Celebrity Story Site
Stories & Art => Celebrity Stories => Actors & Actresses => Topic started by: Cadeauxxx on March 15, 2026, 02:23:59 AM
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Heart Fixing Business
Starring: Jennifer Love Hewitt
Themes: Seduction, Cougar, Older Woman/Younger Man, MILF, Big Tits
Disclaimer: This story is purely fictional. This is fiction, it did NOT happen. Fantasy is legal. Please do not copy this story to any site without my permission.
(https://i.postimg.cc/T359zX3h/H017.png)(https://i.postimg.cc/FHkZMQHk/018.png)(https://i.postimg.cc/dVZBbKVL/638609970-jennifer-2.png)(https://i.postimg.cc/zGHjs1GR/010.png)
Los Angeles, California
Voices echoed down the hallway and throughout the building. The morning silence had faded away as more people appeared on set. By the afternoon hours, every working crew was somewhere on the premise. The parking lot filled with rows of cars lined up. Some people called Uber as a way of getting to work. That was how Ray O'Connell managed on the weekdays. It was a desperate move after loaning his truck out to a friend who was using it across town. Today made the fourth consecutive week he started the Monday morning with a trip to the local gym. It was an extra cost in spare cash to the Uber driver, but it was worth it. After what he went through to finish off the year, Ray needed anything to get his mind off of someone. The very thought of her was enough to ruin an entire day. Some men used drinking to dull the pain of heartbreak, but not Ray. Alcohol never interested him. At twenty-two years of age, he still had much to learn about the world. Everyone loved to tell him that, to the point he always rolled his eyes at the phrase.
Stepping out of the Uber, the sunlight hit his clean shaved faced. Before departing the gym, he changed into his work uniform. A white collared shirt and black pants. Across his neck was a necklace with his ID badge. The building belonged to ABC, and Ray was part of the many crews working on set for the show 9-1-1. The job had been offered to him after he lost his previous job working on an equipment crew for another ABC show. A year had passed since the flaming rampage that burned through Los Angeles. Ray was not a native to California. He only worked there after dropping out of Berkeley College two years ago. He enjoyed the west coast weather. It was much better than the frigid cold back home in Boston. That led him to stay in Hollywood, despite the lack of job opportunities. His line of work was easily summarized with the word 'helper.' From cleaning rooms to hauling equipment, all of it was worth the paycheck. Ryan found it difficult to pay rent for his studio apartment in L.A. before taking on this job. The pay was all that mattered.
Hollywood had seen better days. That was a common saying among many people in town. Ray didn't think much of the job he had. This beat working at a grocery store or any other kind of minimum wage job. Much had been spoken of how the film industry was in a downward spiral. Ray didn't think much of it. Hollywood had seemingly been around forever, and he believed the business could pick back up. Some had hope that things would pick back up, but other people knew better. The fires had caused significant damage that was still felt a year later. It was in that tragedy that Ray decided to stay in California. He spent two months working with volunteers on cleaning and the relief effort. The experience remained with him as a great life lesson in helping others. This job he currently held wouldn't have been possible without the charity work he did into March cleaning the damage. To be there alongside others in a time of need had made him believe change could come from others. Ray had spent so much time building his body to be stronger. Through his time working, he also met someone who changed his life for the better. The same person he was trying his best not to think about.
Lexi was his girlfriend throughout most of 2025. The daughter of a Hollywood executive, she lived a busy life through social media. Ray took to her beauty with long slender legs and beautiful blue eyes. Her hair was a shade of blonde, and she enjoyed wearing dark clothes, regardless of the L.A. heat. Ray became obsessed with her almost instantly. Lexi helped get him the job at the set of 9-1-1. She had her own gigs from social media with modeling designer outfits and endorsements for influencing brands. Ray believed that he was a man in love by September and tried to push to make their relationship more serious. That was when he became curious to finally go on social media and see what his girlfriend was up to. What he saw greatly disappointed him. Lexi had built an entirely different persona as a model online. She sold a lifestyle of high class luxury and wealth. Before his curiosity got the better of him, Ray used to wonder why she would leave for a few weeks and come back. She always told him that it was to 'get away from town.' He didn't know it was to take trips to lavish places and enjoy the good things life had to offer. None of which he could afford with his normal background.
The heartbreak came at the end of December when they finally broke up. Lexi made it clear to Ray that she had greater plans for a future that didn't involve him. She had offers from other men who could manage her influencer lifestyle better and become more successful. Ray was left with the job she helped him obtain, working on the set of 9-1-1. After the breakup, he thought of quitting. It would be one way of forgetting all about her. But then Ray remembered how much he enjoyed his paycheck every Friday. This job was good enough until a better opportunity came along. In order to get Lexi off his mind, he began working out. His only real hobby was at the gym. He didn't spend much time online. Maybe that was why Lexi never offered to help him become an influencer. Ray met many men at the local gyms who were into the fitness genre of social media. Some hired entire crews of cameramen to follow them around and sell a persona to their followers. Ray was never interested in posting on social media. The only times he surfed the internet were to cure his boredom with searching for porn online.
MILF and big tits were the two tags he searched anytime he browsed. The complete opposite of his former girlfriend. It was one attempt to forget about her. On the other hand, Ray had a certain preference when it came to the fine women of the world. He didn't know the names of the porn stars he watched but recognized them in various videos. During his time spent helping in Palisades, Ray made friends with some other guys. Some of them had interests in skateboarding and other activities. It never crossed his mind to do anything like that. His hobbies remained at the gym and looking at kinky videos online. Near the end of January, he became worried that Lexi would linger on his mind until Valentine's Day. Ray knew that he would be feeling lonely by the time February began and that holiday was looming around the corner. He tried not to think about it today as he walked past the security guard and entered the building. Down a few narrow hallways led to a large room with various equipment. Ray's boss stood near the doorway with his hands on his hips. The older man wore the same uniform without the name tag.
"I see you didn't take your sweet time getting here today. That's an improvement for you."
Michael had a reputation for being a strict boss. He didn't beat around the bush when he told off the workers for their slacking. The old man was bald, lacking wrinkles that could make someone guess his actual age. Ray always assumed he had to be in his fifties due to his voice. There was no need to argue with him, since Ray knew he had been coming in to work late the past week. Ignoring the comment, Ray nodded.
"What's on the menu today?"
"Vinny called in sick today, so we need someone to move in the camera equipment to the main set. Since you're more reliable than his lazy ass, that gets to be your job today."
Ray blinked to prevent himself from rolling his eyes.
"Don't just stand around here. Get your ass over to Set A and help the camera crew."
"Whatever you say."
Three words to prevent himself from making a snarky reply back. Ray turned and went on his way down the stretching hallways. Up the stairs to the first floor led to what was referred to as Set A. It was a large room built to replicate an emergency services room in a tall building. The windows were off to the side and covered up. In post-editing, they could be changed to black. Today's filming must have been for scenes set during the night. Desks were made with metal pieces, matching the sleek grey and black interior of the room. All of them had large flat screen monitors to be used by the operators. On a normal day, the entire set would be active with over a dozen people. Many of them were actors known as 'extras' to be shuffling in the background. The main stars all had their personal rooms downstairs. Jennifer Love Hewitt led many of the scenes. Her portrayal of Maddie Buckley-Han made her one of the main cast. Ray had met her and Ryan Guzman numerous times. They were always friendly to the many crew members working on the set. When Jennifer entered the room, she lit up the entire environment.
"9-1-1, what's your emergency?"
Her famous line from the show, combined with her big smile, always lifted the spirits of everyone in the room. Ray was fond of Jennifer the few times he had been around her. She remembered every name of the cast and crew members. When Christmas came, she bought gifts. Even if it was just a bag of cookies and candy, the thought was what counted. Anytime she saw Ray, she asked how he was doing. He didn't know much about her beyond the fact she was a star. Her aged face told him that she was a woman in her forties. Her uniform to play Maddie was typically black pants, a maroon red shirt, and a black jacket. She was always wearing the 9-1-1 badge on the right side. Sometimes the jacket was undone, revealing her busty cleavage. Someone once joked about her being famous for 'the cleavage' on another show in a different era. Ray never thought to search her name online. The thought of watching the actual show he worked on seemed weird in his opinion. Her long brunette hair had been dyed with locks of amber shading, giving her locks a fiery red flare. The look went well with her pale skin. For a woman in her mid-forties, she looked amazing and fit the type he searched for online. Jennifer Love Hewitt was what Ray considered the definition of a MILF.
Ray avoided thinking about Jennifer that way. She was a married woman, closer to turning fifty than he was to reaching his thirties. A woman like that was entirely out of his league. It was still nice to be greeted by her kind smile anytime he was working on Set A. She always asked about how he was doing. Ray had not seen Jennifer in over a month. He could imagine that her life was going well with her family back home. He thought about her as he entered the room. Two cameramen were already standing near a station that needed to be moved. Ray walked over and immediately offered a helping hand to them. After a few words, they directed him to move one camera to the left side of the room. As soon as he was done, she entered the room. Heels clicking and clacking as she strutted slowly through the doorway. Jennifer Love Hewitt's head was raised high. The fiery amber locks of her hair were glowing as her cleavage jiggled with each step. A sparkle of a tiny diamond on the left side of her nose had become a signature piece of her jewelry. Her brown eyes leered, making contact with Ray as she smiled at him.
"Hey there, Ray. I haven't seen you around in some time. How have you been?"
"Hey Jennifer, I've missed you. Those cookies you gave out for Christmas were great."
He avoided her question, thinking back to the Christmas party. She flashed her teeth in another smile.
"Oh, thank you. I stayed up all night baking them. No one has mentioned the cookies since after New Year's. They must've been really good if you're still thinking about them."
Ray blushed, unable to hide his smile.
"Well, the last time I saw you was around Christmas."
"I know. Scott told me you've been showing up late most days."
"I have. I've been going to the gym every morning. That has been my main focus to start the new year."
Raising an eyebrow, Jennifer nodded at him.
"I can see that. I was going to say, you look like you've been hitting the weights lately."
He continued to smile as her eyes scanned his arms and biceps. Ray was taller than her with a more bulky frame that he chiseled out through time spent at the gym. Jennifer's eyes returned to his before speaking again.
"I heard about Lexi. I'm sorry you had your heart broken."
The mention of his ex-girlfriend's name was unexpected. Ray blinked, feeling a bit uneasy as Jennifer offered him a comforting, friendly smile.
"How did you know about that?"
"I hear about everything that goes on around here. Most people who work here have been around a long time. That makes us almost like family, so we know what goes on in our house."
From what she said, Ray could piece it together in his mind. A rumor must have spread. Lexi had been on the set a few times to visit him during the summer.
"What happened to your truck? I haven't seen it in a while."
Her question surprised him even more so than acknowledging his breakup. Ray never would've guessed Jennifer to notice his truck was missing in the parking lot.
"I let a friend borrow it."
"So how have you been getting to work?"
She stepped away, moving towards her desk that she had sat at so many times before. Ray followed at her left side. A rolling desk chair was prepared for her. The back of it had a black leather cushion.
"I've been calling an Uber every morning. I go to the gym, and then I come to work."
"You could save a little bit of money asking a friend for a ride."
"I suppose you're right, but I like to go to the gym alone. It has been helping get my mind off Lexi."
Jennifer's eyes returned to his face, and she offered that same reassuring smile. The look alone was enough to melt him. Her kindness made Ray want to jump to do something for her. As she sat in the chair, he had a great view of her full cleavage in the dark red top. He avoided the temptation of glancing down.
"Jennifer, can I get you anything before you have to get started?"
Her smile widened, revealing all her teeth.
"I left my coffee in the break room. Can you bring it to me?"
"I sure can."
Before Ray walked off, she raised her right hand. The sleeve of her jacket slipped, revealing some of her tattoos that weren't hidden by makeup.
"It's in a black tumbler with a heart sticker on it. You can't miss it!"
Ray wandered off, leaving the set to take a short journey to the break room. Inside was a wooden counter with a microwave in the corner. He spotted the black tumbler cup. The heart sticker on it was red with her initials written in black. After fetching it, he wandered back to the set to see Jennifer sitting there, grinning wide as he placed it on her desk.
"Thank you."
That lovely smile and her voice were enough to make his day. Ray nodded at her and went to walk away. He noticed the director shuffling through the door with a folder in his hands. Filming would commence soon with the room fully prepared. His duty here was done. It was time to make a trip back to his supervisor and see where the old man wanted him next. However the day progressed, Ray was grateful for the few minutes of time he spent with Jennifer. It was all he needed to feel better about himself. Maybe it was a good thing he decided to show up on time today.
******************
4 HOURS LATER
Studio lunch hour was closer to 12 PM, rather than the usual 10:30 AM time at most jobs. Every crew had their break around the same time. After departing from the set, Ray ventured off to find Michael. He spent the next few hours on shift hauling equipment outside to another room with a coworker. Scott was his companion for this job. Another young man with short black hair and a muscular build. Ray thought of asking him if he told Jennifer about his breakup. On second thought, he decided against discussing it. He didn't want to think about Lexi. Most days at work, she would cloud his mind with precious memories and bring back the pain of heartache. Outside, a camera crew gathered into two vehicles. Ray wondered where they were heading. Somebody must have scheduled scenes to be shot late into the afternoon. Ray wondered about it while standing outside the building. His eyes scanned across the parking lot to see if any vehicles were missing. The sun beamed down, blinding him with bright spots cast across the many windshields.
His right hand fingers gripped a can of Pepsi. He glanced away from the cars and raised the can to the edge of his lips for a quick sip. A few vehicles were missing from the parking lot, but not enough to clear space. Ray didn't know what cars everyone drove. For a moment, he missed his truck. It was a 2009 Chevy Silverado in a metallic blue finish. The paint had faded over the years prior to when he purchased it. It wasn't a luxury vehicle, but it was the kind of ride to get a job done. The hubcaps had also been swapped out by the previous owner. The only piece of customization he did was changing out the seats for a new set. As he took another sip from the can, the wind blew. The temperature increased slightly into the high 50s to make this yet another chilly January day in Los Angeles. It was still better than the snowstorms he knew from back home on the east coast. As Ray stood there, the sound of walking could be slowly heard. Click. Clack. Click. Clack. Turning to gaze in his right direction, Ray saw Jennifer approaching him. She was wearing a denim blue jacket with a navy blue blouse underneath and jeans to match.
"There you are. I've been looking for you."
A brown leather purse clung to her right shoulder as her hand clutched the tumbler. Ray smiled at her. The blouse had a collar and white buttons. The first three were undone, revealing a hint of her heavy cleavage within.
"Are you done for the day?"
"Yeah, we wrapped up filming half an hour ago."
The wind blew, slightly pushing her long amber locks of hair behind her shoulder. Between Jennifer's left index and middle finger was a blue sticky note. He noticed the tattoo on her middle finger, directly above the nail. She passed him the note, watching him take it into his free hand.
"What's this?"
"That's the address to my new vacation home. I'm having some work done back at my house, so I'll be staying there until Thursday."
Raising his eyebrows, Ray tried to process her words. Was she really inviting him over? He had to know, but before he could ask, Jennifer continued.
"Since you said you call an Uber to get around lately, just give the driver that note. I want you to spend the day with me tomorrow."
"Really?"
Nodding her head, Jennifer smiled at him.
"Yes, really."
"But why?"
"You've had a rough start to the year. I know what's going through your head right now since you just went through a breakup. So I'd like for us to hang out. Tomorrow it can be just you and me all day."
"But what about work? I have to be here tomorrow, or else I'll get written up."
Jennifer stopped and grinned at him.
"You don't have to worry about that. Since we're not doing filming tomorrow, none of us are showing up. All I have to do is make a few phone calls, and you'll be fine, okay?"
Her smile remained, showing the top row of her teeth. That smile was enough to soothe his mind and make him drop all of his concerns.
"You said it would be just us there?"
She nodded.
"Yeah. I haven't seen you since Christmas, and I can see that you've been sad lately, so let's spend a day together. We can talk about stuff, and I'm sure that will help you forget about her."
Listening to her, Ray nodded. He looked over the note to see Jennifer's handwriting in black ink. Underneath the address was a phone number.
"I see you left your number. Do you want me to text or call before I arrive?"
"Text me."
The smile was still on her face as she began to walk off. Into the parking lot, Jennifer marched towards her car, a white Bentley Bentayga SUV. A fine luxury vehicle for a whole family, fitting for Jennifer's level of stardom. She turned her head, flashing a grin at Ray.
"I'd offer you a ride home, but I need to pick up some groceries before taking the trip. It's a long drive out of town. Make sure you text me when you're close."
"Don't worry, I will."
"See you tomorrow, Ray. It's going to be cold tomorrow, so remember to bundle up."
"What time should I be there?"
"Leave early. Try to beat the morning traffic, so I'd say sometime before four, if you're up that early."
He watched her open the driver's door. Another person stepped forward, brushing past them on their way to another vehicle. Waking up at 4 AM was asking for too much. Why would this be such a long drive? The only way for Ray to find out was to put the address into a Google search on his phone. He figured that was best to do once he got home. At least now he could call off work and have a day to himself. This would also make the first day he didn't check in at the gym first. A break was needed after all the work he did on the treadmill and lifting weights. Something deep inside him told Ray that tomorrow was going to be a good day. At most, he could learn more about Jennifer and what kind of person she was off the set. She had already succeeded at making his day better, but now he was thinking ahead. What awaited them back at her vacation home? Only time would tell. One way or another, he was going to find out by arriving on time.
******************
1 DAY LATER
San Diego, California
The morning temperatures before sunrise proved to bring back memories of life back home in Boston. Frigid, icy, and frozen. A black letterman jacket kept his arms and chest warm. Blue jeans and black boots were the other choice of clothing on this freezing morning. Ray learned why Jennifer insisted he leave early. The address she gave him was for a property in San Diego. He was more curious about how she owned the place, rather than the long drive that awaited. It was important to get a head start and beat the morning traffic down the interstates leading through Los Angeles. After a morning shower following seven hours of rest, Ray was out the door by 5 AM. An Uber picked him up. The driver warned that it would be a long and cold ride. Ray insisted he was fine with that. Riding down the highway, he would see the rising sun across the hills from the back of the black car. The driver was a young man, similar to Ray. He kept quiet, leaving his passenger only to hear the sounds of a motor and a vehicle moving down long stretches of paved roads.
Within an hour, they met the traffic. Ray kept his phone in his hands, fighting the urge to begin looking up photos online. He knew better than to search anything related to porn with this meeting coming up. It was best to keep a sharp mind and not be clouded by temptations before meeting Jennifer. Various vehicles passed by them through the windows on other lanes. Ray didn't bother studying them. When you lived in Los Angeles, you became accustomed to seeing luxury vehicles that only high salaries could afford. The heater powered on in the car, making the backseats more comfortable as they became warm in the passing hours. The driver alerted Ray after a few turns. Once they reached the neighborhood areas, he told Ray that they would be arriving within the next fifteen minutes. That was the cue for him to press his thumbs across the flat screen of his smartphone and type a quick text message to Jennifer. 'Almost there, should be pulling up in a few minutes,' he sent. She read the text, replying two minutes later, 'can't hardly wait to see you' read her reply with a smiley face emoji.
When Ray stepped out of the car, he was greeted with sunlight and a clear blue sky. His breath was visible in a puff of smoke from his nose and mouth. The front yard was clean with dead grass. Jennifer's SUV was parked in the gravel-lined driveway. He stood near a mailbox, looking out at the house itself. On first view, it appeared to be a standard one-story middle class home built with bricks. Ray wondered how old the walls were. Two windows were visible between the red front door. A big mat with the word 'welcome' was on it. Wooden interiors were painted white around the house to give it a fancy look. From the outside view, the home looked more cozy compared to the luxurious McMansions and bigger houses he had seen in L.A. Ray had the impression Jennifer preferred to live modestly instead of flashing her wealth with luxury. That separated her from other Hollywood actresses who had huge houses in Beverly Hills and Calabasas behind gated communities. Ray thought about that as he approached the front door and then knocked with his left hand. He took a deep breath before the door quickly opened.
"Hey! You made it!"
Jennifer greeted him with a full smile as she stood in the doorway. Her auburn-colored brunette hair was split down the middle with swoops. Makeup was minimal, with only some shadows around her eyes and shiny pink lipstick. She wore a black blouse and matching mini skirt that revealed her heavy cleavage and slender legs. Below, he saw her feet hidden by a pair of matching black high heel pumps.
"You're all dressed up. Waiting for it to warm up to go out?"
She shook her head.
"No, I wanted to look good for you. Come in, I've got it nice and warm for us."
Turning her head, she revealed her thick ass tucked in the black skirt. Ray could see the outline along with the rest of her curves. He walked through the front door and closed it behind him. Sconces were mounted on the walls, embedded in the wooden panels to create dim lights. From the front door led to a narrow space with a coat hanger to the left. Upon noticing it, Ray wanted to remove his jacket.
"Do you mind if I take off my jacket right here?"
"No, go right on ahead. Take your shoes off and get comfortable too."
Taking her advice, Ray unzipped his jacket and took it off. It was funny she was telling him to take off his shoes while stepping around in high heels. They boomed loudly across the wooden floor below. The sound was muted when Jennifer entered the living room. By then, Ray had pulled off his shoes and lined them up near the door. He kept the socks on so his toes would remain warm. The curtains were pulled back to allow sunlight to illuminate the large living room space. A few framed photos hung on the wall. Paintings and black and white pictures of Jennifer and her husband. The floor tiles were hidden with a large red rug covering them. In the center of the living room was a rectangular-shaped wooden table painted black. The surface was satin and clean with only a few bottles of water and a magazine sitting there. A black leather couch sat across the table. On the wall was a large flat screen television that was currently turned off.
"Wow, this place is nice. I thought you would live in a big mansion or some place fancy like that."
She smiled, revealing her full teeth. Jennifer slowly nodded. Ray's eyes scanned across the room. He noticed a doorway to the far north side leading into another area. To the south was another open doorway with the lights out. Since there was no staircase, he figured one doorway must have led to the bedrooms and another into the dining room and a kitchen area. Jennifer spoke in a low voice.
"I have a bigger house for my family back in L.A. This is my vacation home. I bought it from a friend who moved out of state."
"Where did they go?"
"Nevada."
Ray chuckled.
"I'm guessing Las Vegas then."
Jennifer shook her head.
"No, but you were close."
Clapping her hands together, she smiled again. Ray watched her palms rub together before Jennifer spoke again.
"Have you had anything to eat today?"
"I ate some strawberry Pop Tarts when I first got up."
"That doesn't sound like much food, and I imagine it was hours ago. So you're probably hungry right now."
Curving her lips into a full smile, Jennifer raised her eyebrows as she gazed up into his eyes.
"Let's start the day off with a good meal. Come on, I can cook for us. If you want, you can help me. Let's have lunch and talk about things."
******************
2 HOURS LATER
The temperature rose, melting the frozen layers of ice around objects outside. A different kind of heat was brewing inside. From the kitchen, Jennifer raised the temperature on the stove. She slipped off her heels and curled her hair into a high ponytail. Ray watched her slip on a white apron before she went to work at the stove. He felt the need to offer a helping hand. That was when she directed him to the cabinets to get down plates and silverware. Her next instructions were for him to dig into another cabinet near the fridge and pick a bottle of wine. Ray was given the choice. He had never opened a bottle before, leading to slight embarrassment as he told Jennifer. She just laughed and told him to pick whatever he would like to try. On the stove, she made a pot of pasta. In the oven, a fresh loaf of bread was baked. Within an hour, the strong scent of the fresh food made his stomach grumble. Jennifer laughed when he mentioned this. She led him to the dining room, where a large table stood in the center of the room with four chairs, two on each side.
Back in the kitchen, he helped her bring in the food and place it on the table. She made pasta and cut a fresh loaf of bread as a side dish. Once they were ready to eat, she took off the apron and joined him in the dining room. Jennifer took the honor of uncorking the wine bottle. Two glasses were prepared, and she poured Ray's first. After sitting down, they began to talk about life between eating. Jennifer told Ray that she was eager to learn more about him. All she knew was that he was a young man from Boston who worked on the crew. Ray had the chance to ask her about her career and stardom. He chose not to dive into those subjects. Jennifer explained that in the past few months, she had been going on podcasts for interviews. She hinted at a trip to New York City. That made Ray smile, shifting the discussion to how he always wanted to visit there. 'I don't think you'd want to go this time of the year. It's too cold,' Jennifer commented, making him blush and laugh. After two glasses of wine, he felt more confident to begin opening up about his personal life. Jennifer waited until they were close to finishing lunch before she brought up the question of his ex-girlfriend.
"So how old are you, Ray? I'm just curious since Lexi broke up with you."
"I'm twenty-two, and what about you, Jennifer? How old are you?"
Flashing her teeth in a smile, she played with the wine goblet between her right hand fingers. Jennifer was seated across from Ray, where she could look into his eyes.
"I'm forty-six."
"Damn!"
A smug grin ran across her lips, almost as if Jennifer had expected his surprised reaction. She raised the glass and sipped the remainder of her wine. The smile was still on her face when she sat the glass back down.
"Since I'm in my forties, I can tell you a little something about having your heart broken. I'm guessing Lexi was the first serious girlfriend you've had in your life."
"You can say that. She was my first real girlfriend, you know? I went out with a few girls in college, but it was nothing big like this. I thought our relationship could go somewhere."
Jennifer's right hand slid across the table, brushing her fingers against his. Ray's eyes focused on her face as she replied.
"Honey, it just wasn't meant to be."
"Maybe you're right."
The warm touch of her fingers distracted him. His eyes fell, shifting to her arm where he saw the tattoos across her wrist. An eye was under her hand. Her middle and ring fingers had tattoos above the knuckles. Looking back at her face, the piercing on the left side of her nose sparkled in the light.
"I know I'm right. I've been in your shoes before. It sucks to go into a new year all sad and blue from a breakup. That's why I invited you to spend the day with me."
Leaning forward, Jennifer gave him a great view of her cleavage in the black dress. It was as if she knew his eyes would wander below her face and take in the wonderful view. She withdrew her hand, and then Ray took a deep breath before replying.
"Do you want to talk about Lexi?"
Jennifer shook her head.
"No. I want to talk about you and me. Let's talk about us."
"What do you mean?"
"I'll put it this way. I like you. You're a nice young man who works his ass off. So I'm going to play the role of heart fixer for you. Let me fix that hole in your heart, Ray."
Her voice shifted into a low, more seductive tone. Swallowing his breath, Ray felt nervous. He knew what Jennifer was doing to him. The way her big brown eyes glared back at him, she was skilled at the art of seduction. That look on her face told a tale. It was a seductive expression he knew all too well from the many porn videos he watched with older women and younger guys like him. His ideal fantasy situation was unfolding before his own eyes. Here he was, taking an open invitation into a vacation home owned by a married woman. The rings on her fingers were meaningless. Jennifer wanted him, and that was all that mattered. How could he refuse her charm? Ray knew it wasn't worth trying to play stupid. He looked her in the eyes and spoke.
"How do you plan on doing that?"
Rising up from her chair, Jennifer smirked and extended her left arm. Ray noticed the black ink of butterflies drawn across her wrist.
"Join me in the living room."
While Ray sat there, his eyes followed her. Jennifer strutted her hips as she stepped to the doorway. Her high heels were lined up at the edge leading into the living room. He watched her bend over, exposing her thick ass outward to his keen eyes. She slipped the left heel back on first, then the right one. He was still sitting there as Jennifer stomped her way into the living room with loud clicking and clacking. Ray closed his eyes and let out a deep breath. Once again he thought about all the times he enjoyed watching MILF porn stars on a screen. Now he had a MILF who couldn't wait to get her hands on him. He got up, leaving behind the dirty plates of food on the table and empty glasses. Back in the living room, Jennifer stood near the couch with her hand on her hips.
"Ray..."
"Jennifer..."
Stepping closer to him, she raised her right hand index finger to his lips, gesturing for him to go quiet.
"This is heart fixing business, and I'm the one who does all the repairs."
With that said, she pushed her lips against his. Ray reacted by kissing her softly, then again with more force. His arms wrapped around her as Jennifer's tongue slithered into his mouth. She kissed him more passionately, causing his cock to begin growing within his pants. His hands caressed her curves, feeling the tight fabric of her dress. The food and wine were tasted within Jennifer's mouth, but Ray didn't mind. It felt so good to be kissing a woman again and washing away all the memories of his former girlfriend. When their lips pulled apart, Jennifer turned her back to him.
"I picked this dress just for you. There's an old saying in showbiz: the prettiest dresses are worn to be taken off. Go ahead and take it off for me."
A shiny silver zipper was visible up the middle of the dress. Ray grabbed it and carefully pushed down, listening to the noise it made. Her pale skin became visible as the dress loosened. With the zipper down, he pushed at the sides of the dress. It hit the floor, revealing her fine rump with a black thong tucked between the crack. No bra was necessary to push up her busty, natural tits. They jiggled around as she turned to face him. Jennifer grinned as she pressed her hands against her own tits, squeezing them hard.
"Your girlfriend didn't have tits like mine."
Sliding her hands underneath them, she pressed her boobs together and offered them to Ray.
"Go ahead and touch them. You know you want to."
Ray's hands pressed down to feel her nipples rubbing against his palms. Jennifer withdrew her hands to allow him full access to her tits. He couldn't believe he was squeezing a pair of beautiful MILF breasts. They looked even better than all the porn stars he watched on his phone. Jennifer's breasts had to be a triple-DDD cup, so he wanted to believe. His thumbs rolled over her nipples, causing her to moan. As he played with her tits, Jennifer used both hands to slide her thong down. It caught Ray's attention, prompting him to glance down and see her wet pussy. No hair was visible above the pretty pink folds. Their eyes met again, and then Jennifer took his hand.
"Come on. I want you to sit down. I'll help you get good and comfortable. Just relax, and I'll make you feel so good."
She only held his hand for a few steps. She let go, turning to her side to glance down at the front of his jeans to see the visible bulge poking forward. The sight made her smile. Her heels were muted across the rugs on the floor. The room was warm enough to strip without the concern of a cool breeze making them uncomfortable. Ray sat down in the middle of the couch. Jennifer stepped closer to him and then fell down to her knees.
"I'll take these off."
Grabbing the front of his pants, Jessica undid the button. Ray took a deep breath while she gazed into his eyes. Ray snatched the ends of his T-shirt and pulled it over his head. While he did this, Jennifer grabbed the elastic band of his underwear and tugged it down. Ray felt his cock jump free as he pulled the shirt off and tossed it to the floor. Below, he saw the sight of Jennifer grinning at him as her right hand gripped his cock. Her warm, delicate fingers wrapped around the pole.
"Mmmmmmm, I can feel how hard you are."
Up and down, Jennifer slowly pushed her fingers. Down and up, she moved slowly while looking into his eyes. Her left hand shoved his jeans and underwear down to his ankles.
"Let's get your pants and underwear off. The last thing I want is for you to trip over yourself later."
Jennifer released his cock from her gripping fingers to use both hands to get his underwear and pants out from his ankles. Now they were both naked, with his clothes sitting on the floor against the couch. She raised both hands and grabbed his cock, twisting all ten fingers around it. Her hair was still in a ponytail, with the sunlight illuminating a few locks in a deeper red shade. On her left shoulder was a visible black outline of a heart etched into her skin. It was one of many small pieces of art on her body that Ray admired. She moved her left hand, resting it on his right thigh. Jennifer flicked her tongue across the head of his shaft and resumed pumping with her right hand.
"Just sit and watch me. I'm going to make you forget all about your ex. When I'm done sucking your dick, you will never want Lexi again."
Parting her lips, Jennifer pushed her fingers down to the base and lowered her head. His cock slipped into her mouth, and she began to bob her lips up and down. Ray exhaled a deep breath and let it out.
"Ohhhhh, man."
It was easier not to think about Lexi, even though Jennifer mentioned her name. The difficult part was all the naughty feelings that were now manifesting for Jennifer. She took her time pushing his cock halfway into her mouth and then pulling back. 'Mmmmmm,' a muffled moan escaped her lips. Jennifer pulled back and released his cock with a pop sound. Her fingers tightened around the pole, then she resumed jerking it with a smile across her face.
"Hold on. I'm just getting warmed up here."
Gazing down at his cock, Jennifer licked her lips and ejected a small wad of spit onto the head. She used her own saliva as lube to smear across his long, throbbing rod. Her hand glided easily across his slick skin. Biting her lower lip, Jennifer purred before enveloping her lips around the tip again. She went back down, this time releasing her fingers from the base. Jennifer pressed both hands against his legs as she took his cock further down her throat this time. She had already proven to be more skilled at sucking than his ex, but Ray had higher expectations for Jennifer. She pushed his cock all the way down, deepthroating it without any gag sounds. He grunted, clenching his teeth together. That sound alerted Jennifer to gaze up at his eyes. She slowly pulled back, releasing his cock from her mouth, this time with a louder pop. The noise echoed through the room as his wet shaft flopped against his stomach.
"Give me a few seconds. I'm not done with you just yet. I want to suck this cock some more."
Jennifer raised her arms and loosened the ponytail holding her hair. The band hit the floor, and then she ran her fingers through her amber locks of hair to straighten the split down the middle. Her right hand moved back to his cock, lifting it up. With her hair free, Jennifer kissed the tip before pushing it back into her mouth. Ray appreciated this gesture. Her face looked so much sexier with her hair down. Jennifer pushed her lips far enough to reach her index finger, then pulled back up. She created a rhythm, bobbing her head up and down as she sucked his cock by the inch. A few strands of hair moved around her left eye. Ray reached out, brushing the hair back behind her ear. That made Jennifer stop sucking. His cock was still between her lips as she gazed up at his face and slowly pulled it out with another pop.
"Thank you for that."
She winked before kissing the tip of his shaft again. Jennifer's tongue slid out, licking a circle around the tip as she gripped his shaft. Her hands pumped up and down once again. Nice and slow, she took her time for them to both enjoy this sensual pleasure. This was as much for her enjoyment as it was for him. Ray let out a low moan before she pushed his cock back into her mouth yet again. He was at a loss for words from the way Jennifer sucked his dick. There was something personal in the way she handled this. A real sense of feeling that he had not felt since his breakup. Jennifer closed her eyes and pushed every last inch of his cock into her mouth. Her hands moved, pressing onto his legs again as she maintained herself.
"God!"
The only reply back to his loud exclamation was low sucking noises from Jennifer's mouth. She moaned a muffled sound, causing him to feel vibrations around his cock. Her eyes opened, gazing up at him again as she moved her right hand to the base of his shaft. Jennifer stroked from the bottom, raising her hand in sync with her lips. What she didn't slip past her lips, she jerked with her hand. 'Mmm, mmmmmm,' her soft moans were heard between slobbering noises that grew louder with each suck. Ray felt that he could withstand more of her sucking without getting close to the edge. Another light strand of her hair moved to the left side of her face, but Jennifer swiped it away on her own. She released the grip of her fingers and slammed his cock down her throat again.
"Fuck!!"
Ray's voice was louder this time around. Jennifer withdrew her lips and released his cock from her mouth with a deep sigh. A few strings of saliva dangled from his rod, soaked in a shiny coat of spit. The strands broke off and landed on the floor. She allowed his wet shaft to lie against his stomach while lowering her hands. Ray didn't realize what she was doing at first. Not until she flexed her elbows and revealed her hands holding up her huge tits. Jennifer pushed them up and then used her left forearm to wrap around them. Ray smiled as he realized what she was about to do. Her other hand gripped his cock and shoved it between her tits.
"Oh my god. Thank you."
Jennifer blushed as she adjusted her arms and squeezed her breasts around his shaft.
"Why are you thanking me?"
He pointed at the tip of his cock that was briefly visible at the top of her boobs. Jennifer bit her lower lip, flashing the top row of her teeth in a goofy grin, and purred as he replied.
"That right there is why I said it. Thanks for wrapping those big titties around my dick."
"Mmmmmmm, you like fucking tits, Ray?"
Answering her question with a quiet nod, Ray listened to Jennifer chuckle.
"I love the feeling of a hard cock between my tits. I can feel you throbbing for me, and it feels so wonderful. Just sit back and relax, Ray. I'm going to make you feel so good with my tits."
After speaking, she began to slowly pump her breasts up and down. Ray let out a deep moan as his slick shaft glided so easily between her heavy, soft tits. Jennifer glanced down, watching the head poke up. She spit on it. The noise echoed throughout the large room.
"God, that feels amazing."
Ignoring his praise, Jennifer rocked her tits up and down. After a few pumps, she found a rhythm and went to work moving at a moderate pace. It was faster than how she sucked him. Ray took another deep breath and just sat there and watched as his shaft disappeared between the folds and the head poked back up with each complete thrust. Jennifer's eyes shifted back to his face, and she grinned while working her tits. She bit her lower lip and purred in a soft, low voice.
"Ohhhhhhh, yeah. It feels amazing, yes. Mmmmmmmmmmm, yeah. I can feel every last inch of your cock between my tits. It feels so good."
Ray found it difficult to maintain eye contact with her as she uttered every last dirty word. He focused on watching his cock vanish between her tits, with only the head poking up after every thrust. Jennifer was watching too. She continued to pump her breasts up and down, tittyfucking him with ease. It became clear to Ray that she had done this many times before. He could only imagine the amount of practice she had over the years with men before him. For a moment, he wondered if she gave her husband this pleasure. Maybe, or maybe not. It was best not to tease her with that question.
"Keep going, Jennifer."
Over and over, she pumped her huge tits around his cock. Raising her head, Jennifer bit her lower lip and purred soft moans. Every time she slammed her breasts down, it created a slapping sound against his thighs. Smack. Smack. Smack. The sounds were heard loudly over the low breathing sounds from their voices. When she began to pump faster, it became clear to Ray that Jennifer had no plans of stopping. She was fucking his cock to a pulp with her wonderful tits.
"Oh, god!"
As he moaned, a strand of hair moved to the right side of her face. Ray reached out, swiping it behind her ear. Jennifer avoided the distraction of his moving hand. She glanced down, watching his cock pump up again. She parted her lips and flicked her tongue across the head each time it thrust up. Four licks were precisely enough to make Ray groan. His orgasm was drawing closer with each passing second, but he didn't want this pleasure to stop. There was no need to buck his hips. Jennifer was in full control, and he didn't want to interrupt her. She quit licking the head and raised her head. Her eyes glared at him as she spoke.
"You like that? You like these big tits wrapped around your nice, hard cock like this?"
"Yes!"
"Ohhhhhh, yeah? You like how I'm fucking your cock with my tits?"
"Fuck yes!!"
Jennifer giggled at his response. She pumped her tits faster, making more sounds in the friction. Ray grunted, wondering just how long he could last. It felt so good, he didn't want it to end, but time was drawing short. Over and over, she worked her tits. He was trying to hold himself back, but it was impossible. While it would've been easy to take control and pull his cock out, Ray chose not to. Jennifer was fully in control and was more than eager to make his cock explode. Again and again, she pushed her tits up and down. He gritted his teeth, snarling guttural moans as he tried to hold himself back.
"OHHHH!! OHHHHHH, GOD!!"
His loud screams were met with the full force of her breasts sliding up and down his hard cock. Jennifer moved faster, eyes locked on him as a big grin ran across her face. She wanted this as much as he did. Ray's eyes widened as his cock began erupting between her tits. A hot spurt of cum flew up, splattering under her chin and drenching her neck. Jennifer continued to work her tits, forcing out another wad of cum that went across her collarbone. Ray's eyes widened again in complete shock that she continued to pump her tits up and down. Jennifer used her breasts to milk his cock, forcing out more spurts of cum that struck her neck. With her head raised, she didn't worry about any of his gooey white seed touching her face. Some of his cum oozed between her tits, making it even easier for his cock to glide back and forth. Jennifer began to giggle as she loosened the grip of her tits.
"Look at all this cum. You gave me a nice pearl necklace and then some."
She let go of her tits, finally letting his cock free from between them. Ray sat there and watched as she gripped his shaft with her right hand, squeezing it hard to force out a few more drops. With her other arm, Jennifer propped her tits up over the forearm. She guided his cock against her right nipple, playfully smearing his cum across it. Jennifer moved his cock to her other tit. Across the areola she rubbed his cock and then smacked the head against her nipple. Ray's eyes met hers, and Jennifer bit her lower lip. Below her face was all the cum dripping down her neck. Between her tits was a line streaming down to her stomach.
"Let's take a little break. You need to get hard again. I'm going to get cleaned up, so while I'm away for a bit, think about how you want to fuck me. I'm going to let you decide how you want me."
Placing her hands on his legs, Jennifer lifted herself up. She turned around and began stomping her way back to the kitchen. Ray let out a sigh and called out to her.
"Hey Jennifer, I've got something to tell you."
Flipping her hair to the side, she turned and glanced at him across her right shoulder. Ray grinned.
"You're a fucking MILF."
With a smirk across her face, she raised her right hand and blew him a kiss. That was her way of silently replying. Her heels were heard stomping loudly across the kitchen floor. Ray got up from the couch, standing on his feet as he thought about her. Loud stomps from her heels were the only thing he could hear from the other room. Those noises alone made his cock spring back to life with a new level of hardness. With a deep breath, he believed he was ready for the second round of sex. How did he want to take her? Right from behind. That was his first thought. It was his favorite position from watching porn. Ray had always dreamed of fucking a MILF from behind and making her big tits bounce all around. He couldn't wait to do it to Jennifer.
"Hey Ray! You still in there!?"
Her voice called to him from the kitchen.
"I haven't gone anywhere, Jennifer!"
"You want another glass of wine!?"
"No, I'm fine!"
She didn't yell back at him from the other room. Ray let out a sigh, thinking to himself that she was drinking in the kitchen. After a few seconds, her heels were heard again. She strutted back into the living room holding the bottle in her right hand. Her breast and neck were clean. She must have used a cloth or towel to wipe her skin, he thought to himself. Ray stepped closer as Jennifer raised the bottle to the edge of her lips and had another drink. She swallowed and handed him the bottle.
"Are you sure you don't want another sip of this?"
"I told you I was fine."
Taking the bottle from her, he moved behind her and slapped his free hand across her bum. Jennifer pouted in response to the spank.
"Ohhhhh, you are one naughty, bad boy."
He placed the wine bottle on the table near the couch. Jennifer was walking towards the couch when Ray reached out and spanked that ass a second time. She whimpered an exaggerated moan, spreading her legs and bending over to push out her rear. Jennifer seemed to know from his touch that he wanted to admire her ass. The cheeks pushed out, splitting down the crack. She glanced across her right shoulder and backed up, rubbing her ass against his left leg.
"Do you want to fuck me, Ray?"
"Yes I do."
"Good. I told you to think about how you wanted to take me. I had all last night to think about how bad I wanted you to fuck me. So how do you want me?"
"Right here is good enough. I want to take you from behind."
Jennifer laughed.
"Oh, yeah? Is that how you want me? Doggy style? Now you have me wondering something. Is this how you liked to fuck your girlfriend?"
Without replying to her teasing, Ray stepped behind her and gripped his cock. He gave it a few strokes before guiding it between her thighs. The wetness of her pink folds was a fine invitation to slip inside her delightful entrance. Jennifer raised her head and let out a sharp moan as his cock sank into her. She was tighter than he anticipated. Gripping her hips, Ray made the first full thrust into her. Jennifer gasped and then moaned. Her hands pressed down into the cushion of the couch. She lowered her head and raised her ass up.
"Fuck me. Fuck me, Ray. Just give it to me like you've always wanted to. Fuck me like you used to do Lexi."
Hearing that name again annoyed Ray. He drew his right hand back and smacked her ass.
"I want to forget about her. You're better than her."
Since she made multiple mentions of his ex, he felt inclined to start teasing her about her husband. With another hard thrust, he placed his hand back on her hip. Jennifer moaned and pushed back, meeting his thrusts as their bodies were now moving in sync.
"You like that, Jennifer?"
Another slap across her ass followed with hard thrusts forward. Her breasts were shaking, jiggling all around as Ray found the rhythm he wanted with pumping in and out of her tight pussy.
"Does your husband call you a MILF?"
A moan from her soft voice was the only reply Ray received. He reached for her auburn-dyed locks of brunette hair. The grip made Jennifer cry out as she raised her head.
"Mmmmmmmm, yeah."
"Yes, he calls you a MILF?
"Nope!"
Glancing at him from across her right shoulder, Jennifer gripped.
"You're the first one to ever call me that while fucking me! Come on, Ray! I'm your MILF, and that means you better fuck me like one! Fuck me!!"
Her words brought a new rise out of him. Ray gritted his teeth and grunted as he bucked his hips harder and faster. His balls smacked against the undersides of her firm ass. Jennifer kept her head raised as she took every thrust he delivered. Again and again, his cock pumped into her pussy. He released the grip of her hair after one final rough tug. Her breasts jiggled and shook around until Ray's hands moved underneath to grab hold of them. He pinched both nipples as she squealed loudly.
"OHHHHHHHHH!! YESSSSSSSSSS!!"
Gasping for breath, Jennifer lowered her head. Ray squeezed her tits and leaned forward, brushing his stomach against her back as he continued to thrust into her pussy.
"FUCK ME, RAY!! JUST LIKE THAT!! FUCK ME, FUCK ME!! OHHHH GOD, FUCK ME!!"
The more she screamed, the harder he thrust. Ray let go of her tits so he could pound into her at a faster pace. His right arm wrapped around her stomach, feeling her tits flap up against his forearm. Her hands slid across the cushion, lowering her head further. She tried to push herself back and match his thrusts again. Ray proved to be in control as he thrust away, driving his shaft in and out of her pussy. He wanted to hear her scream again. Only two words mattered to Ray.
"Scream for me, Jennifer! Tell me to keep fucking you! I want you to fucking scream those words!!"
"YES!! KEEP FUCKING ME!! FUCK ME!! FUCK MEEEEEEE!!"
Hearing her utter those important words made Ray reach for her hair again. He snatched a tight grip with his right and then used his left hand to spank that ass one last time. His palm was stinging as he gripped her hip again and resumed thrusting. Jennifer's climax was drawing closer with each thrust he gave her. Ray was certain that she was getting close based on all the screaming that echoed throughout the house.
"DON'T STOP!! OH MY GOD, PLEASE DON'T STOP!! GIVE IT TO ME!! GIVE IT TO ME GOOD!! FUCK ME, RAY!! FUCK ME!!"
It was a good thing she had made him blow a load earlier. That made it easier for Ray to hold himself back as he felt another surge of fresh cum flowing from within. He wanted to blast an even greater load all over this wonderful woman. The first order of business was delivering an unforgettable orgasm to her. He knew Jennifer was close as she buried her head down into the couch cushions and spread her legs out even further. For a brief moment, the only sound heard was the rhythmic smacking sounds of their bodies colliding. Smack. Smack. Smack. Following the sounds, she squealed, and that was when Ray felt her inner walls tightening around his shaft. That was the sign it was time to pull out.
"Oh, fuck!"
Quickly, Ray grabbed his cock from the base and carefully extracted it from Jennifer's pussy. Her teeth clenched together as she growled and let out a loud moan. He noticed the squirting juices running down her right thigh. He had pulled out just at the right time, or else he would've likely exploded inside her. That wasn't where he wanted his second load of the day. As he stood there, Jennifer let out a sigh. She didn't have to catch her breath. She seemed to recover so quickly as she turned her head and glared at him. Before he could react, she slid off the couch and turned around. Jennifer's knees hit the floor, and she reached for his cock with her right hand.
"You are bad."
Squeezing her fingers around his cock, she grinned and took a deep breath.
"I like a bad boy who knows how to use this."
The grip of her fingers stopped directly under the tip of his shaft. She pushed it against her lips and kissed it. That was Jennifer's way of referring to his pole with the last words of her statement. Parting her lips, she flicked her tongue across the head. Ray exhaled deeply as Jennifer's hand slid down to the base. She licked the underside of his shaft, raising her tongue back to the head before enveloping her lips around it. Ray ran his left hand through a few locks of her amber-colored hair as Jennifer pushed his cock into her mouth. She sucked it lovingly at a slow pace. 'Mmmmmmmmm,' a long, low muffled moan came from her voice. Jennifer released the grip of her fingers and pressed her palms against his legs. Since he was standing, Jennifer had an easier time bobbing her head up and down at a fast pace.
"Fuck..."
As Ray groaned, she sucked harder and faster. Was she trying to make him shoot a load down her throat? That was the question Ray asked himself. He was in disbelief at her sultry prowess. The way Jennifer had quickly recovered from her orgasm and fell to her knees left Ray in disbelief. She was living up to all the fantasies he had about what a proper MILF was. Jennifer pushed his cock down her throat, once again sucking every last inch. Ray's hands moved to the side of her head, gently pressing down. That seemed to encourage Jennifer to deepthroat his full length a bit longer. As she withdrew it from her lips, Ray lowered his hands. Jennifer gazed up at him with her dark eyes. With a nod, he knew where he wanted his cock next.
"Come on, babe. Wrap those big fucking titties around my dick again. I need to feel that again."
Jennifer released his shaft from her lips with a pop and leaned up. Her hands gripped her breasts, pulling them apart for him. Ray helped her by guiding his cock between them. He pulled his fingers away to watch her breasts smother his cock between them.
"This time you're doing the work. I already did this earlier, so it's your turn."
"That's fine by me."
She grinned while squeezing her breasts tightly around his shaft. Some locks of hair moved closer to her face. Ray brushed them aside, moving the hair behind her right shoulder. Jennifer smiled as he bucked his hips to make his cock thrust between her tits.
"Fuck my tits."
Hearing her utter those words only made Ray thrust harder and faster. Jennifer maintained eye contact as if she refused to glance away from his face. Her lips curved into a seductive grin, flashing her teeth.
"You're loving this, aren't you?"
"Yeah!"
Jennifer laughed as he continued pumping his dick between her boobs.
"Your cock fits so nicely between my tits. You could say I was built for doing this since you like calling me a MILF."
Giggling at her own words, Jennifer made him thrust even faster. Ray lost control of himself, no longer caring if he was going to cum again. This time he was going to pull out and make a mess somewhere else besides her neck. Jennifer smirked as his face contorted, muscles twitching as he grunted. She didn't say a single word upon noticing how close he was. His cock moved back and forth, thrusting up and down. Swallowing his breath, Ray had to make a decision in split seconds.
"Jennifer! I'm gonna cum real fucking soon!"
Her reaction was to only smile at him.
"Oh, yeah? Where do you want to cum, Ray?
His cock was still pumping between her tits as he replied.
"Your face!"
Jennifer pulled her breasts apart. His cock flopped out until Ray gripped it with his hand. Without saying a word, she closed her eyes and held her face up. The smile was still there as Ray aimed his cock directly at her face and stroked.
"Ohhhhhh, man. Ohhhhhhhh, yeah."
Exhaling deep breaths and grunting, he impatiently jerked his cock. It was only a shame that Jennifer couldn't witness the speed of motion as his hand became a blur. Her own hands pressed against her breasts, gently massaging them below. Another groan came from his voice as Ray watched the first string of cum shoot out of his cock. It landed across the left side of her face, directly under the eye. Another string followed, coating the left side of her nose. He used his left hand to gently grip the back of her head. Jennifer tilted her head up in time for a thick wad of cum to splatter across her forehead. He gritted his teeth, groaning loudly upon another spurt of cum that drenched her right cheek. Through it all, Jennifer's smile remained across her face. Ray could see she was no stranger to taking facials. He had to wonder when was the last time a lucky man like him was privileged with blowing his load across her face. He let go of her hair, breathing heavily as his fingers moved away from his cock. Jennifer's eyes opened, and she gazed up at him as his warm seed dripped from her face.
There was nothing to say as she revealed her teeth in a full smile. Her expression told him that they weren't done yet. Even with a fresh load of cum on her face, it was clear that she wanted more. Using both hands, Jennifer gripped his cock and began twisting her fingers around it. She leaned in, kissing the head before pushing it between her lips. Jennifer sucked out the final drops of his cum and then pulled his shaft from her lips. She spit out the last few drops, allowing the cum to trickle from her lower lip and drip down her chin. Ray stood there, taking in the sight as a mental image. It was something he hoped he would never forget throughout his lifetime. Jennifer was the first woman in his life to get him to cum twice. All done in the span of an hour's time. She released his shaft from her hands after another soft kiss to the tip. He moved to the couch, sitting down as she remained down on the floor. Jennifer didn't appear phased at all by the mess splattered across her gorgeous face. She let all the warm streams run down her pale skin. Moving closer to him, Jennifer grasped for his cock with her right hand and situated herself in front of his knees.
"You blew a huge load for me. Not once, but twice."
Ray chuckled.
"Yeah. You got more out of me than I thought possible."
Giggling at him, Jennifer flashed her teeth. She pumped her fingers up and down, jerking him fast to harden his cock for another round. Ray was regaining his breath when he realized what Jennifer was doing. Her eyes focused on his face as she spoke again.
"I'm not done with you yet. You had to travel a long way out of town to fuck me. You've had your fun with fucking my tits and cumming all over my face. Now it's my turn to have fun. Just sit back and relax. It's my turn to be in control. I'm going to give you a ride that you'll never forget."
Rising up from the floor, Jennifer spread her legs and revealed her wet pussy. It was, by far, the greatest sight he had of her vulva all day. Ray couldn't react as she straddled his lap and began to lower herself down on his cock. The head slipped past her pretty pink folds, and then he gasped. By the time he recovered his breath, Jennifer had bent her knees and was on top of him. She moved her hand away from his shaft and pressed both palms against his chest. Her fingernails lightly grazed his skin, running down. Ray stared at her cum-coated face. He ran his right hand through her hair, rustling a few of those orange locks around as Jennifer began rolling her hips. She pressed down on him as she found a rhythm fucking him.
"Oh, god! Fuck!!"
By complete surprise, she took control of him. Ray was slightly fatigued after how hard he came minutes earlier. Jennifer had taken full advantage of that moment and had the young man right where she wanted him. Over and over, she rolled her hips and bounced up and down on his cock. Ray could feel his cock hitting spots inside her that he didn't know were possible. She moaned, cried, and whimpered. Raising her arms, Jennifer moved them behind her head and leaned up to allow her epic breasts to bounce. They flapped up and down, smacking loudly against her skin. Ray was mesmerized by the sight of her boobs bouncing until he reached for them and grabbed hold. He squeezed them as she cried out.
"Ohhhhhh, yeah! OHHHHHHHHH, YES!! YESSSSSSSSSSS!!"
Her voice elevated to a higher pitch, almost as if she were singing in key to a loud chorus in the background. Ray fondled her tits, squeezing them again before letting go. His hands moved to her hips, and then he made the bold decision to begin thrusting upward. Jennifer gasped as his cock moved inside her, thrusting back and forth. They were now working in a rhythm, not unlike the previous position where he had control. She leaned back and placed her hands against his knees and stretched her body back. This move gave Ray a glorious sight of his cock buried inside her pussy. It made him want to thrust harder and faster. Her breasts lay against her chest and jiggled around as he continued thrusting.
"THAT'S IT, RAY!! FUCK ME!! YOU CAN DO IT!! YOU AREN'T TIRED YET, SO GIVE IT TO ME!! GIVE ME EVERYTHING YOU GOT!! FUCK ME HARD UNTIL WE BOTH CUM!! FUCK MEEEEEEE!!"
Every last word she screamed at him served as a boost of motivation. No matter how tired he was earlier, it was all over now. Ray focused on the sight of her tight pussy as his cock pumped in and out. He leaned forward, shifting his hands underneath her to hold her thick ass cheeks. Jennifer began to lean up and pressed her hands against his chest again. She shoved him back down into the couch and regained control. Ray quit thrusting as she bounced herself up and down, riding his cock with hard thrusts. The sound of their bodies hitting together was heard yet again through all the moans, cries, and deep breaths. Jennifer was on a mission to reach her second climax of the day. Ray was strong enough to go through two, so he believed he could take a third. If she wanted him to cum inside her, then it was entirely her choice by demand. He had a strong feeling that was what she wanted from the sheer force of how she pounded herself down on his cock.
"YES!! YESSSSS!! OHHHHH MY FUCKING GOD!! YESSSSSSSSSSSSSS!!"
Jennifer's tits shook wildly, and her hair went flying everywhere. Some locks stuck to her face due to the cum that was still drenched across her cheeks and forehead. It was clear to him that she didn't care. Jennifer screamed again as she continued to slam herself down on him.
"OHHHHHH, YEAH!! HERE IT COMES!! I HOPE YOU'RE READY!!"
No need to ask. He already knew what she was referring to. Ray closed his eyes as his face scrunched up. Jennifer showed him no mercy as she continued to rock back and forth. Over and over, she slammed down on his cock until he was screeching a series of loud moans.
"FUCK!! JENNIFER!! OH MY FUCKING GOD, I THINK I'M GONNA--"
His voice was drowned out by her screams that were much louder.
"YESSSSS!! GIVE IT TO ME!!"
Ray's eyes opened wide to the sight of her huge tits as he let go. Jennifer raised her head and ran her hands through her hair as they both reached this climax together. It was his third load of the day, and Ray screamed for dear life as he felt it mixing with her warm juices inside her. This feeling was even greater than the previous two. He was lost in this heavenly sensation, unable to snap out of the ecstasy as it overwhelmed his body.
"Jennifer!! Oh my god! Jennifer! Ohhhhhhh, god... Jennifer... Jennifer... Jennifer..."
Uttering her name several times was all he could do. There was nothing greater than this pleasure. Jennifer had delivered unto him the ultimate experience that no fantasy could compare to. Never in his wildest dreams did he imagine feeling such passion through the act of sex like this. They did more than just fucking. She made him feel like a man to the point that he wondered if this was what it meant to be loved. If this was her way of repairing his broken heart, she had done more than a good job. His ex-girlfriend was all but a distant memory now.
******************
1 WEEK LATER
Los Angeles, California
Back at work, the freezing cold mornings had been replaced by moderately cool temperatures. It was a welcoming relief to be back in the warm sunshine that only California could bring. Returning to L.A. to go back to work, Ray felt his life had changed for the better. At first, he feared that it would be awkward to interact with Jennifer on the set after the affair they had. He was kept away from her with different jobs from his supervisor for a few days. That was good enough to ease off some of the tension he felt. Ray knew he had to avoid becoming obsessed with a married woman. Before he left that day, Jennifer kissed him and said she would keep in contact. It was just a day spent between two friends and nothing more. She had ignited something within him, as he felt more attraction to older women than he ever did before. The one thing Ray was certain about regarding his future was that he wouldn't waste his time dating another girl in her twenties. He went to sleep at night fantasizing about being in the loving arms of an older woman.
A MILF, to be more specific. Jennifer had exceeded all expectations he had from his fantasies. Valentine's Day was the next holiday on the calendar. While he was currently single, Ray thought about Jennifer. She was the closest thing he had to a real Valentine and the only woman worth spending his hard earned money on a nice gift. He remembered her tumbler cup and the little heart on it with her initials. That was all the inspiration he needed for going out and paying for a personalized T-shirt. Since she had a husband back home, Ray knew he had to deliver this gift early and away from the watchful eyes of anyone else. The shirt was wrapped in a thin plastic layer. Ray put it in a red gift bag. He stood around the parking lot waiting for Jennifer to come out. When he saw her in the distance, he smiled. Her legs were hidden in a blue dress. No cleavage on display, but her amber locks of hair made him smile. The outfit made her look like a housewife, reminding him of his own fantasy. The dress matched her new purse that was hanging over her right shoulder. Jennifer smiled, waving at him.
"Hey you."
"Hey there, Jennifer. Are you heading home?"
"Not just yet. I have to make a stop and pick up some stuff for the house. I'm going to be busy cooking tomorrow."
Ray smiled and nodded.
"You do know how to cook an awesome meal."
Jennifer blushed.
"Thank you."
He reached out, offering her the gift bag.
"Is this for me?"
She already knew the answer to that question, but Jennifer knew how to tease him. Ray nodded as he tried not to blush.
"Yeah. Consider it a Valentine's Day present. I made sure to give it to you early, since I know you're married."
"How very thoughtful of you."
"I hope you like it."
"I'm sure I will. Catch you tomorrow, Ray."
"Text me anytime, Jennifer."
As he walked away, she held the bag in both hands. Maybe she would text him as Valentine's Day drew closer. Her heels clacked against the pavement as Jennifer opened the driver's door of her car and climbed in. She waited until the door was closed and then opened the bag. Ray was nowhere to be seen in the parking lot as she pulled out the shirt. She already knew what it was based on the way it was folded within the white plastic bag. The fabric was white with some design printed on it. Jennifer unfolded the shirt, and then her lower lip fell as she saw the red heart. Over it was black ink with a single word on it: MILF.
"Oh my god... That naughty, naughty boy."
She bit her lower lip and exhaled a deep breath. No one was there to witness the big grin across her face.
"Oh, Ray... My hubby is gonna love this."
THE END
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Delicious stuff! Another fantastic read.
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Fuck that was hot. The way you ended this, do you have plans for more? I'm wondering what happens next with Ray and Jennifer. It don't sound like she is done with her new boy on the side.