Sexual Harassment Training Ch. 02

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Tyler is tested. Earns a reward.
10.8k words
4.68
5.3k
4

Part 2 of the 2 part series

Updated 07/04/2023
Created 04/18/2022
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This chapter became longer than intended (like they always seem to), because I felt like I needed to convey Tyler's torment.

But fear not dear reader, he will be rewarded ;->

I also struggled with the category, hopefully I chose the right one. I credit Djmac1031 for help with that. I appreciate having a sounding board, thanks DJ.

Feel free to leave a comment.

Tyler sat at his desk, foot tapping nervously, watching the clock, and running spell check on a report he had just finished. The number of mistakes were astounding, but he wasn't surprised.

His mind wasn't focused on work. He was so distracted by the memories of his meeting with his boss the day before, and the fact that he needed to cum so bad, that he couldn't think straight.

His boss, Barbara Garbino, was, in Tyler's mind at least, the sexiest woman in the building, despite the fact that she was so much older than Tyler. And there were a lot of sexy women employed by his company.

Barb had overheard Tyler and his buddy Jacob talking about her the day before. And it had been a rather lewd conversation. Barb had not acknowledged what she'd heard at all, but had ordered Tyler to be in her office at the end of the day.

What transpired during that visit had been so crazy that nobody would ever believe it. Not that he could tell anyone. Barb had been very explicit about that.

In fact, she had given him two distinct orders. He was not allowed to tell anyone anything about what went on, especially Jacob, and he was not allowed to cum.

The first directive was easy enough to follow, as he knew how unbelievable it was. The whole event played out like a scene from some amateur, online, erotic literature website.

But the second decree, the one that denied Tyler a much needed orgasm, that one was damn near impossible to follow.

But he had made it. He had gone home after being dismissed from Barb's office with a raging erection. It had been a rather uncomfortable commute, with his thick seven inches straining against his khakis, oozing precum the whole time.

The fact that Barbara had kept his boxers meant that he had nothing to stop the obvious wet spot in his light colored pants. As if the bulge wouldn't have been noticeable enough on it's own.

In fact, as soon as he'd left her office, he had encountered the cleaning lady or girl, as she was younger than Tyler, emptying the trash at his desk. She had noticed his situation immediately, and her face brightened with lusty glee at the sight.

Her name was Gabriella and she was a smoking hot Latina immigrant. She was a petite girl, with a thick ass, narrow waist and big tits. She had an angelic face with thick lips that stretched wide to show her gleaming white teeth when she smiled.

Tyler had spoken to her before, and there had been some mild flirting, despite her badly broken English. She had always seemed like she would be game for some sort of sexy fun.

So when her eyes lit up at the sight of Tyler's obvious display, he wanted nothing more than to take her, right there in his cubicle. He needed to cum so bad that his brain worked out a dozen things he could do with her in a matter of seconds.

The fact that he was more than a little drunk from Barb's expensive Scotch, and hornier than he had ever been in his life made it difficult to restrain himself.

Coupled with the fact that Gabriella was staring hungrily at his cock, with the growing wet spot on top, and the only thing that stopped him was Barb's voice in his head telling him, "You will not cum now. Nor will you cum at home tonight, or tomorrow morning. You will not cum until you return to this office at the end of the day tomorrow! Do you understand?"

Tyler forced his foggy brain to dismiss the lewd urges he was experiencing and get the hell out of there. He knew that he had agreed to follow Barb's orders, and to violate them with the sexy housekeeper, on his desk, just down the hall from Barb's office, would mean two things. He would be fired, and he would never get the chance to fuck Barbara Garbino.

The smell of Barb's pussy on his face was enough of a reminder of how bad he wanted to fuck her. He could still hear her moans and dirty talk in his mind, and he now wanted more than ever to fuck her. The opportunity to enjoy some sexy Latina was not enough to sway him from that, no matter how much he wanted to.

He had gathered his things and hurried from the building, holding his suitcoat in front of his crotch the whole way to the parking lot. Luckily most of the employees had left for the day, and the only person he encountered was Carrie, the parking attendant.

Of course that didn't help either, as she was a tall, pretty, blonde. He knew that she could see straight down to his lap from her perch in her booth. She was always exceptionally friendly, and Tyler had always wondered what she looked like without her uniform.

The view into his car that day had certainly seemed to affect her, as she didn't say much, but simply stared at his cock, until she looked up to meet his eyes with a wistful look on her pretty face.

Tyler fought off the dirty thoughts that threatened to invade his head, and pulled out into traffic without even looking, nearly causing an accident.

The drive home was filled with the memories of the day. There was the Sexual Harassment In The Workplace training that was required for all employees. He had sat in the back of the room with his buddy Jacob, acting like a couple of high school kids, and enjoying the break from the routine.

Then the totally inappropriate conversation they'd had in the break room. Which was suddenly interrupted by the appearance of the exact woman they were talking about.

Tyler remembered the look on Barbara's face as she told him to come to her office at the end of the day. He couldn't begin to decipher her gaze. Barbara had kept her demeanor completely void of emotion.

And as she was always so poised and authoritative, she always came across as cold and stern. So naturally, Tyler had assumed the worst.

He had worried that he was going to be fired. He had gone through a thousand scenarios of how it would play out. But none of them came close to what had actually transpired.

Taylor's mind flitted through the events the whole way home. Interrupted only by the traffic lights, which always seemed to place him in a lane right next to another pretty woman, which didn't help his state of mind at all.

He remembered the way Barb had practically sauntered to her credenza and bent over to retrieve the good Scotch whiskey and two glasses.

When she bent over, the sight answered the question of whether she wore stockings or pantyhose, and the sight of bare flesh gave Tyler the first hint of an erection that would last longer than he thought possible.

He'd expected to be fired, and was actually offered a promotion. Besides that, Barb had gotten him to admit that he'd meant what he said when she overheard him say he'd love to eat her pussy.

There had been a rather lascivious recap of the finer points of sexual harassment. And Tyler learned that Barbara had no issues with the use of foul words, and hearing her sexy voice say those words had been so fucking hot.

He stopped for a red light and saw a voluptuous redhead in the next lane, applying a deep red lipstick with the aid of her rear view mirror. Tyler's cock lurched in his pants at the thought of what he could do with her lips.

And that reminded him of Barb's story of sucking off her boss, right there in the very office they were in. She was very descriptive, and she admitted shamelessly how much she loved sucking dick, all the while plying Tyler with her expensive whiskey.

Her manicured nails had crept up her shapely legs as she talked in a husky voice about her love of sucking cock, and gazed at Tyler's growing erection in his pants. He wanted to rub his cock so bad. But was afraid to.

Eventually, as Barbara's story went on, she had worked her hand far enough to reveal the tops of her stockings, and she began to massage her pussy.

Her tale went on to explain how her blowjob had evolved into a mouthfuck, and how she'd loved every second of it. She described how her former boss had used her mouth almost gently for his pleasure.

Occasionally he tested her gag reflex, but she hadn't learned to deepthroat, yet. She confessed that that would come later.

Somewhere along the way, Tyler had begun to rub his cock through his pants, and Barb watched him closely as she told of how much cum the man shot into her mouth, and how he told her that she was a good girl. He also told her that she'd cemented her position in the company, and their liaisons had continued for years.

A traffic light turned yellow, and Tyler made a quick decision to stop. His initial instinct was to floor it and beat the light, but that would mean he'd be home that much sooner, and that would mean more time resisting the urge to masturbate.

He also knew that he was easily over the limit for alcohol in his system, and he certainly didn't want to get pulled over and get arrested.

When he came to a stop he looked over as a jeep pulled up next to him. With the rag top and doors removed, Tyler had a perfect view of the driver. She looked to be around his own age, with long, wavy, blonde hair.

She had a thin, white tank top on with a black bra underneath. The result was that her big tits seemed highlighted, like she was advertising them.

She was wearing a pair of jeans cut off very short, showing her deeply tanned, smooth legs. She was drop dead gorgeous, and looked like she had just walked off a sun kissed California beach.

With her jeep sitting up high and Tyler's car sitting low, he had a perfect view straight across to those legs. He didn't realize he was staring at her, or that he was rubbing his overly primed dick, until she looked down and caught him.

She called him a pervert, just as the light turned green. She popped the clutch and sped away, leaving Tyler behind, feeling ashamed, yet still highly aroused.

His initial thought was to catch her and apologize. To explain his situation, and that he was really not a pervert, that he was really a nice guy.

But he knew she would think he was stalking her, and that she would never believe his explanation anyway. And then there was Barb's explicit instructions to never tell anyone anything about what went on in her office.

So when the car behind Tyler honked their horn, he sighed in frustration and pulled out, heading home to a cold shower, and a long night of frustration.

Tyler's memories flooded his mind again almost as soon as he started moving. He remembered Barb hiking up her skirt and masturbating as she went over the difference between harassment and consensual sex.

She pointed out that when she had blown her boss she hadn't felt harassed at all, in fact she had loved it. And it had definitely helped her career

When she had made the comparison to Tyler's potential advancement along with his desire to eat her pussy, she had spread her legs and offered herself to him.

Tyler had wasted no time dropping to his knees. He had been so close to her pussy at one point, that he could smell it, and he'd wanted so badly to taste her.

But she stopped him, and set the first ground rule, that of complete secrecy, with the threat of dismissal and the ruining of his career if word got out.

Then she added that she wanted to see his cock. She made him stand in front of her and strip off all his clothes while she watched, fingering herself the whole time.

Barb had obviously liked what she saw, telling him that she thought he was sexy, and making small talk about his physical activities. He was frustrated by her delays and went along with her instructions, hoping to get back between her legs.

Looking back on it, Tyler had to admit to himself that stripping naked in front of Barbara, and standing there in her office while she sat fully dressed, and scrutinizing his nude body, had been strangely exciting.

Barb had gotten him to confess that he masturbated while thinking about her, and she directed him to demonstrate. He had begun to jack off for her, while she played with herself and talked dirty to him about it.

When she asked him to show her how he would fuck her hard, he had gone all out, stroking himself like a madman.

But just as he was on the verge of shooting his load all over her, Barb had stopped him. Tyler could still feel her manicured nails digging into his wrist as she made him let go of his prick. He took his eyes off the road long enough to verify that Barb had actually left marks on his wrist.

He had been so close, and when he released himself, his cock was swollen purple and bobbing in the air with every beat of his heart.

A massive dollop of precum oozed from the tip, and she slurped it up quickly, but her mouth was gone before he could think about it, adding to his frustration.

Tyler saw the turn off for his street at the last possible second. He had to brake hard and whip the wheel over to make his turn. The driver behind him hit their brakes and laid on the horn.

As Tyler made the corner he looked in his rear view mirror and saw a cute woman with light brown bangs flipping him the finger, and saw that she was yelling something. Tyler was not a lip reader, but he easily recognized the word FUCK being used.

It made him think about Barb, and how she'd told him that it was going to be so good when they fucked. She sounded so very sultry and horny when she said it, that Tyler had wanted to pound her right then and there.

Finally Tyler made it home. He found a spot in the parking lot of his apartment complex, and realized that for the first time since moving in, he was going to hate having to walk past the community swimming pool to access his hallway.

His apartment complex was near the state university, and as a result, there were lots of college students who lived there. Many of whom took full advantage of the swimming pool. Which meant that Tyler always got an eyeful of nubile young women in bikinis, dripping wet or oiled up, hanging around the pool area.

Normally, Tyler relished it. He always made a point of chatting and flirting with any of the girls he saw there, and had gotten to know a few of them by name.

But that day he dreaded the thought of seeing nearly naked women. He was afraid of cumming in his pants and making a fool of himself. He kept his head down and his suit jacket in front of his cock as he quickly walked towards the building.

He almost made it to the door when he heard a familiar voice call out, "Hey Tyler, what's up? Not speaking to us today?"

He knew before he looked that it was Sherri. He knew he shouldn't look back, but couldn't help himself. He couldn't bring himself to be rude to a girl that was so sexy and flirtatious. He had to adhere to Barb's orders, but that didn't mean he had to burn bridges.

Keeping his hand to his belly, with his jacket hanging down to hide his still hard dick, he looked over his shoulder and said, "Hey Sherri, sorry, but I'm not really feeling well."

He was going to add that he thought he had caught a bug, but when he saw her, his mind just shut off. She was wearing a tiny bikini that he'd never seen before. It was white and perfectly highlighted her deeply tanned and curvaceous body.

"Sorry to hear that, I was hoping to get your opinion on my new swimsuit!" She answered as he gawked at her.

She had just emerged from the pool and her brown hair was dripping water down on her abundant cleavage. He saw right away that the wet top was nearly transparent, and her thick nipples were on display.

As his eyes traveled down over her ever so slightly plump stomach and beyond, he realized that she had a small triangle of fabric covering just enough to keep her from getting arrested, with strings running around her thick hips. Then he noticed that it was the same fabric as the top, and he could see the hint of her triangle of pubes.

Tyler heard a giggle, and looked to Sherri's left to see Alisha, a slender black beauty that was going to college on a scholarship for track and field. She had the powerful legs of a runner and the tightest looking ass Tyler had ever seen.

"He might not be feeling well Sherri, but I'd say the look on his face says he likes your suit just fine!" Alisha said in her sexy southern drawl, her pretty black face lit up with her huge smile.

Tyler noticed that Alisha was wearing a bright yellow bikini that also accentuated her dark skin. She came up to the fence alongside her roommate and Tyler took in her tiny waist and small tits.

She appeared skinny next to Sherri, who wasn't fat, but pleasantly rounded, and thick in all the places that counted.

Tyler had been chatting these two ladies up since he moved into the complex, and felt sure that he was going to score with one or the other eventually.

But his dream was to bed them both, together. And the first time that idea had occurred to him, he'd been jacking off, and when he thought about what it would be like, he literally shot himself in the face with jizz.

So when he saw them that day, in the state he was in, his prick lurched in his pants and he knew he had to pull himself away from them, or he'd never be able to uphold the rule that Barbara had set for him.

"Wow!" Tyler gasped. "You look, you both look... incredible!" He almost fondled his aching dick through his pants again, like he did when he saw the hot girl in the jeep. But caught himself, and the result was that he appeared to be rubbing his belly.

"Look girls," He told them. "I'd like nothing more than to go change into my trunks and join you. But I really have to go!" And with that he turned and bolted into the building, leaving the two women behind.

Tyler dashed up the stairs to his apartment and fumbled with the key, his raging hormones and the quality Scotch whiskey working against him. Once inside he locked the door behind him and finally pulled his suitcoat away from his body.

He was amazed by the size of the stain in his pants. It looked like he had spilled a drink on himself. He noticed that the stain had even gotten through the pants into the jacket he'd hidden it with.

He cast the jacket aside, he knew it would need dry cleaned, and he was definitely not leaving his apartment until morning.

He stripped off the rest of his clothes on his way to the bathroom. He needed a shower, as cold as he could stand it. But he knew he would need to be careful. He felt like his cock had a hair trigger, and if he tried to wash it too much, Barb's second rule would be broken.

When he peeled his pants off, he was equally aroused and disgusted by the mess he'd made. He never knew how much precum a man could produce.

He struggled with the urge to grasp his swollen prick. It was harder than he could ever remember, and practically pulsing with his heartbeat.

He managed to get through his shower without cumming, but it was close when he washed off all the precum. He had focused on his basketball schedule for the coming week while quickly soaping up the area and rinsing in cold water.

The rest of the evening went by with Tyler staying focused on making dinner and eating. Followed by the most boring documentary he could find on the public broadcasting channel.

His dick even managed to go down at one point, and he went to bed still struggling to think about anything but Barb, or Gabriella, or Sherri and Alisha for that matter. Not to mention the other attractive women he'd seen on the way home.

His sleep that night was restless and filled with erotic dreams. When he awoke, his foggy brain had him taking Barbara on her huge desk. She was howling, "Fuck me Tyler! Fuck me with that big cock!"

As he became conscious, he realized that he was jacking off and on the verge of cumming, and he relished the impending release. When suddenly Barbara's voice changed in his mind.