Harder than he ever has

*SMACK*

The crack of the yardstick on flesh was sharp, drawing a gasp from Rebecca. Jared seized the moment and entered her warm mouth, eliciting a small gag reflex from the girl. He knew he wouldn't last long. This scene was unbearably hot. The woman he lusted after for so long was in front of him, spanking the hottest piece of ass he'd seen in a long time.

*SMACK*

"Mmmmm," moaned Rebecca, sending vibrations along Jared's shaft. He didn't move, even though he wanted to grab her by the hair and fuck the absolute life out of her face. He knew that would only bring this experience to a close sooner. Rebecca took notice. She propped herself up a bit with one arm and brought the other in front of her. She gripped the base of the throbbing member in her mouth and began to pump it.

*SMACK*

Rebecca winced as her mother brought the yardstick down on her sore and violated ass. Despite the pain, she set her sights on the goal of making her new boss cum down her throat. Jared felt his balls tightening in anticipation of release, but did his best to reduce the tension in his body. He brought up his watch and wasn't surprised to see that only 20 seconds had passed.

"Losing willpower, Jared?" teased Aileen. He felt a surge of strength as he smiled back at her.

*SMACK*

Aileen seemed to be having a great time. She took a second to roll up her sleeves and Jared noted a shininess to her complexion. Whether it was the effort alone that was making her perspire or the excitement of the situation, she looked amazing.

Rebecca was also hard at work, milking Jared's cock like a madwoman. Jared thought about how different this was from the beginning of the punishment. Perhaps it wasn't inexperience, but laziness. Even though she was rushing still, it was much better this time around.

*SMACK*

"Nnnnghh," Rebecca groaned. Jared checked his watch again and saw that only another 20 seconds had passed.

"Mmmm how's it feeling up there, Jared?" prompted Aileen.

"Feels good," he answered simply.

"Just good?"

*SMACK*

Rebecca moaned again as she removed her bosses dick to get some air. Jared looked down to meet her gaze. She put on her sexiest eyes as she continued to pump his cock in her hand.

"Becca, if you don't start trying, Jared's never going to cum," teased Aileen.

Rebecca seemed to be ignoring her mother, continuing the lusty exchange with her perverted boss. She stuck out her tongue to reveal a pool of spit.

*SMACK*

She winced on impact, but then went right back to business. Jared watched as Rebecca licked his shaft from balls to head, coating it in her saliva. When she was satisfied, she brought it back into her mouth. Jared moaned in pleasure as his dick was enveloped in the brat's warm, little mouth. She moaned in return, drawing him back to the edge quickly.

*SMACK*

"That's a good girl," Aileen remarked. It seemed to have a positive impact on young Rebecca, who moaned in response.

Jared checked his watch again. They were at just over a minute, and he knew it would be over if he simply gave in.

"Oh my," Aileen stated with false shock, "what do we have here, my sweet Becca?" Aileen placed the yardstick down on the table and leaned over to inspect her daughter's sex. "My goodness, you're positively gushing, dear. This is meant to be punishment, but here you are enjoying every second of it."

Rebecca furrowed her brow in response, but kept her attention on Jared's dick.

"Well, like mother like daughter I suppose," Aileen said, giving Jared a wink as she gave her daughter one last spank with her hand.

Oh fuck, Jared thought, his brain turning to mush as every ounce of blood was drained from it. His balls tightened and he quickly reached his limit. Rebecca felt the orgasm coming and began to jerk him more vigorously, moaning and whining all the while. Every muscle in Jared's legs contracted as he began to shoot ropes down poor Rebecca's throat. It had been several days since he had an orgasm, an even longer since it was involving someone else. All of that pent up cum was now flooding into Rebecca's mouth, and she was struggling to swallow all of it as she was instructed.

"Mmmm good girl. Drain every last ounce of cum from those balls," Aileen encouraged. Hearing her talk like that was only adding to Jared's already intense orgasm.

Miraculously, Rebecca didn't spill a drop as Jared's climax finally came to a close. He panted as he slowly withdrew his cock from her lips. She finished swallowing the cum and showed her tongue as proof.

"Well done, Rebecca," Jared congratulated, almost no energy behind his voice.

"Thank you, sir," Rebecca replied.

Jared looked over at Aileen. She had already rolled her sleeves back down and collected herself.

"Alright, dear. Collect your things. It's late and I'd like to start enjoying my weekend," commanded Aileen, who had now taken on her usual, everyday demeanor.

Rebecca lifted herself up and pulled her dress down. She stepped off of the table and grabbed her belongings.

"Say goodnight to Jared and thank him for punishing you."

"Thank you, sir. I'm sorry for being bad," Rebecca said as she looked at the ground.

"Goodnight, Rebecca. I expect you to do better on Monday," Jared stated.

"Yes, sir. Goodnight."

With that, Rebecca made her exit, leaving the door open for her mother to follow as the thud of her boots grew quiet in the distance.

Just then, Jared's watch began beeping. He looked at it to turn it off and was caught off-guard by Aileen's presence right in front of him.

She reached down and grabbed Jared's dick just as it had begun shrinking, causing him to freeze. With her other hand, she reached around and gave his ass a squeeze while she moaned.

Jared wasn't sure what to do, but that didn't seem to bother Aileen as she leaned in for a kiss. Even in his frozen stupor, Jared managed to return the kiss, which ended up turning into a passionate make-out session.

Holy shit, what is happening?! Jared thought, still not sure if he hadn't just dreamt the entire day.

Aileen finally withdrew her hands and lips, "See you next week, stud."

With one final wink, she too made her exit.

Jared was now somehow hard again, staring blankly at the foam roller and yardstick on the table as the sound of Aileen's heels grew ever quieter.