Sexual Harassment Training

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Boss lady gives her young assistant hands on training.
8.7k words
4.72
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Part 1 of the 2 part series

Updated 07/04/2023
Created 04/18/2022
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Tyler and Jacob were both laughing as they walked into what appeared to be an empty breakroom for a cup of coffee. They had just completed the company's new 'Sexual Harassment in the Workplace' seminar.

They both had enjoyed the interruption of their day, the mandatory quarterly training sessions always broke up the monotony of the daily grind. But though both young men enjoyed the break in their routine, they also found this particular training to be a waste of their time, as neither of them were in any position to use sex as leverage in the corporate world. But they had fun with it anyway.

They had sat in the back of the large room and made snide comments under their breath, like a couple of high school kids, barely paying attention to the session. And they were still joking about it as they made their coffee in what they assumed was an empty breakroom.

Jacob was in his first year with the company, and a clerk in the mailroom. He was average height and a tad overweight. He was not ugly, but certainly unremarkable in his looks. In fact, if it wasn't for his borderline insolent personality he would have been easily forgotten.

Tyler was hired only six months before Jacob, and was an assistant to the assistant for one of the vice presidents. So he was basically a 'gopher'. He was the guy who always got sent to go for this, or go for that. He spent a lot of time compiling data and doing research. Schlep work, he called it. But it was a foot in the door of a respectable company, and the largest employer in the area.

He had played basketball and baseball in high school and had kept up with his love for sports by playing basketball for the small college he'd gone to. He also joined leagues around town, both basketball and frisbee, and was considering joining the company softball team.

So he was physically fit, and at six feet tall and with curly blond hair, Tyler was the more attractive of the two. His blue eyes and strong chin garnered him his share of attention from the women in the company, unlike his friend.

He had had a brief fling with a woman from the legal department, and it had ended rather amiably. The sex had been great, but they really didn't have anything else in common, so they broke it off, with hints that maybe they could get together occasionally for some carnal fun.

And while that hadn't happened yet, he noticed that some of her friends were a bit more friendly after his relationship with her, and he wondered if he hadn't gotten some free advertising.

He was enjoying the extra flirting and was appreciative of it, no matter what sparked it. He had hopes of getting at least one of those girls in the sack.

But the one female in the company who never seemed to notice him was the vice president of Tyler's department. She was a very sexy woman in her mid forties. Tyler knew she had never been married, but had a daughter who was only a few years younger than himself.

Although she was gorgeous, she had a very stern, even intimidating demeanor, and was rarely seen smiling. Tyler always assumed that she had to carry herself that way in order to be taken seriously in a male dominated profession, as not many women had managed to break the glass ceiling that early in the 1980's

And being a gopher in her department meant that Tyler had to do her grunt work, even the mundane personal tasks that she couldn't be bothered with. But he didn't mind it at all when he had to get her a cup of coffee, or pick up her dry cleaning, Or go over one of his reports with her.

He usually got a peek at her legs as she sat in her desk chair, her skirt pulled tight as she sat cross legged at her huge desk. The hem almost raising enough to reveal whether she was wearing stockings or pantyhose, but not quite. Sometimes he even caught a glimpse down her top at the frilly bras she wore.

Barbara Garbino, despite her no nonsense attitude, was, at least to Tyler, one of the hottest women in the company. She was a petite woman, but her high heels and perfect posture, added to her serious air, made her seem almost statuesque.

A luscious set of B cup tits were always on display by her erect posture and the stylish, tailored business suits she wore. Her form fitting outfits also accentuated her narrow waist and wide, womanly hips, and an ass that Tyler lusted for daily. She also had a set of legs that many younger women would kill for. Firm thighs and rounded calves that flexed tantalizingly as she strutted around the office.

And as if her smoking hot body wasn't enough, she had the classic mediterranean features of an olive complexion, big, dark eyes, high cheekbones, and wide, full lips. She wore her hair stylishly short, exposing her sensuous neck.

"I mean, seriously, what am I going to do, withhold the interoffice mail from Mary down in legal if she doesn't give me a blowjob?!" Jacob asked with a laugh, bringing Tyler back to the breakroom.

Tyler laughed along with his friend and added, "I would think if anyone was going to be sexually harrassed it would be us! But would it count as harrassment if we enjoyed it?" He asked, wiggling his eyebrows in his best Groucho Marx impression.

"I know what you're thinking," Jacob said with a lewd grin, "You're just hoping old Barbie baby will make you perform sexual favors for her someday, to help you advance your career!"

"Fuck my career!" Tyler blurted, "She's so sexy, I would perform sexual favors for her, for free, in a heartbeat! I would eat her sweet pussy until she creamed my face!"

"Hell yeah man, and I would have to check out that killer ass of hers!" Jacob chimed in, "Imagine how it jiggles when she takes it doggie style!" He held his hands out as if he was holding a woman's hips while he thrust his own. "You think ol' Barbie takes it in that fine ass of hers?"

Their laughter, and in fact the entire conversation, ended abruptly at the squeak of the ladies room door, just beside the coffee counter. Both men gawked, like deer in the headlights, at the site of Barbara Garbino standing just a few feet away, drying her hands on a paper towel.

Barbara watched her hands work intently, not even acknowledging the presence of Tyler and Jacob, who quickly went back to pouring coffee, grabbing creamer, anything to avoid looking at the older, intimidating beauty. They both realized that she had heard every word they had said. They both wondered if she could hear their hearts beating.

Barbara finished drying her hands, and as she was throwing her paper towel into the can, she finally spoke. "Hello Jacob." She said casually.

Jacob managed a mumbled, "Hell, hello Barbara." His face beat red, and quickly looked away again.

"Tyler, I would like to see you in my office at the end of the day." Barbara continued, just as casually, but in her usual business like manner. Her eyes were locked on Tyler's, and he was afraid to look away. He was afraid of looking as guilty as he felt.

Tyler tried to sound just as casual yet professional as he replied, "You got it Barbara." He tried to read her face. She always looked so serious, and the look he saw then was no different. She was as stoic as ever, if not slightly more intense.

With that she strode from the room. Both men afraid to let their eyes follow the clicking sound of her heels on the tile floor, as they normally would have.

As the sound of her heels faded down the hall, Jacob moaned, "Holy fuck!" He mimicked banging his head on the counter.

"Fuck man, I am done!" Tyler said in a strangled voice. "She is going to talk to H. R. and I will be gone!"

"You?" Jacob exclaimed, "She had to have heard me too!" Then he pondered aloud, "Wait, why wait for end of day? Why didn't she shit can us both right now?!"

"Because she wants us to suffer the rest of the day. She wants to torture us." Tyler lamented. "Fuck man, I have a car payment, rent...."

"Shit man, we all have bills to pay." Jacob added. "But seriously, I think if she was going to fire us, she would have done it right here, right now. She's a no nonsense woman man, she doesn't fuck around!" Jacob reasoned.

"Fuck, I don't know man." Tyler said, "All I know is that I have to get to my desk and get some work done. I don't need to be slacking off on top of everything else."

The training had been held right after lunch, and had lasted a little over an hour. So Tyler only had to suffer a few hours, but they turned out to be the longest hours of his life. He couldn't stop going over the events in the breakroom in his mind.

He couldn't believe he had been that stupid! He couldn't believe he had said aloud the things he had said! He found some consolation in the fact that the things that Jacob had said were way worse than what Barbara had surely heard him say. At least in his own mind.

But, he realized, if he got fired, none of that would matter. He tried to hold onto the theory that Jacob had come up with, that if Barbara was going to fire him, she would have done so already.

He remembered that look she had given him, he tried to decipher what he had seen in her eyes. She had not seemed angry, but it was certainly a very intense look. Yet she was always so in control, that he couldn't be sure.

But Tyler still couldn't let go of his premonition of impending doom. And that brought his mind right back to the things they had said, and what Barbara surely had heard.

Finally the clock on the wall indicated that the day was over, for most of the employees anyway. Tyler took his time closing down his computer and organizing the barely touched work on his desk.

He wanted his coworkers gone before he went to Barbara's office, in case she was finally going to drop her self control and ream him out good. He didn't want the whole department to hear him get fired.

Most notably, he wanted Alice to leave. Alice was Barbara's assistant, and as such, her desk was just outside of Barbara's office. She was a sweet, motherly type of woman, and was Tyler's direct supervisor. She was teaching him the ropes, and Tyler didn't want Alice, of all people, to know of his crimes.

Finally Alice said goodnight and threw her purse over her shoulder on her way to the elevator. With most of the other desks in their section vacated, Tyler knew he couldn't put it off any longer. He knocked softly as he poked his head in the door. Barbara was sitting behind her large desk, the skyline of the city visible through the huge window behind her. "You wanted to see me Barbara?" Tyler asked timidly.

"Yes, come in Tyler." Her tone wasn't angry. Tyler thought she actually sounded friendly. He started into the huge office, his nerves on edge. He made a few steps into the room when she looked up and said "Please close the door Tyler,"

Tyler stopped and muttered, "Oh, yeah, sure Barbara. " He turned to close the door, and as it clicked shut she told him "Lock it too, Tyler." Her voice sounded softer that time. And after he pushed the button in the handle, he turned to face her again. She was standing now, her hands on the desk, leaning forward slightly. She looked as sexy, yet intimidating as ever.

She gestured towards the chairs at the front of her desk and said, "Please have a seat." Her voice was definitely softer now, he was sure of it. As he moved to the chair, he noticed she had removed her blazer since he'd seen her in the breakroom earlier, and was there an extra button undone on her blouse?

As Tyler took a seat, Barb went to a credenza across the room. Her usual confident stride seemed more fluid to Tyler, more sensual. He watched her legs flex and hips roll as she walked. She opened the bottom cabinet door and leaned forward to retrieve something from deep inside.

Tyler could not help but take in the site of her ass stretching the fabric of her skirt. The skirt had pulled up enough to give him a glimpse of the frilly band at the top of what was apparently thigh high stockings through the small slit in the back.

Tyler was shocked, but very pleased with the enticing view. He'd been wondering for months about her preference for lingerie. Ever since he'd been transferred unexpectedly to her department.

He felt his cock stir as he thought that if he was going to be fired, at least he would have a great memory of the event. He knew he would be reminiscing about it as he masturbated for years to come.

He could imagine a few scenarios with her in that position, some involved the acts Jacob had described earlier, others involved him on his knees, doing what he had described.

Tyler heard some glass tinkling and Barbara stood up with a bottle of very expensive scotch and two tumblers. "Do you like scotch Tyler?" She asked as she walked over to the chairs where he sat, trying to hide his burgeoning erection.

"Sure!" He said, not believing how this was going. "I don't usually drink it, but I do enjoy it."

Barb handed him a glass and poured two fingers for him, before pouring herself some and setting the bottle on her desk. She sat in the chair at a slight angle to his and crossed her legs. Tyler struggled to maintain eye contact with her, and not look down at those legs.

"I understand, I know you don't make much money yet. But if you play your cards right..... You know Alice will be retiring next year? It would be a smooth transition for you to move up into her spot." Barbara asked.

Tyler was shocked, but tried his best to maintain his cool. He had been certain that he was about to be let go, and now Barbara was sharing her top shelf scotch with him, and talking about a promotion, to be her personal assistant no less!

"I know she's retiring, she talks about it all the time. She wants to spend time with her grandchildren. She was just saying yesterday that her granddaughter would be old enough to learn to knit soon." Tyler answered with a forced chuckle. "But I would have thought that you would be replacing her with someone with more time with the company." He replied.

Barb commented, "Well, you are already working with her, you know the position. And as I said, it would be a smooth transition." She took a sip of her drink and added, "And i don't have to replace her with seniority in mind, I can hire who I want."

She took another sip of her scotch, and Tyler followed her lead as he tried to act cool and think of a reply. The expensive whiskey burned smoothly as it went down, distracting his thoughts.

Before he could say anything, she continued, "Of course I believe we have something else to discuss first."

"Oh shit!" Tyler thought, "Here it comes." He knew the meeting was going too well, he cursed himself for falling into her trap. He took another sip of his whiskey to steel himself for what was coming. It seemed to calm him as he felt the warming effects.

"I got the impression today that you and Jacob didn't get the whole picture of the sexual harassment thing. You seem to think that you are immune from being involved in anything like that." Barb said, holding his gaze.

Tyler fidgeted, searching for something to say, "Uhm, well, we, uhm..." Barb actually smiled then, it was more of a smirk actually, and it was unnerving to Tyler, he could see her enjoying his discomfort.

"You two seemed to be under the impression that you had to have some sort of power over someone else to be able to sexually harass them. But apparently you missed the part that said it could even be inappropriate comments that make another person uncomfortable." Barb explained patiently.

"For instance," She continued, "talking about fucking a woman doggie style and making her ass jiggle with each hard thrust, while said woman is in earshot. If the woman in question was offended, or in some way felt objectified, then that would count as sexual harrassment as well."

Tyler was speechless, he had never heard Barbara swear, let alone casually talk about sex. He sat, wide eyed, mouth agape, wondering if he should try to apologize or just stay silent. Finally he muttered, "I see." Before finishing his scotch. It went down easily, with less burn, but Tyler hardly noticed.

Barbara quickly poured him some more before continuing. "Or for instance, if you were to say something about eating a woman's sweet pussy, until she creamed all over your face, some women would be offended by that!"

Tyler was again speechless, he nervously took another sip of his drink and just sat there, trying to control his breathing. He was completely thrown off by Barbara's demeanor, she was conversational, when he had expected anger. He couldn't think of a single thing to say in reply.

"Are you following me Tyler?" Barb asked patiently. "Do you understand what I'm saying? That anything sexually related that could make a person uncomfortable, or objectified can be construed as sexual harassment?"

"Uhhh, yeah, er, yes Barbara, I understand." Tyler swallowed hard and continued, "I'm sorry, we didn't mean anything by it, we were just, like, kidding around." It all came out in a rush, he was almost relieved to get to the subject that had haunted him all afternoon.

As Tyler finished, he took another sip of the top shelf scotch, and Barb joined him, then added more to each glass. She had uncrossed her legs to pour for Tyler, only this time she never crossed them again, she leaned back in her chair with her knees slightly apart, as if daring Tyler to look.

"I understand that guys talk about women, hell, you should hear some of the things that we say when there's no men around!" Barbara offered with a chuckle.

"As a matter of fact," She went on in a hushed, conspiratorial voice, "You should have heard what I heard Cindy from Legal telling her friends in the breakroom one day." She added, looking directly at the bulge in his pants. Even flaccid, there was no doubt where his prick was inside his khakis.

"She was bragging about her lover's great cock, and his oral talents." Barbara continued with a lewd grin. "It's amazing how much great information I get from the breakroom ladies room!"

Tyler fidgeted and took another sip of his scotch. He remembered wondering if Cindy had been talking to her friends about him, and he realized that was all just before he had been unexpectedly transferred to Barbara's department.

He took another sip of the best damn whiskey he'd ever tasted. It really was very good, and going down rather well. Tyler knew he had better be careful, he was still confused by the way things were going, and he could feel the beginning effects of the whiskey.

"Yeah, that's all it was, we were just talking, just kidding around." Tyler reiterated.

Tyler strained to maintain eye contact with Barbara, but in his peripheral vision he saw her hand running slowly up her black nylon clad leg. Her fingers extended down to the inside of her firm thigh. It was as if she was encouraging him to look.

She stopped just shy of the hem of her skirt and resumed the conversation. "I see, so to clarify, you don't think I am sexy?"

"Uhh, what? Excuse me?" Tyler sputtered. He couldn't begin to think of a reply. He just wanted to disappear and wake up in his bed and realize it was all a dream. A bad dream.

"So fucking sexy, I believe was the phrase you used." She added, "That you would gladly perform sexual favors for me, until I creamed your face. I believe that's what you said." She added, "And I believe you said that you would do it for free, with no regard for your career."

"Oh, uhm, well...." Tyler was shocked yet again by how this was going, and was still at a loss for words. He certainly couldn't admit to her face what he felt. He still couldn't figure out if he was in trouble or not.

Barb jumped in and asked, "Are you alright Tyler? Is this conversation making you uncomfortable?"

"Uhh, well, a little bit. I wasn't really expecting that...." He paused, trying not to say the wrong thing. "...that question." He sipped his drink, taking advantage of the break in eye contact to look at her manicured nails stroking the inside of her thigh, with the dark cavern of her skirt just beyond.