Disclaimer: please note the following story, people and scenarios are fictional. All characters are also over 18 years old. This is just meant for fun.
START
Jacqueline Madison lived with her son, Jackson, in a small Midwest farming town. Most people just called them Jack & Jill, like the nursery rhyme. They hated it at first, but it eventually grew on them.
Jill was a second-grade teacher at the local school and at the age of 48, she's seen many kids in the community grow up in front of her eyes and eventually leave town for better opportunities in the big city. That's what her husband, James, also did. We'll that was his justification to them. In reality he was just going through the typical midlife crisis and was longing for his younger playboy life without the burdens of a wife and child. Shortly after her 44th birthday he broke the news to her that he was moving to Los Angeles and he wanted a divorce. He moved out of their home and lives within the week. She was furious that her husband of almost 25 years could just abandon his family overnight. To speed up the divorce proceedings, he gave her the house, a fairly large sum of money in the bank and a promise to pay for Jackson's college education. A promise which he kept. He was a successful online trader for a hedge fund, so he had the money to spare.
So, there she was, single with a 19-year-old son in a blink of an eye. She didn't take the divorce well, and Jack took it much, much worse! He was a boy abandoned by his father, who almost never phoned him in the coming years. Once in a while when he remembered Jack's birthday, but for all intents and purposes he was basically dead to them both.
Jack had unfortunately developed some serious commitment issues during those formative years of his life. He had trouble meeting girls and just being in relationships in general. The constant fear of being rejected by someone he loved hanged over him like a dark cloud. Jill had also kind of given up on finding love again. Who would date a 48-year-old divorced women with a young adult son? And the men in her small town she wanted nothing to do with anyway.
Things did start to improve for Jack when he finished high school and went to college. It was only about 20 minutes' drive from home so he stayed at home while going to class in the day, and having football practice afterwards. He always loved football and Jill suspected he also used it to get rid of some of his anger issues. He met a bunch of new people during that time and it seemed he was finally letting go of the past. He even casually started dating a girl, Becky Anders. She was a cheerleader for their team, as real cutie too!
Jill nearly burst out in tears the night Jack brought her home the first time. It was not to "meet the parents" scenario, Jack just forgot something at home, but she didn't care, she could finally meet the girl who broke down his walls. And she could see why. Becky had long blonde hair, an athletic build with the perkiest B cup breasts she had ever seen. And her legs, it seemed they never ended, but they did eventually and was capped off by a tight little ass. A body any man, and some women, would surely lust after.
"Hi mom, this is Becky. We're just picking something up then we're going out again." Jack said nonchalantly.
"Becky Anders!!!" Jill exclaimed excitedly.
Jill wrapped her arms around Becky and gave her the biggest welcoming hug in the world, pressing her own C cup breasts into Becky's.
"I'm so happy to finally meet the girl I have heard so precious little about." she continued.
"Oh hi Mrs. Madison, I'm happy to meet you too." Becky said and giggled a little when she wrapped her arms around Jill as well.
The two women embraced for about 20 seconds when Jack eventually spoke up.
"Jeez mom, don't act like I've never had a girl around at the house. There's been plenty here before Becky!" he added jokingly.
The women released from their hug and Becky hit back with, "Sure you have buddy, I can always ask your mother if that's true. She's literally standing just here."
"Uhm no need for that, we're running late anyway."
Jill and Becky looked at each other and burst out laughing.
"I like you already!", Jill told Becky, "I can see he has met his match in you!"
"Yeah Mrs. Madison, I'm not going to be one of his many, maaaaaaany girlfriends he brings around the house as he claims."
"I would very much like that Becky, and please, call me Jill. Only my students call me Mrs. Madison!"
They both giggled again.
Jack quickly grabbed what he needed and pulled Becky out the door again.
"See you later mom, don't wait up for me, okay?" he yelled as he was going down the stairs towards his truck.
"Bye Jill, it was nice to meet you." Becky yelled over her shoulder.
"You too Becky, come round again soon!"
She looked on as the two darted towards his truck.
"Young love!" she thought to herself and for that brief moment missed being young again herself.
"You two must be careful tonight!" she yelled out at them, but by then the doors were closed and the truck started up. Jack revved the V8 motor a few times, and then they drove off.
Jill closed the front door and leaned back against it. Relief washed over her, her son was happy again and he found someone that could heal the scars of his heart.
*****
Jack and Becky had been dating for almost six months when Jack burst into the front door one evening, just before 11pm. He slammed the door behind him and the tears were streaming down his cheeks. Jill knew something was seriously wrong.
"What's wrong honey?" Jill asked.
"It's over, we're done!"
"What's over, who's done?" she asked again, not knowing what he meant.
"Becky! That's who! We're over! She fucking dumped me tonight!" he burst out crying.
Jill tried to get more information out of him, but it was useless. He was not in a state to communicate with her further.
In the following days she learned that Becky had dumped him because as she claimed, he was "distant" and had "commitment" issues, and lashed out whenever she talked about their future. The issue that Jill thought was a thing of the past had raised its ugly head again. Her fucking ex-husband somehow still had a way of messing up their lives!
The next two weeks were rough, on both of them. Jack went out every night with his friends and tried to drink the memories of Becky away. She was seriously worried that he was going to get into an accident and kill himself or another innocent person.
She tried to talk to him about it, but he wasn't interested in talking to his mother about relationship issues and would get in his truck and drive off again.
She let him be, hopefully he could get over it soon. Pain, as they say, is only temporary! He needed to deal with this his own way.
*****
Jill was woken up by Jack's truck as he parked in front of the house and revved the engine a few times. She heard him walk up the stairs of the porch and struggle to unlock the front door in his drunken state. She looked over at the clock on her bedside table. It was 3:15am. He eventually got the front door open and it slammed close behind him again. He almost knocked over the small entrance table next to the front door with nik naks she collected over the years. He stumbled down the hallway to his room, put the light on and the radio. By now she was wide awake and happy at least he made it home safe.
She lay in bed for about 15 minutes and was about to drift off into sleep again when her phone on the bedside table next to her vibrated. She ignored it at first. It vibrated again. Who was messaging her at this time of day? She picked up her phone to see what was going on.
Both messages were from her son. She opened them.
She immediately noticed they were not intended for her, but was meant for Becky.
In his drunkenness he did not realize he clicked on her name instead of Becky's in the recent chat section of his messaging app.
She continued to read the lengthy messages.
He pleaded with Becky to take him back, that he had learned from his mistakes and was ready to fully commit to her and their future. She felt bad for her son as she read the words.
