Uncharted Territory

It was a day like any other when Matt was annoyingly woken up by his alarm. He hit the off button and sat up in his bed rubbing the sleep from his eyes. “Damn, it had to be today didn’t it?” It was Monday morning and it was Matt’s first day at a new school. Like every other 14 year old boy Matt hated starting at a new school, everyone’s eyes on you like a weirdo as you walk down the school corridor because you are the new kid and of course the sordid business of making new friends. They had moved to a new town because Matt’s dad had been sent there for a work project which would span the duration of four years as they were constructing multiple huge buildings. Now making friends wouldn’t be all that difficult if it weren’t for the fact that Matt was extremely shy and had no guts to approach anyone he didn’t already know. He wasn’t a bad looking kid, average looks but he was very thin and weak looking so that didn’t build confidence either.

As Matt sat there dreading this horrid day that was inevitable his thoughts came crashing back down to reality by the sound of his mother’s voice calling for him from the kitchen downstairs. “Matt your breakfast is getting cold, get a move on or you will be late on your first day.” Giving out a huge sigh he rolled out of bed and made his way to the bathroom where he took a shower and went through his usual morning routine in getting ready for school. He made his way down stairs and sat down at the breakfast table across from his dad who was in his usual spot reading the morning paper and sipping his coffee. “Morning champ, you ready for your big day? You have to make a good impression on your first day you know.” James (Matt’s father) said without even looking up from the paper. Matt just let out a depressive sigh and James knew he wasn’t in the least bit excited. “I’ll tell you what son, seeing as this is your first day and all, I’ll give you a ride to school so you don’t have to endure all the eyes burning holes into the back of your head on the bus.” James said to his son trying to make the situation a tad bit better than it was going right now. “Thanks dad, although I’ll get those same eyes on me the whole day at school at least I can avoid it for a few minutes.” Matt said in a tone of voice that gave the impression of slight relief. As he sat and stared down at the table his mom was standing at the kitchen counter fixing a plate for him. “Hear honey, thought I’d make your favourite pancakes for breakfast to get your day started off good and proper.” She said as she walked over to him and placed the plate in front of him. For a few seconds he just stared at the plate as if he wasn’t going to touch it and then suddenly just began wolfing down the pancakes. His mom looked at him in amazement as from her point of view he appeared to be skipping the chewing part and just swallowing everything whole which wasn’t the case but it sure looked that way.

Once breakfast was done James stood up and grabbed his car keys and headed for the door. “Come on son, we got to get moving if we are both going to be on time.” Matt just gave a nod and stood up, grabbing his bag and walked out the front door ahead of his dad. As they approached the car they heard Matt’s mom walking up behind them. “I’m coming too, I want to see my little boy off on his first day.” She said with a beaming smile which was quickly wiped from her face. “Oh come on Sally, you can’t keep babying the boy if you ever expect him to man up. Besides with all my work files in the car there is only room for one passenger.” James said to his wife. She responded in a disappointed voice but seemed to be trying to figure something out as she moved her head trying to see inside the car. “Well it doesn’t look that crowded, but if you insist then I’ll just have to sit on Matty until you drop him off and then you can drop me off at the mall on your way to work. I do need to get a feel of this town.” “Ok fair point I suppose, it is only 20 minutes to the school, you don’t mind, do you Matt?” James asked his son who was staring into the distance. Sensing he didn’t have much of a choice in the matter he just nodded and got in the backseat as that was the only available seat. As the rest of them got into the car they quickly noticed that James couldn’t use his rear view mirror as there were boxes obstructing his view. “Well I guess we better be off then.” James said as he put the car into reverse gear and pulled out of the driveway. As the car picked up speed Matt felt something and he instantly knew he was in trouble. Sally was wearing a very tight pants made out of thin material that wrapped around her body like a second skin. Now Sally is not a model type woman but she is fairly attractive, with beautiful big brown eyes, long flowing blonde hair, full strawberry red lips exaggerated even more by the lipgloss she wears and a typical ‘mom body’ which is a bit on the chubby side but could still be considered sexy due to the fact that she has firm 36D breasts and a wide round ass that still defies gravity. Although it is clear to see she has a mother figure she is still fresh faced and has flawless milky skin allowing her to easily pass for a 34 year old although being 40 years of age.
Matt felt her bum press into him as the car speed up and his teenage, hormone controlled mind couldn’t help but notice how soft and warm her bum was. He tried as hard as he could to ignore it but his body had other plans as he felt blood rush from all over his body into his dick which was quickly coming to life. Sally felt something but though it was a measuring ruler she unknowingly sat on and lifted herself slightly and sat back down.

To Matt’s horror this caused his cock to shift and find its resting place right between her meaty ass cheeks. The minute Sally let her full body weight rest she realised what she was sitting on being in the lap of a teenage boy and the shock hit her instantly. Being the adult in this situation she thought nothing of it as she knew what boys are like while they are going through puberty and just shrugged it off as nothing serious. She calmed herself and just continued as if nothing happened but that plan didn’t go so well as she felt his cock twitch every few minutes and was surprised at how forceful the twitches were. The situation took a turn for the worse when they hit a patch of speed bumps at an elementary school crossing and the car had to slow down and speed up rapidly every few seconds which caused Sally’s ass to slide back and forth in Matt’s lap basically giving him an unintended lap dance. In an instant the blood drained from her face as she heard Matt give out a quiet sigh and felt his cock spasm and then felt her bum being warmed by an unmistakable liquid. She sat there not wanting to move due to the fact that she hadn’t a clue of what to do next.

Luckily the journey was over in just a few minutes and they arrived at the school. Sally opened the door and stood up to let her son out, she instantly thanked her lucky stars she had decided to wear black pants that day as a wet patch would be hard to see. She looked over at Matt and noticed he too had worn black pants and a wave of relief washed over her. They walked around the car and Sally and James said their goodbyes to their son as he walked away and vanished into the crowd of teens. The couple returned to the car and were on their way.

While in class Matt thought back to what had just happened. It was the first time he had ever had that kind of experience with a female and was mortified that it was his own mother. He wondered what she thought of him. “She must think I’m some kind of freak pervert shooting my load all over my own mom’s ass.” He felt a piece of his soul die as that thought consumed him but he snapped out of it when he felt his cell phone vibrate signalling he had received a text message. He didn’t think much of it and waited until the lesson ended and read it as soon as he could. It was from his mother:
“Hi honey, I hope you are having a great first day, and I hope you have made some new friends. By the way I know what happened this morning in the car.”

He felt his heart stop and didn’t know how to reply so he just replied the best way he could:
“Mom I am so sorry! You must think I’m the worst son on earth, I really didn’t mean to do that to you.”
Before he could think his phone vibrated again with a new massage:
“Aww its ok sweetheart, it’s really not that bad. We will talk about it later. love you”
This last message blew his mind to bits. He was now more confused than ever and the whole day he went about his classes numb to everything and everyone around him. “What did she mean it wasn’t that bad? I came on her ass and all she said was love you, talk later.” He thought to himself as confused as a virgin in a brothel.

Finally the day came to an end and before he could reach the bus he saw his mom standing in the car park, she had been home and returned in her car. “Hey hun, just thought I’d pick you up from school.” Matt was confused as he thought he was in trouble for what had happened but he wasn’t quite sure because she was all smiles with him. They got in the car and were on their way home. “So how was your day? Mine was great!” She asked as if nothing was wrong. “It was ok, nothing special.” He replied staring at her face trying to read her mood and then he glanced down and noticed she was still wearing the same pants even though she had been home and could’ve changed it. “About this morning…” Sally began and Matt swallowed hard thinking to himself “uh oh. Here it comes.” She continued speaking. “Well I know you are a teenager now and your body is changing, it just slipped my mind. I would’ve never sat in your lap wearing this kind of pants if I had remembered.” She said to him, smiling as she concentrated on the road. “So you’re not mad at me?” He asked treading lightly. “Of course not, I know you had no control over it. Besides I said it before, it wasn’t that bad. Was nice and warm.” She said making a joke of it and playfully winked at him. They pulled up to the house and entered, setting their bags and stuff down in the kitchen. “That’s a lot of bags for just checking out the town.” Matt said in joking tone to his mother.