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The Lesson

The Lesson

by Dentalflosstycoon
20 min read
3.68 (48400 views)
mothersoncucold
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If you don't like cuckold themes you will definitely hate this. You can still read it and leave a nasty review, because I love those most of all, especially the reviews that are longer than my story. Yes, I promise I will read the whole thing. I planned for this to be a quick story in between others but it ran on and became 15000 words, sorry. Oops, just added 2500 words, sorry. Probably should have been two stories. I like it more than anyone else probably will.

I hope you like it anyway.

All people engaging in sex are over 18 years old.

My name is CJ, for Charles Junior. My father was killed in a car accident when I was young. From his pictures I can tell you that I look just like him. He was short, thin and looked a bit like a nerd. He had a great job and was smart enough to have provided for us even upon his death. The life insurance paid us 2.5 million and paid off the house which meant my mother wouldn't need to work. My 20 year old sister, Kate, was already working as a CNA and lived in a studio apartment in Buffalo, 20 minutes away.

My mother, Alice, seems to be a mismatch to my father. She is what I would call gorgeous. That's right, my mom is a sexy, beautiful, voluptuous, blonde woman now aged 39. She's 5' 5" tall with perfect c-cup breasts with no sag yet. Her legs are oh so pale, smooth and seem to draw everyone's eyes to them. I'm not sure how my father landed her but every male I know wants to fuck her. She has her dates and I have heard her having loud sex after a date but she usually tries not to do it at our house with me home. The two times it did happen, I masterbated listening to my mother's erotic sounds.

My friends and I are the typical nerd group of our school. We study, get good grades, play video games, watch Star Trek and Star Wars, and shy away from socializing and girls.

The last one of the four of us just turned 18 years old. Danny turning 18 meant we could all go to R-rated movies together. Chris and Kevin were both a few months older than me.

My mother, having so much free time, was our den mother so to speak. We spent most of our free time at my house where she kept us fed and comfortable. Many nights including almost every Saturday night my friends would sleep over. I'm pretty sure my mother felt like she had four sons. I also know from our conversations that my friends lust over my mother. I don't blame them, even I think she's hot. It sure doesn't help that each of us is still a virgin.

We are three weeks away from graduation and splitting up to separate universities after the summer. It will be hard for all of us. We've been inseparable for years. I know we'll remain close for the rest of our lives but it's going to be a culture shock. Not to mention not having my mom around to cook, clean, and look at.

I could tell the change was starting to worry my mother as well. She seemed nervous when talking about going away to school.

"CJ honey, are you going to be alright? Are you ready to live on your own? I think I might have spoiled you boys a bit too much."

"Mom, we'll be fine. If I screw up doing laundry I'll call you so you can help me, that's all. I'm not going to die of starvation or anything."

"What about girls?" My mother looked at me sideways shyly. I know she isn't shy so I wasn't sure where this was going.

"Yes, there will be girls there, and they will ignore me like usual."

My mother sipped her coffee on this Saturday morning. I could tell she was thinking and daydreaming, about what I had no idea. Finally after several minutes of her seeming to be miles away she said, "Will the boys be over later?"

I nodded my head, "It's Saturday, obvi."

She grinned, "We need to prep you guys. I have to call Kate. I'll be back." She uncharacteristicly went out to the back deck to speak to my sister. I didn't know why she was being secretive. When the conversation ended she came back inside. "Kate will be coming over tomorrow."

"What's going on mom? What do you mean by 'prep you guys'?" My mother was my rock and she rarely did things to upset the turnip cart, but she had a crazy look on her face that I was having trouble reading.

Later that afternoon, my friends started to show up. Chris had just spent all his money on the newest version of our favorite video game franchise. We were pumped and ready to kill people. The basement was our hangout for gaming. As we headed to the stairs my mother yelled from upstairs, "Wait!"

We stood waiting to see what she wanted. From upstairs we heard her footsteps beginning to descend the stairs. All of us backtracked down the hall to see what she wanted. When she came into view our mouths all fell open. None of us had ever seen my mother looking as sexy and hot as she looked today. She has never been the type to prance around the house in skimpy garments. Today she must have flipped a switch. Her sweet c-cup breasts were freely bouncing with no bra under an almost transparent white button down collared shirt with THREE buttons unbottoned. Below that was a leather mini skirt showing off the two most toned and sensual legs ever. I also got a glimpse of a pair of red panties as she slowly came to our level.

"Are you g-going out mom? You look.... nice."

"No baby, I need to talk to the four of you. Please sit in the living room." We were captivated with her beauty and raw sexual presence. Stunned, we just stumbled in like zombies, COD was officially on the back burner.

"None of you needs to respond as I lay out a plan that is mapped out in my head. Please let me explain it all before you try to understand, disagree with, or negotiate. Understood?" Everyone nodded.

She inhaled deeply. "You four boys are my kids. Yes, CJ is my son but Chris, Danny, and Kevin, I love you as much as CJ. You have spent as much time with me as CJ. I care about all of you deeply and I worry about you equally."

"I see the day fast approaching when you will fly the coop and spread your wings. But none of you is ready. I love you all but growing up as nerds gives you certain strengths and weaknesses."

"You have brains and a work ethic that will serve you well financially. Each of you, no doubt, will be making six figures right out of college. You also have each other. This group is probably the strongest bonded friends in your school. Many others think they have good friends only to find out it was superficial."

"Now the weaknesses. You all have limited social skills. You're great with each other but have no interest or ability to meet new people. This is a problem. You have almost zero experience with girls or women. This is a bigger problem. And finally, you have low self esteem and self confidence. This is the biggest issue. The previous two are just symptoms of this much bigger weakness."

"Like I said earlier, I love the four of you deeply. I want you to succeed in LIFE. I have no doubt that you will succeed professionally. Therefore, I have a plan that will help you become happy adults. The reason I want to do this is that you don't understand the pitfalls coming your way. I don't want you to have to endure hardship and misery if I can help you avoid it." She paused and looked around. They were all staring at her legs. "Fuck, did any of you hear what I said?"

"Yes Mom, we all heard you. We have to look somewhere."

"Do you have any questions so far?"

"Mom, yes, why did you dress up for us?"

My mother smirked, "I needed your attention and I knew the new COD came out yesterday. It's very difficult to compete with a new game. I figured I needed a little advantage."

Chris spoke up next. "So I take it you're aware that we all have a crush on you."

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"Chris, honey, of course, it's natural. I know I have a great body and you are horny teenagers. I actually plan on using that to my advantage for my plan."

Kevin raised his hand for a question. Alice answered, "Kevin, grow some fucking balls and just blurt out your question."

"Okay, sorry."

"No, not fucking sorry either, just try and be a little more of an asshole. You're way too fucking nice." My mother looked stern.

"Oh, okay, sorr... I mean FUCK!! How's that?" He smiled.

"Better!!" my mother exclaimed laughing hard.

Kevin dropped the smile and asked his question. "What does the plan encompass?"

"Well, we have a little more than 3 months until you take off for school. My plan is to coach you socially, give you confidence, and teach you some key facts about women and marriage."

"What's the first step Mom?"

"Tomorrow Kate will be taking you shopping for new clothes. You boys dress too conservatively. We need you looking great so you are more confident."

"After that you begin training physically, as in exercise. Being pudgy is part of the low self esteem. The four of you will be doing cardio and weight training. I will be feeding you nutritional food and there will be no unhealthy snacks. You need to be fit to have confidence."

"Kate and I will also be teaching you how to cook. Once a week we will cook dinner and drink wine."

"I know that you boys can't dance, so you are taking some lessons. Nothing makes a woman happier than going dancing."

"Once a week you will have class with me learning about women. The more you understand, the more confident you will be. And trust me, women WILL be after you soon."

"Finally, you will go to parties. This is the hard one. It all comes together here. First, you four will go together for mutual support. Then you will go in twos. Finally you will go alone and practice meeting new people."

We looked at each other skeptically. Alone at a party is my biggest nightmare. I don't see it happening. Hell, going to a party with all four of us is a stretch.

My mother sighed, "I realize some of this seems insurmountable but I believe in you. You boys are capable of doing all of this. You'll see, going to a party alone is the 'Big Boss' as you would call it. The last in a string of accomplishments that will leave you happy, confident, and ready for life. Okay?"

"Sure Mrs. Johnson," Danny said, "We'll try."

"No!! This is critical to your future happiness. Do or do not, there is no try." We all laughed at her Star Wars analogy plus she got it right. Normal people don't get that quote right but my Mom got it!

She smiled. "No more Mrs. Johnson either. All of you including CJ will call me Alice from now on. And video games will be limited to one night a week only. You will not spend the summer sitting in your dungeon."

We moaned about the last part. We had spent (wasted) every summer playing video games in my basement. This would be a tough transition. I questioned my mother's ability to keep us from our Xbox.

We played COD all night and woke up around 11 to my sister stomping in and yelling for us. We made it to the kitchen and grabbed a quick breakfast. Meanwhile Mom, I mean Alice, was telling Kate to get us each a set of clothes to wear to a party. She said next week she could take us out again to get casual wear for day to day.

We actually had a lot of fun spending the day with my sister. She is really cool and has great fashion sense. My friends all have a crush on my pretty sister but Chris has a world class infatuation with her. She is the girl of his dreams but he's too shy to do anything about it. We all got an outfit to wear to a party and made it home in time for dinner.

Alice was once again dressed provocatively as she served us dinner. I didn't understand why but I guess this is her rodeo. We all showed off our new threads for Alice after dinner. She whistled and clapped and oohed and ahhed at us. "Tomorrow you all have an appointment at the hairdresser after school. While you were out, I got the four of you a gym membership for your weight training. That will be Tuesdays and Fridays while Thursdays we will be at the school track running. Wednesday is my class here. I also got you signed up for dance lessons on Monday evenings.

Friday or Saturday will be party night. Sundays will be a relaxing day of cooking and sampling wine. Are you guys ready?" We growned about the exercise part of it. But in my head I knew it was probably a good thing.

The hairdresser didn't even ask how we wanted our hair styled. Kate had already left instructions. We walked out of the salon with our new looks feeling even better about ourselves.

Monday evening was dance class. It felt like exercise with coordination training. I began to realize that this was hard. I felt like a complete dork. I hoped I would get better. The other guys all seemed to do ok, but afterwards they said the same thing. We needed help.

Tuesday we went to the gym where Alice had arranged for an instructor to explain how to use the equipment and how to sculpt our muscles. We came home a little sore but I for one felt good about the experience.

Wednesday was Alice's first lesson night. She looked a little nervous at first and again was dressed slutty.

"Today boys, we talk about women, unless any of you are closet gay. I know by the way each of you looks at me that none of you is gay. So women. This is the most critical piece of your happiness from now until you die. Women can bring you years and years of joy, or they can destroy you utterly. They can crush your heart, take all you worked for away, take your children away, humiliate you and make you want to off yourself. It sounds terrible because it can be. As I told you before, I love each of you like a son. I don't want this to happen to you. Unfortunately as of last week you were especially vulnerable to falling victim to the kind of woman that can destroy you. Ok, first question. Who can tell me why you boys are not popular with girls?"

Kevin loudly spoke, "Because they're all bitches!!"

"Nice job with your forcefulness Kevin, but incorrect. Some are bitches but mostly high school girls need acceptance and status. Being seen with unpopular people makes them unpopular. Next year things change drastically. Girls turn into women and have different needs. The social paradigms change. Now they start looking for a man who can provide a high standard of living. They are trying to get a Mrs. degree. All those jocks are now working at McDonald's and living at home. You, boys, are now prime targets. That's right, the drought is over, but the danger is real. These women can be manipulative, secretive and very convincing actresses. They need your money and they will put on an act and fuck you silly to get what they want. Then one day you come home to her fucking your neighbor and you divorce her. She gets custody of the kids and more than half your money for being a skank and breaking your heart. We are going to avoid this at all costs."

"Even if you find a great woman, you still have to keep her happy or the same things can happen. So we are going to review how to stay away from skanks, how to find a good woman and how to keep a good woman happy."

πŸ”“

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"So today we will cover staying away from skanks. Next week we will review. Reminiscent of Zombieland, I am going to give you some rules.

Rule #1

Remember what your focus is. Grades!! You guys are spending beaucoup bucks on an education that will bring you big money, status, and hopefully a happy work life. Don't let anything interfere with that.

Rule #2

Enjoy the sex and fun you have. Many people go to college just for the life experience. Refer to rule #1 but smell the roses.

Rule #3

All sex must be safe!! No exceptions. Nobody wants to get pregnant unless they have an agenda and nobody wants STDs. Don't trust that they are on the pill, use your own condoms.

Rule #4

Make no commitments for at least 2 years. A steady girlfriend is fine but NO proposals. There are women who will push you hard. That's a red flag. I want to meet any girlfriend you want to marry. I want you to hear my input. I have skankdar. You don't have to listen to me, but I suggest you do. I suggest every one of you has a fair prenup before getting married. It can curb future problems.

Rule #5

Don't be a needy nerd. Starting today you are not nerds. You are highly sought after commodities. Change your view of yourself from losers to winners. Stand tall and be choosy."

Rule #6

Wear your seatbelt.

"There will be a quiz on this next week. Any questions?" Alice grinned.

Danny was still staring at Alice's legs, "I was wondering why you're still dressing like this. I mean I'm not complaining, I like it, don't get me wrong but what's the real reason?"

"Ok boys, here's the deal. Part of it is to keep your attention but I also want to see how you react to me dressed like a slut. You boys will see women dressed like this and wanting your attention. I want to make sure you don't just jump at the first skank that throws herself at you. Lastly there was a part of me hoping you would learn to flirt. Dressing like this makes me approachable. Danny, that was the closest any of you have come."

I said, "Mom, I think you look hot tonight."

"Very good, CJ!!"

"Oh, I was just saying that. Was that flirting?"

"Yes baby, compliments are the best form of flirting." Mom smiled at me.

"Ok, then you also have hot tits that I'd like to suck on!" I said with a wry smile.

Alice laughed out loud. "I bet you say that to all the girls. If there are no more questions we will be back here next Wednesday for the next class. Tomorrow we meet up here to change and go back to the high school for some running."

Running is not our forte by any means. Alice let us go at our own pace however. We could walk as much as necessary but had to try to run as much as possible. It hurt my lungs, gums, head, legs, almost everything.

At the end of the workout, Alice informed us we were going to a party on Saturday. She apparently has a connection. When we got home Kate was there and wanted us to get dressed in our party clothes. She brought us to my bedroom and showed us how to properly apply cologne.

The next step was role playing impromptu conversations. She had us list five topics we could easily talk to people about that weren't nerdy. On top of that was subtle compliments and subtle flirting.

Kate finished her coaching and said, "Chris, come over here and try out some subtle compliments with me."

Chris turned deep red but went over anyway. "You are the prettiest, nicest, coolest person I've ever met."

Kate smiled and said, "That's a good start, Chris. Definitely not very subtle though."

Chris turned red again. "Sorry, I just said what I was thinking." This time it was Kate that turned red. After all the practice, we ended the night feeling like we could actually pull this off.

Friday was our free day so we played video games since Saturday was going to be party day. Mom brought us a cruditΓ©s platter with balsamic vinaigrette for a snack. The guys actually liked it.

Saturday afternoon we began cramming for our party. Alice and Kate stood in separate rooms while the boys went back and forth joining into the conversations and trying to flirt some. Chris seemed to be excelling in the kitchen with Kate. From my vantage point in the living room she seemed to be laughing at his comments and gently slapping him on the arm. We attempted drinking but learned that staying sober is key.

With our nerves on edge we headed to the party of Jules Smith. After knocking and being let in, we tentatively moved forward. Out of the crowd heading straight for us was Jordon Beauregard, our longtime bully/nemisis. This couldn't be good at all. He closed on us quickly, put his hand out and greeted us with a smile.

"Hey guys!! Glad you could make it. Who needs a drink? There's beer, wine coolers, mixed drinks, or just soda if you want." Kevin volunteered to go grab us some beers while Jordon chatted us up like his close friends. The visual of Jordon hanging out with us must have made it acceptable for anyone to come talk to us. We spent hours drinking SLOWLY and chatting with people from school who had never acknowledged our existence before. Granted we all looked really good and our confidence was blossoming but it was almost too easy. Still we all had a great time and actually talked to some girls.

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