Timothy's Sweet Girl

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

CHAPTER 3:A Date And Doggystyle

On a warm Tuesday morning, Cassie was searching in her closet for a nice outfit and finally after a few minutes, she decided on some tight blue jeans, a white short sleeve shirt, and pink leather boots that were lifted to her knees. She applied some hair gel to her hair to make it more shiny and applied a bit heavier lipstick than usual. She wanted to look hot and she wanted to look hot for Timothy.

"Damn I look good! If I was a guy I would totally fuck me. Timothy's eyes are gonna pop out of his head when he sees me!" Cassie said to herself in the mirror.

Cassie was absolutely excited to see Timothy at school again. There was something about him that she loved and it wasn't just his massive cock. It was his intelligence, his cute nerdy look and his kind and shy attitude towards her. The jocks that she had dated and/or hooked up with including Nathan only liked her for her looks and status as the popular girl. But Timothy treated her like she was a person and listened when she talked, and Cassie loved that about him. She actually wanted to ask him out but that would probably ruin her reputation and status among the popular crowd but she didn't care.

At 8:20 AM, class began and Cassie and Timothy rushed to their same history class and sat down at their desks.

"Okay students settle down! Now today we are going to be learning about the history of the Mexican-American War and now please take out your pencils and notebooks." said Mrs. Lee, the history teacher.

Mrs. Lee was a beautiful Asian woman with a tight body and all of the male students loved her and couldn't help but stare at her.

While Mrs. Lee was talking about the Mexican-American War, Timothy was writing down the notes but got distracted when he noticed Cassie's sexy outfit. He also noticed that she wasn't wearing a bra under her shirt.

Cassie noticed that Timothy was staring and waved at him and blew a kiss at him. She also played with her nipples a little bit to tease him.

Timothy's cock got bigger in his pants and his cheeks blushed blood red. "Fuck I wanna tittyfuck her!" he thought to himself.

"Hehehe it's totally working! I bet he wants to tittyfuck me. Oh that would be so hot!" Cassie thought to herself.

Hours later, lunch began and the students flocked to the cafeteria, which was serving mini hot dogs and french fries. Timothy was sitting by himself as usual while Cassie and her friends were sitting at their usual table.

"So Cassie word has spread that you were walking with Timothy Townsend and holding hands with him yesterday, is that true?" asked Whitney.

"Yeah Whitney! I was just giving him a ride home." said Cassie.

The girls were shocked except for Kendra.

"Cassie, you seem to like Timothy, why?" asked Tara.

"Well Tara he's sweet, smart and he has like a science lab in his own room!"

"Oh my gosh you were in his room?! Did you two have sex?!" asked Gabriella.

"No, he just showed me around and I met his mom."

"Look Cassie, you need to stop hanging out with him! He's a nerd and he'll ruin your reputation and mine!" said Whitney.

"Look Whitney, you can't tell me who I can and cannot hang out with okay!"

"Hey I'm just trying to look out for you!"

"No you're not! You guys are trying to control her! You bitches are toxic! Toxic like a scorpion!" said Kendra.

"Shut up Kendra!" said Whitney.

"No she's right! You need to shut the fuck up Whitney! I can hang out with whoever I want and don't forget I'm the cheer captain, I could have your slim ass replaced in a second!"

Whitney wanted to say something back but just remained silent.

Then, Cassie saw Timothy at his usual table and picked up her tray and got up from the table.

"Well see you ladies later!"

"Where are you going?" asked Gabriella.

"I'm going to sit over there with Timothy today." Cassie replied.

"Cassie, if you go over there with that dork, consider your friendship with us over!" said Whitney.

"Fine! Honestly I didn't really like you bitches anyway. Kendra, do you wanna come with me?"

"Absolutely girl! It's definitely better than sitting with these dumb cunts." said Kendra.

Cassie and Kendra walked away from the popular table and Cassie flipped them off as they left, leaving Whitney, Tara and Gabriella shocked, and some of the other cheerleaders laughed.

"Hi Timmy!" Cassie said, setting her lunch tray next to him.

"Oh, uh hi Cassie! Why aren't you and Kendra at the popular table?" asked Timothy.

"Oh I'm done with those skanks! They see you as a loser nerd but I think you're a wonderful guy to hang out with!"

"Thanks Cassie!" he said while smiling and blushing.

"Oh you two are fucking cute together!" said Kendra.

"Thanks Kendra!" said Timothy.

"So Cassie told me about how she rode your huge cock!" said Kendra

Timothy blushed even more, "Oh gosh you told her?!"

"Well yeah! I told you she's my best friend! Oh and also yesterday he fucked me so good I came twice and he came on me pretty little face!"

"Holy fuck that's hot!"

Timothy was a blushing mess and just kept eating his mini hot dogs.

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 Timothy to his bus but before he got on she pulled him aside.

"Hey Timothy, I want to ask you something."

"What is it?"

"Well I was going to ask you this yesterday but was interrupted by your mom. Ummm, would you like to go out with me tonight?"

"Really...like a date?!"

"Yeah like a date. I really like you and I don't give a fuck what others think. I wanna get to know more about you. So what do you say?"

"I say...yes! I'll absolutely go on a date with you! What time?"

"8:00 PM and I'll pick you up at your house.

"Great, see you tonight!"

"Same bye!" said Cassie as she ran off excited.

Timothy got on the bus and was so excited. "I just got a date with Cassandra Sweeton!" he shouted. The other bus riders looked shocked and jealous, even the bus driver looked jealous.

At 8:00 PM, Timothy was ready for his date with Cassie. He was wearing an emerald green suit with a golden tie and green suede shoes.

"Oh gosh you look so handsome!" said his mom while taking pictures of him.

"Mom, it's not that big a deal!" Timothy said while blushing.

"Of course it is! This is your first date!"

Cassie arrived in her pink dodge challenger and came out in a sparkling pink skirt, a purple long sleeve crop top which showed a lot of her cleavage, and purple high heels.

"Wow Cassie, you look beautiful!" Timothy said while admiring her outfit.

"Oh thank you! You look great too with the green and gold color scheme!"

"Oh okay okay can I get one more picture of you two?!" Mabel asked excitedly.

"Okay fine mom."

Mabel took one last picture of their hands around each other's shoulders and they hopped into Cassie's car and drove off.

"Have fun you two! Oh my little man is all grown up!" she said as they drove off.

Cassie and Timothy drove around the town. During the drive, he had to pinch himself to see if he was dreaming but he wasn't. He couldn't stop staring at Cassie's pretty face and wondering how the date would go. Finally, they stopped at Sweeton's Palace.

"Oh sweet! The perfect palace for a princess like you!" Timothy said as they got out of the car

Cassie blushed and giggled, "Hehehe if I'm a princess then you're my prince."

"That's right! Is your mom working here tonight?"

"No, she's at home right now and my step-dad is working here tonight. My mom was taking pictures of me for the memory of me finding Mr. Right."

"Oh cool!"

Timothy and Cassie walked into Sweeton's Palace and got a great table and a menu.

"Wow Cassie, your mom is a genius! How did she come up with all of these dessert ideas?"

"She's a smart lady! Baking is kinda in her blood. Her mom was a baker before her and her mother and so on."

"That's awesome!"

A waitress named Leslie came to their table.

"Good evening! Can I take your order?"

"Absolutely madam! We'll have the apple cheesecake tacos and one oreo milkshake." said Timothy.

"Alright coming right up!" she said as she wrote their order down and walked away.

"So Timmy tell me a little bit about yourself, besides your big dick."

"Oh well my favorite color is green, I really love anime and superhero comics, and I wanna be a scientist."

"Well I'll bet you'll be a great scientist after seeing those science experiments in your room yesterday. So when did you get into science stuff?"

"Well I guess I got into that kind of stuff when I was younger. My mom said intelligence is a gift that should be used to help mankind. But enough about me, tell me a little bit about you."

"Well my favorite colors are pink and purple, my favorite singers are Sabrina Carpenter and Usher, and I love cheerleading and singing."

"Oh yeah you're a great singer! I heard you singing Blow by Kesha in the talent show last year and you were amazing!"

"Thank you! Also I love to eat sweets, I mean I've kinda been obsessed with them since I was young. My mom could barely make me eat healthy foods when I was younger."

"Wow, that's crazy!"

"I know I'm a fucking wild girl! So tell me what's the craziest thing you've ever invited?"

"Well I made this teleportation device that can transport you to any place in the world. All you have to do is type wherever you want to go and it will make a portal for you and take you to that place."

"Wow, that's amazing!"

"I know! One time I transported me and my friend Henry to Queensland, Australia and we hopped with kangaroos."

"Wow that sounds awesome! You sound like an adventurous person."

"Yeah but I actually prefer to stay in my room and do experiments all day."

"Hmmm understandable. Hey, what's your favorite animal?"

"Easy it's the green frog, Lithobates clamitans!"

"Nice! My favorite animal is this cute little critter called a sugar glider. It's a possum that can glide through the air and loves to eat sugar stuff like me!"

"Hahaha nice! I'm guessing it's your spirit animal?"

"Yeah it is! I've always wanted one as a pet, they're just so cute!"

"Yeah maybe you will one day."

Finally, a waiter brought their apple cheesecake tacos and oreo milkshake. The tacos were cinnamon coated tortillas with whipped cream in the middle, decorated with caramel sauce and apple slices. The milkshake had two straws and whipped cream on the top decorated with oreo cookie crumbs and one whole oreo cookie.

"Damn this is a magnificent spread! Let's dig in, baby!" said Timothy.

Timothy and Cassie ate the tacos and their eyes rolled with delight as they tasted them. The rich cinnamon flavor mixed with caramel and apple was absolutely amazing to them.

"Mmmmm these are the best!" said Cassie.

"I know, oh you got something on your lip."

Timothy saw some caramel sauce on her lip and got a napkin and wiped her lip.

"Hehehe thanks Timmy!"

"You're welcome."

After finishing their tacos, they tried the milkshake. They sucked from the two straws and their mouths were so close, they could've kissed right there and then. They were looking into each other's eyes and wondering how the night would end. After they finished, Timothy had some whipped cream on his lip and Cassie licked it off with her tongue.

"Hehehe had to return the favor."

"Thank you!" Timothy said while blushing.

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 where are we heading to next Cassie?"

"I was thinking we could stop at the roller rink. I want to burn off some of this energy I got."

"Great let's go babe!"

After 30 minutes, they arrived at the roller rink. They got out of the car and went inside.

"You're gonna be amazed when you see my moves." she said as she put on her roller skates.

"Oh I can believe that. Shall we skate?"

"We shall!"

We got on the rolling rink and showed off their moves. Timothy was a bit skilled and agile on the concrete after a few experiences with his friends. Cassie was more elegant like a figure skater and she shook her butt for Timothy to tease him. Timothy was amazed and aroused by her moves, and Cassie blew a kiss at him as she finished. The other couples cheered at Cassie's great performance.

"Wow Cassie, that was incredible! How did you do those moves?"

"Well in my younger days, I competed in some skating competitions and almost always won!"

"Cassie, you are an incredible woman!"

"Thanks Timothy!" she said before kissing him on the cheek.

Timothy and Cassie got back into her car and drove back to Bluebird Lane and arrived at Cassie's house. They got out of the car and snuck inside. Her mom was in the shower and they went upstairs and went into her bedroom.

"Wow this room brings back great memories!" he said as he remembered Cassie riding his cock on the bed as he sat on it.

"I bet it does! I still remember how your dick stretched out my pussy!"

"Yeah me too! Oh god that was incredible! Tonight was amazing Cassie, I never thought I'd ever go on a date with you."

"Well you made it happen because of the way you are Timothy. You're cute, kind and treat me like a lady should be treated."

"What can I say, I'm a nerd with lots of surprises!"

"You're more than a nerd, you're a sweet guy with a big heart, a big brain and a big dick!"

"Hehehe thanks!"

Cassie and Timothy kissed each other on the lips and started to cuddle as they did it. Cassie was on top of him and could feel his penis start to become erect as she laid on her crotch.

"Oh someone's getting excited! You know what let's fuck doggystyle!"

"Oh fuck really?!" But your mom, she's still here, she might hear us?"

"Well we'll just have to be quiet. So is that a yes or a no?"

Timothy thought for a moment. He didn't want to get caught by her mother seeing them having sex but really wanted to feel Cassie's warm wet pussy wrapped around his cock.

"Okay fine let's do it!"

"Hehehe great! Whip it out big boy!"

Timothy quickly stood up and removed his green pants and underwear, revealing his fully erected penis. Cassie slowly removed her pink skirt and panties, revealing her tight wet pussy. She got on her hands and knees, twerking for Timothy.

"Oh god! Oh Cassie, that thing is so wet!" he said while stroking his cock.

"Mmmm I know! Now fuck that big monster cock deep into me!"

Timothy grabbed Cassie's hips and pushed his cock deep into her. He could feel her warm, wet walls closing against his huge shaft. His penis was in paradise and he groaned as he started bucking his hips.

"Ahhhh God yes yes yes!"

"Oh God yes fuck me harder. Harder please!"

Timothy bucked his cock deeper into her pussy and smacked her butt.

"Mmmm fuck you like that naughty girl?"

"Oh yeah I love it! I love being your naughty little slut! I love teasing you!"

"Oh yeah well this teacher is gonna have to teach you some manners!" he said as he continued to pound her and grabbed her breasts.

"Oh yeah fuck that's how I like it! Pull my fucking hair!"

Timothy grabbed and pulled her hair as he continued to pound her hard.

"Awww fuck I'm cumming!" she shouted as she came on his cock.

"Mmmm yeah I love it when you cum on my cock!"

"Hehehe yeah I'm just a nasty slut meant to serve your cock! Ah fuck fuck-"

Cassie's orgasm was interrupted by her mom knocking on her door. "...sweetie? Are you okay in there?"

"Ummm yeah I'm fine!"

"Okay what are you and Timothy doing in there?"

"Ummm we're just watching a really...really good movie!"

"Okay you guys have fun!" she said as she went back into her room.

"Phew, that was close! Maybe we should stop."

"Oh fuck no! Don't you dare stop fucking me!"

Timothy obeyed Cassie's order and continued to pound her pussy nice and hard. He even got more dominant.

"Oh you're a dirty girl aren't you!"

"Yeah yeah I'm a dirty girl!"

"Yeah and also you're my dirty girl now!"

"Yeah Timmy I'm your personal fuck doll! You can fuck me anytime you want!"

"Yes yes yesss! Shit I'm gonna fucking cum!

"Oh yes please! Give me a nice big creampie! Claim my pussy as yours!"

"Oh yea yessss! Jesus ahhhh fuuuuck!"

Timothy's cock erupted deep inside Cassie's pussy. Long, thick ropes of semen hit the walls of her pussy and quickly filled her up. After finishing inside her, Timothy fell beside her, completely exhausted.

"Oh damn that was amazing!"

"I know! You completely stuffed me!" she said as Timothy's semen was spilling out of her pussy.

"Oh thank God for my hyperspermia!" Timothy said with absolute satisfaction and then he saw the clock and it was 12:00 AM. "Well I should probably get home."

"Okay see you tomorrow at school!"

"Hehehe you too!"

Timothy and Cassie kissed each other on the lips and Timothy made his way upstairs and walked out of her house and headed home. He couldn't believe that his first date ended in hot sex. 8 minutes later, he entered his home with pride.

"Oh sweetie you're home! How was it?" his mom asked.

"It was great Mom! We went to Sweeton's Palace, the rolling rink, and finally we went to her house and... watched a movie!"

"Awww that's great sweetie!"

"Yeah! I'm tired, I'm gonna go to bed."

"Okay goodnight sweetie!"

"Goodnight Mom."

Timothy went to his bedroom, took off his glasses, and got under the covers. He couldn't stop thinking about Cassie and their wonderful date. He was wondering what other adventures awaited him with her.