Chapter 10

It was a typical slow Monday for Bob, who often struggles with early mornings. Nonetheless, he managed to get up and go to school. His routine involved moving swiftly through his classes, but this particular Monday took an unexpected turn. In his math class, his teacher requested that he stay behind after the course for a discussion. This unusual request left Bob pondering about the possible reasons.

After the class concluded, Bob approached the teacher’s desk, waiting for her to finish her tasks. During this time, his attention was drawn to a girl nearby. She had a distinctive look, one that Bob couldn’t help but notice, especially her prominent bosom. This observation added an element of distraction to Bob’s wait, diverging his thoughts from the impending conversation with his teacher.

Meet Daisy Harper, a confident and vibrant 16-year-old girl. Standing at about 5 feet tall, Daisy radiates positivity and self-assurance. She is a beacon of body positivity, embracing her unique figure and challenging societal norms with pride.

Daisy’s fashion choices are a harmonious blend of bohemian and hippie styles, perfectly accentuating her curves. She often wears flowing maxi dresses crafted from soft, breathable fabrics, which elegantly drape over her body. These dresses are frequently paired with colorful fringed vests, adding a splash of brightness that mirrors her lively personality.

Daisy Harper’s unique style was easily noticeable with her long, wavy hair that cascaded down her back, often styled with various braided hairstyles and adorned with charming flower crowns. Her love for accessories was evident in her frequent use of beaded necklaces, bracelets, and rings, each adding an extra flair to her ensemble.

During a conversation with their teacher, Mrs. Thompson, Daisy openly shared her struggles with math and her eagerness to improve. Mrs. Thompson, impressed by Daisy’s determination, suggested she get extra help outside of school. Knowing Bob’s proficiency in math, she saw him as a perfect candidate to assist Daisy.

Mrs. Thompson proposed the idea to Bob, “Bob, do you think you could mentor Daisy here to help improve her math grades?” Bob responded affirmatively, “Sure, I can do that. I’ll mentor her after school until she passes her next test.” Mrs. Thompson encouraged him to discuss it with Daisy before leaving.

Turning to Daisy, Bob introduced himself, “Hello, Daisy, my name is Bob. I hear you need a mentor for math. When can we get together?” Daisy promptly wrote down her address on paper, handed it to Bob, and said, “You can meet me after school at my house; it’s a short walk from here.” With a wave of goodbye, Bob replied, “See you then,” setting the stage for their upcoming tutoring sessions.

Bob arrived at Daisy’s house that afternoon for their first tutoring session. The mood was encouraging and cheerful as they settled at the dining table to study. Daisy had changed into a lovely summer dress for the session, which added a relaxed, comfortable atmosphere.

As they delved into the math problems, Bob patiently explained the concepts, adapting his teaching to suit Daisy’s learning style. Together, they worked through practice problems, with Bob sharing helpful tips and shortcuts he had picked up over the years. His calm and understanding approach helped Daisy feel comfortable, encouraging her to ask questions and engage more deeply with the material.

This collaborative environment fostered a productive session where Daisy felt supported and motivated to improve her math skills.

Bob settled into the tutoring session at Daisy’s house and inquired about her parents to better understand their study environment. Daisy informed him, “They are working. We have the house to ourselves. Care to come up to my room?” suggesting a change of location for their session.

Upon reaching her room, Bob, focused on the task, asked, “What did you have in mind?” His question aimed to bring the focus back to their math studies.

Walking towards her room, Daisy replied with a mix of personal thoughts and curiosity, “Well, I have some questions I would like to ask you. Are you kind? I am curious. I am Shy. I am also a virgin. Oops. I was not supposed to tell you that.” Her words reflected a blend of openness and a bit of nervousness in the new tutoring situation.

Probably taken aback by the personal nature of her comments, Bob would likely aim to redirect the conversation to their primary objective of math tutoring, ensuring a comfortable and professional atmosphere for their study session.

In this exchange, curious about Daisy’s earlier statement, Bob asked, “Why were you not supposed to tell me? Who said you should not tell me?”

Daisy, sharing the advice she received, replied, “When we made this plan, Carol said I should not mention that I was a virgin as she thought you would be more willing to make love to me.”

Bob, responding to this unexpected turn in the conversation, said, “She was probably right, but I will anyway.”

In this scenario, Bob followed Daisy upstairs to her room. Observing her, he contemplated the direction of their interaction, especially given the personal nature of their earlier conversation. Daisy’s room, tidy and organized, reflected her personality. She sat on her bed, and Bob joined her, still under the impression that their meeting was for math tutoring.

Daisy, continuing the personal tone of the conversation, said, “I would like you to care for my little problem?”

Bob, unsure of what she was referring to, asked, “What would that problem be? And why me?”

“I have seen the changes in Carol since the beginning of school. That can only be attributed to you and your relationship with her. Carol seems to have a cheery disposition and a smile like she has been sexually satisfied. I have yet to experience this. So, can you make love to me?” Daisy grabbed his hand, hoping that his answer would be yes.

He said, “Well, of course, I would love to make love to you, but you still have clothes on. I would suggest you take them off and lay in bed. Would you like some romance, kissing, caressing? Or do you want to jump right into it?”

She was not ready for that answer. And now she was beginning to shy back into herself. So Bob reassured her by taking her hand and placing it on his crotch. So that she could see and feel what was about to enter her, she smiled at him—and started rubbing his crotch. Slowly, at first, she was undecided about what to do. So he reached over to her lips and kissed her. To make her feel more at ease. He moved one of his hands to her, caressing her legs. Her thighs are soft. She was raising the dress to a point where he could see her vagina lips glistened with moisture. Slowly he moved closer to her hairy pussy, until his fingertips could feel the heat from her cunt. She was dripping wet and was warm to the touch.

His fingers brushed the outside of her pussy lips as they opened for him. As he kissed her, she unbuttoned her dress to expose her massive breasts. She had removed her underwear when she got home in preparation for the afternoon deflowering. She started caressing her boobs as they were susceptible to her touch. She dropped the top of her dress down to the waist. His fingers were moving all over the vulva area, and he went in search of her clitoris. It had just erupted from the hood and was very pronounced. His fingers pinched and rubbed the clitoris for a minute when she had her first orgasm.

She was unprepared for the intensity of her first orgasm. Bob began slowly, warming her body between her legs, touching her clitoris for the first time when her clitoris became very aroused, which was about the size of an eraser. Big enough for him to pinch between his fingers. As he did, he reached for her clitoris and started squeezing it between his fingers. That is when her orgasm began moving her hips from the bed, with the intensity of the sensation. She grabbed hold of her clitoris hard as the orgasm swept over her, and she said, “Oh my God, is that one of an orgasm feels like.?”