[SIDE STORY] Rags to Bitches

{HayBre here. This is the first side story, so shoutout to over 100 favorites! As a reminder, all side stories will be from the viewpoint of characters in the story aside from Jordan. As such, different styles and themes will be present in them from the main branch. They are happening in the background, but are still canon to the main storyline. This side story takes place between Obedience and Artwork. In particular, it will have more aggressive language and darker fantasies}

Nicotine. Nicotine. Nicotine. Fuck.

Rags needed something. Everyone at this goddamn school was out of fucking pods and waiting until the bell rung after lunch to be able to take a smoke break was absolute hell. Not to mention it was humid as fuck outside. Fuck. Fuck.

He pushed on the bar of the outside door with his elbow and reached into his tight denim pockets to pull out a slightly crushed pack of menthols. As he stepped outside, he struck the box against his hand a few times before pulling one of the slender cylinders from within. It was in his mouth and he was about to light it when he heard something behind him.

"Bum a smoke?" the feminine, yet raspy voice asked.

Rags turned around to see one of the emo band geeks standing there looking at him hopefully, wearing a letterman jacket as if she had earned it. It was bad enough that he had to delay his nicotine gratification until between classes, but now this punk rock wannabe wanted to leech off of him. His lips turned downward in disapproval, "No."

"Fuck me. Are you for real? I'm just trying to catch a buzz dude," the girl, Jane, whined with a roll of the eyes.

Rags was about to ignore her, when her words hit him like a ton of bricks. He knew that she had not meant it in that way, but she had technically just told him to fuck her and he did not think the game was going to differentiate between a sarcastic sexual offer and a legitimate one. Ordinarily, he would not be caught even looking at gutter trash like this bitch, much less considering fucking her. But Jordan had already taken an early lead with three awards on his first dare. Rags could not afford to lose.

His hands dropped down to his belt as he looked around to make sure no one was anywhere near, before eyeing Jane up. "Okay. If you want to," Rags replied, somewhat muffled with the cigarette in his mouth.

"What?"

"You asked me to fuck you. I'm gonna fuck you," Rags explained as he took the cigarette out of his mouth and stashed it behind his ear. She was beyond lucky to get the chance. He was by far the most attractive guy at the school and she was a green haired freak. She certainly was not in shape, though fortunately for her the majority of her weight seemed to have subsided to her tits and ass, but he was an athlete with maybe seven percent body fat and a face that belonged in Hollywood.

Jane began to blush profusely as Rags began undoing his belt. "Ha. Ha. Ha. Very funny. You're definitely going to just drop your pants and I'm gonna suck your dick right?" she mocked, thinking she saw through his ruse.

Rags rolled his eyes. This cunt just kept making more sarcastic offers but he was going to have to follow through with them. At least this way she'd shut the fuck up for a bit with something in her mouth. "Right. That's exactly what you're going to do," he said as he pulled his jeans and boxers down in one swift motion to let his thick cock dangle in front of her.

Jane stood there, bewilderment in her eyes. One of the most popular and attractive guys at school had just gone from denying her a cigarette to now whipping out his dick in front of her so she could suck it and then get fucked by it. There was no way this really was happening.

"C'mon bitch. I don't have all day. I'm sure you're used to blowing on the tuba or flute or whatever the fuck you geeks do. Now get down there and lets get this over with," Rags impatiently barked out. Just because he had to accept the offer did not mean that he had to be nice to her. Maybe if she rescinded the offer because of him being an asshole, that would let him get around the dare......and nope. She was on her knees and **** down his cock before he could even let that train of thought complete.

"Wow. I wasn't wrong, I bet you've done this a lot. You're probably a hit with those pimple faced psychos right?" Rags jeered at her as his cock quickly hardened in her mouth. If she was upset by his words, she certainly did not show it as she worked him up to full length without letting him leave her mouth. The sensation certainly was not unpleasant, but then he looked down and saw her looking up at him with her radioactive hair and goth eyes. Was he really doing this right now?

Jane began to withdraw off of him to take a breather, when he grabbed a fistful of her hair and pulled her down to the hilt. Her lips were pressed up against his groin as his dick pushed against the back of her throat. She began to gag and her throat spasmed around the tip of his dick, but he held her there. Her eyes welled up with tears as she looked up at him and did her best to stay calm, but he looked back at her without any sympathy.

Finally letting go of her, she pulled away and gasped for air before having a coughing fit. Rags chuckled at this as realized that all he had left to do was to fuck her without her making any more sexual offers. "Stand up and don't say a word. Take off all of your clothes and bend over the railing," he commanded. She nodded and wiped away the running mascara from her face while she stood up.

"I bet you pierced your nipples or something didn't you?" He teased as she began slowly taking off her jacket and lifting up her shirt. Underneath, was a floral print bra that contained her generous bust, to which Rags laughed and teased even harder. "Is little miss rebel secretly a girly girl? What? Decided not to wear the one with a cute bow on it today?" He reached forward at the front clasping brasserie and yanked, breaking the clasp and letting it fall to the ground. "Damn. Not pierced. Now hurry up."

Jane had never been treated like this, especially not by someone who she was getting intimate with. But some part of her was too excited to stop. To put her foot down. Part of her wanted him to treat her like this. She quickly and unceremoniously pulled down her pants and underwear and pulled them out over her shoes. She set them down beside her and turned to bend over the railing. Down below was a garbage dumpster on the asphalt. Certainly not a romantic place to have sex.

"Wow completely shaved. You really must get it on with those freaks pretty often. Are you the center of attention at band camp?" he continued as he lined up behind her. "I'm sure they all get the privilege of your cunt, so I hope you don't mind that I take the road less traveled. Good thing you slobbered on me or this would be a lot less comfortable," and with a smack on her fat rear, he pushed the head of his cock forward into her tight cavity. While he did not push all the way in with one go, he certainly was not going slow. She held back a whimper and her knees shook after his third thrust pushed him the full way in.

Rags felt the pressure building up in his balls already, as her tight asshole clenched down harder on his dick. Ehhh. Not like he cared about her pleasure anyway. He just had to complete this stupid dare. One. Two. Three more pumps before he began to cum inside of her ass. It was a generous load too and it oozed out of her hole and down her leg when he pulled out. "Ugh. That was awful. Why did I have to fuck you, of all people?" Rags said with disgust as he looked down at her. He wiped his dick off on her ass cheek before pulling up his pants and kicking her clothes into the dumpster below, "Never speak to me again."

And with that, Rags left her confused, horny, and with an ass full of cum standing naked behind the school. The bell rung, signaling it was time to go to art class. He was disgusted with himself and could not escape the chills running through his body over what he just had to do. That or maybe it was that he never ended up getting his nicotine buzz. Fuck.