A Game of Tasks Pt. 02

All characters are 18 years or older.

"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."

That's how it started. Hannah, a friend of Shawn's little sister, Cat, had him trapped in a game that required him to complete tasks that she set for him. If he wasn't able to do so, she would show his sister the drunken dick pic that he had sent, and who knew what his sister would do with it. After his long-time girlfriend, Sharon, had broken up with him while he sat there with an engagement ring in his pocket, and the rough night of drinking that followed, Shawn wasn't sure he could take his family's reaction to his unsolicited dick pic. Especially Cat. They had always been close, and he trusted and relied on her support. He couldn't imagine damaging that relationship with a stupid drunk text.

So, the only alternative was to play along with Hannah. The first task was done, and as he sat looking at the dark silhouette of Hannah's naked form that she had sent him as a reward, he started to like the idea of playing her game...until he saw what the next task was.

"Now that you have your reward, I have your next task. The game isn't going to take breaks, Shawn. When you have completed or failed a task, the next instructions will come out, and the timer will start."

Shawn read the text, the directness of the message dampening his enthusiasm at completing the first task successfully. Shawn waited for Hannah's next text, his next task, with growing apprehension. Somehow, he doubted the second task would be as simple as the first, but despite his hesitation, he found that he was smiling, thinking about fucking that beautiful redhead, Rebecca. That and burning the sexual paraphernalia he had kept from his relationship with Sharon, combined to create a very cathartic experience for him. Shawn shrugged, maybe there was something he could take away from the game, he thought as the phone chimed.

"For your second task..."

Shawn waited.

"Fuck a girl in the ass."

He blinked, "What? That's it?"

"Well, you obviously need to give me proof that you did it. Why, do you think this task is too easy? Convincing some girl that you have never even properly fucked to let you stick it in her ass?"

Shawn thought about that. It had taken him almost two full years with Sharon before she let him try that, and even then, it had only happened once. "Shit, no, that's difficult enough," Shawn texted back to her, "I don't even know if it's possible."

"Aw, Shawn, don't lose your confidence, now. Especially, after the way you drilled Rebecca just a few hours ago. Just whipping your dick out and stroking it a few times was enough to have her dripping, I'm sure you can do this...and, of course, if you can't do this I am sure little sister will be happy to see what big brother looks likes. Ha ha ha."

Shawn threw the phone onto the nearby couch, frustrated enough to toss the device, but not quite pissed enough to break it. How was he supposed to do this in 24 hours? Shawn sat sulking over his dilemma, then it hit him: the party! It was his only good chance. There would be lots of girls with, hopefully, a lot of different sexual preferences. Combine that with alcohol and he might just be able to pull it off. He would have to prepare, though. There were always a few normal road blocks between a guy and a girl's ass.

Shawn pulled himself up off the couch, grabbing his phone on the way, he headed upstairs to get ready for the party. The first road block was cleanliness. If the guy looked and smelled like garbage, there was very little chance of hooking up, and he could forget about anal. Shawn took his time making sure that his nails were cut, his face was shaved, and he had some clean clothes that didn't make him look like a slob, then he jumped in the shower.

He had just started washing his hair when the air temperature changed slightly. Shawn hadn't heard anything but he was sure that someone had come into the bathroom. "Hello?" he asked, as he tried to wash the soap out of his eyes, "Is someone there?"

Then he felt a small hand on his dick. "Mmm, sorry Shawn, but I wanted another taste," Rebecca said as she lowered herself onto her knees, licking her lips. As the soap washed out of his eyes, Shawn looked down to see the little redhead start bobbing her head on her cock. Her pale, lithe body, glistened as the warm water of the shower cascaded down her back, and into the crack of her cute little ass.

Shawn began pumping his cock in and out her mouth, her red tresses wrapped tightly around his fingers as he fucked her. "Is this what you want Rebecca? You want my fat cock jammed down your little throat?"

Rebecca tried to answer, but Shawn didn't give her time, thrusting harder and faster into her mouth as she pumped his cock with one hand, and dug her nails into his ass with the other. The pleasure was phenomenal and Shawn's rational mind had stepped out for the moment giving his animal urges full control as he pulled Rebecca's mouth deep onto his cock, eliciting a small choking sound. He held it there for just a moment before exploding into her throat.

When his orgasm stopped he quickly let her go, "Ah shit, sorry, Rebecca."

She smiled up at him, "That was fucking amazing, Shawn. I have never felt so much raw passion before in my life. You have nothing to apologize for...so long as you promise we can do that again some time," she said, as she got to her feet beside him. Turning around and bending over she asked, "Is there anything else you want from me tonight?"

Shawn couldn't believe what she was offering. Could this task be so simple?

Knock! Knock! Knock!

"Shawn, are you going to be much longer? I just got home and Rebecca said she was here, but I can't seem to find her."

Rebecca stood up straight again and Shawn motioned for her to be quiet, "Uh, yea, just a second Cat." Shawn turned off the water, stepped out of the shower, and put a towel around his waist. Walking to the door he went to open it, but turned to check that the shower curtain was closed first. "Hey Cat," he said as he walked out of the bathroom and closed the door behind him, "I'm not sure where Rebecca is. She was here earlier, but said she was going to wait for you in your room. Then I started getting ready, and that's really all I know."

Cat looked back at her brother for a moment, suspicion evident on her face. Shawn had never been able to lie to his little sister very well, and he just about told her the truth, when there was a loud chime from her phone.

"Oh, looks like she just went to the corner store and said she will meet me at the coffee shop down the street when she's done," Cat read out to him. "Well, I guess, sorry for interrupting your 'me' time," she said motioning down at his still hard cock.

Shawn's face turned a crimson red as he hurried to move his hands in front of his engorged member. Cat just chuckled a bit and went back to her room. He heard her rustling through her drawers for a bit, then she walked down the stairs and out of the house, presumably to meet Rebecca, who was just now coming out of the bathroom wearing absolutely nothing.

"That was close," she said, smiling coyly. He watched her walk slowly and sensuously back down the hall, her clothes in hand, every motion a display of her sexuality, until she closed the door to his sister's room. Shawn went back into his room to finish changing, cursing his sister's timing as he heard Rebecca leave the house. He had been so close to finishing Hannah's task...and so close to that delicious ass.

Shawn shook his head to try to get reoriented on tonight's goal. The first roadblock was taken care of; he was clean. The second roadblock was ease of access, or as it was better known: lube, he pocketed from his side table drawer. Just then he heard the front door open, "Hey, Shawn, are you ready to go, bud?"

Shawn took one more look in the mirror, decided it was the best he was going to be able to do, and headed downstairs to meet Liam in the hallway. "Hey man, sorry again about Sharon," Liam said as he gave Shawn a bro hug...You know the hug I'm talking about, the one where the right hands are clasped in greeting and kept firmly between the bodies of the two bros hugging it out, as the left hand goes around the back to give 3 quick pats before releasing each other. It was designed to impart some comfort, and affection, but to ensure that no onlooking females could ever mistake it for anything but a bro hug, thus ensuring that both guys appear available. It has the added side effect of avoiding the awkward penis touch that can occur with the full-frontal hug.

"Yea, it was rough last night, but I am starting to move past it...even got rid of a few old pictures and a video we had together," Shawn said as he put on his shoes and walked past his friend, out the door.

"Really? That's awesome, Shawn, and tonight we are going to take it a step further. You are going to get plastered, but this time instead of calling me to help drown your sorrows, you're going to hook up with one of these chicks and let her take all the pain away. You know, with her mouth, or hand, or pussy, or -"

Shawn gave his friend a quick punch to the shoulder. "Enough, enough. I get it, Liam. I get drunk, I get a beauty, and I get laid. The usual male recovery formula."

Liam chuckled, "Well, beauty might be an optimistic term, my rusty friend, but I guess if you drink enough it could apply." Shawn punched him in the arm a couple more times, then they laughed and joked as they drove to the party.

Liam pulled up to a large white house that had music blaring and a bunch of people flooding into it. The guys grabbed a couple of cases of beer from the trunk and headed inside. The house was packed with people, and Liam quickly made for the kitchen to hopefully grab some fridge space with Shawn in tow. Once they had reached the kitchen through the throngs of people, they managed to fit in a couple of bottles to cool and stashed their beer in a pantry.

"Alright, now we try to find some available legs just waiting to be parted," Liam said as he opened a beer and took a large swig. Shawn to a swig of his own beer, rolled his eyes at his friend, then turned to scan the crowd.

There was a good ratio of guys to girls, Shawn thought, which meant that there weren't many guys, but there were a ton of girls. The average age looked to be around 20-21, and the party looked like it was just getting started. Everyone had a drink in hand and was either talking, laughing, or dancing. Liam finished his beer, grabbed another one, then slung an arm around Shawn's shoulder.

"Well, Shawn? Where are we headed?"

Shawn pushed his friend off of him, finished his own beer, grabbed his second and headed onto the makeshift dance floor. Liam followed, but split off quickly when he caught sight of a tall, leggy girl. Her ebony cleavage perfectly displayed and drawing onlookers from all around. Shawn glanced back once to see his friend taking her hand and leading her off the dance floor, before he turned back to his own task. How the hell was he supposed to find someone that would let him fuck her in the ass?

Shawn tried to dance with a few girls, but most of them walked away after a song or two, and had little interest in his 'dance moves'. Deciding that the dance floor was probably the worst way he could have started his foray back into the world of singles he headed back to the kitchen to grab another beer.

"Hey, do you mind if I have one of those?" a voice behind him asked. Shawn was about to say that the voice could find their own alcohol when he turned around and saw a cute little blonde with perky tits leaning over the kitchen island.

"Oh, um, yea sure," he stammered, grabbing her a beer. The girl was a knockout. Her baby blues alone drew him in, as he awkwardly walked over and sat at the island with her. She was wearing a tight white tee that was cut way too low. Shawn could easily see the top of the bright red bra she had underneath, and bent slightly as he handed her the beer to see if he could catch a glimpse of anything more. She was wearing simple blue jeans, but from the way she was bent over, Shawn was sure the fabric was having a hard time containing her round ass.

She twisted off the top and took a quick sip of the beer before settling onto the stool she had been kneeling on. "Thanks. My name is Sue, or Suzy if you like," she said with a smile that almost knocked Shawn off his own stool. "And you are...?"

Shawn floundered for minute trying to remember his own name. "I'm, uh, Shawn," he finally managed to get out of his uncooperative mouth. "Hi, Shawn, thanks again for the beer," Suzy said as she hopped down and started walking away.

"S-Suzy, do you want to dance or something later on?"

Suzy looked like she had just been asked to eat something disgusting as she turned back to him, "Um, no, John. I do not want to dance or do anything else with you." She turned and walked away.

"Damn, that is one cold bitch!"

Shawn turned to see a thin girl wearing a tiny black dress with an antique feel to it. She had black lipstick, black hair that hung down to a cute little ass, and her breasts were probably a small C cup. The dress only came down to mid-thigh and Shawn's eyes followed her legs all the way down to a pair of small black heels. Once he managed to follow those legs back up again his eyes met a pair of almost violet coloured eyes. Shawn stared for a moment more before she said, "Hi, I'm Victoria."

He shook his head a bit and subconsciously took a step back. His body moving of it's own volition after the brutal way in which he was shot down.

"Hey, get back here," Victoria said as she two a couple of steps and grabbed his arm. "I am not like the ice queen who just walked out of here."

Shawn noticed his retreat and stopped, "Sorry, that was just..."

"It was an entitled cunt," Victoria said with a bit of venom in her voice.

Shawn couldn't help it, he burst out laughing. "That is the most accurate thing I have ever heard a complete stranger say to me, ha ha ha."

Victoria tried to keep a straight face but failed miserably. "Ha ha ha, well she is," she said as they laughed together.

"My name is Shawn, by the way, not John, as the entitled cunt said. Do you want a beer?"

"No, that's fine, besides I have already had way too much to drink. Why don't you finish yours and we go out to the dance floor?" Victoria asked.

Shawn quickly finished off his beer, took her hand and led her out to the makeshift dance floor, where the memory of his past failures quickly reminded him that he had two left feet. "Oh, uh, I'm not very good at dancing," Shawn said.

Victoria grabbed his hands, put them around her waist and put her own around his neck. "Don't worry, it's just like sex: the first time with a new partner is a bit awkward to start, but you find the rhythm."

Shawn's cock gave a small jump at the mention of sex by his dazzling dance partner, and his mouth got a little dry. He tightened his grip slightly on Victoria's waist, pulling her closer to him, as they began a slow circular dance, gazing into each other's eyes. They circled like this a for a couple of songs, then Victoria stepped in close and rested her head on Shawn's shoulder. He could feel her breasts pressed against him, and her thigh moving between his legs. Shawn stopped moving as he stared down at the cute little ass of the girl he was holding, but when Victoria stepped on his foot with her heels he apologized and started moving again. That's when the music changed.

The slow songs were replaced with a heavy club beat and Victoria turned to grind her ass against his hardening cock. He hoped she didn't notice as he did his best to keep up with the grinding motion, but then she took his hand and guided it to her breast. Using her hand, she made him squeeze her breast through the dress she was wearing then moved his hand again, to slide inside her dress. Shawn cupped her bare breast as she continued to grind his cock. It felt so good, and so sexual. Shawn couldn't remember the last time dancing was fun, but he was enjoying himself now. Then suddenly Victoria grabbed his hand and began dragging him off the dance floor.

"Hey, um, what happened?" Shawn asked as she continued to pull him through the crowd of people, "Are you ok?" he asked.

"No. I need that cock," Victoria said as they made their way upstairs to one of the many rooms. She shut the door and pushed him down on the bed, then began unbuckling his jeans. It only took her a moment to have his pants off and his cock out. Victoria stood in front of Shawn, lifting her dress enough for him to see a cute pair of white panties. Then she slid her hand down the front of them and began rubbing her clit, stroking her finger in and out of her pussy every so often, all while staring hungrily at Shawn's cock, almost daring him to try to get up. Shawn didn't move. The show was too good. He watched every motion of her little hand, and as her pussy got wetter and wetter, the panties became more and more see through. Finally, when it seemed pointless for her to be wearing them, Victoria turned around so her ass faced Shawn, and slowly, pulled her panties down over her cute little ass. When she turned around, Shawn could see that she was completely bare.

Victoria walked back to him, letting her dress drop, and straddled his hips. She lowered her dripping pussy down onto his waiting dick. She was tight, but horny as hell, as she sunk right down to his balls, then began riding him like a prized steed. Victoria rode his hard cock, bending to suck his lip into her mouth and biting lightly. Shawn responded by digging his nails into her little behind and thrusting hard up into her. Just as their dancing had begun as clumsy and uncoordinated, so to seemed the first few seconds of sex until they both let go and let passion take control. Shawn stood up with Victoria still riding his cock, turned and laid her on the bed, then with one arm holding both her wrists above her head, and his other hand gripping her ass tightly he drove his cock into her again and again, harder and harder until she was shaking with pleasure. She kissed his shoulder at first, but as the pleasure increased she bit down out of instinct, holding on to him with her teeth as he fucked her. Shawn just about came as she orgasmed hard on his cock, but he slowed himself down enough to hold on longer. Shawn stroked in and out, deeply, and slowly, as Victoria's pussy clenched around him, and her body writhed with the intensity. Finally, her orgasm subsided and Shawn began to pick up the pace again, when she turned her body away from him, his cock slipping out of her pussy.

"What's wrong? Are you ok?"

"I am more than ok, that was fucking amazing!" she said, panting, "But now I want you to fuck my tight little asshole." As she said this she pulled up her dress and bent forward sticking her ass out to him. Shawn couldn't believe it. He had completely forgotten about the task, but here was this amazing, beautiful girl offering him the one thing he needed to fulfill it. Shawn quickly grabbed his pants and rifled through them to find the small bottle of lube he had brought. The last roadblock, willingness, was no longer an issue.