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The Life of Jack - Chapter 1

"O the life of College!"

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Author's Notes

"Ms. Waters"

Jack's life at university was going well. His grades were spectacular, despite the hard classes that he had taken this Freshman year; he made many friends, some of whom he liked better than others; and, most of all, he had his girlfriend, Sophie, whom he loved. Jack felt, for the first time, that he was in full control of his life; his destiny was his.

Unlike many of his high school friends, Jack did not travel outside of the state. Instead, he chose to continue his school life in his hometown. The university was just three miles from his childhood home, so he opted not to live in a dorm and stay with his step-mom (his father died in a fire when he was in the fourth grade).

It was on this day that the story of Jack took a very different direction. Jack was doing well in college, but he was only in the middle caste in his high school years. This was the first time he had a girlfriend, but so far, even with his girlfriend, who he loved, he never had any sexual activity. His desire was to engage in sexual activity with her only, but the urges of man are like the sun's gravity: he keeps only falling for his lust. 

He had just finished English class. Jack yawned. He truly likes to learn, but a long lecture easily bores him. It was something from Aldous Huxley's dystopian Brave New World, and the Professor was going off on the World State's view of sexuality and relationships. Something about the dangers of prioritizing pleasure. Jack was not worried about slipping in his grades in this class as he "had already read that book in high school. Trust me, Sophie, I have an astute memory when it comes to books." 

It was the afternoon. He had a couple of hours until he was supposed to meet Sophie at her apartment. Sophie also lived in his town, but he got her own apartment to live alone from her parents. Neither of them knew each other before university, however. Jack decided that it was best to finish whatever homework he had. He walked down the study hall and passed some people who he gave a quick nod. He opened the door to the study hall to find, to his amazement, that it was empty. Usually, he would find at least twenty people in the room, but not on this day. Still, Jack went to the back corner to sit. 

About an hour passed from doing homework and no one came in. Very odd, Jack thought to himself. And odd it was, not even the certified school nerds were in the study hall, and they were always there.

"Did you forget already, Jack?" said a voice behind him. Jack jumped in his seat, dropping his pen to the floor.

The voice belonged to the librarian, Ms. Waters. She was young for a typical librarian, but her enthusiasm for books was unmatched. She supervised both the library and study hall (which were adjacent to each other).

"Forget what?" Jack said after pulling himself together from the jumpscare. After responding, Jack looked at Mrs. Waters. He could not believe what he was seeing. Almost immediately he felt himself getting hard. Ms. Waters wore a brown and white striped dress in which only the nipples of her breast were covered by it. Both her underboob and her cleavage were clearly visible. The dress itself was held together by a (seemingly) loose knot between her breasts. Jack's mouth was wide open, and he gazed at her up and down, instinctively. Besides her breasts, the rest of Ms. Waters was also breathtaking to Jack. She had partially straight golden hair that went down past her shoulders. Her lips were coated with a natural-colored lipstick and she had curves to form a well-shaped ass.

Ms. Waters immediately noticed him checking her out but decided to ignore it for now. "I told you yesterday, Jack," she began, "Study hall is closed today."

"Closed?" Jack said, breaking his gaze from her breasts and moving it to engage eye contact. "Sorry, I totally forgot about it. I'll leave right away."

"No, I want to talk to you about something," Ms. Waters said, biting a bit of her lip. "It's actually good that it is closed."

"Oh, OK," Jack said. He was packing his notebooks away but stopped. "What do you want to talk about?"

"I want to talk about you," she began, "You were just checking me out, and I saw your boner as you stood to pack your things." Jack stood there blank, so Ms. Waters continued, "Jack, you know it is not appropriate to check out someone, especially someone who is on staff in a school."

"I...I..." Jack stuttered. He had no idea how to respond. This was not what he was expecting to hear.

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"It's alright Jack," Ms. Waters gave out a small laugh, "you checked out the right teacher. I don't mind it."

"You don't?" Jack said. His mind was going through a million things.

"Of course not, Jack. I wore this dress on purpose," she said. Every word was spoken quietly until she got to a whisper. She continued saying, "I've liked you ever since I first saw you in this study hall."

Jack was stunned. Ms Waters liked him?

"So," she said. She moved towards him and pushed him back in his seat. Her hand moved down from his chest to his boner. "Shall we?"

"I... uh..." Jack got out. "I have Sophie. I have a girlfriend," Jack said, finally able to get out a coherent sentence.

Ms. Waters looked Jack in the eye. "She doesn't need to know," she said as she began to rub his cock. She leaned in and kissed him on his lips. Her lips were sweet.

Jack gave in. He kissed her back firmly, wrapping his hands behind her back. I love Sophie, but Ms. Waters is so sexy, he thought to himself. Jack broke the kiss and took his shirt off. Ms. Waters put her hands on his bare chest and began to follow her hand to his pants. She began to pull his pants off.

"Ms. Waters!" Jack said, half screaming.

"It's Sasha, Jack," she said. She looked deep into Jack's eyes and said, "I want you to moan my name."

Jack helped Sasha pull his pants off with his boxers. She took Jack's cock in her hands and gave a smirk. She stroked Jack's cock, which caused him to tilt his head backward. Jack began to breathe loudly with his stroke.

Eventually, Sasha stopped stroking him. Jack took his head back up. Sasha took her hands to her breasts and shook them up and down, teasing Jack. "You want to do the honors?" she asked.

Jack gulped. He had never seen women's breasts before, at least not in person. Jack brought his right hand shakingly to the knot and pulled it loose. The knot easily came undone; Sasha threw away the fabric that covered her breasts. Jack got even harder. Her breasts were so smooth, sacking slightly. Her nipples were pink and had piercings in them.

"You want to touch them?" Sasha asked.

"Touch them?" Jack said hesitantly. "Yes... of course." Sasha guided each of his hands onto her breasts. At first, Jack was just touching them lightly, but quickly he gained confidence and squeezed them. Sasha gave out a half-laugh, half-excited squeal.

After touching her breasts for some time, Jack pulled his hands away. "Let's see the rest of your dress off," Jack said. Touching Sasha's breasts made Jack gain more confidence in taking charge.

Sasha laughed, "Gladly." She slipped the rest of her dress off with ease and threw it to the floor. Jack couldn't see her pussy, but he put out his hand in search of it. After finding it, Jacking rubbed her pussy gently with his fingers. Silent moans came from Sasha's mouth.

"Mmmm... put your cock in me, Jack," she said.

Jack got out of the chair that he was sitting in and lay on the floor. Sasha got on top of him and put her hand around his cock, teasing him. Finally, she slowly began to sink inside his cock. As she got further in, Jack released more and more moans until he was all the way into her. "Sasha," he whispered.

Sasha moved up and down on his cock, gaining speed with each thrust. Her breasts were jiggling up and down.

"Sasha," Jack moaned, "I'm going to cum!"

But Sasha kept going with no signs of stopping. Jack felt a great sensation building up until at last he released, with a surge of pleasure, his seed inside Sasha's pussy. She slowed down until she stopped altogether and released the grasp of her pussy from his cock. Jack's white cum was oozing out of her pussy.

"How could you!" Jack almost yelled.

"It's fine, Jack. I'm on the pill," Sasha reassured.

Jack made a sigh of relief. "Oh good. I will admit it. I did like cumming in you," he said.

Sasha laughed, "I knew you would. Well, that was fun, Jack. Perhaps we should do this again?"

"Maybe," Jack said, "but I'm still dating Sophie."

"You can always still have fun. If you ever want fun, come to the library," Sasha said. She put her clothes on and left the study hall.

Jack sat back down in his chair. I had just lost my virginity, and I cheated on Sophie, he thought. But her boobs were so big and nice. Jack got dressed and left the room.

Published 
Written by Layla_b428
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