Timothy's Sweet Girl

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

CHAPTER 2:Missionary Monday

On a Monday morning, Cassie and her friends were sitting at their normal table, enjoying breakfast in the school cafeteria. Her friends were talking about her party last weekend while she was looking at Timothy sitting alone at his normal table and remembering the wonderful night they had.

"Tara I can't believe you had sex with Derek Goodman!" said Gabriella.

"Me neither! So how did his dick feel?!" Whitney asked while eating a piece of sausage.

"OMG it felt sooo good! His dick was like 8 inches and it completely stretched out my pussy! He pounded me so good and I think I came like 10 times!" said Tara.

"Hehehe that's crazy! Also I heard you got lucky Cassie!" said Whitney. "Um hello Cassie?!"

"Oh I'm sorry you guys say something?" asked Cassie.

"Yeah Kendra told us that she heard you getting fucked!" said Whitney.

"Well actually I fucked him and by that I mean I rode the shit out of his cock!" said Cassie with excitement.

Her friends looked at her in shock and happiness.

"Oh my God who was it? Was it one of the football players?" asked Tara.

"Oh I'd rather not say but this guy's dick was like 9.5 inches, way bigger than Derek's dick!"

"Well shit that guy sounds fucking hot! It makes me wanna find him and fuck him too!" said Whitney with jealousy.

"Well, find your own sweetheart because that one is mine!" said Cassie.

While her friends continued to talk about the party, Cassie continued to stare at Timothy. Timothy noticed her and waved to her. Cassie waved back, grabbed her sausage and gave it a blowjob to tease him. Timothy blushed and started to get an erection while remembering the blowjob Cassie gave him. The bell rang, signaling the students to go to their first classes. Some of the students stayed in the cafeteria for a while and some of them including Timothy went to their first classes.

Hours later, Timothy and his good friend Abel Diamond (Whitney's younger brother that had red hair, freckles and gap teeth) were in gym class, sitting on the bleachers.

"So Tim, is it true Cassie Sweeton invited you to her party?" asked Abel.

"Yes it's true, but something incredible happened at that party and you have to promise you won't tell anyone about it. This stays completely between us."

"Okay okay! What happened?!"

"I lost my virginity to Cassandra Sweeton!!!"

"OH MY GOSH! YOU HAD SEX WITH CASSIE SWEETON!!!" said Abel with excitement.

"Shhhhh you idiot! People are gonna hear you!" said Timothy but luckily no one heard him.

"Sorry sorry sorry! So what was it like, man?!"

"Oh god it was amazing! She rode me cowgirl style and her vagina was so tight! I've never came so good in my whole life!"

"Oh god you are fucking lucky she invited you to her party!"

"HEY TIMOTHY AND ABEL! GET OFF THE BLEACHERS! WE'RE GOING OUTSIDE TO RUN LAPS!" said the coach.

Timothy and Abel got off the bleachers and followed the coach and their fellow classmates outside. They and the other students raced to the track and began running.

Meanwhile, Cassie and the other cheerleaders were on the football field right next to the racetrack practicing their moves.

"NOWHERE TO RUN, NOWHERE TO HIDE, WE'RE THE SCHOOL THEY CALL BROOKSIDE!" the cheerleaders chanted as they performed a pyramid with Cassie on top.

They stopped to take a quick break and Cassie saw the guys running on the track. She especially had her eye on Timothy who was jumping hurdles quite fast. Despite being a nerd, Timothy was actually quite athletic and Cassie was impressed.

"Damn Timothy is a fucking pro on the track right girls?" said Cassie.

"Are you kidding me? He's not as impressive as Derek or Nathan! He's still just a nerd!" said Whitney.

"Seriously Whitney what the fuck is your problems with nerds? Sure maybe some of them aren't athletic or attractive but some of them are sweet and smart!" said Cassie.

"Yeah but they're also no good in the bedroom!" said Gabriella.

"Yeah I beg to differ!" Cassie whispered and continued to admire Timothy.

On the racetrack, Timothy sat down to take a water break and as he was drinking his water, he saw Cassie in her blue and white cheer outfit, looking at him from the football field. He waved to her and she waved back smiling. Then, while the other cheerleaders weren't looking, Cassie did a split and shook her pom-poms. Finally, she took the end to one of her pom-poms and stuffed it into her pussy while doing an ahegao face.

Timothy was turned on by Cassie's teasing behavior and he accidentally spilled some of his water on himself. Then, he went back to running while Cassie went back to cheerleading.

At 3:15 PM, school was over and all of the students rushed out of the school and into the school buses or their cars. Cassie was walking out with her other friend, Kendra Nottingham, a beautiful blonde girl.

"So Kendra did you tell Whitney, Tara, and Gabriella that I got lucky at my party?"

"Well yeah I was wandering around in your hallway and I could hear you screaming and some guy moaning!" said Kendra.

"Well about the guy um do you know Timothy Townsend?"

"Yeah, he and Whitney's brother, Abel, have the same class as me." said Kendra.

"Well I invited him to my party because he's kind of a recluse and I may have a bit of a crush on him. But, anyway I took him to my bedroom and we had sex!"

"OMG YOU FUCKED TIMOTHY TOWNSEND!!!" said Kendra with excitement.

"Shhhhh people are gonna hear you!" said Cassie but luckily no one heard her.

"Sorry sorry sorry! So what was it like with him?!" asked Kendra.

"Oh my God it was amazing! His cock is like 9.5 inches, you could play horseshoes on that thing, and it totally stretched me out! And also he has hyperspermia and he filled me up real good when he creampied me!"

"Oh sweet Jesus he sounds fucking amazing!" said Kendra.

"I know but imagine if Whitney, Tara, and Gabriella found out about it, they would totally freak out!"

"Oh fuck them! They can be bitches sometimes! If you want my advice, maybe you should consider going out with Timothy." Kendra said while chewing on some bubble gum.

"Yeah maybe you're right. I'm so tired of dating shitbags like Nathan. I just want a guy who's gonna treat me right and likes me for me."

"Well then get to know Timothy better and see what he's all about. Maybe he's the one for you!" said Kendra.

"I think I will! Thank you so much Kendra!" Cassie hugged Kendra and then saw Timothy heading towards his bus. "Oh sorry girl gotta go! See you tomorrow!" she said while heading towards Timothy. "Hey Timothy, wait up!"

"Oh hey Cassie how's it going?"

"Oh it's going good! Hey, you wanna go for a ride with me?" Cassie asked while twirling her dark brown hair.

"Really...why?"

"Well because at my party last weekend I feel like I didn't really get to know much about you, other than your cock! So I thought it would be nice if the two of us hung out today and got to know each other better, so what do you say?"

"I say... let's ride baby!" Timothy said with a big smile.

"Yay let's go!" Cassie said as she grabbed Timothy's hand and pulled him next to her.

Timothy was excited but still a little nervous as he held Cassie's hand in the school parking lot. Some of the other students were staring at them as they walked by.

"Um Cassie everyone is staring at us."

"I don't care, let them watch."

The odd couple arrived at Cassie's car, a pink dodge challenger.

"Wow, nice car Cassie! I've never seen a pink dodge challenger before."

"Thank you! It cost my mom a bit of money but I just love the color" she said as she clicked the car alarm on her pink keychain and unlocked the car doors.

Timothy got in and put on his seat belt. Then, Cassie got in and drove off a little too fast for Timothy. Thankfully the road was empty.

"Hey you forgot to put on your seat belt!" Timothy said, absolutely terrified.

"Don't worry Timmy, I know what I'm doing!" Cassie said while continuing to drive recklessly.

After 10 minutes, they pulled up at a place called Sweeton's Palace.

"Oh cool I love this place! They have the best desserts!"

"Hahaha I know! Me and my friends love this place too, especially Tara, Gabriella and Whitney, since they think they don't have to pay for anything since I work here."

"Wow you work here?" he asked as they got out of the car.

"Yep but it's only part-time. My mom owns the place and makes some of our best sellers. She wants me to work in the family business but I only have my job to earn money and help my mom out." she said as they walked towards the place.

"So what do you want to be when you're older?"

"I'm not exactly sure. I'm kinda torn between being a singer and an actress."

"Hehehe well I bet you'll be great at either one of them."

Cassie blushed at Timothy's comment. As they entered the place, the smell of baked goods and sweet candy hit them in the nose. It was kinda a combination of a bakery and a candy shop, with all kinds of cakes, pies and other baked goods and great candies on the shelves. Cassie and Timothy saw a table next to the window with assorted gourmet lollipops and sat in the colorful chairs at the table.

Elsa Sweeton, the owner of the place and Cassie's mom, approached their table and took their order.

"Hey sweetie, what would you and your friend like?"

"Well mom, me and Timothy will have the cinnamon cream cheese roll-ups! Sounds good right Timmy?"

Timothy was distracted by Elsa's beauty and her resemblance to Cassie. Now he knew where Cassie got her good looks from. But when Cassie snapped her finger at him he snapped back to reality. "Oh um yes! Sounds delicious!"

"Hehehe great! They'll be ready in a few minutes." Elsa said with a smile and walked away.

"What happened Timmy?"

"What are you talking about?"

"Oh don't play dumb with me! You couldn't stop staring at my mom."

"Oh I'm sorry Cassie! She just looks so much like you. Now I know why you're so beautiful!"

Cassie blushed and smiled from Timothy's compliment. "Awwww you're so sweet!"

Timothy blushed as well. No girl had ever been that nice to him. He had to pinch himself to see if he was dreaming but he wasn't.

"So um Cassie, why were you teasing me at breakfast and in gym class?"

"Because I like you and I know you've had a crush on me for a long time and sometimes you've got to play around a little to make them want you even more, or at least that's what Kendra taught me."

"Kendra? Isn't she one of the cheerleaders?"

"Yes she is! She's my best friend. She's pretty sweet but wild and slutty when she wants to be. She also has a sweet pair of tits. Those things are all natural! She's like a small town version of Sydney Sweeney!"

"Oh wow she kinda sounds like you!" said Timothy.

"Hahaha yeah I'm kind of a freaky girl too when I wanna be.

"Hey it's okay to be a little freaky!"

"I know that's right! You know this one time I saw my step-dad with his shirt off and I was like "Oh my gosh you are so hot" but then I wanted to die because it was so embarrassing because he's like my dad but not really my dad so I guess it was fine. But then again I could hit that!"

Timothy was a little weirded out by her story but giggled because Cassie was kinda like him in a weird, freaky way but more popular and beautiful.

"You wanna hear something kinda naughty?!"

"Um sure! Let's hear it!"

"Well after my party ended, I couldn't stop thinking about you and your huge dick, so I played with my pussy!" she whispered.

"You masturbated to the thought of me?" he whispered back.

"Yep and I tasted myself and I tasted so sweet and salty with your cum mixed in!" she whispered.

Timothy blushed blood red in his cheeks and started to get a boner. Finally, a waiter brought their roll-ups to their table. The roll-ups were coated in granulated sugar and ground cinnamon, and had cream cheese filling in the middle.

"Wow these things look great!" said Timothy.

"I know I love these things!" said Cassie as she took a bite out of one. "Mmmm my God these are so fucking good!" she said while chewing. Her moans reminded Timothy of the moans she made when they had sex for the first time.

Timothy grabbed one and took a bite of it. The taste made his eyes twinkle. "Oh god these are amazing!" he said while chewing.

"Mmmmm I know! I especially love the cream cheese filling that hits the back of my throat as you bite into them!"

"Yeah I kinda like that too!"

20 minutes later, Timothy and Cassie finished their meal and Timothy paid for it. They went back outside and got into Cassie's car and drove off.

"So I met your mom and heard about your step-dad, where is your biological dad?" asked Timothy.

"Well my mom and real dad had some problems and about 2 years ago, they got a divorce and he left Brookside."

"Wow I'm really sorry to hear that. My parents got divorced too. I mainly live with my mom but my dad still sees me at times. "

"Oh okay! So what's the deal with you? You're the smartest guy in school, you're kind of athletic and you have a big dick, why?"

"I don't know how to really answer about my big penis, I guess it's just genetics."

"Well it's good to have a big cock but you gotta know how to use it."

"That's true. I wasn't very agile until I met Henry Miller."

"Oh yeah I've heard of him. He's the toughest guy in the school."

"Yeah I know! He actually taught me how to fight."

"Oh well he's a great friend!" she said as turned onto a street called Dixon Lane.

"He sure is! So what is it about nerds that you love so much?"

"Well they're smart, kind and their shyness is so cute to me! Besides, I'm so tired of dating dumb jocks like Nathan!"

Oh yeah I heard that he broke up with you for another girl. I'm really sorry that happened to you."

"Oh it's fine. I don't even know who the other girl is. He never even told me, he just said I don't do enough for him!" she said on the verge of crying.

"It's okay Cassie don't cry! You're a great girl who is beautiful, fun and smart! If he left that for someone else then he's fucking stupid!"

"Wow thanks Timothy! I really needed that!" she said while sniffling and continuing to drive.

Cassie stopped her car at Timothy's house and Timothy got out.

"Well thank you so much for this lovely evening Cassie!"

"Wait Timothy can I come in for a while?"

"You want to come into my house?" Timothy asked, surprised.

"Well yeah, your parents aren't home right?"

Timothy shook his head, "no, they're at work."

"Then let me come in please!" she pleaded with flaunting her blue eyes.

Timothy ran to the door and held it open for Cassie "Okay come in madame!"

"Oh thank you! You're such a gentleman!" she said as she entered his home.

Timothy and Cassie entered Timothy's room and Cassie looked around in absolute shock. He had all kinds of gadgets, machines and chemicals he had invented from the past, like a time machine, a shrink ray and a neon green growth serum. He was also into the usual nerd candy, like Star Wars, anime, and comic books, and he also had posters of Scarlett Johansson's Marvel character, the Black Widow, on his wall.

"Wow this is amazing! You're like a real actual scientist!"

"Oh thank you! Most of my lab equipment I got from school and the other stuff I'd rather not say."

"That's awesome! You seem to really like Scarlett Johansson!"

"Oh yeah she's really hot, especially when she played the Black Widow!"

Cassie wandered through his room and grabbed the neon green growth serum. "Woah what is this stuff?" she said while holding it.

"Oh that's a plant growth serum I made last year."

"This is so fucking cool? How did you make this?"

"Oh I just used some nitrogen, phosphorus, potassium, auxins and some bioluminescent algae to give it that green color!"

"Wow! Where did you get that kind of stuff?!"

"I'd rather not say!"

"You know you're an interesting guy Timothy!"

"Really?! Most girls think I'm boring because I do this kind of stuff."

"Well I'm not most girls! I think smart guys with big brains and big glasses are kinda cute. Also their innocent minds make me want to corrupt them!" she said while scratching his cheek.

"Oh that's...um interesting!" he said while sweating and blushing.

"Hehehe you're so cute when you're nervous!" Cassie moved her polished black fingernails down to Timothy's chest and towards his pants and she felt his huge erection. "Oh someone's got a boner!" she said with a mischievous smile.

"Oh...yeah it's just you're so hot in your cheer outfit!"

Cassie giggled and laid down on her back on Timothy's bed. She pushed her top up to reveal her big, beautiful breasts topped with those same hot tan nipples. She also took off her panties and spread her legs to reveal her tight, pink pussy.

"You wanna fuck the queen bee in missionary?" she asked while looking deep into his eyes.

Timothy nodded and quickly took off his pants, revealing his fully erected penis.

"Fuck are we really gonna have sex in my room?!"

"Hehehe yep! Now come here and give me that cock!"

Timothy slowly approached Cassie, climbed on top of her and slowly inserted his huge cock into her pussy.

"Oh...shhhit! Mmmm you feel bigger than last time!"

"Oh...God you're still tight as can be!" he groaned.

"Mmmm yeah! Now buck your hips and push that dick deeper into my vagina!" she whispered in his ear.

Timothy followed Cassie's instructions and started going in and out of her pussy. The heat from her breath was fogging up his glasses.

"Aww fuck...shit should I take off my glasses?"

"Hell no! Keep them on, it's hot!"

Timothy continued to pound her pussy and hugged her as he went deeper inside her.

"Awwww fuck! Yes yes yessss keep drilling your cock into me!"

"Awwww yes yesss! You're so fucking tight" he moaned while still pounding deep into her and licking and kissing on her nipples.

"Oh fuck fuck yes yes lick my little titties!"

"Mmm yeah! Am I better than Nathan at this?!"

"Yeah yes yessss! Fuck I'm cumming!"

Cassie came on Timothy's cock and grabbed his head and kissed him on the lips.

"Oh fuck Cassie you're fucking incredible! Shit I could do this all day!" he yelled as he pounded her so hard that her breasts shook.

"Oh God! YES MORE MORE MORE! FUCK I'M CUMMING AGAIN!" she yelled as she came on his cock again.

After hours of hot missionary sex, Timothy felt that his penis was about to burst with cum. He let go of Cassie and took his cock out jerking it wildly.

"Shit Cassie I'm gonna fucking cum!"

"Oh yeah?! Do it! Cum all over me! Make me your dirty cum slut!" she said while getting on her knees.

"OH GOD CASSIE! MMMM IT'S COMING!" he groaned while stroking his cock.

"Let it out, Timmy! Shoot that gooey mess all over me! Those cinnamon cream cheese roll-ups weren't enough, I want more cream!"

With a sharp groan, Timothy finally came on Cassie. The first huge rope hit her face, ruining her makeup and another blast came out, hitting her breasts. Three more ropes of semen blasted from Timothy's cock, landing on Cassie's stomach, shoulders and even her beautiful, brown hair.

"Oh shit! Wow, that was incredible!" Timothy said while breathing heavily and laid down on his bed.

"Oh Timothy you are fucking greatest nerd I've ever met!" she said as she crawled back onto the bed, laying next to Timothy.

"Really I am?"

"Yes absolutely! No guy has ever made me cum twice!"

"Well I'm glad you enjoyed it! Your vagina is absolutely exquisite!"

"Hehehe thanks! Hey um this is probably gonna be a little sudden but um-"

Cassie was interrupted by a woman's voice coming from the living room. "...honey? Are you home? Are you okay? Whose car is that outside?"

"Oh crap! It's my mom, she must be home from work early."