Author's Note: This story is completely fictional and did not happen. All names of characters are fictional and were made up. Please do not copy and plagiarize my work.
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New York City, New York
The car hummed as the wheels rolled down the street. The Lower Manhattan area remained vibrant and alive into the midnight hours, proving New York City's reputation to be true as the city that never sleeps. No matter the hour, the streets were always filled with cars in traffic and pedestrians strolling the sidewalks. A bright light outside belonging to a large, lit building cast a glow across Jennifer Lopez's face as she gazed out the right side passenger window. She had much to be happy about in the early months of 2025. Across from her sat a man who had taken on a special meaning in her life. After their second date, Henry succeeded in becoming Jennifer's new, younger boyfriend. Thirty-two years old was the right age that she now preferred a man now that she was in her mid-fifties. Over the past three months, Henry had proven he could help her forget the heartbreak of another divorce.
Under the gray pinstriped jacket was a silky white shirt. The first few buttons were undone to show hints of his newly toned, muscular chest. Under Jennifer's guidance, Henry was given a routine schedule at a gym to lose weight. His once bulging stomach had now dissolved into a flat build, revealing his defined abs. Monday and Tuesday were arms day. Never before in his life had he worked to train like this. If she wanted him to be in shape for the future of their relationship, Henry knew better than to refuse. He was living a dream that few men in his position could've obtained. For him to go from his life as an average working class man all the way to dating a legendary star was something to be proud of. It was an achievement that he didn't want to fumble from his hands. Whatever Jennifer wanted, Henry was quick to say yes. She claimed that she had 'big plans' for them if he could prove his worth in a matter of months.
With winter passing into the season of spring, Jennifer was ready to prove her word to Henry. He had impressed her by improving his appearance, so now she was ready to go public about their relationship with her local friends. With him being an outsider to her way of life, Henry had no knowledge of the inner circles around New York with people like her. Jennifer only gave him a hint when she pulled him from his job and gave him work designing more websites related to a company she had an ownership stake in. It was one way for him to get his foot in the door. What didn't pay well, she made up for by giving him spare cash when she had to travel outside of the state. Jennifer tested Henry by not giving him an NDA to sign. She knew the risk of a man like him going public about their relationship. Whether to friends in passing or telling stories on the internet, the man held cards for selling a story to gossip magazines.
Henry wasn't that kind of man. As the weeks passed into months, Jennifer monitored him online with a spyware app she had installed on his phone and laptop. She saw where he spent most of his online hours working. In his off time, he collected photos of her from various celebrity websites. It was one thing to have shared a bed with JLo, but another to be dating her. Henry thought he knew Jennifer from the research he had to do building her official website last year. She proved him wrong in the time they spent together. He became obsessed with building a collection of her photos. One of his personal projects was to create a photo album of all her professional photo shoots. He believed that would surprise her as a future birthday or Christmas gift. She carried herself with unbreakable pride in her status as a sex symbol and celebrity. He admired and respected this about her.
Through the months, Jennifer spent most of her time with Henry getting to know him. A 'date' for her usually required him coming to her house in the Hamptons, where she would cook for them when they spent time together. She had already tested his skills in the bedroom to learn what kind of man he was in the nature of love. He was fortunate to have impressed her with his skills. It was the most intense day of sex he had ever enjoyed. The experience was something Henry only shared with her and had no desire to tell another living soul. Jennifer made him feel things that his past girlfriends couldn't. He confessed to her that he didn't want to date another girl around his own age. Jennifer had awakened his taste for older women, and there was no way for him to go back. This only made her feel more confident about his potential as her new boyfriend. Time would tell if it would last, but right now Jennifer felt herself falling in love.
Tonight's agenda was to spread a rumor across town. This would be the first stepping stone to making their relationship public news. Jennifer had taken her time and went to great measures to keep Henry a secret from the media. After three months, she was almost ready to push him into the spotlight of fame. His life would change forever in the following days. Tonight was only the beginning, but Jennifer had other things planned. So far, he had learned about who she was as a woman. The night they met, he saw a hint of how fun she could be when she was comfortable around other people. He had yet to experience what it was like to walk by her side as JLo the superstar. Tonight served as a test to see how he could handle himself in public as her new boyfriend. A break was needed from the normal life in her Hamptons mansion. Jennifer wanted to show him that she could still party and have fun at fifty-five years old.
"This has been a long time. How close are we?"
As Henry spoke, Jennifer turned her gaze to him. She smiled as she reached for his hand, touching his warm palm.
"We're almost there, don't worry. Just a few more minutes."
Her long brunette hair was split down the middle. The gold hoops were visible from her earlobes in the darkness with a tiny bright spot from the passing lights. Below her face was a strong hint of cleavage with her breasts pushed up in a black bustier. Jennifer's abs and belly button were exposed, revealing some skin. Her pants matched the outfit with black leather. Before they departed, Jennifer told Henry she wanted to shake her ass tonight. It was easier to move around in leather pants compared to denim jeans. Below her strong legs were a pair of high heel pumps that revealed her big toes with a fresh layer of black nail polish. This was still a simplistic look for her with the hoops as her only piece of gold jewelry. Henry had recently had his hair trimmed, face clean shaved and wearing his grey suit. Jennifer commented that he was dressed like a gangster. He blushed before correcting her that he was missing the required rings and necklaces.
"Are you nervous?"
Henry shook his head at her question.
"No, I'm just excited. This reminds me of the night we met."
Jennifer smiled.
"Yeah, that was fun. But I'm not in the mood to do any singing tonight."
"You already told me that you're gonna be shaking that ass."
Giggling at him, she shook her head.
"I did say that, but I also asked if you would dance with me. You didn't give me a reply, so I'm asking you again. Are you gonna dance with me, Henry?"
"How could I refuse? How could I refuse anything from you, Jen?"
Grinning smugly, she teased him.
"You can't, cause I'm irresistible. I hope you're ready to stay up all night. If you play your cards right, we won't be taking the long trip back to the Hamptons."
He raised an eyebrow at her, curious to learn more.
"Oh yeah? Do tell me what you have planned."
Looking into his eyes, she raised her right hand index finger and gestured with a 'shhhh.'
"Don't worry about it right now. All you need to focus on is having a good time at the party. I don't like to spoil my surprises."
Lowering her finger, Jennifer spoke again.
"An old friend of mine is coming tonight. I've been hoping I could introduce you to her."
"You said her, so it's another woman."
She nodded.
"One of my girlfriends from a long time ago. We haven't seen each other since before the pandemic, so it's been a while."
"Wow, that's about five years now."
"Yeah. Before that, she stayed too busy dealing with her husband and family. She's recently single, divorced like me. We started talking again last month, and she's looking for a good time."
"Is she from New York like us?"
Jennifer shook her head.
"No. She doesn't live out here. She's traveling right now, and this is the one night I have with her. Trust me, you're gonna love her. You probably already know who she is."
As she laughed, Henry blushed. Jennifer wasn't giving him many hints to guess who the mystery woman was. If she was divorced and a mother, then there was a high chance that she was over the age of forty and in cougar territory. Most of Jennifer's friends were likely to be around the same age as her, leading Henry to wonder how many of them were single women. It was a funny thought. Maybe Jennifer had realized his taste for older women like her. Was she testing his loyalty to see if he would fall for the allure of another woman? So many questions ran through his mind, with much for him to consider.
"Just relax, Henry. Try to contain your excitement. This is gonna be a wild night, trust me."
After Jennifer spoke, the car slowed down. Her drive arrived at the side of an apartment complex. Henry got out of the car and walked around the other side to open the right side door. Jennifer smiled as he offered his hand, pulling her out of the car. She shut the door and then grasped Henry's hand.
"Come on, this way."
She spoke while nudging him to walk with her down the sidewalk. A simple black door was the entrance into what appeared to be an apartment building. Together, they walked down the lobby with her heels clicking and clacking loudly on the floor. Jennifer brought Henry to an elevator. After they entered, she pressed the button for the 7th floor. The elevator doors shut, and only the sound of his breathing could be heard for a few passing seconds.
