Office Boy Pt. 02

Kelly walked back over to Brian, she reached up to the buckles holding his wrists to his collar. For a moment she paused, "You're going to behave now, right, boy?" she asked.

"Yes, miss, of course, miss," Brian responded quickly, his desire to please his boss over riding any potential embarrassment at his situation.

"You better," Kelly replied, one hand briefly caressing his balls. Brian took a sharp breath at this touch but remain still while she then began to unfasten his wrists from his collar. She held his hands in place behind his head. "Now, help me out of my coat," she turned her back to him and held the coat open waiting for Brian to take it from her shoulders.

"Yes, miss," Brian reached out and carefully removed the coat sliding it off Ms. Jones shoulders and carefully down under her loose almost black pony tail.

Kelly moved back to her desk and gathered some additional items into her bag, sure not to forget the bottle of lube. She looked up, Brian was awkwardly standing holding the coat eyeing its potential to cover his nakedness. "Well, put it on, boy. There is still much to do tonight," She instructed.

"Yes, miss," Brian slung the coat around and slid his arms into it. He was able to pull it easily around him and he started buttoning it up. The lowest button was only as low as his navel and the hem only extended down just to his upper thigh. The highest button was at the middle of his chest and the coat did nothing to cover the collar around Brian's neck. The arms short, like the young employee had just gone through a growth spurt, left his wrist cuffs exposed as well.

His cock, while still erect, had deflated slightly but it still poked at the lower edges of the coat closure threatening to be exposed Nervously Brian looked over to his boss, "Miss, I don't know if this will work."

Kelly crossed over to him quickly, smiling, she grabbed the belt of the coat and pulled it tight around his stomach, cinching it tight. She stepped back and looked, "Nonsense," she said, "I think you look great."

"Um...okay, miss." Brian wavered.

She stepped in close and her hands moved around to his barely covered ass. They easily pushed up the coats tails and she grabbed his bare cheeks pulling Brian close. "It's like a sexy little mini skirt." Kelly teased.

Brian enjoyed the playful squeeze of his ass under the coat and could feel Ms. Jones firm breast pushing into his chest. "Yes, miss," he responded.

Kelly now slid one hand down in between the two of them. It pushed into the front of the coat and she started to gently stroke Brian's cock, it instantly responded nearing full hardness again. Her other hand still on his ass moved toward his crack and her fingers found the plug still firmly nested in his ass, and she manipulated it to press harder up into his tight hole. "I need to have easy access to you, boy." She cooed up at him.

"Yes, miss, mmmmm..." Brian moaned out.

Kelly released him and stepped back to grab her bag. Then started heading for the door of the office. At the door she stopped and turned, Brian still in place his fully hard cock is now clearly pushing through the gap in the front of the, coat exposed. "Come on, boy, let's go," Kelly demands.

Brian pushed his hands into the pockets of the coat pulling the front together; and hunched forward trying to protect his cock from exposure as he walked. It seems to work; but had the effect of exposing the lower part of his ass to view from behind. Could anybody also see the base of the plug that resides there now as well, he thought. "Yes, miss," he replied as he joined her at the door.

Kelly grinned up at Brian, turning and moving out the door to her office she thrust her arm through his hooking at the elbow. She proudly strode into the outer office tugging Brian along by his arm. He nervously looked around to see if any coworkers remained who would see him exposed in this way. Quickly he determined they would make it safely to the elevator he took comfort in Kelly's arm holding him almost as a true girlfriend might.

Brian once again tensed as the elevator neared their floor. "There could be anybody inside" he thought. Kelly sensed his anxiety and chuckled slightly. Brian swallowed hard and pulled the short coat tighter in front of his barely covered cock as the doors opened. Strangely, to his thoughts, it seemed that his cock had grown harder at the possibility of this new humiliation.

Mercifully the elevator was empty as the doors opened and Brian sighed in relief, as Kelly quickly stepped into the car and pulled him along with her. She pressed the button for the underground parking level and stepped back, close to Brian.

As the doors closed, she pushed her hand through the loose flaps of the jacket and grasped Brian's hard shaft. "Would you be embarrassed, being exposed like this?" she asked teasingly as she gently began to stroke Brian's cock.

"Y-yes, miss." Brian moaned a response. His cock once again reached its full length and hardness with her manipulations.

"That's too bad," she cooed, beginning to grip his cock and stroke a bit harder as the elevator began its descent.

Brian moaned loudly now, his cock desperate for relief, he began to thrust his hips in time with Kelly's strokes.

As the elevator dinged past the first floor as they descended Kelly stopped the teasing of his cock and demanded, "Hands out, behind your back!"

Brian complied instantly, his fully erect cock now pushed through the gap in the short coat leaving him nearly fully exposed. He tried to lean forward and slump his shoulders to coax the jacket to fully protect his nakedness. All to no avail.

Finally, Kelly again snaked her arm through his and leaned into him. Brian could smell her scent and licked his lips, once again tasting her heat that dried on his face. "Stand up straight, boy," she whispered gently up to him, "I want you to be proud of your position in my firm."

Brian slowly stood tall, this reassurance from his boss giving him new confidence, "y-yes, miss." He still hesitantly responded. He let out a sigh of relief as each floor passed without the elevator stopping for more passengers.

At last the car stopped at the lowest floor. Brian once again slunk forward as he anticipated the doors opening to the parking garage and potentially exposing him. Kelly pulled back on his elbow, "Boy..." she warned.

Brian again stood straight. Mercifully the elevator lobby was vacant. Kelly pulled him out of the elevator and began walking across the half empty garage toward her car. She looked down and smiled as his cock still bobbed proudly in front of him.

For a moment on the elevator ride Brian felt as though he may relax, and his cock could soften a bit retreating to the protection of the coat tails. However, now, as he had to walk quickly to keep up with his boss he was reminded of the plug in his ass and it shifted slightly with each step, rubbing against the sensitive areas inside of him. His cock remained at full stretch, exposing itself for the walk to Kelly's sleek black luxury coupe.

She directed him to the passenger side of the car. "Stay here," she commanded.

Kelly pulled her arm out from Brian's elbow and move to the opposite side of the car. She took her time locating the keys to the car as he stood opposite her still barely covered by the ill-fitting coat. She noted how he began to look around the garage.

After, what Brian felt was an interminable delay, Kelly finally opened her car door and got in the driver's seat. He still waited for the door lock to click open on his side. "Were those footsteps..." he thought, more nervously looking around, "...had the elevator just dinged its return."

Kelly smiled as she watched him from inside the car for just a moment longer. Visibly nervous he had not moved his hands from behind his back as she had instructed. Finally, she reached over and pushed the passenger door open wide.

Brian instantly made a move to get to the safety of the car. "Not yet, boy." Kelly instructed.

He had been taking one last look over his shoulder before his assumed move to safety. On Kelly's command he stopped instantly, turning to investigate the car. As she had twisted and bent to lean across to the passenger side, her top now hung loosely exposing almost the entirety of one of her breasts to Brian's view. "Miss..." he questioned, wetting his lips at thoughts of Kelly's pale freckled skin and soft toned body.

"I don't want you wrinkling my coat, take it off." She instructed.

Brian stood up straight again and looked around nervously.

"Boy, should I add your hesitation to my list of infractions?"

"No, Miss," he quickly responded, unbelted and unbuttoned the coat removing it.

"Good, now lay it nicely on the back seat," she said, pushing the front passenger seat forward; Brian looked into the back seat and saw one more much larger wide leather buckled strap, "and take that belt and put it on."

"Yes, miss." He complied quickly now fully exposed in the semi-public parking garage. Leaning into the back seat of the car his ass and the base of the plug were fully exposed to anybody who may be behind him for a moment. Brian placed the coat across the back seat, careful not to create any wrinkles then stood taking the belt.

He once again took a quick look around him as he stood naked, only protected by his collar, wrist and ankle cuffs. "Was that the ding of the elevator," he thought. Quickly he fastened the belt around his waist.

Kelly pushed the passenger seat back then watched as her toy stood naked in front of her fastening his new belt. "Make sure it's nice and tight."

"Yes, Miss." Brian responded, clasping the buckle.

He breathed a deep sigh of relief as Ms. Jones finally allowed him to get in the car. He quickly complied and pulled the door shut as he sat down. He moaned slightly as the seat pushed the plug deeper into his ass, then quickly moved to cover his still erect cock with his hands.

Kelly quickly slapped the back of his hands, and he pulled them back. "Oh no, boy, what have I told you about touching yourself?"

"Miss, I wasn't -," he was quickly cut off as Kelly roughly grabbed his chin.

"Are you talking back to me."

Kelly reached across and leaned into Brian's arm, her breasts pushing tight against him, she took his wrists one at a time and clipped them to the belt near his hips. For a quick instant he had thought he would be able to cover his nakedness for the ride. Now he pulled on the cuffs trying to reach his exposed cock but quickly realized that it was a futile effort.

Kelly moved her hands to his thighs then slowly pushed one down between his legs. Brian opened his knees slightly allowing her easier access. Her hand glided past his balls and one finger reached down and found the base of the plug in his ass. She pushed and manipulated the plug toward his prostate.

"Mmmmm..." Brian moaned as he felt the plug push into his ass. He lifted his ass to allow Kelly easier access and his cock twitched aching for relief. She made one quick stroke up and down his cock with her other hand, then sat back into the driver's seat; leaving Brian with only a devious smile and her lingering scent.

Brian slouched in the passenger seat for the drive to his boss's house. The windows of the luxury coupe were slightly tinted but anybody who was trying could easily see him, naked and collared. At each stoplight he nervously glanced at the neighboring drivers making sure to try and avoid eye contact, especially those of the higher SUVs who could likely also see how his hands were restrained and his cock, naked and rigidly erect, maintained by Brian's conflicted feelings of excitement for exposure and fear of humiliation.

Finally, they turned onto a quiet street near the edges of the city, lined with very nice contemporary houses. Brian looked around admiring the luxury of the area and they turned into a driveway, continuing into the garage attached to one of the houses. He relaxed for a minute that the drive was over, and he was somewhat protected in his nakedness.

Kelly again leaned over from the driver's seat. She supported herself with her right hand on Brian's lower abdomen and leaned further to reach to the passenger door handle. Brian looked down here back to the curve of her ass in her fitted skirt, and breathed deeply in her scent, perfume mixed with desire still emanating from her pussy.

She gently wrapped the fingers of her right hand around his cock as she opened the passenger door for him pushing it open. Leaning back slightly, Kelly tested the stiffness of Brian's cock with light strokes looking up at him below his chin.

"Good," she said, "Looks like you are still eager."

"Yyyesss, miss," Brian moaned rocking his hips slightly into her hand.

"Get out, and go to the front door, I'll let you in there." Kelly instructed releasing him and moving to open her door and exit the car.

Brian paused for a moment looking into the car mirror at the driveway and neighborhood behind.

"Boy!" Kelly threatened bending over looking back into the car.

Brian turned looking to his boss across the car. He could see her firm breasts hanging in her fitted shirt as she bent back into the car. As well as the angry look on her face. He quickly swung his feet around and struggled slightly as he stood up from the low-slung vehicle.

"Good, boy," she said. This slight praise raised a warm feeling in Brian from his chest all throughout his body. "Now go to the front door and wait for me there."

"Yes, miss," Brian complied walking quickly from the garage. The plug shifted in his ass with each step and his erect cock bobbed in front of him. "The quicker I get there the less chance of exposure," he thought.

Kelly watched her toy's naked ass and legs flex as he walked out of the garage and toward the front walk of the house. Her pussy dampened once again at her plans, and she made her way to the door into the house and pressed the button to close the garage door behind her young employee.

Brian paused for a moment as the garage door slowly slid closed behind him. He stopped and looked back as it hit the driveway and stopped. He quickly glanced around. To get to the front door he'd need to make his way about a third of the way down the driveway then back to the house. There was some space between the houses of the neighborhood and many shrubs and trees blocking some sight lines, but any observant neighbor or passerby would surely be able to see him.

As quick as he dared Brian made it to the front door and waited. "Just a test," he thought, "Ms. Jones wouldn't want her neighbors to see him here like this, even more than he would want to be spotted."

He glanced behind once, a thick shrub near the porch would protect most of his lower body so prying eyes wouldn't see his naked ass and the plug that resided there. Still it would be clear there was a naked and collared man standing on the porch to anybody that cared to look or investigate further.

Inside, Kelly took her time. She placed her work bag and laptop neatly in her home office as she did every night. Then made her way to her bedroom to properly prepare for the rest of the evening.

Brian waited with growing nervousness at the front door. "What was taking so long," he thought his heart racing. He looked around more and more, trying to think of some escape. "Where could I go, though," he continued thinking. He bent to the side slightly to look into the side window of the entryway. There didn't seem to be any movement inside. "Where has she gone."

For a moment in desperation he thought of ringing the doorbell. He assessed the situation; the button was too high to reach with his hand buckled at his waist. Maybe if he bent over, he could push it with his nose. He sighed at the ridiculousness of the whole situation and was finally able to relax, resigned to whatever fate befell him.

Just as he did, the door finally opened. In front of him was his boss. Ms. Jones stood confidently wearing only a pair of leather knee high boots with tall heels. Brian's breath caught in his throat and his cock throbbed just seeing her standing there, feet spread to shoulder width, just a hint of her moist pussy lips below her bald mound, her pale lightly freckled skin set off by the black boots.

His gaze was drawn up from her exposed pussy to her chest where her firm breasts stood out, nipples already taut, either from the cool breeze of the open air or her own arousal. Kelly smiled and began to twirl the thin leash, Brian now notice she carried as well.

"Step forward, boy," she commanded.

Brian complied immediately nearly jumping to within reach of his boss. She reached out and clipped the leash to the leather collar around his neck. Then she reached down, her hand slid past his erect cock and grabbed his balls tight, she tugged him toward the interior of the house.

"Come in boy," she said, pulling him into the house by the balls, "we don't want the neighbors to get too curious."

"Y-y-es miss," he stammered, quickly stepping forward to follow her command and lessen the pain in his balls as she pulled.

Once inside Kelly released his balls and stepped around Brian shutting the door behind him. He found himself in the entry way of his boss's well-appointed house and large great room. As Kelly again moved in front of him, he could again smell the scent emanating from her pussy and his cock seemed to further stiffen.

Kelly gave a slight tug on the leash attached to his collar as she started to walk further into the house. "Follow me, boy."

"Yes, Miss." Brian responded. He quickly matched her pace a leash length behind Ms. Jones. He had no idea what more was to happen to him, but he moaned slightly as he watched her naked toned legs and ass, accentuated by the tall hells of the boots, flex as she walked in front of him leading him through the house.

Kelly stopped in front of a closed door, turned and stepped close to Brian. Still holding his leash, Brian watched as she ran her free hand slowly down her toned stomach, past her bald mound, and began to slowly stroke and rub her pussy. His mouth fell open and his desire evident in his cock as she pushed her fingers into herself and slowly coated them with her own heat. Kelly closed her eyes, tilted her head, back and let out a slow deep breath.

With this display in front of him Brian wished he could reach out and caress his boss's naked breasts, nipples stiff in front of him. His hands still shackled to his waist he could only watch; his cock began to drool precum with desire and his open mouth nearly followed.

Kelly pulled her hand back and opened her eyes, now looking directly at Brian. The hand his leash was in now also gripped his chin tightly. Her other hand coated with her own slick juices began to lightly stroke his cock.

"Mmmm..." Brian moaned, trying to meet her strokes with thrusts of his hips, his eyes closing.

"Look at me, boy!" She commanded. Brian opened his eyes and tried to focus on his boss's face as she continued to lightly stroke him.

"Remember, boy, you are here for punishment first," Kelly continued. "If you do well, you may be rewarded."

"Y-yes, miss, a-anythinngg," Brian moaned back to here, struggling to focus on her blue eyes as she increased the pleasure of his cock.

"Are you prepared to fully commit to me," she asked squeezing his chin tightly.

"Ooooohhhh, yyyesssss, miss," Brian continued he could feel his pleasure building in her hand.

"Good," Kelly said. She released both his chin and his cock. Brian thrust into air once before she roughly grabbed his balls and squeezed hard. "ON YOUR KNEES!!" She yelled.

Brian gasped at the sudden assault, but also immediately tried to drop to his knees. Kelly held on to his balls as he did, stretching them upward as he fell. Just as he was opening his mouth to exclaim, she let go and he landed on his knees gasping for breath.