Dear Diary: Today I Caught My Son Spanking His Monkey
Copyright© 2020 by Eddie Davidson
Chapter 5
Coming of Age Sex Story: Chapter 5 - Short story about a mother who catches her son masturbating to MILF porn and subsequently peeping on his older sister while she enjoys a little time sitting on their wobbly washing machine. Read Mom's secret diary as she catalogs every detail as she remembers it.
Caution: This Coming of Age Sex Story contains strong sexual content, including Fa/ft Teenagers Blackmail Incest Mother Brother Daughter FemaleDom Humiliation Light Bond Spanking Revenge
Dear Diary
Thursday, August 11th, 2020
That morning I set up my camera phone and sucked Pat’s dick like it was the sweetest banana I had ever tasted. He came quickly, and I smiled at him.
Pat’s eyes were full of stars after he orgasmed. He wasn’t used to a surprise blowjob in the morning, and he lay back on the bed and sighed with relief. It seemed my husband was willing to forget about my antics last night as long as I kept him satisfied.
I put on my sheerest dress and lowest cropped top to expose my ample cleavage and walked upstairs to show my son the cum in my mouth. He made me blow bubbles for him before he’d let me swallow and smacked my ass.
“Good girl, you are doing well. I think in a few weeks we’ll revisit the rules,” he said. He didn’t make it clear whether he meant to make them stricter or release me from most of them, as he had mentioned earlier.
“This is not worth it, Sir!” I said when I reported to him after he came from school. “I was trying to avoid damaging my credibility and reputation by obeying you,” I folded my arms stubbornly. “What is the point if you are going to make me do all these humiliating things?” he said.
“The point is you’ve already masturbated in front of the family and got away with it. If you stop now, then they will still remember you did that, but they will also know about all your wicked fantasies about THEM!” he said as he pulled his dick out of his shorts.
“Give me a handjob,” he said as if challenging my will to disobey him.
“I am your Mom,” I reminded him.
“You are Barbara now. You were demoted, remember? You had no problem spanking my balls until I jizzed all over the table. You have a problem with spanking my monkey to make me jizz?” he said.
I began to stroke his dick. It was strange to hold his cock in my hands. I could have squeezed and crushed his balls. I didn’t, though. I stroked him until he came in my hair.
He made me lay back on the bed in the nude and let him spank my snatch until it turned red and puffy.
“Leave the cum in your hair, and if Pat notices, I want you to tell him that he did that this morning,” he said.
“Yes, Sir,” I replied. My son had defeated me, and I was bound to play his games. If I refused at this point, he would expose my dirty little secrets. It would not change what happened the night before. Michael assured me it was a lesson he didn’t want to repeat.
“I want you to punish Courtney. You have three days to do it. I don’t care if it’s tonight or Sunday, but if you don’t, I’ll come up with another elaborate but contrived scenario, and you will be the subject of my amusement. You are a nosy bitch. Do what you do best and go dig up some dirt on my big sister. I will let you spank her, and you can feed your nasty impulses,” he said.
He was right. I still enjoyed spanking butts. I just didn’t want to get mine spanked.
I went about my normal routine for the rest of the evening. Courtney kept her nose clean and was incredibly helpful. She didn’t say a word about my spanking the night before. I knew I had to find a reason to punish her within three days, or I would go through that same spectacle again, and I did NOT want that.
I have to admit that it felt like I was on a runaway rollercoaster to be the subject of attention and exposed last night. I had so many butterflies in my stomach while it was happening. It was definitely something I did not want to repeat.
Friday, August 12th, 2020
I sucked Pat’s cock again, and all was well with the world with him. The morning blowjob ritual seemed to please him enough. He overlooked all the other strange things I was doing around the house and the slutty clothes I was wearing.
That morning when I visited my son in his room to let him inspect my clothes and give me permission to swallow, he told me he had a present for me. He made me listen while I blew bubbles with his father’s cum for him.
“Courtney skipped school this week, and she had in-school suspension for it, but she didn’t tell you about it,” he said.
It wasn’t like Courtney to skip school. She was busy in a lot of extracurricular activities and loved school. I wondered what she had done. I was angry with her, but it hardly seemed like something worth spanking her in the most humiliating fashion possible over.
“Tonight, when she gets home, you will make a point of going through our backpacks. You will find the form for suspension, and you will find her dildos. I think she started playing with herself at school so you wouldn’t catch her at home,” Michael suspected.
I wasn’t sure how he knew this, but he had surprised me so far, and I didn’t question it. I promised him I would put her through the wringer tonight in front of him and his father. It would be fun for me to be in control again.
“There is one more thing, though,” he added. I came to realize there was always a catch or one more thing with Michael. “The Hannigans will be visiting for dinner,” he said.
The Hannigans are our next-door neighbors. Their son Ricky was Michael’s age, and he has always had the hots for Courtney.
“They aren’t going to sit by while I spank Courtney in the living room, Sir,” I said nicely.
“This was your fantasy,” Michael chuckled. I had written about it in my diary. I reminded him that it was just a fantasy and that I didn’t really intend to act upon it.
“Well, now, your fantasies are becoming a reality. I am sure the Hannigan’s would love to read your diary sometime,” He implied that would be a consequence of my refusal at this point.
“I will scold her and try to punish her when they visit, Sir, but I can’t guarantee they will sit through the entire thing!” I said.
“That would be a shame if they walked out in the middle of the show,” Michael shook his head as if he felt pity for me. “I’ve delivered Courtney’s ass to you on a silver platter. You didn’t have to do any sleuthing or sneaking around on your own, and you are wasting a golden opportunity to humiliate her in front of little Ricky Hannigan,” he said.
“I just don’t think it would seem very plausible to them that I couldn’t wait until after they left to address this with Courtney, Sir,” I said respectfully. Michael would find ways to punish me if I didn’t watch my tone with him.
“You could be right,” Michael smiled wickedly and told me that I had all day to think of how I was going to sell them on the idea that if you wait to punish her later, it won’t have the same impact as if you do it while what she did is fresh in her mind. “You also have all day to think about what happens if you chicken out. They won’t be the only ones who see your photos and diary. You can either humiliate your daughter or yourself,” he said.
I told him that I wouldn’t chicken out but reminded him that I can’t guarantee their reaction.
“You need to convince them that it is helping Courtney realize that her behavior is unacceptable and that she should have thought about the possibility before of what would happen when she was caught. You made that case with me many times,” he reminded me I had used those exact words when I punished him before.
“if you can’t convince them I am sure you will have an easier time convincing them that you don’t want tan lines and that is why you have started sunbathing nude in the backyard on the weekend,” Michael warned me that would be part of my punishment if I failed him.
He also pointed out this big window in my room that faced their house. Pat bought me one of those Peloton bikes last Christmas. It has been collecting dust since then.
Michael told me I would be rolling up the curtain and doing morning workouts on the machine in the nude. “If you won’t show them Courtney’s ass, you will be showing them yours. One way or the other Ricky is going to get a show,” he said.
I stopped Michael before he added any more stipulations and told him I was on board with his plan.
I spent all day at work, playing out scenarios in my head. Michael made me masturbate at my work desk through one of the Zoom meetings discreetly and let him watch through my Camera phone. It was a gentle reminder that if I disobeyed him, he would think up increasingly humiliating punishments for me.
I felt terrible that I would have to humiliate Courtney to save my own ass. My consolation was that she really should not have been skipping school. If it was true she was masturbating at school, it explained why I couldn’t catch her doing anything wrong at home.
That evening when I came home, I was fired up to punish my daughter when the time was right. Michael wanted me to make my world-famous Lasagna. I just heat up frozen Bertolli Lasagna and pretend I make it from scratch. That is probably one of my most benign dirty little secrets.
The Hannigans were already at the house when I got home from work. I greeted Allison and Bob. I informed them that dinner would be ready soon. Allison was about my age and had red hair. She looks a little like Miranda from Sex in the city. I offered them some wine and told them to make themselves comfortable. Allison looked at the skimpy outfit I had on with a little scorn on her face but said nothing. I knew she was secretly judging me.
Rick tried to pretend he didn’t notice my tits were nearly popping out of my dress, and I didn’t have on a bra. My nipples were protruding through my top, and there was nothing I could do to hide it. I was excited and turned on by this scenario despite my trepidation about their reaction.
I was still waiting on Pat to come home from work and Courtney to finish cheerleading practice.
Ricky was playing video games with Michael. Ricky is nerdy and shy. He is also incredibly polite. He couldn’t get over how I looked in my skimpy outfit.
“Mom, make us a sandwich,” Ricky snickered when I checked on him.
I obediently took their order for what they wanted on their sandwich and went and made them a snack while I popped dinner in the oven. I heard Ricky tell Michael he was shocked that I let him talk to me that way. Michael assured Ricky that he’d probably be very shocked this evening.
Pat came home next and wasn’t surprised that we had the neighbors over for dinner. He is pretty laid back about things like that. He didn’t ask me why I invited them. I am glad because it wasn’t me that invited them. Michael had made the arrangements and probably told them that I invited them over for dinner.
I made small talk with the Hannigans while Bob undressed me with his eyes, and Allison tried to hide her look of disdain over what I was wearing. They talked about mundane things like politics, weather, and sports. It was refreshingly normal.
I decided to foreshadow a little about what we had planned for them this evening. “I’ve recently had a lot of problems with Courtney and Michael. They are both entering puberty and dealing with uncontrolled hormones. It has been a real handful dealing with them. How are things with Ricky?” I asked.
“Our son is well behaved, and we don’t have any problems,” Allison stuck up her nose when she said it in the most judgmental way. “I suppose we might have problems if we were poor role models,” she implied, my outfit was completely inappropriate. I have to admit that I agreed with her on that subject.
I was wearing a sheer grey outfit that hugged my hips, exposed my cleavage, and made me feel exposed and vulnerable. I was also wearing impossibly high heels and a lot of makeup, just like Michael likes.
“I’ve been doing my best, but I’ve had to revert to old fashioned measures like good old fashioned spankings sometimes,” I said.
That shocked the two of them. They clearly didn’t feel the need to spank Ricky.
“It worked on me when I was that age,” I said.
“Yes, and you turned out fine,” Allison’s sarcasm was not very subtle.
Courtney came home shortly after that from cheerleading practice. I was actually thankful that I was no longer stuck in that catty conversation with my neighbor. She was still wearing her cheerleading outfit and had her backup slung over her shoulder.
I made a bee-line for the door and told her that I wanted to check her backpack.
“Why?” she snorted derisively. I informed it that I couldn’t trust her or Michael and that I would be performing random checks.
“You checked Michael’s bag when he got home?” Courtney pouted her question. She had already noticed I had a double standard for Michael and let him get away with a lot around the house. It was pretty obvious. I told her not to worry about Michael and that I said it was a random check. “That means one day I may check his bag, but today I am checking YOUR bag. If you have nothing to hide, you won’t mind?” I said.
Courtney looked nervous. I was starting to get wet just thinking about spanking her.
I didn’t have to spend time leafing through her papers to find the in-school suspension form. I asked her about it, and she said she just needed a day to herself and that it was not a big deal.
“Why didn’t you tell me about it?” I demanded.
“I was going to tell you tonight.” She pouted.
“This happened on Tuesday, and you are just now telling me about it?” I didn’t raise my voice, but my intensity increased as I reverted back to my more forceful persona. Michael has been making me act submissively, and it’s been challenging to get back into bitch-mode when I need to do that.
“Yeah, well, you kind of made things all about you last night, and I couldn’t!” she said. She had a fair point, and I didn’t want her telling the Hannigans that I asked to be spanked in the living room. I dug deeper into her bag, and Courtney looked just as shocked as I did when I pulled out her dildos.
They were actually MY dildos. My All American Whopper was in my purse, but I had several other sex toys that I liked to play with. Michael had likely planted them in her backpack.
“Those aren’t mine!” she pleaded with me to believe her. I did believe her. She had freely admitted she skipped school. She was not willing to accept guilt for taking my dildos. She looked disgusted by them and scrunched her nose in disgust.
She may have stolen my sex toys and taken them to school. It would have explained why I couldn’t catch her masturbating at home if she was getting her jollies elsewhere. It dawned on me that Michael could have planted them on his sister. It would explain why he KNEW they would be in the backpack. I didn’t have time to decide if Courtney stole my dildos and brought them to school. I went with the premise she did and held them up to her face so she would be intimidated.
The Hannigan’s were quiet as they watched the spectacle at our front door unfold. They looked serious and concerned about the confrontation I was having with my daughter. I didn’t blame them. I was pretty convincing when I put my finger in Courtney’s face and challenged her innocence in all of this.
I told her Courtney she was a liar. “This is what I meant when I said that their hormones are out of control. We’ve recently had a problem with Courtney being unable to stop touching herself,” I explained to the Hannigans. I left out the part about Michael getting caught doing it too.
Allison looked shocked, but Ricky and his dad were smirking. My daughter is cute and has curly blonde hair. I think any straight guy might have had a hard time not being amused, thinking about her masturbating uncontrollably.
“Mom, no!” Courtney folded her arms in front of her chest and stubbornly insisted I stop right now. She knew exactly what I was going to do. I had promised her I would punish her if I caught her doing anything naughty even if other people were at the house.
“I am sorry, but you knew what would happen if I caught you doing something wrong. Don’t think just because the Hannigans are here that I am going to let you out of it!” I said.
“Go get my paddle from my room and assume the position in the living room,” I instructed Courtney. She huffed and walked to my room to get my paddle. Michael returned it to me so that I could use it tonight.
“Maybe we should go and come back another time,” Allison suggested. I didn’t blame her. This seemed like a family matter, and things were about to get weird. They shifted uncomfortably on the couch. Ricky and Michael stopped playing video games to watch, as well.
“It won’t take long, and It would do Courtney some good to see that I won’t change my plans just because she chooses to misbehave. I’d appreciate it if you would stay,” I said.
“You are really going to spank her in the living room?” Allison asked rhetorically. I affirmed that was precisely what I would do, followed by time in the corner to think about what she did.
“Not on her bare bottom, though, right?” Allison sounded like she was pleading for some clemency.
“She usually does,” Michael offered a quip and interrupted our neighbor’s scornful rebuke of my parenting methods.
“I normally do, but since the neighbors are here, I can just have her lift her skirt?” I asked my son if that would be okay in a very subtle way. I made it sound to the others like I had already made up my mind. It was really up to Michael how far he thought I should try to push things.
“Sure, if you want to be inconsistent and send mixed messages,” Michael chuckled.
Courtney walked out of my bedroom, holding my paddle and approached me reluctantly. She hadn’t heard our conversation while she was in my room. “Assume the position in the living room,” I pointed to the spot in the center of the living room where I spanked her before. Courtney faced her father’s chair and bent over and grabbed her ankles. She was incredibly limber. Her ass didn’t face the couch, and I was thankful for that.
“Please don’t, Mom!” she begged. “Not in front of the neighbors,” she said.
“I apologize to you,” I said to Allison directly. I knew she was the only one of my neighbors who was genuinely offended. Ricky was beside himself with joy and trying not to draw his mother ire by appearing too enthusiastic. Bob did what Pat did when I spanked Courtney. He shifted uncomfortably and pretended not to want to watch, but he was definitely watching. “My daughter has forced my hand by skipping school. I am sure she was playing with herself at school because she knows she can’t get away with it at home. She can’t seem to keep her hands off herself,” I said as I lifted the back of her mini-skirt.
I thought she would be wearing spanks. Cheerleaders do a lot of flips and handstands, and they typically wear what is essentially matching tight little shorts under their skirt, so you do not see their panties. It is a practical solution. I am sure guys still like to watch the pretty young things flip and twirl, but they can’t see the girl’s dainty little panties and camel toes when that happens.
Imagine my surprise to discover that my otherwise perfect little daughter wasn’t wearing panties OR spanks. I lifted her skirt to reveal her entirely bare bottom! I was just as shocked as everyone else, and the look on my face was genuinely embarrassment.
I no longer suspected Michael planted my sex toys in her backpack. My daughter must REALLY be a tramp after all if she goes to school in her cheerleader uniform and doesn’t wear anything underneath.
“Where are your bottoms?” I demanded. I could see my daughter’s juicy little pussy start to drip and glisten as she shivered when I asked her the question.
“They are in my backpack, Mom!” Courtney stuck her cute little upturned nose in the air like a spoiled princess. I don’t know if she intended to sound like a bitch, but her tone suggested she was angry that I was making her explain herself.
“Why?” I asked her as I stood behind her ass. Ricky angled himself subtly so he could get a better rear view of my daughter. I was happy she’d be humiliated now. I no longer felt guilty for punishing her at all. Michael may have engineered this scenario, but I felt vindicated that I was punishing her bare ass now.