Family Fun

This is my first story so I hope everyone likes it. Constructive criticism is always welcome as well as your comments. Ideas for potential sequels are also welcome.

*****************

John was your average 21 year old college guy. He had decent looks and a nice build. He considered himself to be smarter than most people in college. He didn't really study very much, mostly because he grasped the material very easily. He still lived at home with his mother and brother. His mother worked long hours supporting the family as a single parent and his brother had chosen to take the basement for himself, which afforded John a lot of privacy. His grandparents had paid for his schooling so there was not much need to work. He also didn't have girlfriend gave him a lot of free time. He would use this time to masturbate frequently, usually about two to three times a day.

It was a regular Friday for John. He had an exam earlier that day and was now on his way home. He was certain that he passed the exam so he didn't have many worries. He had spent the last 2 days studying. He had the urge to masturbate many times, however logic won out in the end and he decided to wait until after the exam to pleasure himself. He knew that his orgasm would be better anyway.

Finally home, John burst through the door of his room in excitement, "I am so fucking horny!" he thought to himself.

He could feel his penis stiffening through his jeans and knew he needed a release. He quickly removed his white T-shirt and tossed it aside. He began unbuttoning his jeans, pulled them down and threw them aside as well. He looked down and saw his fully erect penis.

At first glance John seems like he had a lot going for him. Decent looks, good body and a bright future. However, looking closer, there is one shortcoming that John had to overcome his whole life. He had a small penis. The years of being naked in locker rooms and all the porn he watched had confirmed it.

John's penis was as hard as it could be. He just wanted to grab hold of it and stroke it until he blew his load all over the room. John had another idea however. He walked across his room, his little member bobbing up and down as he tried to avoid stepping over the clutter all over the floor. He was a bit of a messy guy. He arrived at his closet and began searching for something, moving aside piles of clothes and shoes until he found what he was looking for. It was his fleshlight. He picked it up and looked it over.

He remember the day he bought it, and how embarrassed he was to ask for one. The woman in the store was very nice and accommodating and gave him a great service. She wasn't incredibly attractive but she had a large pair of breasts, and he tried very hard not to get an erection in front of her. He couldn't help but feel sleazy and pathetic for being there and asking for one. Nonetheless, it turned out to be a great purchase and one he enjoyed using to this day.

He walked over to his bed, admiring the toy. He knew it was way too big for him, but he didn't care. Once he reached his bed, he lifted the mattress and placed the fleshlight between it. He knelt down in front of it, and slowly bent over to retrieve a bottle of lube he hid under his bed and began to apply a very generous amount to his hard cock. He slowly lined up his penis to the hole of the toy and gave it a quick thrust. He had achieved penetration. He began to thrust, closed his eyes and let a wave of pleasure wash over him

***********

John's mother was exhausted. She managed to get the rest of her Friday afternoon off and eagerly drove home so she could get out of those painful heels and bra and finally relax. As a single mother she worked incredibly hard

John's father had left them many years ago. She was lucky that she had a good job, but being left to raise two sons on her own was exhausting and difficult.

She was incredibly beautiful and she knew it. She had a great body, beautiful shapely ass and enormous EE breasts. Fake of course, and paid for by her ex-husband before he left, but she enjoyed them. It was he who had recommended she get them. It was definitely more of a gift for himself, but she did love to watch his dick disappear every time she would titty fuck him. It would make him cum so fast.

"Finally home." She said to herself as she pulled up to her driveway. She put the car in park, got out and walked to the front door. Her feet were killing her. Once inside, she kicked off her heels and quickly ran upstairs to remove her very constricting bra. The twins needed to be free.

As she walked down the hall to her room, she suddenly became aware of heavy breathing and what sounded like a sloshing or squishing sound, "Maybe John is home early?" she thought.

As she approached his room she could hear the sound getting louder. She noticed his door was closed and realized that her son must be in his room. She wanted to say hi before she got undressed and walked towards his room. When she got to his door, she opened it quietly. She was really hoping to scare him. When she looked inside she finally realized what he was doing and she stood there, frozen.

In full view was her eldest son, on his knees, thrusting away at what looked like his mattress. She couldn't see too much of him as he was at an angle, mostly his ass moving back and forth, a quick glimpse of his balls, but that was it. He tilted his head back slightly, his eyes closed, his breathing heavy and she could see the sweat glistening all over his body. He was in a state of bliss and he was oblivious to her presence.

She wanted to turn away, but she couldn't help herself. She was mesmerized at what she was seeing. She wasn't there for more than twenty seconds when John picked up the pace and she realized that he was about to climax. She then noticed that he wasn't fucking the mattress as she first thought, but he was using a sex toy instead.

She heard John grunt and realized that his orgasm was on its way.

"Oh fuck!" she exclaimed, not knowing she said it that loudly. That was enough to bring John back to reality.

"Mom!" he said in disbelief, his minuscule member slipping out of his fleshlight with ease as he turned to face her.

"I was just...," she started but quickly froze. Her gaze slowly moved from her sons shocked expression down to his penis. Before she could finish her thought, her son began to shoot ropes of cum in her direction. She couldn't believe with how much force they were coming at her. He must have shot five or six heavy streams before she could process it. Then she noticed something else. She couldn't believe it at first and then it became all too real. There, attached to her son, was the weapon that had created such a mess. She couldn't believe it, she wouldn't, but there it was. Her son had an incredibly small penis! She had never seen one that small before. It was obvious that her son was fully erect, but she couldn't believe that a penis could be that small. Yes, her ex was on the smaller side, something she had to endure constantly whenever he wanted to fuck her. Compared to her son however, he was huge

John couldn't process what happened. He was like a deer in the headlights. After a few seconds, he finally got hold of his mind and saw that his mother had been watching him as he came. His penis began to shrivel back to its flaccid state. He quickly covered up with two hands, even though he clearly needed just one, "Leave!" He yelled, wanting his mother to go so she could save him even more embarrassment.

"I'm sorry." Is all she could say as she left the room. She had been in awkward situations before, but this was something new.

She rushed into her room and locked her door. She began to fully process what had happened. She was in disbelief. She had witnessed her son orgasm. Even more pressing however was that her son had a very small penis. She had never seen him naked as an adult, only when he was younger. She had caught her younger son naked before about year ago. He however, had a large member. She was very impressed with it. She just assumed that John had a decent size himself.

It was a relief to finally take off her bra and the rest of her clothes. She couldn't shake the image of his small penis from her mind though. When she removed her skirt, she noticed that her panties were soaked with her juices.

"It can't be," She thought. "Small dicks don't turn me on!" She had never enjoyed a small penis before. All the while she endured her ex husbands small cock, she would always make it a point to go out and find hung men to fuck. That was the only way she could get off. She never felt guilty, her ex was an asshole and he deserved it. "He got what was coming to him." She would say to herself. This was different. She was now intrigued by her sons little member and she needed to know more!

*********

John had secluded himself inside his room. He was still so embarrassed. His mother had seen his penis and even worse, seen him cum. He had always been self conscious about his small penis. All the kids would make fun of it when he was younger. They had nicknamed it stumpy because when it was soft it only barely poked out.

After a few hours trapped in his room John heard a knock on his door.

"Oh God." He whispered to himself

"John honey," His mom said through the door. "We need to talk."

"I'm busy!" He replied. He didn't want anything to do with this. He wanted to stay locked up in his room and bury his head in his pillow.

"Stop being that way," She replied. "We need to talk".

John slowly got up from his bed and slumped his way to the door. He opened it slowly, dreading what was to come. Head down, he answered, "What?" trying not to make eye contact with her. After not hearing a response for about 5 seconds he began to look up. To his surprise his mother was standing there wearing nothing but a very revealing robe. His mom was a busty woman, he had always known that. This, however, left little to the imagination.

She pushed her way through his door and began to speak "Look," She started, "About before. I just wanted to say that I am really sorry about what happened. I should have respected your privacy and knocked before I came in." She was sincere in her apology, but she did enjoy the show he gave her. "Do you want to talk about what happened?" She finished.

John cringed. He didn't know what to say. All he wanted was to forget about what happened.

"Its OK," She continued. "You did nothing wrong. It's completely natural. You aren't the first son of mine I caught in that situation before." She said smirking. She wanted him to feel as comfortable as possible, but also a little on edge. She was enjoying herself.

"Really?" He replied. He hadn't known that.

"Of course. Boys will be boys. I know it's fun for you guys. All guys do that. Although maybe not like you were." She said with a smile.

John had trouble listening to this. It made him very uncomfortable. But his mother seemed OK with everything that had happened. He was happy that at least she wasn't mad or upset.

"Thanks mom," He said with the slightest trace of a smile.

"No problem sweetie," She was happy that her son was feeling more at ease, but she was still a little curious. "Do you mind if I ask you something?"

John wasn't sure that he wanted to answer any questions. He just wanted to put this behind him. She was his mother however and she was cool with the whole situation so he agreed to answer.

"I wanted to know what you were using to pleasure yourself with? It looked like you were thrusting into something?"

John's face turned red. It had become awkward for him again. He knew she had seen quite a bit, but it wasn't something he wanted to admit to himself. He decided that he would just tell her everything so they could get past it. He walked over to his closet without saying a word and grabbed his fleshlight. He walked back and presented it to her.

"Here, this is what I was using." he said.

She took it from him and began to examine it. She felt the rigid plastic case, moving her fingers carefully over it until she reached the opening. It felt soft, almost like real skin. It was shaped exactly like a woman's vagina. No wonder her son was having such a great time!

"This is pretty unique," She commented. "How does it compare to the real thing?"

John wasn't sure how to answer that. "I don't really know." He answered. He knew his answer revealed that he was still a virgin.

"Oh!" She replied. "It's OK. There is plenty of time for that." She smiled. She felt sorry for her son. He didn't know what he was missing.

John's mom began to move her fingers closer to the opening of his fake pussy. She slipped her finger into the opening. She wanted to see what her son's reaction would be. His eyes were focused on her motions and as she looked down she could see a slight bulge forming in his shorts.

John noticed his mom looking straight at his now growing erection and quickly adjusted it. He didn't want to bring any more attention to it.

John's mom smirked slightly. "Don't worry sweetie," She said "It's a normal reaction. At least we know it works." She said with a smile. She felt a slight tingling in her pussy. This was turning her on and she wasn't quite sure why. "You can show me if you want. If you want my opinion?"

John was taken aback by that. Did she really just ask him to show her his penis? He was lost in his mind. The thought of showing another woman his penis aroused and scared him. He had never done it before.

Before he had time to answer his mother had begun to remove the strap across her waist that held her robe in place. With one fell swoop her robe hit the floor and she was fully naked in front of him. Her tits were on full display and he wanted nothing more than to reach out and grab them.

"See!" She said nonchalantly. "Nothing to be ashamed of." She knew this was killing her son and she loved it. She wanted to take this even further. "I showed you mine so now you can show me yours!"

John was still in a daze. He didn't know what to do. Being trapped in his own mind wasn't helping the situation either. Suddenly, he could feel his mom's thumbs clasp the elastic of his shorts. He quickly snapped out of his daze and looked at her, ready to protest, but it was too late. His shorts hit the floor around his ankles. He was fully exposed.

John's mother looked down. She could now see everything clearly. Jutting out of his midsection was by far the smallest penis she had ever seen. It was obvious that her son was fully hard. It was completely straight, with no curve. It look like a little missile ready for launch. His head was almost completely engulfed in foreskin, save for the slit at the tip of his penis.

"Oh my!" She exclaimed, shocked at what she was staring down at. "I didn't realize!"

"Realize what?" John said. Deep down he knew what she was talking about.

"I'm sorry John. It's just a lot smaller than I thought. When I saw it before I just assumed it was at a bad angle, but I guess not." She noticed the defeated look on her sons face, yet his little member was still rock hard. She was surprised at how much she was enjoying this.

His mother's words stung, but he knew them to be true. Yet he was still aroused. Hearing it aloud was a new experience for him. His small penis twitched at her hurtful yet sympathetic words.

"I'm sorry dear. I didn't want to hurt your feelings. I just wanted to be honest."

"It's ok." He replied. He felt his mother was genuine in her apology.

"If it makes you feel any better your dad had a small penis as well." The thought of her ex husbands useless penis made her angry.

John didn't know how to react to that. He hated his father for leaving them and now knowing that he was poorly hung made him feel somewhat good, even though he didn't have anything to be proud of himself.

"Do you mind if I ask you a question?" She continued.

"Sure." He replied hesitantly. He didn't know where she was going with this.

"How big is it?" She had wanted to know since she had seen it. It looked much smaller than her ex husbands and he didn't have much to begin with.

John didn't know what to reply. He had never taken the time to do so. He knew he was small and that's all the confirmation he needed.

"I'm dont know." He replied. "I never measured before."

"Really?" She replied, surprised by his response. She thought that all men measured their dicks. She had measured his father's on several occasions, just so she knew how small it was. At 4 inches she had always known he had a useless dick to match his personality

"Hold on." She said as she turned and walked out if the room at a brisk pace. All John could do was stand there and wait.

After waiting for what seemed like an eternity, his mother finally walked back into the room. He had begun to go soft, but that changed as he noticed the bounce of her tits as she walked towards him with a purpose. John was lost in the sight of his mothers beautiful breasts, he failed to notice the giant smile on her face and the object she was holding. When he finally began to focus on the object he realized what was about to happen. She was holding a ruler.

"Here." She said, presenting the ruler in front of him. "This should tell us."

John was mortified. He didn't know what to do. He didn't need his mother knowing how small he really was. He needed to find a way out of this, but he didn't know how. He was about to say something when is mother squatted down in front of him and placed the ruler over his fully erect member.

"Let's see." She said. John's mother was enjoying this. She was wet and she didn't care. She adjusted the ruler over his penis. She had done this before with his father but never really enjoyed it. This however, was much different.

"Oh my!" She exclaimed, concern filling her voice. "Are you fully hard?" She said, knowing full well that he was. Should couldn't believe how small it was.

All John could do was nod his head.

"I'm sorry sweetie. You have a very small penis. It's only 3 and 1/4 inches."

It was official. It was undeniable. It was truth. They both knew how small his penis was. He should have been devastated, but he was too aroused to care.

John's mom continued to stare at his genitals in silence, inspecting them carefully, without touching them. Finally, after thirty seconds she spoke "You have little testicles as well sweetie."

It was bad enough his mother knew his cock was small, but now his balls! He wanted to tell her to leave, but before he could he felt her fingertips grasp his balls.

"Definitely small." she started. "Your dad had bigger balls than you as well!" She continued to feel his balls, rubbing her fingers all over them, grabbing each one and rolling it between her fingertips. He definitely had little raisins between his legs. At least she knew they worked and the damage they could do. She noticed John's facial expressions. He was enjoying this, despite his apprehensions.

"Are you OK?" She said, trying to draw his attention back from his fantasy. "It doesn't hurt when I touch them, does it?"

"No." He replied. He could barely speak. It felt amazing to him. She began using her full hand to caress his testicles, using a bit more force. His mothers face was level with his minuscule member. Her hot breath made him twitch with pleasure.

John's mom noticed this and moved her face closer to his penis. It was really short. She would be able to take his entire penis into her mouth without any effort. Sadly he would never be able to tickle the back of her throat with his little dick. She wondered if she should take it that far. It wasn't her mind that was controlling her anymore.

As she continued to play with his testicles, John noticed his mother staring intently at his penis. She had never seen one that small, so it was only normal for her to be curious.