Jonathan's College Prep

Story Info
His cousin teaches him what he needs to know for college.
6.9k words
4.72
54.8k
62
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Leader12
Leader12
980 Followers

Jonathan woke up as the car pulled off the highway. They had been driving for just under two hours, and he enjoyed getting some extra sleep. He pulled a piece of gum out of the package in his pocket to freshen his breath after his nap.

He loved it when they'd visit his aunt, uncle and cousin. They lived close enough to see them many times throughout the year, but far enough away that they'd spend a long weekend staying at their house when they visited.

Jennifer was his only first cousin, and she and he were always close. She was six months older than he was but was a year ahead in school because of when their birthdays fell. She had just completed her first year in college; he would be leaving next month for his first year. The last time he visited his aunt and uncle, Jennifer was at school, so he was really looking forward to seeing her today.

Only ten minutes after getting off the highway, the car pulled into his aunt and uncle's driveway. As soon as he opened his door, Jennifer came running out, threw her arms around Jonathan, and gave him a big hug.

"Jonny! Great to see you! I'm so excited you guys are here."

Jonathan pulled her close to return the tight hug and gave her a little kiss on her lips.

"Hey, Jennifer. Great to see you, too. I missed you last time we came."

"I know. College! I HATE when it gets in the way of my having a good time!"

Jennifer turned away from Jonathan to greet her aunt and uncle, giving each a kiss on the cheek. Her parents walked out of the house, and the whole greeting process was repeated. Everyone gave each other a hug, and everyone kissed the air as they placed their faces cheek to cheek.

Jonathan thought Jennifer looked fantastic in her white tank top and jean shorts. She was clearly in good shape, and her tank top hugged her torso and her perfect, small breasts. Her stomach was flat, and it didn't look like she had an ounce of fat on her.

"Geez, cuz, I thought you're supposed to put on the freshman 15 your first year at school. You look great!"

Jennifer laughed. "If you had seen me after my first two months at school, you woulda thought I was gonna be adding way more than just 15 pounds. I was eating tons of crap, didn't exercise at all, and looked like shit." Suddenly, she covered her mouth with her hand. "Sorry, Aunt Linda, I didn't mean to swear."

Jonathan's mom gave her a stern look for three seconds, and then started laughing. "God damnit, girl, you think I'm a prude? You're in college. If I didn't hear you say bullshit every few sentences, I'd get nervous you weren't normal."

Jonathan's eyes went wide open and his mouth opened in shock; he never heard his mom swear. His mother turned toward him.

"Close your mouth, Jonathan, and don't be so shocked. I know all the words. And you're not always so quiet on the phone when you're talking to your friends. Jesus, Bob, I'd better start swearing around the house a little more."

Now everyone was laughing as they grabbed the bags and started walking up to the house. Jennifer continued with her explanation.

"One morning I went to put on some pants, and they were tight. I looked in the mirror and realized how horrible I looked. I decided right then and there that I had to take better care of myself. There's a great fitness center on campus, and I started going 4 or 5 times a week. I feel so much better now. I almost have withdrawal on days I can't go."

"Well, whatever you did worked," Jonathan said. "You look fantastic!"

"Thanks, Jonny."

Jonathan always thought his cousin was pretty, but about three years ago, as her body started to mature, he realized she was beautiful. He never thought about her sexually, but he knew she had a body and a face that would attract any guy. But to him, she was just Jennifer -- his buddy, his playmate, his confidante.

He was also always amazed at how much Jennifer looked like her mom. Though she was in her 40s, she looked fantastic, with the same pitch-black hair, slender body, small, firm breasts, and hazel eyes. Her face was an older version of Jennifer's. Of course, Jennifer didn't look anything like Jonathan's Uncle, since he wasn't her biological father. Jennifer's dad was killed in a car accident when she was less than a year old. Two years later, her mom married Jonathan's uncle.

When he was younger, when they visited, he'd sleep in the second bed in Jennifer's room. Somewhere along the way -- maybe when she got to high school -- he started sleeping on the couch in the living room. He would have been fine sleeping in her room, but he figured she'd feel uncomfortable. So, one year he just suggested he should sleep on the couch, and it continued that way every year.

Jennifer's parents had set up lunch outside on the deck. It was a perfect day for eating outside: warm, but not hot, with a gentle breeze. There wasn't a cloud in the sky, and the patio umbrella kept the sun off of them. As usual at the beginning of every visit, there was never a quiet moment. Everyone was constantly talking, often with multiple conversations at the same time. And there was lots of loud laughter. The adults all got along fantastically, as did Jonathan and Jennifer. When they weren't listening to their parents' conversations or answering their questions, they were talking to each.

Jonathan wanted to know everything about Jennifer's first year at college, and she wanted to know all about his upcoming year. He was going into engineering, being really good in math and science in high school. Jennifer couldn't answer any questions about what engineering was like, but she talked a lot about campus life in general.

Jonathan couldn't ask her about the one thing he really wanted to know about college life: how much sex did people have? Not only was he a virgin, he had never even touched a girl's breasts. He never dated and was very shy around women. Of course, he wasn't shy around Jennifer, but she wasn't a girl, she was his cousin and his friend.

They spent the entire day outside just catching up, telling stories about Jonathan and Jennifer's grandparents, and telling funny stories about how Jennifer's dad used to tease Jonathan's mom when they were kids. At one point, Jonathan just sat back and smiled. His mom and uncle were incredibly close, and he loved watching them when they got together. All of the people sitting at the table were the most important people in his life, and he always felt loved when they were all together.

As the sun started to hide below the trees off in the distance, Jonathan's dad started laughing.

"It happens every goddamn time we visit." Looking toward his wife and brother-in-law, he continued, "once you two start talking and telling stories from the old days, you never stop. If I didn't stop you, we'd probably miss dinner. And goddamn it, I'm hungry!"

Everyone started laughing -- especially Jennifer. She had an infectious laugh, and the more she laughed, the more everyone else laughed louder and louder. Once she finally stopped laughing, she asked, "how about pizza for dinner? You didn't plan anything, right, Mom? Let's order from Tony's."

Her mother looked at her father, and he shrugged. "Okay with me."

"Is it okay with you, Aunt Linda? Uncle Bob?"

"Whatever you'd like, sweetheart," Linda responded. "If you want it, I want it!"

After a few minutes of negotiating what would be on the pizzas, who wanted thick and who wanted thin, and what sizes they needed, Jennifer called in the order. After 10 minutes, she turned to Jonathan.

"C'mon, cuz, let's go get the pizzas."

In the car, when Jonathan looked at Jennifer, he saw her profile. He couldn't get over what a perfect body she had. Her small breasts were absolutely perfect. He quietly yelled at himself for thinking about her body -- this is his cousin! But he couldn't help himself. She was just beautiful.

After dinner, the usual routine took place. The parents all went to sleep. Jonathan and Jennifer changed into their nighttime clothes -- usually short pajama bottoms and a t-shirt for Jonathan, and sweat pants or running shorts and a t-shirt for Jennifer. Then they would spend hours in the living room -- AKA Jonathan's bedroom for the next few nights -- watching TV and talking.

After about an hour, Jennifer turned to Jonathan and asked, "What's the matter? You look like you're confused or not feeling well?

Jonathan paused for a second, not sure if he should ask the question that was on his mind.

"I'm just thinking about a lot of things for next year, and, umm... I don't know."

"What are you worried about? Ask me. I'll help you."

Jonathan took a deep breath. "Okay." Then he paused again for a few seconds. "You said you and Tony broke up, right?"

"Yeah. A little before the end of the year."

"When you were together, did you like it when he touched your breasts?"

Jennifer let out a loud laugh, then covered her mouth when she realized how loud she had been.

"What kind of question is that?" she almost shouted, but with a smile on her face.

Jonathan turned red and didn't answer.

"C'mon Jonny -- tell me why you asked that. Not exactly what I expected."

Looking a little embarrassed, Jonathan slowly, quietly answered her.

"I've never even seen a live girl naked, let alone touched her. College girls are going to expect guys to know what they're doing. And I don't know shit about it."

This made Jennifer laugh again, though more quietly.

"Don't worry, you'll figure it out. Most guys do."

"Yeah, they figure it out in high school, and they know what they're doing in college. I'm a few hundred years behind them."

"Don't worry, Jonny. You'll be fine."

Jonathan looked down at the couch so he didn't make eye contact with Jennifer when he asked, "Can I touch yours?"

Again, Jennifer let out a loud laugh and covered her mouth.

"Umm, no, I don't think so, Jonny. Jesus, this conversation is NOT what I was expecting."

"I just want to know what it feels like so I won't seem like a moron the first time."

"You'll be fine. Besides, I'm sure you want your first time to be with a girl with real tits, not little tiny ones like I've got. You're probably looking for double-Ds."

Now Jonathan looked straight into her eyes.

"That's not true. I've seen the girls with big tits on the internet. I think the most beautiful breast size is 34 B."

"Oh, Mr. Never-seen-a-girl, you know exactly what size you like? When did you arrive at THAT conclusion?"

Jonathan got embarrassed again and looked down. He spoke very softly.

"When I looked at the size on your bra in the hamper in the bathroom."

Jennifer's brows furrowed as she stared at him.

"Jesus, Jonny. You looked at my bra in the hamper? Did you look at my panties, too?"

He didn't answer.

"Oh my God! You did!"

"I'm sorry, Jen. I couldn't help myself."

Her anger lasted only for a second. She always loved her cousin, and she realized he was really hung up about this. She knew she couldn't stay mad at him.

"Okay, stud, I think it's time for me to go to sleep. See you in the morning." She got up and walked out of the room.

"Shit," Jonathan thought to himself. "I made a fool of myself AND pissed her off. I'm such a fuck-up."

He turned off the lights and laid down.

Jennifer walked into her room, closed the door, and sat on her bed.

"Poor Jonny," she thought. "He only thinks of himself as a geek who's afraid of girls. He doesn't even realize how good looking he is." Then she thought about what he said. That her bra size -- her tits -- were the most beautiful size he had ever seen. And then she smiled.

After 5 minutes of fighting with herself, Jennifer quietly opened the door and walked back to the living room.

"Jonny. Are you awake?" she whispered.

"Yeah." He sat up and turned on the lamp on the table.

She walked over to the couch and kneeled down in front of him.

"You know I love you, right?" she asked.

He nodded. "I love you, too. Even when I do stupid things."

Jennifer smiled at him. She slowly took his hand in hers and placed it on her breast.

Jonathan gasped loudly. But he was afraid to move.

"Go ahead," Jennifer said, very quietly. "Give it a gentle squeeze."

Jonathan quickly followed her directions, gently caressing her breast. Jennifer tried to play it cool, but she realized how good it felt. And she realized her nipple was getting very hard. Jonathan could feel it, too.

Deciding to take a chance, Jonathan gently squeezed the nipple between his thumb and middle finger, causing Jennifer to let out a quiet moan. Jonathan groaned, too, not really believing this was happening. After just a minute, Jennifer pulled away.

"You sure seemed to know what you're doing, Jonny. You'll do fine at college with the girls. Good night."

She walked out of the room, but Jonathan just sat there motionless. He could not believe what happened. "I just touched a breast!" he said to himself. "And even better, it was Jennifer's breast! And it was wonderful!" Jonathan got off the couch and walked into the bathroom. He grabbed a few pieces of tissue and walked back to the couch. He turned off the light, laid down, pulled up the covers, and slipped his hands under the covers. All he could think about was Jennifer and her breasts.

He pulled down his shorts and immediately started stroking his dick. He got rock hard in two seconds, replaying "the touch" in his mind. It didn't take very long before he had to grab the tissue and hold it in front of his dick while he shot stream after stream of cum. He wiped himself off, tossed the tissue on the table, pulled up his shorts, and rolled over with a huge smile on his face. He fell asleep quickly.

When Jennifer got back to her room, she smiled to herself. She knew she shouldn't have done what she did, but she certainly didn't feel bad about it. In fact, she felt great. She could still picture the look on Jonny's face when his hand touched her breast. And she was a little surprised when her nipple got so hard.

Jennifer got into bed and put her hand on her breast over her t-shirt -- just like Jonathan had done. She gently squeezed her breast exactly as he did. She pictured him in front of her, pinching her nipple. She let go of her breast so she could pull up her t-shirt and touch her bare breast. She used both hands to pinch both nipples, and she let out a very soft moan. She slipped her right hand off her breast, down her stomach, and into her shorts, quickly slipping a finger between her lips. She was very wet, and she slipped two fingers into her pussy. Again, she let out a soft moan.

She pulled her wet finger out and started rubbing her clit. She was breathing very hard as she continued to pinch her nipple with her left hand and quickly stroke her clit with her right hand. She licked the fingers on her left hand and went back to squeezing her nipple. Like Jonny, it didn't take very long to start feeling an impending orgasm.

She started bucking her hips up off the bed, grunting but trying not to be too loud. She rubbed her clit even faster, and suddenly her hips lifted off the bed and just stayed in the air. Then she collapsed to the bed. She continued to rub, and it happened again, with her hips jumping in the air and holding there while the most wonderful feeling took over her entire body. After two more of these thrusts, Jennifer collapsed on the bed. She wiped her finger on her sheets, pulled up her shorts, pulled down her t-shirt, rolled over, and fell asleep with a huge smile on her face.

The next day was another beautiful, warm, sunny day with a bright blue sky and big, fluffy white clouds, and the family took advantage of it. They started the day having breakfast outdoors at one of the group's favorite restaurants. Everyone was talking and laughing -- at stories they told, at each other, and at other relatives.

Jonathan was glad that Jennifer didn't seem weird or angry about last night. But he couldn't get that wonderful feeling of touching her breasts out of his mind. And the fact that she was wearing a baby-blue halter top with crisscross strings in the back and white cut-off shorts didn't help him ignore thoughts about her breasts. He found himself staring at them more than he knew he should. Jennifer noticed it, too, a few times, but she just smiled to herself. She didn't try to embarrass him by calling him out.

After breakfast, they walked around an art fair. There were booths set up on both sides of the street, with artists displaying paintings, jewelry, wooden bowls, and blown glass. A few times, when Jennifer was walking in front of him, Jonathan noticed how nice her ass looked.

"Jesus," he thought to himself, "why am I looking at my cousin this way. I always knew she was beautiful, but I NEVER thought about her body like I'm doing now!" Of course, he knew the answer. Once he felt her breasts, he couldn't help but think of her a LITTLE differently.

They grabbed some vendor food from the art fair and sat at picnic benches that had been set up. Everyone was having a wonderful time, and it was clear how much they all loved each other.

They spent a couple of hours listening to two bands that were playing just outside the art fair, grabbing some ice cream cones while the old band removed their equipment and the new band set up.

For dinner, they ended up at another outdoor restaurant. More stories brought even more laughter, though some of the laughter was partially enhanced by the wine everyone was drinking. As they were walking home, Jennifer's parents, who were up front, started to hold hands. Then Jonathan's parents, who were right behind them started to hold hands. Jennifer and Jonathan were in the back. With a smile on her face, Jennifer grabbed Jonathan's hand and started swinging it high -- forward then backwards, and she giggled as they held hands the rest of the way home.

As soon as they walked in the door, the parents said they were going to sleep. Jennifer said she was tired, too, but was going to take a shower before going to sleep. Jonathan asked if she wanted to watch some TV after her shower, but she said she was exhausted and was going to go straight to bed.

Jonathan wasn't sure if she was REALLY tired or if she just wanted to avoid any more embarrassing questions from him. She certainly didn't indicate she was upset with him today. In fact, quite the opposite. She seemed to have a good time with him all day. He tried to not worry about it, but it was still in the back of his mind as he eventually closed his eyes and drifted off to sleep.

In the morning, Jennifer, her parents, and her aunt and uncle were sitting around the table having breakfast. Jonathan was still sleeping.

"Your mom's taking me to her favorite antique store today. Do you want to join us?" Aunt Linda asked.

Jennifer's mother let out a loud laugh just as Jennifer made a face as if someone had farted.

"I think she'd rather go to the dentist and have three root canals!", her mom said. "Not exactly her thing."

"How about Jonathan?" Jennifer's father asked. Looking at his sister, he said, "Bob and I are going fishing at the lake. Will he join us?"

Now it was time for both of Jonathan's parents to let out a laugh.

"I think he'd rather join Jennifer and get those same root canals," Jonathan's father said. "I don't know where I failed him. My grandfather took my father fishing, and my dad loved it. My dad took me fishing, and I loved it. I took Jonathan fishing, and he absolutely hated it."

A couple of minutes later, Jonathan crawled off the couch and walked into the kitchen. He looked like his hair got caught under a fan and his nearly-closed eyes had glue stuck in them. He rubbed his eyes, trying to pry them open.

"Lots of laughter in here. What's going on?"

"Great news, Jonny," Jennifer said. "My dad has arranged an all-day fantastic adventure for you. He spent a lot of money on this and has planned it for weeks, but he said it would be worth it to see your face when you heard. You, your dad, and my dad are going on an all-day, unbelievable fishing trip. Just a bunch of fishermen out on a big boat with no distractions. Nothing to do but fish." She flashed a huge smile at him as she continued, "You are one lucky guy!"

Leader12
Leader12
980 Followers
12