The Cougar Chronicles - Janet
by Aramis
Copyright© 2024 by Aramis
Erotica Sex Story: A middle-aged woman gets a surprise when she seduces the teenaged boy next door.
Caution: This Erotica Sex Story contains strong sexual content, including mt/Fa Consensual Heterosexual Fiction Cream Pie Oral Sex .
(Author’s note: This story is a sequel to “Discovering Mom’s Weakness,” so if you haven’t read that story yet I strongly suggest you do so as the events in this story will make more sense.)
It was Saturday morning, and as usual the seventeen-year-old son of Janet’s next-door neighbors, Ron and Glenda, was outside cutting the grass while his father was out playing golf or some other such silly thing. Ron Junior was a strapping young man, tall and lean, with dark hair, a chiseled face, and a slightly muscular body with the tightest little ass she’d ever seen in all her 50 years, and Janet thought that if she didn’t fuck him soon she’d go out of her mind. She watched him through the blinds of her window, watching his tight ass flex as he walked up and down the yard pushing the mower. Today he was wearing a light gray sleeveless t-shirt and a dark blue pair of gym shorts, both of which were soaked with sweat. He finished cutting the grass and put the mower back into the shed next to the house, then walked inside and out of sight.
“One of these days, dear boy, one of these days,” she mused to herself, turning away from her window when Ron went inside his house.
Her chance came about a week later when the mailman accidentally put a piece of mail addressed to her in the wrong mailbox, putting it in Ron and Janet’s mailbox instead of hers. She was just getting ready to go out into her back yard and get some sun when there was a knock on her door. She was in her bikini so she grabbed the beach robe she usually wore with her bikini and put it on, covering up the skimpy white bikini she was wearing. When she answered the door she broke out into a big grin when she saw Ron Junior standing there, wearing his usual Saturday attire of a sleeveless t-shirt (red this time) and the same dark blue gym shorts as the week before. She could tell he hadn’t started cutting the grass yet because he wasn’t sweating, but she wouldn’t have minded if he had been.
“Well, hello, Ron, what brings you to my door?” she said, smiling like the cat who was about to eat the canary.
“Hi, Mrs. Smithers. The mailman got some of your mail mixed in with ours,” he said, holding out the misdelivered envelope.
“Now, Ron, how many times have I told you to call me Janet?” she said, taking the letter from him, still smiling.
’Still has the hots for me, I see,’ Ron thought to himself, recognizing right away that she was flirting with him as usual. ’But you know, she’s really not all that bad looking when you get right down to it. She’s actually kinda sexy, in an older woman kind of way,’ he thought as he quickly looked her up and down.
Janet was tall, only a few inches shorter than Ron was, and it was obvious from her figure that she’d never had any children. She was slim and trim without any of the soft padding that you’d find on the bodies of most women her age, with a long, shapely pair of legs that ended in a firm, well-rounded butt. She wasn’t big busted like his mom was, but she had a nice, firm pair of breasts that he would have guessed was a ‘C’ cup at least. She had short platinum blond hair that obviously came out of a bottle, and wore it in the old ‘pageboy’ style which he thought actually looked pretty good on her. She had a pair of sparkling blue eyes and a pert nose, centered over a pair of soft, full lips.
“Okay, Janet, if that’s what you want,” he said, returning her smile.
“Oh, that’s not all I want, dear boy!” she said, her smile turning into a grin as she reached out and grabbed him by the front of his shirt, pulling him into the house. She closed the door behind him and turned to face him, putting both hands on his chest and pushing him back up against the wall.
“Do you have any idea how long I’ve waited for the chance to do this?” she said, her voice a husky whisper as she looked up at him, leaning up against him with her hands on his chest.
“The chance to do what?” he asked innocently. He knew exactly what she was talking about; he just wanted to have a little fun with her before he turned the tables on her.
“The chance to fuck you, that’s what, dear boy!” she said, sliding a hand down and grabbing his cock through his shorts as she slid her other hand up and around to the back of his neck. She pulled his face down to hers and kissed him, hard and deep, sliding her tongue into his mouth to find his own. She pressed her body up against his as she squeezed his cock in her hand, feeling it beginning to grow bigger and harder under her touch. Ron reached around and grabbed her ass with both hands, squeezing it hard and pulling her close to him as he returned her kiss.
’Oh, my! The behemoth awakes!’ she thought to herself as he squeezed her ass hard, his cock growing bigger and harder by the second. He was a good kisser, and she felt her nipples getting hard and her pussy getting wet as they kissed. She gripped his cock harder, pulling on it through his shorts, and was taken totally by surprise when Ron suddenly spun her around and pushed her back up against the wall where she had just pushed him.
“OH!” she gasped as he pressed his body against hers, sliding one hand up her body to her breast, gripping the firm globe in his hand and squeezing hard as he kissed her again.
’Let’s see if this works on Janet the way it worked on Mom,’ Ron thought to himself, deciding to take the initiative and take control. He squeezed her firm breast hard as he slid his other hand around and down to her pussy, cupping her mound in his hand and feeling the heat emanating from her. She moaned in his mouth as he rubbed her pussy through her bikini bottoms, sliding one hand around to his butt and squeezing it while she kept the other hand on the back of his head.
“MMMMMMM!” she moaned into his mouth as he rubbed her pussy harder, jumping and gasping when he slipped a finger into the crotch of her bikini bottoms and then into her pussy. He was surprised to find that she was already very wet, his finger sliding in easily. She surprised him when she clamped her pussy down onto his finger, squeezing it with her inner muscles.
“You like that, dear boy?” she asked, her voice a breathless whisper as she squeezed his finger harder with her pussy. “Just wait until you feel my pussy squeezing your cock like that!” she said, looking into his eyes and grinning.
“There’s something I want to feel first, though,” he said, returning her smile.
“And what’s tha – OH!” she gasped as he put his hands on her shoulders and pushed her down, forcing her down onto her knees in front of him. She came face to face with the big bulge of his hard cock beneath his shorts, a small wet spot showing where his precum had soaked through both his jock strap and his shorts. She knew what he wanted, so without being told she reached up and grabbed the waistband of his shorts, pulling them and the jock strap down at the same time. His cock sprang out, bouncing in front of her face and almost hitting her on the nose, the tip shiny with precum.
“Ooooo, look at that! A nice, hard cock for me to suck on!” she said, wrapping her hand around the base of his cock and squeezing firmly, pumping it slowly as she looked at it. She opened her mouth and leaned forward, slowly lowering her mouth down around his cock, sticking her tongue out and placing it against the underside of his cock as she closed her lips around it, sucking firmly. She slid her mouth up the head of his cock and then did it again, opening her mouth and dropping it slowly down onto his cock, sticking her tongue out and placing it on the underside as she closed her mouth around it again. She did this several times, the technique something completely new to Ron who watched in amazement.
’Holy shit, she’s good!’ he thought to himself as Janet sucked his cock for real now, keeping her mouth closed around it as she slid her mouth up and down on his fully erect cock, taking almost all of it in her mouth on each downward stroke. She ran her tongue along the underside as she pulled her mouth up the shaft, sucking hard as she went. Then she reached up and took his balls in her hand, massaging and squeezing them as she slid her mouth up and down on his hard cock.
’Oh my God, he tastes good!’ Janet thought to herself as she sucked Ron’s hard cock. She moaned as she got a squirt of precum on her tongue, loving the salty taste of it. She sucked his cock steadily for several moments which were very enjoyable for both of them, then Ron decided to try and take control once and for all. He reached down and grabbed Janet’s head in his hands and began face-fucking her, moving her head back and forth to slide her mouth up and down on his hard cock.
“MMPH! MMPH! MMPH! HMMPH!” she moaned in time with her mouth being forced up and down on his cock, her hands pressing against the front of his thighs as Ron pushed his cock deeper into her mouth. He looked down and watched, turned on by the sight of his glistening cock sliding in and out of her mouth, a small strand of saliva dripping down from the corner of her mouth. He face-fucked her for a few moments more, then pushed her mouth down onto his cock as far as he could, driving his cock deep into her mouth. Janet gagged a little as the head of his cock hit the back of her throat, but she opened her throat and breathed hard through her nose as she had learned to do a long time ago. This let her take his cock into her throat with no more gagging, something that impressed him. He held her head down on his cock for several moments, then released her head from his grip. She pulled her head back and freed herself from his cock, taking a big, whooping breath of air as she leaned back against the wall behind her.
“Oh, my God, you really know how to get what you want from a girl!” she gasped, looking up at him and grinning, her mouth open as she panted for breath.
“Three guesses what I want next,” he said, looking down at her.
“The same thing I want, I’m betting,” she said, getting to her feet in front of him, standing so close that her breasts were touching his chest. “Your cock in my pussy!” she said, looking him in the eyes as she spoke, a sly grin on her face.
“Correct!” he said, returning her sly grin.
“Then let’s go!” she said, grabbing him by the hand. She led him down the hallway to her bedroom and over to her bed, stopping when she got to the foot of it. She quickly stripped out of her short beach robe and bikini as Ron stripped out of his shirt, shorts, and sneakers. As soon as he was naked she put her hands on his chest and pushed hard, shoving him backwards so that he fell on the bed and landed on his back. She was on him immediately, climbing up on top of him and straddling his hips, her breast swaying a little on her chest, her nipples hard as rocks.
Ron didn’t have time to get a good look as she was moving too fast, but he liked what he saw. Her breasts were firm and round, capped with hard nipples surrounded by small pale pink areolas; her stomach was flat and her pubic mound was shaven smooth, and as she grabbed his cock and pointed it up at her pussy he could see that her outer lips were swollen and glistening with her juices. She rubbed the head of his cock up and down her slit a few times to get it slippery with her juices, then sat down on it hard in one long, firm push.
“AAHHHHHHHHHH!” she sighed, holding her head back with her eyes closed, her mouth hanging open as she sat down on his cock. She took his entire length inside her in one smooth motion, her ass pressing against his balls as she impaled herself on his stiff cock. She lowered here head and opened her eyes to look at him, smiling as she spoke.
“You’ve got a great prick, Ron!” she said as she started riding his cock, sliding her hips back and forth to slide her pussy up and down on his cock. She wasted no time, riding his cock hard and fast, taking it deep inside her with every downstroke of her hips. Ron reached up and grabbed her tits in his hands, squeezing them hard and making her moan. In return she clamped down on his cock with her talented inner muscles, squeezing it hard and making him jump.
“You like that, huh?” she asked, grinning and giggling at him. “You like it when I squeeze your big dick with my pussy like that?” she asked, still riding him and squeezing him again.
“Oh, hell, yes, that’s incredible!” Ron replied. He’d never encountered a woman who could do that before, and it just amazed him.
“That’s how I’m going to milk the cum out of you, dear boy,” she said, leaning forward and looking him in the eyes, her voice going soft and sultry as she continued riding his cock. “I’m going to ride you hard and fast, take your cock deep inside my pussy, and squeeze it hard until you cum. And then I’m going to keep squeezing until I’ve milked every drop out of you, until I’ve milked that dick of yours dry!” she said, smiling as she looked into his eyes. She squeezed his cock hard as she rode him in emphasis to what she had said, making Ron jump again.
“Damn!” he said, grinning up at her as he squeezed her tits hard in return.
“Oh, yes, lover, yes! Squeeze my tits, squeeze them hard!” she said, teasing him as she squeezed his cock with her talented pussy. She rode him hard and fast, squeezing his cock over and over again as hard as she could, more than a little surprised that he hadn’t cum yet. Most men – especially the young, inexperienced ones around Ron’s age – could never last very long once she started squeezing them with her pussy. They always came hard and fast, but not Ron. Ron was taking everything she was able to dish out, impressing her to no end.
What she didn’t know was that Ron was hanging on by the skin of his teeth. He’d been resisting the urge to cum within two minutes of her climbing on top of him and squeezing him with her pussy, and he didn’t know how much longer he was going to be able to hold out. Her pussy was very wet and tight to begin with, but her squeezing him the way she was made it that much harder to hold back. But he was determined to hold out for a little while longer, and he knew that the only way to do this was to take control. So without warning he grabbed Janet and pulled her down on top of him wrapping his arms around her and rolling over on top of her, keeping his cock inside her as he did.
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