Tim and Jeff had hated Billy for the longest time. Ever since grade school they looked down on him with nothing but scorn and envy. They were both bitter, hormonal teenagers, 18 and angry at the world. Since he was little, Billy had led a carefree, happy life.
Billy's mother, Amy Robertson, was an attractive woman in her mid 30s, who loved her son very dearly and walked him to school every morning. It was this kind of smothering which led Billy to have quite a sheltered and wimpy personality, which Tim and Jeff loathed him for. They had always been bullies and "fish" like Billy were easy pickings to use to feed their feed their ego as well as give them cheap thrills.
With her shapely and round behind, Amy attracted the attention of all the boys she walked passed, and a few teachers too. It didn't help that she often wore very tight, constricting clothes which only emphasized her figure. Unfortunately, she was so innocent and naive in nature, she barely realized this. Tim and Jeff loved to eyeball her as she walked by every day and would often make crude gestures behind her back which she often missed but sent knots forming in Billy's stomach every time he saw them looking. Although she was vaguely aware that Tim and Jeff harassed her son, she wrote them off as nothing more than mischievous teenagers.
"Just ignore them, honey." She'd say as she caught Billy cowering from their grinning faces.
Tim thought she had great tits, and he was right. She had a pretty face and lovely flowing brown hair. She was about 5'11 and very well rounded with a very shapely figure and was often described as "cute" and "adorable", despite the fact that she was in her mid-thirties.
As long as he could remember, Tim wanted to fuck her. Jeff also had an immense desire to have sex with her since the first time he saw her walk Billy to school, which happened soon after he complained of being bullied. The two would alleviate this by regularly jacking off to thoughts about fucking her and often discussed fantasies of what they'd like to do to her.
Because of this Tim and Jeff took special delight in tormenting Billy and made it a habit to pick on him. They tormented him relentlessly but there was little he could do without substantial evidence. If he ever cried to the teachers, it would just be dismissed as schoolyard rough housing and boys being boys. Tim and Jeff would take advantage of this and made sure not to leave any obvious bruises or wounds, and made most of their tormenting psychological rather than physical.
"Hey Billy, I'd gonna fuck your mom right up her sweet ass." Tim would say.
"Yeah, and she'd be sucking my cock at the same time." Jeff would follow, laughing.
Since Billy was so utterly afraid of them he didn't know how to respond to this, wishing that they'd just leave him alone. He was protective of his mother and too much of a wimp to do anything about it.
The nature of their bullying was also often mental rather than physical because Tim and Jeff were pretty perverted. They actually got off talking about his mother in such a derigatory way to her son.
Soon this news got to Billy's mother and father, who were obviously upset about these incidents. However, Tim and Jeff always got away without reprehension as they were just 18 year old students. Billy, who had only just turned 18, felt helpless. It became more and more common for his mother to walk him to and from school to avoid bullying, much to Tim and Jeff's pleasure.
Soon she could feel them stare her up and down as she waited for her son to come out of his lessons, and hated herself for being put in such a submissive situation against her will. What else could she do if her son faced constant abuse?
Jeff loved every second of it.
"Holy shit dude, my cock gets rock hard every time I see that bitch." He said, adjusting his boner and lying down on his bed. "Even thinking about her is enough to make me blow my load."
"I know man," Tim said, turning away from the porn on Jeff's computer momentarily. "You see what she was wearing yesterday? Those fucking tight-ass pants? That bitch knows what she's doing. I bet she fucking loves us staring her down like that. What I wouldn't give to bone her."
Jeff sat up grinning. "Tell me about it. I'd fuck her six ways from Sunday!" The two laughed, continuing to look at MILF porn. Suddenly, an idea popped into his head.
"You know," Jeff began. "Halloween's just round the corner..."
Tim smirked, he had an idea where Jeff was going with this. Every year the two would use it as an excuse to cause mischief and mayhem from a young age, but as they got older their acts became more and more daring. He knew things were gonna be a little different this year.
"All we have to do is find out where they live." Jeff said.
"Oh man, just thinking about it is making me hard. The things I'd love to do to that bitch." It was hard to believe such words escaped the mouths of these two teens, but the truth is they had always been like this. Surely enough, the next day of school began and they cornered Billy.
"Hey Billy, how's it going?" Jeff began, placing his arm around Billy's shoulder, which looked innocent from afar but in actuality was very dominating and frightening to him.
"A-Alright. Things are okay, I guess..." He stuttered.
"That's good." Tim reassured.
"Say, where do you live Billy ol' boy?" Jeff asked, leaning in, unable to conceal his smile at the thoughts in his mind.
"Err... why do you want to know that?" Billy stammered out nervously.
"What the fuck is your problem?" Tim barked angrily, scaring him. "Here we are, trying to be nice, and you have to give us shit. Just tell us where the fuck you live! "
"T-Twelve Roseway Street!" he yelled, terrified. He'd been beaten by these guys before and they always got away with it.
"Good." Jeff said, before kicking him in stomach. Tim joined him, cackling as they did so.
"That day, they followed him home from school just to make sure he gave the right address. Halloween would be the best opportunity to fuck with him and his mom, and they couldn't blow this chance. As ever, Amy was waiting for him at the front door on the rare days she never picked him up from school.
Tim and Jeff grinned at her in a perverted way as she took Billy into her embrace, staring at them with false defiance. As soon as she made eye contact they wolf whistled at her. The truth is they made her nervous. She closed the door and told Billy not to hang around with them anymore. They hung around for a while, scoping out the house and just taking perverse pleasure in knowing where she lived, much to the terror of Billy. No siblings. No wonder Billy was so coddled. Even his father only had the courage to frown and glance out of the window a few times, but it was obvious he didn't want any trouble.
"What a wimp." Jeff said. "If I was him I'd be banging her every minute of the day, but there he is just reading the paper. Fuck, she's hot. Look at him, he's just some scrawny old dude." He laughed.
Now that they knew where she lived, they eagerly looked forward to Halloween. That would be their chance to get what they finally wanted. They were used to terrifying the local kids and vandalizing the houses of people who annoyed them but this year really was gonna be different. As they walked home they discussed perverse things.
"You know if we end up breaking in and looking around I'm definitely gonna steal some of her dirty panties. What type you think she wears? Probably granny panties." He laughed.
