The irony in Samantha Milford's name was not lost on her son Jason. He had been born when she was just a young girl of 18 and now at 36, even with a son who was legally an adult, she was still just as stunning as ever. Just as her name implied, she was indeed a MILF. Since he was around 14, Jason had known just how attractive his mother was. Like most boys that age, he was just discovering himself and began seeing women in a whole new way. Naturally, his gorgeous mother became the object of many of his masturbatory fantasies and he was now long past the point of feeling shame due to that fact. Over the years, his affections had blossomed as he found that he got the most pleasure from reading stories online about mothers and sons in sexual relationships. He loved the idea of a mother submitting to her son and soon found that his thoughts whilst pleasuring himself would often return to those of his mother on her knees in front of him.
It was his high school graduation day that he decided he'd had enough fantasizing. His mother had been quite lonely over the course of the previous year, having recently completed a nasty divorce with his father for cheating during the previous Summer. She'd been quite clingy towards Jason since then, but never in quite the way that he'd secretly hoped for. She would treat him like one of her girlfriends usually, venting and complaining to him about his father. The night after Jason's graduation ceremony, she had taken the opportunity to break out an old bottle of wine and poured some for them both to celebrate. By the end of the night, he had barely finished a single glass and his mother had finished off the rest of the bottle. The more she drank, the more she vented to her son. She talked about how she'd put in so much time and effort to make her marriage work and how her ex husband had given that all up for a fling with some young floozy. Then she talked about how she'd gotten so much money in the divorce settlement, saying that it "served him right", then giggling herself into a fit. She was hanging all over him while she spoke and her son's head was filled with impure thoughts.
"I'm so proud of you, sweetie!" she'd declared, leaning in and tenderly kissing her newly graduated son on the cheek before drunkenly passing out on the couch.
He sat there watching her for the next fifteen minutes or so, visually taking in all of her petite figure. He watched her large, heaving breasts move up and down as she breathed. It was as if they were begging to be let out of her tight blouse that was most certainly a size or two too small for her bust, but only made her moderately slim waist look even slimmer . He admired her soft, thick thighs and how they looked pressing out against her skirt, continuing upwards before ending where her white cotton panties began. He observed how her dark brown hair had been sprawled across the couch and dipped down into the top of her blouse, flowing down between her large creamy breasts that squeezed together, pouring out of the top of her clothing. And he loved the way her thick, full, and beautiful lips looked with her dark red lipstick on.
Maybe it was just his friend in his pants thinking for him, but staring at her stretched out on the couch that night, he knew he was done just fantasizing about his mother. But he didn't want her like this. For him to take advantage of his drunken mother would be shameful and would damage their relationship beyond all repair. No, he wanted his mother to be a willing participant. If it was possible, he wanted her to initiate. It was then and there, looking down at this sexy woman stretched out before him that he made himself a promise; before a year was up, those beautiful red lips would be around his cock.
Since his father had been kicked out, his mother had started masturbating in her bedroom next to Jason's nearly every night. However, she didn't know that the now defunct air vent between their bedrooms would allow him to hear her gasps and moans of pleasure quite clearly from the comfort of his own bed. The vent was a remnant from before the home was remodeled, years before they'd bought the home 12 years prior. Nearly every night, Samantha would go to her tall oak dresser, open the top drawer, retrieve her large pink vibrating dildo and pleasure herself well into the night. But she didn't know that her son would silently open the air vent from his side, where he could then easily listen to her cries of passion whilst he too pleasured himself. It was a great system that he had worked out for himself, but after graduation night it was simply not enough.
The first part of Jason's plan was simple. He visited the mall the next day to buy some sexy but subtle cologne. When he got home, his first course of action was to remove the grate from his side of the air vent. Inside, he placed the bottle of cologne in such a way that if it was to spray, it would do so directly up into his mother's room. He attached a long plastic rod to the nozzle in such a way that if he pressed down on one side of the rod, the nozzle would give a spritz of cologne. Then, he placed the grate back onto the vent, making sure that the plastic rod would poke out of the grate just enough that he could press it, but not enough to be noticed unless you were looking for it. That night, Jason waited in his room for his mother to begin her nightly routine. It wasn't long after she'd changed into her nightgown that he heard the squeak of her dresser drawer, followed by the familiar click on and then buzz of her bright pink toy. Oh, if only his mother knew that he'd heard that noise so many times. He wondered what she might think to know that he'd listened to her masturbatory cries so many times. And what's more, he'd joined in with her nearly every time he heard it. But tonight, his first line of business was to wait until she was really into it, then he pressed down on the rod, spraying a small amount of cologne into her room. Not enough to really be noticeable, but enough for her to smell it unconciously, if at all. With that, he quietly got up into his bed and masturbated, thinking of all the wonderful things he was going to do to her when his plan was finished.
His next step was to start spending more alone time with his mother. Now that school was out, he had a lot of free time to kill and he knew that he'd have to spend more time with her if he ever wanted to develop a relationship, let alone to bed her. So that's just what he did. He'd help her fold laundry, he'd help her cook and do dishes, they would sit and play chess or checkers, but most importantly, he'd convinced her that they should have a nightly or semi-nightly movie every night over the Summer.
"We should spend more time together before Summer ends," he'd told her, "I don't know how much we'll see each other if I start college in September or if I get a job."
She'd thought it was a great idea and they'd soon created a rather large queue of movies to watch on Netflix together. So, five or six nights a week, the two would sit down on the couch and watch a film, be it a classic, a sci-fi or one of countless romantic comedies. And as time went on, his mother became very relaxed around him. While they'd started on opposite sides of the couch, soon they were sitting next to one another and sometimes even falling asleep on the other's shoulder before the movie finished.
This led to part three of his plan. While he'd kept spraying the cologne every night while she played with herself, starting to spray more and more as time went on and he still continued to spend time with her, this next step would be equally important. The next step was to initiate touch with her as a regular thing. It started simply enough; he'd touch her shoulder here and there when she'd make a joke or when she would vent about his father but as time went on, he started touching more and more. He'd eventually be able to put his arm around her or hug her whenever it felt appropriate and there was no awkwardness. He'd become closer to his mother than he'd been even as a child. Eventually one day he was helping her fold some laundry when he decided to try pushing the envelope.
"Have you lost some weight recently, mom?" he asked her, knowing full well that she hadn't and didn't need to.
"Oh don't you try to flatter me," she replied, giggling "if you need to borrow some money, you can just ask, you know."
"No, I'm serious. You look beautiful today."
"Now you're just being silly."
"You're right, mom. I am. You look beautiful every day." he rebutted, taking a chance and poking her tummy lightly, wiggling his finger.
"Stop!" she laughed, shifting away, "You know I'm ticklish!"
"Oh are you, now?" he smirked, continuing to tickle her with his finger, secretly proud that things were going just as he'd hoped.
He continued tickling her, eventually with both hands and all five fingers. It was just a little horseplay. No ulterior motives. But it set a precedent that Jason new would pave the way for things to come. He had broken the physical contact barrier.
After that, he'd initiate impromptu tickle fights with his mother every so often for the fun of it. And she would even try to tickle him back. It was everything he could ask for and more. Not only was he getting permission to touch her, but now she was actively trying to touch him. The two had become much more comfortable with one another, physically, and he could not have dreamed things would progress so quickly. September came and went and Jason had decided to take a year-long break from school to "recharge his batteries" (or so he told his mother) and he would attend college in the Fall of next year. His real reason for not starting that year was to have more time to devote to the seduction of his mother that he was convinced was going completely according to plan. He continued to compliment her regularly, as well. He knew that would be another key to making her see him as more than a son. They continued their semi-nightly movie watching and soon it had become something they did routinely, without even thinking about it. Eventually, due to his mother becoming more comfortable with physical contact and with slow drop in temperature now that Summer was over, she even began snuggling up next to him on the couch, where they would share a blanket. That was when Jason had decided to push the cologne portion of the plan a little further.
He'd entered her room one day while she was out shopping and opened her top drawer where she kept her sexual toy. He looked in at the bright pink vibrating dildo he'd envied for so long. But this time, he knew that one day it would be him thrusting in and out of her. He leaned over the drawer and he sprayed a spritz of the cologne inside. It was a very subtle scent, but still slightly noticeable. Now, not only would she smell the cologne while she masturbated, but also from the very device that she used to do so. Theoretically, the scent of the cologne alone would soon be enough to make his mother extremely horny. Learning about Pavlov in 10th grade had finally come in handy.
