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A Shy Guy's Notebook Part one: Meeting Amy

James, a shy and socially awkward eighteen year old lad, is gifted an mysterious notebook
James had always been extremely awkward in social situations. Being painfully shy, he struggled to keep conversations going with anyone. At the age of eighteen, he was in his final year of sixth form (further education in England) and he knew that in a few months he would be venturing out into the big, scary world of university life.

He was quite average in most aspects of his life. He wasn’t too tall or too short and not too overweight, but not exactly the poster boy for physical health. He had dark, brown hair that he would usually just leave as it was, scruffy and a bit too long. He did not care too much about style and would just wear simple t-shirts and jeans in order to not stand out. He did have some good qualities in terms of his appearance. He had been told once or twice before that he had lovely blue eyes, but James assumed that they were joking. His smile was not too bad either, but at school he did not smile all that often.

As far as he could remember, he had always been more of an outsider at school. He did have a few friends, but they were not very reliable. They would usually forget to invite him to meet ups and would often chose to hang out with other friends instead of him. James thought of himself as the “back-up” friend and would often spend most breaks between lessons, alone.

In class, he could not get much conversation out of his peers. He was quite the worrier and would fear people’s reactions if he suddenly tried to join in with their discussions. He would worry that they might think it was strange if he suddenly tried to strike up a conversation with them. Even when he felt the nerve to talk, he could not think of anything to say. To make things worse, when people actually did speak to him, it came as such a shock that he would only manage to respond with one word answers or just nod awkwardly. Eventually they decided not to bother with him at all. James would sometimes go entire days without any social interaction at all.
Now, even at the age of eighteen, he had never had a girlfriend; been on a date, kissed a girl, held hands with someone, well damn it, he had barely had a proper conversation with a girl. That did not stop him from having crushes though. He would be captivated with women from a distance, wishing that he could just romantically wisp them away. If only he had some sort of special look he could give a woman or a magical line that would win their heart in a matter of seconds. He had not yet grasped the truth that women were not these mystical creatures and that a decent conversation would just as suffice. It did not take much to win his affection. A girl literally had to just smile at him one time and after that he would be hooked and head over heels for them.

But this is where our story begins. As we have established, James is a very insecure, shy lad who was just living his mundane life. This day seemed like it would be as normal as any other…

The school bell rang to signify the end of the fifteen minute break and that lessons were once again ready to begin. James was already at the door to the classroom. He had spent the break just waiting outside it, having nothing better to do. He strolled into the room and took a seat near the front. A few moments later, groups of fellow students started to flood into the room. James watched them enter, chatting and laughing away. One of the people walking in had James’ full attention. Lucy.

Lucy was a beautiful creature, one that had boys falling for her wherever she went. She had long, luscious, blonde hair that she would put up in a ponytail. It would flick side to side as she turned her head. She was quite athletic, being part of the cheerleading team, with nice toned legs that she loved to show off in her tight fitting shorts. The shorts left little to the imagination about the magnificent curves of her toned bottom. She had bright blue eyes that James could just get lost in as well as a pair of fantastic, pert breasts. They were not too small but not quite as large as her best friend Sarah, who was walking in beside her.

Sarah was just as slim as Lucy, but with the exception of an amazing pair of large bouncy breasts. They were so big that it was very difficult to look anywhere else. She was just as beautiful as Lucy, with deep brown eyes and long hazelnut hair that she liked to keep flowing loosely behind her.

As James watched them walk past, he could imagine what it would be like to have them waltz right up to him, pull the table out of the way and lean in close. He pictured having their soft lips kiss his as he caressed their flawless bodies, gripping lightly onto each breast through the thin fabric of their outfits. He imagined them slowly lifting off his shirt, having their gentle hands stroke his arms and chest, slowly making their way down to his jeans. He could see them unbuttoning his jeans, giving them enough room to venture inside, under the jeans, under his boxers, searching for an already rock hard cock.

James snapped out of it. He realised that he indeed now had a bulge forming down below. He readjusted in his chair, trying to make sure no one could see it. He did so just in time as another one of his crushes sat down beside him. Having nowhere else to sit, Jennifer, a chatty, friendly girl, placed herself next to James. Her leg brushed up against his as she sat down. He struggled to compose himself. Jenifer had fire like red hair and an amazing smile. She had a few freckles that enhanced her cuteness even more. She was a lot easier to talk to than other girls and this was one of the main reasons that James had a crush on her. A few months back she had asked to borrow a pencil and James had actually managed to have a pretty decent conversation with her. But since that day he never really got the chance to talk again and his confidence plummeted back to normal.

As she sat down, he knew he had to initiate some sort of conversation, but he just couldn’t break his nerves to do it. Fortunately, Jennifer was not so shy.

“Hey James,” she said with a bright smile. James looked up at her and returned her gesture with his own awkward grin. “You had much luck with the essay yet?” she asked.

AH! An easy question, now just say more than one word, James. 

“Uhh…. Yeah. I think I’m just about done,” he replied, almost mumbling. He always seemed to come across as unsociable and miserable, but it wasn’t intentional. There was a second of silence. He knew he had to keep the conversation going somehow. Ask her how here essay is doing! Ask her how her essay is DOING!

The moment passed. It was too late, he thought.

“Well that’s great. I’m struggling a little bit with mine,” she responded, giving a comical, over exaggerated sad expression, before returning to her lovely smile.

James tried to give an understanding nod in response. Offer to help! OFFER TO HELP!

Jennifer then turned around to talk to someone on the other side of her and was soon deep in conversation. James felt terrible. He had screwed up once again.

“SILENCE!” came a female voice from the door to the classroom. The class stopped talking immediately. Miss Marshal was at the door ready to teach. She was dressed in a tight, white, formal shirt and a black skirt. She had long black hair that was done up in a bun. She was quite a stern teacher and soon had the lesson underway.

Later, the lesson was almost over and Miss Marshal was reeling off a list of names to partner people up. These teams of two would need to then prepare for a presentation for next week.

“James and Kirsty,” she stated. James turned around. He could see Kirsty at the back of the room. She was busy texting on her phone, not really paying attention. She had short brown hair and greenish eyes.

The school bell went off and everyone started to leave. James hurriedly grabbed his stuff and tried to catch Kirsty, who was already halfway down the corridor.

“K…Kirsty,” he called out, nervously. She did not hear him. He hurried after her and when he was close enough, tapped her on the shoulder. She turned around with a look of disinterest.

“Yeah?” she asked bluntly.

“I.. I was thinking, you know, since we are doing that presentation thing…uhh… together. We should met up to work on it, maybe my place…. Or yours? Not that I’m inviting myself over. I just think we should go somewhere to work on it, if that…. If that is ok with …. With you?” He stuttered out, talking too fast to pause for breath.

Kirsty just rolled her eyes and sighed. “Can’t we just sort it all out on MyTwitterBook?” she asked. James just nodded and she walked away, leaving James alone in the corridor.

“Smooth,” a soft female voice called out, giggling. James looked around. He had thought the corridor was empty. Behind him, a tall, stunning woman was standing by one of the drinking fountains. She was in a strapless, tight fitting, red dress. It was low cut, barely covering any part of her long legs. She had bright red lipstick that matched her dress and quite long, brown, curly hair that was flowing free behind her. She was barefoot. She had flawless skin. James was mesmerised. She had deep brown eyes that were locked with James’, not looking away from him. James was stunned by her beauty, but felt too nervous to keep looking at her, choosing instead to focus on the dull ground.

He was unsure what to say.

“Sorry, Do… do I know you?” he asked. The woman just giggled. Even her laugh was lovely. James took another peek at her. She was slowly leaning over the fountain, taking a sip of the cool, refreshing water. The beautiful curves of her bottom were on full display. The dress was sliding up a bit to reveal nothing but a smooth, bare arse underneath. James’ jaw was dropped. She stood back up again and started to walk towards him, beckoning him closer at the same time. James did as she instructed until they were inches away from each other. He had to arch his neck back to look up at her, since she was tall enough for his eye level to be at her large breasts. They were just as big as Sarah and Miss Marshal's and looked like they were ready to burst right out of the tight red dress that was holding them captive.

The mysterious woman started to slowly stroke his arm. He felt chills from her touch. He was so nervous and was struggling to control the erection that was starting to begin down below.

“No, we don’t know each other, silly. I think you might have remembered me if we had.” She giggled. She leant in closer to whisper in his ear. James could smell strawberries, fresh flowers and other wonderful smells.

“My name is Amy and I’m going to make all your dreams come true, James. Would you like that?” she whispered. She then continued to linger by his ear, awaiting his response. James had never been this close to a woman. Her breasts were pressing up against his chest. He did not know how to respond. What did she mean? How did she know his name? A thousand questions were spiralling around his mind. Amy smiled her sparkly teeth and gave him a peck on the cheek, her lipstick leaving a mark. James was numb with shock, wishing she could kiss him again, just once more.

She stepped away from him and looked around the corridor, spotting a darkened classroom.

“I’ll take that as a yes,” she happily stated. She then swiftly grabbed him by the hand and led him into an empty classroom. Inside, she let go of his hand and hurriedly pulled two chairs out to face one another. She sat down in one and gestured for James to sit opposite, he did, positioning himself awkwardly, in a desperate bid to hide the bulge in his trousers. He looked up at Amy who was smirking at his nervousness.

“How many girls in that class are you wishing you could explode your cock all over?” she suddenly and bluntly asked. James was choked by the question.

“Wh… what?” he spluttered out.

“How often do you masturbate over those women?”

“I don’t really…”

“You mean you don’t wank off?”

“Well I…”

“Come on James, it’s a natural thing.” She looked over to the closed door to the room.

“Come on! Let’s do it right now!” she suggested happily.

James was shocked into silence. He didn’t know what to do. It didn’t seem to matter though as Amy was already making the choice for him, kneeling down in front of him. She started to unbutton his jeans. James fidgeted in his seat, terrified someone would walk in at any moment. Amy’s eyes went wide as she freed James’ throbbing cock. It wasn’t too grand, but it was certainly rock hard already. Amy licked her lips.

“Yum!” she giggled, gripping lightly with her had onto the shaft of his member. James stopped struggling as she started to move her hand up and down, up and down. When her hand would reach the tip of his cock, her thumb would make a circular motion on the head, before trailing back down the rest of the cock.

She started to get faster and faster.

“Oh you are such a naughty boy, James, wanking off in a classroom of all places,” she said, looking mischievous. James could hardly respond, just gasping out groans of pleasure.

“Yes! Keep going James. I want to see that hot, thick cum of yours. I want to taste it!” she was furiously pounding his cock more and more, her breasts jiggling around, giving more stimulation to James. He couldn’t believe his luck, fully immersed in the enjoyment of the experience. It wasn’t long before James was ready to explode.

“I’m… I…” he called out. Amy knew what was coming. She quickly paced her mouth around his bulging cock, submerging the head, just as streams of spunk started to launch into her mouth. She swallowed each and every load. James’ cock went numb. She started to use her tongue to clean him up. Amy then suddenly wiped her mouth and sat back down as if nothing had happened. James started to pull his jeans back up.

He sat there awkwardly, unsure how to act after what had just happened.

“So, James, I have a little gift for you.” She smiled.

You mean that wasn’t it? James thought to himself, shocked. She reached behind herself to get something. She then pulled out a small, red notebook. It had James engraved onto the front and looked quite new. He was unsure where she could have been storing that book, but decided not to question it. She handed it to him.

“Ah… thank you,” he said, confused. Amy smiled.

“Glad you like it. You see, that is one valuable notebook. But just… you know… be careful what you write.”

“I don’t understand.”

Amy took the book back off him. She now also had a pen in her hand. She scribbled something down on the first page.

“Go take a peek through that door,” she suggested with a smirk. James did, peering out into the corridor. He could see Lucy standing alone.

“She’s about to have some fun.” Amy giggled. Confused, James watched on. He saw Lucy’s hand make its way into her shorts. He could see some movement and soon enough, Lucy’s facial expression was telling it all. Her eyes closed, she was letting out some soft moans of pleasure. Leaning up against the wall, she slid down to the floor casually playing with herself. Her moans getting louder, James quickly looked away, not wanting to be caught spying.

“Why don’t you go help her out?” Amy asked slyly. James ignored the question in embarrassment.

“Why would she do that? How did you know?” James asked. Amy pointed the book towards him.

“Because I wrote it,” she explained. James took the book and, sure enough, inside was written: Lucy is about to have herself orgasm in the corridor.

“I don’t understand. What’s the catch?”

“No catch. Just a little gift from me,” Amy replied. Lucy’s screams were getting louder.

“OH YESS!!” she yelled. Amy giggled once more.

“Now, why don’t you give it a go?” Amy suggested. James took the pen. He started to write: A pizza is about to appear on the table. Amy frowned.

“No, No. NO! Don’t be so boring James, think of something better, or I might take it back.” James looked uncertain. The pizza magically appeared on the table, but Amy quickly swiped it onto the floor. Amy sighed.

“You wanted that Kirsty girl to come to your house right?” she asked.

James nodded. Well actually, it might be nice to go to her house, he thought. He wrote it down: Kirsty is going to change her mind and ask me to come over to work on the presentation.

Amy suddenly grabbed the book off him and started to write. She read out what she added.

“But when I get to the door, she is going to suddenly feel uncontrollably horny?" James looked alarmed.

“You… You can’t put that!”

“Too late.” Amy smiled. “Enjoy!” she said, before leaning in to kiss him on the lips. Her lips were so soft that it managed to calm his nerves a bit. Amy then hurriedly left the room. James was stunned to the spot from his first ever kiss, but tried to snap out of it. He grabbed the book and chased after her, but when he reached the corridor, it was like Amy had vanished.

James looked around. He could see Lucy composing herself, trying to act natural. She looked up and their eyes met. She looked embarrassed and quickly headed away. James was alone in the corridor again. He looked down at this strange new notebook of his. He wondered why Amy had chosen to give it to him, of all people. Suddenly he could hear his phone vibrating. He fumbled into his pocket and answered the phone.

“Hey, James?”

James couldn’t believe it. It was Kirsty…

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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