Office Boy Pt. 01

She now moved her hand down, massaging his balls softly, "If you take matters into your own hands," she chuckled at her pun, "You will be punished!"

Brian's eyes popped wide and he yelped silently gasping for breath as Kelly squeezed his balls tightly. For an instant his hands moved from behind his back to fight off this "attack," but Kelly's glare and a slight shake of her head dissuaded him. Still his chin was supported but he instinctively wanted to slouch further in an attempt to protect his sensitive areas. Kelly held strong keeping his back mainly erect her eyes locked onto his. "Yes, miss," he squeaked out hoping his immediate response would ease her grip.

Kelly continued the pressure, "If punishment doesn't work, I'll find other ways to prevent your disobedience."

She finally released both hands the lower sliding up and once again briefly rubbing Brian's stiff cock, "good, I see a little pain doesn't weaken your...enthusiasm."

As Kelly stood, Brian crumpled slightly at her feet and gasped for breath, briefly moving a hand toward his aching balls then stopping himself remembering Kelly's previous slap to his arm and her latest edict. "No miss," he finally responded.

Kelly noticed him resisting his urge to self-comfort, "Good boy."

Brian smiled at her acknowledgement. She had noticed his restraint and he had pleased her.

Kelly could see in his eyes, Brian exalted in even this slight praise, he truly was willing to do whatever necessary to please her now. Her own breath deepened at the thought of how she would use her new "office boy." She stood looking down at him and realized her own desire had grown along with her young employee's cock. Kelly squeezed her legs together as she stood for just a second assessing the wetness that had pooled in her thin small panties.

She turned bending at the waist with her legs slightly spread, making a show of adjusting the position of the chair with her ass pushed up and out mere inches from Brian's face. She heard Brian moan with desire as he was able to fully take in her firm shapely ass and legs in her well fitted dress, her scent drifting into his nose once more.

Kelly looked back over her shoulder seductively at Brian. "You know you've caused me significant stress with your mistakes. Do you think you could help me with that?" Kelly said further arching her back.

"Oh yes miss," Brian said, starting to stand.

He reached forward lightly placing his hands on his bosses hips as she stood bent over. Brian looked down to her ass and hips and up to her narrow waist envisioning sinking his aching cock deep into her pussy. At the instant his hands made contact with her hips Kelly snapped upright spinning around.

She slapped him hard across the face. "I didn't tell you to stand!! And I DEFINITELY did NOT give you permission to touch me!!" Kelly yelled, fire in her eyes.

"Sss-sorry miss," Brian reeled from the slap.

"Back to your knees!!"

He dropped quickly hands once again behind his back, head down sheepishly. Kelly bent towards him now. He looked furtively to her breast hanging close in front of his face in her dress then quickly down again. She reached down once again gripping his balls, slowly adding pressure until she saw him begin to wince.

"You'll be punished for that as well," she said before releasing her grip and standing over him once again. "But first...you'll address the stress you have caused me this morning."

Kelly was confident in her sexuality and her body, which she kept well-toned with a strict regime of running and yoga. She reached behind her back and unzipped her dress. Slowly she pulled her arms free then let it slide off her breasts, pushing it down past her hips making sure her small thong stayed in place and let it drop to the floor.

Brian had been sheepishly staring at Ms. Jones feet. Embarrassed by how he had further disappointed his boss. He did not realize what she had been doing as she stood in front of him until the dress hit the ground and she slowly stepped out of it kicking it aside. He slowly started to look up, following her well-shaped calves to her soft toned thighs. Brian longed to reach out and run his hands up with his eyes but now knew better to touch without being asked.

Kelly allowed him to slowly look up towards her taking in her body as he did. She noticed Brian's gaze stop for a moment as it reached the area between her legs, now covered only in a small black simple cotton thong that hung low on her hips; her pussy wetting the fabric of her underwear mere inches from Brian's nose. Kelly saw his chest rise as he inhaled deeply before continuing.

Somehow it seemed Brian's cock got even harder as he took in his boss's scent and his gaze moved up across her flat stomach till finally looking into her eyes past the underside of Kelly's frim c-cup breasts which stood proud and taunt from her chest capped by erect nipples.

Kelly bent slightly taking Brian's chin in her hand roughly; again holding his head back and looking up at her, "Do you want to touch me now?"

"Oh god, yes miss," Brian blurted out, "my cock is aching, please let me satisfy you."

"No, I'm not sure you're ready for all that," Kelly responded, "We'll see how you do and maybe, eventually, I'll use your cock for my pleasure."

Embarrassed by his own forwardness Brian said, "Yes miss, sorry miss, please tell me how I can please you."

"Very good, boy," Kelly said as she stepped back and sat down in the plush office chair. She slid her ass forward to the edge of the seat and leaned back slightly. Her legs were spread slightly and Brian could clearly see the damp gusset of her small thong.

She ran her hand up her stomach slowly and gently caressed her breast and lightly tugged at the nipple. Brian's eyes were rapt on her actions his mouth slightly open in amazement as he knelt in front of her. "Would you like to massage my breasts and play with my nipples?" she breathed out in a slight moan, teasingly.

"Oh yes, miss, please." Brian begged.

Kelly then moved her hand, again slowly, down back across her stomach before gradually, inch by inch sliding it into her panties. Brian's breath shortened as he watched. Her fingers hidden by her underwear pulled some moisture from just inside her wet lips then she began to circle and rub her stiffening clit.

"Mmmmmm..." she moaned as she began to give herself pleasure, "Maybe then you'd like to push a finger into my tight, wet, pussy."

Brian was still stunned as he watched from his knees, cock straining in his own tight underwear as his boss began to clearly masturbate in front of him. He thought he could nearly cum just watching her. She looked down at him massaging her naked breast with her free hand. "Yes, miss, please let me help pleasure you."

Kelly sat up slightly, still absentmindedly massaging her clit and stroking the wet lips of her pussy inside of her panties. "Have you ever given a woman oral pleasure, boy?" she asked.

Brian blinked and shook his head slightly. He was a bit shocked by the matter of fact nature of this question. He was able to pull his eyes up from his boss's hand stroking herself in her underwear to look to her face to respond, "Uh...I...yes, miss."

"You don't sound too confident in your answer," she pressed.

"Yes miss, I've gone down on a woman before."

Kelly again leaned back, kicking off a shoe. She extended her leg out and rested her foot gently on Brian's shoulder. "And did you make her cum?"

Brian turned slightly resting his cheek a bit on Kelly's smooth calf, "I...uh...I mean, yes miss, I think so."

Still Kelly manipulated the outer edges of her pussy and clit further wetting her panties and felt the moisture drain down her ass as well. She pushed Brian's face back to face her fully with her foot before returning it to his shoulder.

"Are you sure, boy?"

"I mean, she seemed to, she said I did a good job," he replied.

"Keep your hands where they are," Kelly demanded referencing their position behind his back. She wrapped her foot around the back of Brian's slowly pulling him closer to her.

"You'll know if you make me cum," she continued.

Brian stumbled forward leaning and trying to move on his knees under the pull of Kelly's leg. "Yes, miss."

He was just about to fall face first into Kelly's crotch under the tug of her foot when she relented letting her leg fall over his shoulder, her calf resting on his back, his shoulder near her knee under her thigh. She quickly removed her hand from her underwear and grabbed Brian's head by his short blond hair. Holding him there for just a moment, "and you'll know if you don't as well."

Brian looked up, past her wet underwear just inches from his face, and the pale breasts he longed to rub and suck, to Kelly's face, "yes, miss."

Kelly applied a slight pressure to his back with the leg she had draped over him and Brian fell forward. Guided by her hand in his hair his mouth buried itself into the sodden gusset of her panties his nose resting on the top of her mound. He inhaled, deeply taking in her scent, almost tasting her with his nose. The pungent smell only further excited him and her control only furthered his desire to please her.

"It's okay, boy, you can taste me." Kelly said.

Brian opened his mouth and tasted her sex through the thin cotton of her underwear. He sucked at the thin material taking in as much of her sweet acidic flavor as he could; then pushed his tongue hard trying to apply some pressure to her clit.

"Do you like the taste, boy?" she asked releasing some pressure from Brian's back.

He paused for a moment saying, "Oh yes, miss, very much," briefly before again trying to push through the material of her underwear into her pussy with his mouth.

Kelly now brought her foot back up to his shoulder and pushed him back up away for her. Brian resisted initially trying to twist free and maintain his position at her sex before relenting as she added her other foot to his opposite shoulder. He moaned slightly plaintively as he sat back onto his feet, still kneeling.

"You are an eager little boy, aren't you?" she asked rhetorically, Brian nodding slightly his desire to please his boss and atone for his previous mistakes, as well as his young hormones aching to feel more of this woman urging him on.

Hooking her thumbs into the narrow waist bands of her thong, Kelly lifted her ass off the chair and slowly began to push the underwear down off her hips. "Do you think you can make me cum?" she asked.

Eyes fixed as Kelly pulled the panties slowly towards him, hoping for his first view of the core object of his desire, Brian replied, "I'll try miss."

Kelly pushed her underwear up her thighs to her bent knees and dropped her ass back to the edge of the chair. Still her pussy hidden from Brian's view as her thighs were pushed together, her calves and feet spread to Brian's shoulders. He look down between her calves under the panties now at her knees above his head but could only see a view of the lower cheeks of her ass as they were pressed up by the cushion of the chair.

"Try? You better DO," Kelly demanded, "or more punishment is instore for you."

She now pushed the small thong up over and past her knees; releasing them they slid down to her ankles and hung loosely in front of Brian's face.

"Yes, miss, please miss, I can do it." Brian begged, the scent from her pussy now again deep in his nose from her wet panties that hung in front of him.

Kelly lifted her feet from his shoulders and Brian leaned forward slightly as she again placed her calves there, lassoing his head with her panties. She spread her legs as she applied pressure to his shoulder blades with her heels drawing him into her again. Brian got his first view of her bare shaved pussy, lips glistening with moisture.

He moaned as he eagerly leaned forward under the pressure of her legs on his back. Once again she caught him by his hair with one hand tilting his head back to look up at her. Kelly rubbed her breast and massaged her nipple with her opposite hand, "Don't worry, follow my instructions and you'll do fine," she said.

"Yes, Mi-smmsmm," his response muffled as she pulled his face into her eager pussy.

Kelly lifted her hips into him arching her back and moaning as he hungrily sunk his tongue into her folds. She kicked her soiled underwear aside and put both feet up on his shoulders pushing back against his mouth urging him deeper into her.

Brian eagerly dove into his task, trying to lick, suck, and kiss every inch of her pussy all at once, like an over eager dog too excited to please his master. Kelly's juices smearing over his face.

Pulling his hair tight in her hand to get his attention Kelly said, "Easy boy."

Brian slowed his assault on her pussy, looking up for guidance eyes begging, his nose just above Kelly's bald mound.

"Now focus on one thing first and do it properly," she instructed, "I want your tongue deep inside of me, lick deep and slowly up through my lips into my pussy."

Brian refocused, moved his chin down low burying his nose into Kelly's mound. He slowly extended his tongue parting her lips extending deep inside her then slowly through exiting and pressing past her clit. He looked up for her reaction as he did. Kelly's head leaned back and she moaned deeply.

He was pleased with himself to get this reaction and slowly began to repeat this action; a warm feeling spreading up from his own cock in response to her pleasure. Kelly held his head but loosened her grip on his hair. Brian watched, as he licked repeatedly deep inside of her, as Kelly rubbed her breast and began to push her hips to meet his manipulations, continuing to moan in rhythm with his efforts.

"Very good boy," Kelly breathed out recovering slightly. "Now find my clit with your tongue."

Brian adjusted moving up he pressed through her lips, sliding his stiff tongue slowly up until Kelly squeezed her thighs around his head, with a gasping moan. His tongue now began to manipulate her eager nub.

"Aaaahhh...yessss...good, you've found it." Kelly gasped. "Now suck and lick it, slowly at first."

He smiled slightly watching Kelly's reactions to his efforts. He had thought that his sloppy assaults on his previous partners had been good enough, but with instruction from a woman who was confident in what she needed Brian now had a chance to really bring her pleasure. He held her clit in his lips and slowly licked it, circling then sucking.

"Oooh, yes, boy...aaaahhh...you are a quick learner." Kelly breathed out, her legs beginning to shake slightly relaxing over Brian's shoulders.

Brian slowly built up the speed of his efforts on her clit and began to learn to gage how he was doing from the sound of her breathing and movement of her hips. Kelly's pussy responded, moisture flowing down his chin.

Kelly rocked her hips into his mouth, gently directing his head with her hand or her thighs as necessary when Brian lost track of her clit with his mouth. Alternating between closing her eyes head back and watching as her young employee worked to bring her to orgasm.

"Aaaaahh...you're doing good boy, put a finger inside me," she directed.

He moved a hand from behind his back and moved it below his chin. Slowly he traced up from her ass collecting her moisture on his index finger then pressing into her tight wet pussy.

"Mmmrrrrmmm..." Brian moaned onto her clit as his finger pressed in, he imagined the feeling that would have on his cock and almost came in his underwear without ever being touched.

Brian began to work his finger in and out of her building up speed quickly. Again he felt Kelly quickly grab tight pulling his hair, "No, not like that," still nearly breathless thanks to his tongue working her clit, "curl your finger up and out, pressing on the front wall of my pussy."

He adjusted his efforts and Kelly moaned deep as his finger matched his tongues efforts on her clit on her sensitive inner g-spot.

"Ooooooohhh...yesssssss..." she moaned long as his efforts match her instruction. She could feel her orgasm beginning to slowly build. "Keep doing it juussst liiikkke thaaaat."

Brian continued, building speed and pressing harder with his tongue and finger to match the rhythm of Kelly's bucking hips. As her pleasure grew Kelly now gripped his head with both hands, holding him exactly where she wanted him.

His desire to please his boss grew and he moaned into her as he could sense her climax nearing. He breathed in deeply enjoying her musk. Brian knew his cock was rock hard with desire but that moved to the far reaches of his mind and he focused solely on bringing his boss pleasure a warmness in his chest building with her orgasm.

Finally Brian saw Kelly's sexy flat stomach clench, her head lift and look down to him for a moment before she pulled his mouth tight to her clit grinding her hips into his chin.

"Oooooohhh...I'm cummmminnng!!" she screamed, throwing her head back. Her abdomen clenched and released repeatedly and Brian could feel her thighs shaking next to his head, and the walls of her pussy clenching on his finger inside of her. She gasped and moaned, as her cum flowed out of her and down Brian's chin.

"Eeeaassy, slow down," she finally panted out.

Brian slowed in his efforts, smiling at the reaction he had drawn out of his boss, enjoying her continuing spasms as he relented in his efforts until with one last shudder she released him. He pulled his head up, mouth away from her clit and removed his finger from her pussy. She pushed him back with her feet then relaxed deeply into the chair, feet now on the floor between them but legs still spread in front of Brian.

He returned to his upright kneeling position and instinctively put his hands behind his back. Once again he was aware of his aching erect cock in his tight boxer briefs. Brian watched as Kelly slowly recovered from her orgasm, her breasts heaved, and her pussy, clit, lips and inner thighs glistened with her cum. He could feel it also thick on his face and chin.

Kelly finally looked up in her slouched position in the chair; then sat up straight. She smiled down at Brian. This small gesture of approval exciting him further his heart quickened hoping for licit approval of his actions. "That was good boy, I'm glad to learn you can take instruction," she praised.

"Thank you miss," Brian beamed back at her.

"Has a woman ever reacted to you like that before?" she questioned.

Thrown slightly Brian stuttered a response, "Nnn...uh...I...aaahh...No miss I don't think so."

"Do you still think you made them cum?" Kelly continued.

Brian thought to the times he sat there proudly after going down on his early girlfriends, beaming as he had just done, then embarrassed to realize their probable disappointment, he looked down to Ms. Jones feet in front of him, "No miss...I...uh...I guess not," he responded glumly.

Kelly then sat properly in the chair, at the edge of the cushion, knees legs tight together as if in a smart skirt, back straight, as, perhaps, a proper teacher. She reached out and lifted Brian's head by his chin tilting it upward to face her. He looked at his naked teacher, pussy now hidden between her legs but soft bald mound still exposed, her firm breasts that he longed to feel and pale neck slightly flush still from her orgasm, and up onto her softening face.

"It's okay, you seem to be a quick learner," she reassured him. "You did well today."

He smiled at her approval, his confidence growing again. Kelly leaned in holding his face looking at hers. Brian didn't notice her reaching down but then felt her other hand grip and begin to stroke his rigid cock through his underwear. "I'd even say; you might deserve a reward."