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Jack Stone awoke to his alarm going off at its usual time of 5:45am. Monday morning always came too early and he struggled to get out of bed to start his day. Jack needed to make sure to get into work before his boss, Miss Elizabeth Jones, to be ready for whatever she demanded of him first thing.
Miss Elizabeth Jones was vice-president of a large insurance company in Southfield, Michigan and Jack was her executive assistant.
As Jack began his morning ritual, he thought about his boss and the outfit she was wearing earlier in the week. Elizabeth, or Liz as she liked to be called, always dressed professionally, but the black skirt and blouse she had on a couple of days ago showed off her early 40-something figure quite well. The skirt hugged her hips and ass, and she wore the blouse unbuttoned just enough to show off some cleavage. Jack, being single and 28 years old, enjoyed working closely with Liz on a daily basis.
Jack arrived at work slightly before 8am, with his coffee and an espresso for Liz, and waited for her arrival and what she had in store for him today. Liz was a very demanding boss and expected nothing but the best from Jack. She could be extremely demeaning at times when she was displeased with her employees, but always very honest.
Liz arrived to her office at 8am and greeted Jack with a sour, “Good morning,” took her espresso, walked into her office and closed the door behind her. “Great,” thought Jack, “she’s in a wonderful mood.”
After waiting about 15 minutes, Jack knocked on her office door. “Yes,” he heard her say, as he opened the door and walked in. “Everything okay?” he asked.
“Of course,” she replied coldly. “Well, I thought we should get started,” Jack continued. “You have a 9am meeting, and we need to go over some final details before.”
Liz looked up at Jack with her beautiful dark eyes and said, very calmly, “Very well. But I’m sure I have all the details covered and am ready for my meeting.” With that, she stood up and ushered him out of her office and again closed the door to be alone.
The rest of the day didn’t go any better and Liz took whatever was bothering her out on Jack any chance she could. She finally left for home at 6pm and Jack was able to relax some before heading home himself. He had heard Liz talking to another female exec about a blind date she had earlier in the week that didn’t go very well. Something about her being a cold, insensitive bitch, or so that’s what she was told by her date. Jack knew why she was in a bad mood and wished he could do something to cheer her up, but he wasn’t sure what that was or if he should even approach Liz about it.
For whatever reason, Jack decided to take the long way home that evening and drive through Liz’s neighborhood. Liz lived in an upper class neighborhood on the outskirts of Southfield and it was after dark by the time Jack pulled up outside her house. None of the outside lights were on, and in fact the house looked empty, except for one light coming out a window near the back of the house. Liz’s car was in the drive, so he knew she was home, he just didn’t know if he should go up and knock, or what.
Quietly, exiting his car, Jack decided to peek into her window to see what she was doing. He knew it was wrong, but Jack had a crush on his boss and was a little voyeuristic as well. So, he looked around at the other houses and crept around to the side of the house with the lighted window.
As Jack crouched next to the window, he saw Liz come out of her bathroom into her bedroom, clad only in a bathrobe. Her long dark brown hair was loose and draped over her shoulders, something Jack had never seen before. She always wore her hair up at the office. Jack thought of how beautiful she really was as he gazed upon her through the window. Her hair was damp and what skin he could see was still moist with water from the shower. She stood before the mirror in her room, brushed her hair and released the tie at her waist to allow the robe to fall open.
Jack’s jaw dropped open. Liz was gorgeous. Her body was definitely not that of 40-something year old woman, but looked to be tan and toned. Not that women her age couldn’t look this good, it’s just Jack never imagined how incredibly sexy his boss was, until there she stood, almost naked before him.
She stopped brushing her hair, put down the brush and brought both of her hands to her body, opening the robe even more. Liz was still upset about her date and wondered to herself why she was still single at her age. “I’m still sexy, aren’t I?” she asked nobody in particular as her hands wandered over her breasts, stomach and hips. She shrugged off the robe and stood there naked before the mirror.
Jack was amazed with the beauty before him. Liz wasn’t tall, maybe 5’6″ or so, but had long sensuous legs that ended with a small patch of dark brown hair above her pussy. As Jack stood there fixed to the spot, her right hand wandered down between her legs and slowly stroked her slickness. Her other hand bursa escort bayan was now cupping her breasts and gently pulling on her nipples, making them stand at attention. Soft moans escaped her mouth and she closed her eyes as she started to really enjoy herself. “It’s been too long,” she thought to herself.
She sat down on the edge of the bed, still facing the mirror and spread her legs, leaned back and slowly slid a finger up and down her wet slit. Pulling that finger to her mouth, she sucked it in, tasting herself. Liz was oblivious to anything else going on around her, as her hand returned to between her legs and she moaned as she slid two fingers inside her. Her other hand, tugged harder on her nipples as she pulled her breasts to her mouth to lick each nipple in turn.
Laying back on the bed, now, both hands between her thighs, Liz continued sliding her fingers in and out of a now very wet pussy, while with her other hand she began to rub her clit from side to side. Biting her lip and moaning very loud, Liz had a wonderful orgasm and continued to lie on her bed, her breath slowing down as her hands remained between her legs, gently rubbing her pussy.
Jack couldn’t believe what he had just witnessed, blinked and decided he better get out of there before one of Liz’s neighbors called the cops. His cock was straining in his slacks and he couldn’t wait to get home and rub one off himself.
Tuesday came and went at the office, as Liz was out most of the day at meetings.
Even with her gone, Jack had a hard time concentrating on work after what he witnessed last night. Jack tried to keep himself busy, but images of naked boss kept popping into his head. He couldn’t wait till 5pm to roll around, so he could head home and try relaxing. But, he wouldn’t…
The whole next day, Jack couldn’t get the image of Liz masturbating out of his head, but she was in such a foul mood it didn’t matter. What ever happened yesterday at her meetings put her in a very bad mood, which she took out on him all day. He just wanted the day to be over with quickly, so he could just get away from her for the night.
Instead of heading home, though, after the day was done, Jack decided to follow Liz home again, hoping for a follow-up masturbation session. On the way to Liz’s house, however, Jack thought about what he could do to help his boss. Being the sly young man that he is, Jack hatched a plan on the drive to Liz’s house. Remembering the key to her house he had been given when he started working, Jack stripped down to nothing, grabbed his long trench coat and a mask he had from last Mardi-Gras in his car. He again, quietly left his car in front of Liz’s house and snuck up to the house.
Jack stood at the front door, frozen, waiting. “But waiting for what?” he thought. He had been to Liz’s house before for a holiday party, but couldn’t remember the layout all that well. He took a deep breath, slid the key in as quietly as possible, slipped the mask on and opened the door.
The house was quiet and dark, just like the night before. Jack hoped she followed her previous night’s routine. As he crept through the house, he heard music coming from the back corner and smiled as he snuck up to the bedroom door, where he now heard the shower running as well.
Opening her bedroom door as quietly as possible, Jack crept into Liz’s room. The bathroom was to the left and he looked around for someplace to hide, until she came out. He was making this up as he went and realizing he wasn’t very good at it. He flipped off the bedroom lights, hoping to catch her as she went to turn them on.
The shower stopped and he could hear her getting out. He jumped into a closet with a view of the bathroom, hoping she couldn’t see him. Keeping the door slightly ajar, Jack waited and tried to calm himself down.
Liz stepped out of the bathroom and looked around suspiciously at her now dark bedroom. Not thinking anything of it, she started to walk across the room to turn on the lights, when a hand grabbed her and another covered her mouth before she had time to scream. She was terrified. Struggling to get free she relaxed a bit when her captor spoke.
“Please don’t, I don’t want to hurt you.” she heard him say in a very soothing way.
“Leave the lights off and don’t scream. I promise it will be okay.” he continued.
Liz relaxed. There was something familiar about the voice, but she couldn’t be certain; it was muffled, so it wasn’t clear. All she knew was that she was dripping wet from her shower and naked under her robe here in her bedroom with a stranger, and it excited her more than she cared to admit.
“Don’t turn around and take off the robe.” the voice demanded.
Liz started to turn around as she dropped the robe to the floor, revealing her still wet naked body, when the man behind her yelled, “I said don’t turn around!”
She froze. Excitement gorukle escort and fear both washed over her. “What did he want?” She wondered.
Then he was standing behind her and she felt his erect cock press up against her ass as his hands grabbed her by the waist. She wanted to scream, but she also wanted him to keep going; it had been too long since she felt the touch of a man. His cock was very hard and settled in the crevice of her ass; his hands wandered up and roughly grabbed a breast in each, the nipples hardening to the touch. Pushing her towards the bed, he kept her facing away from him.
Pulling a blindfold from his coat, Jack wrapped it around Liz’s eyes and tied it tight behind her head.
“No peaking.” he whispered in her ear. A shiver ran up her spine as she shuddered.
Jack grabbed one of Liz’s scarves and tied her hands behind her. Pushing her forward onto the bed, he pulled her to a kneeling position and spread her legs. Jack reached down with his hand and found Liz’s pussy to be very, very wet.
He bent down next to her and whispered again in her ear, “You are enjoying this, aren’t you, you naughty girl.” Liz shook her head up and down and replied, “Yes.” in a weak whisper.
Jack knelt behind his boss and inhaled her scent. He had imagined how her pussy would look and wasn’t disappointed as he spread her cheeks and leaning down, he gently licked up the entire length of her pussy to her ass, even running his tongue along her asshole. A quiet moaned escaped Liz’s mouth.
Standing again behind her, Jack positioned the head of his hard cock at the opening of her pussy and slowly slid his erection inside her. Jack grabbed her hips, pulled out his cock till only the head remained, then slid it hard back into her. Over and over again, Jack slid his cock almost out, only to slam it back inside her. Her moans became louder with each thrust of his cock.
Liz only wished she could reach back and pull him harder into her. She loved the way this man’s cock felt inside her pussy. Liz came hard as Jack continued to assault her body, and Jack was very close as well.
Not wanting to cum in her pussy, though, Jack pulled Liz down off the bed and to a kneeling position before him.
“Open your mouth,” he demanded.
Liz did as she was told and Jack stroked his cock a couple of times before unloading his warm cum into her waiting mouth. Drop after drop hit the back of her throat and she swallowed it greedily, loving the taste.
Licking her lips, Liz wanted to look upon her masked man, but she heard him open the bedroom door and he was gone. She was left, naked, tied up and blindfolded to figure out how to get loose on her own.
The next day began the same as the previous ones. Jack arrived to work at his typical time; however, Liz was already there. “Hope she’s in a better mood today,” thought Jack as he knocked on her door.
“Come on in, Jack. Beautiful morning, isn’t it?” Liz asked with a beautiful smile.
“Good morning.” replied Jack as he handed her the espresso.
“Yes, it is a beautiful morning.” he answered with a return smile.
“Well, I hate to ruin it so early, but you better cancel any plans you might have for tonight; it’s going to be a long day.” said Liz.
“No problem. Really didn’t have anything special going on. What’s up?” asked Jack.
“Remember those reports you were working on earlier this week? Well, the deadline for those reports has been pushed up to tomorrow. I know, I know, you’ve been working hard, but we have to put the time in tonight to finish them,” stated Liz as she looked up at Jack with her beautiful brown eyes.
“Well, we better get working then,” Jack said as he smiled at Liz.
The rest of the day was spent going over all of the details that Jack had gathered earlier in the week to make sure that everything was accounted for. Everything was there, but something wasn’t coming together as it should be and both Jack and Liz were beginning to become frustrated. It was nearing 8pm before either one of them realized how late they had been working.
Jack sat back, tired and frustrated. He had worked too hard on this all week for something to go wrong, but it had. Liz was fuming.
“How could you…I mean, really, you’ve had all week to pull this shit together, but…” she said glaring at Jack. “We’ll be here all night fixing this!” she yelled, as she slouched down in the chair on the other side of the table.
Liz just sat there across the table looking at Jack with such a pathetic look of disgust in her eyes.
That was it. Jack couldn’t take any more of this.
“Look, Liz, I’ve worked my ass off this week for you, just like I do every day and I’m tired of you treating me like crap,” yelled Jack back at her.
Liz just continued to glare at Jack from across the table, until a wicked thought came to her.
“What are you going to do about it, Jack?” she asked with an evil smirk.
“Pull me over your bursa merkez escort bayan lap and spank me?” she asked with raised eyebrows and a smile, knowing full well that he wouldn’t, even though they were completely alone in the office.
“Don’t think I’m not tempted,” replied Jack with an evil grin of his own, not knowing where the hell this was leading to.
The room was silent as Liz stood up, walked around the table to the side where Jack was sitting to stand right next to him.
Looking down at him with those sexy, dark eyes she asked, “What’s stopping you?”
Jack wasn’t sure what to do. Here was his boss, standing next to him daring him to pull her down over his lap and spank her? His mind was racing and replaying the scene from the previous night when he had spied on her pleasuring herself.
Liz interrupted his thoughts and asked, “Well, are you going to spank me or what? Haven’t I been a naughty girl?”
Jack didn’t have to be asked again. He reached out, grabbed Liz around the waist and pulled her down over his lap. Surprised, she let out a squeal, but smiled as she ended up with her ass facing up.
Jack placed his hand on his boss’s ass and gently rubbed her cheeks through her skirt. Liz turned back, looked at Jack and mouthed the words, “Spank me.”
He raised his hand and it came down hard on her ass. Even through her skirt it hurt, but she liked it. Jack looked at Liz, and said, “It’s about time someone treated you like this, but I think it would be better without the skirt, don’t you?”
“What do you want me to do?” Liz asked, innocently.
“Stand up and take off your skirt and blouse,” replied Jack, “and do it now!” he demanded.
Liz had never been treated like this before, until the other night, and she had never been more turned on than she was right now. She could feel the dampness growing between her thighs as she began to remove her blouse and skirt exposing her matching black lace bra, panties and thigh high stockings. Standing almost naked before her young assistant, Liz felt like the sexiest woman in the world.
“What now?” she asked, with her killer grin.
Jack moved his chair back away from the table and motioned for her to stand in front of him. “Turn around and bend over the table,” he stated.
Liz looked at Jack and wondered how far this would go. “Now!” he demanded.
Liz turned around and slowly bent over the table in front of her assistant, spreading her legs slightly and grasping the other side of the table.
Jack’s right hand returned to her ass as he leaned in and planted a soft wet kiss on her left cheek. He raised his hand and with a much louder smack, it came down hard causing Liz to jump and scream. Her cheek was red and Jack rubbed it to soothe the pain away. Both hands were now on her ass, as Jack kissed the red spot he just caused. He raised his left hand and with another loud smack, spanked Liz again. The cheeks of her ass were both now red and the moistness between her legs was extreme. She needed him to touch her there. She wanted to feel his hands between her thighs. She turned and looked at Jack with pleading eyes.
Jack had never seen anything or anyone as sexy as his boss before him.
“Let your hair down, Liz.” he suggested as he continued to rub and lick her ass.
Liz reached up and let her hair loose and at the same time undid her bra so she could tug on her nipples as Jack continued. Jack pushed his chair back and knelt behind Liz, his hands reaching up and slowly pulling her panties down over her ass, till they were on the floor at her ankles. Leaning in Jack slowly licked from her clit to her ass with his tongue.
A low moan escaped Liz’s mouth as she begged Jack to continue. “More,” was all she said.
Jack raised his right hand again and Liz braced for the spanking as his hand came down again, harder this time. “God, that felt good,” she thought. Jack licked the fresh red spot on her ass as both of his hands continued to wander over her back side. His tongue returned to her wet pussy, sliding in and out again and again. Liz’s moans became louder which encouraged Jack to continue. He slid two fingers deep inside her as he sat below her to suck on her clit. Sliding his fingers in and out of her, Jack slid his tongue back and forth across her clit and Liz came for the first time that evening.
Jack stood up and told Liz to get on her knees. She obeyed and kneeling naked before Jack, began to unbuckle his pants without being asked. She wanted to taste her young assistant, to return the favor and hoped to be as pleased with his cock as she was with his tongue and fingers.
Jack unbuttoned his shirt as Liz undid his pants. Pulling them off along with his boxer briefs, his hard erect cock sprang towards Liz’s waiting mouth.
Liz was not disappointed and immediately took his cock in her right hand and placed her lips around his head, slowly stroking his cock while sucking on him. Liz kept stroking his wonderful cock, as she leaned in and sucked each one of his balls into her mouth, coating his sack with saliva. She returned her mouth to his head and engulfed him as much as she could, sucking most of his cock inside her warm mouth. Jack’s hands fell to her head and he held her there briefly before letting her release him.
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