Unconditional Love Ch. 01

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Jack finds love in the most unexpected place.
17.1k words
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Part 1 of the 4 part series

Updated 06/10/2023
Created 07/05/2020
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daemonrunner
daemonrunner
1,447 Followers

Greetings all. This is a story that came to me while I was working on the Domination series and seemed to build itself while I was writing it. Please enjoy:

Note 1: Thank you to WA001 for his time and effort in editing this story

Note 2: For those of you with a Grandma fetish, this will be right up your alley :)

Note 3: Some of you may notice at the end of Chapter 2 and beginning of Chapter 3 some similarities to a story from Soul71. This was not as a way to replicate his story but just how the story played out. Though I have spoken to Soul71 and he let me know to publish as is instead of changing it. This story was written of my own accord without using inspiration from another, it just came out as a coincidence.

Without further adeu, please enjoy the story.

All participants in this story are 18 years old or older.

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Love is a beautiful thing. When you fall in love, it is the most wonderful feeling. For most people, they only have one person whom they truly fall in love with. For others, they are lucky to fall in love with more than one person.

For Jack McKalister, he did not know love yet. He was a normal 18-year-old teenager but had only had one steady girlfriend and their relationship only lasted four months. He did have a couple friends and was more into playing video games than chasing after girls. Both of his friends currently had girlfriends thereby limiting their gaming time, so Jack was stuck playing with people he didn't know and most of the time, didn't get along with.

Growing up in his house was odd at times. Having a perfect "10" sister who was three years older than him and a perfect "10" mother was hard on Jack sometimes, especially when those pesky hormones would perk up. However things got much stranger after he turned 18. Like when his sister would be tanning out by their pool and Jack would sneak peeks at her. Blair, his sister, would constantly remove her top when she was out tanning and for some reason, she would always make sure the lounge chair was facing the house. This would give Jack an excellent view of her perky and tanned breasts. Top that off with the way her light brown hair would come down to her breasts and it would land as silk strands on her breasts and she would remove them in the sexiest way possible.

Blair was not what one would be considered thin but she wasn't considered fat either. She had some thickness to her. Her medium sized C breasts were perky as can be and her thick thighs and ass were just what Jack liked in a woman. It was too bad she was his sister. However, that would not stop him from jerking off two or three times a day while thinking about her and definitely when she was out back tanning. To this date, she had never caught him that he was aware of, but then again, he wasn't that slick all the time as well.

On top of his sister, his mother would constantly wear outfits that would show off the cleavage of her large breasts. Janet, Jack and Blair's mother, had long wavy blonde hair and fair to almost pale skin. One could easily tell that Blair's thickness came from her mother, though part of it was from having two children on Janet's side. Watching his mother and sister walking around half-naked some of the time would cause any male to be in a constant state of arousal.

The two ladies of the house did not always dress so provocatively. Prior to Blair turning 18, she acted like any standard teenager and Janet would dress more conservatively. A few months after Blair turned 18, something changed that Jack could not figure out. They acted the same and never treated him any differently, but their attire had taken a change for the slutty, at least around the house. When they would go out, either as a family or alone, neither Janet nor Blair would dress as provocatively. Jack had partially thought that maybe they were doing it for him, but if that were the case, why wouldn't they say anything or explain their actions as to why they were dressing like this now? Either way, it just helped to enhance Jack's stroke sessions and ended there.

Jack was only a few days away from graduating and had his grandmother to thank for him having a current 3.6 GPA. She had helped to tutor him through most of his harder classes. He was not taking anything too seriously hard but wanted to make sure to ace them all so that he could get into a good college. Currently, he had a couple offers but since he was not going for anything having to do with sports or any other extracurricular activities, they had given him until the end of graduation to make his decision. He was deciding between UGA, UT and USC (University of South Carolina and not California). Only UGA was in state and closer to his home but if he genuinely wanted to stay at home, he would probably have to go to a much smaller university. Both of his friends were going to the local university, just like his sister was. UGA would only be an hour drive and he could still live from home and it would allow him to go to a major university and somewhat live the college life without having to pay for the dorm room.

After his graduation, his parents hugged him and congratulated him. He also let them know he took the offer to go to UGA the day before. His parents gave him a $1000 graduation gift as well. Though he was happy with the gift that his parents gave him, he was surprised that he didn't get his first car like his sister did when she graduated. Jack was already planning on getting a job over the summer to allow him to purchase a car to be able to drive to UGA, but he did half expect his parents to help with it.

Once his parents were done congratulating him, his sister stepped in and gave him a hug. She had a look in her eyes that partially scared him as it was one that he had not seen before. It was a look of primal lust that forced him to swallow hard. When she wrapped her arms around him, he could feel her soft breasts pressing into his chest. She also held him tight to her chest, pressing her crotch against his as she bit her lip loving the feeling of the man in her arms.

"Congrats little brother on graduating. Too bad you aren't going to school with me. Otherwise I would be able to show you what college life is really like," Blair said before running her tongue over his ear lobe before nibbling softly on it.

Jack instantly pulled back from the hug and looked at his sister wondering if he woke up in the twilight zone or if this was some odd movie he was watching.

The confused and fearful look in his eyes was caught by his mother who spoke up, "Something wrong honey?" Janet asked as she came up on his side allowing his arm to rest in her generous cleavage, making sure he felt how soft and yet still firm her large breasts were.

Jack took a few steps back before shaking his head, hearing his mother and sister giggling at his reaction. "This is getting too weird for me. I'm going out with some friends to celebrate and will be home late so don't wait up for me."

With that, Jack started to head away before his mother called out to him, "Jack! We were going to take you out to dinner though!"

Jack could hear the disappointment in his mother's voice and turned back to see tears starting to form in his sister's eyes. He couldn't understand why she would be so upset that he would want to spend time with his friends on graduation day. It wasn't like they were that close. They were about as close as any two siblings that were friendly with each other, but not the best of friends and would almost never hang out, unless she wanted him there for something.

He could only respond back with, "Sorry, but I gotta go." With that, he ran into the crowd to find his friends. He didn't really care about hanging out with them as they would most likely be spending the time with their girlfriends, but he didn't want to spend this time with his parents.

Jack was able to meet up with his friend who would give him a ride to the movie theater. His friend asked him why the movie theater and Jack would only respond with, to get away from my odd family. His friend's girlfriend would look at him strangely from time to time, like she was measuring him up. Jack would ignore her for the most part but sometimes it would frustrate him the way she would look at him, almost like she liked him more than his friend. However, it didn't matter to him as he would never make a move on her and to him, she was not his type. Though he didn't really know what his type was, just that she was definitely not it.

The next morning, Jack woke up around 10am. He had spoken to his grandmother after the movie the night before and she had asked him to stop by as she had a surprise for him.

He knew his grandmother didn't have much money after his grandfather had died five years prior. Both his grandparents worked for most of their lives with his grandmother retiring early to help take care of him and Blair while his parents worked. His grandfather was eight years older than his grandmother but was still working when he passed, though he was not making too much and had spent his retirement on keeping them out of debt. His grandmother was not yet old enough to get retirement and only had his grandfather's military retirement coming in to help pay the bills. Luckily for her, the house and car was paid for and her bills were quite low.

Jack jumped out of bed, grabbed his clothes and went to go shower. The door was slightly ajar, so he didn't think anyone was in the bathroom but got a huge surprise to find his sister sitting on the toilet in a sports bra with her shorts around her ankles.

"Jesus Blair, learn how to lock the door," he yelled as he saw her and started to back out and shut the door.

"If you are only coming to shower, go ahead. I'm almost done, and it is not like I haven't seen a guy naked before," she responded with a giggle.

Jack had turned his head so he was looking at the wall and could only shake his head, "Seeing another guy naked and seeing your brother naked are two different things Blair."

"Yeah well, once you have seen one person naked, the rest all look the same. It is just a matter of whether you are bigger or smaller in... certain areas." She paused for a few minutes before stating, "Either way, I'm done now, and you can have the bathroom."

He heard the toilet flush and turned around to see his sister pulling up her shorts and the lack of pubic hair that she had above or around her pussy area. He also noted how she slightly parted her legs as she pulled them up and into place. His face turned red and he quickly turned his head, so he wasn't staring.

Blair giggled as she walked by him slapping him on the shoulder. Jack just couldn't understand why his family was acting odd toward him after his graduation.

Once she was gone, he shut the door and started the shower to his temperature. He didn't like overly hot showers preferring them more moderately warm. He stripped down and looked at himself in the mirror. His scrawny arms and legs and thin waist had him at a disadvantage to most other guys that were his age as most were filled out. That and he was only about 5'7" which was roughly an inch shorter than his sister. He had hoped he was going to get a growth spurt and get closer to 6' but it never happened so he was stuck being shorter than most of the guys.

As he was going to step into the shower, the door suddenly burst open with Blair coming into the bathroom, "Sorry, forgot to brush my teeth."

Jack quickly covered his dick with the sudden intrusion of his privacy, "GOD DAMMIT BLAIR! What the fuck?" he yelled.

"What? I told you before, it isn't anything I haven't seen."

"And I told you, you shouldn't be seeing your brother naked," he responded wondering why she would be okay with seeing him naked.

"Look," she said turning to him, "If it is that big a deal, I will show you mine, so you don't feel left out."

Jack's eyes bugged out of his head and his mouth dropped open at what she said. However, his eyes quickly closed as his sister flipped her top up and exposed her perky breasts to him.

"FUCK BLAIR!" he screamed out, "Would you quit that shit!" Though his response was one a family member should have when seeing another family member naked, it was his lower half that reacted oppositely. He instantly had a hard on as he had noticed how hard her nipples were and how perky her breasts were. No matter how hard he tried, his cock was rock hard, and it was hard for him to keep it covered with just his hands.

"Blair! Leave your brother alone," he heard his mother yell out from down the hallway.

"Sorry Mom. I was just trying to brush my teeth, but I guess I can wait." Blair let out a sigh as she left the bathroom and slammed the door shut.

Jack re-opened his eyes after he heard the door shut and could only shake his head at how his sister was acting. He stepped into the shower and proceeded to wash himself. Once he was finished, he was still hard as a rock and knew he needed to take care of it. He had never jerked off in the shower before but didn't want to see his loving grandmother with a hard-on.

As he stroked his cock, he tried to think of the many pornos that he had seen but the one thing that kept flashing back into his mind was his sister's wonderful breasts and the sight of her saved pussy. He closed his eyes and started to picture his sister stripping down to be bare naked and drop to her knees and start sucking his cock. The sensations he was feeling were like nothing he had felt before.

Next, he pictured himself on top of her, plowing away at her tight cunt. Feeling her lips grip him like a tight glove and feeling that velvety flesh gripping him. How her cream would coat his cock as he made love to his own sister. That thought alone shot a jolt of electricity through his body as he suddenly opened his eyes and painted the wall with his cum.

Just as the first squirt came out and he grunted loudly, his eyes went wide as his mother opened the bathroom door. "Sweetie, are you going to need breakfast or are you going to get it yourself."

Jack was breathing heavily and barely registered that his mother was talking to him. He tried to speak but his voice croaked and squeaked as he tried to say something, anything.

"Jack? Are you okay? Do you need me to help with anything?" he heard his mother say as her voice seemed to get closer.

"Y-y-yes. I-I'm okay," he managed to get out. He then cleared his throat and finished with, "Sorry, I swallowed some water and it went down the wrong pipe when I was getting the soap off."

"Okay sweetie. Just let me know if you need me to make you breakfast or not. I will be leaving soon and want to make sure you are okay."

"Alright Mom. I got my breakfast. I'm going out in a bit but will grab something before I leave okay," Jack responded.

Jack could hear his mother sigh before she left the bathroom and closed the door on her way out. His mom was always sweet like that to him, making sure he was taken care of. However, over the last two days, if he didn't let her do something for him, she would act like she was disappointed. It was like she needed to take care of him. "This could be something having to do with the last child leaving the nest and mother hen getting protective but then again, it could be something else." he thought to himself.

He turned off the shower and dried himself off. He finished up by brushing his teeth and putting on deodorant before leaving the bathroom. Making a quick breakfast, he was out the door within 30 minutes and was on his way over to his grandmother's house. Jack would need to catch the city bus and then walk a couple miles to make it to her house and in all, the trip would take over an hour.

When Jack first started getting tutoring from his grandmother, he found out that his mother and grandmother had a falling out. This started about a month after his grandfather died but Jack never knew what caused the animosity between the two women. It was then that he would say he was going to a friend's house each time he would go to see his grandmother. One thing he did know is that he did see the sadness in her eyes of not seeing her daughter or granddaughter anymore. His mother would call about once every couple months, but that was just to make sure she was alive and kicking and the conversation would only last about five minutes at most.

Prior to their falling out, Janet and her mother would talk multiple times a week and their conversations would be close to an hour or longer. Jack had asked both of them what caused the animosity but neither one would talk about it. While his mother would get angry, his grandmother would get sad and would be on the verge of crying before he would need to comfort her. Either way, he wanted to know so he could see if he could mend their relationship.

Jack finally made it to his grandmother's home and went inside. She was baking something in the kitchen as the aroma made its way throughout the house. From the wonderful smell, he could easily tell it was the homemade cookies that his grandmother perfected and his mother had tried so hard to replicate but couldn't make. More specifically, they were snicker-doodle cookies and were better than any store could make.

"Hey grandma, I'm here," Jack said announcing his presence.

She came running out of the kitchen and launched herself at him bracing him in a hug. She is a bigger woman than he is a man. Much like his mother, she has that extra bit of thickness to her with thick thighs, a big butt and a larger stomach on her. Also like his mother, she had large breasts though her breasts were easily much larger than his mother's.

She pulled back after hugging him for a few minutes, "How is my handsome graduate grandson doing?"

"I'm good Grandma. How are you doing?" Jack asked. He genuinely cared for her and also had other feelings for her that he shouldn't. She had easily been a part of his jerk-off sessions for a while. About as much as his sister. She had a smaller pool than his parents did and he was able to see her in a one-piece a couple times and even stared just a little too much when she would bend over either facing him or away.

"Good, good. Why don't you sit down and let me get you something to drink? The cookies should be ready in a few minutes." As she was just about to step back into the kitchen she turned her head and said to him with a loving smile, "You don't know how proud of you I am for graduating with such a high GPA. You have made me the proudest grandmother and I was so happy you came to me for help. Thank you for letting this old lady help you with your studies."

Jack could see tears starting to form in her eyes and got up quickly, turning her around as he embraced her in a hug. "You are definitely not old Grandma. And let me tell you that you are still a stunningly beautiful woman and any guy would be lucky to have you. Also, I could not have done it without you and I love you more than anything."

He could feel her tears soaking into his shirt as they embraced one another. After a few minutes, they separated and she wiped her tears away before heading back into the kitchen.

Jack had not told her that he was going to UGA yet but with her house being closer than his own, he could see about staying at her house on certain days when he had class to make the drive a little shorter.

After a few minutes, his grandmother came in with a plate of her famous cookies and a cold can of soda. Like most teenagers, he preferred soda over other drinks but would drink just about anything. She handed him the soda and he took two cookies from the plate before she joined him on the couch.

"So tell me how it feels to be done with high school?" his grandmother asked him while she rested her right arm on the back of the couch while she took a bite of her own cookie.

daemonrunner
daemonrunner
1,447 Followers