The Pursuit of Pleasure Ch. 01

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Disclaimer: This is my first time posting a story to this site. I really looking for constructive criticism on this piece. Truth be told, I wrote this story on a dare from my friend. I was really proud of this that I a decided to post this. I don't care what comments you have. Any comments helps me with the writing process. The reception of this piece may or may not decide if I'm going to post again or not. Anyway, here we go.

Every character introduced is a least 18 years old or above.

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You know life is funny sometimes. People have certain expectations for all different kinds of people. Especially if they see your body. People make different standards of what people should do with their lives based on what they look like. Everybody should know that they can carve their own destiny. This the story of Andre Jefferson, a 18 year old big guy with a lots fat and a lot of strength, and Annabelle Wright, a chubby girl with a beautiful English accent. They were two people that had so many hidden desires. This is a tale of two people achieving true hedonistic pleasure.

It was a cool September day in New Jersey. Teens were starting to getting back to school. Football season was starting at St. Vincent High School. The school was ready to do some great things this year for the seniors. The halls were full of laughter and cheerful energy. The nerds were talking about science club. The theater crew were talking about the upcoming talent show in December. The cool kids were talking about all the parties that are going to happen this semester. Last but not least, the football jocks walked through the halls of the school talking about going to state.

One of the jocks in particular was not as excited as the others. Andre Jefferson was one of the biggest and best linemen of the football team. He had warm almond skin and curly, brown afro. He should at 6'7'' and weighed 371 pounds. When you first think about him you'd think he'd be incredible fat, but it was almost the opposite. His most redeeming quality was his body. He did have a huge belly and a flabby chest, but that came with powerful, toned legs and arms. He was quite literally the strongest man on the football team and in the entire school.

He was always big. His father was just as big when he was in the army. He was always told by his most of his family that he should play football. He always had a quiet personality when it come to telling people how he felt. Andre wasn't as happy about doing something he was expected to do by other people.

As he walked with the jocks, he quietly breaks anyway from them and tries to get to class. Andre was a straight A student and was effortlessly smart when it came to almost every class and life. He walks into class and some of the football team fans shout out his name. He's cheeks turn slightly red and he smirks a little. He sits into his desks in the back of the class and the bell rings through the school.

Andre was just looking out at the window when the teacher walked in. Andre ears weren't quite hearing right because the usual voice he heard for his English was usually an old man. But when he turned to look he was stunned at what he saw. He saw a beautiful voluptuous blonde woman. She was a new teacher from the United Kingdom. She was majestic. Her lips were full and red like fresh cherries from an ice cream shop. She had eyes as blue as the ocean during a sunny day. Her skin was porcelain white, and had a great British accent. She introduced herself as Annabelle Wright.

Annabelle was the most beautiful woman Andre had ever seen. He estimated that she was at least 250 pounds at 5'8''. Andre's pants all of a sudden got really tight around the crotch area. Everyone noticed that she was fairly young to be a teacher.

"Hey Ms. Wright, aren't you about a little young to be a teacher." said a random boy in the classroom.

Ms. Wright responded,"Yes, I know. I'm 20 actually. I graduated from college early in London because of my intellect and academic achievements. I'm on a work trial period where they want to test my skills as an instructor. It only for 3 months until they make a decision whether they hire me or not. I will be paid for my time though. But my only goal is to do the best I can to help some of you seniors get your grades up so you all can participate in the activities you all want to do ."

"So does this mean homework on the first day?" said Patrick Reeves, one of the football jocks.

Ms. Wright laughed to herself. She had such a beautiful smile. She said to Patrick, " No, sir. But we will be taking some notes."

The whole class sighed as Annabelle started the lesson for today. This went on about 3 weeks. After all that time, they had a exam about Romeo and Juliet. As the quiz went on, Annabelle noticed that Andre wasn't writing anything on his paper. Instead, he had a smile on his face as he looked out the window. But instead of looking at the sky he looked at Annabelle's reflection in the mirror.

Andre was admiring Annabelle's body. Her breast were a about the size of oversized water balloons in the summer. They were a great size. Her legs were plump and looked as soft as marshmallows. They looked delicious. Andre thought the highlight of her body was her huge ass. He estimated that it was a least 65 inches of pure meat. Andre felt a twitch in his crotch because his dirty thoughts. He was too happy to care. Annabelle ended the test and then the bell had rung about 5 minutes after then. As everyone walked out, Annabelle called out Andre to ask if he could come to her class after school. He agreed very easily and eagerly. The rest of the school day was just making him more eager to see Annabelle after each passing moment.

At lunchtime, Andre went to the library to talk his childhood friend, Mateo. Mateo was a Hispanic guy that was pretty short compared to Andre. That didn't stop the two from becoming friends. Mateo was 5'3'', about 130 pounds, and had really skinny frame on him. Andre and Mateo grew up together liking almost everything each other liked. They meet at summer camp when they were about 9 years old. They shared the same taste in food, music, hobbies, and especially women.

Mateo may be short be he loved to a woman bigger than him please a shorter guy. Mateo said he has a bit of an Oedipus complex. He liked women that were like his mother. She was happy being fat no matter what anyone said. That is probably why him and Andre got along so great. He knew how Andre felt. Mateo's mother made Annabelle look like an anorexic supermodel. Mateo said she hit 700 pounds last year.

"Hey, Andre. How was your first class?" Mateo asked.

Andre stumbled a bit. He was a little embarrassed that he liked Annabelle.

"Uhh..... My new teacher is.... the most beautiful woman I've ever met." responded Andre.

"Which teacher we talking about?"

"Ms. Wright."

"Ohh yeah. I saw her in the hallway. She had great tits and an ass to match."

"Yeah, dude .... She's the first woman my eyes ever really jumped out at."

That statement had so much truth to it. All the girls at school were too skinny for Andre. Except for maybe a few really big girls that were mainly some the outcasts in the school.

"And she asked me to come after school" Andre added.

"Holy shit! Why?" Mateo asked.

"I don't know maybe she wants to talk about me not paying attention in class. The only person I can focus on clearly is Ms. Wright. With her.... Everything is just so perfect. "

"Damn, you going to ask her to marry you? Mateo joked.

"Mateo, I've never felt this way about any other girl in my life. I would drink my own piss if I could even get a date with her." Andre said.

"Dude, you have it bad."

"I got a hard on when I first say her and every time I'm in that classroom. I'm glad I'm not wearing sweatpants today."

"What if she weighed more than what she is now? Say about 200 more... What would you do?"

"I'd probably masturbate at least four times a day if I even think her even gaining 50 pounds."

"Andre, I get it. You have any idea how long I been wanting a woman that looks like my mom? I want to love someone like my dad loves my mom. Look, we graduate high school in May then after that you have a huge chance." said Mateo.

"Mateo, I don't know if I can wait that long. I still can't stop thinking about her."

"You got this, man. I know school can't possibly last that long."

Mateo ended up reassuring Andre for the rest of the day but when he meet up with Annabelle after school something happened that he didn't expect.

"Andre, I noticed that your weren't paying attention during class for the first few weeks." said Annabelle

"Uh..sorry. My mind was a wandering all over place lately. I meant no disrespect," said Andre.

Annabelle smirked and said," Andre, you're fine. It just you have a big smile on your face when you daydreamed. I only wanted to ask what you were thinking about that made you happy."

Andre stumbled, "Umm... Actually... I was thinking-----"

So many dirty thoughts ran though Andre's mind and he did something he didn't think he would've done. Annabelle moved closer to Andre. Then he kissed her. Annabelle was incredible shocked, but she didn't try and fight it. She even used her tongue. She tasted liked honey and apples. It felt like an eternity of pleasure for the both of them. Andre almost instinctively felt up her ass and her belly. He felt her nipples on his soft yet firm chest. The way Andre's belly felt on her belly had them both happy to be with each other. They were both incredibly aroused. Annabelle's pussy was too wet for words and she felt Andre's dick on her thigh.

She was happy to feel Andre's strong veiny arms. The pulsating from Andre's dick felt unbelievable to Annabelle. The kissed last a good 5 minutes until they realized what they were doing. If the kiss lasted any longer, Annabelle's pussy would've have become a juicy waterfall by 6 minutes.

Andre realized what he did. Annabelle was as red as cherry. Andre was only scared and afraid. Truth be told, that was Andre's first real kiss. Annabelle was surprised how well he did. Andre walked out of the room and hurried to football practice. Annabelle tried to stop him, but she was too late. Andre went through football practice angry and a little sad.

When he got home, he masturbated furiously to the image of Annabelle. His dick was red and purple from how pent up he was. He needed some serious relief. He couldn't help it. It was his first kiss. Not many woman like a heavy set man like Andre. That the reason why he doesn't date at all. He was only mad because he felt that any chance of a some type of relationship with Annabelle would be impossible because of what he did. He had to get her old of her head. He went online look up something he could jerk off to. He tried some real heavyweight women websites that he often visited but it didn't work as well. Andre finally faced the fact that he was in a slump.

Two months passed after the incident in after school. Annabelle treated Andre as if nothing happened after the first day. Andre was really depressed. His usefulness on the football field did improve though. Mateo even failed at cheering him up. Every night he went straight to bed after practice. He really didn't feel like doing anything. He even gained about 10 pounds because of his depression. He ate just about anything and everything from celery to deep fried jumbo shrimp dipped in butter.

The big homecoming game was coming up real soon and he really didn't feel like coming. The team needed him to win. He gives foundation to the linemen. Just when he was about to give up. His grandmother decided to talk to him. Andre's grandmother was a big Jamaican woman with a huge body. She was Andre's caretaker after his mother died of cancer and his father died in the army.

"Andre, is everything alright?" said his grandma.

Andre finally confided in someone in an anonymous way.

"Grandma,..... what if you saw someone you loved and you knew you couldn't be together." said Andre soft spokenly.

"Baby boy, no one ain't good enough for you. Sometimes, I think you're too good for other people. All that matters is that you're both happy and love each other."

"Grandma, how do you know that?"

"Because your mother and father loved each to the point of death. And so did me and your grandfather. I know he loved the way I looked, and the way he treated each other was so magical."

That really resonated with Andre. He missed his mother and father so much. That statement alone cheered him up a lot. He decided to go to the game after all.

"Thanks, grandma." smirked Andre.

He kissed his grandma and then went to bed. He still thought about Annabelle that night but it wasn't that bad anymore.

The next 2 weeks went by and the homecoming game was starting in 6 hours. One of the outcast girls that Andre didn't really talk to walked up to him and tried to ask him something. The girl tapped him on the shoulder and asked him something during lunch in the library. Andre turned around and saw a beautiful girl.

She looked as if she was an Asian. Her skin was a pale brown. She had a great smile and her hair was brown. Her breasts were the size of soccer balls. They looked they haven't been touched by anyone in her life. Her belly was colossal. It hung from her abdomen to her mid thighs and it looked so soft. It had two huge rolls. Her ass was wider than most of the chairs in the library. Andre knew for a fact it was bigger than his and Annabelle's. Her ass was almost a shelf. It had some definition to it. She was 457 pounds at 5'5''.

"Um..Hi, Andre. My name is Olivia," said shyly Olivia

"Hey,.... whatcha need?" responded Andre.

"I know you don't know me that well. But I'm in your health class. .... Um.. well.. I was interested in you and I wanted to know if you wanted to get to know me better."

Andre was dumbfounded. He didn't a beautiful like her to ask him out and he had gain few more pounds these past two months. She was blushing red at what she said.

"Yeah... Yeah... sure." Andre said very willingly.

"Great, here's my number. Call me when you wanna talk or hang out."

"Yeah, that's great."

"Awesome!" she shouted.

Everyone in the library looked around to where the noise came from and she was a "cherry" by that point in the conversation. Andre only could smile at her. She was as jolly as Mrs. Claus after eating fresh cookies and milk. Andre was a happy to have finally moved on from Annabelle. School ended early for the homecoming game. Andre was at his locker and then he ran into the bathroom really quick to pee. It was empty. He went into a stall so he wouldn't be recognize in case someone came in.

As he urinated, he heard the door open. He was finished peeing by that time. When he came out, he look up and it was Annabelle. Only thing was she gained some weight on her. Andre hadn't been paying attention to her in class so he never really noticed her figure. It was almost impossible how much weight she had now. She was 352 pounds.

She walked up to Andre, who was as blushing hard right now, and she kissed Andre. She started to use her tongue. She was wild and she wasn't stopping anytime soon. Andre didn't even try and stop her. He loved every second of it. Before that, she locked the door so no one would come in. Then, she unzipped his pants while they were they both were still kissing. She stopped the kiss and drop his pants and underwear all the way done to his ankles and she pulled out Andre's dick. It was red with pumped up blood and purple with so many veins ready to go. She was even shocked at how big Andre was. It was a whopping fifteen inches long and had the girth of a water bottle.

She licked her sweet lips and gave it a small lick at the dick's head. Andre squealed like a pig. She could tell he was close already at this moment. All she could do was look at Andre face and told him,"Call me Annabelle from now on," with a huge grin and tears down her face. She tooked his dick in her mouth. Andre cummed so hard he fell back into the wall. Annabelle was so shock that his orgasm was so powerful.

His cum was so thick and it shot into her mouth very quickly. It was so quick that cum came out of her nose. She was embarrassed, but Andre laughed at little at her. Annabelle was so red with embarrassment and a little anger that she teased him. She put her lips on Andre mouth and gave him his first blowjob. She put herself in a 69 position with Andre and after 3 minutes was already hard again and ready to cum. However, he wasn't the only one.

Andre had licked Annabelle's crotch even when she had her white lace panties. She came at least twice just from a sniff and a lick from Andre. He was at his breaking point and she already keep licking him. When she felt such strong pulsations from his dick. She all of a sudden stopped. Andre made a face as if he ate the sourest of the lemon in the world. She let go of his dick and turned to him. She lied next to him . He was still ready to blow with the most simple of touches.

"Did you enjoy that? I know I did." Annabelle whispered.

Andre nodded.

"Here's my address and number. Come to my house after your game or before. Text me to tell me you're coming, ok? I have something to show you and give you."

Andre nodded with a clueless look on his face. Annabelle went to hug him.

"I just wanted to give a little good luck for your game. I want you to use your pented up energy and anticipation for tonight to win. Oh and by the way, I love the extra weight on you."

She flashed him her breasts before she left. Her areolas look beautiful. Andre was trying so hard to make sense of what happened. Just when he moved on, he caught up with Annabelle again. He left the bathroom and ran into Patrick in the hall.

"Hey, Andre. Where were you, man? Our game meeting is about to start soon." said Patrick.

"Um, just took a huge dump in the bathroom." Andre lied to him.

"Damn. That must have been one huge dump. Anyway, let's get to the meeting. I don't want you get yelled. You're actually one of the fews guys on the football team that are actually nice."

"Thanks, man..... If I being perfectly honest with you, this might be my last game for high school."

"Really, why?"

"Football just isn't that interesting at all to me. I just did this 'cause I was pressured. Plus, things have been starting to get stirred up in my life."

"I get you, man. And most of the people on the football teams are pretty much assholes. I just might quick, too."

"Thanks for understanding. You're a good friend, Patrick."

"So are you, man."

Patrick was a stout man just like Andre. He was 6'1'' at 257 pounds. He had lots of muscles on him, too. The only difference between and Andre is that he was Caucasian with pale skin and he had a bread. They hurried to the meeting and not soon after the game had started.

Andre had so much excess energy on him from his encounter with Annabelle. He was so excited for tonight. The whole team played hard and they ended up winning. Andre notified the coach about leaving the team. Patrick joined him and they left together. The coach was a little bitter when they both left. The whole team tried to protest this. They both were the foundation of the team's defense. Although, Andre and Patrick ended up laughing as they left.

Patrick asked if he wanted to hang out tonight. Andre had to turn it down. He said he had "something" to do tonight. Patrick said anytime he wanted to hang out he'd be there for him.

It was 12am in the morning. Andre drove to the address Annabelle gave him. He was so nervous. He was starting to shake in anticipation. His cock was throbbing and he sweating pretty hard. He got out of the car and walked to the door. He rang on the doorbell. It was a few minutes before Annabelle answered. She wearing a very tight white dress and red lipstick. She waddled to Andre and kissed him. His cock was sticking out of his sweatpants. She was tongue wrestling with Andre for 5 minutes until she said "come in."