Timothy's Sweet Girl

(Reminder: All characters involved in sexual situations are 18+.)

CHAPTER 1:A Party To Remember!

It was a pretty average day at Brookside County High School. Timothy Townsend, the school nerd, was in the cafeteria, sitting by himself enjoying a nice peanut butter and jelly sandwich and some canned fruit punch. As he was eating his sandwich and drinking his punch, he was staring at another table 5 feet away from his table.

The table he was staring at was the popular table where the cheerleaders sat and gossiped. The cheerleaders practically ruled Brookside High and no nerd nor ugly teen dared to talk to them because the cheerleaders only associated with the jocks.

The girls sitting at the table included Tara Gaddam, Gabriella Kruger, Whitney Diamond, and Cassandra Sweeton.

Tara was a brunette from Satuli, India and her family moved to Brookside. She was already bratty to begin with but when she joined the cheerleaders, her bratty behavior grew worse.

Gabriella was a blonde that loved using her good looks to get what she wanted, especially from the teachers and nerds.

Whitney was a fiery redhead who was just as spoiled as Tara and Gabriella. She loved getting lots of attention for her sexy looks and amazing cheerleading moves.

But none of these girls could compare to the captain of the cheerleaders and most popular girl at Brookside, Cassandra Sweeton or Cassie. She was a beautiful brunette bombshell that looked similar to Madison Beer but with blue eyes. Unlike some of the other cheerleaders, Cassie was more kind and sweet.

Timothy had liked her ever since he first saw her in gym class, practicing her cheer moves. "Oh god look at her! She's so beautiful! I wish I had the courage to talk to her...no way I'd probably piss myself!" He thought to himself.

"Girls I feel like Nathan just totally ruined my confidence" said Cassie while she ate her hamburger. A week ago, Nathan Jackson, the quarterback on the football team, dumped her for another girl.

"Oh fuck him Cassie and I don't mean in the good way. There are plenty of guys on the football team like Nathan." Whitney said while looking at herself in her pocket mirror.

"Exactly!" Tara interrupted. "The best way to get over a guy is to get under another. It always works for me!"

"Ugh you are such a slut Tara!" said Gabriella while eating a banana.

"Oh you shouldn't be talking considering all the guys you've fucked!" said Whitney.

"Okay ladies heal!" Cassie said, trying to de-escalate the situation. "I think I'm done dating jocks, they are just dumb meatheads! I just want a guy who likes me for me and not my boobs or ass."

"Maybe you'll find one at your house party this weekend!" said Gabriella.

"Oh yeah I almost forgot, thanks for reminding me Gabby" said Cassie.

"OMG it's gonna be so fucking awesome!" said Tara with excitement.

"You always throw the best parties! Remember ladies dress real slutty! We need to act like our vaginas cost $100,000!" Whitney said with a mischievous smile.

"Absolutely girl! There's gonna be drinks, music, sweets, the whole shebang!" said Cassie.

As the other girls discussed the party, Cassie noticed Timothy staring at her. She smiled and waved at him and he blushed and went back to eating and looking at his book.

"Eww Cassie don't wave at that weirdo! We don't associate with his kind!" said Whitney.

"Ugh, look at him sitting all by his lonely pathetic self" Gabriella said while giggling.

"I know he is such a loser!" said Tara.

"Girls stop it, don't be mean! Actually he's kinda cute and he could be a nice guy." Cassie said while admiring his nice brown hair, brown eyes with big glasses and green polo shirt with a red bow tie.

Her friends looked at her shocked and disgusted.

"Are you kidding me Cassie?! He's such a nerd, meaning he's only good for doing our work for us!" said Whitney with a smug smile on her face and all of the other girls nodded in agreement.

"Yeah yeah I guess you're... OMG look, it's Derek Goodman!" Cassie said as she pointed at the buff black teen and all of her friends looked at him in awe and pure lust.

"OMG he is so fucking hot!" said Whitney.

"I know! I heard his dick is so fucking big! Like 8 inches!" said Gabriella.

"Mmmm I want him to destroy my pussy with his cock!" said Tara.

While they were drooling over Derek, Cassie got up and approached Timothy's table. Timothy saw her approaching and got nervous instantly.

"Hey Timothy! Whatcha doing sitting here all by yourself?" she asked while twirling her hair.

"Oh well I was just...just eating. My best friend is out vacationing on a cruise in the Indian Ocean and my other friends have different lunch times" he said while trying not to look at her baby blue skirt and crop top that barely contained her boobs.

"Hehehe nice! So what are you doing this Saturday night?" she asked while looking into his brown eyes.

"Well I'm just gonna stay in my room and watch the 2003 Daredevil movie, why?."

"Well I'm having a party at my house this Saturday night and I want you to come."

"Wow really?! Why would you want someone like me to come to your party?"

"Well because I heard you don't get invited out much so I wanted to invite you so you could have some fun!"

"Well okay sure I'll come! What time and where is it?"

"At 12 AM on Bluebird Lane, try to wear something nice, okay! See you this Saturday, cutie!" she said as she pinched his cheek walked back to her friends.

Timothy blushed and held his cheek where Cassie had pinched him. He couldn't believe what just happened and he couldn't help but stare at her tight, firm butt in the skirt as she walked back to her table.

"Oh I am so fucking hooked this Saturday night! Thank you Jesus!" he said with excitement

The bell rang and the students went to their classes. Timothy wanted the school day to be over and Saturday to begin as he was so excited about the party but he was also nervous. He thought it might be a prank but he decided to put all negative thoughts aside and think positive.

On Saturday night, Timothy was walking on Bluebird Lane, on his way to Cassie's party. He remembered what she said about wearing something nice for the party. So, he wore tight gray jeans, a red and black striped shirt, and a red bow tie. He still had his glasses on because he couldn't really see without them.

"God please let this go well please!!!" begged Timothy.

Timothy finally arrived at Cassie's house, a huge white house full of whirling neon lights and students from the school. As he approached the front door, some of the guests outside were looking at him weird, as if he didn't belong there but Timothy shrugged it off and entered the house.

When he entered the house, he discovered that her house was huge on the inside. There were probably 1,000 people there, drinking and partying. Many of the girls there were dressed up very slutty, especially Tara, Gabriella and Whitney.

"OMG Timothy Townsend is here!" said Tara as she pointed at him.

The other girls saw him and couldn't believe their eyes. They didn't want a geek at the party. They approached him and surrounded him.

"Oh sweetie you must be in the wrong place because Dorksville is way on the other side of town!" said Whitney with an evil smile.

"Yeah what's a nerd like you doing at a party like this?" Gabriella asked while holding a drink.

"Oh well Cassie invited me!" said Timothy.

"CASSIE INVITED YOU?!" said Whitney in shock and the other girls looked shocked too.

As they were processing what Timothy had said, they and the other guests heard Cassie's voice ring out from an upstairs room.

"ARE YOU GUYS READY TO PARTY WITH THE QUEEN BEE OF BROOKSIDE HIGH?! I HOPE YOU ARE BECAUSE THIS PARTY IS ABOUT TO GET FUCKING WILD! LET'S GET IT STARTED! WAH-HOO!"

Timothy looked up at the stairs and saw Cassie in a short rose pink skirt and hot pink crop top that barely covered her big breasts. She actually did a flip from the stairs and landed at the bottom in a split. The crowd cheered at her amazing moves and Timothy looked at her in absolute awe. Then, she jumped high up in the air and grabbed the pole of the disco ball and pole danced for her audience. Finally, she jumped and landed on the floor while the disco ball exploded and rained candy. The crowd cheered some more and grabbed some candy. Timothy was a blushing mess as Cassie approached him and her friends.

"OH MY FUCKING GOD CASSIE THAT WAS FUCKING AMAZING! said Whitney.

"I know but I think I went a little bit too far with the candy confetti. I think I have a rainbow in my vagina right now! OMG Timmy you made it!" said Cassie with excitement.

"Yeah I did, I mean you did invite me! That performance you did was awesome!"

"Oh thank you! You're so sweet! I know you don't get invited out much so I hope this itsy bitsy get-together can serve as a fun first time."

"This is itsy bitsy?!" said Timothy as he looked around at the huge party.

"Yeah I mean I would've thrown a bigger one but my mom wouldn't let me! So fucking lame!"

"Yeah moms can be like that sometimes. My mom almost always forbids me from doing dangerous experiments in my room because I might set the house on fire again."

"Oh wow! So you're like a mad scientist! Cool!"

"Ha yeah thanks! Wow, your outfit looks incredibly...hot!" said Timothy but he instantly regretted it.

Cassie laughed uncontrollably while her friends looked at her in shock.

"Hahaha Timothy you are so funny! You don't care how freaky you come off and I love that!

"You do?" Timothy said, confused.

"Yeah totally!" Now you just have fun, get some sweets and drinks and tear it up ow!" said Cassie as she walked off and her friends followed her but Whitney flipped him off as they walked away. Timothy was offended but shrugged it off and continued to party.

The guests at the party drank beer and ate candy, pie and cake. Timothy tried some beer but it tasted bitter to him given that it was his first time drinking one. He saw Cassie stuffing her face with pie and cake, and he was absolutely amazed by her ability to eat so fast. Her last name was kinda ironic with her predilection for sweets.

Timothy decided to go upstairs and look around a bit. As he went down the hallway, he heard loud moans in a room on the right. He went to the door and noticed it was cracked open. He looked through the crack and what he saw absolutely shocked him. He saw Derek Goodman fucking Tara in doggystyle.

"AAHHH FUCK YEAH YEAH YEAH! YES FUCK ME IN MY LITTLE HOLE!" she moaned.

"AHHH YES YES YESSSS BABY TAKE IT!" Derek yelled out.

Timothy practically drooled from watching them and started to get an erection. Suddenly, he heard a whisper in his ear.

"She is such a slut!"

Timothy was startled and turned around to see Cassie.

"Oh...hey Cassie! I was just...curious." said Timothy.

"Hehehe yeah I know! Hey, you wanna come see my room?" she asked with a little mischievous twinkle in her eye.

"Um yeah sure whatever!" he said while blushing hot red.

Cassie led Timothy into her bedroom, which was huge. It had a huge queen-sized bed and a big flat-screen TV. There were posters of Sabrina Carpenter and Usher everywhere, and the decor all had a pink motif. While Timothy was admiring her set-up, Cassie had closed her door and locked it.

"Ummm so while I really like your set-up here, why are we here?"

Cassie slowly approached Timothy and gently pushed him onto her bed, much to his shock. Then, she slowly removed her hot pink crop top, revealing her big, beautiful, breasts topped with hot tan nipples.

"Well Timothy I'm super horny but not for jocks. I'm horny for nerds like you!" she said while revealing her skirt and panties, revealing her tight, pink pussy.

"R-r-r-r-eally but why..."

Cassie silenced him by putting her finger over his lips.

"Shhhhh! Don't question it...just enjoy it!"

Cassie began to unzip Timothy's gray jeans and lowered his Spider-Man underwear to reveal a shocking surprise. Timothy's cock was fully erected and roughly 9.5 inches long. It was very veiny, had trimmed public hair and a huge, bulbous pink tip on top.

"Holy shit Timothy! You're fucking huge!" she said as she admired his big, beautiful penis.

"Yeah I am...I try not to brag about it but...HOLY SHIT!" he said in shock as Cassie started sucking his cock. She was bobbing her head up and down pretty fast with Timothy's cock in her mouth. With the combination of his huge, thick cock and her warm, amazing mouth and tongue, Cassie and Timothy were both in heaven.

"Oh..ahhhh God! Ahhh Cassie please more!" he moaned while running his fingers between her beautiful, brown hair.

"GLUCK GLUCK GLUCK GLUCK GLUCK! Ahh Timmy Timmy Timmy you taste so fucking good!" she said before she slowly licked the top of his dick and suckled his balls.

"Oh fuck! Cassie you look so fucking hot right now!" he said while looking into her blue eyes and drooling mouth.

"Mmmm hahaha oh Timmy things are about to get even hotter!"

Cassie slowly crawled on top of Timothy and inserted his huge, throbbing dick into her tight vagina.

"AHHH AHHHH FUCK YOU'RE STRETCHING MY LITTLE PUSSY OUT!" she moaned while slowly riding his dick.

"OH...OH SHIT CASSIE YOU'RE SO WARM AND TIGHT!" he said as he felt her pussy clench onto his dick and he felt her big booty with both hands.

"OH FUCK! MMMM YOUR COCK FEELS SO MUCH BETTER THAN NATHAN'S COCK!"

Cassie started riding a little bit faster, bent down to Timothy's face and grabbed and kissed him hard.

"AHHH SHIT YOU ARE INCREDIBLE!" he yelled out and slapped her bare butt.

"AHHH FUCK FUCK FUCKKK! I'M GONNA CUM ALL OVER YOUR COCK!"

As she wildly rode his cock, she started to cum on his cock. Her eyes slowly rolled back into her head.

"AHHH SHIT SHIT SHIIIT!" TIMMY I HAVE NEVER CAME SO HARD BEFORE IN MY LIFE!"

"OH SHIT CASSIE...MAYBE WE SHOULD STOP!"

"WHAT FUCK NO WHY?!"

"BECAUSE I...I.. I...AHHHHHH!"

Timothy screamed as he came deep inside her pussy. Long, thick ropes of semen hit the walls of her vagina and quickly filled her up.

"OH FUCK FUCK FUCK FUUUCK!" Cassie yelled in shock as Timothy creampied her.

Timothy's cock finally settled down and relaxed, and Cassie laid down down to him.

"Oh shit! I probably should've mentioned that I have hyperspermia." he said while taking a hard breath.

"OMG Timothy you really filled me up!" she said as Timothy's semen was spilling out of her pussy and she tasted some. "Mmmm you taste so fucking good!"

"Oh well thanks but are you on birth control?" he asked while blushing.

"Oh of course I am! Shit Timothy you are fucking incredible! The way your giant cock filled my tight little pussy and your cum filled me up more was absolutely incredible!"

"Oh well um thanks Cassie!" said Timothy with somewhat satisfaction and then he saw the clock and it was 3:33 AM. "Oh man it's late I should get home."

"Awww do you really have to go?!" she asked while Timothy was putting his jeans back on.

"Sadly yes my mom will get worried if I'm not back in the morning. But before I go I just want to say thank you for inviting me and also for riding the hell out of my cock!"

"Hehehe, you're welcome! See you Monday you mad scientist!"

Cassie hugged Timothy and kissed him on the lips again.

"Ummm...yeah you...too!" said Timothy as he blushed blood red.

Cassie unlocked her door and let Timothy out. While everyone else partied hard, Timothy snuck out of the house and as he was outside, he saw Cassie looking at him from her balcony. She smiled and waved at him. Timothy waved back but was too distracted by her beauty to realize that he was near her outdoor pool and he accidentally fell in it. The guests outside laughed uncontrollably at him.

"Hahaha what an idiot! You should've stayed at home and played Dungeons and Dragons!" said Gabriella.

Timothy crawled out of the pool in shame and ran back home. Cassie watched him leave the party and felt bad for him.

Timothy snuck into his dark room through his window and tried to go to sleep but he couldn't stop thinking about Cassie. Her kind and slutty personality amazed him. "Holy shit! I lost my virginity to Cassandra Sweeton!" he whispered to myself. Finally he fell asleep.