$18.47

This story is for the Winter Holiday Contest 2023. This is a work of fiction. All people having sex are over the age of 18. No Anal and no group sex. My romance stores have some sex in the early part of my stories and then the action heats up. You will not be disappointed. I was not an English major in college so please forgive any typos, grammar and punctuation errors. Any of these errors should not take away from enjoying reading $18.47. Your comments and ratings are always appreciated. If only things like this happened in the real world! Relax and enjoy. Have a happy holiday season. NYBoss

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Benjamin Ross was getting annoyed. He was on line at the ShopRite in Monticello, New York trying to pay for a few items he needed to restock his home a few miles from the store. He had built a nice second home for himself, his wife and child. The home was to be a welcome retreat from his house in Scarsdale and his work in New York City. However, he became a victim of life's circumstances when his wife and child were T-boned three years ago. Ever since then, he rarely came to Monticello except for a couple of weeks, toward the end of the year. He liked the solitude and quiet this home and Monticello provided. But this year he planned to take up to seven weeks away from his company. He needed a break.

He remembered visiting the area when his grandparents rented a bungalow for the summer in Loch Sheldrake. His parents also rented a bungalow and summered there until Ben was fourteen. When he could afford it, Ben bought the property and built this magnificent home. He was a star on Wall Street. He developed many algorithms and systems that companies used to increase their production of whatever product they were known for. He was forty years old wealthy and lonely.

It was the Saturday after Thanksgiving and already winter was calling. There were a few inches of snow on the ground and the weather forecasters were calling for another two or three later that evening. The temperature was hovering around 25 degrees and it surely will get down into the teens. Ben had told his employees that he was going to be off for the rest of the year and that they would be able to take the time between the day before Christmas and January 2 off as company paid time off. His people worked hard and he was quick to reward them, whether by paying them very well or by extra time off. Or both. He said that his second in command, Robert Mathers would handle any questions until he returned back to work on January 3.

It seemed like forever, but it was only a minute and he shook his head and wondered what the problem was. By the looks of it, there was a woman, just in front of him, dressed in, what he would describe as, torn rags while wearing a wool knit cap. Her hands looked red and raw appearing as though she had not worn any gloves.

She was pleading with the cashier that the money she gave him was all that she had, needing an additional $18.47 to complete the transition. "Please, I need the food to feed my daughter. This is all the money I have." She was crying while yelling at the cashier.

"You can put things back," the cashier said.

"This food has to last me a week. I can't put anything back."

Ben looked at what was on the conveyor belt and there were a few loaves of bread, peanut butter, breakfast cereal and some milk. There was Jello and canned fruit.

"Miss," the cashier, showing some empathy said, "I'm sorry. I can't do anything about this. You're holding up the line and if I have to I'll call security."

Ben chimed in. "Excuse me. How much does she need?" He wanted to get out of the store, and he only had ten items to check.

"$18.47."

He handed the cashier a $20 bill and said, "Please pack up her food. Use these bags, the store bags," he pointed to. He gave the cashier another $5 to cover those costs.

The woman turned to him and said "Thank you."

Ben saw that this red head would probably be pretty if she took care of herself. She looked like a homeless person. "Here take this." He handed her a $100 bill. She couldn't speak. "Can I take you to your daughter?"

"I'm good, thank you," as she ran out of the store with her food.

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Ben caught up on his reading and walking on his five-acre property. He needed to get a dog, he thought. He had not gotten back into the dating scene since his wife and child's death and, quite frankly, did not have an interest in pursuing dating, yet alone a romance. Yes, he had a few dates, and a few sexual adventures but nothing that would last. He thought he had a keeper when he dated Dr. Cindy Harmon. They met at a fund raiser for the environment. The fund raiser was last year at the Essex House on Central Park South.

At the bar he was minding his own business when this drop dead gorgeous looking blonde, Dr. Cindy Harmon walks up and stops next to him and begins to order a glass of wine. He hears what she is ordering and says to her, "Try the Newton Unfiltered Chardonnay. It's an amazing wine."

"Sounds good," as she asked the bartender for a glass.

"I'm sorry Miss, but that wine is not what we are offering tonight."

"Can you get me a bottle?" He handed the bartender a $20 bill. He put his credit card down, a black American Express card when the bottle arrived.

"I see you are Dr. Cindy Harmon," looking at her name tag. "I'm..."

"I know who you are, Benjamin Ross. I read the financial magazines. Do you think I'm just a good looking blonde with a killer body and no brains," she laughed.

"Yes, yes and definitely no." Now they both laughed.

They blew off the dinner and wound up in Ben's suite.

"Sit back and enjoy," Cindy said. Ben had already taken off his shoes and socks. His tuxedo bowtie was long since gone and his shirt was open.

Cindy reached around her back and lowered her zipper. She stepped out of her cocktail dress and stood nude before him. Her tits were round and large with nipples that were now standing at attention. Large thick nubs on pink colored aureole. Ben's eyes moved downward and he saw a nice thick pelt of naturally blonde pubic hair. Ben removed the rest of his clothes. He stood 6'3" and had some brown chest hair. The hair on his head was the same color. It was wavy and he had the fashionable permanent five o'clock shadow. Very handsome with a larger than average cock.

Cindy came forward and engulfed his cock in her mouth. Her sucking produced the desired effect in about two minutes as Ben's cock was very hard. When she released his cock, Ben took her arms and turned her around so she was now laying on the pillows.

Ben started to repay the same service as he first moved his mouth to her tits, fondling each of them, including teasing her nipples. Moving his mouth to her nipples, pulling and lightly biting them caused a moan coming from Cindy's mouth.

"Feels so good. Ben, your tongue feels so good on my nipples. Bite them harder. Oh fuck, soooooooooooo good."

Reluctantly, Ben moved from Cindy's tits to her pussy. He buried his face in her bush and ran his tongue down the center of her pussy. She was already soaking wet. He saw her lips opening and thrust a few fingers into her snatch. He began finger fucking her and she started screaming immediately. As her hips moved up and down on the bed, she was yelling, "Fuck my pussy. Shove your fingers in. Deeper, harder. Oh................so fucking good. More, more, please more. Ayeeeeeeeeeeeeeeeeeee."

While Ben continued with his fingers, he clamped his lips around Cindy's clitoris. He licked around the bud causing her to scream out her orgasm. "Fuck, Ben, I'm cumming. Your tongue is making me cum." Cindy was also playing with her massive tits. And then she came. "Ooooooooooohhhhhhhhhhhhhh, yes, yes, yes, I'm cumming, cumming on your tongue and your fingers." It was an explosion she had not felt in years.

Thirty seconds later she yelled at Ben, "I want you in me, right now. I want to feel your cock. I want to cum on your cock."

Ben easily slid into her wet pussy. He began thrusting slowly. Cindy cried out, "Faster, don't play around. Fuck me harder." Ben picked up the pace. He had Cindy screaming within minutes.

"Ooooooooooooh, God. Your cock feels so fucking good. Fuck me. Oh, fuck me. Take me. Make me cum. Ayeeeeeeeeeeeee."

Two minutes later, Ben's balls began to churn as he had the stirrings of cumming. "Cindy, I'm about to explode. Where?"

"Cum in me. I'm safe. I'm there. Cuumiiiiiiiiiiiiiiiiiiiiiiiiiiing. Fuck cumming on your cock. Give it to me. Now, now!"

"You're making me cum, Cindy. Cumming, cummiiiiiiiiiiiiiiiiing." He emptied his balls in her pussy as she came. The mutual orgasms were the best both felt in years.

They cuddled, made out for a while with Ben playing with Cindy's plush bush and finally they fell asleep.

When Ben woke up, Cindy had already showered and was dressed. "I've got to be in the office early. By the way, I'm a Neurologist working in a group on Park Avenue on the upper east side."

Ben said, "I hope last night was not a one-time adventure. I'd like to see you again."

"I feel the same way. How about dinner tonight. You pick the place. Anything but Mexican or Indian." She gave him her contact information and said, "Text me where and time. Any time after 7 PM is good."

She went over to him and kissed him passionately before she said good-bye.

Things between the two of them were great. They took long weekend vacations together. They enjoyed going to the theatre to Yankees games and to the movies. They fucked every chance they had. Ben loved fucking her from behind. As he thrust deep into her pussy, Cindy was frantic in building up to her impending orgasm. She loved feeling his seed plowing into her pussy and eventually down her thighs. It made her feel so sexy.

Then, one day, California came.

Over dinner, Cindy broke the news. They were building a new stroke center at UC-Berkeley and they wanted her to be head of the program. Cindy had been published and was an expert in the field. It was a once in a lifetime offer. She was leaving in two weeks. They talked about trying out a long- distance romance. When she went home that night she cried herself to sleep. It was not much better for Ben.

The relationship lasted only two months. The 3,000 miles apart felt like 10,000 miles. He went out to the west coast to visit a few times. The sex felt stiff, without passion.

They both agreed that it wasn't working and he left that night on a flight back to New York, thinking about the last few months and how happy he was, starting his life again. He also wondered if he would ever find someone like Cindy again.

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Ben spent the next couple of days catching up with his neighbors at Nelly's Sports Bar. He had dinner with a few of his neighbors and often got into good natured discussions on the politics of the day. Local mostly. He had read about homeless problems in the Times Herald. While this was not a major issue, it was still a concern. The mayor was working on cleaning up an old warehouse for use with the homeless. This approach was well received and the warehouse would be completed within the next 12 months. It was a time for Ben to relax before the new year began. He had many business opportunities early in the year and he would be traveling to meet with the C-Suite executives.

About a week before Christmas, he was, once again, in Shoprite and a similar scene unfolded, similar to the one some 10 days ago. This time, Ben had a dozen items to check out and was third in line. After two minutes of hearing the diatribe, he yelled, "ENOUGH!" He excused himself, cutting in front of the line to confront what turned out to be the same woman from 10 days ago, pleading for the cashier to let her get by with owing her a few dollars for food she had in her cart.

It was the first time he saw the face of the woman he helped 10 days ago. She had the same rags on, but without the hat. She was a striking red-head. "Again?" he asked her.

"I'm sorry, but I needed medication for my daughter and now I need food."

"Okay, I'll help out. Fill your cart up with everything you need, and I'll have it sent to your apartment."

She started to move away from Ben, but he reached out and grabbed her arm. "Now I get it. You are homeless and the food can't be delivered."

She started to cry.

"Please don't. I meant what I said. Fill up your cart with whatever you want. I have a place for you and your daughter."

"But I don't know you," she said.

"And I don't know you. So there has to be some sort of trust."

Mary Feeney looked up at Ben. She saw a handsome man, confident and at this stage of her life, while it was hard to trust anyone, she decided to take the chance.

"We will need to pick up my daughter when we leave here."

"You'll show me where," although he had an idea where she would take him.

Ben paid for the groceries and when they got into the car he introduced himself. She did the same, while taking down the hood of her sweatshirt. She was beautiful without make up.

Ben took 5 minutes to locate the place where many of the homeless of Monticello called home.

"You left your daughter by herself? How old is she?"

"She's 13 years old and I have people who keep an eye on her."

"I'm sorry. I shouldn't judge."

Mary liked that this man was not afraid to apologize. They arrived at a section where some of the city's homeless called home. She found her daughter, Callie where she expected her to be, in an area where she pitched a small tent. On either side of her tent was her protection. Men who looked after Mary and her daughter.

She called out to her daughter and told her to join them. Callie, 13 years old, was a spitting image of her mom. Red hair and was in the process of becoming beautiful. She was a lanky teen-age daughter that had just begun to develop into a young woman.

Mary introduced Callie to Ben.

"It's very nice to meet you Callie. I've heard only great things about you from your mom. You know, you are very fortunate to have such a great mom. I ran into your mom, for the second time at Shoprite where she got my attention, to say the least, and I thought it would be a good idea to bring you to a place where you would be warm and would not have to worry about food. Your mother is trusting me to do the right thing and I hope to do that."

"Mom, you hardly know this man and you trust him taking us somewhere?"

"What do we have to lose? We are homeless, no hope for our future so what do we have to lose?"

"How about our lives?"

"I'm willing to take the chance that he's a good guy. And, we'll have a warm room and food. Listen, if things don't work out, we can always go back to the streets, to our comfort zone."

Ben said, "If you don't want to stay where I take you, I'll take you back."

"Okay, let's go."

Mary and Callie were quiet during the twenty minute ride to Ben's house. When they stopped in the driveway, Mary said, "I thought you were taking us to a homeless shelter?"

"I can, but I thought this may be better."

Ben opened the door to his house and Mary and Callie stayed silent.

"Here, let me show you rooms you can have. Each room has its own bathroom. When they got to the top of the steps, Ben said, "This is my bedroom," as he pointed to the one at the far end of the hallway. There are three other bedrooms," once again, pointing to them. Chose two of them or all of them, if you want."

"We don't have much in the way of clothes and stuff, so perhaps we can share a room," Mary said.

"That's up to you, but that situation will be remedied shortly." Ben made a call.

"Laura, I need a big favor. I'm going to put Mary Feeny on the line. She and her daughter are staying at my place and they need clothing. Get their sizes and bring up everything they tell you they need. They will also need boots, a winter coat, hat and gloves. I need them here by the end of the day. Thanks, Laura. I owe you big time. I'm putting Mary on the phone."

"Mary, this is Laura, a friend of mine who makes things happen. She is going to get some clothing to you by the end of the day. Tell her what you need and don't be shy about it." He handed the phone to Mary and left the room.

About thirty minutes later Mary found Ben in his office, located on the first floor. She handed back his phone. "Thank you."

"I know that you probably want to get out of the rags you are wearing. There are robes in the bathrooms that you can use. Your clothes will be here by 5 PM. You and Callie can stay in your rooms until you get your clothing and I'll have dinner ready for 6 PM. Before you shower would you and Callie like some home made beef barley soup and a turkey sandwich?"

Mary went to get Callie and by the time they reached the kitchen Ben had three bowls of soup and some homemade bread ready.

"Take your time," Ben said. "The soup is very hot and there's more if you want it." Both Mary and Callie had not had a hot meal in forever. They continued to wolf the soup and bread down."

"Hey, I mean it. There's plenty more. Do you like it?"

"I'm sorry," Mary said. "But a hot meal has been so rare. It's delicious. Thank you.

"Callie, take your time."

Callie looked up, not eating as quickly as her mom and said, "I'm savoring."

They all laughed.

"You made this?" Mary asked.

"I'm a pretty decent cook. I like to cook as a way to relax."

"It's amazing," Callie chimed in.

After the soup they each had a turkey sandwich.

"This was so good," Mary said while crying. "I can't thank you enough."

"I'm glad I can help."

"Mom," I would like to take a shower and then stay with you until some clothes come."

"Me, too."

"Mr. Ross, can you let us know when the clothes arrive?"

"First of all, please call me Ben and, of course, I'll let you know. I'll be in my office if you need anything. By the way, how about some pasta for dinner?"

"That sounds great," both women replied.

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"Take all the time you need. I have three large water heaters so feel free to soak in the tubs. When you see them, you'll know what I'm talking about. When the clothes arrive, I'll let you know. Again, if you need me I'll be in my office."

The bedrooms were the same in size, both with Queen size beds. In the bathrooms were sunk-in tubs and a separate large shower. All the toiletries you could ever imagine were in the vanities. The towels were plush and plentiful. The heat lamp made the room feel around 76 degrees. There was a plush bathrobe in each room.

While they each chose a bedroom, Callie was planning on sleeping with her mom. Callie stayed in the bedroom while Mary moved next door. Callie removed her filthy clothes and left them on the floor. Callie took her first bath in months, then moved to the shower where she washed her hair and snuggled into a heavy robe with a towel around her hair. She dried her hair with the towel and the hair dryer. She jumped on the bed, turned on the television and promptly fell asleep.

Mary filled the tub with hot water. Not enough to burn her, but hot enough to sooth her aching bones. Her knees, her elbows and her hands were red. Her feet were sore. She removed all her clothes and moved into the tub. She leaned her head back and closed her eyes. She thought to herself, "How did I ever get myself in the situation where we've been homeless for so many times throughout the past 13 years?"

She did not rush. She left some water out of the tub and added more hot water. She stayed soaking until her skin felt like a prune. Before she stepped into the shower, she looked at herself in the full-length mirror. She saw that her 36D tits were still firm. It had been so long since she shaved, her fire red bush was totally unruly as were the hair on her legs.