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LESBIAN SEX STORIES

How To Woo A Hot Nerd

How To Woo A Hot Nerd

by missroberta
20 min read
4.78 (24600 views)
adultfiction

All characters involved are over the age of eighteen, no exceptions!!!

•••••

Olivia was marching down the hallway, her head held high as usual, and her blue eyes burning with intensity. Her golden hair was up in a high ponytail, and she was wearing a pink and green sports jacket paired with tight leggings that accentuated her toned legs and firm ass. She had interrupted her laps around the school football field and was heading straight to the one classroom where she knew her best friend, Viv, was getting fucked by her boyfriend, as they did on Thursdays.

She burst the door open, interrupting the two lovebirds who were in the middle of having sex on the teacher's desk.

"Fuck, Olivia! Don't you know how to knock?" Viv's boyfriend, Josh, said, struggling to pull up his pants, especially since he still clearly had a huge boner.

"Liv, you know me and Josh use this room. You could've knocked," Viv said, raising her bra and closing her legs, feeling annoyed at having what she thought would be a great orgasm taken from her.

"I could've knocked, but I didn't want to," the blonde answered sharply, turning her eyes to the only guy in the room. "Josh, out!"

"What?! Why?!"

"Just go, Josh!" Viv said, already noticing something was up with her friend. "I'll call you later."

"But..."

"Go!" Both girls said in perfect unison, making Josh leave sadly and with a severe case of blue balls.

"What's the deal?" Viv said, fixing her black hair into a bun.

"You have to see this!" Olivia answered, hopping up on the teacher's desk right by Vivienne's side and handing her iPhone to Viv.

There was a video paused on the phone, and Viv quickly pressed play, dying to know what this was all about. She couldn't have been more shocked. In the video, a guy was on all fours, naked except for cat ears and a collar, getting fucked by one of the school football team members and sucking off the other. Viv quickly recognized Jace and Will in the video--the only gay members of the team--and she wasn't surprised by their antics. Both were known to like things a little kinky. What shocked her was the guy in the cat ears, whom she recognized as Steve Miller.

Her mouth hung open, but as soon as she connected the dots, which happened rather quickly, her lips curved into a smile worthy of a true winner. The blonde girl by her side mirrored that same expression. Olivia's plump lips, adorned with slightly reddish lip tint, were curved into the smile of a cat that just caught the bird. They looked at each other and high-fived with enough strength to leave both their hands stinging.

"He's cheating on her! And with guys, no less," Viv said, elated.

"This is my chance!" Olivia answered, her mind filling with schemes. "Finally, I'll end them for good!"

•••••

Holly Smith was wearing basically the same thing she had worn the day before, and the day before that, and every other day ever since her mom stopped dolling her up for school: a loose sweater in a boring shade of brown and jeans that were absolutely not form-fitting, looking baggy and old, not to mention the hundred-year-old sneakers.

But even though Holly actively tried to look as basic and boring as possible, no one could deny that underneath all the loose fabric was a body full of promises. She wasn't skinny; she was chubby in all the right places, maintaining a pear-shaped figure with an ample bosom that no loose sweater in the world could hide. And her face--God, her face was the best part.

She had beautiful green, almond-shaped eyes that shined brightly, even though they were always hidden behind the thick lenses of her glasses. Her pouty lips, in a beautiful pink color, just begged to be kissed. Her pretty button nose and soft cheeks were adorned with freckles that formed constellations across her skin. To top it all off, everything was framed by her gorgeous chestnut hair, which fell in waves over her shoulders and was long enough to reach the small of her back. Her hair was the only thing about her appearance that she actually liked, so she took great care of it.

She entered the school and, as usual, walked to her locker without greeting anyone. It wasn't that she was rude; she was just very shy. Even though she knew most of the people there--some since kindergarten--she had very few friends and lacked the courage to greet acquaintances, even though they would probably greet her back. But she didn't know that, so she walked in silence, her head down, staring at the dirty floor.

Holly finally reached her locker and started getting her things ready for class, feeling happy because today she had chemistry in the morning, her favorite subject. After she grabbed everything, she took a look at her phone, more specifically her chat with her boyfriend.

She had sent Steve a good morning text and asked if they could hang out today. After all, it had been months since they went on an actual date, and that's not what a relationship is supposed to be like, is it? But he hadn't answered. He always took too long to reply and justified it with random, lame excuses, which always ended up in huge fights. She sighed, sadness creeping into her. She squeezed the phone in her hand, turning off the screen and angrily shoving the device into her pocket.

As she turned around to stomp angrily toward the classroom, moping about her failed relationship, she found herself face to face with Olivia Spencer--the head cheerleader and the hot girl who had the whole school scrambling at her feet. Holly couldn't help but gasp and drop her things at Olivia's sudden appearance.

"Oh my gosh, I'm so sorry," Holly said, dropping to her knees to gather her stuff. To her surprise, Olivia did the same, helping her collect her belongings.

"Chill," Olivia said, giggling a little at Holly's clumsiness. "My bad, I startled you, right?"

"A bit," Holly answered with a shy smile, and both girls rose to their feet. She couldn't help but be impressed by Olivia's height--5'9" of pure glory--until she heard the blonde clear her throat. Holly quickly snapped back to reality, taking the notebook that Olivia was handing her. "Thank you!"

"So, you heading to chemistry?" Olivia asked, making Holly feel a bit taken aback.

It would be an overstatement to say they'd never talked--sometimes they did, but very rarely and only when they had a reason to, like when they ended up in the same group project or when Olivia missed class and absentmindedly asked Holly about what she'd missed, knowing Holly never skipped a class. But they'd never talked just for the sake of talking to each other, so once again, Holly found the situation weird. Still, she didn't want to seem paranoid, so she just went with it.

"I am," she answered. "You too, right?"

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"Yes! So let's head there together!" Olivia said, already turning and starting to walk down the hallway, with Holly hurrying to follow by her side.

Holly had no idea what to say as they walked toward the classroom, but in her mind, she loathed the fact that the class wasn't closer so she could end this awkward situation as quickly as possible. She sneaked glances at Olivia but couldn't stare at her for too long without feeling like she was going to burst. The cheerleader exuded an aura of confidence and power, strutting down the hallway as if she owned the whole building, being warmly greeted by almost everyone they passed. Just looking at her was enough to make Holly anxious.

"I heard you like chem," Olivia said, breaking the silence. "You're Mr. Willy's pet student."

'Is she bullying me?' was the first thought that crossed poor Holly's mind. But Olivia wasn't known for being a bully. She could be rude and entitled sometimes, but never a bully, so the anxious little nerd quickly brushed off the thought and answered.

"I really love chemistry," she said shyly. "It's actually my favorite subject."

"That's great!" Olivia answered, suddenly draping her arm across Holly's shoulder and pulling her closer. Holly immediately felt her heart race and thought she might melt completely. It wasn't easy being so close to a bombshell like Olivia--it made her feel weird things low in her stomach. But she wasn't supposed to feel that way. 'Fuck! What am I, a pervert? Act normal!' she thought to herself.

"Y'know, I'm kinda sorta failing at chem, and I've been wondering if you could lend me a hand?"

"Oh," Holly said, sounding very relieved that, after all, this was just another one of their technical exchanges. It wasn't Olivia suddenly deciding to stick around Holly. "Sure, I can try! But I don't know if I'm that good at teaching."

"Don't sweat it, I'm sure you'll be great!" Olivia replied with a bright smile, maybe a bit too bright for someone who simply got a nerd to help her with chem. "So, you're free today?"

"Today?!" Holly asked, stopping dead in her tracks.

"Yeah, we can go to my house. It's better than the library."

And once again, the situation turned weird. Holly thought Olivia was asking her to take some time from lunch and help her at the library--nothing too fancy. But it turned out Olivia was full-on inviting her to her house, which left the little nerd girl shocked and taken aback by the sudden turn of events.

But in the end, Holly was free. She confirmed it by checking her phone and seeing that Steve hadn't even read her message yet. And when he did, she was pretty sure he wouldn't want to hang out with her. Her heart broke a little at the realization that, yes, she was free--free because not even her boyfriend would bother to spend time with her.

"Hey, you okay? It's all right if you can't make it today," Olivia said carefully, noticing the sadness that suddenly took over the smaller girl's features.

"No, it's okay," Holly said, trying to force a smile. "I'm free!"

"Great!" The cheerleader said excitedly, pulling out her phone and exchanging contacts with Holly. "I'll text you the time and address, okay?"

"Sure!" Holly answered, just as they arrived at the classroom.

"So, see you later?" Olivia asked, standing face to face with Holly and staring intently into her lovely green eyes.

"Yeah, see you later!" Holly replied, surprising even herself. Under normal circumstances, she would have made an excuse not to go, but today was different. If she didn't go to Olivia's house, she would just end up in her bed all day, moping about Steve. Desperate times called for desperate measures.

So maybe this sudden turn of events was a good thing after all. At least she wouldn't have to keep thinking about motherfucking Steve.

•••••

Just like Holly suspected, later that day she got a text from Steve explaining in 10 lines why he couldn't go out with her today and how she was being such an inconsiderate girlfriend, begging for attention while he was busy studying so hard to get into his dream college. As if Holly didn't study hard too. In fact, she studied a hundred times harder than he ever did, but fuck it, she had more important things to think about--like what she would wear to Olivia's house.

She didn't own anything much different from her classic boring sweaters or T-shirts for hot weather, paired with her usual old, loose jeans. But hey, that's what moms who wear the same size as you are for! So instead of checking her own wardrobe, Holly hurried to her mom's closet to find something a little more interesting.

She wanted to look nice, after all. Olivia was so stunning, and being next to her made Holly want to look better. Not that she could ever look as good as the cheerleader, but she wanted to look at least decently put-together so she wouldn't stand out too much.

Raiding her mom's wardrobe wasn't an easy task. Besides the fact that they looked so much alike--both in body type and facial features--Holly and her mom had completely different personalities, which obviously reflected in the way they dressed. Holly was a cutesy little nerd girl, but her mom? Jesus, Holly's mom was an honest-to-god MILF, and she dressed the part. In fact, the first kind of bullying Holly ever experienced was the "hot mom" bullying, where disgusting guys would provoke her by talking about how horny her mom made them. Not good memories, those.

But there had to be something usable for Holly in there--and there was. Holly found a cute bohemian-style shirt that left her shoulders bare. It was a little revealing but not exaggeratedly so, at least that's what she decided while staring at her reflection in the mirror, evaluating the amount of cleavage it showed. Definitely more than usual, but nothing crazy. Feeling satisfied, she paired it with the only pair of form-fitting jeans she owned and some sneakers.

After finishing up, packing her study materials in her tote bag, and applying just a bit of lip tint--so she wouldn't look like she was trying too hard (though she was)--Holly headed to Olivia's house.

She decided to walk, surprised to find out that Olivia didn't live very far from Holly's own house. It was close, but not so close that it would be unreasonable to take the bus, though she opted not to. She was feeling nervous, her stomach turning, and hoped that a nice walk would help clear her head a little. 'I hope she doesn't think I'm weird or something.' 'I hope I'm good at teaching.' 'I hope she likes me.' These were the thoughts going through her mind, but the last one made her stop and wonder, 'Why do I want her to like me? It's not like I owe her anything.' And that was all she could think about until she finally reached Olivia's front door--and the conclusion to her question: 'Maybe because she's popular.' She rang the bell, still anxious, but less so than she had been before the walk.

It didn't take long for the door to open; after all, Olivia had been excitedly waiting for Holly's arrival. When she opened the door, Holly's mouth formed a cute 'O' shape. Olivia was wearing gray sweatpants and a black crop top that showcased the cheerleader's defined abs, her blonde hair up in a messy ponytail. Even so, she looked stunning without even trying. Holly had never seen Olivia dressed so casually, and now she felt awfully overdressed, wanting to run away back home and forget about this crazy encounter. But Olivia was faster, pulling Holly into a tight hug, shocking the nerd girl even further.

"Thank you for coming!" Olivia chirped excitedly, quickly pulling Holly inside.

"T-thanks for inviting me," Holly answered nervously.

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"So, my parents are out, and we'll be studying in my room. But first, do you want something to eat or drink?" Olivia asked as they entered the very nice-looking living room.

'Wait,' Holly thought as soon as the words left Olivia's lips. 'Why is she telling me her parents are out?' She wondered but quickly brushed the thought off, not wanting to overthink.

"No, thank you. I'm not feeling hungry right now," she declined politely.

"Okay, but I'll get us something to drink anyway. Do you like lemonade?"

"Sure," Holly answered, following Olivia into the kitchen, where she grabbed a jar of ice-cold lemonade and some glasses. Then, they headed straight up to the cheerleader's bedroom.

Olivia's room looked like it came straight out of Pinterest, with a mix of cream tones and vivid splashes of color. Everything about it screamed cozy. One of the walls was adorned with fairy lights and covered with Polaroid pictures of Olivia and her friends. But the star of the room was definitely the bed--a king-size bed draped with blankets, fluffy pillows of all shapes, and even a penguin plushie. Holly was in awe.

"You like it?" Olivia asked with a proud smile.

"It's amazing! I love it!" Holly replied.

"Good! 'Cause we'll be spending a lot of time here."

"You're that bad at chem?" the little nerd asked, raising a brow, and Olivia couldn't help but smirk.

"Exactly."

•••••

Olivia wasn't that bad at chem. She definitely wouldn't be the next Marie Curie, but she knew her way around the subject pretty decently. Holly didn't understand what Olivia meant when she said she was struggling with it. They were both sitting on Olivia's bed and going through what Holly thought were the most important topics. Two hours into their study session, Olivia gave a big stretch, one that communicated she was getting tired of all the studying.

"Let's take a little break," Olivia stated, not even asking.

"Okay," Holly answered, setting her books aside as Olivia did the same.

"So, Holly," the cheerleader said as soon as the studying stuff was out of the way, "how are you and Steve?"

Holly could feel all the blood rushing to her face, and her stomach became once again a complete anxious mess. This was the worst question Olivia could ever ask her, and she just did.

"W-what do you mean?" she stammered.

"Well, you guys are dating, right? For three years, nonetheless. How's that going?" she asked casually. Not even a trained detective could find an ounce of intention or malice in that question, but Olivia knew that everything she said from now on was filled with it. That was what made Holly try to answer; in her mind, Olivia was just trying to make small talk.

"Well," Holly said, pausing to think about her answer for a bit, "good. We have our issues, but everything's fine."

"You took too long to answer!" the cheerleader said jokingly, making Holly feel even more nervous, as if Olivia had just caught her lying--and she did. "What types of issues?"

Holly took a deep breath before standing her ground. "I'm sorry, Olivia, but I don't really wanna talk about that."

The cheerleader's face slowly shifted into a serious expression, one that gave away nothing and demanded obedience. She stared deeply into Holly's green eyes and let her gaze wander momentarily to Holly's lips, which were pressed together into a thin line as she tried to contain her anxiety. 'Cute' was the only word Olivia could think of.

"C'mon, it's not a big deal. Answer the question," Olivia said simply, but her tone made it clear that she wouldn't ask twice. Holly didn't have to comply, but for some reason, she wanted to.

"The same issues all couples our age go through," Holly said, hoping that would suffice. But Olivia just kept staring, so Holly knew that answer wouldn't satisfy the blonde. "We haven't been hanging out together a lot these days--or, more exactly, these months. He's studying a lot to try and get into his dream college, and I'm studying a lot too, but he can't seem to focus on anything else. So, I don't know, I guess I'm feeling abandoned and like he doesn't care about me. We've been fighting so often I can't even remember the last time we talked without it ending in complete disaster."

Holly was like a broken dam, the words and feelings flowing out of her lips intensely and out of control. She didn't even care about what Olivia might think anymore; she just had to get it off her chest.

"He's being such a dick to me! Sometimes he takes days to answer my texts--can you believe it? Days! I think he's avoiding me at school, but every time I ask him if he wants to break up, he begs me to stay and talks about how this is just a phase and we'll get through it together, and then he acts normal for like a week until it all starts again!"

After Holly finished getting everything off her chest, a silence settled in as Olivia reached for her phone and handed it to Holly.

"What's this for?" Holly asked, confused.

"Take a look," Olivia said simply.

Holly looked at the screen. There was a video paused there. She glanced back at Olivia and then back at the video before gathering the courage to press play. When she did, she felt her heart drop into her stomach. She saw Steve on all fours, having sex with not one but two football team members. He was wearing ridiculous little cat ears and a collar--Steve was cheating on her. Suddenly, she was unable to see anything; her tears blocked her vision from what was the closest she had come to a glimpse of hell. Holly felt Olivia's hand lightly on her shoulder, but she could barely tell because the pain made her disconnect from her body. She could hardly hear Olivia's soft voice as she said tenderly,

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