Thanks to Literotica member Smoothed for his editing and creative input.
*****
When Tiffany was twenty, she married “Famous Larry,” a self-made millionaire whose chain of used car dealerships had made him somewhat famous in several southwestern cities. They met on a beach near Panama City, Florida, where Tiffany was waiting in line for ice cream with friends. Larry walked up to her and offered to buy her a car if she would go on a date with him. Even though his offer was outrageous, it was so crazy that it caught Tiffany’s attention.
Larry showered Tiffany with gifts, money and affection, and it didn’t hurt that he wasn’t ugly and was good in bed. After six months of dating, Larry proposed to her with a three-carat emerald-cut diamond engagement ring. They flew to Las Vegas and married within forty-eight hours of his proposal. The newlyweds are happy, in love and have a very active sex life.
Larry was forty years old and already owned ten used car dealerships from Houston to Phoenix. He specializes in high-end used cars, but he never uses the term “used car” in any capacity. His dealerships only sold “used sports cars and luxury cars,” and he sold a lot of them. BMW, Mercedes-Benz, Jaguar, Lexus, Range Rover, Maserati, Cadillac, he has any car you can think of, or if the price is right, he will buy it for you. Tiffany quickly became accustomed to the lavish lifestyle offered by Larry’s business.
Tiffany has an amazing figure. Five foot eight, one hundred and forty pounds, with dark red hair and green eyes; huge, natural, 38E breasts; slim waist and round ass, she has been fending off men for years. A few years later, her friends told her she could play the slightly thinner stand-in role for actress Christina Hendricks in the Mad Men series. Tiffany and Larry soon gave birth to their only son, Ben, who was born a year after their wedding.
After Ben was born, the couple decided not to have any more children. Mainly because Tiffany found it almost impossible to handle it all. After Ben was born, Larry had a vasectomy, putting the matter to rest forever. When Ben entered high school, Tiffany and Larry’s sex life began to wane. Larry is in his fifties and spends most of his time focusing on expanding his car business and his twenty-four-year-old mistress. Sex with Tiffany was no longer a priority for him, and Tiffany turned to reading romance novels, erotic novels, and masturbating with a vibrator.
Ben got into trouble in high school because he was smoking marijuana, drinking heavily, skipping classes, and despite being extremely smart and capable of getting high grades, he graduated with a 2.8 GPA. It was pure luck that he was able to get into a major university in California. Aside from his poor performance in high school, Larry and Tiffany are proud of their son and are making sure that his first year in college is as stress-free as possible. Ben’s father not only paid for his college tuition, but also gave him $40,000 in spending money for clothes, football games, and other social and miscellaneous expenses. Everything is set.
Ben’s parents sent him to school with high expectations. He has all the resources he needs to succeed as a freshman. Everyone has high expectations for the handsome son of “Famous Larry.”
A year later, Larry and Tiffany went home with their son, humiliated and disappointed. His first year of college was a total waste.
Ben had spent $40,000 on marijuana, alcohol, road trips, and taking friends out to fancy restaurants. His father was able to check his grades online and was surprised to see that his son had received three “Ds”, two “Fs”, and one “Incomplete” due to absences. Larry was ashamed of his son. If his grades were good, money would not be a problem. He had envisioned Ben becoming a lawyer, or getting an MBA and helping him start a business. Not only were his grades poor, but he also wasted thousands of his father’s dollars with no results.
Now, Ben has just returned from an unsuccessful first year and is back home in his spacious bedroom. He was unemployed, had no plans for the future, and didn’t have a lot of friends. Thankfully, he still has his friend Alex. Ben has been talking to Alex regularly since he got home from school. Alex decided to take a gap year before going to college and found a way to make a lot of money in the meantime.
“Let me tell you this, Alex, you and Taylor are making videos and selling them on this website?”
The two friends were browsing an amateur porn site called “Hot Amateurs” on Alex’s laptop. It is a website that specializes in high-quality homemade porn videos that customers can purchase in a single download to their computer. Alex and his girlfriend Taylor are selling videos on the site and making a lot of money.
“How much does one of your videos cost?” Ben was intrigued. To the nineteen-year-old, this sounded like easy money.
“It depends. They take about 50 percent of each sale because they take care of the website, payment processing, advertising, and all other logistics.”
“Then, you’ll take care of it once the recording is over, right?” Ben confirmed.
“Yeah. Sometimes we would hold the camera in turns so it was like perspective, but sometimes we used tripods and one time someone videotaped us; that was our best video.”
“Who has the camera?” Ben was completely mesmerized by his friend’s new career.
“A woman responded to an ad we posted online.”
Alex continued, “Tyler and I have over thirty videos. Some are long, like thirty minute sex scenes, and some are short solos of Taylor, or me masturbating, or quick videos of the two of us. We price the short videos at twenty dollars and the long ones at thirty to fifty, depending on what we do.”
“Every video?” Ben asked.
“Yes, but once they download it, it’s theirs,” Alex confirmed.
“How much did you sell it for?”
“As of a few days ago, there were over seven thousand four hundred.”
Ben paused and calculated, “You made about $150,000 in eight months?” Ben couldn’t believe what he was hearing.
“No, it took us about six months… and the money kept coming in because the videos were still being sold and downloaded all the time.”
Alex pulled out his laptop and showed her his personal account on the site, which provided information about video statistics, revenue and other similar data. He showed a video of Taylor masturbating, which sold for $22.
“She’s so hot, bro.” Ben punched Alex.
“Thank you.”
Ben watched as Tyler entered a purple room with a black and white bean bag chair in the middle. She sat down in the chair and lifted her skirt up, revealing her clean shaved pussy. She spread her legs and began rubbing her clit, the camera slowly zooming in on her pussy. She moaned as if her brother was holding the camera in some sort of role play scenario. The video only lasted fifteen minutes and ended with her cumming and squirting on the floor.
“Wow! So, if I want that video, do I download it to my computer?”
“Yes, well, after making a purchase using a credit card or online payment service.”
“Twenty-two dollars…you made eleven dollars?”
“Ben, every sale is discounted.” Alex scrolled to a link to see a list of the videos he had.
“The video alone has been downloaded 133 times, and it took us about 30 minutes. Less than 30 minutes of work, and it cost over $1,000.”
Ben was stunned. The money was too good to be true. When Alex visited, he checked out the rest of their footage. Ben thinks Taylor has an amazing body and could do mainstream porn if she wanted to. Alex is muscular and has a huge cock. It was about eight inches and thick as a log. It’s no coincidence that their videos are hits.
Ben noticed that his own cock was longer than Alex’s and felt bigger. He was also much thinner and taller than Alex. Ben thought about the possibilities.
“I can do this, Alex.” He shut down Alex’s computer.
“Oh my god, yes, you can do it, but before you do that, you have to be aware of the fact that your naked body is going to be visible on free porn sites on the internet. You have to make sure that you’re okay with posting it before you decide to make any kind of video because millions of people are going to see your naked body.
It took Ben a while to think about what his friend had said.
“Why is this on a free porn site?”
“Many people buy videos and then upload them to free sites. You can contact these free sites and they will remove it, but it still happens.”
“What if I hide my face in the video so no one can recognize me?”
“They might not sell well either. If you have a gimmick, like wearing a mask because you fucked someone’s wife, or if there’s some other attraction, it could work. Most of the videos I’ve seen where people are masked or blurred out – their faces come from the cheating wife and incest role play categories.
“Incest? Really?” Ben didn’t believe his friend.
“Yes, there are a lot of couples pretending to be in a relationship and making fantasy role-play videos. Some show their faces, some don’t. According to the website, they are the best-sellers.”
“But people can access hundreds or even thousands of membership porn sites and pay twenty dollars to join, and then download dozens or even hundreds of videos for that price. Why should anyone go to Hot Amateurs?
“Because of the content. There is a huge market for what the site offers: private shows, unique amateurs, viewer-requested content and fantasies, especially incest role play. Most membership sites, even free porn sites, don’t allow them. It’s silly to upload step-family fantasies but not biological family fantasies, but it’s true what Alex says about the content and the whole point of the membership site.
“How do you know all of that? I mean, you and Taylor were making a boyfriend and girlfriend video.”
“No Ben, we make brother/sister, father/daughter, and mother/son fantasy videos. Mainstream sex videos don’t pay that well.”
“But you two aren’t old enough to pretend to be a mom or a dad yet.”
“There are ways to get around this, and you’re right, the bigger the age difference the better. Our mother and son videos sell the best though. This is my POV with the camera. You can only see my cock, so there’s no way for you to know how old I am anyway, it’s pure fantasy.”
Ben watched some of Alex and Tyler’s videos and understood the appeal. He really thrived on the role-playing aspect of the experience. The two friends discussed the recordings for another hour before Alex headed home.
After Alex leaves, Ben lies in bed thinking about Alex and Tyler’s video business. It’s an easy money venture that appeals to them. He can be his own boss, make a living off of sex and make a lot of money at the same time. He needs a few things: a camera, a female model or girlfriend willing to pose, and a set. He knows he can do it.
“Ben? Please come down for dinner!” Ben’s mom Tiffany was calling him down.
Despite his father’s ridicule and utter disappointment, Tiffany remained loyal to her son. She always defended him when his father asked him to leave the house. She felt sorry for Ben and was genuinely happy to have him with her. She is also a little angry at Ben for taking for granted everything he has given her in life so easily. Tiffany is a lonely woman, mainly due to her husband’s lifestyle, but also due to her own introverted personality.
Ben was working on a digital camera when he heard his mother’s voice and shut down his computer. He rushed down the stairs and went into the kitchen.
“Hi, Mom.” Ben was sitting in front of the huge white marble island in the kitchen.
His mother wore white shorts, white high-heeled sandals, and a navy blue top that showed a little bit of cleavage. She had her hair up in a bun, which highlighted the contrast between the ivory skin of her neck and her dark red hair. Ben loved watching his mother work in the kitchen. She loved wearing shorts, skirts, and skorts that showed off her sexy legs and curvy ass. Her huge, shapely breasts were out of this world. They hung low enough to show that they were natural, but firm enough to stay away from her body. The thought of her huge breasts made him cum many times. Ben still actively fantasizes about his mother.
“Where’s Dad?” Ben looked around for any sign of his father.
“He’s been visiting the store in Dallas. Their monthly is at an all-time high, so he’s thinking about buying a bigger lot and moving into a bigger building. He should go away for a few weeks. You should give him a call and see how it goes.”
“He didn’t want to listen to me. When I came back he ignored me for two whole weeks. He didn’t even talk to me! I don’t have any money, mom!”
“He was disappointed, Ben. He told me not to give you a dime. He said you need to get a job and start saving money. We’re all disappointed, Ben.”
“I know. I messed up.” Ben looked at the marble counter.
“I’m glad you realized that. Let’s spend this week trying to get you a good job. Please contact your father. You should regain his favor.”
“Okay, I’ll tell him when he comes back.”
Tiffany prepared tortillas and salsa for her son and began cleaning the countertop near the stove.
Ben watched his mother bend over and put dishes in the dishwasher. He looked at her top as she bent over to remove the bowl. Her breasts moved around as she worked.
“She’s so sexy.” When Ben came home after not seeing his mom for almost a year, he remembered how sexy she was. She was the sexiest, most sensual woman he had ever seen.
After dinner, Ben returned to his room and found that a local store had a camera he wanted to buy. Alex gave him a few models suitable for HD recording, but they weren’t cheap. The model he wanted cost around two thousand dollars. It would be a great camera for what he wanted to do. Now he just had to get the money.
Ben’s bedroom is on the top floor, across from his parents’ master bedroom. He came down and asked his mother if there was anything he could do, either borrow two thousand dollars from her, or just let her buy the camera. If he couldn’t get the money from his mother, he would have to find a job to save up for the camera.
Larry and Tiffany’s home is just over 8,000 square feet and is called a “mini mansion” by Ben’s high school friends. As he walked down the hallway toward the stairs and finally to his mother’s master bedroom, he wrote down a few places he could record, if only he had a camera. Ben walked into the master suite and found his mother, wrapped in a towel, coming into the bedroom from the shower.
“Ben! Oh my god! Please knock on the door!” She took a step back and tiptoed across the room to the closet to get her cloak. Ben saw her almost slip out of the towel, but to his dismay, he managed to keep her body from being exposed. She emerged from the closet wearing a cloak that hugged her curvaceous body.
“I’m sorry, Mom.” Ben pretended to cover his eyes.
He had come close to seeing his mother naked many times throughout his life, but he had never actually seen what she was willing to display in her everyday attire. Two years ago, he would often spy on her when his father was out. She liked to wear clothes around the house that suited her figure, which gave Ben plenty of masturbation pictures, but he wanted to see her nude, which never actually happened. Ben stopped his spying when he was caught peeping around the corner of her room and was told that if he did it again he would be sent to a military boarding school.
“What do you want!” said Tiffany.
It wasn’t the best time to ask for money, but if he wanted to start making serious money, he needed to start recording immediately. Not only did he want money to live on, but he also wanted to pay back his father for the money he spent, and eventually use the money he earned to pay for his college. That’s a very ambitious idea.
“Mom, I have a chance to make some good money, but I need a little cash to get started.”
“No, Ben, your dad said there’s no money. You have to get a job or spend the last penny in your account. Just out of curiosity, what do you need the money for?”
“I needed a camera to make videos for a project that could make me a lot of money.”
“I can’t give you any money, and even if I could I wouldn’t. Your father said you would never get a penny under any circumstances, Tiffany wasn’t in the mood to play games, especially after Ben came over.”
Ben knew that, where money was concerned, his mother would never make a major purchase without his father’s permission.
“Wait, there’s still money in my account? I thought Dad closed it?”
“No, he won’t give it to you anymore. Your account is still there.”
Ben quickly went upstairs to check his bank account online.
“Fuck yes, $2,675.66. That’s enough!”
Ben quickly left the electronics store before it closed and returned with his camera. He spent the entire night watching online videos on how to operate it. The next day, Ben looked for video ideas on amateur porn sites. He visited the “Hot Amateurs” website several times and got a better sense of the services they offer. They sell every type of adult material you can think of, and a lot more you never even realized were available.
Ben says that the most popular categories in terms of the number of films offered are MILF and incest role play. He wanted to know how he could break into these categories and maximize his sales potential. He immediately thought of his mother. He really wanted to film his mother.
“She’s so perfect,” he thought. But he knew his mother. She was very upset about her father and Ben’s last year in college. Even under ideal circumstances, there’s no way she would allow anyone to take her picture, let alone film her body. She can wear sexy outfits at home, but when she goes out in public, she’s always careful about how much of her body is exposed.
Ben opened an account on the site and entered his banking information to use the direct deposit feature. It took him two hours to get everything in order to even consider recording.
Now that he is more familiar with the camera, he wants to try it out and upload videos to see if he can sell them. He wanted to try filming an explicit video to spy on his mom. Unfortunately, she was in her room with the door closed and he wanted to film something right away. Instead, he thought he would make a solo video of himself masturbating. He remembered that Alex had said he had some videos of him masturbating. Ben figured he could sell at least some of these videos too, since he has a big penis and a curvy body.
He set up the camera on a tripod he found in a hall closet and placed it on a brown leather loveseat against the room’s wall, opposite the door. He makes sure the camera is focused and on the right setting for the light available in the scene. To make sure his first recording session wasn’t too dark, he had to bring in more lights, including floor lamps and table lamps in the lobby.
