Disclaimer: I don't own the show Glee or any of the characters. This isn't written to make money, only for harmless fun.

Characters: Quinn/Rachel, Quinn/Jacob Ben Israel

Codes: ff, mf, anal, finger, oral, rimming

Glee: Quinn's World Part 7 - Unexpected Firsts
by The Chemist

Things usually went Quinn Fabray's way. She was the head cheerleader, always dated the hottest guy and school and things generally went her way. Sure she got knocked up, but she gave him up for adoption and he was now the child of a loving couple that could take care of him.

That was until recently. She had been dating the new guy at McKinley High, Sam, but thanks to Santana he dumped her. Sure, she'd been cheating on him behind his back with her ex-boyfriend Finn, but if it weren't for that conniving Santana then she'd still be with him.

Even though she didn't want to admit it, the way things happened might have been for the best. Finn was her first love, and even though she had cheated on him last year when they were dating, she never stopped loving him. Sam was a great guy and she didn't want to lose him until she was sure about her and Finn, but this situation might have been the push she needed to fully commit her heart to Finn again.

Unfortunately, the Glee club had extra animosity since the whole situation went down. Everyone was upset at how Quinn had handled it, and that extended outward to Finn by association. Obviously Santana and Sam weren't talking to the couple because of blatant reasons, but Rachel was also especially pissed off. This was probably because of her obsession with Finn.

Normally the Glee club being dysfunctional wouldn't haven't been much of a concern, but sadly Regionals were in a few days. Their only chance of winning was everyone being on the same page and that meant Quinn having to be the bigger person and take the verbal abuse from her teammates and do whatever she could do in order to regain some of their favor.

"Do you have a second Rachel," Quinn asked the rival for her man's heart.

"What do you want Quinn? To flaunt Finn in my face," Rachel asked with bitterness. "I'm pretty busy trying to write my original song that'll win us Regionals."

"I know. That's why I'm here to talk to you," she replied while they talked in the vacant auditorium.

"I don't need your help," Rachel responded with a mixture of superiority and offence.

"You clearly do. I overheard you singing to Finn in the choir room," Quinn explained. "Don't get me wrong, you have a great voice. It's probably unparalleled by anyone in the region but that song wasn't good. Not good compared to what you could be doing."

"And I'm suppose to believe that you can actually turn me into a great songwriter," Rachel said dismissively.

"Yeah. You heard what Finn said after your song. You need to dig deeper into your pain in order to write a truly great song. I can bring out every ounce of pain you have. Not just with Finn but how I've made your life hell at school. I'm popular, come from the most nuclear family and have been everything you're not for the past two years," she told her.

Rachel hated to admit it, but Quinn was saying things that were true. Just by looking at the gorgeous blonde made her angry that she had Finn and not herself. It also made Rachel feel like a loser for not being classically beautiful or the future prom queen. She didn't know the true reason why Quinn was helping her, as she didn't believe the cheerleader was doing it in order to help win Regionals. In reality, Quinn was only doing it to keep an eye on Rachel so that the short brunette couldn't steal her man.

"We're actually going to do this then," Rachel asked, hoping that Quinn would back out of the proposal.

"Yup...we're actually going to do this."

The next few days weren't easy for either of the girls. Quinn hated spending time with Rachel. After all, the girl had no style, nothing ever interesting to talk about and the only thing they had in common was their love for Finn. It wasn't easy for Rachel either. The more sight of the blonde cheerleader made her angry, but after two days she had completed one full song and by the end of the third day, she had written another.

But one the last night before they had to present their work to Mr. Shuster and the rest of the Glee club, something happened. All their hard work and deep pain caused Rachel to go on a huge writing push and before either one of them knew, it was midnight and they were done two songs.

"This is seriously amazing Rachel," Quinn acknowledged.

"You're just being nice...that or staying up so late the last few nights has fried your brain," she joked.

"I'm not insane and I'm not being nice. It's not in my character. This is some top level stuff," the blonde replied, looking the shy girl in the eyes.

"You really think so Quinn?"

"Yeah I do. Everyone will when you belt it out tomorrow for the group too. They'd have to be idiots not to see the awesomeness of this song!"

"I know we haven't always seen eye-to-eye, but I can honestly say I've loved getting to know you better the past few days. It hasn't always been nice things we've talked about but you're caring, considerate and quite smart. It's easy to see why Finn loves you're beautiful," Rachel said, the last part making her blush and causing her to break eye contact with the cheerleader.

"That's really sweet of you to say Rachel," Quinn replied. She wasn't expecting to get such nice words out of her rivals mouth. Reaching her hand out to take her chin and lift it so they were staring back in each other's eyes, "I'm surprised to hear myself saying this, but I really loved hanging out with you. And I can't blame Finn for dating you before. You're uber-talented and you have such a nice tight body."

"Thanks really means a lot coming from you," Rachel replied sheepishly.

Quinn didn't know what overtook her at that moment, but something was making her gravitate towards the annoying brunette. Taking the girl's head in her hands, the cheerleader gently pulled her towards herself until their lips pressed together.

The kiss was soft and tender as both girls were worried about scaring off the other. After a few seconds, sure that Rachel was ready to go a little further, Quinn parted her lips and was happy to feel the talented singer mimic her movement. Slowly, the blonde inched her tongue forward until it entered the other girl's mouth and slid on top of Rachel's tongue.

"Mmmhh," Rachel groaned in response to her passionate kiss.

Quinn was happy to know that her kissing skills translated from men to women. As the minutes passed, their kissing became more intense to the point where they were both resting up on their knees, nimble bodies pressed tightly against each other and their tongues sloppily mingling together.

The blonde couldn't help herself anymore and slid her hands up Rachel's slender body until her hands roamed over her small but perky breasts. She could sense that Rachel was a little uneasy with the progress but the more inexperienced girl relaxed soon after. Quinn decided to push the envelope by grabbing the hem of Rachel's sweater and pulling it up and over her head, leaving her upper body covered only by her bra.

"You have such a sexy little body," Quinn complimented before kissing down her neck.

"'s nothing compared to yours," she replied.

Quinn reached behind her and unhooked Rachel's bra. She straightened up so that she could look the brunette in the eyes as she peeled the garment from her body and exposing her boobs. Rachel made a slight attempt to cover herself up but Quinn had anticipated and stopped her arms from doing so.

"There so nice. And those nipples make me just want to suck on them all night," the cheerleader told her.

Rachel couldn't believe how sexy it felt to have a girl as smoking hot as Quinn Fabray telling her how good looking she was. That thought was pushed out of her mind when the other girl's soft lips latched onto one of her nipples and her wet tongue circled her erect pink tip. Quinn didn't ignore the other boob as she used her thumb and forefinger to roll her nipple in a sensual way.

"Ughhh...that good," Rachel moaned in delight.

"Have you ever done this before," Quinn asked after spending some time sucking on both nipples.

"Finn and I got to third base before," she answered.

"I meant with another girl silly," Quinn said, flashing her gorgeous smile.

" I haven't. I just lost my virginity a few weeks ago," Rachel admitted.

"That's okay, I'll walk you through it. Besides, once you start I guarantee that you'll be a quick learner. Who else knows exactly what a girl wants than another girl," she reasoned.

Rachel bravely nodded her head, giving her complete faith to the more experienced blonde. "I trust you Quinn."

"I'll go first too, that way you have a good model to follow," she explained.

The pair started kissing again before Quinn lowered the brunette softly onto her back with the soft bed beneath her. Rachel could feel her skin crawling with goosebumps as she kissed her way down her neck, chest and flat stomach until arriving at her tights. Hooking both waistbands of the tight pants and underlying underwear, Quinn pulled them down and off of her body, leaving the načve girl naked.

Rachel's pussy was completely hairless, much like Quinn's own pussy. Even though the blonde wasn't the foremost expert in girl-on-girl action, Quinn knew her way around a vagina. Separating Rachel's legs, she pushed her head right into the other girl's groin with her tongue immediately running the length of her slit.

"Oh yesss," Rachel screamed louder than she had hoped, aware her parents weren't very far away.

Quinn smiled to herself knowing that she had such an effect of her one-time rival. She did the same motion again by even slower dragging her tongue from the bottom of Rachel's cute pussy all the way to the top. Once reaching the top, Quinn clamped her lips with an air-tight seal around her clit.

"My GOD AHHHHH," Rachel screamed again.

"Everything okay in there," Rachel's dad asked from behind her bedroom door.

"Just practicing our song Mr. Berry," Quinn answered. "We'll keep it down from now on."

"Good night girls," he said before they heard his footsteps.

"Into the pillow lover," she told Rachel.

"Fine just keep making me feel like that," Rachel begged.

Quinn lowered her head again and slowly lapped again along the girl's slit. She could tell Rachel was getting hornier by the second but she didn't want her fun to be over too quickly. Deciding to try a new tact while still going slow at a teasing pace, Quinn pushed her tongue just inside her opening and licked the perimeter, much to Rachel's delight.

"Mhhhh," she moaned into her plush pillow.

"You like that," Quinn asked her partner while using her fingers to rummage through the other girl's folds.

"So good," Rachel said with a husky voice. "Please go faster."

"But then my fun will be over too quickly," Quinn said with a smirk.

"I'll do the same to you but please make me cum. I'm begging you Quinn," she said.

Quinn let her actions answer Rachel's request by sticking it's full length as deep into her pussy as the muscle would go. The brunette bucked her hips off the bed to help her get even further into her pussy. Quinn was savoring the taste of the other girl's hole as she tried to scoop as much of the sweet fluid onto her taste buds while still pleasing her new friend.

"What do you like better, that or...," Quinn asked.

"Or wha...AHHH," Rachel started to question before a fresh wave of pleasure washed over her body and into her brain.

Using two fingers to slowly push into her extremely tight pussy, Quinn let her hole expand around them before gliding them smoothly in and out. With each passing minute, the cheerleader would start pushing in quicker. Just when Rachel thought that the sexy blonde couldn't move any faster, Quinn drove her fingers in as far as she could then rubbed her fingertips along Rachel's inner walls.

"I'm going to cum so soon," Rachel warned.

"Sooner then you think," Quinn thought before repeatedly flicking out at her sensitive clit with her tongue.

"MMHHHH....AHHHHHH," she moaned deep inside her pillow.

Just as Quinn felt her pussy clamp tightly down on her fingers, she slid them out of the opening but quickly replaced them with her tongue. Sticking the muscle just inside her hole, the blonde was able to suck up every drop of Rachel's sweet nectar as the talented singer came into her mouth.

"Delicious," Quinn told the exhausted girl.

"That...was...amazing," Rachel told her. "Want return...the favor?"

"Not tonight. Get some sleep. I have the feeling that this could be something we do often," she replied.

"I'd really like that," Rachel said, already half asleep.

Quinn went to the light switch and shut the light off before drawing the blinds and jumping into bed. The pair immediately took each other in their arms and Rachel passed out shortly there after. It took Quinn a little longer to fall asleep as she thought of what this meant with Rachel. She hadn't planned on having sex with the annoying girl but now she had to think of how to use her new relationship to manipulate and control the brunette.

* * *

"Okay so is there any other original songs," Mr. Shuster asked the Glee club.

It hadn't been a good day for the Glee club. Not only was it the day before Regionals, but ever member's attempt of songwriting had been either bad or inappropriate. It was hard to tell who was the best so far, Santana sang about Sam's exceptionally large mouth while Puck wrote a song called "Big Ass Heart". To top it off, their most skilled member wasn't there yet.

"Sorry we're late Mr. Shu," Quinn apologized as her and Rachel came walking into the choir room.

"Please tell me you have some good news," he asked.

"Not good news, but great news! I've written two songs. Here are the sheet music so we can practice right now," Rachel said as she passed out the paper to everyone in the club.

"Girls, this is brilliant," Mr. Shuster told them. "Heart-felt and it seems like it'll be perfect for the competition."

"Glad you think so. It wasn't easy but Rachel pulled it out," Quinn complimented.

"We did it Quinn. I couldn't have done it without you," Rachel said. Despite all that she hated about her, Rachel gained some respect for the blonde girl after the past 3 days, even considering her a friend.

"So I take it this is a ballad and the second one is..."

"It's our anthem. The one that will win us Regionals," Quinn bragged.

"We don't have much time but if we practice extra long tonight and on the bus ride to the competition then we should be in good shape," Rachel instructed.


"I have to take this, it's my mom," Quinn said as her phone rang.

As Quinn went outside to answer her phone, Rachel coordinated everyone inside the choir room. Though most people didn't like her bossy personality, it was sure coming in handy here. In only a few minutes she had the Glee club set up the way she envisioned while her and Mr. Shuster went off to organize how to work in the special dance Brittany and Mike had been working on.

"Everything okay Quinn," Finn asked as the blonde re-entered the room.

"That was my mom. She reminded me that I have my older sister's wedding Saturday," she asked, her normally pale face looking even whiter.

"So? That's the day after the competition you drama queen," Santana retorted.

"So it's Saturday at Philadelphia," she replied.

"So it's only like an hour by plane," Sam shot back at her.

"Long story but I'm deathly afraid of airplanes. We're driving. My parents are making me skip school tomorrow so we can get there before dark," Quinn informed the group.

"But that means..."

"That means I miss Regionals," Quinn finished.

"But we need you," Mr. Shuster told her.

"I know but it's my sister's wedding. I'm the maid of honor," Quinn rationalized, on the brink of tears. She loved the Glee club and it was killing her to abandon them in their hour of need.

"Can't you leave after Regionals," Puck suggested.

"I don't have a license and neither does Finn. There is no chance my parents would risk being late to the weeding so that I could sing," she said.

"I may know someone that could help," Rachel piped in. "But I wouldn't wish this as punishment to anyone."

"I'm desperate. I'll do it," Quinn accepted before even hearing the condition.

"Well a 'friend' is driving to Philadelphia this weekend to check out colleges for next year," Rachel started. "He doesn't want to miss school so he's leaving after classes, right around the same time we'll be receiving our trophy after we win."

"Wait...the only guy you know that's able to leave the state driving is. Jacob," Finn deduced.

"Jacob Ben Israel? That creepy guy that runs the school newspaper. Karma's a bitch Quinn," Santana laughed.

Jacob was a sexually deprived junior that had the hots for Rachel...or any other pretty girl in school. Using his insight as a journalist, he would get dirt on girls then blackmail them for panties or bras, such was his fetish.

"Please do it Quinn. We need you badly," Rachel begged her new quasi-friend.

"Give me his number," the pretty cheerleader requested, giving everyone else a sense of relief after the brief drama.

Quinn left the room again to use her phone. She'd never really talked to the boy before because he was super awkward so she avoided him like the plague. It had worked for the first two years of her high school experience but now she was being forced to call him up and ask for a favor.

"So are you performing with us," Finn asked as she returned to singing practice.

"I a price," Quinn answered.

"What's the damage," Brittany asked her friend.

"Normal stuff like paying half of the gas price plus all food and drinks. Then we have to take lots of pictures together so that he can brag to anyone he meets in Pennsylvania about how him and I are dating," she informed the group.

"That doesn't seem to bad," Rachel concluded.

"That wasn't all. Like you guessed, he wants a pair of freshly worn underwear. He prefers a silk thong, red or black, but he'd accept a satin pair if I saw fit," Quinn finished.

"And that's the pervert we all know and love," Santana remarked. "Swallow your pride and do it. After all, you are use to swallowing, aren't you Quinn?"

"Yup Santana, just like you're use to swallowing...after having a cock up your flabby ass," Quinn retorted.

"You bitch," Santana screamed before Sam grabbed her before she could get close to the blonde.

"Enough ladies. How the hell are we going to win a team competition if we aren't acting like a team? I know stuff happened between you two but bury the hatchet until tomorrow night. Then you guys can kill each other if you want," Mr. Shuster weighed in.

"Did you want me to talk to him and scare him a bit," Finn asked.

"Not a good idea Finn," Rachel interjected. "Jacob isn't the type to back down. He'll either refuse to take her or ask for more if he was to still drive her."

"It's fine babe. It doesn't really bother me too much, plus I'm desperate. I'll be fine," Quinn reassured him.

The next 18 hours seem to fly by for the McKinley High Glee club. They stayed at the school until 8pm rehearsing for the big event and it was starting to come together. Rachel helped the group learn the two songs, explaining the role of each member in both performances. Brittany and Mike had to alter their dance to fit with the music better, but they felt like it now worked. Meanwhile Mr. Shuster was buzzing around putting the finishing touches and tightening up everything else.

The students got to leave school early and on the bus ride they practiced twice more until they arrived at the venue. Time seemed to slow down once they arrived as nerves started to kick in. They got changed into their light blue outfits and tried their best to relax in their changing room.

"Alright guys, we're up next. Just remember that I'm proud of how well you guys have come together in the past day. We have a great song, and amazing talent. Stay loose and try to have some fun out there," Mr. Shuster told them. "Now get out there and break a leg!"

While it had seemed like a 10-hour wait from the time they arrived at the auditorium until they performed, time zoomed by once they were on stage. Their original songs were amazing and easily won them first place in the competition, beating the team Sue Sylvester was coaching and the Warblers, which was the Glee club of Kurt's new school.

"Hello Ms. Fabray. Ready to go," Jacob asked as he waited inside the building for Quinn after her show.

"Yup, let's head out," she replied as she followed him out to his car.

Like a true gentleman, the boy with a wicked afro opened the passenger side door for the girl. However, he did try to sneak a peek up her dress as she swung her legs inside the car and look down her top. Both tries went unseen by the cheerleader, but all Jacob could see was some cleavage and the tip of her bra.

"Thanks so much for driving me to Philly," Quinn said to the nerdy boy.

"No problem. I always love the chance to collect favors from beautiful girls, especially cheerleaders," he laughed.

"Oh," she replied feeling uneasy.

"I'm mostly just joking. It's a long drive so the company is much appreciated," Jacob told her, making her feel less awkward.

For the next several hours the unlikely pair talked comfortably, which was quite surprisingly considering they'd never chatted before and they had quite different social circles. Quinn was shocked to find out that Jacob was very current in celebrity affairs and he may have actually known more about movies than her, which she'd never have guessed.

"You're a lot...YAWN...different than the image you give off at school," Quinn told him.

"Thanks but its appeared that I've bored you Ms. Fabray," Jacob stated.

"No it's not that. I haven't been sleeping great lately," she shared. Ever since she'd gotten extremely horny in the last few months she noticed that she was sleeping less and being more tired throughout the day and night.

"Why don't you take some of my sleeping pills," Jacob offered. "They're over the counter and no side effects."

"No I can't do that," Quinn refused.

"Quinn, stop being so damn stubborn. You need help sleeping and God knows you can't afford to look tired as the maid of honor at your sister's wedding so just take the pill," Jacob spoke sternly, somewhat out of character.

Quinn knew he was right. She really needed a good night's sleep and she always had trouble sleeping in a car. Even though she didn't like having to rely on drugs or other people for that matter to do anything for her, she knew she should listen to Jacob.

"But what if you need me to take over driving," Quinn asked.

"I've had 3 large coffees already, have a fresh one on the go and have taken 2 caffeine pills. I'll be fine as long as my heart doesn't explode. Those pills should knock you out for at least 3 hours of solid sleep so any time after that you'll easily be able to be woken," he answered.

Quinn took the bottle that he was offering and dumped out one capsule into her hand. Popping it in her mouth, she took a big gulp of her water before swallowing down both the liquid and the pill.

"Alright, done. I'm just going to put my seat back and enjoy some sleep finally," she said before she almost instantly passed into a deep rest.

Even though Quinn had only been asleep for 30 minutes, Jacob found himself to be missing the conversation. In fact, on more than one occasion he even found himself start to drift on the road as his eyelids got heavier.

"Damn it Jacob, stay awake," he said to himself while continuing to cruise down the road.

Checking his blindspot again, he noticed the sleeping figure of Quinn Fabrey. She'd taking out her ponytail so that her long blonde hair was framing her beautiful face, making her twice as pretty. Even while sleeping the girl carried herself in a sexy way with one hand draped across her medium sized tits while the other rested on her flat stomach.

"You look nice in that dress Quinn," Jacob commented aloud.

He had to chuckle after realizing he was talking to a girl who was out cold. Sadly though, that small amount of conversing had made him more awake than he'd been in the past 20 minutes. He decided that he might as well continue to talk to the unconscious blonde since it was having a positive effect on him and she'd be unaffected.

"I love that you wear dresses so much. They show off your sexy legs and if I can time it just right, I can see your panties when you're walking up the stairs," he shared. "Oh and that reminds me. You should keep wearing thongs as often as you do because that ass is amazing."

Reaching over to get a sip of his drink, Jacob overshot and landed his hand on Quinn's bare thigh. He quickly retreated before she woke up startled and calling him a creep, but the blonde remained sleeping soundly.

Curious as to how far under she was, Jacob put his hand back on the same spot but held it there longer. Taking it to the next step, he squeezed her leg, lightly at first but then really added some pressure. Watching her face as best he could while driving, the cheerleader never flinched or should any sign that she was coming out of her sleep.

"Interesting," Jacob said with a devious grin.

Sliding his hand up her leg, he rubbed his fingertips along her inner thigh until the hem of her dress was bunched around her waist. Going in under the waistband of her panties, Jacob was pleased to find that the cheerleader had a freshly shaved pussy.

Jacob started driving slower so that he could intently watch her body for any signs of waking up while he ran his fingers through her pussy lips. He did the same action a few times to be safe but the blonde beauty didn't even stir for a second.

"Now Quinn, if you don't me to finger you then speak up now," JACOB said to the unconscious girl. "Besides, it's win-win for you. This keeps me awake so that we don't drive off the road, plus you get some pleasure from it."

Not waiting a second longer, Jacob pushed his middle finger into her pussy and was surprised that his touch had her wet already. Using the lubrication to work his digit deeper into her, it wasn't long until he added a second to Quinn's tight hole.

"Uhh," Quinn lightly moaned.

Her groan had caught Jacob by surprise so he stopped pumping her pussy out of reflex. Once he assessed that the cheerleader wasn't awake and that her moan was done subconsciously, the eager boy carried on thrusting his finger into her damp opening.

Never satisfied with the status quo, he added a third finger into her tight pussy. She moaned again for him, this time a little louder than before but still kept her eyes closed. Jacob loved the feeling of having her delicate hole stretch around his fingers.

"Only sluts can take 4 fingers into their pussy Quinn. I should have no chance doing that with you, should I? You're a member of the celibacy club and you parade around as a good girl. Let's see if you're a whore or wholesome," Jacob asked.

Jacob stopped driving his hand into her pussy for a minute so that he could manipulate his wrist to get his four fingers lined up with her hole. Starting with his dry digit, he added it into her loosen opening before adding a second and third finger. Applying more pressure, he was shocked when her pussy yielded and accepted his fourth digit.

"Slut! I knew it," Jacob celebrated. "Maybe it has something to do with the runt you had last year but then again, you should have tightened back up afterwards."

He continued to drive down the dark highway while fingering his helpless muse with all four of his fingers. However, after each passing minute he found himself growing hornier. He was even sporting a massive erection and he decided to do something about that now.

The nearest exit was only a quarter mile up the road so once Jacob got there he slowed down and exited the highway onto some rural sideroad. Driving down a little ways, he was relieved to find a run-down house that couldn't have been inhibited.

"Just going to have a bit of a rest stop," Jacob said to the sleeping beauty as he parked in the driveway and shut off the car.

Getting out of the vehicle, Jacob walked around to the passenger side and opened Quinn's door. Making sure to be gentle with the sexy cheerleader, he undid her seatbelt then moved her from the front seat into the more spacious backseat.

"Despite what you probably think, you're going to be the first girl fucked in my SUV," he told her.

Placing her on her back, he reached up under her dress and pulled her thong down her legs before resting them on the front seat. He knew he'd have to get her put back together so she wouldn't know the things he was about to do to her tight teen body.

Jacob quickly got down his pants before lifting her legs up onto his shoulders and moving tight to her. Disregarding to use a condom, he rubbed his swollen head through her folds to get it slick before placing it against her opening and pushing in. The nerdy boy was a virgin and the fact that he was on the verge of losing his virginity to the hottest girl in school was enough to overlook the fact that she was unconscious.

"Ungghh," Quinn moaned as his thick cock penetrated her.

"I thought you'd like a good hard dick in you," Jacob taunted the sleeping blonde.

With Quinn already wet from his finger work on her pussy from earlier, his member was having no problem gliding smoothly into her. After several short thrusts he had half of his length in her before he started drilling deeper to get the rest in. Finally after feeling her hole stretch over his unprotected tool did he get all 9 inches inside.

"I hope you like it deep baby," Jacob told her.

Now that she had loosened up, Jacob was really hammering into her pink opening. Each and every time his hips smashed into her pelvis caused her good-sized tits to giggle from still within her dress, spurring the horny boy on further.

Deciding that he wanted to have more leverage so that he could really ram into the sleeping girl, JACOB pulled out of her wet pussy. Reaching into the front of the vehicle, he pulled the latch that made the driver's seat descend into the backseat fully.

"And now you'll just rest like so," Jacob said to her as he re-positioned her.

With her chest and head now resting on the reclined chair, Quinn's heart-shaped ass was now pointing up at him. He wasted no time in getting his cock back into her pink hole and plowing strongly against her plump cheeks.

"You have such a nice butt Quinn," he told the unconscious girl. "I'm really appreciating the view from back here."

While Jacob continued to powerfully guide his tool into Quinn's moist opening, the horny boy reached down and grabbed a handful of her amazing ass. Ever since he first laid eyes on the doe-eyed beauty he wanted to know how her supple butt felt.

As he looked down again to admire her backside, the boy with the afro noticed how tight the girl's asshole looked. He had watched porn a lot and he had to admit that anal sex always excited him the most. Problem was, no girl he knew would let him try it out on them.

"I'm dying to ask you a question blondie," Jacob joked. "Would it be okay if I fucked you up the ass? Really? You don't mind! You've actually been dying for me to do it? Well then I'll be a gentleman and oblige your desires."

With his cock well lubed from her pussy juices already, the nerdy teenager slid his cock up an inch so it was now lined up with her constricted rosebud. He got such a thrill just seeing his tip pressed against Quinn's asshole that he almost came right then and there, but he had much greater ambition for this evening. With one hand on the base of rod and the other on her hip, he pulled the blonde towards him while pushing his own pelvis forward.

"Owww," Quinn groaned sharply as the overweight boy penetrated her virgin asshole.

Jacob knew he was too far along to stop so he hoped that the sedative she was under held up and kept her sleeping even during her first sodomy. With the first inch of his pole inside her rectum, he slowly added another. It was tougher then he figured it would be as her backdoor was clearly not very accepting of something the size of his rather wide penis.

"Don't worry Quinn. I can take my time. We have a lot of time together so I'll eventually loosen you up," Jacob told the unconscious girl.

By the time that Jacob had gotten balls-deep in the object of his affection, Quinn had nearly whimpered the whole time. He didn't care much, although he did take it very slowly and tried to cause her as little pain in the process. His first thrust into her anus after entering her fully was much easier and it was also the first time she hadn't grunted. Taking it as a sign that the cheerleader was now warmed up, the sweaty boy increased his speed so that he was now pummeling into the gorgeous girl from behind.

"Shit so...tight," Jacob moaned, feeling his orgasm approaching at light speed.

No sooner had he told her that when he could feel the pleasure get the better of him and now that cumming immediately was evident. Thinking through all the options in his head, he decided that cumming in her ass wouldn't be the best idea as she'd be able to see the evidence of what had happened while she was sleeping.

Pulling out of her ass, he took half a second to admire how gaped the formerly tight hole was before flipping the blonde onto her back and straddling her waist. Placing just the tip of his penis between her plush lips, the horny boy shot his salty load into her mouth. It felt like 10 years of sexual frustration had blasted out of Jacob's body and plastered the back of the girl's mouth. Out of reflex, Quinn swallowed down his warm liquid offering, her eyes remaining pasted shut the entire time.

"That was amazing," Jacob commented while recovering from losing his virginity. "And don't pretend like you didn't like it either slut."

After taking a minute or two to rest after the best orgasm of his life, Jacob got them both looking the same as they did before the little detour. Moving her carefully, the boy placed Quinn back into the front seat before driving back onto the highway. Knowing he had to make up the 30 minutes he just spent fucking the cheerleader, Jacob stepped down on the gas in an attempt to not have the girl become suspicious.

* * *

"Ummhhhh," Quinn moaned as she woke from her nap.

"Morning sleeping beauty. Did you have a good sleep," JACOB asked.

"Wow. I slept like a log," she answered. "Do you think we'd have time for a quick pit stop?"

"Yeah probably. Need to pee or something," he asked.

"Not really. I just need to stretch. My ass is killing me for some reason. I guess these seats aren't overly comfortable for long periods of time," Quinn replied.

Jacob nearly laughed aloud after hearing the comment from the sexy cheerleader. He caught himself in time so that he alone knew why there was a burn in her backside. He was able to make up for the two extra pit stops that he didn't envision when he originally planned out his trip, but he also didn't see himself sodomizing Quinn so he risked the consequences of speeding.

"Thanks again Jacob. I have no idea how I can repay you," Quinn told him as he dropped her off at her sister's house several hours later.

"Call it even," Jacob replied.

The cute blonde flashed him one final smile before turning her back to him and walking away from the vehicle. Jacob watched her ass intently, still wanting to steal every glance of her well-formed behind as possible before she disappeared out of sight. The cheerleader even gave her ass a little wiggle for him, knowing that he'd be watching as a last thank you for him helping her out. Just as she went into the house, Jacob could tell her ass was still burning after her first anal sex as she was walking like she'd just gone horseback riding.


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