A Game of Tasks Pt. 01

All characters are 18 years or older.

*****

BZZZ!!! BZZZ!!! BZZZ!!!

Shawn groggily rolled over in bed to shut off the alarm clock, but with his eyes still tightly closed, and having just been woken from a heavy sleep, his first attempt only managed to knock the clock to the floor.

"Ugh...damn it," he swore as the alarm continued sounding from its position on the floor. He pushed himself halfway over the side of the bed to reach the clock and finally shut it off. Shawn then pulled himself back up into bed trying to hold onto the last few seconds of comfort and warmth his bed provided before finally sitting up and blearily opening his eyes.

Sitting on the edge of his bed, Shawn's head pounded, an obvious result of the heavy night of drinking. Looking back on it, Shawn was surprised he had managed to get home.

Sharon, his girlfriend of 3 years, had broken up with him last night. Apparently, she didn't see them having a future together. Something about their goals being too different. Shawn had asked for something more specific, but she had just been increasingly vague in trying to explain it to him. As she struggled to explain how something that had lasted for 3 years with little issue could simply fall apart, Shawn's temper got the best of him and he ended up throwing some cash down on the table of the restaurant they were at and walking out.

The ring he had been carrying for two months sat heavy in his pocket. He found the nearest pawn store and hocked it for a decent amount. From there he headed to an Irish pub down the road from his house. After the first few shots, and a couple of beers, his memory started to get hazy.

Just then his cell phone started buzzing on the nightstand. Shawn looked over at the brightly lit screen and saw his buddy, Liam's, goofy face staring back at him. He reached over and answered the phone.

"Hey, what's up?" he said, as he stood and headed to the kitchen to make some coffee.

"Well, at least it sounds like you are alive. What happened to you last night man? We were having a few drinks, I got up to take a piss and when I came back you were gone."

Shawn blinked a couple of times trying to recall seeing Liam the night before, but no matter how hard he thought about it, the last coherent memories he could think of was sitting alone at the bar.

"Oh, uh sorry about that. Honestly, I don't even remember hanging out with you last night, or even how I managed to get home."

Liam laughed, "Yea, you were pretty trashed by the time I got to the bar. Ah, well. If you aren't in too rough of shape today there is a party tonight on campus. Should be a few girls there that could take your mind off of Sharon."

As Shawn heard the name his heart gave a small jolt and it felt as though pain was shooting through him. He felt the beginnings of tears in his eyes and immediately pushed back against those thoughts. "Yea. Yea man, I am definitely in. I need to get out of the house any way, otherwise I'm going to drive myself crazy," he said as he pushed the button to start the coffee brewing.

"Cool, I'll pick you up later tonight, take it easy man." Liam said as he hung up.

Shawn sat in the kitchen and listened to the sound of the coffee percolating, willing away any thoughts of Sharon. He picked up his phone again and started looking through his history to see if there were any other surprises waiting for him from the night before. As he scanned through he saw what he assumed was the call he made to Liam and not much else, until he checked his text messages.

"Oh, shit!!!"

Shawn looked down at about 10 unanswered text messages that he had sent to Sharon, all at varying times throughout his binge drinking. They started with the usual break up frustration, but quickly devolved into begging for her to come back to him, and then proceeding to call her any name he could think of, before finally finishing off with the pathetic, and cliched drunken apology.

Shawn let the phone slip out of his hand to clatter onto the counter, as he slunk down in his chair trying to think of any possible way that this could get worse. Then, as the universe tends to do, it got worse.

The phone chimed and Shawn looked at it quickly, seeing a message from one of his little sister's friends, "Who is this? Why would I want to look at your dick?" Her name was Hannah. Shawn had always thought that she was cute, with a slim figure, small breasts, a tight ass, and deep, dark grey eyes that just seemed to draw you in when you looked at her. Hannah had been friends with his younger sister for years and they had always gotten along amicably, but he knew that she had caught him on a few occasions when he had allowed his eyes to follow her black, shining hair down to that firm ass as she walked. Hannah had always just giggled a bit, while he tried in vain to appear as though he was looking elsewhere.

Shawn looked at the message quickly, then back at the history. He had decided, in his inebriated state, to send this poor girl a shot of his erect dick. Thanking every deity he could think of that the girl didn't have his name programmed into her phone, he quickly typed back: "Shit, sorry. I was drunk and apparently drunk me is a perv. You can just delete it, I won't bother you again."

Now Shawn wasn't hung like a horse, but he had a decent sized member, and Sharon had always been more than happy with his endowment. Combining that attribute with a naturally fit body, standing at 6'1, Shawn wasn't terrible to look at. He certainly wasn't going to win any body building contests or make it big as a male model, but his light brown hair, blue eyes, and firm jawline always had a way of drawing at least a few glances his way. That being said, he wasn't embarrassed about his penis being seen as much as he was about having been desperate and pathetic enough to try to seduce a girl with a dick pic of all things.

The phone chimed, "Oh shit! Shawn?!"

Hurk! The universe had given him another swift kick to the balls. "Hey Hannah. Sorry again, Sharon broke up with me last night, I got way too drunk and didn't call a friend soon enough to prevent me from doing anything stupid. Just please don't tell my sister."

BEEEP! The coffee maker had finished brewing, so Shawn strode over and poured a cup as he waited for the response from Hannah.

The phone chimed, and Shawn spilled a bit of his coffee in his haste to see Hannah's response, "Well, I suppose I could forget this even happened." Shawn breathed a sigh of relief, then a second message appeared, "If you agree to play a game with me."

Shawn just stared at the screen for a moment trying to figure out what she could possibly mean by this ultimatum. "What does the game entail?" Shawn asked.

"You have to complete 10 tasks that I set for you. Any task that I request you must complete within 24 hours and provide proof that the task has been completed. If you are able to complete a task within 12 hours you will get a...reward. But if you fail to complete a task within the 24-hour period you will have a choice of 5 more tasks, or 1 punishment. At any time after a task has been failed I can choose to speak to Cat about your text message, the only way to prevent this is to complete the next task successfully, or complete your punishment for failing. Do you agree?"

Shawn read and re-read the text trying to figure out what exactly Hannah had in store for him, but after several minutes he had to concede that she had him by the balls and he didn't have much choice, but to agree to her terms.

"Alright, I'm in."

"Excellent, now for your first task I want you to find every dirty picture, message, or video of Sharon, take them up to your room and jerk off to them. Afterwards, I want you to destroy every last one of them."

"What?!"

"And don't forget that I need proof, otherwise I will be speaking to Cat about your dick pic when I see her tonight."

Shawn couldn't believe he had just been told to masturbate to his ex-girlfriend by his little sister's friend. Then the thought of the required proof came to mind. How would he prove that he had done as requested? Unless he took a video of himself doing it. No, he couldn't do that, he got into this mess with a dick pic after all.

Shawn picked up the phone and called Hannah, "Hello, Shawn?"

"Hey Hannah, listen, I am going to do as you asked, but I need you to come by my house in about an hour."

Silence... "Fine."

Shawn spent the next hour finding every possible photo, message, or video that he had of Sharon that could be considered dirty. A few were barely risqué, but the bulk of them had Sharon in a considerable number of sexual poses, in various stages of undress. To be honest, Shawn had not looked much at them after he received them, simply because he had the real thing, but now that he was alone, he found himself getting more and more aroused by what could be described as their erotic life together.

Knock. Knock. Knock.

The noise from the front door shook Shawn out of his reminiscence and he went to open it for Hannah. However, when he opened the door it wasn't Hannah standing there. It was Cat's other friend, Rebecca. Rebecca had pale white skin, as sensitive to the sun as any red head, but she didn't seem to have a single freckle on her milk white body. Her burnt red hair framed her face perfectly and her innocent blue eyes were the focal point of her cute face. The girl was an absolute angel. She was incredibly shy, but had the body of a young model. Her breasts were about a C, but the shape and perkiness put them in a category of their own.

Rebecca coughed a bit, as Shawn realized that he had been standing in the doorway for a few moments longer than would comfortable, letting his gaze linger on her body. He hurried to step aside and invite Rebecca in, becoming immediately conscious of the visible tent in his pants from his time with Sharon's photos.

"Hi Rebecca. Cat is out, but if you are supposed to meet her here then I guess you can wait in her room if you want."

Rebecca shifted nervously, "Oh, um, no. I, um, was sent over by Hannah. She said you, um, wanted to see me?"

Shawn's eyebrows shot up at the thought of using Rebecca as a witness. "Um, just let me call Hannah and see what this is about."

Shawn walked quickly to the kitchen leaving the shy girl standing in the hallway. He grabbed his phone and quickly called Hannah, "Why is Rebecca here? I asked you to come over."

"And I was busy. Don't worry, Rebecca can be a witness for you, and then she can tell me that you succeeded in your task. Everything still works."

Shawn hesitated a moment as he thought about it, "But will she be ok with watching me do...THAT?"

Hannah laughed a bit on the other end of the line, "Of course, she may look quiet and shy, but Rebecca has been wanting to see THAT for quite some time now. Now, make sure you enjoy yourself."

Hannah hung up the phone, and Shawn walked back into the hall, "Alright, well let's go upstairs then." Shawn didn't even wait for a response; his heart was pounding hard in his chest as his led the beautiful girl behind him up to his room where he had set up any erotic material from his now ended relationship that he could come up with.

As they walked into the room, Rebecca let out a small gasp as she saw the computer screen replaying the only erotic video that Sharon had sent him. In it, she lay on the bed slowing rubbing her pussy before building to a fast-paced climax. Sharon was of average build, with a round ass and big swaying breasts. Many guys would drool openly over the tops that she wore when she was out with him, but for Shawn it had been her humorous personality, and caring nature that had led him to fall in love with her. Ironically, Sharon was the exact opposite of his 'type', he thought as he pictured Hannah's tight ass walking away from him.

He shook the images away as he turned to Rebecca, "I have everything that Sharon has given me over the years that could be considered erotic. I am going to lay on the bed, with everything in view and masturbate to everything here."

Shawn waited as Rebecca took in the words. Her eyes opened wide and her mouth dropped open a slight amount. "Rebecca, you don't have to be here, but Hannah needs to know that I fulfilled this task. Now that you have seen everything you can leave and wait for me, then you can watch me destroy everything."

Shawn expected her to quickly flee, but instead she sat in a chair by the door, "No, I think I would like to stay," she said quietly.

He shrugged his shoulders and settled down on the bed with a small container of lube. Shawn pulled his pants down and his cock popped out of the pants he had been wearing, already erect from the video, and pictures on display, Rebecca's presence only made him harder.

Shawn put a small amount of lube in his hand and hit the volume on the computer so that he could see and hear Sharon's video as he began to stroke his long, hard member thinking of his ex-girlfriend and all the time that they had spent with each other. He briefly closed his eyes, and when he opened them again he noticed that Rebecca had moved closer to the bed, staring intently at his cock as he rubbed it. Shawn tried to focus on Sharon, but with Rebecca closing the gap between them quickly all he could think of was her lithe body, and her perfect, perky mounds moving under her tight shirt.

Just as he thought he could not take it anymore he felt a hand on his wrist. Opening his eyes, he saw Rebecca pulling his hand away from his cock and replacing it with her own. She hesitated with the first stroke, but quickly found a rhythm, undeterred by the increasing amount of pre-cum dripping down to lube his shaft. She stroked him slowly and sensually, pausing only briefly to undo the button on the top of her pants so that she could reach inside to caress her pussy.

He started quietly moaning with the pleasure, and Rebecca quickly joined him, a chorus of erotic satisfaction. She pushed her pants down and swung her hips over him so that she was mounted, hovering just above his face as she dove down to engulf his hard penis in her mouth. Shawn couldn't take it anymore, he reached up and pulled her hips down so that her vagina sat against his mouth. He gently stroked her clitoris with his tongue, trying a few different angles, until he found just the right spot. Feeling her tension, he continued his ministrations as her legs gripped tighter and tighter around his head.

She stopped sucking his cock and sat up abruptly, reaching down and throwing her shirt off before grabbing hold of his dick again, stroking his shaft with one hand while her mouth sunk down again to lick and suck his balls.

Shawn continued his clitoral massage with his tongue as he slid two fingers up and down Rebecca's sopping slit, ensuring that they were well lubricated before pushing them inside her, feeling for her sensitive G spot. When he found it, his fingers moved at the same pace as his dancing tongue and quickly Rebecca's legs closed around his head again and she stopped, simply vibrating with pleasure, until she could not take it anymore.

Rebecca rolled off Shawn to stand on the floor, but he stood up and pulled her back against him. He turned her and leaned her over the bed as she pushed back onto his rigid member. Quickly he started fucking her hard, grabbing her sweet, perfect breasts as he hammered into her. Harder and faster they went, until they could no longer stand and they fell to the bed, his cock still buried deep in her pussy. His hand tightened on her sexy ass as he stroked slower and deeper until neither one could take it any longer and he erupted deep inside of her as she came.

They lay panting for what seemed like hours before they finally recovered enough to look at each other. "That was amazing," Shawn said, smiling. He stood and began throwing out everything that Hannah had asked him to destroy. Rebecca reached over to the computer and deleted the video. She stood behind him and stroked his chest and slid a hand down to his cock, "I've always wanted to know what that felt like." She smiled as she gathered her clothes and walked out of the room, pausing in the doorway, "I'll tell Hannah you did as she asked."

Then without another word she walked down the hall to his sister's room, and the private bathroom there. Shawn took the garbage can outside and lit the contents on fire, smiling more than he ever thought would have been possible after the events of the previous night and the morning.

Smiling, he thought that maybe this game would be fun. Just then he got a message from Hannah, "That was fast, well, here's your reward." The picture that she sent was a dark silhouette of her naked form. It looked as though her hand was buried between her legs. Shawn's mouth dropped open, before quickly drawing back up into a smile. Definitely more fun than he thought.