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.
“Nah dude,” Jeff said. “I bet she’s the type of slut who likes to seem prim and proper but actually wears sexy as fuck underwear. Lacy shit. I guarantee you her dickweasel of a husband doesn’t make her feel like a woman.”
For the next week or so this type of talk carried on and they found the ideas they discussed becoming more and more daring. The only thing they jerked off to now was MILF porn and they could barely contain themselves. They even took following her and photographing her ass with their cameraphones, making no effort to hide it.
Finally, when Halloween came around they headed straight over to Billy’s house. They knew what they wanted and knew they had to savour all the time they could. They arrived at the front door.
“This is it dude.” Jeff said. They knocked harshly three times.
“Trick or treat!” they said in unison as she answered.
“Well!” Came Amy’s reply, unable to recognize them in their cheaply made ghost costumes. “Aren’t you big ghosts!” She said, holding out candy.
“I sure am!” Tim laughed. Amy raised an eyebrow at this. She looked incredibly sexy in her genie costume, which was made up of silk and transparent materials, doing little to hide her enormous cleavage with her 34D breasts, which Tim and Jeff’s eyes were glued to.
“Well, here you are.” She said, giving them an equal helping of candy each. She was wearing tight purple sweat pants that complimented her figure and especially her ass.
“Oh no,” Jeff said, stepping forward and keeping her from closing the door. “We’re gonna need a LOT more than that to be convinced not to trick.” He stared at her tits and made no attempt to hide it. This immediately made her feel uncomfortable.
“I think you two should go,” She said, trying to close the door. Jeff held it open.
“What’s the rush?” He said, stepping in. “We’re good buddies with Billy!” Tim followed.
They grabbed her and immediately silenced any sounds she made with their hands. Hey eyes were wide with disbelief as they held her and dragged her into the living room and she was too shocked at the sudden intrusion to do anything. They were in too deep to turn back now, but that just added to the excitement. Being teenage boys, their hands roamed everywhere. Tim grabbed a handful of her shapely ass as the two pressed and rubbed themselves up against her, pushing her back into her house. She could feel Jeff’s erection through his pants as Tim kicked the door shut behind him and turned off the patio light to dissuade any more trick or treaters.
“Holy shit dude, grab a feel of her ass! It’s just like I imagined.” Jeff said, and he was right. It was incredibly soft, yet firm. He grabbed it roughly which made her squeal.
“Her tits are great as well!” Tim said excitedly, grabbing her with his free left hand as his right grabbed her other ass cheek. She was being utterly molested by these two boys and could feel their massive hard-ons through their jeans. Tim grabbed her pussy roughly which made her yelp, since the material was so thin.
Billy heard this from upstairs but dismissed it as her simply tripping, since she was kind of clumsy. Meanwhile, Amy was terrified, here were these two teenage boys, forcing themselves into her home. Her husband was out with friends, not that he’d be able to help anyway, small in size and cowardly as he was.
Billy, too, was always quiet and afraid. She was always the one who did the fighting for him, and at this moment he was in his room on the computer. She had no idea what to do. Her head buzzed with terror as Tim and Jeff took off their masks.
“Y-you!” She managed to stammer out. Jeff pulled her arm and then pushed her by her heaving breasts into the living room, she covered them up protectively as they both took a seat on the couch, put their feet up on the coffee table and made themselves at home. They already had everything pretty much planned out. They were big enough to stop her from doing anything too drastic and since Amy had never been in this situation before, she wasn’t entirely sure what to do.
“I want you to leave right now.” She said in hopeful defiance.
“Nah, I’d rather stay here for a bit.” Tim said, adjusting his crotch and leaning back.
“W-what do you want?” She said.
Jeff ignored her question and said “Why don’t you get me something to drink?”
She couldn’t believe it as she felt herself walk to the kitchen to fetch something, almost as though she were in a trance. In the back of her mind she thought maybe if she just gave them a drink they’d quickly leave, but she knew this wasn’t true. As her shapely ass jiggled while she walked away, Tim and Jeff knowingly smiled at each other trying not to laugh. They weren’t entirely sure what they were gonna do, but they loved being here, in another man’s home, molesting his wife and just taking charge of the place.
“She’s fucking terrified! She’ll do anything we want her to.” Tim said excitedly, already rubbing his cock at the thought. When she returned, Jeff smiled as he looked her up and down.
“Well, we want to work out a deal.” He said, taking a sip of her husband’s beer.
“What kind of deal?” She asked.
“You know we pick on your son, right?” Jeff asked rhetorically. “What if I told you we’d cut all of that shit out?” She wasn’t used to being spoken to like this, especially not by some 18 year old kid.
Frowning and feigning courage, she considered it. Even with this look on her face, she still looked flustered and cute.
“G-go on…” She said.
“All you have to do… is do us a few favours.” Tim chimed in slowly, rubbing his cock and smiling at her.
“Right…” said Jeff. “Just a few favours.”
“What kind of favours?” She asked, beginning to realize what these two perverts were thinking.
“Oh, I think you know what kind.” Jeff said, confidently. Looking her up and down, then smelling the lacy part of her genie costume that fell off.
It was only then that the realization fully hit her.
“Forget it!” She yelled, alerting her son. His heart jumped. “I want you to leave right now!”
This one sentence terrified Billy, slowly creeping downstairs.
“Hey, hey, no need to shout.” Jeff said, putting his feet up on the table and adjusting his cock. “It’s not like you even have any choice anyway. Hell, if I wanted I could fuck your pretty little face right now.”
This one sentenced tied Billy’s stomach in knots and left Amy speechless. He couldn’t believe they were speaking to his mother this way. His mother was equally terrified. She was good at putting on a brave face but the truth is she couldn’t stand up to these two.
“Why don’t you just make it easier on you and your son and just go down on me right now? Jeff said, uncrossing his legs and widening them, rubbing his cock. She stood terrified. Tim smiled.
“Do it.” He said, unzipping his pants. She still stood, frowning.
“And if I do this…” She began slowly. “You’ll leave my son alone?” She asked, unable to take her eyes off of his throbbing cock. There was something betraying her in the back of her mind. She hated these two. Loathed them. Was terrified of them… but she knew his cock was bigger than her husband’s.
Billy couldn’t believe she was even considering it. He wanted to rush in there but he was simply too afraid. All he could do was helplessly watch.
“Yep.” Jeff said, knowing full well this was a lie and trying to keep his cool. She reluctantly stepped forward. Inside Jeff was ready to burst and couldn’t believe this was happening, he was seconds away from getting his cock sucked by this woman. He knew it was his demanding and bullying nature that got him this far, that held her in his grasp.
“Hold on, bitch.” Jeff said. Her eyes widened at this change of tone.
“Strip down first. I don’t wanna get my dick sucked while you’re still fully clothed.”
She reluctantly began to slide off her pants. In a trance, she couldn’t believe she was doing this. Her tight purple sweatpants clung to her soft, smooth skin as she slowly undressed and made them all the more eager.
“Do it sexily. Slowly. Good. Now bring your sexy little ass over here and grind it up against me.” He carried on.
“G-grind…?” She asked. Still looking at his cock.
“Rub your ass against my cock you dumb slut.”
She slid her skin tight pants off and moved slowly over to him, she was only in her shiny purple silk underwear now.
“See, I told you dude.” Jeff said, referring to her panties. “She likes feeling like a real slut.”
Amy didn’t know what to say. She felt deep embarrassment at the way these two were talking to her which made her feel dirty. Part of her just wanted to get this over with.
“Bend over.” He said, leaning back. “That’s right, bring your ass over hear and rub it all over my cock.”
She slowly bent forward in front of him, her head still buzzed with terror and couldn’t believe she was doing this. He grabbed her waist and pulled her towards him. At least it wasn’t sex. She tried to rationalize by thinking this is the type of thing that could accidently happen on a crowded train.
“Ohhhh yeahhhh” Jeff groaned as she felt his erection through her soft, silky panties. “That’s it. Rub your ass around slowly. I bet your dumbass husband doesn’t even get this kind of treatment.” He loved the sensation of her soft, silky smooth ass massaging his cock and balls. He could feel her ass crack through her silk panties as he reached around and felt her pussy through the thin material.
Tim couldn’t take it. Her sexy body practically naked in front of them, the fact that they had total control over her in her submissive state. He unzipped his pants and took out his 7 inch cock. He was quite big for an 18 year old and Amy couldn’t hide her surprise as he pumped it up and down as he saw her submit to Jeff. He loved the idea of her being controlled. Jeff moaned in pleasure as her plump, soft ass did its work.
“Turn around. Take them off.” She did as she was instructed. She kept telling herself she just wanted to get this over and done with. She could feel his cock before but she only got an idea of how big it was when it was inches from her face. She looked at it nervously. Billy couldn’t take anymore and ran downstairs into the room.
“Mom! Stop!” Jeff immediately stood up and began to batter Billy.
“Stop!” His mother Amy screamed.
“You really want me to stop?” Jeff said, standing above a bruised and crying Billy.
“I’ll do… anything.” She meekly said.
Tim and Jeff’s cocks both got rock hard at this. This was their first experience of sex other than the porn movies that they regularly watched. And the fact that it was from the mom of the kid they both most detested, and that she was the object of their desires made them unbelievably hard.
“You can start by fetching something to tie this annoying shitstain up.” Jeff said, his pants around his ankles and his cock still sprung hard. She slowly got up and began to walk over to the kitchen.
“But before you go.” She stopped in his tracks. Jeff grabbed her hair and pulled it back as he kissed her roughly, sticking his tongue down her throat and making smacking noises in plain view of Billy, who sat frozen in fear.
“Oh fuck yeah.” Jeff said, pumping against her. This carried on for a minute or so as he lowered her to his knees and rubbed his crotch all over her soft face, leaving glimmering wads of pre-cum all over her.
“All right, bitch. Go get it.” He said, sending her off with a loud slap on the ass, laughing.
“Go get some of your panties, too.” Tim said. She nodded and quickly went off. Jeff used this opportunity to lean in towards Billy.
“We’re gonna fuck your mom so hard…” He began. “…and make her beg for our cocks.”
Tim laughed out. “The only reason I made her get her panties is so we can tie her up with them. And so I can jerk off to them later over this. A little souvenir. How’s it feel knowing your mom’s gone to get something to tie you up and stop you from letting us fuck her?”
They laughed. “If your dad comes home we’re gonna beat the shit out of him too. It’d get me off even more if he had to watch some kid fuck his wife right in front of him.” Jeff said.
Billy sat still, still frozen with terror and shame. Amy returned as Jeff kicked off his pants and shoes.