Ian's Guiding Light With Rex's Mom's Dilemma
by Chris nevermind
Copyright© 2025 by Chris nevermind
Ian and Rex have been best friends since grade school. Rex is 15 and Ian is 18, so they didn’t always attend school together, but they’ve lived next door to each other for years. They were always close, regardless of age. They got into the same things, and they talked about all of them. Ian recently moved a few towns over, but he came to visit Rex every weekend to catch up. Rex was a lanky kid, standing at 5’9”, with hair that was always uncombed. He wore T-shirts and jeans and, most of the time, didn’t even bother with underwear. He’d been known to skip showers, too.
Ian was 5’8”, athletic, and worked out all the time. He had dark features from his dad, who was Indian. Rex and Ian always had conversations that turned to girls, especially now that they were getting older and Rex was going through puberty. Rex had started growing hair in weird places—like around his asshole and balls—and it wasn’t that he was shocked by it; he just didn’t realize there would be so much.
Rex’s mom, Linda, was 36 and a little bit on the heavier side, but she had curves in all the right places. She had a big ass that any guy would die for and big, natural tits. Rex had gotten into the game in his mind where he’d hug his mom and she’d press her chest against him, and he loved the feel of them, the heat, but then he’d have to pull away because he’d get an erection.
Ian had always had a crush on Rex’s mom, Linda. Now that he was older, he made it more apparent to Rex. He made comments about Rex’s mom all the time. On this day, things escalated. The conversation went from talking about girls to Rex’s mom. Ian told Rex that if he really wanted to, he could fuck his mom. Rex laughed it off because they always talked like this. Rex said, “You have as much chance of fucking my mom as I do. It’s not going to happen.”
Ian looked at Rex and said, “I see the way you look at her. You have dirty little fantasies about her.” Rex laughed, but it made him really uncomfortable. He just laughed it off and turned red. Ian pressed further. “If you feel these needs and urges, these little fantasies about your mom, why don’t you go for it?”
The room got quiet. Rex realized his dick was getting hard in his pants. The conversation was turning him on. Rex said, “Because you’re crazy.” Ian said, “Am I?” Rex looked at Ian, and Ian said, “From what I’m seeing, I see a lump at the front of your pants. You cover it up with the game console. There’s no need to hide. Why don’t you go for it?”
Rex said, “Because you’re ... crazy.” Ian asked, “Why don’t you try it?” Ian continued, “When your dad goes to the UK next for a few weeks, and you have that Disney trip coming up, because he’ll be gone for 2 weeks, and then he’ll be gone another month, that’s your opportunity. Your mom’s not going to have any sex, and she might get horny. You know, like guys do.”
Ian was planting the seeds in Rex’s head. Rex couldn’t stop thinking about it. He thought, “It’s not like I can even go through with it, but...” He thought about it constantly. He thought about his parents when he wasn’t there, and his dad traveling all the time, and his mom being lonely.
Rex said, “What am I going to do when you’re not here?”
Ian hit Rex in the arm playfully. “Stop playing games; I won’t even know.”
Rex said, “But I don’t even know how to get girls at school. Getting women is different.”
Ian said, “It is, but you can be subtle. You’re her son, so you can touch her subtly. Hug her, kiss her on the cheek, and escalate.” Rex looked over at Ian, who was getting off on this. Ian could tell. He said, “I am. The idea of you and your mom gets me off like you’ve no idea, “ as he grabbed his dick through his shorts, which got Rex even harder.
Rex said, “Well, I don’t know, “ and at that moment, Linda poked her head in the room. “Do the boys need anything to drink?”
Rex said, “No, I’m good, “ and Ian answered, “I could use a glass of water.” She came in with a pitcher and a plate of chips and snacks, with two glasses. She set them down on the desk, bent over slightly, and Ian hit Rex in the arm to check out her ass. He whispered, “You can’t deny that ass.”
Linda walked by and patted Rex on the head as she left. “Let me know if you guys need anything.” She leaned in, whispering in Rex’s ear, “Whatever you want, “ and he laughed, and Rex jumped on the bed.
The following week, Rex couldn’t get Ian’s words out of his head. He called Ian to ask if he was serious about his mom. Ian laughed. “Of course I am. That’s fucking hot.”
Rex said, “I don’t know how to do it, “ and Ian said, “I’ll help you.” Ian instructed Rex to take it slow, start with a hug, and maybe a kiss on the cheek. Then, if it felt right, go for a kiss on the lips. Rex was nervous but excited.
The next day, Rex’s dad was leaving for his trip. He was going to the UK and then another month on the road. Linda had mentioned that she was planning to go to the gym, and Rex thought that would be a good time to try it.
Rex was home alone, waiting for Linda to get home. When she arrived, he heard the garage door open and her footsteps as she came into the house. He pretended to be on his phone, and she came over to give him a hug.
Rex hugged her back tightly, and for a split second, he felt her soft boobs against his chest. Linda pulled back, saying, “Have you had dinner yet?”
Rex answered, “Not yet.”
Linda said, “I’m making chicken alfredo. It’ll be ready in about 20 minutes.”
Rex nodded, and Linda turned to walk away. He tried to play it cool, but he couldn’t help staring at her ass as she walked out of the room. He felt his dick start to get hard again.
When she came back, she had changed into some comfy clothes—leggings and a T-shirt. She sat on the couch and asked Rex how his day was. They talked for a bit, and Rex started to feel more confident. He decided to try the kiss on the cheek.
He leaned in and gave her a peck on the cheek. Linda smiled and said, “What was that for?”
Rex shrugged. “I don’t know; it just felt like it.” Linda smiled, and Rex felt a surge of courage. He leaned in again and gave her another kiss on the cheek, this time lingering a little longer.
Linda laughed and said, “Okay, what
Rex went up to his room. He got on his cell phone and called Ian. “Hey, Rex, how’s it going?
Rex told him how it was progressing. “Well, she seemed to like it.”
Ian said, “See, it’s not that hard. Why don’t you try kissing her on the lips tomorrow?” Rex said, “Okay.”
The next day, Linda woke Rex up by shaking his shoulder gently. He opened his eyes to see her standing over him, smiling. He smiled back, still half-asleep. Linda said, “Good morning, sleepyhead. I made breakfast if you want some.” Rex nodded and sat up in bed. He could see Linda’s cleavage as she leaned over him. He felt his dick twitch. Adding to his morning wood
, he had a nice semi going. She kissed him on the cheek and left the room.
Rex got up and went to the bathroom. He took a piss and got in the shower. He tried to think about something else, but his mind kept going back to Ian’s words. He couldn’t help but wonder if it would work. After the shower, he went downstairs to eat breakfast. Linda was already sitting at the table, reading the newspaper. She looked up when Rex came in and smiled at him. Rex sat down and started eating.
They talked about Rex’s plans for the day and how his dad was doing on his trip. After breakfast, Linda told Rex she had to go to work. She kissed him goodbye and left. Rex texted Ian to tell him what happened. Ian replied, “Good job, bro. Now it’s time to take it to the next level. Go for that kiss on the lips when she gets home.”
Rex felt nervous but excited. He spent the rest of the day thinking about what might happen. When Linda came home, she was in a good mood. Rex was sitting on the couch, playing video games. Linda sat down next to him and asked him how his day was. Rex told her it was fine.
Linda put her arm around Rex’s shoulders and pulled him close to her. Rex could smell her perfume and feel the heat from her body. His dick started to get hard. Linda asked him what he wanted for dinner, and Rex suggested pizza. Linda agreed and got up to order it.
While she was on the phone, Rex got up and went into the kitchen to get a drink. When he came back, Linda was still on the phone. Rex went over to her and stood close behind her, looking over her shoulder as she talked.
He could smell her perfume again, and he felt his dick getting harder. Linda finished the call and turned around to face Rex. She smiled at him and asked if he wanted to watch a movie while they waited for the pizza.
Rex nodded, and she suggested they watch a horror movie that they both liked. They sat down on the couch together, and Linda put her arm around Rex again. Rex felt his heart racing. He tried to act normal, but he couldn’t stop thinking about kissing her.
About halfway through the movie, Linda got up to go to the bathroom. Rex took the opportunity to text Ian. “It’s going well. She’s being really nice to me.” Ian replied, “That’s good. Don’t forget to go for the kiss.”
Rex put his phone down and tried to focus on the movie. When Linda came back, she sat down next to Rex again and put her arm around him. Rex felt his dick starting to get hard again. He tried to adjust himself without Linda noticing, but she saw him moving. “Are you okay, Rex?”
Rex nodded. “Yeah, I’m fine.” Linda looked at him, concerned. “Are you sure? You look a little flushed.”
Rex felt his face getting hot. “I’m fine, Mom. I think I’m just a little tired.” Linda smiled and rubbed his back. “You’ve been working hard lately. Maybe you should go to bed early tonight.”
Rex shook his head. “I’m okay. I want to finish the movie.” Linda nodded and went back to watching the movie. Rex tried to calm down, but he couldn’t. He kept thinking about Ian’s words and the possibility of kissing Linda.
As the movie ended, Rex realized he had to make a move soon or he would lose his chance. He took a deep breath and leaned in to kiss Linda on the cheek again. This time, he lingered a little longer, feeling her soft skin against his lips. Linda turned her head slightly, and their lips met for a brief moment.
Rex pulled back quickly, feeling his heart race. Linda looked at him, surprised but not angry. “Rex, what was that?”
Rex tried to play it off. “I’m sorry, Mom. I didn’t mean to. It was an accident.” Linda looked at him for a moment, then smiled. “It’s okay, Rex. I know you didn’t mean anything by it.” Rex felt a wave of relief wash over him. Maybe he hadn’t messed everything up after all. Linda stood up and stretched. “I think I’m going to go to bed now. It’s been a long day.” Rex nodded, feeling a mix of emotions. He was relieved that Linda wasn’t mad, but he was also disappointed that he hadn’t gone further. He realized he would have to wait until tomorrow to try again.
As Rex got ready for bed, he couldn’t stop thinking about what had happened. He wondered if Linda had felt the same sparks that he had. He wondered if she would let him kiss her again. He fell asleep thinking about her lips against his.
The next morning, Rex woke up feeling nervous. He wasn’t sure what to expect from Linda after last night. He got dressed and went downstairs for breakfast. Linda was already in the kitchen, making pancakes. She smiled when she saw Rex. “Good morning, sweetie. Did you sleep well?”
Rex nodded, trying to act normal. “Yeah, thanks.” Linda put a plate of pancakes in front of him. “Eat up. I have a big day today.” Rex dug in, trying to focus on his food instead of his thoughts.
After breakfast, Linda told Rex she was going to run some errands. Rex said he was going to hang out with friends, and Linda reminded him to stay safe. Rex promised he would, and Linda left.
Rex texted Ian as soon as Linda left. “She didn’t seem mad or anything. She was really nice to me this morning.”
Ian replied, “That’s a good sign, bro. It means she didn’t think anything of it. Now you need to take it further.”
Rex replied, “I
Rex was on the phone with Ian when he saw his mom’s panties on the floor in her room. They were black and lacy, and Rex couldn’t help but stare. He told Ian what he was looking at, and Ian told him to grab them and smell them. Rex hesitated at first, but then he reached down and picked up the panties. They smelled like his mom’s perfume and something else, something more primal. Rex felt his dick get hard as he sniffed them.
Ian encouraged Rex to rub the panties against his face, and Rex did. He closed his eyes and imagined his mom wearing them. He pictured her taking them off and tossing them on the floor, and then him picking them up and smelling them.
Rex started to jerk off, still on the phone with Ian. Ian was telling him what to do, how to touch himself, and how to imagine his mom. Rex did what Ian said, and soon he was close to cumming. Ian told him to imagine his mom giving him a blowjob, and that pushed Rex over the edge.
Rex came hard, his cum shooting all over his mom’s panties. He was breathing heavily, and Ian was laughing on the other end of the line. Rex felt ashamed but also turned on. He realized that he had crossed a line, but he didn’t care. He wanted more.
Rex spent the rest of the afternoon thinking about what he had done. He knew it was wrong, but he couldn’t deny how good it felt. He felt like he was getting closer to his goal, and it was exciting.
When Linda came home,. They had dinner together, and Rex tried to focus on what she was saying. But all he could think about was her panties and how they had smelled. He wanted to touch her, to feel her skin against his. He wanted to taste her.
Rex realized that he was falling into a dangerous obsession. He was starting to see his mom as a sexual object, and it was affecting his relationship with her. But he couldn’t stop. He was addicted to the feeling of power and control he had when he thought about her like that.
As the days went by, Rex’s obsession only grew stronger. He started to masturbate more frequently, always thinking about his mom. He would imagine her in different scenarios, doing different things to him. He would think about her touching him, kissing him, and sucking his dick. He would picture her naked, her big tits and round ass. He would imagine himself inside of her, fucking her hard and fast. He loved the way she smelled and the way she tasted. He loved the feel of her skin against his.
One night, Rex had a dream about his mom. In the dream, they were in the kitchen together, and she was wearing a revealing dress. Rex was mesmerized by her cleavage, and he couldn’t take his eyes off of her. She noticed him staring and smiled, her eyes full of lust. She walked over to him and kissed him deeply, her tongue exploring his mouth. Rex was hard instantly, and he could feel her hand reaching down to grab his dick.
Rex woke up with a start, his heart racing. He was covered in sweat, and his dick was throbbing. He looked down and saw that he had cum in his sleep. He felt ashamed and disgusted with himself, but at the same time, he couldn’t deny the pleasure he had felt in the dream.
Rex knew that he needed to talk to Ian. He texted him and told him everything that had happened. Ian encouraged him to keep going, to push the boundaries even further. Rex was hesitant, but a part of him wanted to see how far he could go.
“I don’t know, Ian. This is getting too real. I’m starting to feel things for my mom that I shouldn’t be feeling. It’s not right.”
“Come on, Rex. You’re so close. Just a little further and you’ll have her. Once you’ve had her, you’ll feel better. You’ll be able to move on.”
Rex wasn’t sure if that was true, but he wanted to believe it. He wanted to think that once he had crossed that line, he would be able to forget about it and move on with his life. But deep down, he knew that wasn’t true. He knew that he would never be able to go back to the way things were before.
“I don’t know. I need time to think about it.”
“Okay, but don’t take too long. The longer you wait, the harder it’s going to be. And remember, your dad is going to be gone for a
Ian was pushing him, and he knew it. He knew that Rex was vulnerable and that he could manipulate him into doing what he wanted. And what Ian wanted was for Rex to fuck his mom.
Rex tried to put the thoughts out of his mind, but he couldn’t. They consumed him, haunting his every waking moment. He would see his mom walking around the house, and all he could think about was what she looked like naked. He would smell her perfume, and it would instantly turn him on.
One day, Rex was home alone when Linda came into his room. She was wearing a tank top and shorts, and Rex could see her nipples through the thin fabric. He felt his dick start to harden, and he quickly looked away.
Linda didn’t seem to notice. She told Rex that she was going to the store and asked if he needed anything.
Rex shook his head, trying to act normal. But as soon as she left, he closed his door and locked it. He pulled down his pants and started to jerk off, thinking about his mom’s nipples and what they would feel like in his mouth. He came quickly, shooting his load all over his hand.
After he cleaned himself up, Rex felt ashamed. He had masturbated to the thought of his own mother. He was disgusted with himself, but at the time, it had felt so good. He didn’t know what to do. He knew he needed help, but he was too afraid to tell anyone.
The next day, Rex decided to spend the day at Ian’s house. He needed to get away from his mom and clear his head. But as soon as he arrived, Ian started asking him questions.
“So, have you made any progress with your mom?”
Rex sighed. “No, not really. I’ve been trying to avoid her, actually.”
Ian raised an eyebrow. “Why? I thought you wanted to fuck her.”
Rex felt a wave of anger. “I do.
Ian said, “Look, I’ll go to your house. I’ll spend this weekend there. I’ll help you. We’ll come up with a plan. I’ll get a feel for her. I’ll tell you what I see, and then we can go from there. How does that sound?”
Rex hesitated, but Ian could tell he was tempted. He pushed a little harder.
“It’ll be fun, man. We can hang out and play video games, and you can try to fuck your mom. It’s a win-win.”
Rex sighed. “I don’t know, man. This is a really bad idea.”
Ian shrugged. “Maybe, but when has that ever stopped us before? Come on, live a little. It’ll be an adventure.”
Rex couldn’t deny that a part of him was excited by the idea. It would be dangerous and risky, but it would also be thrilling. And if things went well, he might finally get what he had been craving for so long.
“Okay, fine. You can come over this weekend. But if things start to go south, you have to promise to help me bail.”
Ian grinned. “Deal.”
That Friday, Ian came over to Rex’s house. Linda was happy to see him and welcomed him with a hug. Rex watched as she pressed her body against Ian’s, feeling a pang of jealousy. He wanted to be the one she was hugging like that.
The three of them hung out in the living room, watching TV and chatting. Rex tried to act normal, but inside, he was a nervous wreck. He kept wondering what his mom would do if she knew what he and Ian were planning.
As the night wore on, Linda started to yawn. She said she was tired and was going to bed. Rex and Ian said goodnight, and she left the room.
As soon as she was gone, Ian turned to Rex. “So, what’s the plan?”
Rex shrugged. “I don’t know. I haven’t really thought that far ahead.”
Ian rolled his eyes. “Come on, man. You have to have some kind of plan. This isn’t going to happen on its own.”
Rex sighed. “Look, I’ve never done anything like this before. I don’t know what I’m doing.”
Ian nodded. “Okay, that’s fine. We’ll start small. Right now, go get a glass of water and take it to her and just say you were thinking that maybe she might be thirsty and you didn’t want to have to get up to get it in the middle of the night, and give her a gentle kiss, and tomorrow, we’ll try something a little more daring.”
Rex nodded, feeling a surge of determination. It was now or never. He was going to do this, no matter what. He got up and went to the kitchen to get the glass of water.
As he walked down the hall to his mom’s room, he could feel his heart pounding in his chest. He hesitated for a moment outside her door, wondering if he should just turn back. But then he thought about how good it would feel to finally have her, and he steeled himself.
He slowly opened the door and peeked inside. Linda was lying in bed, her eyes closed. Rex assumed she was asleep and quietly walked over to her bedside.
He set the glass of water down on her nightstand and then leaned over to kiss her cheek. But as he did, Linda’s eyes fluttered open.
“Rex? What are you doing?”
Rex froze, his heart in his throat. He hadn’t planned for this. He didn’t know what to say.
“I ... uh ... I was just bringing you some water. I thought you might be thirsty.”
Linda smiled sleepily. “That’s sweet of you. Thank you.” Rex nodded and
Rex sat down and gently kissed her lips. Linda didn’t pull away, and for a prolonged second, their lips stayed together. Rex could taste her toothpaste and feel the softness of her lips.
Then, suddenly, Linda pulled back. She looked at Rex, confusion in her eyes. “Rex, what are you doing?”
Rex felt his face heat up. He knew he had made a mistake. He should have waited until she was fully asleep.
“I’m sorry, Mom. I don’t know what came over me. I just ... I had a dream about you, and it felt so real. I’m sorry.”
Linda looked at him for a long moment, and then she sighed. “It’s okay. But you shouldn’t be kissing me like that. I’m your mother.”
Rex nodded, feeling ashamed. “I know. I’m sorry. It won’t happen again.” Linda smiled softly. “I know it won’t. Now go to bed, okay?”
Rex nodded and got up to leave. As he walked out of the room, he glanced back at his mom. She was lying in bed, her chest rising and falling with each breath. Rex felt a pang of desire, but he pushed it away.
He went back to the living room where Ian was.
Rex told him what had happened. Ian was surprised.
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