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A son peeps in his mother's life and everything changes.
4.1k words
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Part 1 of the 2 part series

Updated 06/10/2023
Created 04/07/2021
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dorry123
dorry123
83 Followers

Max paced the room in agony thinking that this was unacceptable, 'How can her own mother do this to him? Especially after everything that they have gone through.'

Max lived with his mom. His dad left them when he was nine and well, he was not a very nice guy. Max's mom, Julie had her own job and they lived comfortably enough. And Max didn't have any complaint. He liked staying with his mom. And as his puberty kicked in, all his friends had a crush on his mom. And he thought to himself, 'Why not? His mom was hot. She was pretty, had golden hair, was curvy without being voluptuous and Max thought she had the best boobs in the world. Soft, cushy yet firm' - Max fixated on them. And so, he was actually proud that all his friends had a massive crush on her.

Actually, one day, when he was eighteen or so, he got up to some sounds coming from his mom's bedroom. He tiptoed to the room and heard voices coming from beyond the door. It was his mom's voice and there was a guy's voice too. They were moaning, giggling - Max got curious. Max peeped through the keyhole and the room was dark but what little he could make of was his mom didn't have any clothes on and she was giggling and a guy was touching her. He stood there hearing his mom moan, trying to peep hard. That was the first time he thought of her mom as a sexual being and was equally fascinated and disgusted to realize he had a raging hard-on.

This was strange for Max. His mom sometimes had friends over and rarely did they stay the night. He never imagined his mom having sex with someone. And yet, as he saw it, it gave him a hard-on.

Over the next year, he clearly knew what was going on. He had seen porn with his friends. Yet, strangely every time he masturbated even after watching porn; he wasn't thinking of the porn. He thought of his mom and some guy. It was good as long as he cum. But, immediately after he had jerked off, he had a pang of massive guilt about what he was doing. The more he tried to think of his mom as just his mom, all he could think was how resplendent she looked naked. Since they have stayed together for some time, her mom roamed around the house in her nightgowns and occasional lingerie sometimes when she's in-between some work. And Max had those images imprinted in his head. The jiggle of her boobs, the nipple pokes, the cushy ass, her svelte figure - and if it was not enough, now he also has heard him moan and cry out in pleasure. The only respite he had was that his mom rarely had guys stay over. And whenever he peeped into her room when she was with someone, the lights were always off.

Max's college was a little far away from his place. Max juggled between staying at a friend's place near the college and being at home. One weekend, Max sat down for a breakfast with his mom. Julie, as usual, wore a loose housecoat with just a knot that barely contained her boobs. Max could figure the nipple and strangely she was not wearing anything other than the housecoat. Julie stared at her before she said

'Do you like it?'

'What?' Max was still sleepy.

'I know you stay outside my bedroom whenever I have someone over.'

Max's ears pricked as he sharply looked at his mom. Julie's face didn't show any emotion that Max could decipher. He said, 'What?'

'I know you sneak up to my bedroom time and again at night.'

'I am sorry.'

'Why are you sorry? I am your mother. It's okay.'

Max looked up. Her mother didn't seem angry. Max's eyes instinctively went down to trace her boobs.

'I am sure you know what goes on?'

'Mom, I know.'

'Okay. And do you like it?'

Max didn't know what to say. 'Why are we talking about this? I said I am sorry.'

Julie looked up and said, 'Well, you're in college. We should be friends now. I want you to know as much of my life as I want to know about yours. And I don't want any secrets between us. Look, we only have each other. And we have to be honest with each other. I have sex with men sometimes. It's okay. You're my son. You are well within your rights to check up on me and see if I am safe'

Max didn't know what to say. He kept his head lowered.

'Well, Max. It's okay. We must start discussing all these.'

Max murmured, 'I didn't know you knew about it.'

'Tell me, Max. Do you like it? Why do you stand for so long?'

'I don't know.'

'I do.'

Max didn't reply. He felt so embarrassed and flushed.

His mom went on, 'Do you have a girlfriend?'

'No, mom.'

'Why? You're handsome, you're in college. Girls must be drooling over you.'

'Haha! I don't know. I don't think I have ever clicked with anybody.'

'It's okay, baby. There is no need to rush into anything. And just so you know, I feel safe that you're there watching me and that you're there if I need you.'

Julie came forward and hugged him tightly. Max could feel her mom's boobs a little away from his face. Max felt a little bold, He adjusted his face and lay it directly on her boobs. Julie pressed his head closer.

After that, Max usually tried to be at home. He liked spending time with his mom. They watched the occasional TV or went out to eat. While Max always had an arm around her, neither did Max try anything inappropriate neither did Julie do anything uncomfortable.

One day, Julie had a friend over. He was different from the other guys. His mom was dressed up. She was wearing the silk housecoat and she wasn't wearing any bra. Max could tell as the boobs swayed when she walked. The guy who came over was old and he seemed nervous. By then, Max knew what would happen next. As mom set out dinner, he finished it quietly and went off to his room. His mom came and said, 'Good night sweetie.'

Max said, 'Mom, is he going to stay over?'

His mom said, 'I think so. Let's see how the dinner goes.'

Max nodded and he got busy on his computer. His ears were pricked and he knew by the sounds, they were still in the living room. He peeped through his room's keyhole but it led to the corridor. He waited patiently till he heard the click of her mom's bedroom.

He waited for some time, tiptoed and peeped in. To his surprise, the lights were on. His mom was lying naked with her legs open. She was completely shaved and she was glistening. Her eyes sparkled with sensuality. Ahh, she looked delicious everywhere. The guy also probably took in her naked mom as he stood. He was still wearing his shorts. Slowly, he came towards his mom and went down and started licking her pussy while his hands were on her boobs. Oh, how he fondled them!

Max was feeling angry and yet, he was so turned on. He couldn't believe what he was seeing. He was hard as he saw the guy lying on the bed stroking his big, hard cock. His mom slid his cock in her mouth. Max exploded in his pants and he must have made a sound because his mom stopped. Max rushed to his room and pretended he was asleep. He could hear his mom open the door of his room and standing near him. She bent down and kissed his cheek. She smelled different. She stroked her hair and left.

Max wanted to go stand outside and look into her mom's bedroom again but he didn't want to get caught.

His mother woke him up the next morning. She was wearing a loose shirt. She asked him to move and laid down by his side. She slid her arm across him. Julie smiled and stroked his hair as she turned towards him, he could see three of the top buttons were undone.

Max didn't know what he was feeling. Was he angry? Was he excited?

He asked, 'Mom, what are all these marks?' Max traced her hand on numerous red spots on her boobs.

'Well, I got kissed hard there.'

'Did it hurt?'

'Why do you want to know?'

'Tell me.'

'I think you saw it all.'

'I didn't. And I want you to tell me.'

'It hurts now. At night, it just made alive.' Max leaned closer to her and undid the other buttons. Julie didn't prevent him. Max pressed his lips against the biggest hickey on her boob near the nipple. Julie pressed close.

Max mumbled, 'You do smell different.'

Julie took his leg and put it over her and pressed him closer. Max was aware of his erection and he knew his mom was too. But, no one spoke and Max kissed her boobs exactly over the red spots. Max kissed them frantically as he tried getting closer to his mom. He could only imagine what the guy was doing. Did he suck her nipples hard? What else did he do? As he thought of these things, he came hard in his pants and he immediately retreated from his mom. He thought his mom understood as she got up, kissed his forehead, buttoned up her shirt and asked him to come to the breakfast table.

From that day on, Max always felt more closer to his mother. They finally started speaking more freely about everything. But, never did they discuss what happened that morning. Nor did Max try to get close to her mom physically. But he jerked off more violently than ever as he thought of his mom licking the cock of a guy.

One day, his mom said, 'I will have a friend come over tonight.'

'Will he stay the night?'

'I think so.'

'Well, who's this guy?'

'An office colleagues

'Is this your first date?'

'We went out for lunch twice. Today, I invited him over for dinner.'

'Ahh! I see. But, why are you not seeing that other friend who came over the last time?'

Julie looked up and said, 'Max, listen. I want us to be close. But, understand one thing, you will never ever ask or give advice about the people I am seeing in my life unless I ask you. What I do, who I do with is entirely my decision. As I would never ask you about the person you go out with. Are we clear?'

Max was actually relieved somehow. He said, 'I am sorry. I understand.'

'Thanks, sweetheart! There are just some things we should do on our own.'

Max knew what that meant. He went about with his day in his room when he heard a knock. It was his mom standing.

'Is this okay?' her mom said

Max looked at her. She was wearing a red, deep-cut bra that accentuated her cleavage and a matching lacy panty. Max just said, 'Wear some lipstick.'

She wore some lipstick and she looked gorgeous. 'Now, what should I wear over this?'

Max bought a sheer overcoat which did little to conceal it. Her mom kissed him on the cheeks and said, 'Do you think I am sexy?'

Max hugged her and said, 'Hotter than anyone.'

'Okay. Thanks, baby.'

As usual, Max went to his room early. He waited impatiently. He could hear the guy and his mom's voices. They were probably drinking. As soon as Max heard the sound of his mom's door shutting, he peeped. The room was lit as usual and he could see his mom sitting on the lap of her friend. He couldn't see much since the keyhole was obstructing. He could make out his mom was moving on the guy but he couldn't see much. It was so frustrating. He could just see the legs or hands of his mom or the guy move. Still, he slid inside his pants and jerked off earnestly. He came back to his room and tried thinking of a better plan. He had to see everything. He again went outside his mom's bedroom. The lights were dim but he could see some movements. What was her mom doing?

As he lay on his bed thinking, he slept off.

Over one of the dinners, he asked, 'Mom, do you have a boyfriend?'

His mom chuckled and said, 'No.'

'Would you ever marry one of your friends you meet?'

'I don't think so.'

'Why?'

'Well, to be completely honest, I have never thought about remarrying ever since your dad divorced me. And I have you. Marrying someone else means having another family. Taking care of them etc etc. I like where I am right now. I have some fun, yes. And I have you to take care of. And you take care of me. I don't see any reason why I should give up this. Do you think otherwise?'

'I like taking care of you. But do you love any of your friends?'

'No. I don't think I love them. Otherwise, they would come over more often.'

'Do you want them to?'

'No, I have you to love. You're almost a man yourself. And you are handsome. Why don't you have a girlfriend? Or do you but you haven't told me about her?'

Max's face flushed. 'No mom. I don't think I have clicked with someone yet.'

'Haww!' exclaimed Julie with mock anger. 'You didn't click with me too?'

'You are different, mom. You are the only one I click with.'

'Have you ever been on a date?'

'Not really.'

'Okay. I think we need to get you on a date.'

'How?'

'Umm..me and you. What do you think?'

'I would love to.'

'Okay, next weekend then.'

'No, if we do this, we do it right. My birthday is coming up. Let's go somewhere for the weekend. And we can pretend to be a couple.'

Julie laughed, 'That sounds nice. Yes, let's go on a vacation together.'

Max was so excited that night. He couldn't wait for his birthday. As he started imagining what would he wear, what would his mom wear and if they would dance, Max slipped his hands in his pants and he came so intensely in minutes.

Why was he disappointed, he couldn't figure it out? Did he like seeing her mom's body getting ravished? Did he want to see her taken up mercilessly? But he was relieved too that his mom still loved him and only him.

One evening, his mom was late coming from the office. Worried, he called her.

Over the din, he heard her speak out loud over the phone, 'Sweetie, I will be late. I have come to an office party. There's food in the fridge. You eat and go to sleep. I am sorry I didn't tell you earlier.'

Max had his dinner but he couldn't go to sleep. He sprawled out in the living room watching TV. At around 11pm, he heard his mom come home. His mom was drunk and she was accompanied by a man, much older than his mom. His mom came up and hugged him, 'Oh! Why are you still awake?'

Max whispered, 'Will he stay?'

His mom whispered, 'Yes. He will be here tonight. He's a friend of my office colleague. You go to sleep.'

'You sure you will be okay, mom?'

'I am sure you will keep a watch.'

'I will.'

Max went to his room. Excited, he kept pacing the room. His mom went to her room accompanied by the guy. As soon as she closed the door, Max went out to peer through the keyhole. The guy scooped her mom up and started kissing her. Within minutes, her clothes were off. She was just in her lingerie. The guy took her by her neck and made her sit. He whipped out his hard dick and bought it in front of her mouth. Max saw the hunger in her eyes. She eagerly lapped it all in sucking it hard. But the guy wasn't happy. He took her hair and started pushing himself inside her mouth. She tried resisting but he wouldn't let go. He kept thrusting. Max had already cum once by then. But, he stood on. After some time, he threw her on the bed. He bit her boobs and fondled her boobs that she screamed in pain. He choked her throat as he bit her nipples and pinched it up with his teeth.

Fuck!

Even before, she could adjust, he had spread her legs and slid himself in. He wasn't slow at all. He pushed and thrust. He didn't let go of her boobs instead he got wilder on them. He didn't let go of her legs. He had spread them apart and was pumping hard. His mom only looked at him and moaned and groaned. Max was so hard and so mad that he came two more times. Yet, he couldn't stop watching.

At some point, the guy slowed as his eyes rolled. He had come inside her. His mom finally pushed him off. The guy kissed his mom on the lips and said something. His mother smiled and nodded her head.

He was so exhausted and yet so horny. He had dozed off and he woke up suddenly. It was 2 am. He ran to his mother's room. It was dark but could he hear sounds. Yes, he could. His mom was moaning slightly. Fuck, was she still going on? Max imagined his mom getting fucked, riding the guy, being fondled and eaten out. He came again. He was totally spent. He laid on his side and slept off.

He woke up to his mom kissing his cheek. With her hair tousled, she wore a white shirt and again she had her buttons undone. She had a smile on her face and said, 'Can I lie down?'

Max gave her space and as she laid beside her, he faced her. He came closer to her and said, 'Mom, you bathed already.'

'Yes. Why?'

'Nothing. I like it when you smell different. Like you smelled the last time.'

Max went and undid the buttons on her shirt. 'Did he hurt you?'

'See it for yourself.'

As Max undid each button, her boobs pushed out. He removed the shirt and gazed at them. They looked so tempting and there was only one red spot near the nipple. As he lowered his head to kiss it, his mom tousled his hair. He pressed closer as he put his leg on her and drew her closer. He knew he was just in his shorts as his mom was in panties. He pressed his hard dick towards his mom as he kissed the boobs slightly. He traced the curve of his mother's body. As he reached her belly, her mother put off his hand but didn't stop him from suckling. He loved how the nipples felt - rubbery, soft. He remembered how violently they got kissed yesterday night. He tried to bite the boobs but the more forceful he got, the harder he got. And he came in his pants again.

'Mom, don't bathe the next time.'

'Well, he went this morning and I had to take a bath if you know why.'

'I like it when you smell of sex.'

'Oh, baby. Ok. Can I ask you something though? Will it be better for you if you stay somewhere else when my friends come over?'

'Why do you ask that?'

'I don't know.'

'To be honest, I find it hot. But you have to promise not to fall in love with them.'

'I have told you, baby. You're the only man I love.'

She continued, 'We have to get you a girlfriend.'

Max sighed, 'Only after I had my first date with you.'

One night, Julie said, 'Do you want to cuddle and sleep with me? I am feeling rather down today.'

Max shrugged, 'Yes.'

As they laid, Max cupped her boobs. Julie exclaimed, 'What's wrong?'

'What do you mean?'

'I am not feeling that familiar pinch. as she pointed out to his shorts.

Max chuckled, 'It's embarrassing. I don't want to talk about it.'

Julie turned around and said, 'Tell me. I tell you everything. Come on, no secrets.'

'Fine. It's stupid. I don't know why but I am more aroused when I know you've been with someone.'

Julie said, 'What?'

'Ahh! I don't know why. But, the two three times you did get your friend to stay the night. I heard outside the door. And then, when you come to me, I wanted you so fiercely.'

'Ahh. Don't be embarrassed. You are saying you find me more attractive when you know I have been with someone the other night.'

'It's not another night. Like, the last time when you came home from the party with the guy. I was so horny for the next 3-4 days. Because every time I saw you, I imagined how the guy had you and it made me want you more for some reason.'

'Wow. That's exciting and definitely not stupid.'

'Ahh! So, if I was giving a stranger a blowjob and he came into my mouth and I swallowed it. If I kissed you right after that, would that make you horny?'

Julie laughed and said, 'Don't answer that. I can feel the pinch on my panty.'

'See, you're embarrassing me.' Max grumbled.

Julie hugged him tighter and said, 'As I said, I can never embarrass you.'

But something changed. Julie started called her suitors' home more frequently. And Julie started doing all kinds of new things. As Max would watch her through the door, she would stop and come over to his room in the middle of sex, 'Baby, are you asleep yet?'

Max would watch helplessly as he saw her nipples glistening with the saliva of the guy, half-red from the sucking. Julia would make him kiss her boob goodbye and Max would end up jerking to it instantly. Julie would let her suck as long as he came.

The other time, Julie came to kiss him because she had just swallowed the guy's cum. As Max came hard, Julie would leave.

But every time, the next morning, Julie would wake him up and lay by his side. Neither would say anything as Max would just trace her body. He sucked her like a baby as his hand traced her pussy over the panty and grabbed her ass. He would always end up coming in his shorts.

dorry123
dorry123
83 Followers
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