Timmy's Mom - Cover

Timmy's Mom

by JDlit71

Copyright© 2025 by JDlit71

BDSM Sex Story: Timmy's Mom discovers his long time friends are not so friendly...

Caution: This BDSM Sex Story contains strong sexual content, including Ma/Fa   Teenagers   Blackmail   Coercion   Consensual   NonConsensual   Heterosexual   Fiction   BDSM   MaleDom   Light Bond   Rough   Sadistic   Anal Sex   Cream Pie   Double Penetration   Public Sex   Size   .

Olivia sat fuming as she listened to her son talking about his day at school. He was in trouble for something that wasn’t even his fault, but he couldn’t get anyone to believe him.

“Mom, I’m telling you that they have been bullying me all year and I’m sick of it,” Tim said.

“I believe you Timmy, I just don’t understand? These are your three closest friends. Why are they–”

“Mom. They are not my friends. Jimmy was my friend, but Harry and Mitch have always been mean to me. I don’t even want to tell you what they’ve been doing to me. It’s too embarrassing,” Timmy explained.

“But I can’t help you if I don’t know what’s going on at school,” Olivia said, trying to help.

“The problem’s more after school than it is during school. I can get away from most of that stuff when I’m at school. Except for the mean girls. It’s after school and on the way home that’s the problem. These guys know how to play you,” he said, hoping his mom would drop it.

“What do you mean they’re playing me? Those boys come over and study with you at least twice a week, right?” she asked.

Tim didn’t answer that question. If she knew what they were doing to him, she would freak out.

“I just wanna go get some sleep, ok mom?” Tim said, whining.

“Ok sweetheart. Get some rest and we can talk about it tomorrow if you want. Remember, you can talk to me about anything. Any - thing. Got it?” she said, trying to reassure him.

“OK mom. Good night,” Tim said as he went upstairs to his room.

Olivia spent the next hour, combing the labyrinth of several social media platforms trying to track down Jimmy, Harry, and Mitch. She had used their check-ins to narrow them down to a hideout that they posted from over on Fourth and Connor streets. It was not a good neighborhood and definitely not the kind of place anyone should be at night. Olivia was angry and sick about Timmy and his situation, particularly at school. Timmy was an excellent student and he had a real chance to be valedictorian of his class, but not if he was in trouble. She knew Timmy wouldn’t get himself into any real trouble. He wasn’t that kind of boy. There had to be more to it. Olivia was determined to get to the bottom of it. She was so focused and angry that she completely forgot that she wasn’t fully dressed as she left the house.

She pulled up to the house that was posted online. They called it “The Bitch Bunker”. This made zero sense to Olivia, but her mind wasn’t thinking about the name of their little hideout. She wanted information about why Timmy was in trouble and why his friends weren’t sticking up for him.

She walked up and knocked on the door of the single story brick & stucco house that was in serious disrepair.

“Yeah?” Jimmy said, opening the door. He was standing in his underwear trying to clear the sleep out of his eyes. “Oh, hey Mrs. O. What’s up? Is Timmy with you?” he asked as he studied Olivia’s massive titties and her shapely ass. She looked really hot standing in the doorway.

“No, Jimmy, he’s not. I need to talk to you about him though. Do you have a minute?” Olivia asked.

“Well, sure, I guess so. You wanna come in? Harry and Mitch are here. We’re just hanging out before we head home. Come on in, make yourself at home,” Jimmy said, licking his lips.

“Thank you Jimmy. I appreciate it,” Olivia said as she walked in.

The living room was sparse with furniture. The room only had a couch, a rocking chair, an ottoman, and a rug. There was a large TV mounted on the wall. She didn’t notice the porn scene that the boys were watching, she was more focused on Harry and Mitch. They were also in their underwear, sitting on the couch. Both boys were drinking beer. She was stunned. They weren’t even trying to hide it from her. They all three just stared at her, waiting for her to talk.

“Well,” she began nervously, “I understand that Timmy is in trouble at school, but he won’t tell me why. I think you boys know why. First, I want to know why he’s in trouble, but more importantly, why aren’t you boys backing him up? You all know Timmy, he’s a good kid. What could he possibly be in trouble for?”

“You should probably ask him, Mrs. O. I don’t think it’s my place to talk about his sex habits. Do you think we should be talking about Timmy’s sex habits, Harry?” Jimmy asked.

“Nope. I’m definitely not going to talk about what he’s doing to those cheerleaders,” Harry said with a smile.

“What about you Mitch? You wanna tell her about Timmy’s dirty little secret?”

“Nope. What them cheerleaders do to his balls is his business. I’m not getting involved,” Mitch said as he sat on the couch rubbing himself.

Olivia suddenly realized that all three boys were stroking themselves through their underwear and getting hard. She started to blush, but kept herself calm.

“What’s this about cheerleaders? Timmy’s never been involved with any cheerleaders. He doesn’t even have a girlfriend. Does he?” Olivia asked.

“Well,” Jimmy said as he casually walked over and locked the door. “I don’t know if there’s a girlfriend, but there’s several girls and I think they’re all friends. Just like you and I are friends, right, Mrs. O? I mean, we’re pretty tight, wouldn’t you say? Otherwise, how would you know that we hang out here? Unless maybe you come by and keep us company a lot, right?” Jimmy said as provocatively as he could manage.

“Well, no? This is the first time I’ve ever been here. You boys know that,” Olivia said trying to figure out where this was leading.

“Well did Timmy tell you about this place?” Mitch asked.

“Well no, of course not. He doesn’t even know I’m here,” Olivia confessed.

“So how did you find us?” Harry asked.

“Well, I just did a little digging on a couple of social media sites and–”

“You stalked us, Mrs. O? Jimmy said interrupting. “You searched around and found your son’s buddies hideout and just happened to show up while they were having a porn party? Tsk, tsk, tsk. Mrs. O. Do you want to know how that looks? I mean, you’re over here practically seducing three young men, under 21? I don’t think you’re helping Timmy very much. It kinda looks like a family thing, what with Timmy getting those cheerleaders to sign his balls in permanent marker? Now here you are getting us to undress down to our underwear? Or less?”

All three boys suddenly slipped out of their underwear and stood around Olivia naked. She was frozen. What was she thinking? These boys could get her in real trouble. They were all underage and she was an adult. Now they were all naked.

“Say hello!” Harry said, waving to the camera mounted in the corner of the room pointing directly at her.

“I think you’re way overdressed, Mrs. O. Don’t you think you’d be more comfortable naked?” Harry said as he took a step back.

“Look, you boys are out of line here. You need to put your clothes back on. I’m going to leave and we’ll never talk about this again, ok?” Olivia pleaded.

“Tell you what Mrs. O. You strip down right now and blow all three of us, and we’ll let you go home, free and clear,” Jimmy said with a smile as all three boys moved in closer to Olivia.

“No, really, I didn’t come here–”

“Why did you come here Mrs. O?” Harry interrupted as he put his hand on Olivia’s shoulder.

“Yeah. You haven’t had any dick in a year. Timmy told us. Your husband is out on the road driving a truck. You came here for a gang bang didn’t you, Olivia?” Mitch touted, grabbing her ass.

“I don’t–”

“I think you do, Olivia. I think you have dick on your brain right now. I’ll bet you’re wet right now just standing there,” Jimmy said as he pulled up Olivia’s skirt and stuck his finger inside her pussy.

He pulled his shiny wet finger out and stuck it up towards the camera.

“Oh you’re wet alright. And no panties? You obviously came here for all three dicks, didn’t you?” Jimmy said as he pulled her skirt off.

The other two boys quickly stripped off Olivia’s top and revealed her massive titties and no bra. They shoved her down to her knees and Mitch grabbed her hair as he used it to guide her mouth onto his 9” cock. She tried to push him away, but Harry stuck two fingers into her cunt and began finger fucking her. She suddenly slipped up and moaned as the boys took control of her. Jimmy was mauling her big 36 DD melons and pinching her nipples while Harry continued fingering her.

It was no time before she began creaming on Harry’s fingers. He pulled them out and wiped them on her long black hair, then shoved them into her ass. Mitch pulled out of her mouth and laid down in front of her with his legs sprawled out on either side of her shoulders. She instinctively leaned over and continued sucking him. The camera caught all of it.

As she was bent over sucking Mitch, Harry mounted her from behind and drove his dick into her ass as she screamed into Mitch’s cock. Harry plowed into her ass hard and fast while Jimmy pinched her nipples and made her moan.

“I think this slut needs some jewelry,” Jimmy said as he quickly left the room.

He returned and sat on the floor next to Olivia and adjusted the clover clamps and attached each one to her nipples. She writhed in pain and squealed as Jimmy adjusted them about twice as tight as they needed to be. They weren’t coming off. The pain in her nipples transferred directly to the muscles in her pussy as Harry moaned with delight. Mitch’s cock was still lodged in her ass, but he felt the pressure as well and this got them both pounding her again.

As they hammered her ass and pussy, her big floppy tits began bouncing hard. The clamps made a clinking sound as they began flailing about while Harry and Mitch wrecked her holes. Jimmy grabbed his phone and began taking video of Olivia as she began moaning and howling while the two fucked her harder and harder.

As the two young men unloaded their spunk into Olivia, Jimmy captured every moment on his phone.

“Wanna see a magic trick?” Jimmy asked Olivia.

Jimmy reached behind the sofa and brought out a massive cock extension. It looked like a horse cock. It was 16” long and 3” around at the end. He strapped it around his waist and slid his cock inside the fake dildo. He shoved Olivia down on her back as Mitch and Harry grabbed her ankles and spread her legs out until she was wide open. Jimmy slammed the fake cock into her cunt as she screamed briefly before passing out from the pain and pleasure.

 
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