Corrupting Jimmy Old Man Bob
Copyright© 2025 by Chris nevermind
Chapter 1
Fiction Sex Story: Chapter 1 - A boy discovering becoming a man with a helpful neighbor across the street with his mother and a father who has been neglecting them
Caution: This Fiction Sex Story contains strong sexual content, including Fa mt Reluctant Heterosexual Incest Mother Son
Jimmy walked through the front door and dropped his book bag onto the floor. Old man Bob from across the street yelled over for him to come talk. Jimmy ran over and waved at the man; he always liked talking with Bob. He was a very nice guy; he always had candy, a soda, or just a good old tussle of the hair for him. Jimmy walked over and sat in a chair next to him. Bob asked how his first week of high school was, and he said it was going well. Bob asked if he had any girlfriends yet, and he replied no. Bob then asked if he was looking for girls that looked like his mom. Jimmy was taken aback by the question. He didn’t know how to respond; all he could muster was, “What?” Bob laughed at him. “It’s okay, you know,” he said. Jimmy felt blessed, and his ears turned red. He didn’t know what to do. Bob didn’t want to make him feel bad, though, and quickly changed his plans.
“It’s okay; we all do that,” Bob said. “Boobs are boobs. Women have boobs. Your mom’s boobs have gotten bigger. You’re lucky because you get to see them every day. Who knows, maybe one time you’ll get to see them without her bra or her blouse on.” Jimmy looked at the ground and felt uncomfortable. Bob pulled back from him with his innermostwindows and said, “You know, Jimmy, you’re my best friend.” Jimmy was really unsure if this was true. “Yes, absolutely! So you can tell me anything. And I will tell you anything. Deal?”
Jimmy thought for a while, then responded, “Deal.” Bob then said, “Now I want to tell you a little secret that your mom told me. When she went and got her breasts enhanced, she told me that she had to take them off her bra for a few days so they could heal. She had to go topless around the house. I asked her, ‘What about Jimmy? Won’t that make him uncomfortable?’ And she said, “Oh, Jimmy won’t mind; he’s a good kid and will understand that she is healing.” Jimmy had no idea that his mom had been topless in the house for a few days after she got her boobs done. Bob looked at Jimmy’s confused face and said, “See, Jimmy, your mom thinks you are mature enough to handle her topless. You must be
Jimmy felt a tingling go up his spine. He wasn’t sure what it was, but he also felt his dick move in his pants.
“Hey Jimmy, I have a little challenge for you.”
Jimmy looked at Bob and said, “Yes?”
“I want you to see if you can see your mom without her bra and blouse on, okay? It’s a little game.”
Jimmy thought about this for a while. He could tell Bob was looking for an answer. “I’m not sure. I mean, it would be kinda weird.”
“It’s okay, Jimmy, I know it’s a little weird. But you can do it. I believe in you. Plus, I’ll give you whatever you want. if you do.”
Jimmy looked back at the house and then back at Bob. “I can’t promise you, but I will try. But I am not saying I will do it.”
Bob smiled and said, “That’s all I ask. Just try. That’s all you can do.”
Jimmy got up from his chair and walked back across the street to his house. He opened the front door and walked inside. The house was quiet. His mom must be in her bedroom. He slowly walked down the hall to the room, but her door was closed. She must be taking a nap. Jimmy quietly walked back down the hall and into the living room and plopped down on the couch. He started thinking about what Bob said. It didn’t seem like a good idea, but on the other hand, his mom did say that Jimmy would be mature enough to handle it. So it would be okay, right? Jimmy got up from the couch and walked back down the hallway to his mom’s room. The door was still closed. He slowly walked to the door and leaned in to listen. He couldn’t hear anything. Jimmy slowly grabbed the handle and started turning it, but then he stopped. He didn’t want to walk in on his mom asleep. Jimmy turned away from the door and started to walk back down the hall.
“Jimmy,” his mom yelled from the room. Jimmy stopped. “Come in here for a second.”
Jimmy grabbed the door handle and opened it. His mom was standing there in a white blouse and blue jeans. She was smiling but also had a concerned look on her face. “Are you okay, sweetie?” Jimmy looked at her. Her blouse was buttoned up all the way to the top, and he could see that she had her bra on. She walked over to him and gave him a big hug. “Is your first week okay? I know you’re not used to the longer hours and the harder work. I also know you miss your friends from middle school. It’s okay to miss them. It’s also okay to make new friends.” Jimmy hugged her back. She smelled of perfume and hair spray. Jimmy’s mom was always at the salon, cutting, dyeing, and perming hair. She was the owner of a small salon downtown and was always smelling of those chemicals.
Jimmy’s mom pulled back and said, “I know this is a big change, but it will be okay. You’re doing great. I know you are.” She leaned in and kissed him on the cheek. Jimmy looked at her and said, “It’s going good.” She smiled and walked away from him to the bed. “Now strip down and let’s get ready for bed, okay?”
Jimmy turned around and started to walk out the door. “And Jimmy?” He stopped and looked back at his mom. “I know you’re going through a lot of changes right now. If you need any help or have any questions
He was going through his own changes. His own body was changing. His ass was getting hairier. His balls were getting hairier. He even had some chest hair and armpit hair. Which he wasn’t even aware of. There was going to be so much hair! And his mom, with her big boobs, and across the street, Bob, old man Bob, seeking ideas in his head. He was going through so many changes, and his dad was always working. Which was really starting to bother Jimmy. More than he thought it should.
Jimmy walked into his room, which was across the hall from his mom’s and next to his dad’s. He turned on the light and closed the door. He then started to undress. His shirt came off first, revealing his hairy chest. Then he dropped his pants and underwear. He was standing there naked, with his penis slightly erect. He looked at himself in the mirror, which was on the back of the closet door. Jimmy didn’t think he looked like a man. He looked more like a boy. His penis was semi-erect now and looked to be getting bigger. He grabbed his penis and started playing with it. He looked back at the door to make sure it was closed and then turned back to the mirror. He was stroking his penis, and it was getting harder. He had masturbated before, but never in front of a mirror. It felt different, more exciting. He looked down at his balls, which were also starting to get some hair. He grabbed them with his other hand and started playing with them. His penis was now fully erect, and he was stroking it up and down. Jimmy felt so good. He loved this feeling, but at the same time, he hated it. It made him feel like a pervert. He stopped stroking himself and looked at his penis. It was still erect, but now he felt bad. He put on a pair of boxers and a t-shirt and then crawled into bed. He turned off the light and lay there in the dark, thinking about the day. He thought about Bob and what he said and how he felt when Bob said it. He thought about his mom and how she looked. And then he started to think about how her boobs looked. How they would look without her blouse and bra on. He imagined them, and before he knew it, his penis was erect again. He tried to stop.
When Jimmy came home and saw his mom naked in the bathroom, she wasn’t aware that he was home. She hadn’t heard him come in. He was looking through the crack of the bathroom door. There was a small plant in the way, but if he looked at a certain angle, he could see her, but she couldn’t see him. His mom was naked. She was stepping out of the shower. Her body was beautiful. Her breasts were big and round, with huge pink nipples that were the type you could suck on for days. Jimmy had an erection. It was huge. He didn’t know what to do. He got his mind off of it. Jimmy went outside. After seeing that, his mom started walking around the house naked. He scrambled to go outside. Old man Bob must have caught a glimpse of them, because he called them over again. Jimmy was going to give it to him. He was. Bob was going to ask what Jimmy’s mom’s body looked like, how big her boobs were, and if she shaved her pussy. And asked if Jimmy was interested in exploring her body. Like fucking her. Jimmy was going to tell Bob that he was a virgin. That he had never been with any girl. Besides masturbating.
Jimmy walked over to Bob’s house. The man was sitting there, smiling. “What’s up, Jimmy?” Bob said.
“What’s up?” Jimmy said. He was feeling a little shy. But he knew that Bob was his friend. He could trust him.
“Did you try it? Did you try to see your mom without her blouse and her bra on?” Jimmy looked down. He felt ashamed. “It’s okay, Jimmy. I know it was a little weird, but you can tell me.” Jimmy looked up at Bob. He looked like he really wanted to know.
“I tried. I walked into her room, and she was there. She said I looked troubled. She gave me a hug and kissed me on the cheek.”
“Then what happened?” Bob asked. Jimmy could tell that he was getting excited.
“I started to leave the room, and she told me to take off my clothes so that we could get ready for bed.”
“Okay,” Bob said, “then what?”
Jimmy looked around and then said, “I went to my room and took off my clothes and got into my boxers and t-shirt. Then I got into bed.”
“Jimmy,” Bob said, “that’s it?”
Jimmy looked down again. He didn’t say anything.
“I thought we were friends. I thought that you would tell me anything.”
Jimmy felt bad. He looked up at Bob and said, “She walked down the hall from her room to the bathroom. She was naked.”
Bob’s eyes got big. “Really?” he said.
Jimmy nodded his head.
“She was walking around naked?” Bob asked.
“Yes,” Jimmy said. He felt better getting this off of his chest.
“Did she have big nipples? The kind you could suck on for hours?”
Jimmy nodded his head again.
“Did her boobs sag, or were they firm?”
“She had firm boobs. The kind that you could play with for hours.”
Bob looked at Jimmy. “Jimmy, you are my best friend. You can tell me anything. Now I want you to do me a favor.”
Jimmy looked at him. He was curious about what he was going to say.
“Next time you see your mom naked, I want you to touch her boobs.” Jimmy didn’t know what he was hearing. He must not have heard him right.
“What?” he said.
“When you see your mom naked next time, I want you to reach out and touch her boobs.
Bob looked at him. “Look, you’re becoming a young man. You are already growing hair, and in some spots I’m sure. Your balls and your ass are all up your crack. Your armpits—your voice is changing. You’re becoming aware of women, even if it is your mother. If things turn you on, you always should go for them.” Bob even knew that the words that were coming out of his mouth were not good advice. He didn’t care. He just wanted to hear more about this bitch across the street and her big tits. Now Jimmy was on his way in.
“These are things that men go through. To feel good. Seeing your mom like that, did it get your dick hard? Which I’m sure it did. But Jimmy, you can tell me anything, anything at all.”
Jimmy was silent for a second, then he said, “Well, when I was in my room and I took my clothes off, my penis got hard. I touched it. Then it got even harder.”
Bob looked at Jimmy and smiled. “Did you play with it for a little while?”
Jimmy nodded his head. “Yes.”
“How long?”
“About five minutes.”
Bob chuckled. “Well, that is nothing to be ashamed of. That is natural. We all do it. Even your mom and dad.”
Jimmy thought about what he just heard. He had never thought about his parents masturbating. It seemed weird. But then again, he guessed it wasn’t.
“Now Jimmy, when you saw your mom naked,. What did you think when you saw those big, round boobs? With those big, pink nipples?”
Jimmy looked at Bob. He didn’t know if he wanted to answer that question or not. But he trusted Bob. He knew it would be okay.
“Well,” he started, “my penis got really hard. And it felt funny. But it also felt good.”
Bob smiled. “It felt funny, but good?”
Jimmy nodded his head again. “Yes.”
Bob laughed. “I knew it. Your mom is sexy. Even at her age.”
Jimmy didn’t say anything. He didn’t know what to say. But then he felt something. He felt his penis start to get hard. Just the thought of his mom naked was doing something to him. Something that he wasn’t sure was right or wrong. But it was definitely something.
“Hey Jimmy,” Bob said, snapping him out of his trance, “I have something for you. You’ve been a good kid. You deserve it.”
Jimmy looked at Bob. Bob was standing up and walking into the house. A few seconds later he came back out holding a small gift box.
“Here you go,” Bob said. Jimmy took the box. He opened it up, and there was some candy and a couple of magazines. Jimmy looked at the magazines. They were women with big boobs. Very big boobs. Some of them were topless.
“Thanks, Bob,” Jimmy said, trying to hide his excitement.
“You’re welcome. Now listen, I have to go to the store. Can you watch the house for me? I shouldn’t be gone for more than an hour. Okay?”
Jimmy nodded his head and said, “Okay.”
“Good,” Bob said, getting up and walking to his car. “Remember, if you see your mom naked again. Go for it! Touch her boobs! You only live once.”
Bob got into his car and started the engine. He backed out of the driveway and drove off. Jimmy sat there for a second, just looking at the house. Then he went inside. It was nice and cool in there. And quiet. Jimmy walked over to the couch and sat down. He looked at the box in his hand. The candy and the magazines. He took one of the magazines out and flipped through it. There were so many pictures of women with big boobs. Some were topless. Some were even fully nude. Jimmy felt his penis start to swell. He couldn’t stop looking at the pictures. Some of the women were even spreading their legs, showing everything they had. Jimmy started to feel a little overwhelmed. But at the same time, it felt so good. So he kept looking at the pictures.
Jimmy was so wrapped up in looking at the magazines that he didn’t hear the front door open. And he didn’t notice that someone had walked into the house until they were standing right in front of him. It was his mom. She was home.
Jimmy looked up at his mom, who was looking at him with a concerned look. He quickly shut the magazine and put it back into the box. “What are you doing here, Mom?” he said. “I thought you were at work?”
His mom just kept looking at him. She didn’t say a word. Jimmy got worried. Did she see the magazines? Did she know what he
“I’m here because I was worried about you. I was driving by and didn’t see you anywhere. I saw your head through the window, sitting on the couch. What’s going on? What are you doing in Bob’s house?”
Jimmy felt a little nervous. “He asked me to watch the house for him. He had to run to the store.”
His mom nodded her head. She seemed to accept that answer. “Okay,” she said. “Just make sure that when you are done, and Bob comes back, you come home. Your dad should be home soon. Maybe he’ll be home early enough to eat dinner with us.”
Jimmy could tell that his mom was annoyed about something. She always muttered to herself when she was annoyed.
“Why is Dad never home? We have no love life,” she said to herself. Jimmy wasn’t sure what that meant, but he made a mental note of it. That was about it.
His mom looked back at him and said, “Jimmy, I’m going to head back home. Make sure that you come home as soon as you can. Okay?”
Jimmy said okay and watched as his mom walked back out of the house. He heard the front door close and lock.
Bob came home an hour later. Jimmy had been flipping through the magazines the whole time. He learned so much about women. About their bodies, their breasts, and their vaginas. It was almost too much to take in. But he couldn’t stop looking. When he heard Bob’s car pull into the driveway, he quickly put the magazines back into the box and closed it up.
Bob walked into the house and saw Jimmy sitting on the couch. He smiled. “Hey, Jimmy! Thanks for watching the house. I owe you one.”
Jimmy smiled back and said, “It was no problem. But Bob, can I ask you a question?”
“Sure, what’s up?”
“My mom, she was here a little bit ago. She said that my dad and her have no love life. What does that mean?”
Bob looked at Jimmy for a second. Then he smiled. “Well, Jimmy. That means that they are not having sex.”
Jimmy thought about that for a second. “What? Why not?”
Bob shrugged his shoulders. “Sometimes married couples don’t have sex as much. But that could be an opening for you.”
Jimmy wasn’t sure what Bob meant by that. But he was about to find out.
The next morning, Jimmy woke up and got dressed. He went downstairs to the kitchen to eat some breakfast. When he got there, his mom was already at the table, eating some cereal.
“Good morning, Jimmy,” she said. Jimmy said good morning back and sat down at the table. His mom got up and got him a bowl and spoon and the cereal. She sat back down, and they both started to eat. Jimmy couldn’t help but notice that his mom was wearing a low-cut blouse. He could see a lot of her cleavage. And her breasts looked so big. He tried not to stare, but he couldn’t help it. He was starting to get aroused.
“So Jimmy,” his mom said, breaking the silence, “how was your first week of high school?”
Jimmy snapped out of his trance and said, “It was good. Just getting used to the schedule and the new teachers.”
His mom smiled. “That’s good. I’m glad to hear that.”
Jimmy went back to eating his cereal. He couldn’t help but sneak a peek at his mom’s breasts every now and then. He wished that he could see them without her bra and blouse on. He started to think about what Bob had said yesterday. That he should try and touch them. Jimmy didn’t think that was a good idea. But at the same time...