Office Trouble

(Though my stories are standalone, they're all somewhat related. For a complete list of chronology, refer to my profile info.)

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Though I was an engineering major, in my late 20s the struggling economy forced me to leave my home state and work for a franchise of after school tutoring academies in the east coast. I started out as one of the instructors before working my way up the corporate ladder to become a branch manager in downtown Boston. The job was extremely demanding, which was why later I quit and returned to the west coast.

Aside from holding the occasional training workshops, I also had to watch every teacher's classes on CCTV in order to evaluate them. The corporation offered me a very generous remuneration, but what really enticed me was the unintentional benefit. Since the company demanded only the best and the brightest for hiring, the female teachers were the nerdy types. Coincidentally, I love nerdy girls. Why? Because nerdy girls always put on a conservative front, but inwardly they're as deprived as any girl.

During my early years as the manager, I met a very rambunctious young woman named Sarah. She was only 22 years old when I hired her fresh out of a top west coast university. Though she was extremely cute, she wasn't the slim body and long black hair "anime" type I liked. Sarah was more of a curvy build with natural curly brown hair. At 5'2" she was also shorter than what I typically liked. However, she was really cute especially with her almond eyes and sultry smile. She had a really naïve and cute personality and since we were both from the west coast, our relationship eventually grown more into a little sister and big brother kind.

I was quite protective of her at the company and mentored her under my wings. Since I was responsible for every teacher's class scheduling, I always gave her the best schedules with a light workload. She was an overachiever and always dressed more professionally than I required for the teachers, often in dress suits with her hair up in a bun. I was proud of her and very fond of her.

Now unfortunately, the after school tutoring industry wasn't doing so well. We had to cut teachers and increase teaching loads. It got to the point that we couldn't lose a single student to stay financially afloat. Since Sarah's teaching load was already light, I had to give her a few of the new assignments. The time slots for some of them were during full teaching hours and the only room left was the small conference room. It was a typical conference room with a big window facing the hallway, but the blinds could be closed for privacy.

At first Sarah seemed to be alright with the extra teaching load. However, as days went by, I noticed she was slowly losing that rambunctious smiling attitude of hers and it concerned me. Each time I talked to her about it, she claimed she was just a little tired from the extra workload. As I've said, I was a busy guy so I didn't think much of it.

This went on for a little over a week and then one day after her last course, she came out of the conference room a little late. I noticed her usually well groomed hair bun was somewhat loosened and her eyes were slightly red from tearing. She gave me a weak smile and told me she had terrible allergies that day. It made sense, so I didn't make a fuss about it. However, something didn't quite seem right and I was worried.

With tons of work, I was always the last one remaining at the office and that was usually the time I watched the CCTV recordings. At first I didn't find anything out of the ordinary going through Sarah's classes. Then suddenly I remembered that most teachers weren't aware of the CCTV in the conference room since it was not a classroom. Even I had forgotten about it and never watched it.

So I decided to watch from day one to see what had slowly drained this happy go lucky girl into such a tired and mopey drone. The first few courses were pretty normal. She was doing solo tutoring with each student. After fast forwarding a couple of days, I noticed something intriguing in one of her late courses.

She was tutoring a high school boy in math, which by the look of it was a high school athlete from a rich family. You know the type, dumb as a doorknob. The kid was stupid or just simply too apathetic to care. She tried her best but he just didn't get it. He was showing her his impressive "F" on a recent school math test. Sarah was visibly frustrated with his apathetic attitude.

The boy sighed and then said to her, "Why do you care? You're just paid to babysit me."

As I've said, Sarah was an overachiever and could not accept failure on any level. She replied to him, "Don't you know math is going to help you in the future?"

The boy rolled his eyes and responded, "I don't need math to play sports. I have no reason to waste my time on this."

With a deep sigh, Sarah asked, "Fine, tell me your interests and how I can motivate you."

After a short pause, the boy joked, "Well... show me your boobs if I pass my next test."

I thought Sarah would be furious with such an inappropriate joke. However, either she really just wanted to succeed with this boy or she thought it was impossible for him to pass, she replied, "Is that all it takes for you horny teenagers? Fine. One look if you can get a C. Not a C-, but a solid C."

I remember thinking to myself, "Well... this is interesting... Could she really... nah... no way..."

Without watching anything else, I eagerly fast forwarded a few days later to their next class. The boy was sitting there with a depressed and upset look when Sarah came in. Immediately, she noticed and sighed, "Didn't think so."

However, at that moment, the boy slipped out his latest test to her horrified face. It was there in a big red marking, "C." Sarah froze in an awkward pause as the boy grinned and said to her, "Pop them out, please."

She looked around nervously and hesitated before releasing a defeated sigh. Then to my surprise, she opened her suit jacket and unbuttoned her blouse, giving his lustful eyes a direct look at her plump juicy tits in a white laced bra. I was utterly stunned in shock! What was she thinking? I was so mad at her both as a friend and her boss. As a friend I had much higher standards for her. As her boss, I was looking at a lawsuit. However at the same time, I found myself unexpectedly aroused by the whole situation.

When she started to close her blouse, the boy interrupted, "Eh!! You agreed to show me your boobs... Not your bra."

Shocked by the request, Sarah denied, "No, I never said that. You said boobs, you saw my boobs. There is no way..."

Snickering, the boy interrupted, "Well, I guess that just makes you a liar. A fine lesson you're teaching me about the adult world and what I have to look forward to."

There was a long awkward pause before Sarah reluctantly lifted up her bra. My jaws literally dropped when her tits popped out as I muttered to myself, "Oh shit." She was so embarrassed, keeping her eyes shut as she exposed her tender breasts. Unfortunately, that was a mistake. The boy immediately reached out and cupped her tits with both hands and gave them a firm squeeze. She gasped in surprise and immediately grabbed hold of his wrists while staring right at him. The boy held on though, and with his thumbs, started rubbing both her nipples in a circular motion.

Sarah's almond eyes were in a helpless frown as she was unable to pry his hands off. Then she pleaded for him to stop and he finally let go of her tits, smirking with a reply, "Eh... that was fun teacher, thanks."

Embarrassed, she buttoned up and composed herself. For the rest of the lesson she was monotonic and awkward, but there was nothing else interesting about it. At the end of the lesson, the boy asked her again, "Teacher, since I've already touched your boobs. How about this for our next deal? If I can get a B, you will let me touch them again?"

Sarah paused for a minute in surprise. Then, not wanting to sound like she was ashamed about anything that had happened, she replied in a confident voice, "You got lucky today. You'll be lucky to even get a C again next time. There is no way you're getting a B."

After the boy left the room, Sarah sat there silently covering her face in shame. I shook my head in disbelief as I fast forwarded to today's class. It started again with the boy waiting for Sarah, except this time he was waiting eagerly and confidently. When Sarah came in, she had a fearful look after sensing his confidence. He slipped out his new test score with red marking, "B+" and told her with a grin, "Close that door, teacher."

I instantly groaned in disappointment at the video, but at the same time my dick grew in excitement.

Sarah cleared her throat and tried to weasel her way out of it, "Hey, yeah.. you know this is great you got such a good score. You should be proud of it... and we should just leave it at that. I mean, you're not serious about..."

The boy delighted in her futile attempt to break the deal and replied with a chuckle, "Don't make it such a big deal, I've already touched them last time. Nothing new."

Not being able to find a way out, Sarah slowly complied as she sat in the office chair. Like before, she opened up her suit jacket, unbuttoned her blouse and pulled her bra up. The boy quickly squat down behind her chair and secured her wrists together with a thick rubber band. I was literally taken off guard as I thought he was simply going to cup her tits again.

The sudden change of plan startled Sarah as she nervously asked, "Wtf are you doing!?"

With an evil smirk, the boy replied, "Relax, this is just to make sure you don't go back on our deal and suddenly change your mind."

Unable to do anything, Sarah reluctantly accepted her ordeal. He cupped her tits from behind her and started massaging them, pinching her sensitive nipples while squeezing her soft flesh. A flush of red hit Sarah's face as her body responded. Her breathing became heavier and heavier while she reluctantly bit and licked her lower lips as her body heaved with his massage movement. Then realizing her body was responding to his touch, she tried to hide her arousal by stiffening up.

He became rougher and rougher with his groping before whispering into her ear, "Teacher, your tits are so soft and yet so firm. They feel amazing... I've played with many high school girls, you definitely have no reason to envy them."

The compliment broke her resistance as she uncontrollably let out a whispering moan. When she did, he shoved 2 fingers into her mouth and started rubbing deep in the back of her tongue as she gagged. She was so lost in the moment that she hadn't realized what was happening and allowed him to finger fuck her mouth for a few minutes as gulps of saliva drooled out of her lips. Then frantically, she begged him to stop, mumbling through his fingers, "gug.. stop... it's enough... come on..."

Watching her so helpless was making my cock engorge and swollen. I had never imagined my so called "little work sister" in such a sexual context before and it had taken hold of me. Since I was alone in the office, I unzipped my cock and started stroking it while I watched.

The boy wouldn't even slow down. He went faster and rougher with her, pinching her succulent nipples while groping her tits and finger fucking her mouth. He leaned into her ear and whispered, "Teacher... you're so hot... I can't help it... you're making me so hard... I have to show you!"

Upon hearing those words, her eyes widen as she asked, "Wait... what? Show me what?"

With a hard shove, he pushed her office chair forward and she fell to her knees with her wrists still secured behind her back. Then with her blouse still open and her tits on display, he unzipped and pulled down his pants right next to her face. Sarah could not take her eyes off the huge bulge in his underwear and he teased her by pressing it right on her nose. Her expression was one of agony and lust, knowing everything was wrong but her body was in heat.

When he pulled his underwear down, his monstrous cock sprung out and hit her right on the cheek. He rubbed it around her face a few times and ordered her to admire it. After a few seconds, Sarah begged, "Ok, ok... I saw it... now put it away... please..."

Now us guys know that a guy does not take out his cock unless he intends to feed it. However, I was still in disbelief and thought to myself, "Nahh... he ... he wouldn't... he couldn't..."

Instead of complying with Sarah's pathetic plea, he started rubbing the tip of the cock on her face, smearing the precum all over her lovely cheeks. Then as she squirmed in disgust, he squat a little lower and started rubbing the cock on her juicy nipples. Despite her protest, her body was throbbing as he teased her nipples with his slippery cock head. Then, he took a handful of her hair bun and firmly grabbed her head. The pain from the hair grab forced her to cringe her eyes and open her mouth. Before she could make a sound, however, he immediately shoved that monster past her lips until it hit the back of her throat. While he rhythmically pumped her face, all she could do was pleading with muffling moans between each gag, "umf... noh... umf... umf..."

While holding her head firmly in place with just one hand, he punished her tiny mouth with eager hard thrusts. With his other hand, he lightly slapped her a few times while she choked on that cock and ordered her around, "Suck me harder... Yeah, show me how college sluts do it... Look at me! Look at my face!"

When I looked closely at the video, I noticed Sarah complied obediently, staring right at him the whole time with tears rolling down her cheeks while he viciously slammed into her lips until he came deep into her throat. At the exact same time I came so hard that I shot my load all over the computer monitor.

Before a drop of it leaked out, he quickly knelt down and covered her mouth, whispering, "You still have to walk out of this office. If you don't want anyone to find out, you'd better swallow the evidence."

Without any choice, she obediently swallowed his sticky gunk and sobbed softly on her knees. He untied her and cleaned up. Then, opening the door and checking if anyone was outside, he left without a word. Sarah sat there for the rest of the hour sobbing before straightening her clothes and walking out. That was when I ran into her earlier today.

Speechless would be good way to describe my feeling as I sat there in the office. After my sexual tension was freed all over the monitor, reality hit me like a ton of bricks. I was filled with a mixture of confusion and anger. I was furious at how this punk kid ravaged this innocent young woman. At the same time I was so disappointed at her naïve attitude. Then fear set in as I realized we're looking at a lawsuit if this ever got out. A scandal was the last thing this company needed as we were barely staying financially afloat.

There was some good news. I checked the boy's profile and found out he was a 19 year old high school senior. By the look of his grades and his entitled attitude, he probably had to repeat a grade. I was relieved that at least Sarah was not in trouble with the statutory law. However, despite my best efforts I could not get one thought out of my head— I was so aroused by the video that I couldn't help but hunger for more.

After some contemplation, I decided to make a copy of the video before wiping the evidence from the system to protect her. I wrestled with whether to talk to Sarah about this incident. The next couple of days, she was quiet and nonsocial like she had been since I put her on these extra courses. When the day scheduled with that boy came, I was relieved he had cancelled his time slot. I informed Sarah and her eyes immediately brightened in delight. I was hoping this was the start of her returning back to her normal self. She went through the whole day cheerfully like she was before.

Unfortunately, as the work day was coming to a close, I was informed the father of the boy had called in requesting a meeting with Sarah. I panicked and again a slew of legal matters flooded my mind. I wondered if he found out. Was he furious? Was he going to sue us? A solemn fear set over Sarah when she heard the news. I reassured her that he was probably just going to thank her for his son's recent academic improvement. Spacing off unsure, Sarah replied, "Yeah... I guess that must be it..."

It was during the last course hour of the day when the father showed up. Being the manager, I greeted him immediately. He was a tall fat man in his late 50s, dressed very well in a suit. When I greeted him, he didn't seem mad so I was relieved. I told him his son's progress was extremely encouraging and that we were very happy with his business. He agreed and told me that was why he wanted to meet Sarah in person. Delighted, I offered to sit with them in the conference room. However, he declined and said he wanted to talk to her alone, concerning private matters about his son's education which he felt was personal. Reluctantly, I allowed them to meet alone.

Before Sarah went in, I put my hand on her shoulder and reassured her. She took a deep breath before going into the conference room. I quickly went into my office and watched on the CCTV with headphones on, hoping this would be just another standard parent-teacher meeting.

The moment the door closed and they were alone, the father's demeanor shifted dramatically. He looked at her sternly and said, "What the hell did you do to my son?"

Sarah froze like a deer in the headlights and I could tell she was scared. Then in a trembling voice she replied, "I'm sorry? I thought he has been doing great. If you look at his test scores..."

Before she could finish, a hard slap came across her face and a high pitch yelp escaped her lips. I almost got out of my chair and marched into that room. Furiously, the father grabbed her hair and said to her, "You dumb bitch! You're really this stupid?"

He opened his briefcase and threw his son's test papers over the table and continued, "Look at it! You don't realize the hand writings are different on all of these? These aren't his test scores!"

Sarah was visibly shaken and quietly sobbing. Looking over the test papers, she realized she had been tricked by the young boy. Then she pleaded softly with the father, "Please sir, I didn't know... I guess I was so eager to see him succeed, perhaps he just didn't want to disappoint me..."

Without warning the father slapped her a 2nd time, "Don't play dumb with me bitch! You think I don't know? He bragged about it to all his friends. I know what you were doing with the time I paid for his education!"

Shocked in disbelief, she started visibly crying. The father was right about one thing, I just couldn't believe how naïve she was. However, I couldn't stand watching her being abused like this and was about to intervene when he continued, "I'm paying $500 per course. That makes you a $500 whore. Are you worth $500?"

Sarah replied in a sobbing whimper, "Wait... what? I'm not... you see... at first it was just..."

Before she could finish, the father leaned in and grabbed her by the throat then whispered directly into her face with a sinister tone, "You're going to show me that $500 service I paid for... and if you make a sound or you tell anyone... I will destroy you... I will destroy this company. You're going to jail for statutory rape. Do you understand, whore?"

The sudden turn of events triggered a raging hard on in my pants and I couldn't help but sit back down. I couldn't believe this guy! I already checked his son's age, he was 19. This fat bastard was lying to blackmail this naïve young woman and forcing her to become a $500 prostitute. I was caught in my own dilemma, fighting my sexual frustration versus protecting my so called little sister. Then there was the whole legal issue of protecting her and the school from a scandal. I was helpless to intervene and could only sit there watching it unfold.