Playtime with Miss Jones

The next morning was rough, his head hurt, his body ached and light stung his eyes and yet he smiled when he woke up, remembering the events of last night. Groggily he peeled himself from his bed, stripped off and took a long shower. Feeling fresher and more alert he remembered the collar. With just his towel he dashed back to his bedroom and checked the box. With a sigh of relief he saw the collar was sat in its box. He smiled, wondering how Amanda was doing this morning. He got dressed and made some breakfast before sitting down at his computer.

He looked at his list. He decided his first target for improving his life would be his manager at work as he would see her tonight on his shift. He pondered how he could get her to wear it. Pretending it was a gift for his girlfriend again might work like it had with Miss Jameson, but Jack found himself disliking that idea. Miss Jones was more distant from her staff than Miss Jameson was from her students. It wasn't she was a bitch, she was strict but fair, rather she believed that work was for work and not for socializing. Which probably meant if he mentioned a gift for a girlfriend, she would likely dismiss it as it wasn't work related. Hell he only knew her first name was Sarah because he had seen it on some paperwork, but there'd be hell to pay if he ever called her that.

He made his way to work just before his shift was due to start. He figured if he was going to get her to wear the collar, it would be easiest to do before he was on the clock. It was a modest sized bar with half of the space designated to food. It was extremely popular with students which required them to be very strict with checking people's ages when serving alcohol. He arrived just as it was starting to get busy for the evening. He had time to kill before he had to start so he made his way to the offices in the back.

"You're early," Miss Jones commented as he arrived at her office. She was sat at her desk that was littered with paperwork. She wore her usual blouse and pencil skirt and had her brown hair in a neat braid twisted into a bun. Since the day he had met her Jack had never seen her wear anything else or wear her hair in a different style.

"Yeah I was hoping to talk to you," Jack replied still unsure how he was going to play this.

"Can it wait, I've got a headache and a lot of paperwork to do," Miss Jones replied gesturing to the mountain on her desk. Jack saw an opportunity and it was thanks to a crappy TV commercial.

"I actually have something that may help with that," Jack told her as he went into his bag. He opened the box out of view of Miss Jones and retrieved the collar. He held it up for her to see.

"What is that? Some tacky necklace?" She asked.

"It's for headaches, have you not seen them before?" Jack lied.

"What are you talking about?" She replied.

"May I?" Jack asked without waiting for a reply. He grabbed her mouse and keyboard and quickly googled the advert he remembered.

"This is highly unpro-" Miss Jones replied before Jack cut her off.

"See, they have magnets that help to reduce stress and headaches in them," Jack cut her off as he found the product he was looking for. It didn't look much like his collar and he knew it was a load of shit they tried to flog on late night TV, but if it served as a good prop for his lie.

"Uses magnetic fields to reduce stress? What a load of rubbish," Miss Jones commented as she read the screen.

"It's worked wonders for me and I'm happy to let you borrow it. You're alone in your office, no one will see so what's the harm in trying it out?" He asked.

"I don't think-" she began before being cut off again.

"Think of it this way, it either helps and you feel better or it doesn't and it does nothing, you have nothing to lose," Jack pushed. He was on a roll and she was about to give in, he could tell.

"Fine give it here," Miss Jones sighed and Jack handed the collar. He watched with glee as she put it around her neck. The second the clasp locked her eyes seemed to glaze over.

"Sarah?" Jack asked testing it.

"Yes master?" She replied suddenly looking alert and staring at him.

"How do you feel?" He asked.

"Wonderful master, it's as if all my worries have just vanished. My only concern is pleasing you," she replied with a broad smile.

"Good, you can start by giving me a raise, I want double, no triple, my old pay and I was consistent shifts every week on the same days, no weekends though," Jack told her. He was sick of never knowing when he would be working and being unable to make plans with having to cancel half the time. And triple pay would mean he wouldn't have to worry about money anymore.

"Yes master," Sarah replied as she opened the employee files and began the paperwork she would need to complete.

"And I want a new contract, saying specified work hours and rate of pay with no way for it to be changed at least until I graduate, unless I wish to change it before then," he continued. At least then if Sarah did ever question why he had such high pay or set hours unlike the rest of the staff, or another manager replaced her, the contract couldn't be undone.

"Of course master," Sarah replied.

"Good, oh and I want to be able to take as many days paid leave as I like," he added. He figured being able to skip work whenever he wanted would be handy. How he would explain this to his co-workers if they found out he wasn't sure, but that was Sarah's problem not his.

"Yes master," she replied dutifully.

"Excellent. Right from now on I want you to act like yourself unless we are alone," Jack commanded. The last thing he wanted was people asking why his manager was calling him master and not doing any of her work. It was almost time for his shift so he left her to fill in the paperwork and got to work. It was a busy night but Jack actually quite enjoyed his job. He met a lot of interesting people and because a lot of them were students from college he overheard or was told a lot of gossip.

He went on his break half way through his shift and went to check on Sarah. He found her still at her desk tapping away at her keyboard.

"How is it going?" He asked. She looked at him before gesturing for him to come in and shut the door.

"It's going well master," she began once the door was shut. "I have filled in the paperwork, you're rate of pay is already in effect and I have a new contract here for you to sign."

"That was quick," Jack commented as he picked up a pen and read over the contract. It was exactly as he had stipulated and he signed it before Sarah co signed it. From now on be had every Friday, Saturday and Sunday off guaranteed.

"Is there anything else you would like me to do master?" She asked.

"Give me a massage," Jack told her. After last night and standing on his feet for hours his muscles ached.

"Would you like to lay down?" She offered, gesturing to the sofa at the back of her office. It had been known for her to sleep in her office if she was working particularly late. Jack stood up and moved to the sofa. He lay down on his stomach and Sarah came and perched on the edge next to his as her hands began to work on his back.

Jack could get used to this, a good paying job, easy shifts and a manager that would do what he liked and give him massages on his breaks. He knew most people would consider loftier goals in his situation, but right now, he was content to have Sarah work all the aches from his back. He could smell her perfume, he had never smelled it before. It was tropical, some kind of fruit mixed with coconut. He looked over his shoulder at her, she was smiling as she worked. He couldn't remember the last time he had seen her smile, if ever.

Her stocking clad legs were stretched out in front of him. She had great legs, long and shapely and well toned. He vaguely recalled her saying she enjoyed hiking in her free time once. It was about the only detail of her personal life she had ever shared. He was tempted to ask her, but was enjoying looking at her legs and feeling her hands on his shoulders. Despite how relaxed he was, his cock began to stir as he looked up her legs and began thinking more about her body.

His imagination ran wild, wondering what she looked like out of her clothes. They did little to show off her figure. The pencil skirt showed off her hips and that was it, while the blouse hung loosely hiding her figure. By the time she was done with massaging him he was rock hard and his mind was filled with curiosity. He rolled over and looked at her, his erection very obvious as it tented his pants.

"Undress for me," he said.

"Of course, do you need help relieving that?" She asked as she gestured to his erection before she began to undress.

"In a moment, I want to see you naked first," Jack answered. He watched as she stripped down. He put her age at somewhere around thirty two, since he didn't actually know how old she was. She stripped down, revealing small breasts and a thin body. She removed her bra to show off her small but pointed nipples. Next were her panties, they were plain cotton just as Jack had thought they would be. He watched as she pulled them down, showing him her mostly shaved mound. A thin strip of neatly trimmed hair ran down her mound leading to her pussy. She undid her hair and let it fall down her back.

"Do I please you master?" Sarah asked as she stood before him.

"Yes, now take out my cock," he commanded as he rested his hands behind his head. Sarah smiled and leaned over, unbuttoning his pants and pulling them down. She grabbed his cock and pulled it free of his boxers. "Now mount me and fuck me. I want you to enjoy my cock more than you've ever enjoyed one before."

"Yes master," Sarah grinned. She climbed onto the sofa and swung her leg over his, positioning herself above his cock. She gripped it and aimed it at her entrance as she lowered herself onto it. She groaned which quickly turned into a moan as his head penetrated her and he began to fill her tunnel.

"Oh fuck that feels good," she cooed as she slid down his length. He began to slowly ride up and down, looking him in the eye as she smiled widely.

"Your cunt feels amazing," Jack replied.

"Oh master, I usually hate that word but hearing you say it while your cock is inside me is so hot," she moaned. Jack had a feeling that she enjoyed dirty talk. With how professional she seemed at work, it didn't surprise him she might secretly be dirty in the bedroom. That was how the rumours about quiet people usually went at least.

"Tell me how much you love it," Jack pressed.

"I do master, I love your cock filling my cunt, stretching me open as I ride it," she cried out.

"You have to keep quiet," Jack reminded her. The last thing he wanted was someone to overhear if they walked past her office. Sarah leaned forward and whispered in his ear.

"Please master, I want you to fuck my dirty cunt until I can't take it anymore. I want you to make me beg you to stop, but keep pounding me anyway until you empty your load inside me," she purred in his ear. Jack couldn't believe she just said that and felt his cock swell inside her as he got more turned on. He grabbed her and rolled over on the sofa so he was on top of her.

"When you cum, it's going to be the best orgasm of your life. It won't end until I cum inside you. You'll be begging me to stop as the pleasure grows more and more intense you think your mind will break, but you'll love every thrust into you," Jack commanded. Sarah almost had an orgasm just from hearing him say it. He started to thrust into her and she grabbed his ass, squeezing it and pushing him deeper into her with each thrust. She moaned quietly, her head turned toward the back of the sofa.

Jack picked up the pace, he was still on break and was well aware people would wonder where he was if he was too late back. He began to thrust into her hard and fast and Sarah's moans rose in pitch. She buried her head into a cushion as she reached orgasm, one hand holding the cushion against her mouth while the other gripped Jacks ass cheek tightly.

"Oh fuck, fuck, fuckkkkkk," she cried out as Jack continued to pound into her. He watched her small breasts rise and fall as she took ragged breaths before crying out in another explosion of pleasure.

"Oh fuck, I can't, oh god, fuck," she rambled as pleasure overwhelmed her again. She dug her nails into Jacks back as she moaned out loudly again.

"I can't, stop, it's too much, please stop, my pussy, too sensitive, ohhhhh fuckkkkkkk," she cried as her whole body shook. Her legs tensed and seized, her toes curled and her entire body trembled. Jack slowed down momentarily and let her catch her breath before thrusting into her again. He didn't have the stamina to keep such a quick pace for much longer so he switched to long, hard strokes which had the desired effect.

"You have... To stop... I can't... I'm gonna... I'm gonna... Fuuuuuuuuuuck," she cried out as her whole body shuddered before tensing up. He felt her cunt shudder and clamp down hard on him before a torrent of fluid pushed past his cock and sprayed from her cunt. Jack didn't slow down, he felt his orgasm approaching. Sarah's body trembled continuously now and she was struggling to form words.

"Please... Fuckkkkk... I can't" she mumbled before moaning again as another waved of pleasure crashed through her. Her cunt was like a vice on his cock, clamping down and increasing his pleasure. He grunted as he began to empty himself inside her. She squealed in delight and her eyes rolled back as she felt her insides get flooded with his hot sticky fluid. Her walls trembled against his cock, squeezing every drop from him before he collapsed on top of her. He fought for breath, he couldn't remember the last time he had exerted himself like that and his lungs burned for oxygen.

"That... Oh fuck..." Sarah groaned as her body shivered in an aftershock of pleasure. Jack sat up, drawing his cock from her now red and abused pussy. The sofa was drenched between her thighs and he avoided that as he stood up. She looked at him with a dopey grin.

"So?" He asked. She looked at him not understanding. "Best orgasm you've ever had?"

"Yes, thank you master, I have never felt such pleasure. Feeling you pushing me to new heights of pleasure as I begged you to stop was incredible," she grinned.

"I should get back to work," Jack told her, noticing he was already ten minutes late.

"I think I'll stay here for a bit, I don't think I can stand right now," Sarah giggled. It was strange seeing such a cheerful and playful side to her. Jack shook his head in amusement at what the collar could do as he snuck out the door, quickly closing it behind him in case anyone was there. He finished his shift and went back to check on Sarah. She was once again dressed and typing away at her computer although she had decided against putting her bra back on or doing up the top few buttons of her shirt, which was extremely unlike her.

"Do you need anything from me master?" She asked as Jack entered the room.

"No I just wanted to stop by and tell you that once that collar comes off you'll be much warmer and friendlier towards me and be willing to fool around with me whenever I ask," he smiled. As much as he wanted to go another round with her right there and then he was far too tired. Taking her home was out of the question too as he just wanted to go home and sleep. By the time he planned on waking up, the collar would be off. He just hoped this last command worked so he could have some fun with her another time without needing the collar.

"Of course master," Sarah smiled at him.

"I'm going home, you should stick to your usual routine too," he suggested before leaving her and going home. It had been a long shift and while his activities during his break had been fun, they hadn't been restful. Grabbing a quick snack and a shower Jack fell into bed, falling asleep almost as soon as his head hit the pillow.

The next morning was a considerable improvement over the previous, which wasn't a surprise considering how hungover he had been. He checked the collar was back in its box where it belonged, which is was, before he sent Abby a quick message. He told her he had managed to collar Sarah and about his new pay and contract. He left out the sexual details, although Abby would guess what happened anyway. He grinned as he hit send, reading his message about him using the collar was probably enough to send Abby into an impromptu masturbation session.

Jack's day went fairly quietly. He attended his classes, which was made more fun by Miss Jameson bending over. This time it was clear she was wearing a plug, although Jack seemed to be the only one to notice. Maybe it was because he was looking for it. Other than that exciting event, his day was quiet until he arrived at work. He stuck his head in to see Sarah, just to test if his command worked.

"Hey Jack," she smiled at him.

"Hey, I was just checking how you were doing," he replied.

"I'm good, although these order forms are doing my head in."

"I know of a way to take your mind off them for a bit," Jack suggested, wondering if Sarah would take the bait.

"If you're wanting a quickie, I can't, these forms really need doing now," Sarah replied. Dashing his hopes. "Although, I was always good at multi-tasking."

Jack wondered what she was talking about, until she stood up and leaned forward. She bent over and reached back, pulling up her skirt. She hiked it up until her ass was exposed before pulling her underwear to one side, revealing her pussy. Jack didn't need asking twice as he stepped up behind her and unzipped his pants. His cock was already hardening and only needed a few strokes to bring it to full attention.

Sarah continued tapping away at her keyboard as Jack pushed his cock against her entrance. He watched the head slowly spread her large labia before it settled into her entrance. Slowly pushing forward, he enjoyed the sight of his cock sinking into her inch by inch. She gasped slightly as he filled her slick tunnel, but she continued with her work.

Jack took it as a challenge to distract her as much as possible, so he pulled back until just the tip was left inside, before slamming back into her with force. She groaned, but still didn't break from her work. Jack began thrusting, slowly at first, but quickly picking up the pace.

Sarah's office filled with the sound of his hips slapping against her pert ass as her she studied the screen. She was no longer typing, but Jack didn't know if that was because she couldn't while he was thrusting or she was just busy reading. Either way, she was leaving all the work to him, which he was fine with. Her cunt felt like velvet around his cock, smooth and soft, massaging every inch of his shaft with each thrust.

He wished he could spend his whole shift with his cock buried inside his boss, but he knew eventually someone would notice he was missing and come looking for him. Or they'd come looking for Sarah to report that he hadn't shown up for work. Either way, it'd involve someone discovering them.

Knowing this would be the only chance he had to fuck her today, Jack savoured the feeling. The heat and tightness of her tunnel, the firmness of her petite ass as he massaged it. Sarah started moaning and he looked up, seeing her hanging her head as she began to push back, meeting his thrusts half way. She groaned and Jack picked up the pace, ploughing into her with as much force as he could muster.

"Oh fuck..." Sarah groaned. He saw her hands gripping the desk tightly and knew she was getting close. He was also getting close, but he wanted to make her cum first. He tried to think of anything to distract him and delay his orgasm, but he was careering towards it like an out of control freight train.

"I'm gonna cum!" He warned.

"Me too! Oh fuck! Don't stop!" Sarah replied. He groaned and thrust into her faster, finding a burst of speed as he reached his peak. He slowed down and instead thrust in hard, forceful thrusts as his cock began to empty its load inside his boss. She cried out, louder than she should have if they didn't want anyone hearing and gripped her desk as her legs trembled.

"Fuuuuuuuuckkkkkkkkkk!" Sarah groaned as her orgasm washed over her. Jack pushed deep into her, his own orgasm spent as she rode out hers. She hung her head, panting hard as her orgasm faded. Jack slid out of her and Sarah reached back to return her underwear to it's usual position before pulling down her skirt.

"I should start my shift," Jack grinned.

"Yeah, you should before anyone asks where you are. Plus I need to finish these forms, seems I'm not as good at multi tasking as I thought."

"You just need practice."

"And I presume you'd be happy to help with that?"

"Just making sure we're all working to the best of our ability! I thought you'd be pleased with that," Jack teased.

"Go and start your shift," Sarah replied, rolling her eyes. Jack laughed and left the office, heading towards the bar. He marveled at how instantly the collar had changed his relationship with his boss, even when she wasn't wearing it.