College Prep Ch. 01

"And so in conclusion, my fellow graduates of Sacred Hearts Preparatory High School, we go off to college and out into the world with all of the knowledge that we acquired here. And I know that each and every one of you, with the help of our God, will be successful in whatever you set your mind to. And we will be the future leaders of this great country!"

A rousing cheer went up from the crowd of students, friends and family in the school gymnasium as Holly completed her valedictorian speech to the graduating senior class. She waved and then took her seat next to Sister Gabriella, the head nun at the catholic school. The ceremony wrapped up a few minutes later, and after another big cheer everyone made their way to the exits.

Outside, Holly found her mom. Holly gave her a brief hug as her mom congratulated her on an excellent speech.

"That was great Holly! I'm so proud of you!" her mom said.

"Thanks mommy. It wasn't a big deal. Anyway, I need to get going. Dad is taking me out to dinner," Holly replied.

"Oh, ok. Umm, Friday is your eighteenth birthday, do you want to do something?" her mom asked.

"Umm, I don't know. Dad said I could invite some friends to his house."

"Oh. Well maybe this weekend?"

"I don't know. Maybe. I have to go, though," Holly said tersely. After another quick hug Holly headed back into the crowd to find her dad as her mom headed to the parking lot.

Before she reached her dad, Holly felt someone grab her arm and spin her around. She almost dropped her yearbook, which she was carrying in hopes of getting a few last people to sign it. She discovered that it was Derek that grabbed her. Derek had also just graduated, which was a surprise to most everyone, including Holly. He'd been a troublemaker his whole time at the school, perpetually in detention, and never seemed to pass any of his classes. His parents donated money to the school and paid Derek's tuition to the private school, though, so the school staff put up with him as best they could.

"Hey Holly! Great speech!" he said cheerfully.

"Oh, umm, thanks Derek." Holly didn't care much for Derek. She was at the top of her class, he was at the bottom. Because of that she didn't feel it worth her time to be nice to him, and she was a little annoyed at having to actually talk to him now. Still, he was pretty cute in a rugged sort of way, and though she would never admit it she felt an odd attraction to his bad boy persona. Derek had matured very early. When he was a freshman he could have passed for a senior. And now four years later his body had filled out and he looked mature beyond his eighteen years.

"So I was thinking, I won't be seeing you around school anymore. Why don't you give me a call sometime, we can chill," he said.

"I, umm, I don't know," she responded. She wasn't used to being asked out, and she briefly considered whether someone had put him up to it as a joke. She spent most waking hours studying, doing homework, and volunteering for various church events and charities. The truth was that most boys sensed that Holly felt she was better than them. It's not that she was unattractive. She was 5 foot 5 inches tall, with a pretty face and long curly brown hair. Her body could best be described as average, however. She wasn't fat or thin, but because of her lack of physical activity she couldn't be described as athletic either. To top it off, her 34 B-cup breasts offered nothing to help her stand out with the boys in school. She hesitated, not sure what to say to him.

"Here, let me sign your yearbook," he said and grabbed it from her before she could protest. He quickly flipped to the page with his picture. "To the hottest fucking chick in the school," he mouthed as he wrote.

When she realized he was actually writing that she shrieked and tried to get her yearbook back. He turned away from her and finished by writing his phone number below his picture.

"There you go. Call me anytime," Derek said as he closed the yearbook and handed it back to her. She grabbed it and glared at him, furious about what he wrote.

"I have to go," she tersely replied and quickly turned away from him to find her dad. Derek just smiled as she walked away.

*****

Two weeks later Holly was spending the required weekend at her mom's per the divorce agreement that was negotiated four years ago. She'd turned 18, so now it was really up to her if she wanted to live full time with her mom or dad, she just hadn't gotten around to bringing up the subject. Of course she'd rather stay with her dad full time, but then she also was heading off to college out of state soon, so she figured she'd endure the shared custody for another two months.

She'd never forgiven her mom for divorcing her dad, putting all the blame on her and none on him. Her mom had raised Holly as a good catholic girl, and Holly took all the teachings to heart. Divorce was wrong, but her mom was ignoring that and was only thinking about herself. On top of that, now her mom had a boyfriend. His name was Barry, and they hung out in her mom's bedroom all the time. The walls were thin enough that she heard way more than she wanted to, with the two of them giggling and doing other things that she didn't want to know about. She was certain they were having sex, which was another sin.

Tonight was no different, and Holly was fuming. Her mom and boyfriend were in their room watching TV. The TV wasn't loud enough to drown out their senseless laughter, though. She needed a way to get back at her mommy, teach her a lesson. And then an idea formed in Holly's head. She grabbed her yearbook and picked up her phone. Without thinking she punched in the number.

"Hello?" came the voice at the other end of the phone.

"Hey, um, Derek, how's it going? It's, umm, Holly," she stuttered. She'd called without putting much thought into what to do next.

"Holly! Hey babe, what's up? How's your summer vacation going?" Derek asked.

"Oh, it's ok I guess. It's such a bore here at my mommy's house."

"Yeah, I know how that goes. You want to get together? We could listen to some tunes, there's this new band you might like," Derek said.

"Yeah, that'd be great. Can you come pick me up?"

"Sure thing, give me twenty minutes."

Holly hung up and rushed to her closet to find something better to wear. She frantically emptied half of her closet before she finally picked out a silky blue top. She didn't know why she was acting this way, it was very unlike her to go out of her way to get the attention of a boy. Just as she walked back to the living room wearing the top she saw the lights of Derek's truck pull into the driveway.

"Mommy, I'm going out for a bit!" she shouted and then went out the front door without waiting for a reply. She hopped into the passenger side of Derek's truck.

"Let's go!" she said a little breathlessly.

Derek pulled out and they drove around town for a while. They talked, or rather Derek talked and Holly for the most part stayed quiet and stared out the window feeling unsure of herself. He played a couple songs from the new band that he had mentioned over the phone. She cringed a little at the coarse lyrics, but didn't say anything to Derek about it. They eventually went through the Filiberto's drive through and got a couple of sodas. Instead of driving away, though, Derek parked at the far end of their parking lot, away from the other cars and traffic.

"What are you doing? Why'd we park?" Holly asked.

"Why did you call me tonight, Holly?" he asked, ignoring her question.

"I don't know." She paused. "I hate what you wrote in my yearbook."

"Oh do you? It's true, though. You don't see it, and maybe not too many others see it either. But I do. You are hot. You just never let it out."

Holly blushed at the compliment, unable to hold on to the anger she had over his defacement of her yearbook. Derek leaned over to her and turned her face to his. "You are fucking hot, and don't let anyone tell you and different." And then Derek kissed her. At first Holly was shocked. She'd never been kissed by a boy before. But she kissed him back, and for several minutes they continued to explore each other's lips. It was nothing like how she imagined her first kiss would be, as they sat there in the truck in a dark corner of a parking lot, but even so there were butterflies in her stomach and she felt a little dizzy.

Holly felt Derek as he took her hand in his, and then placed her hand between his legs. He pressed her hand against the bulge in his pants.

"Hey! What are you doing!" Holly blurted out.

"Oh, don't give me that innocent act. I know why you called me tonight. I was watching how you treated your mom at graduation, and could tell in the tone of your voice over the phone tonight. You want to get back at your mom, and you were thinking that hanging out with a guy like me would do it."

"That's not true!" She was shocked at his accusation. Was she that obvious?

"No? I don't believe you. And maybe you are also worried about going off to college without any experience with guys. So you figured maybe I'd be a good choice. I'm not too smart, you could use me for your purposes and then get rid of me. Well, lucky for you I'm happy to help you out." Derek shifted in his seat, then quickly opened his pants and exposed his cock. Holly stared, mouth agape, unable to take her eyes off of it.

"Go ahead, touch it," he ordered.

Holly hesitated as she debated with herself. She wasn't happy that he's seen through her plan so easily. And this wasn't how she imagined it to turn out. But then her anger with her mom came back and she made up her mind. What harm could come from touching it, anyway. She slowly reached over and touched his shaft. It was hard, and yet silky soft as well. And it was sort of... well, small. She'd never seen another penis in person before, but she somehow was expecting something more substantial, more threatening. She wrapped her fingers around it and stroked.

"Mmm, that's good. You can squeeze it a little tighter, you won't hurt me," he directed.

She continued to glide her fingers up and down his shaft as he encouraged her.

"Now suck on it," he ordered.

"What? No, that's nasty!" she exclaimed.

"You want to get back at your mom? Just think how she'll flip out if she learns that her precious daughter sucked a guy's dick? Besides, it's perfectly normal, college girls do it all the time. I'm sure you don't want to be the most inexperienced girl on campus and have all the guys make fun of you."

Holly again hesitated. She wasn't sure she was ready, and she didn't know how to do it. Besides, what did he know about college girls? But he was probably right. She was going to go off to college and she'd heard enough stories about what went on there. And as she sat beside him she had an unexplainable urge to do as he asked.

"Go on, just put your mouth on it," Derek encouraged.

She took a deep breath and leaned over into his lap. She gingerly stuck out her tongue and licked. It wasn't horrible, she decided. She licked again. And then she put her mouth over it.

"There you go, that's good. Now close your lips around it. But don't let your teeth touch it," he directed.

Holly swirled her tongue around the tip of his cock and slowly rocked up and down with her lips. It took her a minute, but she eventually got into a rhythm. Derek continued to encourage her with groans and additional instructions.

After several more minutes Derek blurted out, "Yeah babe, that's it! Don't stop!" He grabbed the back of her head and pushed her down onto his cock. Holly squealed and tried unsuccessfully to get away. Then his cock erupted. Several blasts of cum hit the back of her throat and filled her mouth. She panicked, not completely sure of what just happened.

Derek finally let go of her head and she sat up. Cum dripped from her chin and landed on her top. More cum was still in her mouth, and she didn't know what to do. She wanted to spit it out, but didn't want more of it on her top. She reluctantly swallowed, gagging at the strange taste and texture. She looked over angrily at Derek.

"Why did you do that?" she yelled.

"What? That's what's supposed to happen! And you did great, at least for your first time!"

She turned away from him and stared out the window. "I want to go home now," she said, sulking. Instead of feeling satisfied with her successful revenge on her mom, she just felt used.

"Ok babe, if that's what you want."

Derek drove her home and she jumped out of his truck without saying goodbye. He called out to her.

"Hey, thanks for the good time. Talk to you soon!"

She rushed into the house only to run into her mom and Barry in the living room.

"Where have you been!" her mom angrily asked.

"Nowhere. Just hanging out with a friend," she replied tersely.

"What friend? Where did you go?"

"Just a guy from school. We just drove around. Not that you care," she replied. "I'm going to my room," she said and brushed past them. As she did Holly noticed the cum stain on her top, and she was certain that her mom saw it too. She made it to her room before her mom could say anything, and she closed the door.

After a moment Holly smiled. "Well, that went well," she said to herself. She looked down at her stained top again. "Damn it!"

Later that evening her phone rang. It was her best friend Crystal.

"Hey, what's up?" Holly asked.

"Not much. Bored out of my mind here at home. At least my mom and stepdad aren't fighting tonight. What are you up to?" Crystal asked.

"Not much, just hanging out."

"Hey, I wanted to ask you, have you heard from Derek?" Crystal asked.

"What??? Why..." Holly stuttered, stunned that Crystal would bring up his name.

"Relax! I was just wondering. I saw him the other day. He was asking about you, said he thought you were hot. It sounded like he was really in to you. He wanted to know if you had a boyfriend."

"He did? I guess that's why he..." Holly hesitated.

"He what?" Crystal asked. "Fuck, you saw him, didn't you? Did you go out? Tell me!"

Holly cursed under her breath. She wasn't sure she was ready to tell her friend about what happened tonight. "I, umm, yeah... I saw him tonight. He came over and we drove around."

"No way!!! You had a date with a guy and you didn't tell me?"

"No! It wasn't a date, exactly. We just drove around for a while. And then he took me home." Holly hoped Crystal didn't press for more details. Her hopes weren't answered.

"Just drove around? That's it? I don't believe you. Come on, tell me everything. I know you, you're holding back on me," Crystal replied. Holly cringed, embarrassed about what had happened with Derek. But she knew Crystal wouldn't stop until she got the whole story.

"Well, I sort of, umm, touched him..." Holly stammered.

"What!!! Holly Anders! As in you touched his junk? Tell me more! Was this skin on skin contact?"

"Umm, sort of," Holly squeaked.

"Sort of! What's that supposed to mean?" And then Crystal gasped. "Oh... my... god!!! Did you give him a blowjob???"

Holly blushed bright red. "Yes," she whispered. She pulled the phone away from her head as Crystal screamed at the other end.

"No way!!! You? That is just unbelievable! Tell, me what was it like? Give me details!"

Holly proceeded to tell Crystal about what she did. Crystal kept grilling Holly for more intimate details.

"How big was he?"

"Umm, I don't know, not very big I guess."

"Did you swallow?"

Holly blushed. "Yeah, umm, some of it."

"What did it taste like?"

Holly blushed even more. "I don't know, it was strange. Not terrible I guess."

"When are you going to see him again?"

"Umm, I don't know. We didn't make any plans."

"Oh my god, Holly Anders! My little girl is growing up! I'm so proud of you! Now if you see him again you have to promise to tell me all about it, ok?" Crystal asked.

"Umm, I guess so," Holly answered.

*****

Holly managed to avoid her mom all day Saturday. She slept in until 11, and by then her mom was off running errands.

Holly finally got around to taking a shower at 2pm. She washed her hair and then lathered up her body. As her hands slid over her breasts she was surprised by an odd tingling feeling. She rubbed the soap into her breasts again, and again felt the same strange tingling. "What the..." she mumbled. She looked at them, they seemed to be the same, though her nipples were maybe a little harder than she remembered. She decided it was nothing, and finished her shower.

All day Holly's thoughts strayed to what happened with Derek the previous evening. She couldn't believe she actually had his penis in her mouth. And then when it squirted, that was so disgusting. And yet she couldn't stop thinking about how it felt, how it tasted. Around 5pm her mom knocked on her bedroom door. "I'm going over to Barry's for a while. There's some leftovers in the refrigerator, help yourself to whatever you find," she called through the door.

"Ok mommy."

Holly tried to read, but found that at the end of every page she couldn't remember a word of it. At around 8pm her phone buzzed.

'Hey my sexy babe, I want to see you. I'll be by in a few minutes.'

"What!" she shouted at her phone. "No! He can't just show up!" She texted him back.

'I'm sort of busy, tonight's not good'

His reply:

'Nonsense. You've probably got your nose in a book. You need some company.'

"Damn it!" She debated not answering the door when he arrived. But another part of her was excited that a boy actually showed interest in her. She jumped out of bed and once again scrambled to find something suitable in her closet. She finally chose a white button down top. It was really more of a school uniform shirt, and she lamented that most of her closet was filled with similar clothes. She hadn't even finished buttoning it when the doorbell rang. She rushed to answer it.

"Hey babe! You look hot!"

"You can't come in..." she started to say, but he pushed past her into the house.

"I didn't see any cars in the drive. You're home alone?" Derek asked.

"Umm, yeah, I guess. My mommy should be home any minute," she lied. She was a very bad liar.

"Mmhmm," he replied. "So what do you want to do? Watch some TV?"

Holly really wasn't comfortable with him here in her house, but before she could say anything he was sitting on the sofa and had the TV remove in his hand.

"Come on, sit next to me, babe."

Not knowing what else to do, she sat down at the other end of the sofa.

"No, no, no. Next to me!" he said and grabbed her arm and pulled her over next to him.

Holly sat nervously as Derek picked out a show to watch. He put down the remote and then put his hand on the top of her thigh. Holly squirmed but didn't stop him.

"So how has my sexy girl been today? Thinking of me, I hope?" he asked.

"Umm, I'm ok. Just a boring day. I hate staying here at my mommy's house. Especially when her stupid boyfriend is here."

"Yeah, I can relate. My parents' divorced a long time ago. But they both pretty much ignore me anyway. Even worse is now my stepdad tries to pretend like he's my dad and orders me around. He's a real dickhead." Derek replied.

They made small talk for a while as they watched TV for the next couple of hours. Holly was still nervous as Derek continued to touch her. He would hold her hand, or put his hand on her thigh, or reach over and brush her cheek. She was afraid of how far he wanted to take this. There was no way she was going to lose her virginity to him. But she had heard that that's all that guys wanted. As she was struggling with these fears, Derek leaned over and kissed her on the lips. His lips were soft, and he kissed her gently. Despite her fears she couldn't resist, and kissed him back.

They explored each other's lips and tongues. Derek broke off the kiss and then began kissing her neck. A shiver went through Holly. The same strange tingling she felt in her breasts earlier returned. As he continued to kiss her neck and ear, that tingling moved lower and she squirmed. Derek moved a hand up her side until it reached the side of her right breast. His thumb stroked her through her bra, just an inch from her hardening nipple.