Office Boy Pt. 01

Brian moaned slightly and pressed his hips into her hand, but as he did her hand slid down to his balls squeezing simultaneously with the hand on his chin pressing into his cheeks as well. He gasped and sucked in air as her face hardened.

"Too bad there are still outstanding issues that need to be addressed, the erroneous report you sent out yesterday and touching me without permission," she nearly growled, increasing the pressure on Brian's balls with each word.

"Yes miss," he peeped, wheezing under the pressure.

"On your feet," she demanded.

He stood, practically lifted by Kelly's hand still pressuring his balls. Breathing hard he was beginning to sweat under the strain; until she mercifully released her grip. His groin was now level with Kelly's face and she noted Brian's still hard cock pushing a bulge in his underwear across his right thigh. She softened a bit thinking of what a great toy she now had under her control, and looked up and smiled again at Brian.

"It's your first day and you did so well with you initial training. I won't be so hard on you today." She smirked up at him, "Now, go and bend over my desk, boy, wait for me there."

Brian turned and practically sprinted the few steps over to his boss's desk. Immediately he reached for the opposite edge and bent at the waist putting his chest and cheek flat to the wooden top. Kelly smiled watching his response and rose from the chair then waited just out of Brian's view back over his shoulder.

He waited in this position unsure of what was to come. Finally he felt her step up behind him, her naked legs against the back of his thighs. Her hips pressed tight against his underwear clad ass, she then gripped his hips tight pulling him slightly back into her, so that his thighs no longer touched the desk. Umm...what is this, he thought.

"Oh, I like this," Kelly chuckled, and then demanded, "Legs straight." He instantly tried to lock his knees tighter.

"Feet apart," Brian widened his stance.

Now one hand left his hip and pushed down on the small of his back. He arched into the desk pushing his ass up and back further. Kelly now leaned down over him. He felt her nipples, then her breasts, push into his back. He moaned slightly.

"Oh, don't get too excited...wait right here..." she breathed into his ear.

"Yes miss."

Kelly went back towards the chair and considered the pile of clothes there for a moment, letting Brian wonder what was in store for as long as possible. She bent down and picked up her soiled underwear, considered them for a minute then decided she had a better use for them and left them off. She picked up and pulled her sleeveless dress back on and stepped back into her medium heeled shoes. She walked across the large office opening a closet and straightened the dress again in the mirror. Back to the chair she retrieved her used panties then circled wide so she was well in Brian's view as she walked back to where he was bent over her desk, swaying her hips a bit as she did.

Again, Brian was mostly naked and his boss fully clothed, but this did nothing to quell his unmet desires. Prior to this morning he had not given a second thought to his boss as a sexual person, now it completely clouded his mind. The dress only accentuated her supple well-formed body, narrow waist with wider hips, only aiding slightly in forming her breasts. Her dark hair and fabric of the dress contrasted with her pale skin. Brian licked his lips and tasting her heat there again, noticing how her cum was drying and slightly beginning to stretch the skin on his chin and face.

Kelly put the used panties on the desk in front of Brian, "I'll leave these here to remind you of your new role," she said.

"Now eyes front!" she demanded. Brian instantly turned his head up and faced forward. His chin rested on the desk next to the panties and Kelly's scent hit his nose with every inhale.

She now disappeared behind Brian, and he again felt her hands on his hips. This time, however, she hooked her fingers into the waistband of his underwear and quickly yanked them down to his knees, his cock bouncing free completely erect angling down toward the floor between his legs. Brian inhaled quickly at this movement, now fully exposed to his boss.

Kelly leaned back appraising him in this position before placing a hand on Brian's ass. "Hmmmmm..."she said as she caressed his cheek, "very nice."

"Thank you miss," Brian responded.

She then ran a finger down the cleft of his has applying a slight pressure to his tight rear entrance. Brian flinched slightly, "Don't move, boy, or there will be further punishment."

"Yes miss, sorry miss."

Her hand moved further down between his legs and across his tight sack, gently she cupped it in her hand. Brian moaned briefly at this tender manipulation but then braced for the coming squeeze. Kelly only continued to gently massage his balls. Then further her hand went finding and encircling Brian's rigid aching cock, fully able to assess it for the first time. Her thumb only barely reached the tips of her fingers as she closed her hand around it. She slowly stroked it from base to tip.

"Mmmmmm...aaaaahhhhh," Brian moaned inhaling and exhaling as her hand ran down his length.

"Oh you will do nicely," Kelly cooed stroking slowly back up the shaft to the base.

"Mmmmmm...aaaaaaaaahh," Brian again moaned, he was almost ready to cum at just this slight touch after all the events that had taken place this morning, his boss's musk strong in his nose from the panties lying in front of him, but suddenly Kelly's hand was gone.

"No, boy, we're here for your punishment!" Kelly chided him.

Kelly leaned over the desk her face next to his now. She reached down and began to lightly caress Brian's upturned ass. "Now, since I don't have proper tools here, I'm going to have to use my bare hand."

Brian now realized he was in this position to be spanked for his previous transgressions.

Still talking close into his ear, she took great delight in putting a slight menace in her voice, "You were a good boy, once you accepted your new role so I'll go easy on you today."

"Yes miss, thank you miss."

"I think 10 for the report and 10 for the touching without permission sounds fair. Don't you?" she asked.

"Yes miss, whatever you think miss."

"Good, now let's begin." Kelly stood.

Brian waited for the first blow, he wasn't sure what Kelly had meant by "proper tools," but he was thankful this would just be her hand. Besides, she wasn't that big how much could it hurt.

*WHHAAACCKK* Kelly was not new to this sort of thing and brought her hand down on Brian's ass twisting through her hips putting her entire weight into the blow.

"Yeeeeoowwww!!" Brian screamed.

Kelly smiled then bent to his ear again, "I'd be quiet if I were you. My office was built with thick walls, but you never know what your coworkers might hear."

"Yes, miss," Brian panted feeling the pain subside to warmth on his ass.

"Now, I'd hate to lose count so you count for me boy."

"Yes miss."

Standing again, Kelly hesitated, then again brought her hand down hard on her employee's bare ass.

*WHHAAACCCKK*

"Two miss." Brian counted.

Kelly looked briefly at the hand print raised on Brian's ass before bending again. "Are you sure? Two?"

"Yes miss, that was the second," Brian replied.

"Well I never heard you say 'one' so I'm not sure, we better start over." Kelly smiled sadistically.

"But I di..." Brian began to complain.

Kelly quickly grabbed Brian's face turning to towards her interrupting him she glared. "Did you have something to say?"

"Uh...only yes miss, better start over," he quickly corrected.

"Good," Kelly said releasing his face and standing again.

*WHHAAACCCKK*

"One miss!"

*WHHAACCKK*

"Two Miss!"

Kelly continued through ten swats to Brian's right cheek. She enjoyed watching the redness grow across his ass. For his part the pain was always there, but immediately after the impact desire began to grow in Brian's groin from this abuse. His cock, which had initial softened slightly under the punishment, was again as hard as he had ever been and Brian thought he could feel it stretching past its normal 8 ½".

"Good boy," Kelly complimented him, "That's ten for the report. Now only ten more for acting out of turn and we'll be done."

"Yes miss, thank you miss," the knowledge he was doing a good job even while being punished further excited Brian.

*WHHAAACCCKKK* Now on his left cheek.

"One miss!"

*WHHAAACCCKK*

"Two miss!"

Again Kelly cycled through 10 swats to Brian's ass reddening both cheeks.

"TEN MISS!" Brian shouted at the final swat.

"Good boy," Kelly again complimented him as she gently rubbed his warm ass.

Brian now nearly panted, a sheen of sweet on his back, "Thank you miss."

Kelly now slid her hand around Brian's hip to the front of his thigh, reaching between his legs she again found his stiff shaft and gripped it loosely. "Oh my, somebody is still eager aren't they?" she practically taunted Brian.

"Mmmmmm..." Brian moaned as she started to lightly stroke his cock, "Yes miss."

"You did well under instruction earlier and with your punishment. Do you think you deserve a reward?" Kelly asked.

"Aaaaaaahhhh..." Her stroking had sped slightly and her grip tightened somewhat, "...mmmmm...only if you think I deserve a reward miss."

"Good answer, boy."

Brian had been on the verge of cumming since he first put his mouth to his boss's pussy, but Kelly could see that in his breathing and feel it in his cock and applied just enough pressure and speed to keep him just on the edge, never letting him fully over the top.

"Mmmm...ohh," Brian moaned as Kelly removed her hand from his cock. "Miss..." he pled.

"Patience boy," Kelly assured him, "just want to make sure you know exactly what you're missing, since you have yet to earn the right to use my pussy."

Kelly's hand had move up, inside her dress, and she collected moisture from her pussy on her fingers, soaking them liberally.

"Aaaaaahhhh...mmmmmmm..." Brian moaned loudly as she resumed her efforts. His cock now slick with Kelly's cum. She stroked his hard shaft from base to tip, twisting and circling around the head.

Kelly now moaned slightly as she sunk a finger from her free hand into her pussy. Again she made sure her index finger was slick with her cum. She continued stroking Brian's cock, holding him just near orgasm with her left hand. Kelly put her right hand and newly lubricated finger on Brian's ass, she slowly ran her finger between he checks and applied slight pressure to his tight ring.

Brian flinched at this touch, his back arching up. He tried to move away from this threat of invasion. "Miss, I..."

"Do you want me to stop, boy?" Kelly interrupted him, stopping her actions on his hard shaft, gripping his cock near the tip she only lightly caressed the head with her thumb.

He moaned trying to move his cock through her hand with his hips while still avoiding her touch on his rear entrance. "N-No miss, I need to cum," Brian panted.

Kelly applied pressure to the small of his back, making him arch again in the proper manner, raising his ass. "Then behave and relax, you'll like this," Kelly reassured him.

"Yes miss," Brian complied, resuming his position and presenting his ass again to her.

She started to stroke him lightly, slowly, again along the length of his shaft but avoiding the sensitive head. Kelly again placed her slick finger at his tight entrance and began to apply pressure. Brian tensed slightly as the tip started to stretch his ring pushing inside of him.

"Arrg...ahh," he reacted, burying his face into his arm and shoulder.

"Easy boy," Kelly soothed. She gripped his cock slightly tighter, and her finger started to penetrate Brian. She pushed her finger into him, up to the first knuckle. "Good boy."

He squirmed slightly but stayed in position, this praise from Kelly added to his pleasure. "Thank you miss...arrrg..." Brian panted as she continued to push into him.

Kelly still lazily stroked Brian's cock as she focused on loosening his ass. She twisted her hand as she pushed further, moving her remaining fingers out of the way and entering him as deep as possible. Kelly held her finger inside of Brian allowing him to adjust to this invader into his virgin hole.

"How did that feel?" Kelly asked, now refocusing on stroking Brian's cock.

"Ungh...it hurt a bit..." Brian moaned out.

"It'll start to feel better soon."

She now started moving her finger slightly in and out of Brian's ass, always leaving more than one knuckle inside of him, matching the rhythm of her hand on his hard shaft. Kelly could feel his tight ring clench from time to time around her finger but his moans now started to sound more full of pleasure than pain.

"Are you starting to like it boy?" she asked.

"Unghaaaahhhh...mmmmm...yes miss," he groaned out.

Kelly could feel his cock responding not only to her manipulation of his shaft but also to the feeling in his ass. She started bending her finger slightly inside of him pushing pressure down on his prostrate. Brian's head now moved back facing forward, bringing the scent of her used thong back to him. He still gripped the desk tightly.

"Oooohhh...yes miss..." he yelled.

She slowly increased the rhythm both in Brian's ass and on his cock. As he continued to moan his approval of her efforts, Kelly could see the muscles of his ass and his legs begin to tense.

"When was the last time you came?" she asked, further tightening her grip on his cock as she stroked it.

"OOOoooohh...Friday night...I think miss," he panted out.

"Four days, my you have great self-control for such a young man. Well, this is going to be quite the mess then," she chuckled.

Almost immediately Kelly sensed his balls tightening as Brian's ass gripped her finger inside of him. She pushed her finger deep pressing hard down onto his prostrate simultaneously stroking his cock as hard as she could.

"Aaaahhhh...Yesssss..." Brian yelled out, his hips bucked forward, his legs, stomach, and ass spasming as he came harder than he could remember. Cum issued from his cock in thick ropes spurting strongly onto the floor just in front of his feet. A wave of pleasure grew from his groin and washed through him and Kelly slowed the rubbing of his cock.

Even she was somewhat amazed at the strength of spray and quantity of cum that Brian had released. As Kelly slowed her strokes Brian relaxed in post orgasm pleasure on the desk. She restarted the curling thrusts of her finger in his ass, now just holding on to the base of his cock and balls with the other hand.

As Brian began to recover from his orgasm he was surprised how stiff his cock still felt. Usually he deflated quickly, he thought. He started to lowly moan again as the finger in his tight hole resumed its pace.

Not long after his core again contracted and Kelly felt his cock erupt again through her hand, "Ooohhhh...god...I'm cumming again!!" Brian shouted in surprise.

His cock softened slightly in Kelly's hand but she continued to probe his ass. "Come on, be a good boy, let me see how much you have in you."

"Oh god, oh god, aaaaaaahhhh," he came for a third and final time, the last remnants of his seed spraying onto the floor.

Kelly released his now limp cock and gently massaged his balls, her finger still in his ass, "Is that all you have for me boy?"

"Mmmmm...I think so miss," Brian replied now fully supporting himself on his boss's desk as his legs started to go limp from the exertions of his multiple orgasms.

He inhaled a gasp as Kelly finally pulled her finger from his ass, feeling the emptiness there he sunk to his knees then crumpled over next to her desk and the large puddle of cum that he had created there. Kelly crouched near him and picked up his head with a hand on his chin. He started to recover slightly and again noticed his shapely boss.

Kelly reached down and scooped up some cum from the pool on the floor with her finger. "Have you ever tasted your cum boy?" she asked, holding the glob up in front of his face.

"No miss."

She moved her hand and finger toward his mouth. Too spent to raise much of a protest, he could still feel the sting on his cheeks from his previous punishment, Brian briefly considered whether that was the finger that had been so recently in his ass, but opened his mouth taking the finger between his lips.

"Make sure it comes out clean," Kelly smiled at him. He sucked on the finger tasting his warm salty issuance for the first time. Not so bad, he thought and noting the way she looked proudly down at him he swirled his tongue around Kelly's finger to make sure he cleaned it fully.

"You did well this morning boy. I think you'll handle these new work duties well." Kelly said removing her finger and gently holding his face in her hand.

Brian smiled pleasure growing in him thanks to this approval from his boss. "Thank you miss, I'll do my best."

Kelly stood and walked across the office to the small kitchenette to wash her hands. Brian watched as her ass swayed in her fitted dress he thought of how much he wanted to please her and gain further access to her body. Then he assessed his situation, he sat slumped next to what must've been the largest pool of cum he had ever seen. His underwear was still around his knees, the cheeks of his ass still warm, and he had a slightly empty feeling from where Kelly's finger had stretched his previously virgin hole.

"You still have a report to fix boy, you'd better clean up your mess and get back to work." Kelly called to him from across the office.

He quickly looked around for some sort of Kleenex or paper towel, and then realized what she had meant. "Yes miss," he said. Then Brian got to his knees and leaning forward began to lick and suck up the pool of cum on the floor.

Kelly looked over her shoulder as she finished washing her hands and saw her new toy's ass high in the air again. He tentatively at first then more and more hungrily cleaned up his own cum from the floor with his tongue and mouth. She felt her chest flush and nipples harden slightly again as she thought of further plans for her employee. He will make a good toy, she thought.