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?
