Sir Bossman Pt. 02

Sir Boss Man Part 2

Emily wakes up in her own hotel room a few hours later, very groggy and a little disoriented. Her ass still tingled from the punishment she took and she smiled a shy grin to herself thinking back on it. She took a moment to reach her hand down into her panties and found she was still soaking wet from her night with Jim. She couldn't help but bite her bottom lip thinking back on all the ecstasy he gave her. Her fingers were moving inside her when she remembers she is there to meet the stupid boss, 'yuck' she thinks almost out loud. She will make him pay...

Emily begrudgingly rolls out of bed to get ready for her meeting. As she walked by the mirror she noticed a nice hand print still peaking out from around her nude thong. She traced around it and found it aroused her, but after a few moments she forced herself to stop so she could focus on her meeting. "Right", she said out loud to herself, "let's get this done!". She looked at her attire options and realized she didn't have much to work with since her missing luggage was never found. She paired a tight black pencil skirt that just graced the top of her knees with a blush button down blouse that never really did button properly in the front. Usually she would wear a camisole under it, but as that piece of clothing was missing, she was forced to go without. This exposed the black push up bra underneath and made Emily quite self conscious. She hung her head low as she slipped on the only heels she had left, four inch strappy, black stilettos. And off she went to meet the boss.

The company's Vegas office was only a short cab ride away and before she knew it, Emily was walking into her own personal form of hell...cubicle world. She asked a plump, but friendly looking lady stationed towards the front of the room for directions to the boss's temporary office there and was directed to the 13rd floor. She decided to take the stairs and get in a few extra steps. After all she was looking at logging over 52,000 steps the day of her marathon and every training step counts! Plus a quick dose of endorphins couldn't hurt at this point.

Standing in front of the boss's door her cheeks were flush from the hurried 13 story climb in heels. She nervously straightened her now noticeably shortened skirt with her hands and did her best to hide the fact that her bra could be seen peeking out, ever so slightly, from between the third and fourth buttons of her fitted blouse. Luckily this floor seemed to be mostly deserted, so no one saw this display of nerves. With a final sigh, Emily knocked at the big bosses door.

From the other side of the door she hears a peppy, " Please come in!". The voice was somehow familiar to her. 'How odd as I have never met the Director of Customer Excellence', thought Emily as she opened the door with her most confident and business casual smile carefully placed across her face. When she saw the man who belonged to that oddly familiar voice, Emily's smile quickly changed. She found herself instinctively biting her bottom lip from a very unanticipated sense of arousal. "Sir Boss Man! I mean Jim!" she exclaimed as she once again began to nervously try and close the gap that exposed her now slightly heaving black bra.

Jim was clearly just as flustered as Emily in this moment. His eyes caught a glimpse of the black bra that not that long ago had been thrown recklessly away to the floor of his hotel suite. His mind wandered back to that moment as he temporarily lost the carefully constructed professional persona he was so good at portraying at work. He let his eyes stay on her heaving breast for much longer than was appropriate before he snapped back into his boss roll. "Emily, please have a seat. We have much to discuss!"

Emily quickly pulled herself together, which was very difficult considering the posh British accent, exquisitely tailored suit, and intoxicating cologne Jim had going for him. She took a seat opposite him from the desk and made sure to keep her knees politely together, but her breasts pushed prominently up and out. She had not missed how long his eyes had rested on her ample cleavage and she was in the mood for payback!

Mixing a business like voice with a very flirtatious glance, Emily began her assault. "It's so nice to officially meet you, Jim, or should I say 'Sir Boss Man.' What brings you here?" She watched as he once again faltered and she giggled to herself. Emily was now completely clearheaded and in her element. "You are an excellent employee Emily, and your hard work has not gone unseen", started Jim. He never mixed work and pleasure and this was exactly why. He could not stop thinking of her ass, high up in the air, or her wet pussy just waiting for him the night before. "The company asked me to meet with you to start training for a management position in customer excellence." Jim continued. "Is that so!" exclaimed Emily. She too struggled with the desire to play against the knowledge that she should stay professional. 'But HE started it!' she thought and the desire to play won out. She stared Jim right in the eyes and said, "I guess I am due a reward then! I wonder what it will be!"

Jim stammered at how forward Emily was being and that just excited her more. She felt sexy and empowered in a way she had never imagined she could. She gave her first order. "Lock the door." Jim was not at all used to taking orders. He was the boss in and out of the bedroom! Who was she to talk to him in such a manor. He was about to set this little lady straight, but when he looked at this less inhibited version of her he suddenly realized he was incredibly aroused. Without a word he went to lock his office door. Emily could also tell he was enjoying this from the prominent bulge in his well tailored pants. "Thank you Sir Boss Man" teased Emily as Jim returned to his desk, still not really sure what was happening. His day was taking a very unexpected turn.

Now that the door was secure, the fun could really begin. Emily got up and walked towards the now seated Jim. She sat on the corner of his desk. They locked eyes as Emily grabbed his right hand and pulled it towards her body. Slowly, she repositioned his hand so that only his pointer and middle finger were extended never breaking eye contact. She bent her head slightly to take the fingers into her mouth to suck on them. She moved them in and out a few times before forcing them deep into her throat. As she slowly pulled them back out, she pressed her tongue ring along the bottom of the fingers. When she reached the tip, she nibbled ever so lightly eliciting a soft groan from Jim. "I would like my reward now. Are you prepared to give it to me?" Jim nodded and Emily bit her bottom lip.

She slowly opened her legs for him, but quickly shut them as Jim greedily moved to position his mouth over the thin cloth of her lace panties. "Tisk, tisk, tisk Sir Boss Man. That is not allowed yet. I want you to only use your fingers." He obediently withdrew his mouth and her legs opened again. Jim pushed them further open before pulling her panties to the side and sliding his two fingers deep inside her. A good finger bang was one of Emily's favorite forms or fore play and her back arched away from the desk as she enjoyed feeling him move forcefully in and out of her wet slit. Before long he added a second hand to work her clit while he was fingering her. Emily needed more. "Oh god Jim, Fuck me, Fuck me now!" "I am due a reward first," responded Jim as he pushed her back against his desk and forced her legs high into the air, "and I plan to enjoy it!".

She couldn't stop him, Jim ripped off her panties as his animal nature took over. He licked her wet clit up and down causing Emily to gasp from excitement and pleasure. The power table was turning away from her, but she could care less with how good Jim's mouth was making her feel. His tongue worked her over well and proper. Up and down, in and out. She was ready to cum and she wanted to be fucked for that. "Please, Sir Boss Man, PLEASE, fuck me till I cum!" Gasped Emily as her nails ran up the length of his back.

With obvious experience, Jim flipped Emily ass up over his desk. He bent her fully over as he hiked her skirt up over her hips. "I'm afraid you can't have that just yet my dear...I am not done enjoying my reward. Stay just like this." With that, Jim took her pussy back into his mouth. He could tell she was close to organism and he intended to taste her juices when she came. "Oh god Jim, I am going to cum!" Cried Emily and he continued to work his tongue quickly on her clit. Emily moaned and her knees gave way as the organism took her over. She was breathing hard when Jim finally gave her what she was asking for and forced his rock hard cock inside her.

Jim enjoyed feeling her wet pussy take him fully in and he waited a moment between thrust to admire how she looked with her ass bent over his desk and his dick wholly pressed inside her. He couldn't help himself and he slapped her ass hard, once, and then a second, and third time. Emily groaned as she felt both pain and pleasure simultaneously. "Fuck me harder!" she wailed. "Harder Sir Boss Man! I need to feel you!" Jim obliged and rammed his cock into her pussy again and again and again. "You feel so good" uttered Jim almost unknowingly. This sparked something in Emily and she demanded to change it up.

"Fuck me against the window!" Jim's talent showed again as he smoothly transitioned Emily from bent over his desk to picked up against the full length window of his 13th floor office. He had his arms under each of her smooth and tanned legs and her ass was fully pressed up on the window in clear view of anyone who glanced that high up. But she didn't care and Jim didn't stop. At this point he couldn't. He needed the release and Emily wanted it from him. "I want you to cum inside me Sir Boss Man. I want to feel you cum!" His hands were grabbing her ample ass as he thrust harder and faster into her. She dug her nails deep into his back as she leaned over and whispered, "cum for me Sir Boss Man" in his ear before biting the base of his neck hard and with purpose. That was all he needed. Jim released into Emily with a loud moan of pure ecstasy.

As he placed her back on the floor, Jim reveled in how good it felt to fully give into Emily. To listen to her desires and commands and not just his own. He watched her slip her lace panties back on and shimmy her tight skirt back to a respectable position. What was next? Would he ever see her again or was this trist all the universe would allow for them? All he knew was that he would be enjoying thoughts of Emily and this "training session" for many weeks to come.