Caramel Part 7

Ms. Jones was allowed to go into the principal's office only after she agreed to the secretary's instructions to remove her panties and hold her skirt up to her belly before she entered Buck's office. The principal liked for his student's mothers to show the proper respect whenever they came into his office to beg for favors on behalf of their children. He knew that Ms. Jones' daughter, Amelia, wasn't doing well in her math class but that she was expected to ace all of her courses so she could get into a good college after she graduated. Her parents did not want her to spend her life in squallid mediocrity.

After the pretty mother entered his office he decided that just having her hold up her skirt to expose her hairy vagina wasn't enough so he told her to keep her skirt up with one hand while she pulled her breasts out with the other.

It was a struggle and Ms. Jones felt clumsy as she fought to pull her breasts free of her bra. After that he told her to start masturbating in earnest while she begged on behalf of her daughter.

Ms. Jones, Agatha, had heard about the principal's reputation for demanding submission from not just his students but their parents as well so she tried to remain calm as she rubbed her pussy with one hand, held her skirt up with her other hand, and explained that her daughter, Amelia, just needed a little extra time before she could retake the math test she had failed. Agatha tried to assure the principal that she would make her daughter study harder. All the while Agatha was getting hotter and hotter. Despite her humiliation at having to beg in such a demeaning sexual manner she couldn't help but start thrusting her pelvis forward towards the handsome commanding black man in front of her as she started to climb towards her climax.

But before she could cum Buck got up from his chair, came around to face her, and told her to get to her knees but to continue holding her skirt up and to continue masturbating.

Ms. Jones gladly kept fingering herself as she watched the principal lower his jeans and let his impressive cock dangle just an inch or two from her face. When he asked her to open her mouth she fully expected him to force her to give him a blowjob, which, considering how aroused she was, she would have been happy to do. But, instead, he merely held his swollen cock head forward and began to urinate in her mouth.

Agatha had a hard time masturbating and swallowing the principal's urine at the same time. She had never done anything like that before but she had heard the rumors and was somewhat prepared for his demands. Still.... it was a difficult feat to accomplish but she really wanted to help her daughter do well in school so she gave it her best effort and managed to only spill a few drops down the front of her exposed breasts.

When he was done he ordered her to continue fingering herself as he got on the intercom and told the secretary to have Amelia pulled from class and for her to come to his office asap.

When Amelia got to the outer office the secretary told her to lower her school uniform skirt and panties to her knees, open her blouse and lift her tits from her bra and to then go into the principals office.

Amelia struggled to walk with her skirt and panties down around her knees but she managed to waddle inside. When she saw her mother masturbating on her knees and clearly on the verge of orgasm she hesitated only for a moment before she went over and stood beside her mother facing the principal.

"Hand's behind your head, Amelia... fingers interlocked." '

Amelia obeyed.

"Your mother is asking me to give you more time to pull up your pathetic grades in math. Do you want me to grant her this request?"

"Yes, sir. Please. I p-p-promise to do better next time... Sir."

"I am not convinced of your sincerity so I am going to test you both. If you pass I MIGHT grant you some extra time. Nod your heads if you agree to this test."

Both mother and daughter nodded.

The principal then stepped forward slightly and put his cock in the mother's mouth. Amanda knew what he wanted so she started to bob her head and work her tongue and lips up and down over his manhood.

As Amanda sucked his cock Buck ordered Amelia to lean over his desk and to reach back and spread her cheeks. He then complimented the mother on what a fine-assed daughter she had raised.

"Thank you, Sir" Amanda replied as she momentarily removed her mouth from his cock.

"If you can do well enough to make me sufficiently aroused, Ms. Jones, I am going to sodomize your daughter and then cum in her ass. Have you ever had anal sex, Amelia?"

"N-n-no, Sir."

"Well then I suggest you start lubing up your daughter's butt, Ms Jones, or it is going to be an excessively painful experience for your daughter."

He then instructed the daughter to slide over closer to her mother so that her mother could reach her hand out and begin stretching her daughter's anus with her fingers; at first one finger and then two. "At least two fingers, Ms. Jones" he said. "Considering my size I should think she needs all the stretching you can provide."

And just like that Amanda found herself partially nude, on her knees, fingering herself, sucking off the principal, and gently yet firmly trying to push the fingers of her hand into her daughter's tight little butt. She felt like some kind of sexual triathlete as she felt herself getting hotter and hotter from her hand still rubbing her pussy, felt the principal's cock swelling more and more in her mouth, and listening to her daughter's soft moaning as Amanda pushed her fingers ever deeper into her teenage daughter's rectum.

Buck looked up into the corners of the ceiling to make sure that the red light was on for all four cameras mounted there. He knew he was going to make a lot of money off of the videos that were being made at that moment. Mother and daughter sex was a particular favorite among many of his paying customers and he knew this one would prove to be above average. How often did one get to watch a mother take her daughter's anal cherry? Plus, he knew that he could appeal to the mother's concern for her daughter to persuade her to put on a strap-on to further enlarge her daughters little hienie before he butt fucked the shit out of her... hopefully... butt not literally.

Sure enough the eventual sight of the mother bending over and slowly humping her upside down daughter and forcing a large black strap-on dildo up her daughter's very tight and tender young butt hole did not disappoint. Soon both mother and daughter were moaning in rhythm as the dildo pushed in and out through the poor girl's very tightly stretched sphincter. And, as if that wasn't enough, in the middle of this incestuous taboo the mother started to cum from the sheer pleasure of the strap-on cup rubbing against her pussy mound and from the thought of the naughtiness of their forbidden coupling. And as she came she couldn't help but push her throbbing clit harder and harder against the strap-on cup; thereby driving the fat dildo deeper and deeper up her poor daughter's already painful ass and deeper and deeper into Amelia's colon.

When the mother finally collapsed in a heap the principal pulled her aside and took his place in his student's upturned backside. The velvety friction and deep heat of Amelia's clenching butt hole was so intense that Buck was reminded of why he loved his job. Where else could he get young teenage girls to willingly bend over and let him butt fuck their virgin asses.

Buck ejaculated deep inside Amelia's butt as her partially nude mother sat on the floor next to them and watched.

"Let that be a lesson to you" he said as he sat back down in the big chair behind his desk and looked deep into the teary eyes of his student. "You have one week to prepare and retake the test. You do not want to know what you would have to do for more time than that. I am going to assign one of our new tutors, a Ms. Caramel, to help you. Now get out of my office. You sicken me."

"Yes, Sir. Thank you, Sir" both mother and daughter said gratefully as they stumbled out of his office.