Fuck! Jason Black looked at his test score and immediately regretted not studying. Instead he’d spent the last week as he spent most weeks, jacking off to porn at home then walking to school and fantasising about fucking damn near half the girls and most of the teaching staff as well. Jason was a typical horny teenager.
Jason knew that he would be in some deep trouble if his mom ever found out he’d failed another assignment, so naturally, he didn’t plan to tell her. He’d just make sure to study for the next one… maybe.
At the end of class Miss Lee, Jason’s English teacher, asked him to wait behind. Oh this can’t be good Jason thought, but he was relieved at an excuse to remain seated because he still had a huge bulge in his pants, caused by Miss Lee’s decision to show a risqué amount of cleavage today.
Miss Lee was one of Jason’s regular fantasy fucks, in his head it was a regular occurrence that he bent her over her desk and pummelled her tiny pussy, before dumping a load of his thick, hot cum in her perfect little rosebud off an asshole. Several times he had stayed behind for extra tutoring after school in which she would spend the entire of the time they had worshipping his long cock with her mouth.
“…is it Mr Black?”
Jason was brought back to earth by the strict tone of voice Miss Lee was talking to him with and that last part was definitely a question, although only having heard the end of it Jason could no better answer that than those on the Romeo & Juliet paper he had just failed.
“No.” Jason guessed at an answer.
“Then why do you not study for any of the exams, Jason?” Her tone had softened so Jason had obviously guessed correctly.
“I don’t know miss. Romeo and Juliet just doesn’t appeal to me.” He said in a monotone voice. Jason was bored with the same old conversations ‘Why don’t you try harder?’ ‘Did you even study for this test?’ The truth is there were plenty of others in the class who failed assignments from time to time, but it always seemed to be him that was singled out.
“It doesn’t appeal to many teenage boys, or girls for that matter, but they study all the same. Why should you be any different? This sort of thing has happened too often Jason it’s about time I contacted your parents.”
Jason turned a ghostly shade of white. He was screwed and he knew it. Every day his mother asked him about school, how it went, who he’d been hanging out with and how he was doing in lessons and he always told her how well he was doing. A white lie, or so Jason thought but that white lie is about to bite him in the ass.
***
Anna had just got home from a tough day at work. Anna works as a PA in a law firm and they had recently taken on a case with quite a lot of media attention. Her boss Mr Baldwin hates journalists and cameras and all the added pressure that comes with them so has been taking a lot of his frustrations out on her. He usually shouts a lot more when stressed but today he had wrongly accused Anna of making personal calls at work. When he had found out it was a client, he had stormed out without apologising.
Now she was home Anna could relax and forget about work stuff, and her misogynistic asshole of a boss. She kicked off her heels as soon as she walked in the door and decided she should go straight in the bath and treat herself to a nice relaxing soak in the bubbles with some scented candles and maybe even her favourite dildo.
She started the bath and put some music on while she waited, she then headed for her bedroom to get her favourite toy, an eight inch, thick silicone cock which would soon be taking its rightful place in her warm, wet pussy.
As she walked out of her bedroom and back towards the bathroom she passed the body length mirror in the hall and got a naughty idea. Not having had a man for eight years, other than the odd one night stand here and there, Anna hadn’t done a strip tease in a long time. She looked herself up and down. The woman that stared back at her looked to be in her late thirties, even standing barefoot she was quite tall, about 5’8”. She had a pretty face that revealed her Cambodian decent on her mother’s side and big brown eyes that were always full of expression, right now they were full of Anna’s horny, excited anticipation. She wore dark eye make-up that accentuated her sultry look, and a subtle pink lipstick. All of this was framed by her wavy hair which had been dyed light brown.
Anna’s eyes dropped to her body which, although hidden beneath a conservative grey and black dress, Anna could see still looked in good shape despite her advancing years and lack of a workout routine. Anna’s breasts, in particular were forcing the dress to hug her curves in a way which was certainly easy on the eye, if not easy on the material. They were 34 DD’s thanks to an enhancement operation she had a decade earlier to please her then husband. Looking further down Anna’s eyes lingered on her hips which hinted at her big curvy ass, she turned sideways to admire what she considered to be her best feature. Anna’s eyes continued their descent and swept over her strong womanly legs that so well matched her round booty. Finally Anna admired the work of her pedicurist and the French tip nails she had done so perfectly to make her small, cute feet that much sexier.
Anna started gyrating her hips slowly to the rhythm of the music. After several seconds she was so lost in the dancing that she closed her eyes, forgetting she was doing a strip tease. She opened them again and decided to give herself a little spin, she stopped facing away from the mirror and bent at the hips while looking over her shoulder at the dress struggling to contain her curvaceous ass.
The anticipation was starting to get to Anna now, as she felt herself getting wetter and wetter. She decided to hurry things along and reached around the back of the dress to find the zipper. She pulled it down slowly and alternated dropping each shoulder slowly in time to the music so that the dress started to fall away. She grabbed her breasts briefly to stop the dress from falling any further but soon released them after giving each a shake. Anna, cheekily, had neglected to wear a bra to work today and so her big tits were revealed though they didn’t drop an inch.
The dress had got stuck on Anna’s curvaceous hips and she grinned at the sexy sight, she turned again and looked over her shoulder as she slowly and deliberately lowered the dress over her ass to reveal a lacy black thong that looked great against her naturally tanned skin. She let the dress fall completely now and wiggled her ass before turning around to admire her reflection from the front. Anna put her hands above her head and continued to sway to the music while wearing nothing but a lacy black thong. Her hands dropped to her head and messed her hair as she dropped into a squat while turning her knees out. She could see the outline of her pussy through the material and also, she thought, a hint of moisture from her rapidly dampening pussy. Standing tall again, Anna put her thumbs under the waistline of her thong and dropped one side slightly before returning it. She did the same on the other side only this time she went far enough that a bit of her pubic hair was revealed.
The front door was opened and slammed shut from downstairs. With a start Anna let go of her panties and reached down to grab the dildo she had left on the landing. She then darted past the stairs and into the safety of the bathroom, just as she her heard her son Jason make his way upstairs.
Anna sighed with relief and realised she had positively soaked her thong at the thought of being caught. Some things never changed. In her late teens Anna discovered the thrill of performing sexual acts in a public place with the risk of being seen and apparently she hadn’t grown out of her exhibitionist fetishes.
She removed her drenched thong and stepped towards the bath which was now just about full. Turning off the taps she got in carrying her favourite sex toy and immediately slipped the silicone toy inside her hot slit. She teased herself with slow, shallow strokes for several seconds before really getting to work slamming it in to its maximum depth with speed. Within minutes she was close and with her free hand started strumming her clit, which elicited an involuntary moan to escape her luscious lips. Anna was too far along to care and anyway the thought of Jason hearing only turned her on more. This caused the image of her teenage son to swim to the forefront of her mind as she rode her toy to orgasm.
***
Jason entered the house, in a terrible mood and slammed the door. He had been kept in detention by Miss Lee for an hour and so didn’t get the chance to hang out at his friend’s house as he usually would for a couple of hours after school. After the detention, which seemed to drag on for ever despite his imagination keeping him somewhat entertained with images of Miss Lee in various states of undress, Jason came straight home and so was earlier than usual.
Jason heard music as he came in and assumed his mother was in the bath until he heard the banging of footsteps. He looked immediately up the stairs towards the source of the noise just in time to see his mother’s thong covered ass disappear into the bathroom.
Jason’s boner was back instantaneously, his mother being one of his other fantasy girls. Jason didn’t worry about the taboo of finding his own mother attractive, she was a beautiful woman, all of his friends told him so, though not always using words as polite as beautiful, and anyway he’d heard enough about Freudian psychology to believe that most teenagers will have a crush on their mother to some extent.
He ran up the stairs with a grin and put his ear to the bathroom door on his left, he didn’t hear anything out of the ordinary so turned right and headed towards his own room at the end of the hall. However Jason didn’t reach his own room he instead slipped into his mother’s, his curiosity getting the best of him, and walked straight to her underwear drawer where he knew she kept her toys. Jason’s grin got wider when he realised the silicone clear dildo was gone and went back to the bathroom to see if he could hear his mother playing with herself above the music.
He had his ear to the door and cock in hand, Jason realised how awkward a position he would be in if the door suddenly opened but that only made him harder. He started jerking his cock slowly while listening intently for any sign of his mother’s pleasure. For the first couple of minutes he heard nothing and then, just as he was giving up hope, he heard a high gasp followed by a low moan. Jason’s cock throbbed in his hand. There was a short pause then again he heard the moan and what he guessed was the noise of his mother thrashing in the water. The moaning and thrashing continued until it reached a crescendo with a really high pitched squeal. Jason was about to burst and so abandoned his post, sprinted to his room and blew his load into a dirty t-shirt, while fantasising about his mom squealing as he impaled her on his cock.
***
Friday morning and Anna enters her sons room to wake him for school, not for the first time she sees several items of clothing that had obviously been used as clean up for his seed. Anna didn’t mind that Jason masturbated, it was completely normal for a guy his age, she just wished he’d be a little more discreet about it.
She wondered how he’d like it if she were to leave her cum soaked panties lying around the house. He’d probably steal them and return here to add his own deposit to them she surmised. Anna had noticed the way Jason looked at her and also suspected he had stolen some of her sexier bras and panties, though she couldn’t prove it. She didn’t mind the lustful looks her son gave her, in fact she was a little flattered mainly due to the lack of any other men in her life to ogle her.
Anna nudged Jason and told him he needed to wake up to get ready for school.
Ugh, school! Jason thought, and then another thought hit him; Miss Lee will be calling his mom today to tell her about his failed assignments. He knew he should give her a heads up but dreaded the conversation so decided he’d just leave it.
Jason reluctantly got out of bed, showered ate the cereal his mom made for his breakfast and then left, grabbing a banana on his way out.
Anna headed out soon after Jason and drove to work. She arrived five minutes early and decided to make a coffee for herself before she went to sit at her desk. She kicked off her shoes as she usually did, and wiggled her stocking covered toes before taking the first sip of her coffee. No sooner had she done this, than Mr Baldwin, her boss, came over to start bellowing instructions. Anna despised Mr Baldwin’s highly demanding, unappreciative nature and had even started looking for another job. But for now she smiled politely, replied “Yes Sir” to all of his commands. Anna frowned as Mr Baldwin left her with a week’s worth of work that he expected done by the end of the day. It looks like she would be staying late again and may even need to come in on the weekend.
At one o’clock Anna went for her dinner break and visited the small Italian restaurant across the street as always. On arrival she was greeted by the one and only waiter and he took her to her usual table, she thanked him, before he left to fetch the salad she always ordered. Niccolo, the owner and head chef returned with her salad and a big smile, he even sat to join her, offering her a glass of wine on the house which she rejected in favour of water.
Anna admired and envied Niccolo, as he was the happiest person she knew, whether his small restaurant had a line of people that stretched round the corner waiting to get in or was empty as it was now. Regardless of what was happening in his own life he always had a smile for his customers and today his small talk was a welcome distraction from her job.
Midway through her meal Anna’s phone rang, she excused herself to Niccolo, who retired to the kitchen to give her privacy, before answering it, not recognising the number.
“Hello, Anna Black.” She said, not having dropped the professional tone she used only while at work.
“Hi, Miss Black, I work at your son Jason’s school as his English teacher I was just wondering if you have a minute to talk.”
“Sure.” Anna replied confused.
“My name is Miss Lee and as I said I am your son Jason’s English teacher. I am calling to inform you that his progress of late has been less than encouraging as he has failed the last three assignments.”
“Okay. He never said anything about struggling.” Anna replied, a little hurt that Jason had not felt able to tell her about it himself.
“Well that’s just it Miss Black, I have a number of students that are struggling with the work, however I don’t believe your son is among them. I just don’t think he’s not trying. He spends most of the time in lesson daydreaming and I doubt he even bothered to read Romeo and Juliet before turning in his last assignment. As his mother I thought maybe you’d be more adept at finding the causes of Jason’s distraction and could maybe aid him to refocus.”
“Absolutely, I’ll have a word with him.”
“Thank you, Miss Black, have a good day.”
“You too.”
Anna was distracted when she returned to work and so worked slower than usual. She didn’t see Mr Baldwin for the rest of the day so at least he wasn’t there to chastise her for her lack of speed. When she left Anna thought she knew what the cause of Jason’s distraction but decided to talk with him first.
Anna arrived home at 4:15 predictably ahead of Jason who liked to linger at friends’ houses before coming home. She decided to get herself a glass of wine and watch TV while she awaited Jason’s arrival.
***
Jason strolled into his house in a surprisingly good mood having spent the last hour or so hanging out at his friend Tom’s house. He immediately looked upstairs hopeful that he’d be treated to another view of his mother’s round ass. He was disappointed, however he soon spotted his mother, albeit fully clothed, walking out of the kitchen with a half empty bottle of wine.
“Sit.” She said, pointing to the couch in the living room.
Recognising the stern tone, Jason’s spirits immediately sank as he walked into the living room and sat as ordered.
“I had a chat today with Miss Lee who believes you are not trying in her class and that is why you have been failing assignments.” Anna waited for several seconds with no response. “Well?” She added.
“I don’t know what you want me to say mom, I’m easily distracted and it’s hard enough to concentrate in that classroom anyway, it’s always so hot.”
“I don’t want to hear any excuses. Are you failing any other classes?” She asked.
“No.” he answered, although he was only just scraping passes in some of the other classes.
“You better not be lying to me because I can go into school and check.” She threatened.
“I’m not mom I promise” he said, terrified by the thought of his mom marching into school.
“Then why are you failing English?”
“I don’t know.” Although he did know, how was anyone supposed to concentrate with Miss Lee looking like a Hollywood actress or underwear model; with her perky tits and round ass, strolling around the room, bending over to give students help with their work, in fact he was getting hard now just thinking about her.
Anna didn’t fail to notice her son’s rapidly growing bulge despite him leaning forward to try to hide it. This almost confirmed her suspicion that her son was too horny to focus. She had similar problems when she was his age, but in Math. She couldn’t concentrate as her teacher Mr Evans, fresh out of college, was the subject of many a daydream of hers, in fact she named her first dildo after him. She passed Math though, having cured herself of the daydreams by having a boyfriend fuck her silly at least once a day to keep her focussed, she decided that’s what Jason should do.
“Have you not thought about getting a girlfriend Jason? A good looking lad like you must have plenty of girls after him, maybe they could be a useful distraction, I know how stressful school can be.” Anna suggested. Although her thoughts had lingered on Mr Evans and the wine wasn’t helping as she started to get wet.
“I don’t know mom, it’s not really that easy.” He said, embarrassed.
“Of course it is, you just need to have more confidence.” She said, feeling pity for her son but also the horniness remained. “You should know, we girls get horny too, particularly teenage girls, I was always horny when I was your age but most guys were too shy to try anything.” Anna stated brazenly to her son, the half bottle of Zinfandel was maybe influencing the direction of this conversation more than she realised.
“Mom!” He said shocked and embarrassed at the sudden direction this conversation had headed, but also really turned on.
Anna decided that since his grades were suffering and he was at the moment too shy to get himself a girl she should, as his mother help him in any way she could. The thoughts of finally managing to seduce Mr Evans fresh in her mind, Anna dropped to her knees in front of her son.
“Maybe I can help, until you get a girlfriend.” She said reaching for the buttons of his pants.
Jason sat frozen. Holy shit! Holy shit! Holy shit! Holy shit! Seemed to be on a continuous loop in his head blocking out all other thoughts.
Anna undid the last button and tugged at the waistline of his black pants bringing his boxer shorts down with them. Her mouth started watering in anticipation as Jason’s nine inch, rock hard cock was revealed. Only once had Anna ever had a cock this long and that was a long time ago. At the sight of it Anna started to feel an all too familiar longing ache in her pussy as her thoughts became shrouded in a fog of lust. She looked her son dead in the eye and lowered her mouth slowly to the bulbous head of his impressive member.
Anna wasted no time and engulfed as much of his cock as she could which turned out to be only around four inches. Either Anna had never had a cock with this girth or she was losing her cocksucking skills.
Jason wasn’t at all disappointed by his moms skills, watching her bob up and down on his prick was like a dream come true. She was clearly trying to get as much of it in her tiny mouth as possible and Jason was enjoying watching her frustrated struggle as she just about passed the halfway point.
Anna’s eyes started watering as she managed to get about five inches of his cock in her mouth, she pulled it out just before she gagged and looked at it frustrated. She slipped her hand up her skirt and started to give herself some much needed attention, as she licked up and down each side of his cock.
Jason was in heaven as he watched his mom frig herself off while licking his cock like it was the best thing she had ever tasted. He heard her whisper more to herself than him “so fucking big” before she returned to bobbing on his cock with the enthusiasm of a pornstar and Jason decided to become less of a spectator and put his hand on the back of her head, guiding her up and down.
If possible Anna got even wetter as her son started to take some control. With her thong pulled to the side she was starting to drip onto the carpet, and was leaving quite a wet patch. The cock in her mouth was delicious to her, having not had one in so long and she was really worshiping it now. She pulled it from her mouth and slapped it on her face before showering the delicious fuckstick with sensual kisses. Next she licked and sucked on his balls while she continued jacking his cock which was still heavily lubricated with her saliva.
Anna was so caught up in the moment that she forgot it was her son’s hand which had now grabbed a handful of her hair, forcefully pulling her mouth back towards the swollen head of his mighty prick. Anna love when a guy took control like this and sucked the cock like her life depended on it as the hand on the back of her head was forcing her deeper onto the rock hard cock. A couple of seconds later Anna felt it erupt once, twice, three times, four times, before the hand relented and let her pull back to stop from choking on the salty cum. She swallowed gratefully, as she knew a good slut should, while the fifth and sixth ropes of cum plastered her face.
While her son was erupting down her throat and on her face, Anna had not stopped playing with her clit and having been so thoroughly and selfishly used as a cum dump for her sons huge load, she brought herself to climax right then and there covered in cum and squatting between her son’s legs.