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As the cane whistled through the air, only stopping when striking my innocent palm with a crack, I yelped at the pain emanating from my hand. I had promised myself I would take my punishment stoically and not cry or make a fuss but never realised that the Things had changed for Miss Julie. She was now twenty-three years old, five feet nine inches tall, with a Mediterranean look, a very pretty face framed by her dark hair, had gorgeously pert breasts, a lovely figure, and a very strong personality to go Help yourself to anything. And, stay as long as you need to.

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Then she gave him his last strike. She carefully separated his ass cheeks with her left hand, and slowly inserted the index finger of her right hand in his rectum. Her breasts seemed to bounce more, and her hips always invited him to look at them. She then began to gently apply the lotion to his very sore ass cheeks.

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Their conversation quickly turned to experiences their families had shared over the years, both happy and sad. He thought that she might wipe off his dick for him, but he was amazed at what she did next. She left to go to the kitchen, and returned with a wash cloth to clean him, as well as the floor. She quickly had her whole finger up his ass, and was able to stroke his prostate.

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Then she did something that Jeremy did not expect. She then got milk from the refrigerator, and glasses from the cupboard. He looked at the switch, then at Mrs. Jackson, with a slightly curious look on his face. After about the tenth spank, he began to grunt as her hand made contact with his ass. She came around his side and looked at the large amount of cum that he had deposited on the floor.

It was at this point that Mrs. She helped him up, and while she saw his fully erect penis, she made no reference to it. Lesbian Encounter With Young Kate.

It was at this point that she helped him onto her lap. Instinct made him bend and unbend his knees in an effort to reduce the pain. After a few minutes of rubbing, she released his balls only to grasp his penis with her four fingers, and caress the tip of his dick with her thumb.

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He gently rubbed his sore ass while she moved the chair back to the table, only to return with the switch. Picking up on this, Mrs. Realizing that this was something he really wanted to experience, Jeremy looked at Mrs. She put the switch down on the kitchen table, picked up one of the chairs and carried it into the living room.

Jeremy was a complete loss for words. Then she unbuttoned his pants button, and lowered the zipper. Jeremy followed until he saw her put the chair down. He clenched his ass cheeks in fear, but was not totally prepared for the excruciating pain he was to feel. Jackson then got up from the table, and went toward the back of the house.

He heard her open the tube, and put some on her hands. They stood in the entry way and exchanged some small talk. Jeremy had no idea why this was happening to him, but his penis was now harder than it had ever been.

Their discussion turned when she brought up the time when he and Steve had been caught with a six pack of beer. Jackson stopped the massage, and applied another squirt of lotion to the fingers of her right hand. This time she hit a new spot, and he was able to keep from yelling. They just missed his chin, and landed about four feet in front of him on the floor.

Jeremy sat at the kitchen table, while Mrs. Jackson brought a plate of cookies for them. She then sat down, and looked at Jeremy. She told him about old Mr. Potter who had locked himself out of his house without his glasses, and how the girl scouts had sold a case of cookies to Mrs. Fletcher, who had them sold them at her garage sale.

When she started spanking again, she spoke to him in a very harsh tone, scolding him with each spank. Jackson replied. The first strike instantaneously caused his eyes to fill with tears again. Keywords femdom milf older woman spanking younger man.

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Giving up, Jeremy asked about Steve. Both families were planning to celebrate, but even though he tried to get some clues out of Mrs. Jackson, Jeremy had no luck. There was never any overt sexuality on her part, but there had been times when just being close to her had raised his temperature in ways that no one else ever had. Then, raising her right hand, she beckoned him to her with her index finger.

At this moment it occurred to him that the woman who had taken some very interesting trips through his imagination, was now handling him in a most erotic manner. He may have dreamed of this type of thing happening to him, but never had he believed that this might actually take place. Jeremy was now intensely aware of his predicament. When she pulled his pants down, he had to put his left hand on her shoulder for balance as he stepped out of them.

With both hands, she then lowered his shorts about halfway down his thighs. Jeremy was almost as his end of his endurance.

This was as much as Jeremy could take. He lost count around 25, about the same time that his eyes began to water. The movement of his body against Mrs. He was relieved that she had stopped spanking, but also frustrated that he was so close cuming without an end in sight. She continued to milk his penis until it started to deflate, at which point she also removed her fingers from his rectum.

Also due to the fact that Mrs. Jackson was wearing a short skirt, his semi flaccid penis was now in direct contact with her bare thighs. When he regained a modicum of composure, Mrs. Jackson gave him his fourth strike. Jeremy heard the switch as it whistled through the air. All at once, she stopped, and he could hear her breathing hard. Jackson had gone for a tube of hand cream. Not wanting to go home to an empty house, he agreed to stay.

Jeremy was at a loss for words at this point. Jeremy stood up after getting the second shoe off, and then was somewhat surprised when Mrs. Jackson reached out, and began unbuckling his belt. Determined to last through the fifth, Jeremy steadied himself for the third strike. Reing him at the table, she asked lots of questions about how his year in college had gone. The next thing Jeremy heard, although he was afraid to look back, was her rubbing the cream on her hands.

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She followed this up by letting her left thumb touch the same spot. She returned rather quickly holding the switch. He was way past watery eyes; he was crying and taking deep breaths. An involuntary shudder went through his body that she could not miss. Now that it was over, Jeremy attempted to stand up, but Mrs. He heard her walk out of the room, only to return a few seconds later. Spanked by Mrs. Total 0 votes. In a very short period of time, he was now standing in front of a woman he had long fantasied about, with his penis completely exposed.

She was about the same age as his mother, but a little taller, with longer, brownish hair. She also increased the pressure on his penis by tightening her grip. Over the next few minutes, she continued to massage his cheeks, but at one point, the thumb of her right hand grazed against his asshole. She really only had to flick her wrist, and the switch made crisp contact with his butt. Slowly, but ever so surely, Mrs. Jackson was working him toward the biggest release of his life.

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In fact, if he thought that it might help, he could have asked her to stop, but he decided to complete the punishment for nothing else but his manly pride. What he never expected was how hard his cock would become. Art Appreciation. This time she was able to hit the exact same spot as the second strike. Without saying a word, she knelt in front of him, and put his dick in her mouth.