Charlie was fast asleep in his bedroom resting after the most sexually charged night of his life. It was just 10 hours ago when his mother started stamina training lessons with his two best friends and their lives were going to change so much from the experience, all for the better.
It was around 10:30am when Charlie was jarred awake by a knock at his door.
"Charlie, can I come in, please?"
"Umm.. sure, come on in." Charlie said loudly through a yawn.
Sarah slowly opened the bedroom door and took notice of her son stretching out under a thin sheet as he was just waking up, "Good morning, Honey. How are you feeling?" Sarah said as she got down on her knees next to his bed.
"Good, still a little tired after last night."
Sarah smiled, "yeah, I bet you are. That was a lot of fun, wasn't it?"
"It sure was, Mom. Thanks again for helping us with our problem." Charlie wanted to ensure she knew how grateful he and his friends were.
"Charlie, it's my pleasure to help you and if it makes you comfortable I'm happy to have your friends their too." Sarah said as she rubbed his shoulder.
Sarah paused for a moment, "I just wanted to come and make sure you were still feeling good about things and that I haven't overstepped."
Charlie pushed himself up on his elbows, "No! not at all, Mom. I'm so happy we are doing this!" he said sharply.
Sarah laughed at his candor, "I'm glad to hear it. You might be surprised but this process is fun for me too." they both chuckled.
"Don't stay in bed too long, breakfast is almost ready." Sarah said to her shirtless son as she stood up to leave his room.
While she was walking out she noticed that Charlie had morning wood, "make sure you take care of that before coming to the kitchen." she said pointing at his erection.
Charlie quickly tried to cover it up with his hands.
Sarah laughed, "Really? After last night you're going to be shy now?"
Charlie laughed, "yeah, well I'm still getting used to this." he said as he slowly lifted his hands off of his hard penis.
"Like I said, make sure you deal with it before leaving your bedroom." Sarah said in a playful tone as she walked out of his room.
Charlie has always listened to his mother and this was no exception, he pulled out his cock and feverishly masturbated to the thoughts of his mother from the previous night.
---
About 20 minutes later Charlie had finally made his way to the kitchen to greet his mother, "Thanks for making breakfast, Mom." he said as he turned the corner to the kitchen.
"My pleasure, and you made it just in time." Sarah was setting his plate of pancakes and bacon on the table. She walked back up to the counter and made up a plate of food for herself. After everything was all set she took a seat across from Charlie on the table.
Sarah pipped up, "I was thinking about what to do today, most of my work is all finished up so I have the day free. Do you want to hang out with your mother today?"
"Sure, I've got nothing going on. What do you want to do?" Charlie asked.
"I have one errand to run, but after that I'm open for anything. Maybe we go to you and your friend's favorite place and play some arcade games?" Sarah said with a smile.
"You want to go to Bob's with me?" Charlie was shocked.
"Why not? You guys always make it sound so fun." she laughed.
"Alright, if you're okay getting your butt kicked in Street Soldier." which was Charlie's favorite game at the arcade.
"I think I can take you just fine, little guy." Sarah said while laughing.
The pair finished up breakfast and agreed to go finish up getting ready before heading out for the day.
---
Charlie was hanging out in the living room awaiting his mother. When she finally emerged from her bedroom and entered the living room, he couldn't help but notice how beautiful his mother was. After last night he was seeing her in a whole new light, he admired her ass in the tight fitting jeans and had a quick look at her breasts in a tight t-shirt before she slipped her coat on.
"Are you ready to go?" Sarah said to her son.
This snapped him out of his lustful trance, "Yes, I'm ready, sorry!"
Sarah laughed, "Aright, let's go then!" they both walked out to the garage and headed out to enjoy some time together on this beautiful Sunday.
It was about a 20 minute drive to their first location, in lazy Sunday fashion it never occurred to Charlie to ask where they were going until they arrived at Sarah's favorite boutique. That's when he realized she needed to go clothes shopping, Charlie was already regretting the choice to come.
"You're going shopping for clothes?" Charlie murmured.
"Yes, I need to get some new clothes before my big case next week. I didn't think you would mind, as a matter of fact I thought you could help me pick it out." Sarah said as she rubbed Charlie's upper thigh from the driver seat.
"Yeah, sure, I can do that," Charlie stammered as he got out of the car.
Once in the store, Sarah went right back to the high-end business attire. She was flipping through the racks and occasionally picking some off and throwing them over her arm. "What do you think of this one, Charlie?" she was showing him a tight navy blue pencil skirt, much like the one she was wearing last night.
"I think that would look great on you, Mom." he said quietly so that the workers couldn't hear him.
"Let's find out, come on." Sarah said walking towards the dressing rooms. The 'doors' on the these dressing rooms were curtains that you could slide over to get in. Sarah walked into the third dressing room down the hall, once inside she peeked from behind the curtain to see if any employees were looking. "C'mon, Charlie. Get in here." she was waving him in the room.
"What? No!" he said in quiet but stern voice.
"Do I look like I'm asking, young man?" Sarah said in similarly stern voice.
Charlie relented, he took a peek over his shoulder and quickly ran into the dressing room with his mom. After closing the curtain behind him he said, "There, are you happy now?"
"Why yes I am, thank you." Sarah said with a smile. "Isn't this fun?"
Charlie didn't know what to say, all he could do was smile at his mother.
"Okay, what should I try on first?" Sarah asked Charlie.
Charlie looked at the clothes in her arms sheepishly, "umm... I guess that one." he said pointing at the chiffon light blue blouse.
"Good choice." Sarah said as she started pulling off her coat and putting it up on the hanger. She started taking off her shirt in the most sexy way, it was very tight so she had to cross her arms and pull it over her head. Sarah was wearing a thin bra that hardly seemed equipped to hold up her tits. Charlie couldn't look away, he was taking in the sight for everything it was worth and now he was feeling a stirring in his pants.
Sarah slipped on the blouse and without warning to Charlie she quickly unzipped her jeans and pushed them to the floor. Charlie took in the view of his mother's black thong that didn't cover any of her glorious ass. She picked up the navy blue pencil skirt and pulled it over her hips and tightly squeezed in. "Can you zip me up?" Sarah asked turning her back towards him.
The skirt was just like the one she was wearing last night, it had the zipper that needed to go right over her ass. Charlie gulped and reached his hands toward the zipper. He pulled the top of the skirt together and zipped it up over his mother's voluptuous ass. "There you go," Charlie said with a shaky voice.
"Thanks, Sweetie." his mother said as she turned around to view herself in the mirror. "How do I look?" she was tightly pressing her hands on her hips and posing for Charlie.
"You look wonderful, Mom. Beyond beautiful."
Sarah smiled, "awe, you're sweet. How does my ass look?" she quickly asked as she turned around.
"What can I say? It looks amazing!"
Sarah turned around and looked at his very apparent erection hiding behind his denim. "I can tell you like it." Sarah said with a chuckle. Charlie again tried to put his hands over his boner, but realized it was futile.
"Well, you look hot and it's only natural." Charlie said in defense of his situation.
"I'm only playing, Honey. You getting excited to see me like this is only validation that I should buy the outfit." Sarah smiled and gave him a quick pat on the crotch. Charlie nearly grunted from the slight touch his mother gave him. "Easy there, Sweetie. You are reminding me why we are doing the stamina training." Sarah poked loving fun at her son.
Sarah told Charlie to unzip the skirt and pull it to the ground, to which he happily complied. She then unbuttoned her blouse and hung it up with the skirt, "I'll be buying these then." Sarah said in nothing but her underwear. Sarah finished getting dressed back up in her casual clothes she came in, "Okay, I'm going to sneak out, you wait in here until you lose that boner, okay?" Sarah said with a little laugh.
"Ugh, okay." Charlie rolled his eyes as he watched his mom leave the dressing room. Charlie debated with himself whether he should just whip it out and masturbate right in the dressing room. "It might be the quickest way to get rid of this thing." he thought to himself. Fortunately for him he was able to calm himself down after about 5 minutes. Once the erection wore off he exited the dressing room and met up with his mom at the register where she was purchasing the clothes.
"I see you've got control of yourself." she said looking down at his denim cock, quietly enough so the employee couldn't hear as she was swiping her card in the register.
Charlie just smiled at his mom and shook his head.
"You are all set, thanks for stopping in today you two." the lady at the register said as she handed Sarah the receipt.
"Thank you for helping me pick out this outfit, Charlie." Sarah said once they were back in the Audi Q8.
"No problem, Mom. Always happy to help." Charlie said with a wink.
Sarah laughed, "Alright, wanna go to Bob's and have a little fun?"
"Sure, let's do that." Charlie said.
----
This was the first time Sarah had ever made it to "Bob's", her son's favorite place to hang out. Once she and Charlie walked in she could tell right away why this was a boy's heaven on earth. Arcade games were everywhere, there is pinball, pool tables, it was essentially a boys club through and through.
"Alright, Honey. What should we play first? Street Soldier?" Sarah said having no idea what that meant.
"Hell yes!" Charlie said leading her over to the game.
The two of them played video games for almost an hour, they moved from pinball to darts and back to video games. Charlie could tell his mother was getting tired of all the gaming.
"Want to take a seat for a bit?" Charlie asked.
"Sure, that sounds nice." she responded.
Charlie led her to his favorite booth, the exact one he gave the news of the impending stamina lessons to his friends. "Let's sit here, this is my favorite spot." Sarah and Charlie sat down at the booth.
They were there for only one minute before Tiffany showed up to take their order, "Hey Charlie, who is this lovely lady?" the blonde waitress asked.
"Hey Tiff, this is my mother, isn't she beautiful?" Charlie said with a smile.
"She sure is," Tiffany said reaching out to shake Sarah's hand.
Sarah took her hand, "Well, it takes one to know one."
"Awe, your mom is really nice." the waitress said smiling at Charlie. "What can I get for you two?" She asked.
"I'll take a lemonade." Sarah said.
"Make that two." her son announced.
"Coming right up." Tiffany said. As she made her way back to the bar Charlie couldn't help but check her out. This was normal routine for Charlie and his friends when they were at Bob's, but he forgot for a moment that he was there with his mother this time.
"Hey, eyes over here, young man." his mother said with a smile.
Charlie quickly looked back knowing he was caught, "Oops, sorry Mom."
"I understand, she is really cute, I would check her out too if I were you."
Charlie smile, "If I'm being honest, me and the guys have crushes on her. We have for a long time."
Sarah smiled, "Really? Even Hayden huh?" she wasn't sure why she asked that but she couldn't take it back.
Charlie paused for a second, "Yeah, even Hayden." There was some silence at the table for just a moment. "Hey, Mom." Charlie broke the silence.
"Yes, Darling."
"Can I ask you a question about last night?"
"Of course, anything!" Sarah said in a matter-of-fact tone.
Charlie took a deep breath, "I saw the way you looked at Hayden yesterday, specially the way you looked at his... penis." he stuttered out.
Sarah was taken back, "Honey, what are you trying to say?" she couldn't come up with anything better to say.
"I don't know? This sounds stupid but I'm worried that you like him more than me." Charlie said looking down at the table.
Sarah's heart nearly broke, she couldn't believe she was letting that asshole get to her son, even through her. Sarah quickly grabbed both of Charlie's hands, "Sweetie, listen to me now, and listen to me good. Nobody, I mean nobody, will ever take your place in my heart. Do you hear me?" Sarah said sharply.
Charlie's eyes were still down at the table, "Yeah, I hear you."
"Charlie, look at me." she commanded and he obeyed. "I love you with all my heart and I'm so sorry I made you feel that way. Please believe me when I say that Hayden will never hold a candle to what you are to me, understand?"
Charlie lifted his head, "I believe you Mom, thank you." Charlie smiled.
"I appreciate that Mom, and I'm also trying to be honest with you too, I'm not blind, I can see Hayden's cock. I know woman like big ones, I understand if you're intrigued." Charlie was trying to be understanding.
"Stop right there, Sweetie." Sarah commanded. "I want you to know that you have a large penis that is capable of bringing woman so much pleasure. These training sessions aren't about Hayden's cock and God knows they aren't about Benji's cock. They are about you believing in yourself. That is the only reason I'm doing this and you need to believe that." Sarah said forcefully.
"I believe you, Mom." Charlie said with adoration.
"I think we should get back to talking about us, what do you say?" Sarah asked.
"That sound good." he responded.
---
Roughly 30 minutes passed and suddenly Sarah got a bright idea, "Hey Charlie, I can tell you like Tiffany, why don't you ask her out?"
"What? No way!" Charlie retorted.
"Why not? What's the worse that can happen." Sarah asked.
"Oh, I don't know? She could say no!" Charlie said with sarcasm in his voice.
"I'll put it this way, asking her out is part of your training, you have to be okay with rejection, it's just a part of life, sometimes people will tell you no but you have to keep moving." Sarah said.
"I don't know, Mom." he said.
"Please do it. Do it for your mother!" Sarah urged him.
"You're going to play that card? You know I can't say no to that." Charlie sat in silence for a few seconds, "Okay, fine, I'll do it." he said.
"Yes! Thank you, Honey. This will be so good for you." Sarah said. "Quick she's over at the bar you should go now."
Charlie looked over and noticed that now was as good of time as any, "Okay, wish me luck." he said as he pushed himself out of the booth to approach Tiffany.
Sarah could see him talking to Tiffany, she couldn't make out what was being said but she was doing her best to read the body language of the conversation. They were both laughing, it seemed that Charlie was doing a great job, but all of the sudden she noticed Tiffany getting a little awkward. She knew that body language because that was the same way she looked when she turned down guys at work. Sarah could tell this wasn't going well for Charlie. They talked for a couple more minutes and he headed back to the table looking a little dejected, Charlie plopped himself down at the table.
"How'd it go, Honey?" Sarah asked knowing the answer.
"Not great, Mom. She said it was really sweet of me to ask but I'm too young for her. I knew that would happen." he said with sadness in his voice.
"Charlie. Look at me." Sarah said, "I'm so proud of you, like I said before you went over there, rejection is part of the process. You just gained so much confidence from that and you don't even know it yet."
"If you say so, Mom."
"I do say so. As a matter of fact, let's get out of here, I'll prove it to you." Sarah grabbed enough money out of her purse to pay for the lemonade and a tip for Tiffany, she stood up out of the booth and waited for Charlie to follow her out.
It was a long ride home, Charlie wasn't saying anything and Sarah was trying to cheer him up the whole time.
"Technically she didn't say no, if you think about it. She just said you were too young, I bet in couple of years she will love to go out with you." Sarah said as she put her hands on his shoulder.
"I appreciate it, Mom, but I don't want to take about this anymore. Let's just get home I want to forget this every happened." Charlie said.
"Okay," was all Sarah could say back. She started to feel bad that he was taking it so hard, she decided that this was a great opportunity to give him a private lesson when they arrived home, "That will surely cheer him up." she thought.
---
Charlie was completely unaware that his mother had plans to reward him for his courageousness he showed at Bob's. When they finally got home Charlie rushed in the house and went right to his room. Sarah followed after him, she knocked on his door, "Get out here right now, mister, there is no way I'm letting that ruin our night."
Charlie opened his door, "Why did you make me do that, Mom? That was so embarrassing." he said.
"The courage you showed this evening deserves a reward." Sarah said.
"What are you talking about?"
"I'm going to give you a couple tips tonight," Sarah said, "have you taken a shower after last night?"
Charlie looked confused, "No, why?"
Sarah grabbed him by the hand and walked him to the bathroom, once they were both in the washroom Sarah said, "I'm giving you a private lesson right now."
Charlie didn't know what to say, he just stared at her slack-jawed.
"Here are the rules, stand still and do what I say, understand?" Sarah commanded.
Charlie just nodded his head.
Sarah moved really close to Charlie, she reached her hands down and pulled his sweater over his head, he was now bare chested. She then got down on her knees and started unbuckling his belt, she yanked it off and threw it to the floor. Sarah then gently undid the button on his jeans and slowly unzipped the fly. With just a light tug she pulled his jeans to the floor.
Charlie was still in shock, one minute ago he was mourning the fact that Tiffany rejected him at Bob's, now he was standing in front of his mother with nothing but his underwear on and now his cock was starting to harden.
Sarah noticed the bulge emerging in his boxer briefs, without anymore delay she reached her fingers between his skin and the waistband of his underwear and released his cock into the open wind. As she pulled his underwear off his cock popped out like a jack-in-the-box toy, it almost hit her face but just nearly missed. Sarah stood up so that she was looking directly into her son's eyes. She moved her hands to each side of his face and then pulled him in for a kiss on the mouth, the kiss lingered for a couple seconds before she pulled away, "I love you with all of my heart, Sweetie."
Charlie finally opened his eyes after the kiss, "I love you too, Mom."
Sarah turned toward the shower, she bent over so that her ass was pressed up against Charlie's groin. While she was in this position she was able to turn the knobs of the shower to start the hot water. Once it was warm enough she commanded Charlie to get in and he obeyed. After Charlie was situated in the shower Sarah started undressing, Charlie was in shock as he watched his mother push her jeans to the floor and quickly pull off her shirt, she unclasped her bra and removed her panties. Sarah was completely nude in front of her son.