Punishment Fits The Crime 3

Everyone was gone. Jake had checked twice, wandering through the entire office as if he had forgotten some last minute thing. A few lights remained on, forgotten as folks rushed out the door. But it didn't take long to be sure, as really the office wasn't huge. 30 people or so, total, on the second floor of a nondescript office building. His cock began to harden as he thought of what he was about to do.

It was crazy, but it was the latest dare in a game his girlfriend had initiated and she had been playing along with every dare he gave her, each one riskier than the last. Though she always seemed to find a way to put him in situations that made him feel vulnerable yet horny as hell. This time was no different. Stacy had just finished his latest dare (flashing her tits while driving to work, as he watched via video chat) when she came up with a new challenge for him.

"I dare you to jerk off and cum on your bosses desk, then lick it up for me." Her voice was husky as she said it and Jake could tell this game made her horny. He also knew she would want to watch on video while he completed the dare. They hadn't really defined any punishment for the loser if someone wimped out, but that wasn't a problem yet because they were both so into the game. Jake quickly agreed, but said it would have to be after everyone had left.

And so, here he was sneaking around the office to make sure it was empty. Now that he had checked twice, he opened Facetime and made the video call to Stacy. She immediately answered, and he saw her naked on her bed which made him even harder. Her 36D tits were heaving gently on the screen and the phone was clearly propped somewhere as both her hands were on her pussy.

"Hey babe," she answered "ready to give me a show?" Stacy shuddered slightly as she spoke and Jake was sure she had been edging herself for a while in anticipation.

"Yeah, but I think you are ahead of me." Jake was walking into Mr. Howard's office as he said it. The office had a window that looked out on the open area of the office where most workers, including Jake, had cubicles. As a Supervisor, Jake's cube was larger than most and could be seen right from this window.

On a bookshelf to one side of the window, Jake saw a few family pictures of Mr Howard with his wife and sons. Jake was surprised they were still up since he knew they had divorced about a year ago. The former Mrs Howard was a looker though, and Jake wondered if the petite blonde ever missed the muscular black man who towered over her in the pictures.

Stacy's voice brought him quickly back to the dare at hand "Loverboy, are you gonna cum for me or are you pussing out?" She smiled and licked her lips as she played with herself.

As an answer, Jake propped the phone on his bosses desk so he could watch Stacy as she watched him, then unbuckled and dropped his pants and underwear letting his hard cock spring free. He started slowly stroking but Stacy interrupted.

"No way! I'm naked for you, I want you naked for me. Get those clothes off, bitch!"

She knew that it made Jake even hotter when she took command, and his dick immediately bobbed even higher as she ordered him to strip. He hesitated, because the idea of jerking off in his bosses office was already making him nervous and being completely nude made him feel even more vulnerable. But he knew Stacy wouldn't accept anything less than obedience once she was into her dominatrix role, so he slipped off his shoes and then the rest of his clothes. Now completely naked in front of her on the screen, he began stroking his cock again.

Precum was already flowing in a steady stream from the head of his dick and as Stacy moaned on the Facetime chat Jake knew he wouldn't last long. Within a couple of minutes, he tensed up and felt the cum jetting from his full balls to land in long puddles on Mr Howard's desk right in front of his phone. Stacy moaned louder as the first wave of her orgasm hit. When they had both calmed down, she stared straight at him on the screen and started playing with her pussy again with her right hand as her left twirled her nipples.

"You aren't done with your dare, bitch. Lick up that cum for me."

Jake stared at the gooey white puddles on the desk, his right hand still holding his semi-hard cock. This wouldn't be the first time Stacy had made him taste his cum, she seemed to get off on it. But it would be the first time he actually had to eat the whole load. Reluctantly, he leaned forward and trailed a finger through the mess then lifted it to his lips and sucked it clean. Stacy moaned, and then spoke up.

"Uh, uh. No hands. I want you to lick it off the desk like a good boy." Jake could hear the wet sounds of her fingering her pussy as she spoke. He bent over the desk and began licking and slurping up his mess as Stacy started cumming again.

By the time he was finished, Stacy had cum twice more and Jake's lips were coated with slime but his bosses desk was clean and shiny. He dressed and could feel himself getting hard again as he thought of the fucking he was going to give her when he got to her place. But that hope was dashed when she came down from her self induced high.

"Baby, that was awesome but now I am going to take a nap. Can we see each other on Saturday?"

Jake was disappointed, but agreed and realized he was probably going to have to jerk off again once he got home. Which was not his favorite, since he lived with 2 other guys in a 3 bedroom apartment.

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The next day at work, Jake was busy throughout the morning and didn't talk with Stacy till his lunch break. He was sitting in the break room grabbing a quick bite of yogurt when she Facetimed him. He answered the call and smiled at her "Hey you, how is your day?"

Stacy was at work too and he noticed that she had undone an extra button on her blouse, so he could see deep into her cleavage. It didn't look like she had a bra on either, since he could clearly see her stiff nipples through the thin material of her blouse. Jake felt himself start to get hard, and shifted uncomfortably in his seat as Stacy giggled.

"What's up, lover? That yogurt looks soft and creamy...remind you of your dinner last night?" She pinched her left nipple as she said it and Jake envied her private office as his cock became fully erect and tented his pants there in the breakroom.

"Babe, that's not fair. Why don't we talk about it tonight?" He angled for a chance to see her sooner, hoping she would break down since she was obviously still horny.

"Sorry, loverboy. I have drinks with the girls after work tonight. Saturday still works though. And it is only two days for you to wait. It will make it better." She smiled cruelly as she continued to tweak her nipples. "Hey, gotta run to a meeting. Talk to you soon." She ended the call and Jake finished his yogurt as he waited for his erection to subside.

When he finally went back to his desk, Tasha was waiting there. She was one of the two interns assigned to his team, and hoping to get hired. Jake had hinted to her that "eager" candidates were always welcome, and was really hoping he could get a stockroom blowjob from her sometime soon. He had been lucky with two of the last three interns, getting one of them to blow him a couple times and the other to give him a quick handjob when everyone was gone.

Tasha didn't seem interested, and had bristled at his comments, but maybe she would soften when she realized he could put in a good word. In the meantime, he spent half his time eyeing her and the other new intern Trish. They both had amazing asses and full lips that he imagined sliding down his dick.

Sadly, all Tasha wanted once he got back was some reports that another Supervisor had requested. He got them for her and took the opportunity to "accidentally" brush his cock against her ass as he stepped around her. She left in a huff and he got back to work.

***********************************

That afternoon, just before 5pm, Jake was wrapping up his day and got a message from Mr Howard asking him to meet him before leaving. Jake was anxious to get home and take care of what Stacy hadn't, but knew he couldn't ignore the request. At 5 on the dot, he walked into Mr Howard's office.

His boss was on the phone and waved Jake to a seat, motioning for him to close the door. Jake noticed the blinds were also closed on the office window and briefly wondered if he was in trouble, but laughed at the idea as he knew he was hitting all his department numbers.

While his boss talked on the phone, Jake's found himself staring at the desk and his mind drifted back to last night. He remembered the feeling of his semen shooting all over the smooth desktop and then the shame but excitement that washed over him as his tongue dragged through the puddle of warm cum. His cock was fully hard when Jake was broken from his reverie by Mr Howard's voice.

"Jake? Jake! Earth to Jake."

"Whoa, sorry Mr Howard. Must have zoned out for a minute. How are you today?'

"Well, Jake, honestly I am a little concerned."

"Concerned? What about sir?"

His boss looked upset as he spoke "Jake, about a month ago I found out someone had stolen files from my office but I wasn't sure who."

"Mr Howard, I would never..." Jake stopped as his boss waved him quiet

"Oh, I know it wasn't you. I eventually caught the person responsible. Do you know how?"

Jake shook his head quietly.

"I had cameras installed the week after it first happened, so that I could have proof the next time someone did anything in my office without my permission."

Jake felt the blood drain from his face, and the erection he had was instantly soft.

"Of course, those cameras stayed and I check them every few days just to see. They record to a hard drive, so that I have evidence if there is ever a problem. I am sure you can guess what I found today when I checked the cameras, can't you Jake?"

"Sir, I, I, ..." Jake stuttered, trying to think of something to say. How could he have been so stupid?

"That's right, son. I found video of you, jerking off on my desk and then sucking up your cum like a little faggot. I am sure you know what will happen if I take this to HR."

"Please, sir. Please. You can't tell them. It was just a stupid dare from my girlfriend! Please, I need this job."

Mr Howard leaned back in his chair. "Jake, if I let you keep your job, that puts me at considerable risk. I will give you one opportunity to convince me to think about it, but you will need to really do a good job." As he said this, Jake's boss rolled his chair away from his desk to reveal that he was naked from the waist down.

Jake had never seen a dick that size, except in porn videos. It had to be at least 8 or 9 inches and was thick and veiny, with a clear drizzle of precum already sliding down the black head. He stared at it and then suddenly realized what his boss was saying. Jake began shaking his head and pleading.

"Mr Howard, sir, please. I am not gay. Let me find some other way to make it up to you."

"Not gay...but you licked semen off my desk. Right. Listen, you call it whatever you want. Pretend you're eating a banana if you like. But you have 10 seconds to get on your knees and convince me I should think about letting you keep your job. Otherwise, the video from last night is going to our HR manager. Come to think of it, maybe I should send it to your emergency contact too..." He clicked some keys on his computer "Cindy, who is that? Your mom?"

Fuck! Jake couldn't risk getting fired, much less his mom watching him jerk off and eat cum. Slowly, he slid off his chair and crawled to kneel in front of his boss. The huge black cock bobbed in front of his face.

Feeling as if he was in a trance, Jake opened his mouth as his boss directed the head of his cock slightly forward. Slippery with precum, it slid over Jake's tongue as his lips closed around the shaft and his nose filled with the musky scent of Mr Howard's big black cock. He worked his tongue over the shaft, slick with the natural lube that was quickly filling the little space left in his mouth.

Suddenly, Mr Howard put one large hand on the back of Jake's head and began forcing the younger man down on his dick. The head pressed against the back of Jake's throat and he gagged, pulling back quickly. But his boss stopped him before he could pull his mouth completely off, and pushed his head back down. Jake took the hint, and began bobbing his head up and down, taking the dark shaft as deep as he could. The precum had built up so much in his mouth that he had to begin swallowing on every third downstroke in order to keep from drooling it out of his mouth.

"Good boy. You're a natural born cocksucker." Mr Howard chuckled, and Jake felt his face flush a deep red with shame. He wanted to pull back, to stand up and tell his boss to fuck off. But instead he felt the thick shaft plunging even deeper in his throat until it suddenly popped past the back of his throat and slipped all the way inside. Jake's nose was buried in Mr. Howard's pubic hair and the slick cock was buried deep in him.

The pressure at the back of his head lessened just as Jake began to feel faint from lack of air, and he quickly slid his mouth backwards letting the dick pop free from his lips and a long string of drool run down to the floor. His boss laughed and plunged his head back down, beginning to fuck his face in earnest at a medium pace. Every third stroke, he would allow Jake a brief moment to gasp for air before thrusting in again as if pounding a wet pussy.

Finally, Mr Howard slowed his rhythm and pulled his huge cock back until just the swollen head parted Jake's lips and rested on his tongue. One hand on the back of the younger man's head held him in place and Jake looked up pleadingly as he felt his boss' cock begin to pulse and swell. Looking up only made the moment worse, as he found himself staring into Mr Howard's phone camera just at the moment that semen began filling his mouth in awful, slippery jets.

The spurts of cum were rushing over his tongue so fast that Jake had to start gulping them down in order to avoid drowning in sperm. His shame only deepened as his abuser spoke.

"Good girl. Eat that cum like a good slut." Jake did so as his face flushed a hot red, choking down each slimy spurt as it filled his mouth. After what seemed like forever, they stopped. He wanted to pull his mouth off of his boss' cock, but didn't dare without permission.

"Mmmm, looks like you might have a job after all" Mr Howard said as he grinned behind his phone which was still pointed at Jake's dick-filled face.

"Here's the deal, starting tomorrow you are demoted to my personal assistant. Your new job pays $9 per hour, and one requirement of continued employment is you will suck cock a minimum of twice daily." Jake's eyes widened, and he tried to pull free from the dick he was sucking so that he could protest. $9 per hour was less than half of his current pay! He would never be able to pay rent and bills on that. But Mr Howard pressed harshly on the back of Jake's head with one large hand and held him in his place.

"I know, that is a significant reduction in pay. But you will be given an option to earn back the difference. Now, you can either agree to your new position or you can decline and have these videos be released. What will it be? Do you want to be my assistant?"

Jake knew he was defeated, and he nodded his head in agreement as a tear of shame ran down his left cheek. Mr Howard smiled.

"Good. But I think you should be happier than that. In fact, I think you should thank me." He released his hold on the back of Jake's head, allowing his semi-hard dick to pop free from Jake's lips. "Well?" he said "Aren't you going to thank me?"

It didn't even sound like his own voice as Jake opened his mouth and heard the words come out. "Th-th-thank you sir." Thick strings of sperm and drool hung from his lips as he spoke, and his boss chuckled while holding the phone camera steady.

Minutes later, Jake was in the parking lot as he watched his boss drive off. With the taste of semen still filling his mouth, all he could think of was...what would tomorrow be like?