It was a Thursday night in late February and nothing was out of the ordinary for Charlie and his two best friends. The three young boys were playing video games in the basement of the large ranch style home. It was no secret, playing online shooter games late into the night was the preferred way to spend time together for Charlie, Benji, and Hayden or the "Three Amigos" as everyone at school called them. They would routinely lose track of time and end up hanging out together until the small hours of the morning.
This large ranch home belonged to Charlie and his family and it was the favorite destination for gaming with the three boys largely because of the lenient rules of the home and the blazing fast internet Charlie's Mom had acquired earlier that year.
The boys had always stuck close together, ever since the 6th grade that is. They all ended up going to the same middle school together and then moved to the same high school were they remained best friends. They were true friends, they didn't do anything without each other, whether it be video games, movies or activities at school, they loved to hang out. They had the same interests, none of them liked sports or going to loud parties, they were loners at heart but at least they had each other.
Benji is the real nerd of the group, if any of them would become a professional D&D DM it would be Benji. He was short and portly and didn't always have the best of hygiene but he had a heart of gold and would do anything for his friends at the drop of a hat.
Hayden is the most "normal" of the group, he was tall, strong, and handsome. The cool kids at the school were always trying to get him to hang out and play sports but for some reason he always preferred to hang with Benji and Charlie, something that his two friends were very happy about. He was considered the leader of the group by default, because of his size and looks. He didn't care about what people thought, he mostly just wanted things his way and this worked perfect with the passive nature of Benji and Charlie.
Charlie is the smart one of the group, he was always top of his class and ahead of his two friends when it came to feats of intelligence. Like Hayden, he was also attractive but didn't have the strong, tall body along with the looks. He was a true introvert, real joy for Charlie was hanging with his friends and building things in his basement.
The common thread between all of these boys was that they were inexperienced with the opposite sex. All of them were virgins, although Hayden once got a blow job in the girls locker room but that's a story for another time. They were all 18 and still scared to approach the girls at school, confidence was not their strong suit to say the least.
Charlie lives in the large house alone with his Mother. This was a recent arrangement as Charlie's sister, Claire had recently moved to New York to attend University. The sheer size of the home and the fact that only two people lived inside meant the boys could feel as though they escaped all earthly rules when playing in the basement. At least until they made noise late enough to remind Charlie's Mother to send Benji and Hayden back to their own homes.
It was past midnight on this Thursday night when the three boys heard the door to the basement slowly open and the sound of Charlie's Mom start the descent down, they all knew what would happen next.
"Hey Boys! How are you three doing tonight?" Charlie's Mom asked in her normal friendly tone of voice.
Benji and Hayden both stammered simultaneously "Good, Mrs. Dowell, How are you?"
"I'm doing just fine, thank you for asking, and you two know you can call me Sarah." Reminding Benji and Hayden that they didn't need to be some formal with her.
"Unfortunately you boys know what time it is, don't you?" Sarah asked all the while knowing Charlie and his friends knew the answer.
"We'll start packing up now, Mom" Charlie said with disappointment in his voice.
"I hate to be a buzzkill, but you boys have school in the morning and I don't think your mothers would like the idea of me allowing you to stay up all hours of the night, sorry." Sarah always felt bad sending them home.
"It's okay Mrs. Dowell... I mean... Sarah, we understand. Thanks for letting us come over." Hayden said with a smile on his face.
"I'll see you boys soon. Charlie don't stay up too late." Sarah said with a smile as she turned to head back up the stairs.
Charlie noticed Benji and Hayden check out his mother's ass as she walked out of the room, this was a common occurrence, his mother was by far the hottest Mom of the group and he was well aware his friends wanted to see her naked. Once Charlie's Mom had made it up the stairs and out of earshot, Charlie let his friends know they could come over the next night and finish up where they left off.
"Sounds good, let's plan on it! Alright Benji lets head out." Hayden said.
Hayden was again allowing his strong personality to direct his friend around. Saying a command and assuming Hayden and Charlie would listen was the way the friendship worked since the three of them could remember.
"I'll walk you guys out." Charlie said as he led his two friends up the stairs to the front door.
"See you tomorrow, dude" both of Charlie's friends yelled back at him as they headed out the door back to their respective homes.
---
It was bright and early the next morning and Charlie was woken by the welcoming smell of breakfast. This was not an unusual occurrence for Charlie to wake up this way, Sarah loved to cook, and breakfast was her favorite meal to prep for the house. Charlie hopped out of bed feeling good and rested, it was Friday after all and he had plans to hang out with his friends but first he needed to get ready for school.
Charlie threw on his favorite hoodie and jeans before he headed to the kitchen to greet his Mother.
"Hey Mom!" Charlie said with exuberance as he turned the corner to the kitchen.
"Good morning! It looks like someone is feeling bright eyed and bushy tailed this morning." Sarah said as she flipped the bacon she was cooking.
Charlie smiled, "It's the weekend, I'm excited to hang out with my friends."
"I assume you boys are planning on hanging here tonight?" Sarah asked.
"Of course we are! We love hanging out here and you know you're the coolest Mom." Charlie said laughing.
"That's right keep buttering me up, just like this toast." she said with cheeky smile, pointing the spatula at the hot breakfast awaiting Charlie.
"Alright, alright, breakfast is ready you brown nosing boy." Sarah said as she pushed the plate of eggs, bacon, toast and a freshly cut avocado to her hungry son.
"Thanks, Mom. This looks amazing." Charlie said as he picked up his fork ready to devour his breakfast.
Sarah prepped her plate with breakfast and situated herself right next to her son at the kitchen table.
"Hey, Charlie. Can I ask you a question?" Sarah said nudging her son with her shoulder.
"Of course you can." he promptly replied.
"I know you love playing video games with Benji and Hayden, but why don't you three ever go out and spend time with girls your age, huh? You know, go on dates?" Sarah asked softly.
"Mom! Why do you always do this?" Charlie said with a big sigh.
"Do what? I'm just asking." she rebutted.
"I don't have time for girls Mom! Or they don't have time for me, I don't know?" Charlie said in a frustrated tone.
"What are you talking about? Of course girls have time for you! You are just too afraid to ask, but you shouldn't be. I bet plenty of girls from school would love to go on a date with you." Charlie's Mother said as she placed her right hand on his shoulder.
"Maybe... I don't know, whatever," his voice sounded impatient.
"Can we please change the subject? I don't want to talk about this right now, I have to go to school soon." Charlie said abruptly.
"Yes, yes. I'm sorry. I just want to make sure my boy is happy that is all." his mother said with a smile as she rubbed his shoulder before releasing him.
After that short conversation the table became quiet and a little awkward. Charlie quickly finished up breakfast and headed to the bathroom to finish getting ready for school. He finished up in the bathroom and collected everything he needed for the day and headed to the door.
"Alright, Mom. I'm off to school!" Charlie yelled as he walked out the front door. Before his Mother could even reply she heard the door close behind him.
Sarah just wanted her son to have more social skills. He was 18 now and all he wanted to do was play video games with his friends. Sarah didn't have time to sit and think about this for too long she also had to get to work.
---
Sarah was a well respected lawyer of 12 years. She was known for being tough on her clients and always an extreme professional when the job called for it.
The morning for Sarah was filled with clients and planning for court early the following week. Time was flying by this Friday and it was now early afternoon and Sarah finally had a break in the day to eat her lunch. She quickly grabbed her salad from the staff kitchen and scurried back to her office in hopes of nobody seeing her so she could have some moments of peace. Just as she began to prepare her salad she heard a knock on her office door.
Sarah opened the door and realized it was a fellow lawyer named Jim Johnson.
"Hey Jim. What's going on?" Sarah asked as professionally as she could.
Jim stood at the door awkwardly for a moment before speaking. "I was just curious if you had any plans tonight?" He asked.
"Well, nothing major. Just excited to get some relaxation after this busy week." Sarah replied with a smile.
"Yeah, it has been a busy week. Any chance you would want to get some dinner with me after work before you head home for the night?" Jim was doing his best to ask Sarah out on post work date.
"Oh, Jim. That is so nice of you to ask but tonight is not a good night for me. I'm sorry." Sarah rejected his advance in the nicest way possible.
Jim smiled and took the hint. "Okay, maybe some other time then?" Jim said with a smile on his face.
"Sure, Jim. I'd like that." Sarah said in hopes he wouldn't actually ask again at a later time.
This type of situation was not uncommon for Sarah. Co-workers asking her out was something that occurred regularly. Sarah was 39 and still extremely youthful for her age. She took very good care of her body and it was nothing shy of stunning, especially in a work environment where many people around here did not take such good care of themselves.
People would often tell Sarah she looked like Sandra Bullock. She had long brunette hair, legs that just kept going with an ass that anyone with eyes could tell she spent plenty of time sculpting in the gym. However, her best feature was her breasts, she had nearly perfect tits. They were large and perky for her age, men and women alike had a hard time not sneaking glances in the office when she would wear tight blouses.
All this to say, Sarah was quite beautiful and men vying for her attention was nothing new for her. Even though men would often ask her out Sarah had still not been on date since the death of her husband 4 years ago.
Being a single mother was something Sarah never planned on having to do, her marriage was a great one but unfortunately sickness had different plans and cut her husband's life short. Not long after the death of her husband she went into a deep depression, she felt so sad and alone but her kids were there everyday helping her through it.
It took a very long time but she began to feel lighter and more like herself. She clearly understood that her kids brought her through that terrible time in her life. At that moment she vowed to be strong and caring for her children as long as she lived. She believed to the bottom of her heart that it was the least she could do for her children. Ever since that time in her life she's worked incredibly hard and built an amazing life for her family filled with opportunity and love.
Sarah's work ethic lead her to many late night's at the office taking great care of her clients, not unlike the current night for Sarah.
"Oh my God! It's already past 10!" she thought to herself. Sarah was so engrossed in her work that she didn't even notice she was the only one left in the office. She knew she had so much more work to finish before next week but she could complete much of it from home, so she decided to call it a night from the office and head back to the house.
---
Sarah finally made it home, she pulled her Audi Q8 in the garage and headed inside. It didn't take long before she heard some very muffled noise coming from the basement. The noise jarred her memory of this morning when Charlie told her that the boys would be over tonight to play video games. She didn't think much of it as she walked to her bedroom to get undressed and showered up for the night.
After she had taken off her blouse and skirt she caught a glimpse of herself in the full length mirror placed in the corner of the bedroom. She walked over and began to admire her own body in the mirror. She was playfully sticking her ass out while placing her hands tightly on her hips. "You still have it, Mom," she thought to herself before a strange noise coming from the basement broke her self-loving thoughts.
The noise was coming from the air duct on the other side of the room. Years ago Sarah would use that duct to listen in on her kids playing downstairs to make sure they were safe. Her children never found out about this built in spy equipment she used so frequently. Now that her kids were grown it had been a long time since she eavesdropped through the vent but the noise sounded like screaming and she wanted to make sure everything was okay in the basement.
She got down on her knees and placed her ear as closely to the vent as she could. It didn't take long before she knew what was happening, it was a woman moaning from sexual pleasure. Sarah could tell it wasn't an actual person in the basement, but it was coming from the TV, the three boys were watching porn! Sarah couldn't believe it, she quickly pulled her ear away from the vent and placed her hand over her mouth. "Those boys!" she thought to herself, "I can't believe they watch porn together in my house."
Her natural instinct was to get upset but she quickly calmed herself down. "They are all 18 years old, they are allowed to do this type of thing... I guess?" Sarah rationalized inside her own brain. She took a couple deep breaths and sat herself down on her bed. She was trying her best to be the "coolest mom" like her son called her earlier.
As she sat there on her bed she began to get a little curious. Sarah didn't understand what was happening but she was starting to feel a little horny at the idea of teen boys jerking off just below her in the basement. Her sudden confusing interest in the situation lead her to get back down on her knees and continue to eavesdrop on the boys "fun" night.
Once she get in position to hear the party below it became even more clear as the sound of moaning and fucking from the TV was playing quite loudly. Sarah's thoughts were running wild, "How are they doing this? Are they all sitting on the couch? Are they taking turns?" she couldn't come to terms with what was happening.
She then heard the voice of one of the boys, "Oh my God, Riley Khalifa is so hot!" exclaimed one of the boys.
"Shut up dude! I'm trying to watch here." retorted another boy.
She assumed that was Hayden considering the command. She observed over the years that he was always yelling at her son and Benji. There was no more noise from the boys over the next minute or two. She was listening so intently that she could now hear the sound of masturbation. It had been awhile since she had seen a man pleasure himself but she could certainly remember the sound. It didn't take long before she could hear one of the boys moaning, it became louder and louder until it was clear one of them had just climaxed.
All of the sudden the TV shut off. "Are you kidding me, Charlie! You came already!" yelled Hayden.
"You are such a pussy! You're just a little premature bitch!" he said with a loud laugh at the end. Benji was laughing too.
"What are you laughing at Benji? You're just as bad as fuckface right here." Hayden said forcefully at Benji.
"Whatever man! I couldn't help it, Riley is so hot." Charlie said as an attempt to defend himself.
"How many times do I have to tell you two, girls don't like premature ejaculators! You two are never going to have a girlfriend." Hayden continued the assault of his friends.
"Whatever Hayden," both Charlie and Benji said at the same time.
That was as much as Charlie's mother could take, she backed away from the vent and sat back down at the foot of her bed. She couldn't believe that Hayden was bullying her son like that. She was so upset that she had forgotten that she was just listening to her son and his friends watching porn. Sarah was no longer horny, she was just concerned about the well being of her only son.
"No wonder he doesn't have confidence!" Sarah thought. "How could he if he's being bullied by his own friend?"
Sarah paced around the room for a few minutes in anger, she finally decided to cool down by taking a shower. She considered this to be none of her business but now that she had heard that conversation her motherly instincts were not going to let it go.
---
Sarah couldn't shake the upset feeling all night, she just laid in bed fuming. She was so mad at Hayden, she could have strangled him for what it's worth. The reasons for her anger were not unfounded, she was so upset because her late husband fought against the same issue and she hated the idea of her son going through that, but with a bully to boot.
Sarah laid her head back against her pillow and thought about her late husband, Peter. It always brought her peace to do so. She remembered how loving he was, how kind and talented. He was a great Father to Claire and Charlie and she missed him so much.
Peter was not without problems here on this earth, he also lacked confidence in himself for a long time. Sarah devoted so much of her time helping him believe in himself. Just like his son, Peter suffered from premature ejaculation and it was quite the problem early in their marriage. Sarah recalled how upset Peter would get about the situation, many times he would leave Sarah unsatisfied in bed, this was causing issues in life and at work for Peter.
Sarah remembered all the nights of helping him. Sarah would research "techniques" to help men with premature ejaculation and then try them on her husband. It took many months and lots of training but slowly Peter's stamina grew. Eventually Peter could last longer than his wife in bed delivering her multiple orgasms nightly. Not only was she having better sex but the man she loved was gaining confidence that was palpable. Peter was getting raises at work, he was making more friends, but most of all he was happier. That made all of the work worth it for Sarah.
While Sarah was reminiscing on the past she came up with an idea that scared her to the core. "Should I give my son the same training?" she thought. She wanted nothing more than for Charlie's confidence to grow but could she really use sexual tactics to help him?
Sarah quickly pushed down the thought, there was no way she could approach Charlie about such a thing let alone follow through with it. She was stirring with emotion, "What if he needs this?" Sarah thought. He was being bullied and his self confidence was not good at all. The more she thought about it the more it mirrored her late husband. Her mind was going too fast and she needed rest, Sarah closed her eyes tightly and let it all out of her mind for the night in order to get some rest.The next morning Sarah was able to start the day strong. She started her weekend work and she was off to the races. She was preparing a defense for a very important business man from New York, this particular case was going to be tough but this was going to be easy work for a savvy woman like Sarah.
Just as she was hitting flow state an image of Charlie popped into her conscience. The events from the previous night came rushing back to her, the thought of him never overcoming his problem and never having the confidence to stand up to Hayden was too much for Sarah. It was at this moment she knew these motherly feelings were not going to go away and she knew better than to try. She was a 39 year old confident woman and very aware when something needed to be taken care of, now her mind was set, she was going to confront her son about last night when he arrived home.
---
A few hours past before Sarah heard some ruckus at the front door, it was Charlie fumbling to get the door unlocked. Sarah sat up at the kitchen table and waited for him to come through the door.
"Hey Mom!" Charlie said, right when he noticed his mother sitting in the kitchen.
"Hey Charlie, where have you been all day?" Sarah said sharply.
"I was at Hayden's house, hanging out, why?" he said with a look of concern on his face.
"Just curious," she said quietly. There was a moment of silence before Sarah piped up again, "hey, Honey, can you sit down here for a second?" Charlie's mother said pointing at the chair across from her at the kitchen table.
"Um, okay, what's up?" Charlie said as he took a seat.
Sarah's heart was pounding, she had no idea how she was going to start this conversation and she really had no idea where it was going to go.
"Well, I don't want to bother you, Honey," she said with concern.
"Mom, I don't know what you're talking about but you can tell me anything" he said with some caution.
"Okay, I'll just come out with it, last night I heard some... interesting noises coming from the basement." Sarah said looking directly at her Son. His eyes quickly widened.
"I overheard you and your friends watching porn." she said abruptly
"Mom! I'm sorry!" Charlie nearly yelled before his Mom could finish her sentence.
Sarah quickly corrected herself, "No, Honey, I'm not mad about that at all. I know boys will be boys when comes to things like that." she smiled at her Son and that seemed to calm him down.
"It wasn't the porn that bothered me, it was something I overheard Hayden say to you." Sarah clarified.
"What? What did Hayden say to me?" he retorted.
"Well, he made fun of you and Benji for... ejaculating too quickly." she said with caution and concern in her eyes, she had no idea how he was going to handle this.
"Mom! What are you saying? Look, that is just guys being guys, don't worry about it!" he said with a tone of anger in his voice. "I'm not going to talk to you about this!" Charlie said sharply as he began to get up from the kitchen chair.
"Wait!" Sarah said noticing she was scaring him off. "Let me explain." she moved her hand to his shoulder and lightly pushed him back into the chair. She needed to say something to bring this back in her favor, "Sweetie, the reason I bring this up is because your dad struggled with the same problem."
Charlie looked puzzled, "What are you talking about, Mom?"
"I'm not trying to overstep your privacy but your father struggled with self confidence and self worth due to his premature ejaculation problem." Sarah said while reaching out to hold her son's hand.
Charlie quickly pulled his hand away, "So, not only is it awkward that my mom knows I'm a premature ejaculator but now you're telling me that my lack of self confidence is hereditary? Wow, thanks Mom." he said sharply.
"No!" Sarah retorted just as sharply. "Let me finish, please." Sarah said in order to calm things down. "I was able to help your dad overcome his problem, with lots of work, he ended up becoming a fantastic lover and his confidence soared the rest of his life." Sarah didn't know how to be more tactful with this conversation.
Charlie sighed, "Well, that was great for Dad, it truly was, that makes me happy, but unfortunately that doesn't help me."
Sarah looked down at the table as a moment of silence passed, "Charlie, what if I helped you with your problem?"
"What do you mean? This is not really something my Mother can help me with." he said.
"I think I could help you in a motherly way. I don't want to cross a line but I could give you some tips and tricks that can ensure you'll overcome your problem." she said with a smile.
Charlie was dumbfounded, he just stared at his hands resting on the table. He didn't want to admit it to his Mother yet, but the idea of not having his premature ejaculation problem was tempting him to hear more from his Mother. "Mom, I don't know what to say but I don't think I'm comfortable with this." he said still looking down at his hands.
Sarah realized she was losing his interest again, she didn't know what else to say, without too much thought she made another offer, "What if Benji joins us? He sounded like he had the same issue, would that make you comfortable? It would be less pressure on you." Sarah didn't have high hopes as she made the proposition but given how close he is with his friends it might just work.
Charlie's head lifted from the table to meet his Mom's eye line, to Sarah's surprise he seemed interested, she knew they were super good friends but she had no idea they were that close. "I don't know?" he said.
"It's totally up to you, Honey. I'm your Mother and I'd do anything to make your life better, because that's what you've done for me." Sarah was pulling out everything she could think of.
That's when Charlie said something she was not expecting, "Maybe... But only if Hayden can join too."
Sarah was taken back. She really didn't like Hayden after what she heard the other night but if it meant she could help her son she was willing to compromise. "Okay, I see no problem with that!" Sarah said brightly.
Charlie sat back and rubbed his chin, "I still don't fully understand what I'm agreeing to?" he said.
"Nothing too crazy, Honey, let's just say I'll use the same techniques I used to slowly help your father. The techniques are a bit intimate but I promise to be very respectful of you... and your friends." she couldn't believe she included Benji and Hayden with all of this.
Charlie was looking more comfortable with this idea, "I feel like I could regret this but I guess we can do it."
"You won't regret it at all, Sweetie, trust me." she said. Sarah got up and hugged her son, "thank you for trusting me. I promise to take care of you." she said looking directly in his eyes.
"Okay, so how is this going to work?" Charlie was curious.
"How about tomorrow night? You gather your friends and tell them I'm going to help you guys with confidence and self worth." Sarah said with a smile.
"Well, the good news is they are going to have no problem whatsoever with this idea. They both already have a huge crush on you." he said with a little chuckle. Sarah couldn't help but to laugh a little too, she had always noticed his friends taking glances at her body. Grown men couldn't help themselves from looking at her curves so she wasn't surprised when teens try to sneak a peek.
"Okay Honey it's settled, we will start the training tomorrow night." Sarah hugged her son again. "Well, I have to get back to work and finish up my prep for this case next week, I'll talk to you soon, Sweetie." Sarah said as she left the kitchen for her office. Charlie didn't notice but his mom was beaming with a smile at the idea of helping her precious son.
Charlie remained sitting at the kitchen table, he was beyond stunned. What did he just agree to? He was certainly concerned but also excited about the idea of Hayden not being able to make fun of him for premature ejaculation, and when the time comes he could actually be a good lover to a girl. His head was spinning so hard that he decided to go lay down for a little while before calling his friends.
---
After an hour nap, Charlie woke up and felt refreshed. The first thing he needed to do was call his friends and tell them what he just signed them up for. Charlie picked up his cell phone and started a three way call with his best friends. Benji and Hayden picked up at the same time.
"Hey Charlie" he heard both voices say at once. "Can you guys meet me at the arcade in thirty minutes? I have some news for you two." Charlie said in a cryptic tone.
"Why, what's going on?" Hayden asked, of course he wouldn't just agree to the request, it was against his nature.
"You're going to want to hear this, dude, just be there." Charlie said sharply.
"Okay, fine see you there." Hayden said as he hung up.
"See you in a bit!" Benji said as he closed out his time on the call.
Charlie wasted no time getting ready. He threw on his favorite sweater and coat and headed out the door in the direction of the arcade.
---
Charlie was the first to arrive at the three friend's favorite spot, "Bob's Famous Arcade" or as the boys called it "Bob's". Charlie sat down at their favorite booth and ordered a soda. Benji was the first to arrive.
"Hey buddy." Benji said as he sat down on the other side of the booth, "what's so important, huh?" he asked his friend.
"Let's wait for Hayden to get here." Charlie said.
Not long after Hayden walked in the door. He sat down next to Benji across from Charlie, "Alright, what the big deal?"
Charlie took a long breath, he had no idea how he was going to tell them the news, so he just started talking, "I don't really know how to tell you guys this and it's a little weird but..." Charlie was interrupted by the waitress before he could finish.
"Hey boys, didn't expect to see you three tonight." the waitress said playfully, "what can I get for you two?" she was looking at Benji and Hayden knowing she already got a coke for Charlie.
The waitress was Tiffany, she was blonde, beautiful and in her late 20s. The three friends had a crush on her for years, she was a mainstay in each of their spank banks. They had a long running bet the first one to fuck her would get $100 dollars from each of the losing friends, of course the only one that had a chance was Hayden due to his higher level of confidence and looks.
"I'm good, Thanks, Tiff!" Hayden said with a smile.
"I'm all set too!" Benji followed.
"Alright, let me know if I can do anything for you." the pretty blonde waitress smiled at the boys as she walked away.
"As I was saying." Charlie said attempting to get their attention back from the hot waitress. He decided to just come out with it, "my mom heard us watching porn last night." Charlie got some enjoyment out of watching his friend's mouths gape open.
"Don't worry, she isn't mad about that at all." he reassured them.
"Okay, well that is a relief, what's going on then?" Hayden questioned.
"The problem is you, Hayden. She happened to heard you make fun of me and Benji about our premature ejaculation problem." he said looking around the room to ensure the other patrons of Bob's weren't close enough to hear the conversation.
"Oh, shit." Hayden said, he actually felt a little embarrassed. "What the problem then? Does she want me to apologize or something? Because that would be awkward." Hayden said with a smirk.
"No, actually, this is the interesting part, she wants to help." Charlie intentionally left that part vague.
"What the fuck are you talking about, Charlie?" Benji said loudly.
"Yeah, dude, what the hell?" followed Hayden.
"She offered to help me and Benji with our premature ejaculation problem, by showing is some techniques, tips, and tricks." Charlie said that last part with quote signs over his head.
"Holy fuck!" Shouted Benji. "Goddammit, I knew your Mom was cool as fuck!"
"Wait, what?" said Hayden.
"I'll tell you exactly what she told me. Tomorrow night she is going to start training me and Benji to have more stamina, she thinks it will help our self confidence."
"Oh my God! Your mom is so hot!" Benji exclaimed.
"Hey, that is my mom you're talking about." Charlie said to Benji sharply.
"What? I'm just being honest." he retorted.
Hayden chimed in, "Well that is just great for you two. What about me?"
Charlie quite liked making Hayden sweat. "Don't worry dude, I only agreed if you could join and she allowed it."
Hayden tried to hold back a huge grin, "Dude, don't scare me like that and Benji is right, your mom is hot!" he said with a laugh.
"Alright, alright, laugh it up." Charlie wasn't going to let them bother him. "Here is the deal, meet at my house tomorrow night at 9pm and then I guess it will start."
Benji and Hayden fist bumped and simultaneously agreed.
Charlie knew all too well of the poor hygiene of Benji and for his mom's sake he thought he'd give him a reminder, "Benji, make sure you shower before coming over, everyone knows how you get." Charlie ribbed his friend.
"Yea, yea, yea. I know. I'll be clean, Asshole." Benji said laughing, all while knowing Charlie was just giving him a hard time.
"Alright, I have to get back to my place and finish my homework. I figured this news was worth telling you in person. I'll see you guys tomorrow night." Charlie slapped $5 on the table to pay for his drink and tip Tiff, he stoop up and headed out the door.
---
Sarah was hiding away in her office finishing up her weekend work. It was roughly two hours before the boys would show up and she was getting nervous about the arrangement she made with her son and his friends. Sarah hadn't heard much from her son all day so she figured she would give him a visit to his room.
Sarah approached her son's room and gently knocked on his door. Charlie opened up, "Hey Mom, how are you doing?" he asked.
"I'm good, Honey. I'm excited for later. You never told me, did your friends agree to the deal?" she asked.
"Was there ever any concern, Mom?" Charlie answered her with a question.
Sarah laughed. "Okay, then. I'll see you in a bit" Sarah said as she rubbed her son's shoulder.
Sarah walked back to her bedroom and Charlie shut his door. Charlie hid it well as he talked with his mother but he was extremely nervous and was having second thoughts about the agreement to this arrangement. He was pondering all day if he had made a mistake, he had no idea what his Mom had planned and it felt like he was walking into a trap. If he didn't already invite his friends he would have certainly backed out by now.
When Sarah got back to her bedroom she was also having feelings of regret. She was very nervous about what she started but knew deep down that it was for the betterment of her son. She was committed and it was time to start getting ready.
Sarah wanted to look sexy and strong for the first session. She knew it was important to gain the high ground of power right from the start. She didn't expect this to be hard considering she was dealing with three virgins. Sarah laid her outfit on the bed and sat down at her vanity to start putting her makeup on. She was going to look like a bonafide bombshell for the boys.
She was applying her makeup as she started to think about Hayden, she still hated the thought that she would have to pleasure her son's bully but she was considering it an opportunity to embarrass Hayden too. If he was going to make fun of her son she was going to ensure that Charlie had something to make fun of him too.
If Sarah was being honest with herself, she did think Hayden was quite attractive. As the boys grew up she started to notice his attractive face and body and before she knew what an asshole he was she did like to fantasize about having her way with the young man. But all that is ancient history now that he treated her son the way he did, she was now only focused on getting her revenge on him for the bullying.
---
It was now 9pm and Charlie received a text from Hayden "Hey, we are here." it read.
"Okay, just one second." Charlie sent back.
As Charlie left his room to let his friends in he checked his Mom's office but there was no sign of her. Charlie made his way to the front door and opened it, there was Benji and Hayden eagerly waiting to come inside from the cold. Once the boys were in the house the just stood there a bit awkwardly.
"What do we do?" said Benji to break the silence.
"I'm actually not sure. I've been a bit nervous and haven't really talked to my mom today." Charlie said.
"What's that." Hayden pointed at a piece of paper on the kitchen counter.
"I don't know?" Charlie said as he headed in the direction of the note. Charlie picked up the letter, it read, "Make your way downstairs boys, everything will be all setup." Charlie face look glazed over.
"What does it say?" Benji nearly shouted.
Charlie handed him the note.
Benji and Hayden quickly read the note for themselves, "I guess we go downstairs then." said Hayden.
Charlie led his two friends down to their familiar hang out spot, as they walked down the stairs they could smell candles burning. When the three boys had made it all the way down the stairs they all took in the scene that was laid out in front of them.
There were three chairs lined up facing perpendicular to the familiar couch the boys so often played video games on. Next to the three chairs was a side table with a stopwatch, a ruler, lube, and a notepad. There was another note sitting on the coffee table, Charlie quickly headed over and picked it up. He decided to read this one out loud, it read, "Benji, take a seat on the left chair, Hayden take a seat in the middle and Charlie you sit on the right. Make yourself comfortable boys, I'll be down shortly." Charlie set the letter back down.
"Okay, I guess we know what to do." Hayden said.
The three boys did as they were told, they took their assigned seat and simply waited. It was quiet for about two minutes before they heard the door open to the basement. Each boy sat up straight in their seat at the sound of the noise.
Sarah made her way to the bottom of the stairs, each boy with his head cranked to the right in order to see her. Sarah walked over and stood directly in front of the three boys. Each boy had their mouth wide open as they took in the sight of the beautiful woman.
Sarah was wearing a tight, white blouse with enough buttons undone to show off just a little cleavage. She was also wearing a form-fitting, black pencil skirt that hugged her ass in the most tempting way. She had her beautiful brunette hair pulled back into a high ponytail, with some hair hanging loose on each side of her face. She looked every bit of a sexy librarian from the movies.
"I see you boys are good at following directions, that's a good start." Sarah said with a smirk on her face. "I sincerely, thank you for coming, but I want to be clear about one thing before we start. This is about my Son, I want him to have confidence for life and as his friends I expect you to encourage him to do so." Sarah said looking in the direction of Hayden.
"Yes Sarah." Hayden and Benji said simultaneously.
"Good." she smiled. "I know I told you boys in the past that you could call me Sarah but during these session you'll refer to me as Ma'am, understood?"
"Yes Ma'am." the three boys said at once. Sarah smirked when she noticed Charlie responding to that demand as well.
"Very good." Sarah nodded. "Alright, I'll start by going over the rules of these sessions. First and foremost I want you boys to be comfortable, so don't be shy to tell me if things are going too far for you." Sarah wasn't concerned that the boys would have any issues with what she had planned.
"These training sessions are about gaining control over your inner most urges. It all starts with your mental preparation and belief in yourself, the physical aspect comes later." Sarah had the boys full attention at this point. "Tonight is about your baseline, we can't know how far you've gone without knowing where you started, right?"
The three friends looked at each other with nervousness and excitement.
"This evening, the training session will not officially begin, you can consider tonight a warm up." she said.
Sarah noticed that the boys looked concerned after that information, "don't worry, I'll be touching each of you tonight."
Sarah noticed huge smiles on Benji and Hayden but a look of concern on Charlie. He was clearly nervous about what was happening, but Sarah was surely going to do her best to make him comfortable. She also noticed movement in the jeans of Benji and Hayden, they were starting to get very excited.
"Alright boys, take a look to your right." they did as Sarah commanded. "you'll notice there is a ruler, a stopwatch, lubrication, and a notepad. These are all the tools I need tonight. The ruler is for your manhood, you'll understand at a later date why that is important. The stopwatch and notepad are to capture your baseline and the lube is to make things a little nicer for you." Sarah smirked.
Each boy had an astonished look on their face, none of them knew what to say.
"Will these be a problem for any of you." Sarah asked full well knowing the answer.
The young men each shook their heads in unison. Sarah noticed clear and present erections in the pants of Benji and Hayden but still no movement in Charlie's pants.
Sarah pointed at the couch across the room, "Each of you will take a turn lying face up on the couch, once you are in place the baseline test will commence. I'll do my job and make sure I get an accurate timing of your stamina. Is this understood?"
Again, the boys shook their heads in unison.
"Okay, let's begin. First things first. All of you, standup and get undressed." Sarah said matter-of-factly.
The boys were too in shock to move for a few seconds after the command, finally Hayden stood up and then looked to his right and waived Benji off of his seat. Now Hayden motioned to Charlie and finally Sarah's son was standing ready to undress as well. The three friends hesitantly took their shirts off, and then started to undue their belt buckles that were holding up their jeans. Hayden was the first to push his pants to the floor and kick them to the side, Benji and Charlie followed suit. They were now only in their briefs and all them were fearful to take the next step and get naked.
"The underwear have to come off if this is going to work, come on boys." Sarah urged the three boys. While encouraging the friends Sarah couldn't help but notice the bulge in Hayden's boxer briefs, she wasn't certain yet but it appeared he had quite the tool down south.
With only a little more delay each of the boys hooked their thumbs inside the their respective waistbands and pushed their briefs to the floor and let their manhood free.
Sarah took a moment to survey the field of cocks displayed in front of her. First she examined Benji's member. He wasn't very gifted but Sarah figured he had just enough girth to please a woman if he played his cards right. She moved her gaze to Hayden's cock, she nearly gasped as she locked eyes on his magnificent prick. It was massive, veiny, and curved skyward just like Sarah loved her cock. It looked mean and bulbous, Hayden was certainly not Sarah's favorite person right now but his cock started to make her wet at the site. She took such a greedy glance at Hayden that the boys took notice of her favoritism, Sarah observed Hayden's slight smirk on his face, in order to keep control she had to move on. She moved her gaze over to her son's penis, to her surprise it was completely flaccid. Sarah was certain that this exciting proposition was enough to get any boy hard but not her son apparently, she took a look at his face and it was very clear that he was nervous about the situation, Sarah's motherly instinct was kicking in and she needed to help him feel comfortable.
"Okay, now take a seat." Sarah was enjoying the control over these young men. "Looks like somebody needs to get a little more comfortable." Sarah said looking directly at her son's member.
"Dude, how are you soft?" Hayden quietly said to Charlie on his left.
"Charlie, you nervous buddy?" Benji said, attempting to give Charlie a ribbing.
"Okay, okay. He just needs a little encouragement, that's all." Sarah said, calming the boys down.
Sarah turned around to give the boys a nice view of her ass, to their surprise she reached her hands behind her back and slowly started to lower the zipper down the middle of the pencil skirt. The boys were mesmerized as they realized this gorgeous milf was about to give them a strip tease. Sarah bent over slightly as she lowered the zipper as far as it could go, she swayed her hips back and fourth and she gently pushed down her skirt to reveal the black lacy thong covering her amazing round ass. She stepped out of the skirt all the while keeping her heels on, her now loose white blouse fell over her panties hiding what she had to offer the boys.
"Oops, I should probably take this shirt off to give you boys a better look, huh?" she phrased it as question but knew they wouldn't rebuttal. It was no surprise when they each nodded their heads in a trance.
The sexy Mom slowly opened each button until the boys could notice she was wearing a matching lacy bra. Sarah pulled off the silky blouse and gently dropped it to the floor giving the three friends a view at her beautiful large 34D breasts only hiding behind a thin piece of fabric. Sarah noticed that her strip tease was having the desired effect, Charlie's cock was coming alive. It wasn't fully hard by any means and Sarah realized she needed to take it a step further to bring her son to full mast.
Sarah slowly approached her son, she gently placed both hands just above his knees, "How are you doing Charlie, are you okay with this?" she gently asked Charlie.
"Yes, It's just a little... strange, that's all." Charlie retorted.
"There is nothing strange about a Mother taking care of her son, don't you trust me?" Sarah questioned.
"Yes, Ma'am, of course I do, this is just new for me." Charlie said.
"Lean your back against the chair, please?" Sarah asked and Charlie obliged. Sarah took her left and moved it towards Charlie's cock, when her hand got close enough she touched his ballsac ever so gently with the tips of her fingers. This sent a shockwave through Charlie's body, this was the first time any part of his genitals were touched by someone other than himself.
Sarah delicately moved her index finger to the base of his shaft, she could feel his cock quicken as she moved her finger up the length of his manhood, she was feeling all the veins and curves and she finally made it to the sensitive underside of his cock head. Sarah swirled her finger in that area for a few seconds until Charlie was fully hard, she was being careful to not get him too excited, his cock head was purple like it could explode at any moment. Sarah was impressed by his size, she was shocked that he was bigger than his own father, she was very proud of her son's cock.
Sarah backed away from Charlie before accidentally making him cum, when she made it back to her original position in front of the boys she realized Hayden and Benji were just as shocked as Charlie at what just happened.
"Okay boys, now that you're all erect I think it's time to begin the training." Sarah noticed each of their cocks pulsate in excitement of the proclamation.
"Benji, let's start with you." Sarah said quickly.
He nearly fell out of his chair, "Me? You want to start with me?"
"I don't see why not?" Sarah answered his question with a question. "Come over here and lay down." the milf said pointing at the couch. Benji didn't delay, the horny, portly boy got right up and laid down on the couch. Sarah walked over to her "tools" and started getting ready. She took the rope holding the stopwatch and threw it over her neck so that it dangled right between her tits. She then took hold of the ruler, lube, and the notepad and approached Hayden. She set everything down on the coffee table.
"First we need to get a measurement." Sarah said as she placed the ruler so that the edge was pressed against the length Benji's stiff penis. "About 5 inches" she announced as she wrote it down in the notebook, "not bad, you have some nice girth too." Sarah was hardly impressed with his willy but didn't want to make him feel bad.
"Okay, Benji, when I start the timer I'm going to jerk you off, as soon as you cum the timer stops so try and hold off as best you can, okay?" Sarah was prepping him for the most pleasure he will have to this point in his life.
"I'm ready." Benji said with a shaky voice.
"Okay, here we go." Sarah said as Benji's cock started to bounce uncontrollably.
Sarah pumped a couple drops of cold lube directly on his cock head. She reached down and started the timer, Benji's moment of truth had arrived. Sarah rubbed the lube from his head and lathered it over the rest of his penis with her right hand. Benji let out a loud moan of pleasure, it was the best feeling he ever had bar none. Sarah made a couple of firm strokes to his phallus and she could already tell he wasn't going to last much longer.
She stopped her hand at the top of his penis and started to swirl around her thumb on the sensitive underside of his head, she then took her left and cupped his balls. The young man moaned so loud it nearly came out as a yell, Sarah couldn't help but smirk at the pleasure she was bringing this virgin. The power she felt over him was making her wet, but she needed to stay focused, it was time to make this boy cum.
She started to massage his balls and stroke his knob at the same time, Benji's hips started thrusting in unison with the jerks of his dick. He was getting close, so Sarah stroked his shaft even harder, only a few more moments passed before his body started gyrating wildly, he finally pressed his hips skyward and let out spurt after spurt of creamy cum all over his chest. Sarah stopped the timer with her left hand as her right hand slowly stroked his penis until every drop was out of him.
"Oh my God! That was amazing" Benji said through bated breath as he tried to calm back down from the experience.
"I'm glad you enjoyed it, but most of all we have your baseline!" Sarah said with excitement. "You lasted 34 seconds. Not bad for the first time." Sarah said as a white lie. She noticed Hayden snicker at his results, "no laughing! Just wait until training is done, he will last as long as he needs." Sarah said smiling at Benji. "Okay, clean up and return to your seat." Sarah commanded. Benji grabbed a towel from the coffee table and sat back down in his chair.
At this moment Sarah was conflicted, she knew it was time to take care of Hayden. She didn't like him for bullying her son but the new discovery of his beautiful cock had her intrigued. This was her chance to embarrass him, she was determined to make him cum quickly so that Charlie and Benji would have a chance to laugh at him, she was excited to provide that opportunity for her son.
"Okay Hayden your turn, come over and lay down on the couch." Sarah commanded.
"Yes Ma'am." Hayden said confidently and he quickly made his way to the couch, as an attempted power play he purposely waved his massive member as close as he could to Sarah's face, she had to move her head out of the way before getting slapped by the gorgeous boner. Sarah had dodged his offensive maneuver and now Hayden was finally laying down in correct arragement. "This cocksure kid is going to get what he deserves", she thought to herself.
Sarah kneeled down and positioned herself next to him. Now that her face was so close to his thunderous cock it was even more majestic than she thought. Sarah started to tremble in excitement to touch his amazing ramrod, she felt her control slipping, she needed to focus, "You're in control here, not him." Sarah thought to herself for reassurance.
"Time for the measurement." Sarah stated. She pressed the edge of the ruler against the length of his angry cock. "Wow, it's 11 inches." Sarah said with a tremble in her voice. Hayden had a large smile on his face, he was clearly proud of himself and there was no reason he shouldn't be, it was the most impressive cock Sarah had ever seen.
Sarah repeated the rules to Hayden, "Okay, Hayden, when I start the timer I'm going to jerk you off, as soon as you cum the timer stops so try and hold off as best you can, okay?" Hayden nodded his head with a smirk.
Sarah started off the same way she did for Benji, she pumped some lube directly on his cock head. Before she started she gave herself a quick internal pep talk, "Okay, let's make this cocky kid cum fast, it'll make Charlie feel better." with that she started work on his war hammer.
Sarah started by rubbing the lube down the length of the large prick. Hayden let out a grunt of pleasure, one grunt for each of the first three jerks to his cock. It was a good start for Sarah, she had him under her control now. The kneeling milf moved her left hand to his large gonads and began to massage, this somehow made his already rock hard cock into certified titanium. Sarah used what she thought would be the finishing technique, she moved her right thumb and pressed it tightly against the underside of his cock and started to stroke. She was prepping for loud moans but instead Hayden threw his hands behind his head as if he were getting ready to watch a movie, he had a large grin on his face. That's when Sarah realized that this wasn't going to be so easy.
Sarah moved her left hand off his balls and up to his shaft in order to help out her right hand, she now had both hands stroking his cock but it was so large that there was room for at least one more hand. She used this technique for at least one minute and now Hayden's eyes were starting to roll back in pleasure. Sarah quickly took her right hand off his cock to retrieve more lube, she got three pumps worth of lube in her hand before spreading it on the gorgeous cock with both hands. She started to feel his hips move with the jerking, she was getting close but she needed to get better leverage to make this cock cum.
She moved her hands off his cock momentarily, Sarah stood up and sat on the couch between his legs, she lifted his legs over her own in hopes to get a better grip on his cock. She firmly gripped his member and started the stroking again. This new angle was working, Hayden's grunts got louder and his hips started moving more violently. Sarah decided to pull out one more trick, she pressed his cock tightly up against his stomach with her left hand, she leaned in and spit directly on his ballsac, she moved up and spit again, this time on his mean shaft. Sarah leaned back and started stroking with all she had. That trick worked like a charm, Hayden was bucking like a bronco.
Sarah took her left and tightly grabbed his balls and pulled him down firmly to the couch, while holding him down by his gonads with her left hand, she aggressively jerked him off with her right. That was all it took, Hayden let out a thunderous grunt and spewed his load all over his chest. Sarah continued to stroke until his orgasm subsided, she even carried on past his orgasm to give him a little head torture. After all the cum was gone she squeezed his head tightly which made him jump in both pleasure and pain.
Sarah stopped the timer. "You lasted 8 minutes and 26 seconds."
Benji started clapping, "Good job, Hayden."
"Kiss ass." Sarah thought to herself. She was devastated that she couldn't get him to cum quicker, her plan had more than failed, if anything Hayden was toying with her. Sarah felt bad for Charlie's sake, she felt like she let him down. She was really hoping to take that opportunity to make Charlie feel better, but Hayden was a better match than she expected.
"Okay, clean up and take your seat." Sarah commanded.
Hayden popped and again said, "Yes Ma'am."
The good news is that it was finally time for the star of the show, her son. "Are you ready Charlie?" Sarah asked.
"I think so, Mom." Charlie replied.
"Come lay down." Sarah said.
Charlie got up and made his way to the couch, he gently laid down on his back. Sarah noticed as he laid back the his cock was already leaking precum, this was not a great sign for him lasting long but she was going to give him the time of his life.
"Okay, Honey, let's get you measured." Sarah placed the ruler's edge against the length of her son's cock. "Oh my! It's 8 inches. Very nice!" Sarah said. Sarah leaned in close to her son's ear, "You know, you're even bigger than your father, I'm so proud of you." Charlie's mother whispered in his ear. She noticed his cock buck when she told him that news.
Sarah again stated to rules before beginning. "Okay, Honey, when I start the timer I'm going to jerk you off, as soon as you cum the timer stops so try and hold off as best you can, okay?" Charlie nodded.
Sarah wanted to do something special for her son, so right before starting she reached her hand behind her back and unclasped her bra. Charlie's mouth gaped open as the site of his mother's beautiful breasts came into view. Benji and Hayden leaned forward trying to get a good view but Sarah positioned herself so that only her son could get a view of her voluptuous breasts.
"Do you want to touch them, Honey?" Sarah asked.
"Yes Ma'am." Charlie replied.
He reached out with his left hand and cupped her right breast. Not to Sarah's surprise this made Charlie's cock bounce and leak even more precum. It was time to get this started before he loses control.
Sarah started the stopwatch and pumped lube on his cock, she hadn't even touched him yet and he was already letting out little whimpers of pleasure. Sarah tightly grabbed his cock and rubbed the lube against the length of his impressive cock. She treated him just like the other boys up to this point by grabbing his ball with her left hand. She was gently massing and playing with the tip of his cock with her right thumb. Charlie started to buck wildly just like Benji had at this point. It was clear her son was certainly a premature ejaculator, but she was going to give her son some special treatment even if he came early.
It was obvious that Charlie didn't have much time left based on how hard his cock was pulsating in her hands. Sarah quickly let go of his cock and let it bounce fiercely in the open wind. For a moment Charlie that he had done something wrong but he was in for the feeling of his life. Sarah leaned forward, she first took tight control of the base of his cock and stood his member up straight and true as she could, she continued to lean forward until her face was inches from his pulsating cock. Much to Charlie's surprise his mother sensually kissed the sensitive part of his cock head, she then stuck out her tongue and started licking it softly, her right hand was not starting to stroke his shaft again. Charlie let out the largest moan of the night, his hips started bucking so hard that Sarah had to hold him down with her left hand. She continued to stroke and lick until a fountain of cum started gushing from his cock head. It was the biggest load of the evening by far. He just kept cumming and cumming, he even got some spunk on his mother's forehead.
Finally the orgasm subsided and Sarah let go of his thoroughly pleasured cock. Sarah stopped the timer, "Oh, 58 seconds, looks like you were just shy of a minute." Sarah rubbed his thigh to make him feel better about the results. Sarah grabbed a towel from the table and cleaned the cum off of her son, another pleasure she didn't give the other boys.
"Okay, Honey, return to your seat, please." Sarah asked. Charlie complied and took his seat next to his friends who were both very jealous of the treatment he just received.Sarah put her bra back on before facing the boys in their original position. "Great job boys, I think this was a first great session. Are you guys willing to continue the training?" Sarah asked knowing the answer.
"Hell yes!" each boy said simultaneously.
"Good. How about this time next week? That'll give you guys sometime to discuss tonight and think about how to improve before the real lessons start." Sarah said.
"Sounds good to us." Hayden spoke for the group.
Sarah was grabbing all of her belongings when she noticed Benji and Hayden were fully erect again, she didn't consider this a large surprise.
"Okay, boys see you next week." Sarah said on her way out, but she didn't leave without teasing Charlie's friends a little more. She walked over and grabbed Hayden's cock with her right and and Charlie's with her left, she gave them both a couple pumps and then flicked the tips, the difference in cock size made Sarah chuckle, "You boys will have to take care of those yourself now." Sarah said with a smirk. The milf had one more token of advice before leaving, "Don't forget boys, confidence starts with stamina!" she said as she headed up the stairs for the night.
Once Sarah was out of ear shot the boys jumped out of their chairs fully naked and started high fiving each other. "I can't believe this is happening." Benji exclaimed.
"Dude, your mom is officially the coolest Mom in all of history." Hayden said to Charlie.
"Yea, I guess she is." Charlie agreed with a smile on his face.
The three fully naked boys got up and sat on the couch they had just been pleasured on and talked about what just happened the rest of the night, and jerked off a couple more times too. They couldn't wait for next week and they had no idea what is waiting for them.