from her pussy, and grabbed his cock. However, she did not guide it inside of her waiting pussy, she rubbed the head and underside of Brian's cock over her wet slit, then passed over her clit and up her now naked smooth mound. Kelly watched Brian's face as he again moaned feeling his cock between her hand and pale mound, his hips now pulled tight to her ass.

She caressed his cock on top of her mound and stomach. Her hand and his cock slick with her juices. Kelly made sure to keep a close gauge on his arousal. "Oooooohhh..." she moaned, "look how far your cock would push up inside of me."

Brian looked down and could see the tip of his cock almost reaching her naked slightly freckled navel, and moaned, "Yeeeesssss..."

Kelly continued to manipulate his cock. "You'd like to push it deep inside of my tight wet pussy, wouldn't you, boy."

"Ooooohhh, yeeessss, miss," he responded. Brian watched her stroke his cock against her mound and could feel her pussy's wet lips against his balls as Kelly's feet held him tight to her.

Kelly moaned as the base of Brian's cock rubbed against her clit, she began to slowly thrust her hips up towards him. Brian's moans got louder, as he looked down at her hips and hand slowly teasing his cock. His collar and wrist cuffs clanked as he unsuccessfully tried to bring his hands down from behind his head. He wanted to grab his boss by the ass and sink his cock deep inside of her.

Brian's ass clenched and his further pressed against Kelly's clit and pussy as she found the base of the plug in his ass with her heel and pressed hard against it.

"Mmmmmmmm..." Kelly moaned her pleasure building to the feelings of her young employee against her clit.

"Ohhhh...mmmmmm..." Brian responded, pleasure radiated up from the manipulations of Kelly's slick hand as well as the plug she manipulated with her heel in his ass.

Kelly could sense that he was close to cumming, she abruptly sat up straight, Brian's cock pressed between their bodies; her hand moved down to his balls, which she now squeezed and pulled down between his legs.

This sudden change and pain shocked Brian, he gasped, and he bent his knees to try and relieve the pressure. Had his arms not been restrained he likely would've reached down to protect himself, but they were clasped behind his head.

Kelly changed and now squeezed and pushed up on his balls, "Legs straight, boy."

"Yes, miss," Brian reacted, gasping for breath.

Finally, Kelly released his balls and pushed Brian back away from her, "Punishment, before pleasure, boy."

"Y-yes, miss," Brian responded, still catching his breath. His cock twitched in the air, one further drip of precum issuing from its tip, his orgasm denied at the last moment.

Kelly still sat on her desk, her legs slightly spread, naked pussy exposed below her skirt pushed up around her rib cage.

She again started stroking herself, "Though I can have pleasure, before I punish you, boy. On your knees."

Brian dropped instantly to his knees, with his hands still restrained behind his head he stumbled a bit. Now he was eye level with his boss's pussy. He watched, mouth slightly open near drooling as Kelly continued to push her finger slowly in and out of herself.

She sat up slightly and reached out taking his hair in one hand and placing her feet on his shoulders, "You know what to do, boy." Kelly said as she applied pressure with her feet on his shoulders pulling Brian into her.

"Yes, miss." Brian responded eagerly. He shuffled forward on his knees. Hands restrained, unable to slow himself as he stumbled forward; Kelly guided his mouth to her waiting pussy.

Brian took in a long, deep breath and smelled his boss's heat. He then extended his tongue and licked slowly up and deeply into her folds, tasting the acrid sweetness once again.

"Mmmmmmmmm...very good, boy," Kelly breathed out deeply as her young toy began to taste her pussy's depths, "just like a told you yesterday."

Brian's only response was to continue licking her fully with his tongue. His cock twitched and his desire only grew with his boss's approval of the efforts of his mouth on her pussy. Kelly laid her head back on her desk her back arched pushing her hips up into Brian. He let out a small moan as he saw her breasts heave with each breath.

Kelly again looked down to Brian, she breathed deeply and adjusted his head with her hand in his hair, toward her clit. Brian understood the direction and reapplied his tongue to her sensitive nub. Moaning Kelly's hips began to buck slowly to match the pace of Brian's tongue.

"Yes, boy, that's it." She encouraged, her climax growing close.

She reached down and unclipped one of Brian's hands from his collar. For a split-second Brian though of using his free hand on his cock, to feel the slickness that remained from Ms. Jones rubbing it across her wet pussy. He knew why she had freed it though and he moved around under his chin and slowly pushed his finger inside of her.

Brian moaned into Kelly's pussy and his finger pushed into her warm wet hole. He imagined that same feeling on his cock, then he curled his finger up and began to stroke the front wall of her pussy across her g-spot.

"Oooooooohhhh...yes, boy, very good." Kelly moaned her encouragement.

Brian responded slowly increasing his pace, his tongue matching his finger inside of her. His hips began to rock forward, his cock straining and searching for some relief as well.

Finally, Brian could see Kelly's stomach begin to clench and felt her legs start to tremor next to his head. She pulled his head tight to her pussy, holding it there with her legs and feet. Her hips bucked forward strongly into his face.

"Ooooooohhh...Yeesssssssssss..." she screamed out as she came hard, her juices pouring out of her onto Brian's cheeks and chin.

Brian continued to press with his tongue and his finger as the final tremors of orgasm flowed out of his boss. He smiled as she finally pushed him back and away. He fell back, his ass resting on his feet behind him still on his knees. The plug once again moving in his tight hole, reminding him of its intrusion.

One hand was still restrained behind his head, the other free, he slowly pulled his finger out of her pussy. Though his cock still twitched, begging, for some relief, Brian dutifully placed it back behind his head as well.

Kelly still leaned back, lying on her desk. Her legs still spread and feet resting on Brian's shoulders he watched her chest and stomach rise in deep breaths as she recovered. Her pussy leaked and the moisture ran down her ass towards the desktop.

She rose in front of her young employee, still on his knees before her, one hand clasped to the other behind his head. Kelly reached forward and reclipped his free hand to his collar. She stood now, still semi supported by her desk behind her, skirt bunched up around her narrow waist.

Kelly reached to Brian's chin, slick with her cum, pulled up so he could look at her. "Very good, boy."

Brian smiled heat rising in his chest at the thought of bringing pleasure to his boss, "thank you, miss." For a moment he was hopeful he had redeemed himself for his earlier mistakes.

Her hand then slid down from his chin, Kelly hooked her fingers under the tight leather collar around his throat. She pulled up, urging Brian to his feet. He stood up, feet wide, his rigid cock still standing at attention in front of him.

Still holding tight to his collar Kelly looked him in the eye, "Have to get you home now, provide a proper punishment for your transgressions."

Brian swallowed hard, the thought that he would not have to suffer any additional punishment fading at this comment and Kelly smirked at him. She then turned and bent over at the waist to pick up the wet panties she had kicked off earlier. Her skirt was still pulled up, Brian looked down and saw his boss's pale ass thrust up towards him, her pussy fully exposed, inches from his erect cock. If his hands were free his cock was willing him to reach down and pull those soft wet folds back around his aching member. His hands weren't free, so he only moaned softly and tried to urge Ms. Jones back with his thoughts, so that he could enter her.

Kelly, once again, knew exactly what she was doing and stepped to slightly widen her stance, teasing Brian further. From this position she gathered her used panties and Brian's clothes from the floor in front of the desk. As she stood; she placed the clothes on her desk, and the hard tip of Brian's cock brushed against the firm cheek of her ass.

Turning to face Brian once again, she reached back for a moment and felt the wet trail of precum that had been left on her ass. "Sorry, miss," Brian offered an unsolicited apology.

Kelly pushed her skirt back down finally, straightening it and her fitted button down top with a slight shimmy of her hips. She then took Brian's cock in her hand, noting how it was still slick from the moisture she had previously rubbed across it. "That's okay, boy," she finally responded, "I'm glad you are still so eager."

Brian moaned as Kelly gripped his cock. She only gently held it, he tried to start rocking his hips to force his cock in and out of her small hand. Kelly simply moved her hand to match his movements, not allowing any additional friction. For a moment though she again felt the member's weight and girth, her thumb barely meeting her fingers around its circumference.

Then she quickly removed her hand once again gripping Brian's balls and squeezing. "Oh no, boy. That will still wait," she menaced.

"Y-yes, miss." Brian gasped out. Kelly began to steadily increase the pressure on his balls. His knees buckled slightly at the pain, which only allowed Kelly to apply more pressure, holding him upright.

The pressure was ever increasing, and Brian gasped and looked down at his petite sexy boss with pleading eyes. Even if his hands were free, he would not dare try to protect himself, only taking one small step back which only amplified the pain in his balls as Kelly pulled and held him in position.

"Oh, boy," Kelly started in an almost apologetic explanatory tone, "Now that you have used your tongue and mouth to so thoroughly relax me... Excellent job, by the way."

"Th-thank y-you, miss." Brian stuttered out between irregular breaths.

"...I can now fully control my emotions," she continued, "and I can tell exactly how much pain I can cause you, without damage."

She squeezed tighter, looking right at Brian. Her steel blue eyes piercing into him. He looked back at her, gasping for breath and shifting on his feet trying to lessen the pain and pressure on his balls. A head shorter Kelly menaced up at Brian, breathing deeply her freckled pale breasts rising and falling deep and rhythmically.

Finally, she relented, releasing his balls. Brian sunk slightly, his knees bent and shoulders drooping. He briefly forgot about the restraints and tried to pull his arms down to attempt to rub some relief into his aching balls; but was stymied by the collar and cuffs.

Kelly noticed this slight movement, "It's okay, boy," Kelly comforted him, patting him lightly on the ass, "they aren't damaged."

Brian continued to attempt to catch his breath. Kelly smiled softly at him before turning away to move back around her desk. Though still recovering from this most recent assault, Brian's heart leapt at this small bit of kindness and approval from his boss.

Kelly gathered his clothes off her desk and placed them in her bag. She also picked up her panties, soiled from her heat as she had teased his cock earlier. Holding them up in front of Brian, Kelly said, "Well these are no longer good to wear."

Brian moaned between his gasps as he was reminded of scent of his boss's sex that still hung in the air of the office, augmented by her cum which still slowly dried on his face.

"Of course, you'll need something to wear as well so we can get you to the car," she continued walking over to her office closet, "I think I have just the thing in here."

Kelly opened the closet and retrieved a smart women's style khaki trench coat. As Brian watched she slung it around herself with a flourish and pulled it tight to her lithe body. The hem of the coat fell just a few inches below her skirt at her knees. Kelly twisted a few times in front of the mirror on the closet door, "It's going to be a little short for you, but I think you are skinny enough to make it work."

"I...uhh..." Brian tried to come up with a response, the coat would not provide him with much protection if he was to wear only that out of the office.