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 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...
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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.
