Bareback Risk

This story has several sex scenes, more than one is intense and graphic, but it also has a lot of story and character development. If you are looking for a "stroke story" come back and read this one at another time.

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"Okay Ana, but that means you won't get a good shift. I'll have to put you on nights, from eleven to seven."

"That's alright, Rick. I can't be too particular. I just need to earn some spending money for college; you know, for whatever my scholarship doesn't cover. That is, if I can get the scholarship to cover my final semesters. I'd do almost anything to avoid student loans."

"I'll try to put you on for the dinner hours anytime I need extra help," Rich explained. "That may give you a little more tips than what truckers and drunks pay. It's gonna mean you'd have to do that as extra hours. Can you work that many hours in one day?"

"Sure, four hours for dinner, plus my eight, with an hour or two off in between? Yeah, I can do that as long as it's not every day," Ana agreed. "I don't have any other demands on my time. Mom doesn't need me to help her."

"What?" Rick asked. "No boyfriend?"

When Ana shook her head, Rick smiled and asked, "Pretty girl like you and there's no boyfriend? What's wrong with guys these days?" Rick winked at Ana. It was only in jest when he asked, "Are you interested in an older man?"

Ana laughed, she had known Rick far too long to take him seriously. "Not in this town. The ladies of the Garden Club would run me out of town." She started to leave Rick's office and turned back to ask him, "If you lose a dinner waitress, can I have the earlier spot?"

Rick nodded, "Yeah, but don't hold your breath. Everyone who's on that shift has been here a long time."

"Yeah, I know, but it never hurts to ask." Ana waved and told the restaurant owner, "I'll be here early for someone to show me around. See ya later."

It wasn't the first time Ana had worked as a waitress. She was fortunate there was an opening at Town & Country Restaurant. However, it was the first time she would work as a waitress in her hometown. If she had stayed in the larger college town, she might have found a job as an intern with one of the larger companies she was hoping may hire her after college. However, her mother had convinced her to come home for the summer so she would be in town during the month before her brother's wedding, particularly because Ana was a bridesmaid. Her brother was engaged to marry the only child of one of the small town's leading citizens. With the parties and receptions leading up to the wedding, it will be one of the most important social events of the summer.

Ana was easy to get along with and worked well with the other employees at the restaurant. By the end of the third day, she could handle her shift by herself, partly because the large dining room was unused on weeknights. One dinner waitress worked half of the late shift on weekends. That left only the stools along the front counter, six booths, and the small semi-private dining room; complete with tablecloth and cloth napkins. The door to the smaller room was open after midnight, but few people chose to use the room during Ana's shift.

The cook for the night shift, an older woman Ana had known most of her life, was easy to work with. Betty Dennis would give Ana a ride to or from work if her mom couldn't take her across town. The older woman lived two blocks from Ana and preferred the night shift because her husband was disabled. It was easier for her to help him during the day and still get enough sleep.

Other than an occasional truck driver, most of the customers Ana served were regulars, few of whom wanted a menu. Betty could almost start cooking their burger, chicken fried steak, or bacon and eggs, when she saw them walk in the door. A few of them even called out their order before they found a stool at the counter or slid into one of the cushioned booths, calling Betty by name and saying how they wanted their eggs done.

To reach the small semi-private dining room, a customer walked in the front door and turned to the right. If the counter was busy and the booths were full, a customer might be in the dining room for a short time before a waitress thought to look in the small room with five widely spaced tables. The room was used for small meetings or special dinners for a large family and had extra tables folded against one wall to accommodate up to fifty diners in close quarters, such as a local club would use for their regular meetings. When Rick gave Ana a walk through the restaurant, he told her about the light switch inside the door.

Most of the customers who used the small dining room turned the light on when they walked inside. These were business people who wanted a private meal where their fellow citizens would not interrupt them. People who desired to have a meal and a conversation that would not be overheard, sought out the room, as did a gentleman seeking a quiet place for a romantic dinner. One or two waitresses worked the meal for larger gatherings or club meetings.

It was a rare occasion when the semi-private dining room had a customer during the late shift. Ana was surprised to look up and see the room lit by soft lighting, around the top edge of the walls. It was almost one o'clock in the morning, on a slow night. In fact, the booths were empty and there were only two men at the counter, both of whom had just finished their meal and were paying their tickets when Ana saw the lights on.

Although it was no longer common to provide a glass of water, people in the small dining room received a little better service that a casual diner could expect. When Ana walked by the open door she saw one man, probably in his mid-to-late thirties, sitting with his back to the interior wall. He was wearing dress slacks and a stiffly starched dark green shirt that stretched across his broad shoulders. She placed a glass of ice and water on the table in front of him and offered him a menu.

Without taking the menu, the man asked, "Did Webb and Eli leave?"

Ana knew, or had already learned the names of the regulars and knew the men to whom he referred were the two who were just then driving out of the parking lot. In her quiet voice, Ana answered, "Yes sir. What would you like to drink?"

Waving off her second offer of a menu, the man replied, "Tell Betty to fix Reece a steak and bring you and me a cup of coffee."

"I beg your pardon?"

"You don't have any customers and I don't like to eat alone. If you don't actually hate me already, maybe you'll sit with me a few minutes and smile occasionally so I can have a little company. Can you do that darlin'?"

It didn't really seem too unusual, what he was asking her to do. After all, this time of the evening saw few people coming in to the restaurant. It was just easier to remain open the two or three hours between the very late and the very early eaters. Shutting down the kitchen was a lot more work and expense than paying a cook to be in the kitchen during those few slack hours. Betty had an old chair and a footstool in one corner and often had a light snooze at that time of the night. On preceding nights, Ana had fixed at least one quick burger and a simple bacon, egg, and toast meal for single diners after telling Betty to keep her feet up for a little longer.

However, Ana was startled to return to the dining room and see the tall man holding her chair for her as she placed their filled cups with saucers on the table.

After seeing Ana seated and resuming his seat, the imposing man took a sip of his coffee, "You make good coffee, Ana."

With her cup halfway to her mouth, Ana looked at the man, startled that he knew her name.

"It is Ana isn't it? One 'n' in the middle Ana?"

"Yes, sir. I'm sorry, I don't believe I know who you are," Ana replied, replacing her cup in the saucer and searching her memory. The town was small enough for her to know, at least by name, if not by sight, most of the restaurant's customers and more than three-fourths of anyone she might see in town on any given day.

"I don't suppose there's any particular reason you should know who I am. But I know you. By the way, I'm Reece Winters." He looked at her for a moment before continuing, "Let's see, Ana Lancer, Class Valedictorian four years ago. Your grade point average beat Lloyd Bishop by point oh one and you managed to beat Hiram Langelier's little darling daughter, Susan, by point oh three points. Pretty big risk you took asking your teachers for extra credit assignments." He paused a moment to make sure he had her attention. "I wonder how big a risk taker you really are?" His words were a reminder of Ana's last two years in high school and the final question was a challenge, if she had ever heard one.

"I'm sorry, Mister Winters, I don't know what you're asking."

Reece Winters leaned against the back of his chair, cocked his head to one side, and looked at Ana through dark smoky gray eyes, "Mister Winters is my grandfather. You will call me Reece." It did not sound like a request, but more of a command. Ana didn't need any more information. The Winters's family was big, big men, big business, big money, and big reputations. The oldest, Mister Howard Winters, a notorious womanizer, was a widower of many years. The middle Winters' man, Richland, also single, was often thought to challenge his father's womanizing reputation. Following a spectacular divorce when the man accused his second wife of adultery and won, she left town with a very small, almost insulting, divorce settlement. Ana did not know the marital status of this Reece Winters, not that it seemed to matter, but he was not wearing a wedding ring.

The family was the largest landowner in the whole county. Every business endeavor they touched turned to money, lots of money. The men in the family were members of the bank's board of directors, the school board, any board, every board, and any political office they sought to run for, others need not apply.

A very slow smile spread across Reece's face as he announced, "And I guess you can figure it out pretty easily if I tell you I'll make the decision on whether the scholarship for your final semesters of college is approved."

Ana may have felt the blood drain from her face, but she prided herself that she did not blink. Instead, she stared at the man, waiting for the other shoe to drop, or the rest of her world to implode.

Ana Lancer lived all of her life knowing she wanted to be an architect, a residential architect. She knew what subjects she had to excel in, what courses she needed to take in college, and how long it would take her to get through school. There was never any doubt that she could do it, but getting it done in just five years meant she needed a good scholarship. However, the combined city service organizations only provided a four-year scholarship to the graduating student with the highest grade point average. Because of her stated goal, a loosely worded clause in the scholarship agreement mentioned she could apply for, and would likely receive approval of the additional money for semesters she would need, if her grades wereacceptable. This meant Ana could only have a very limited number of hours of outside work if she was going to leave time for studies and keep up her grades. She also wanted the best job offer available after she graduated and second best did not enter the picture.

However, Ana also knew her looks were against her. People think pretty girls get by on their looks, so she purposely downplayed her looks. Her dark blond hair was straight, in a blunt cut barely touching her earlobes. She favored minimal make-up, little more than lipstick and often forgot that, too. She did not dress fashionably and she usually wore socks with her sensible shoes. Apart from the fact that she couldn't afford to do so, plain neutral-colored clothing, meaning a mid-calf skirt and loose fitting shirt, lent itself to the image she wanted to portray and did not show off her figure. Glasses hid her dark brown eyes, rather than contact lens, because glasses hid some of her expressions. She wore large frame glasses for reading, not to see, but often included them as part of her everyday activities, giving herself a shield.

To add to her unfashionable looks, Ana kept her nails cut short and carried a large backpack filled with her schoolwork. She did not have or use a cell phone, did not have a car at school, and she made every effort to appear as a dowdy, frumpy, old-fashioned girl. Her appearance did not interest boys or men who preferred looking at a female with an hourglass figure, large breasts, a bubble butt, or swinging hips. Her methods worked. Ana could be in a room of fewer than ten people and none of them would recall that she had been there. She was at the top of almost every class she took and professors found her a joy to teach. Everyone else ignored or disregarded her and she did not care.

On the dash of Reece's pickup was the photograph he had removed from the file the president of the bank, Hiram Langelier, had given him to review and sign, for the approval of Ana's request for an extension of her scholarship. The photo showed the young woman, at the outdoor ceremony, where she had been presented with the award for her drawings. The photograph showed a light breeze was blowing her long red skirt, with pencil pleats, causing the material to cling to her figure, revealing what appeared to be long elegant legs. Although she was not wearing a belt to secure her long sleeve blouse to her waist, likewise the breeze caused the soft fabric to cling to her shapely breasts and slender waist.

Instead of responding to the man's threat, Ana turned her attention to retrieving his dinner. She paused a moment as soon as she could get out of the small dining room, resting with her forehead on the wall, trying to get her hands to stop shaking and get her breathing under control. She dared not do anything to disappoint the man who would say yea or nay to the approval of her request for the funds for her final year of school. A minute later, she was placing a platter of food in front of Reece, refilling his coffee cup, and asking him how he wanted his baked potato dressed.

"Just butter," Reece announced and dropped his arm down beside his chair. As Ana scooped butter out of the condiment holder, Reece brought his hand up under her long skirt, between her legs, sliding slowly up her inner thigh. His hand stopped a mere inch from her panties and he extended his thumb lightly brushing it back and forth, softly scraping across the crotch of her underwear.

Ana took a deep breath and held it as long as she could, afraid she would drop the condiment holder in his lap. She took a step back and to the side, and pushed her skirt down to cover her legs. Accustomed to an occasional customer taking liberties to touch her as she bent over their table, she said a quiet, "Please, sir."

Reece's deep voice commanded, "Don't wear panties tomorrow night."

Thankfully, three men came into the restaurant to order their very early breakfasts, giving Ana a chance to escape. Her breathing was hard and her head was whirling at the risk she took in allowing Reece Winters to think she was available for his use. She stayed busy serving the new customers and doing the other chores necessary to complete her shift work before the breakfast rush. Although she checked on Reece Winters, he merely nodded or shook his head when she stood well back from his table to ask if he wanted more coffee or needed anything to finish his meal. She must have been taking an order when he left the restaurant because she did not see him walk out. When Ana went to clear his table, she found a twenty-dollar bill for his meal on top of his ticket for almost fifteen dollars. There was also a fifty-dollar bill under his dinner plate. At least he tipped well.

** ** ** **

A few hours later, about an hour before Ana's shift ended, Reece came into the restaurant, for the second time, and walked straight into the small dining room. Two other men quickly followed him, all of them sitting at one table. All three men were wearing expensive suits, white shirts, and conservative ties, appearing as if they had just stepped out of a men's clothing catalog. Reece looked enough like both men for them to be his father and grandfather.

Ana heard a muffled groan from a man at the counter in front of her but couldn't decide who had spoken. "Oh shit! Big doin's boys. Three bad ass Winters and I don't mean snow."

While another waitress was walking in the front door to put her things away and prepare to help with the early morning breakfast orders, Ana went to the small dining room, carrying menus, three glasses of water, cups, saucers, and a full pot of coffee. As if he had not been in earlier, Reece Winters did little more than give his breakfast order to Ana. He gave the remainder of his attention to the two other men at the table. Half an hour later, the president of the local bank, her brother's future father-in-law, joined the three Winters men. Hiram Langelier did not order breakfast. Instead, Ana served him a cup of coffee, refilled the other three men's cups, and cleared their breakfast dishes.

Ana's shift was over before the meeting between the Winters men and their banker ended. Her relief said she would take care of cleaning the small dining room so Ana could get off her feet and rest. Waiting for Betty, Ana was sitting on the low loading dock at the end of the restaurant. She was leaning against the building with her feet stretched out in front of her when the older two Winters men and their banker walked out of the building. Grandfather and father Winters left in a big luxury vehicle, followed moments later, by the banker in a similar vehicle.

Reece Winters walked out of the restaurant as the other two vehicles drove away. He walked straight to Ana and smiled. He braced his hand on the side of the building, relaxed, as if he had all the time in the world and took his time to examine her, looking from the top of her head, across her face, and down the front of her shirt. Her apron, tied around her waist, accentuated her full breasts and small waist. He looked all the way down her legs, covered almost to her ankles by her long skirt, ending at the sensible shoes and socks.

"Well, well, Miss Prim-and-Proper Ana Lancer, finished another hard shift on your feet, huh?"

"Yes sir." She dared not say anything else. She had no desire to antagonize this man or give him any reason to dislike her. He controlled the money she needed to finish school.

"Why are you working? Shouldn't you be having fun this summer?"

"No sir, whatever I earn during the summer pays my personal expenses while I'm in school."

"Ah..." he nodded his understanding. "The scholarship doesn't cover incidentals?" Reece may not have examined the whole file as closely as he could have or he would have known the answer to his question. However, he also enjoyed teasing Ana, she was so careful about the way she talked to him.

"Yes sir." She looked up, but no higher than his chin, she did not need the distraction of the way he looked at her.

"Maybe we need to have a discussion about some kind of allowance to help you with expenses?"

"I would appreciate that, sir. I'm careful, but..." Ana shrugged her shoulders, not caring to give him any more information than necessary.

Reece took a step forward, his knees mere inches from her thighs. He then held out a cellular telephone. Before she could do much more than look at the phone, and then back up at Reece, he slipped it in one pocket of her waitress apron.

He said; as if it was the continuation of a conversation they had several minutes ago, "I'll call, you answer."

Ana was on her feet, shaking with fear and not caring about the words she used. "What? You'll call me and I'm supposed to do whatever you say."