Mom is Back in Business

All the characters in this story are 18 or older.

The story is a work of fiction.

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The light piercing through the blinds awoke Jackson at quarter after six in the morning. The second his eye lids parted he let out a massive groan. He had at least another half an hour before he had to get up, and he was hoping to savor every moment of sleep before he had to face the day. It was the first day of his last year in high-school which already felt like a process that would never end.

Compounding that was the fact that he was older than most of his peers; the result of being held back a year during the more turmoil filled period of his childhood. The extra year age difference between him and his classmates had never bothered him up until this point but for some reason with his anxiousness to be done and free from the chains of his education institutional growing it was something he thought about often now.

Jacks begrudgingly made his way to the bathroom and standing over the sink splashed water onto his face hoping that the shock in temperature would wake him up. He had no such luck. Back to his room he went to throw on some clothes. September in the northeast still felt like August and it would probably be weeks before the weather began to shift into Autumn, so basketball shorts and a tee was the outfit for today. Finally, he made his way out of the room and out to the kitchen. His mother, Heather, and him lived in a rancher.

After his parents' messy divorce Jackson and Heather moved around a lot before settling into this house. The time since they moved in was the most stable he had experienced since prior to their separation when he was ten. Heather was already in the kitchen. She sported a grey plush robe which did very little to hide her voluptious figure, but Jackson and her had understandably grown very close without his dad in the picture and she didn't think much of it.

Jackson on the other hand sometimes wished that there a bit more modesty in the house. He wasn't a prude by any means, but he was a young man, and his hormones were on overdrive on a daily basis. The most mundane things could instantly set off a chemical reaction within his eighteen year old body that would leave him in an excited state and this included, occasionally, the way his mother was dressed.

Heather was hard to miss in that way. Like anyone with age she had rounded out in some areas that she was not satisfied with. She would often complain aloud to Jackson that "her ass was too fat" or "that she missed how slim and tight her tummy used to be". On the flip side of the same coin, Heather had always been top heavy and with some of the extra weight gained over time a fair share of that poundage had made its way to her bust line. Some women would see this as a gift and some as a curse. Jacks wasn't sure how his mother felt about it, but he sure knew how his friends felt. They were, in his opinion, overly cheery to see his mother when they came by. They'd often delay departing the house in order to spend a couple extra minutes speaking with Jack's mother. Yes, he knew that his mom was cool and kind to all his friends, but he also knew from some of the comments that they made that their intentions were not always pure.

Luckily, the plush robe his mother was sporting today wasn't as revealing as what she'd sometimes wear around the house. It still did nothing to hide her massive curves within, though. A robe could only do so much. "It's your first day of school, and that's what you're wearing," heather called to Jacks as he took a seat at small kitchen table. She tossed her red long red hair over her shoulder and shot what was a half joking but half menacing look Jack's way.

"Mom, it's hot out, and honestly who cares about the first day of school. I just want to be done already," he retorted as his six foot two frame slumped into his seat. Heather brought over a cup of coffee and a bagel already smeared with cream cheese and placed it in front of her son. "You know Jacks, I get it, I really do, but you should try to savor this time. Before you know it you'll be longing to return to this time," she paused, sighed, and added "trust me on that." Gesturing at the coffee and bagel Jackson smiled shot a "thanks" his mother's way.

"Mom, I believe you, but for now it's just annoying. That's all."

Jackson ran his hand through his short cropped strawberry-blonde hair contemplating the day ahead and finishing his breakfast. "Oh!" Heather said abrupt and loudly suddenly startling Jacks. "Don't forget I have my first massage appointment set up today at four," his mother announced.

"Oh thanks for the reminder. I would have forgotten," Jacks replied. Heather worked as an administrative assistant at a real estate firm in town, but everyone was feeling the effects of inflation, and she had decided to start working as a masseusse out of her home. She used to be a massage therapist when she was younger, and figured this would be the easiest way to pick up some extra cash on the side with little overhead involved. She even had a functional massage table still.

"Yes, now I've given the client direction to come through the back door, and I'll be set up in the den. I'll need privacy during the appointment so the den is off limits, but on the plus side you shouldn't have to see any strangers in the house."

Jackson smiled and looked at his mother with a mouthful of bagel and said "Cool." She loathed when he talked with his mouth full of food, and he knew it, but they both shared a laugh before he was finally off to school and her off to work.

After what felt like an eternity Jacks was finally making his way back home at half past three. How on earth would he keep this up till June? First-world problems he thought to himself. By the time he made it home he could only see his mothers car, so he assumed her client hadn't arrived just yet. Perfect, he thought to himself. He raced to get into the shower, so hopefully he could finish before anyone arrived at the house. He respected his mothers wishes and did not make his way towards the back of the house where she'd be meeting with her client. He swiftly washed in the shower and toweled made his way back to his room. He laid for a while on his bed in his towel before briefly dozing off.

When he woke up at half past four he quickly realized that his young cock had also awoken. He was greeted from his nap by his stiff wood making a tent in his damp towel. As he often did post school he began to surf some of his favorite porn sites searching for additional inspiration and subsequent relief. With his mother administering a massage in the back he was sure he wouldn't be disturbed.

However, the thought of the massage gave him an idea. He wasn't sure why this crossed his mind but he recalled the dog-nanny cam that had been set up in the den. It sat on a bookshelf in the back room and they had used it to keep tabs on their late dog when they had to leave the house for long periods of time. The sound microphone no longer worked, so there was no audio, but he was fairly certain that it was still connected. The camera most likely would still be operational then. He brought up the app on his phone. He had to dig through old apps to find it but sure enough he did. Once the app located the camera via Wi-Fi he clicked the power button on. It was almost a perfect vantage point. The massage table had been stood-up perfectly parallel to the camera.

On the table was a portly man. Even through the low resolution Jacks could make out the mans back hair. Gross, he thought to himself. His mother was not in frame but soon returned. She was wearing just a sports bra which Jacks found odd. It's attire she would wear around the house, but he assumed she would be dressed more modestly for this type of work. She lathered the mans back in oil and continued to work on his back. Something about watching his mother in the skimpy outfit massaging this man excited him, and his cock twitched slightly. Her hands continued to work on the back half of the mans body, but soon she seemed to give the man a pat on the back. Her mouth moved, so she clearly she was saying something to him. By his response it appeared as though she had directed him to turn over. The man complied, but quickly Jackson noticed something odd. The man was sporting a tent under his towel similar to the one Jackson had currently. He could make out through the grainy video what seemed like a giggle-face from his mother, but she didn't seem upset.

Heather lathered her hands in more massage oil and began massaging this man's chest. Jackson doubted by the man's build that he had any muscle there to be massaged, but that was neither here nor there. The entire time Heather worked on his front the tent remained. Heather leaned over to rub the mans hip on the far side and Jackson noticed the man use this opportunity. The strangers hand swiftly made it's way to Heather's sports bra where he quickly cupped one of her giant breast. Jacksons pulse raced.

Should he interrupt? Was his mother going to need help? His fist subconsciously clenched while his hard-on oddly remained intact.

Jackson found himself cursing the fact that there was no audio. His mother's body language seemed to change, but it was so hard to make out through the grainy video quality. Heather ran her hand through her red hair flipping it over her shoulder and then her hand quickly removed the towel covering the client's hardened member. Her face seemed filled with shock and awe as the man's penis became exposed. Her hand gestured to his cock standing stiff in the air while the man continued to fondle her large breast through her sports bra. There appeared to be some sort of back and forth. Heather briefly disappeared and then reappeared just as quickly with the gentlemen's pants.

Good, Jackson thought to himself. She was ending the massage and telling him to cover up, but that was not the case. The man took his trousers from her while she stood there waiting. As she waited she appeared to begin to massage her own breasts through the straining sports bra. The man took something from his pocket. It appeared to be a wallet. This was soon confirmed as he withdrew cash and handed it over to Heather. Heather took the money and placed it on the near by table, a coffee table that had been moved out of the way to fit the massage table. As soon as she set it down she turned back to the man, gave a coy smile, and lifted the sports bra over her head. Her big round tits fell out immediately.

Jackson was in disbelief, but any anxiousness or anger he felt quickly dissipated and was replaced with arousal on a level even the young hormonal Jackson had never felt before. He watched as his mother's bountiful mammaries that once provided him nourishment became completely exposed to and sexualized by this man. Her areolas were large in diameter which was no surprise given the tremendous proportion of her breasts. For all his mothers complaining about her body it was astounding how much lift there still was to her incredibly large pair. Most women would have killed for the gifts she had, Jackson thought.

She leaned over and took some more massage lotion in her hand. As she leaned over the client leaned up towards her and took one of her breasts in her mouth. He was suckling at her nipple. Jackson could make out the face that Heather was making and it appeared to be pleasurable for her. He wondered if she was really enjoying this, or was this a simple business transaction, or perhaps a bit of both. Her now oiled hand moved to the mans stiff penis. Her hand delicately wrapped itself around him and began slowly stroking. Her motion was simple at first. She took jerked him up and down the length slowly.

As Jackson watched he found himself almost unconsciously start stroking his own hard cock which was throbbing so badly it nearly hurt. He looked down at himself and couldn't recall a time he had ever been this engorged. His bright red head glistened with precum and began to stroke himself quicker.

The man on the video clearly became more and more excited. Heather's hands began to twist as she stroked his cock applying extra emphasis on the upswing as the palm of her hand made contact with the man's tip. He squirmed on the massage table and hungrily put as much breast in his mouth as he could manage. The man clearly couldn't withhold his excitement any longer and his legs began to buck. Jackson could see his mother saying something to the man, but soon the man began to expel cum with great force that shot into the air and on to his belly. Jackson could feel himself on the verge and watched as his mother used the man's ejaculant as additional lubricant to stroke the last bit of cum out of the man's now weakened cock, and with that Jackson shot his own load all over the floor of his room. Jackson had nearly cum in unison with the man who was just feet away in a separate part of the house.

The rest was mundane by comparison. Jackson watched as his mother used a towel to clean the man. When it was all said and done the man disappeared out of frame and Jacks soon heard the back door close behind him. Jackson fell backwards onto his bed nearly out of breath. He stared wide eyed at the ceiling wondering to himself. Was this what his mom intended? Are these the sort of massages his mother used to give when she referenced being a massage therapist in the past? Did she enjoy it or was this just about the money the man clearly forked over.

He was operating with way too little information, but either way his perspective of his mother was changed. Additionally, he felt the guilt his mother being the inspiration for one of the most intense orgasms he had ever experienced. Jackson soon fell asleep again, but was awoken by his mother's voice. "Honey, its nearly dinner time," she called behind his bedroom door.

Jackson soon made his way back to the kitchen where his mother had already plated their dinner which consisted of roast beef, roasted carrots, and mashed potatoes. This was one of Jackson's favorite meals. His mother appeared to be in great spirits as she beamed a smile at Jackson while taking a seat. "Well? How was the first day? Don't keep me in suspense," she teased.

"It was uneventful," Jacks lied to his mother. Well, technically school WAS uneventful, but his late-afternoon certainly wasn't. He paused briefly. "How was your first appointment?" he asked after a moment of silence.

Heather smiled and Jackson noticed her playing with hair twisting it around her finger. "It went well I think. It's kind of like riding a bike."

"That's good mom. You know, if you're going to be doing the massage therapy regularly now I may have use for your services."

Jackson wasn't sure if this was the right path to explore, but instinctively the words left his mouth. His mother looked briefly concerned. "Oh no baby. Are you sore? Did you hurt something?" she asked sincerely.

"Now that you mention it my back has kind of been bothering me. I think I may have pulled a muscle playing with the guys last week."

"Well, you let me know baby. If you're still in pain and think you need the muscle rubbed out we could certainly manage that," she said beaming a smile at Jackson as she took another bite of her food. The rest of the dinner was like any other night, really. However, Jackson was lost in thought. He viewed his mother differently now and couldn't get the images from earlier out of his head. He found himself glancing at her chest, and tried to avoid his mother noticing.

They watched some shows together before Jackson returned to his room where he spent a few hours playing games with his friends online, but preoccupied in his mind still. He signed off earlier than most nights and made his way to his bed. He brought the dog-nanny app back up and replayed the footage from earlier as he stroked himself to the sensual moving images of his mother and after an orgasm nearly as explosive as the one he experienced earlier in the day, fell fast asleep.

Jackson awoke with now found energy. No, he wasn't excited to go back to school, but the night before his mother had detailed her schedule for the rest of the week, specifically as it related to the massage therapy. Heather had a full slate. She had one appointment each day Monday through Friday. Jackson also found this curious. He didn't know much about that industry, but with his mother having taken a nearly two decade hiatus since the last time she was a massage therapist, what were the odds that she would have a full slate of clients this quickly again? Regardless, he wanted to power through his school day so he could tune in and see if this session would be like yesterdays.

The school day dragged on and on. History, which was the last class of the day, felt like an actual eternity as the teacher droned on about the Byzantine Empire. Who cared? Not Jackson. He had other things on his mind. Specifically, he kept replaying the image in his head of his mother's reaction when she undraped the clients cock from yesterday.

Finally the bell dinged. Jackson avoided his buddies and was out the door as fast as he could so he could get home. He'd follow the same schedule as yesterday. He got home even earlier this time around. He went and cleaned himself in the shower getting excited about the impending possibility that he got to see his mother administer similar services today. Once the clock hit four he was eagerly tuned in to the dog-nanny app to see the show.

Much to his chagrin the show started late, but at five past four someone came into frame. It was another male. From what Jacks could tell he was in much superior shape to the man from yesterday and significantly younger. He could make out the mans muscular body in spite of the poor picture quality. His mother also seemed even more enthusiastic in her massage duties, but of course, perhaps this was in Jackson's mind. It was so hard to tell through the video anyway. Everything seemed pretty normal for the first fifteen minutes or so, but then his mother made her way to the top of the table.

The man was still laying on his stomach but she stretched out over his head to reach his back which Jackson found odd. It was clearly not the optimal position for the area she was trying to massage. Her sports bra containing her large breasts began to graze the mans head.

This must be intentional Jackson thought. His mother was at least playing a part in instigating these activities by teasing these men. Before the man could even turn over she had lifted her sports bra off again exposing her perfect tits. Soon the man was on his knees on the table kissing her neck and making his way to her nipples while she stroked his all too eager cock. Just like yesterday Jackson finished nearly in unison with this man. It was becoming all too clear to Jackson that he wanted to experience what these men were fortunate enough to.

Jackson wasn't sure how he'd make it happen, but this was clearly his sole focus now. After he cleaned himself up Jackson made his way to dinner. It was another good meal filled with more glances at his mother. Both frequency and brazenness increased. He felt differently about his mother. It was more primal now. He wanted her the way these men had had her and more.

At dinner he continued to lay the ground work for what was the best or only plan he had at the moment. He grabbed at his back and continued to complain "Oh mom. I really think I messed up my back bad last week. I may take you up on the offer to rub it out if you can?" he inquired between bites of food.

"Honey, I'd be happy to, but it may have to wait until the weekend. I'm swamped with clients during the evenings this week," she replied with a smile.