Mentoring The Intern free porn video

I hadn't liked the program at first, not a bit. It had started years ago with the "Take Your Daughter to Work Day" craze, when we had surrendered one working day a year to well-intentioned but nevertheless unproductive social engineering. Still, had it been up to me, I might have tolerated that annual waste of time, as proud mothers and fathers paraded their ever-so-bright daughters through the workplace for eight-odd hours of glorified babysitting. But this new program was just too much – it made "Daughter Day" seem like an austerity program

But it wasn't my call. I was the top executive at our regional facility, but the directive had come from the corporate headquarters. "Take Your Daughter to Work Summer" was launched. To be fair, it was supposed to be more productive than the original observance, which had always been nothing more than a show-and-tell day when very little "work" was accomplished by anybody. This new program was for older girls only, sixteen and up, and they were to work for the company as actual summer employees, really producing something and supposedly developing confidence and career goals.

When the email notice went out, it didn't surprise me in the least that the first person through my door was my so-called executive assistant. I had "inherited" Marsha Jacobsen from my predecessor, and I had always found her only marginally competent. This problem was exacerbated her unfortunate migraine problem, which kept her stretching the absenteeism rules to the limit. I would have loved to terminate her, but the details of her misfortunes and the seemingly limitless reach of our corporate sensitivity rules would make that very difficult and politically risky for me.

"Jim, have you read this memo? It says the company is setting aside summer internships for high school girls, daughters of employees. It's like 'Take Your Daughter to Work Day', but for the whole summer!"

"Yes, I've seen it. Why do you ask?" I inquired, although in my gut I already knew.

"My daughter, Theresa, is looking for a summer job. She can work here!"

"I don't know, Marsha. You can barely keep up with your duties right now. Your headaches have you in and out every other week. I don't see how shepherding around a schoolgirl is going to make getting anything done around here any easier."

She pouted in her extraordinarily sexy manner. That was the only other factor keeping her employed in my office's antechamber – at least when she did make it in to work: she was sure easy on the eyes. She stood before me in a short-skirted business suit, very smart, which highlighted her long legs and her ample chest. God! How I wished I could fuck her, but she'd never signaled any interest, and in my position, I would be a damn fool to initiate it on my own. All the looks in the world weren't going to make having her daughter underfoot all summer any easier, however.

"Jim, it says in the memo that our facility is authorized four slots. Can't you at least interview Theresa for one of them?"

I really had no way out, and I knew it. I agreed, hoping that at least four other employees would make similar requests so that I could select their daughters. If I had to have four teenage girls to baby-sit then the further they were from my day-to-day concerns, the better. I sent out an email of my own, encouraging ALL employees to consider the opportunity to vie for one of the spots.

-o0o-

Wouldn't you know it? A grand total of exactly four girls applied, including Theresa Jacobsen. The other three were applying to subdivisions, and were therefore the concern of my subordinates, but since Theresa was applying to intern with my personal assistant, I had to interview her myself. I held out some hope that I would find an excuse to deselect her from the program. Upon her arrival for the interview, I felt doubly compelled to do so.

I had seen Theresa precisely twice a year for the past three years - on "Take Your Daughter to Work Day", and at the annual company picnic. I had hardly noticed her before other than to observe that she was a cute girl who would someday be as hot as her mother. The afternoon of the interview, she looked like she had already made significant progress toward that result.

I guess I expected her to be wearing a miniature version of one of her mother's business suits, but instead she was dressed in the current manner of a fashionable teenaged girl. She wore a form-fitting gray silk top, with buttons down the front and a wide flair collar, which accentuated her thin waist – Jesus it looked like I could completely encircle it with my two hands! – and which stretched over the adorable little mounds of her developing breasts. They were no larger than lemons, but even through her top and the fabric of her bra I could detect the nubs of her pebbly nipples. As my dick twitched, I looked lower.

She also wore a very tight pair of black pants made, apparently, of some synthetic material which stretched over her adolescent hips, drew across her flat tummy, and passed snugly through the pronounced pelvic arch between her skinny thighs. At her ankles they flared out a bit, around her heavy-soled, chunky black shoes. My prick thickened as I forced myself to look up into her face to shake her hand, and then I quickly sat down behind my desk. This could really be trouble!

We chatted a bit, and I asked inane questions appropriate to filling an inane internship. What could a girl just finishing her sophomore year in high school have to say for herself, anyway? Mostly I concentrated on how fucking sexy I was finding this sixteen-year old girl. Her soft, heart-shaped face, her full pouty mouth, her big hazel eyes and her thick brown hair cascading down her shoulders were fantastic. Now I didn't feel particularly creepy about this – who wouldn't find such a thing attractive – but I did realize that should I hire her, I would be setting myself up for discomfort. Hell, I was already tormenting myself over her sexy mother – what would it be like having two of them around without any relief?

I was so distracted that I had to apologize and ask her to repeat the last thing she said.

"Oh, that's alright Mr. Ablerod – I said, 'If you're afraid I'm not smart enough, maybe you didn't know that I skipped a grade in middle school."

"You skipped a grade, Theresa?"

She smiled, not knowing where I was heading with this, misinterpreting it as a promising reiteration. "That's right, Mr. Ablerod, I skipped seventh grade because they said it would just be a waste of my time."

"So, although most of your classmates and friends are sixteen..."

"That's right, I'm fifteen. I don't turn sixteen for almost ten months!" she replied with an unwitting smile.

"I see," I replied, smiling myself. I said nothing more of it, and quickly concluded the interview, and then enjoyed the view of her juvenile bubblebutt as she let herself out of my office.

-o0o-

"I'm sorry Marsha, but she's only fifteen. The program documents clearly state that the internships are for girls aged sixteen to eighteen. I don't see where that leaves me any room."

"You don't understand how important this is to me, Jim! My husband left us five years ago. She sees him one weekend a month and two weeks in the summer, and he comes across like a god to her, squiring her around his fancy country club, taking her to his law office. This was going to be my chance to show her I could do something really neat like that for her. She is so looking forward to this – I already told her that with only four applicants, she was guaranteed to be hired. Please don't undermine my credibility, Jim!"

"You're asking me to take a great career risk. I don't like bending the rules, and I'd hate to do it for such a trivial cause. Really, Marsha!" She fidgeted in her chair.

"Please, Jim. What can I do to make the risk worth taking?" She got a desperate look in her eye, which was replaced with a sudden determination as she unbuttoned the top fastener of her blouse. "I've seen how you look at my breasts, Jim. Isn't there something we can do to get my daughter that job?"

-o0o-

Thirty minutes later, her eyes watering, Marsha was re-zipping my trousers and wiping some stray semen from the corner of her mouth with the back of her hand. Those naughty, bloated red lips of hers had finally found their way around my cock; just where I'd always thought they'd belonged.

Theresa had her summer internship, and I had an arrangement to receive this oral service from her mother a couple of times each week throughout the summer, to keep me from "discovering" our clerical error. The prospects looked good, and I had suddenly become an enthusiastic booster for "Take Your Daughter to Work Summer."

-o0o-

Theresa started on the first of June, and I was delighted to see she was wearing a little teenybopper miniskirt. She apologized for the casualness of the outfit, telling me that she intended to apply her first paycheck to some more professional garb, but I told her she looked fine. In fact, I decided to establish a "business casual" dress code for the entire facility to last through the summer months. Theresa beamed when I told her.

Naturally, the casual dress guidelines I promulgated were designed to allow the little heartbreaker great leeway. I was well aware from my occasional trips to the nearby mall that fifteen-year-old girls were capable of wearing the most provocative outfits without a second thought. With her mother now lined up to relieve any stress this might cause me, I was prepared to let her do her worst.

That evening, as Marsha and Theresa were collecting their things to drive home together, I called Marsha into my office, asking her to shut the door.

"What is it, Jim?" she asked.

"I think you know. I was running through some personnel records, and the new girl – you know, the intern working with you – there's something odd about her date of birth."

"Oh, I'm sure it's nothing. Let me look at it." She swayed toward me as she said this, arching her eyebrow.

"Take off your top," I commanded in an uncommonly husky voice. She paused for only a moment, and then slipped the white silk top off. She had no intention of pretending at innocence – she also took her bra off without any urging on my part. She then knelt between my spread knees and paid the tuition.

-o0o-

I don't know the reason for the special thrill of infidelity, but once I was getting some outside action, I found myself horny as hell at home with my wife, too. That night and many thereafter I spent throwing the Mrs. my bone, envisioning Marsha's magnificent chest and attentive lips.

-o0o-

Over the next few of weeks, everything was fine. After a while, however, a blowjob a couple of times a week became old hat. If you saw Marsha, you'd say I was crazy, but think about it: That wife or girlfriend of yours seemed like the last woman you'd ever need when you were trying to get in her pants, right? And then after you'd tagged it a few dozen times, your friend's date started really looking good, didn't she?

I tried to up the ante, and get her to fuck me. No go.

I used the mini-cam on my computer to surreptitiously snap some stills and a crude video clip or two of her choking down my seven-inch Johnson. That kept me amused for a while. But then that thrill faded as well.

And then I began thinking about Theresa.

-o0o-

The little teen started driving me crazy. I thought I'd loved her mother's very generous rack, but suddenly I found myself more transfixed by the fifteen-year-old's perky pair of junior volunteers. Also, I started finding ridiculous filing jobs for the young girl in my inner sanctum, just so I could enjoy the sweet swell of her cuddly rump as she bent to her task.

Whenever her mother dutifully sucked my cock, I'd no longer focus on her C-cup breasts. Hell, I'd hardly notice whether she took her top off or not. I'd instead stare into the middle distance and visualize Theresa's muffintops, for although she was underdeveloped, the tight blouses she'd wear never failed to accentuate the curves of her baby titties, or give clear evidence of her stiff, oversized nipples.

Now, when I drove my turgid rod into my wife of an evening, my mind's eye left both her and my "mouth mistress" behind, and pretended instead that it was fifteen-year-old Theresa on all fours below me. Oh, how I needed that sweet teen bottom!

-o0o-

After about a month of this, the inevitable happened and Marsha called in sick one Tuesday morning. Her migraine was back. Theresa arrived by bus, but asked if I could drive her home. I drove her home, and she nearly drove me to rape, statutory for sure, perhaps literal if necessary.

I agonized about the temptation, contemplated making a move on my underaged passenger, fantasized about taking her somewhere private and climbing all over her. But I didn't get to where I am today by being a fool, so I simply took my genital fury out on my wife's thirty-five-year-old box when I got home.

Which is also what I did Wednesday evening. And Thursday evening. Thankfully, on Friday Marsha returned to work. Since Theresa joined the other three interns on a "girls' night at the movies," I had Marsha all to myself. This time, I refused to take "no" for an answer. I fucked Marsha on the couch in my office. Then I fucked her again on my desk. Both times I thought of her daughter. Somehow, despite having finally knocked down the final wall of my assistant's resistance, the evening was unsatisfying.

-o0o-

So things continued as before, but now in addition to the blowjobs, I was taking the occasional dip in Marsha's mature but nonetheless gripping quim. Once I'd broken through that barrier, it wasn't hard to repeat. Marsha actually seemed to like it, although I spared very little energy on her pleasure. Over time, this cavalier attitude, combined perhaps with the humiliating circumstances, only served to pique my assistant's interest.

She became devoted and attentive to me in a way I'd never seen before. I took advantage of this by testing her limits. Soon, at my direction, she began coming to work panty-free. Then I insisted she use my phallically-suggestive productivity award from 2005 as a dildo, an act which I captured on my computer's video cam. And of course I made her lick the leavings of her copious gash-syrup from my prick after every zesty fuck.

But all of these things barely served to maintain my interest. They did manage to multiply my control over Marsha, but my heart wasn't really in it. My heart was where my prick wanted to be – deep in the loins of her underaged daughter.

-o0o-

Throughout the summer I had been taking greater and greater liberties with the fifteen-year-old intern. First there was the occasional "Honey," or "Sweetheart." Then came the casual contact –the hand avuncularly placed on the small of her back, the leaning over her slight form to strike a key on her computer while demonstrating something entirely unnecessary, and eventually patting her cute little rump with ridiculous frequency.

She seemed to like this attention, perhaps thinking it was a grown-up way to interact with the boss. In any case, she never objected, and often giggled, or flushed.

I, however, became more and more distracted. My days were constantly consumed with dreams of pushing it further. I fantasized about tickling her little cunt through the white cotton panties my rapt attention discovered she wore. I imagined chewing gently at the erect nipples that seemed to constantly thrust through the fabric of her schoolgirl tops. And I despaired at the denial of tasting the unsoiled treasure I just knew to lie between her slender thighs.

-o0o-

And then the same corporate rulebook and policy engine that had initially put me in this predicament, with its "Take Your Daughter to Work" nonsense, came to my rescue – or to my damnation, depending on how you look at it.

Marsha called in sick with her migraine again one Thursday morning, and I thought nothing of it, other than that I might get a chance to drive Theresa home again. Around noon, however, Sandy Clark, our facility HR coordinator, popped her head in and asked, "Do you have a minute?"

The long and the short of it is that our corporate policy on sick leave had finally put Marsha in the "up the creek" category. She was too far in the hole on sick days, and would start losing pay. Additionally, she could finally be dismissed, and it wouldn't be just up to me. Corporate headquarters would flag a case like this for investigation, just to ensure that I wasn't giving my assistant any special treatment. However, Sandy, always one to help out, had a solution.

"If she stays out thirty days straight, it qualifies as 'disability', and she gets full coverage. It will also then retroactively qualify fifteen of her sick days as disability, seeing how it's the same condition involved, right?"

"Right..." I answered cautiously.

"Well, you can save Marsha's job for her! The only problem is, can you do without an assistant for the next thirty days? If we have to replace her, she loses the spot, but can come back into a similar job here at this facility when she's 'better'. Of course, there is no similar job here that pays as well, so she'd have to take less money. She's the Top Guy's executive assistant, so any other assistant role is further down the chain, of course." Sandy smiled at her own mild flattery, and I smiled back, but for an entirely different reason. I had a plan.

"Let's give it a shot. You know Marsha's daughter, Theresa, has been interning with her this summer. If she can hold up the job for thirty days, her mother can keep the job when she gets back. Sound reasonable?"

"Sure, that could work, Jim. I know Marsha would be devastated if she lost this job. Has she ever told you about her ex?"

"Not really. As you might imagine, I try to keep my relationship with my assistant purely professional," I said without snickering. "Can you lay out the plan to Marsha, and then inform Theresa exactly how much is expected of her? I want her to know in no uncertain terms that if she can't fill in one-hundred percent for her mother over the next thirty days, I'll have to bring in a replacement."

"Sure thing, Jim. I think you're making the right call on this one."

My thinking exactly.

-o0o-

As I drove Theresa home that night, she was excited by the turn of events. Why wouldn't she be? Here she was, fifteen years old, being saddled with serious responsibilities and a very adult job. She just didn't know how adult I intended for it to become.

"I need to stress to you, Theresa, that this won't be fun and games," I said, as I turned off the freeway into her neighborhood. "There are a variety of tasks your mother is responsible for, ones that I'm sure she hasn't even tried to teach you. Many of them will seem demanding, maybe even surprising. It is important that they all be done well, so I don't have to find a real, permanent replacement for Marsha – I mean for your mom."

The young girl's face fell, and her hazel eyes widened. As we were sitting at a stop light around the corner of her house, I turned and looked right into their liquid depths. "Now, I'm going be to pulling for you and helping you wherever I can. I'll certainly try to teach you, and naturally I expect there to be a little bit of a learning curve. What I need from you is enthusiasm, effort, and, on occasion, obedience. Do you think you can manage that?" She nodded solemnly, and as the light changed I broke my gaze and drove on, letting her stew in that.

When we pulled up in front of her house, I had one more bit to add.

"Theresa, your mom is under a lot of stress about this development. Let's not give her anything else to worry about. As I'm sure you know, if it weren't for corporate headquarters, I'd let her take all the time off she needed.

"What I'm saying is, don't remind her about those more difficult duties she never trained you in. It will only worry her about your ability to succeed, or about putting you under too much stress. Let's not even mention their existence, maybe she won't even think about them. Okay?"

"Okay, Mr. Ablerod."

"Hey, that's another thing. You're not just an intern any more. You're my number one executive assistant, at least for the next thirty days. Call me Jim. And don't look so worried, or you'll worry your mom. I'm confident you can do it. In fact, I won't let you fail!"

She smiled at that, said "Thanks, Mr. A... , er, ... Jim," and turned to open her door. And I did something that had my heart in my throat.

"Wait a minute ... look at me." She turned. "Everything is going to turn out just fine." I leaned over, placing my hand against her head in a fatherly way, and pecked her on the forehead. She smiled, got out, and scampered up the walk. I went home and masturbated.

-o0o-

The next morning, Friday, young Theresa was full of energy and enthusiasm, proud and puffed up with her new, "real" and "important" role. I did everything I could to encourage this.

Around eleven o'clock, I handed her a list of certain female employees. "Theresa, this is one of those 'special' projects, the kind of thing your mother never trained you in. It is extremely sensitive, and only my number one assistant can be entrusted with it. Do you understand?"

"Yes, I understand, Mr ... Jim. Very sensitive."

"Right. I want you to work your way around the building here, not drawing attention to yourself. Find each of these women and mark down, on a scale of one to ten, their sex appeal. And don't let them guess at what you're doing."

"What? Their 'sex appeal'?" She naturally looked incredulous, the adorable pixie face scrunched up in confusion.

"Don't you know what that means?"

"Well, yeah, I know what it means, but why?"

"I'll have to explain that later, Theresa. It is very delicate, and very secret, and I don't have time right now for the details. Do you think you can rate them correctly?"

"Umm, well, I know which girls the boys at school like. And I know what the T.V. shows think is attractive. Is that what you mean?"

I made a point of looking concerned. "I guess that will have to do. This is exactly what I was afraid of. Your mother is mature enough to know how to do this. Of course, she never trained you for this – this requirement only comes down from headquarters once a year, so naturally she expected to handle it herself if it arose during this internship. Well, just give it your best shot."

She walked off with the file, a look of trepidation and curiosity on her face but not, I was happy to see, any sign of disbelief.

When she was gone, I made a call to an old college buddy to ask a simple, if curious, favor.

-o0o-

"I'm finished, Jim." She was finally getting comfortable with using my first name.

"Let me see," I said, and quickly scanned the list. She had placed a number next to every name, and she seemed to have done a pretty good job based on my own informal ratings, as if it really mattered. Among the "sevens" and "eights" I noted many of the young hotties who had often caught my eye. I had thrown in a couple of control cases, like the heavy Sandy from HR, and sure enough, my cute little assistant had graded her as a "three". Close enough, especially for a completely specious project.

"This is pretty good work. I don't know if it's good enough for corporate, but later we can go through it. I'm sure you would have done better on the men's list, but that comes around in the winter.

"Oh, I see you have a couple of nines and tens here. Sorry, forgot to tell you that the highest a girl can rate until she's been certified is 'eight.'"

"Certified?"

"Umm," I said, trying to look uncomfortable, "Yeah, I'll explain later. Basically, 'eights' are 'eights' until they're tested, then they might move up to a 'nine' or even a 'ten'."

She turned to go. I waited, and watched her yummy tail swing in its miniskirt as she headed for her outer office. Just as she was about to head through the door, I stopped her.

"Oh, your mom should be on that list. She was certified as a 'ten', but put an asterisk next to her name. That means she's out of commission. I hope that doesn't hurt her career. Oh, and put yourself down as an 'eight'. I don't think I could bring myself to certify you if they tell me to ... but maybe by putting that down we can buy your mom some time."

She nodded, but looked confused, then headed for her desk.

-o0o-

A couple of hours later, I called Theresa in and asked to sit down.

"I'm going to try to explain this to you, Theresa, and I hope you're not too young to understand, or to handle it like an adult. Can I count on you?"

She nodded. God was she cute!

"You know about sex, right? Good. And you also probably know that the general public thinks that in this day and age, a woman doesn't have to sleep her way to the top so to speak, right?"

"Well, sure, Jim. Of course not."

"Unfortunately, that is poppycock. The only thing that modern sensibilities have provided is that women executives now demand sexual favors from ambitious young men, as well. This is the very sensitive subject I've been alluding to. This sort of thing is so widespread that this firm, like many others, has actually created a formalized system, both to keep it under wraps and to try to make it as fair as possible. I am now in the position of having to teach you its inner workings. Your mother would be so unhappy if she knew you were aware of any of this, or of what she has had to do. Maybe I better not continue."

"But Jim, my mother and I don't have any secrets. I'm sure it's okay if I know."

"This is a secret she keeps from you, I'm sure. You see, she doesn't want to dash your youthful naiveté. She wants you to believe that the world works the way it should – the way both she and I wish it did. No, she'll be very unhappy if you learn about this, and she'll be very angry with me. I can't chance it."

"Jim, won't this be bad for mom's job? I mean, if I can't help you with these duties?"

Good girl. "Well, yes, but there's nothing for it. Damn this company! There's nothing I can do, but this is just too much."

"Jim, I swear I'll never let my mom know I know. I swear ... I can't let her down. Keeping up appearances here is for her own good, so please, tell me, and I'll keep it a secret."

"Well, alright. But if your mom finds out I let you in on this, we're both cooked!"

-o0o-

" ... So you see, Theresa, every facility like this one has to provide at least one certified woman to corporate per year. They don't always get called upon to perform at headquarters, but we have to have at least one ready.""

"And what's the certification again, exactly?"

"Every 'eight' is eligible to be tested. If, upon receiving the list – you know, the list you completed for me today – if upon receiving the list, headquarters is thinking about a particular person for advancement, and she's an 'eight', they call and tell me she needs to be certified. I can't put it any other way. I have to make love to the girl. If she's not very good, she stays an 'eight' and is considered 'uncertified' – which is unfortunately not good for her career. If she's pretty good, she's certified as a 'nine'. If she's very good at sex, she's a 'ten', and she can go a long way in the organization. I know, it's primitive, and disgusting, but that's the way it works. Since there are a lot fewer female executives, it's a lot easier on the men, but that is changing, too. Nowadays, I'd probably have to go through the same thing just to get this job that I have.

I looked into the schoolgirl's face intently. She seemed to be buying it, but clearly some aspect was troubling her. "Is something the matter?"

"You said mom was a 'ten'..."

"Yes, that's right. I was forced to certify her myself. Not that it was that bad!" I added with a smile. "You see, this is why I was afraid to tell you about all of this. Clearly, your mother can never know that you know."

"Jim, don't take this the wrong way, but there's no way mom would do that."

"Theresa, this is very important. If you don't believe me, I'm afraid you won't take the gravity of this seriously. You might say something to your mother, and she will be furious with me. She'll probably blow a gasket with headquarters, and ruin her career, too.

"To protect her, and to make sure you respect this secret by not letting her know that you know, I want you to watch something. They make us record our certifications, and submit a video, like this one."

I'd been busy over the past couple of hours. As the innocent teen stared at my computer screen in disbelief, a montage of the crude video clips and stills I'd collected over the last few months played before her. She saw her mother, in no uncertain terms, swallowing my cock, getting fucked by my sturdy rod in various positions, and even shoving my 2005 productivity award into her own greasy gulch.

Theresa's face turned bright red as she watched, but she made no move to avert her saucer-wide eyes. Her breathing became audible. She didn't flinch when I placed my hand on her shoulder and muttered something like "I'm so sorry you have to see this," and she didn't notice as I craned my neck to watch her precious little titties heaving in distress.