Hard, and the audience is pleased

*SMACK*

The first spank was sharp and fast, causing Rebecca to draw a quick breath.

*SMACK*

*SMACK*

*SMACK*

"Ah! Ah! Mmm," she moaned. She seemed to be doing quite well so far.

*SMACK*

"You've decided to be quite a naughty girl on your first day, Rebecca," teased Jared, drawing a "tsk tsk," from Aileen.

"Ugh!" she groaned in frustration, as Jared continued with a tougher spanking than the one she had received earlier.

*SMACK*

*SMACK*

*SMACK*

"It's also very irresponsible of you to make your mother wait like this," he continued to tease.

*SMACK*

"Hey! Owww! You're the one making—"

"What was that?" Jared interrupted, delivering several quick spanks to her now bright red ass.

*SMACK* *SMACK* *SMACK* *SMACK*

"Owwww-ow-ow-nooo! I'm sorry-sorry," she pleaded.

Jared was horny, and knew that the combination of a hard spanking with constant teasing would cause rambunctious Rebecca to make a mistake. A mistake that he would most certainly capitalize on. He looked at Aileen and smirked. She met his eyes and bit her lip. He felt his dick press even harder into Rebecca's stomach, eliciting a small moan of disapproval from her.

"I'm disappointed in you, Rebecca. I'm being very generous by not giving you that 10th demerit, but I can't just let an outburst like that go unpunished," he explained, while his hand continued to come down on her juicy ass and his cock continued to press against her.

"I'm sorry! Ow! Ouch! Please forgive me! Ow!" she begged.

"When we begin the next round, you will have a total of 3 minutes to make me cum. You remember that, correct?" he explained, continuing to smack her bottom.

"Yes, Sir. Ah! Ow! I remember," Rebecca answered, as if she were trying actively to forget.

"Well, due to that little outburst, I'm going to give your mother the opportunity to spank you as well. After all, she's the one you are holding up," Jared stated, smiling while he looked in Aileen's direction. She looked surprised but curious at the same time.

"No! What?! You can't do that!" she shot back, the sound of her spanking filling the room.

"Another outburst? Tsk tsk. I think I have something that will help you understand who is in charge here," Jared said, halting the spanking for the first time since it began.

He brought his watch up and paused the timer.

"Oh, uhm, I'm sorry," Rebecca said as she caught her breath, "I j-just, uh, I didn't think that—AH!"

Jared had taken hold of both her beautiful, red cheeks and slowly pulled them apart, revealing the tightest asshole he had ever seen. Wasting no time, Jared gathered as much saliva in his mouth as he could and dropped it slowly onto her knot.

Rebecca was silent, frozen in fear from the invasion and anticipation of what was to come.

Using his right index finger, Jared began to slowly massage his spit around her anus, applying a small amount of pressure. Rebecca was involuntarily flexing her buttocks in reaction.

"You'll need to relax, Rebecca. This will be more painful if you do not," explained Jared, dick harder than it had ever been.

"W-what will be painful? What are you going t-to do?" asked a panicked Rebecca.

There was no need for Jared to explain, as he began to push his finger into her resistant ass.

This girl is tighter than shit! thought Jared, slowly working his finger into her entrance.

"Ah-ah-oh-ahhh! Oh! Ow-ow-ow-ow-ow! Nnngh," Rebecca moaned in pain.

"Relax, Rebecca. I need to get it all the way in," explained Jared.

"Ow, wait! Sir, no! I'm sorry! I'll be good!" she implored.

Jared ignored her as he pressed onward. He wasn't making a ton of progress, as expected with a hole as tight as this. He pulled the finger out for a bit, causing Rebecca to moan.

"Oh, thank you, sir! I'll finish the spanking like a good girl," she assured him.

"I'm glad to hear it. However," he continued, applying more spit to Rebecca's asshole, "I've only made it a single knuckle in so far."

Rebecca was silent again, trying to register the sensation of saliva making its way into her violated anus.

Jared returned his finger to the entrance and picked up where he left off.

"Nnnngh," Rebecca braced.

He used his other hand to pull her soft, hot flesh out of the way as she continued to offer resistance. The spit was helping significantly as he worked it deeper into her ass.

"Mmmmm-ah-ah-nnnngh," she moaned in response.

Now almost all the way in, Jared was struggling to get any further. He withdrew one more time to add some more lube, eliciting another sexual moan from Rebecca.

As Jared's spit reached her anus, Rebecca was confronted once again with the strange sensation of liquid entering her rear, this time making it deeper into her body. She didn't have long to analyze it, though, as Jared's finger returned on a mission this time.

Jared quickly pushed his finger in all the way.

"AHHHH! Owww," sobbed Rebecca.

With her tight little ass now filled with her pervert boss' finger, Rebecca was overcome with shame and guilt. She began to sob, although softly and reserved.

"Well done, Rebecca. I can tell that this is the first time someone has fingered you... like this," he observed, wiggling his finger for emphasis.

"Mmm yes, sir. This is my... my first time," confessed Rebecca, tears beginning to form in her eyes. Although embarrassed, she couldn't deny the feelings deep in her loins.

"I'm actually surprised by that, Becca," confessed Aileen, "I sure hope you conduct yourself appropriately from now on. If you don't, maybe it'll be more than a finger next time."

Rebecca whined in disapproval, but Jared could see her pussy glistening in excitement.

Looks like I'll make an anal slut of this girl yet! Jared thought excitedly.

He retracted his finger slowly, causing Rebecca to moan involuntarily one last time.

"Now, Rebecca, be a good girl and take your spanking without any further outbursts," demanded Jared

"Yes, sir. I'll be good," she assured him.

Jared resumed the timer with 34 seconds left in the punishment.

*SMACK*

*SMACK*

*SMACK*

Rebecca's sobbing grew a bit louder, although she was most certainly holding back any responses other than grunts and moans.

*SMACK*

*SMACK*

*SMACK*

Her ass was bright red and glowing, her boots and dress framing it beautifully.

*SMACK*

*SMACK*

*SMACK*

Jared's watch began beeping, marking the end of the first round. He looked down on the hot, teen. She was sobbing quietly now, her violated ass on full display as he softly traced the dimples on her lower back.

"I'd say that you've been thoroughly spanked today, Rebecca," began Jared, "but unfortunately, you decided to talk back to me."

"I'm sorry, Jared. Please..." Rebecca pleaded openly.

"Stand up," he commanded. "It's time to decide how your mother will be spanking you."

Aileen also stood in anticipation of her involvement.