This is the first in a series of stories about a teacher, his family, and his favorite student. All characters are entirely fictional and 18 or older.
Mr. Livshitz had a routine that he followed nightly when he got home from school, where he taught 12th graders Science.
When he was in class, as a way to ensure that he improved his practice, he would always record his lessons. But when he would arrive home, pull out his laptop, and take off his pants, he wouldn’t do so to evaluate his performance that day. No, the reason that he did so was a girl - his best student - Caroline Fairweather.
It just so happened that Caroline sat front and center in the camera frame every single day. And if Mr. Livshitz’ class was a TV show, Caroline would be the leading lady. She stood 5”6’, with hair that could be braided one day and permed the next. Her dark skin brought out the color of her hazel eyes and the plump nature of her lips. Her body – the 36c boobs, the curves, the ass that made Kim Kardashian’s look meager in nature – was always beautifully covered up, or not. Some days, she’d come in looking like she ran the place – blazer with a matching skirt, heels, the works – and other days she looked like she was already dressed for the party that she was going to that night.
Regardless of what she wore, she stole the scene that was Mr. Livshitz’ class daily – from the way her perky breasts would bounce in the bra that was able to be seen through her shirt on some days, to her snappy, wise comments on others. She was the total package.
On this particular day, Caroline had dressed down, wearing just a yellow cami that barely contained her tits and jeans that barely did the same with her ass. Some nights, Mr. Livshitz would pay attention to the faces of the other students in the class – the way that their facial expressions told all he needed to know about what was going on elsewhere. But tonight, he just paid attention to her.
Mr. Livshitz knew that his wife, Cindy, and his daughter, Abigail, would be home soon enough, but he continued at his regular pace. From the second he sat down, his cock would be throbbing from anticipation.
It was early on in the video when Caroline did one of the actions that Mr. Livshitz loved the most. He had asked the class a question about the reading from the night before, and it had stumped her momentarily, leading her to run both of her hands over her breasts as she thought. She did this daily, and it made him have to start touching himself immediately when it did. He ran his hand over his cock and began to please himself, imagining that she were at home with him, doing the work of pleasuring him instead of his homework.
In those moments, he imagined what it would be like to be with her, what her boobs and her ass would feel like in his hands or pressed against him. But he also watched closely to pick up signs that she was in on this, that she knew that he was going home and stroking his daddy cock to her.
It had started small at first. In the fall, he had noticed her glance at the camera every once and a while – more than anyone else did. Then, she had started to run her fingers up her thighs while looking at the camera. Another time, on Halloween, with her in a Harley Quinn outfit, she made it a point, he conjectured, to bend over in such a way that her ass appeared on screen only for him when she dropped her pen.
At first, he had thought himself crazy, back in the beginning of the school year. He was honestly watching the video back to see what he could have done better, when he noticed her gaze in one of the first videos of the year. That night was the first night he touched himself to her. His wife and daughter had both gone to sleep, and he quickly slid his cock out and came by imagining
Now, months later, with Christmas time in full spring, he decked his halls nightly watching her tease him, oscillating between enjoying the fantasy and very much believing her wants may align with his.
As he stroked his cock, he also turned himself on even more by imagining the ways that he dreamed of telling Caroline of his urges and finding that she felt the same way. He considered a detention where they were left all alone in the class. He thought about adding her on Snapchat and seeing what she would send – sometimes even going as far as pulling her account up on his phone and having his thumb hover over the “Add Friend” button. Each time, he cums just as his other hand is about to open Pandora’s box.
Tonight, he was thinking about the writing assignment they were doing, how she was probably sitting in a document that he was shared on at this very moment, and how he could pop his virtual head into the document and share some naughty words that they could erase in a moment’s notice. He moved away from the video on his computer and logged into his school email account recognizing the craziness in his plan. He switched back to the video, where he was greeted to Caroline licking her lips and looking at the camera for a few seconds longer than she would’ve by accident.
By this point, his mind was going wild with possibility – so wild, in fact, that he didn’t hear the door downstairs open. Instead, he continued stroking all seven inches of his cock with one hand while running his other hand all over his body. When he would get closer and closer to shooting cum hard from his cock, whatever fantasy or investigation always very quickly arrived at the same point: Caroline, naked, straddling Mr. Livshitz as her pussy bounced up and down on his thick cock. She’d always be leaning back, her back arched with her hands placed on her knees, and then she’d suddenly move forward, pinning him down with her toned, able arms. This would always be the moment that would force Mr. Livshitz to shoot his very real cum into her very imaginary pussy. Then, Caroline would always climb further up Mr. Livshitz’ body until she was dripping his cum into his own mouth.
But tonight would not be one of those nights, because just as Mr. Livshitz was about to blow, a noise made him come to a stop. It was an email alert on his phone, which he would normally ignore, but something in the moment told him to look. It was from Caroline - “Can we talk tomorrow after school.” No subject. No hello. No question mark, either. Instead, only a request.
Like a new character introduced in the middle of a TV show’s season, this email opened up a whole new world of possibilities for Mr. Livshitz to exist in as he stroked harder and harder, faster and faster, considering all of the things that may be said in this meeting, but more importantly, what may be done. He could feel himself getting closer, and closer, imagining himself lying back on his desk, Caroline riding him as if their lives depended on it.
He needed her. He wanted her. He would have her.
He could feel the orgasm rise within him, the cum leap out of his thick, pulsating cock, only for a KNOCK to interrupt one of the best finishes he had had in a long time. Cum spurted out of his cock in droves as his wife stood in the doorway.
Cindy was a few years younger than Mr. Livshitz, and she very much played the part of a made woman. Her body was in incredible shape, her blonde hair never had one tiny strand out of place, and her confidence was available in abundance every time she walked into a room. At that moment, that confidence made Mr. Livshitz feel very small, indeed.
Stripped from the fantasy world and crashed back into reality, he looked down to see cum not only on her chest but on the laptop as well. He paid the liquid an increasingly large amount of attention to avoid the eye of his wife as she walked over.
“That time of night again, Mr. Livshitz,” Cindy half-asked, half-stated as she grabbed the laptop – cum and all – and observed what he was watching. She looked on for a few moments, moments that very much felt like minutes to Mr. Livshitz, before she proceeded to hand him back the laptop.
She sauntered over to the other side of the bed in their room, grabbed a box of tissues, and worked her way back over to her husband with reinforcements in tow.
As he cleaned himself up, she sat down on the edge of the bed, grabbing his feet and rubbing them. She cleared her throat a few times before she said, “I told you to wait for me.”
Half turned on and half embarrassed, Mr. Livshitz blushed. “I couldn’t help it today, dear.”
“Well,” she began as she got up and made her way out of the room, “there’s always tomorrow.”