The stagecoach came to a bumpy stop in front of the Wells Fargo and Co. Express building in Columbia, California. Winnifred, or Winnie as she was known to her friends, looked out at the brickwork building and sighed.
For the last seven months she had been tossed around on a ship, as well as fucked by the ship's captain, until she landed in San Francisco. The faded green dress she was wearing was the only dress that survived the long ordeal. Her only other dress had become damaged beyond repair during the extensive ocean voyage and had been used to keep her current dress intact.
Her long journey was far from over as she was soon on a long, bumpy two-day trip via stagecoach though the hills and mountains of the California territory. Many times she saw they were passing by active gold mines thanks to the recent gold rush. Hundreds of men flocked west to make their fortune in the quest for gold. Now she was staring at a brick building with what she assumed was Wells Fargo written on the walls. She bit her lower lip as the driver opened the door and helped her out.
"Welcome to Columbia, ma'am," he said with a gentle smile.
Winnie smiled back. "I'm really in Columbia?"
"Yes ma'am," he replied. "I'll get your bags down in just a moment."
Winnie watched the driver remove boxes and such including a large mail bag, a metal box, and her bag. A couple of men from the brick building rushed out and grabbed the metal box while a young boy took the mail bag. Winnie stepped over to her bag when the driver said, "Need some help with that ma'am?"
"Well, actually, I'm looking for the Fallon Hotel."
"I know it well," said the driver. "If you'd like, I can take you there myself."
Winnie smiled, "That would be wonderful!"
"Wait here, I'll be right back." The driver ran into the Wells Fargo building, then came back wearing a jacket and carrying a satchel.
"Sorry about that. I almost forgot to let my boss know I was leaving. He said he needs me to deliver this to Miss Lenore, the hotel manager."
"Miss Lenore is who I'm meeting," said Winnie.
"Ah, you're one of her girls," said the driver.
"Sorry ma'am," he said, "I meant no disrespect. Miss Lenore only hires the finest ladies."
Winnie sighed. "It's not your fault. This is my first real opportunity to make some real money since my husband died."
The pair began to walk down the dirt street as horses pulling buggies and men on horseback passed them along the way. "How did he die?"
"Consumption. It was shortly after we were wed. I had no money and before long I was kicked out of our home. I ended up living on the streets. It was there I met Miss Polly, a business associate of Miss Lenore's. She gave me a hot meal, a bath, and bought me this dress."
"I'm sorry to hear that. Oh, and I'm Andrew."
"Winnifred, but my friends call me Winnie."
Andrew smiled. "May I call you Winnie?"
Winnie shared that Miss Polly had taught her some about being a lady of the evening, and how she came from North Carolina to California. Andrew listened and occasionally pointed out the different buildings including the bank, the school house, the City Hotel, the firehouse, and much more. Everywhere new buildings were in different phases of construction thanks to the success of the gold mines that surrounded Columbia. Soon they approached a large, two-story brick building.
"Here we are," said Andrew.
Winnie sighed. She knew this was what this whole trip was about, her new profession as a prostitute. "Well, thank you Andrew."
"I'm not leaving you here," he said. "I want to make sure you get delivered to Miss Lenore. Trust me, it will be fine."
Winnie smiled. "Thank you again."
"I hope one day you can thank me properly."
It was the first time a man had made a suggestion to her that didn't sound like a mandate. "That would be very nice," she replied.
Andrew and Winnie entered the hotel lobby where they saw men and women sitting around talking. The women were wearing colorful dresses that barely covered their breasts and skirts that showed their legs and ankles. The men were drinking and laughing with the women. One couple stood up from a table and headed up the stairs. A tall, dark skinned man with short black hair and wearing an expensive suit stepped up and asked, "May I help you?"
Winne trembled at the sight of the man who towered over her. Even though he was wearing such a nice suit, starched white shirt, and tie, his presence was slightly intimidating. She tried to speak but no sound came out. Andrew, who was familiar with Thomas, quickly removed his hat, smiled proudly and said, "We're here to see Miss Lenore. I've got two packages for her."
Andrew pointed to the satchel and Winnie.
Thomas smiled a gleaming white smile and said, "Of course, wait here please."
Thomas walked away and Winnie whispered, "Who is that?"
"Thomas," replied Andrew in a low voice. "He works for Miss Lenore. I guess you could say he makes sure the girls are safe. Rumor has it he is a runaway slave. Others say she bought him. However, California is a free territory so he might be a free black man. Either way, no one here dares to cross him."
Thomas returned with an older woman with dark brown hair with wisps if gray in her bun wearing an elegant maroon gown that flowed as she walked. "Andrew! Good to see you again!" she exclaimed.
"And you as well Miss Lenore," said Andrew.
"And you must be Winnifred! Miss Polly wrote me all about you."
"Yes, ma'am," said Winnie, blushing slightly.
"I'm Miss Lenore and welcome to the Fallon Hotel. You've met Thomas, our doorman and head of security."
"Welcome ma'am," he said, his deep voice washing over Winnie like a warm blanket. Winnie had never had much contact with colored men, but with Thomas, she felt a sense of safety and security.
"Oh," interrupted Andrew, "Mr. Olsen asked me to give this to you," handing Miss Lenore the package inside the satchel.
Miss Lenore looked at the package a moment, then handed it to Thomas, "Would you take care of this for me so I can meet with Winnifred. And Andrew, feel free to enjoy the company of Elizabeth," Miss Lenore motioned to a young, dark haired woman. "On the house of course, for escorting our young Miss Winnifred."
Elizabeth stepped up and wrapped her arm around Andrew, smiling. "Looking for some company sir?"
"Why thank you Miss Lenore," said Andrew, nodding.
"Just keep your eye out for future girls like Winnifred," said Miss Lenore.
"Of course Miss Lenore," said Andrew.
"And Elizabeth, make sure our friend Andrew gets the House Special."
Elizabeth quickly smiled. "Of course Miss Lenore. It will be my pleasure."
Elizabeth escorted Andrew away as Miss Lenore turned to Winnie. "Now, let's you and I have a chat, shall we? Give Thomas your bag and follow me."
Thomas knelt down and grabbed her bag as Winnie began to follow Miss Lenore. Then she stopped and exclaimed, "Wait! I need something from my bag!"
"What's that child?" asked Miss Lenore.
"The letter from Miss Polly."
"Ah yes. Thomas, let her retrieve the item then take the bag to her room."
Winnie opened the bag, dove her hand inside, and removed a tattered envelope. Miss Lenore's face showed her disappointment in its condition. "Thank you, Thomas," said Winnie.
Thomas smiled, walked upstairs and disappeared. Winnie handed Miss Lenore the envelope with a nervous smile.
"Yes, follow me please," said Miss Lenore.
Miss Lenore led Winnie into what appeared to be an office area similar to the one Miss Polly had when they had met. Winnie sat in a chair and nervously fidgeted. Miss Lenore read the letter in silence, sighed, then asked, "Who else has read this letter?"
"Winnifred, let me explain something to you. I have worked hard to run a good business and the one thing I don't tolerate is liars. So, either tell me who all has read this letter or I'll have Thomas get your bag and you'll be living on the street. And trust me when I say I'm a woman of my word."
Winnie's eyes welled up with tears as she said, "Just the ship's captain, ma'am. He said the letter gave him permission to have me."
"Did he force you?"
"No, he said it was part of my job and repayment for my fare."
Miss Lenore sighed. "That bastard. You'll be the last girl he ships for me if I have anything to say about that. He lied to you. Here, read the letter for yourself."
Miss Lenore handed Winnie the letter, but Winnie just sobbed. "I can't."
"I can't read."
"Not yet you can't. I'll bet you can't write either."
"How old are you?"
"Nineteen," Winnie replied, wiping the tears from her cheeks. "I celebrated my birthday on the ship. Captain Roberts was extra nice to me that day. He had the ship's cook fix me a nice fish dinner and even a small cake that he fed to me."
"I'm sure he was," hissed Miss Lenore. "How is it you're not carrying child?"
"He'd spill his seed on my stomach or take my ass."
Miss Lenore sighted. "Let's establish some ground rules Winnifred–"
"Alright then, Winnie. From this point forward, you will only have sex with men when I tell you. There will be no more freebies. Some will try to say they paid for specific services, but if I didn't tell you directly, he didn't pay for it. Also, starting tomorrow, you'll be taking reading and writing lessons. I require all my girls to have some basic education. You'll have your own bedroom and share a workroom with two other girls."
"Workroom?" asked Winnie.
"It's where you'll take the men for sex. I have found that having a separate bedroom works better for all. It gives you a space that is all yours."
"Thank you ma'am."
"You'll be expected to share in the household chores including cooking. You can cook, can't you?"
"Good. Your momma taught you well."
"She did, ma'am."
"Now, you'll be given work clothes and outing clothes. Do not go out into town in your work clothes."
"Bad for business. Can you sing or play a musical instrument?"
"I used to sing in the church choir," said Winnie.
"Well, if you're any good I'll have you perform for the guests. But that's for another day. I'm sure you're tired. Just one last question. How many times did you and the captain engage in copulation?"
"How many times did he fuck you?"
"Oh, two to three times a week. Except the week I bled. Then he left me alone."
Miss Lenore quickly wrote something down, then sighed. "I'm sorry he did that to you. That wasn't my intent, nor was it Miss Polly's. He took advantage of you with a lie. Oh yes, I meant to tell you, you'll earn a percentage of your wages depending on what services you provide. Trust me, a pretty gal like you will easily make your voyage fees in a very short time."
Winnie smiled. "Miss Polly said it might take me a few months to a year."
"I doubt it will take more than six months. With the gold mines yielding such wealth, the men will have plenty of money to burn. I only wish Miss Polly had sent me two or three of you."
Winne was escorted upstairs where she bathed and retired to her room. She was unconscious before her head hit the pillow and thus was unbothered by the sounds of the other women and men conducting business in the nearby workrooms.
Over the next few weeks, Winnie quickly learned the rules of the hotel. She would take reading and writing lessons during the day, and cook and clean at night. The girls would teach her different techniques about sex and being with men. Winnie's singing voice was rather lovely and soon she was singing for the guests three nights a week.
Shortly after, Winnie started entertaining the men who came in for a drink or more. Some just wanted to talk. That cost ten dollars and two drinks. For sex, it started at fifteen dollars, depending on what the men wanted. Winnie earned a percentage of her fees that Miss Lenore charged, and quickly became one of Miss Lenore's more popular girls. Part of her popularity was her blonde hair and blue eyes, and part was her wiliness to either suck a man's cock or let him fuck her ass. Two skills she had learned and mastered thanks to the ship's captain.
One evening, Andrew came in with a new girl for Miss Lenore. Miss Lenore called Winnie over and instructed her to give Andrew the House Special, like she had with Elizabeth when Winnie first arrived. A House Special was anything the client wanted and Miss Lenore would cover the cost. It was Andrew's fee for watching out for the new girls coming in from San Francisco.
The couple shared a drink before slipping upstairs. "I see you're doing rather well," said Andrew as they entered her workroom.
"Miss Lenore has been very good to me," said Winnie, closing the door.
"I'm glad. I've thought about you often."
Winnie smiled. "I'm sure you say that to all the girls you bring here."
"No, no I don't. Really. I mean, yes, I brought Elizabeth, Victoria, you, and the new girl, Laura. But with you, there was something different. Tell me Winnie, how old were you when you were married?"
"Seventeen," she replied. "Edward was a good man."
"How long were you married before he died?"
"Just over a year. He was a share cropper. It's why when he died I was tossed out by the land owner. He didn't care. Had his wife not been there I'm sure he would have done to me what he wanted."
"So how did you end up here?"
"I was living on the streets, sleeping with random men for food, when Miss Polly found me. She cleaned me up, taught me to be a prostitute, and sent me here. She paid for the dress I was wearing the day we met."
"It was a pretty dress."
Winnie laughed. "That dress was rags."
"Your dresses are rather pretty now."
"Miss Lenore expects nothing less."
Andrew took Winnie into his arm and nuzzled her neck. "You smell very pretty."
"I hear you do things the other girls won't."
"Miss Lenore said for me to give you a House Special. What would you like?"
"Will you suck me?"
"Of course. Anything else?"
Andrew sighed. "Is it true you'll let a man take your other entrance?"
Andrew bit his lip. "That too, please."
Winnie helped Andrew remove his pants. His cock was already hard and pointing at her. The purple mushroom head pushed through the foreskin and the curly, brown hair seemed to glisten with sweat. Winnie removed her dress, standing before him in her corset, stockings, and knickers.
"Will you take all that off?" asked Andrew.
Winnie quickly stripped down, happy to be free of her corset and knickers, allowing her breasts to hang free. Andrew admired the two pale globes with the dark pink areoles and small, hard nipples begging for his lips to suck them. Before he could even move to touch her though, Winnie knelt down and took Andrew's cock into her mouth. The thick member filled her mouth perfectly as she pushed his foreskin back and the sweet, salty taste of his precum coated her tongue. Andrew moaned. In all of his years, he had never had any woman do this for him. It was always touch and fuck.
He watched Winnie's blonde hair bounce as her head bobbed back and forth on his cock. He ran his fingers though her hair as he savored the sensation of her lips and tongue touching him in such an intimate way. Andrew debated about shooting his seed in her mouth, but decided he wanted more. He pulled Winnie back and said, "May I do that to you?"
"Please," said Winnie, smiling.
Winnie quickly lay on the bed, spread her legs. Andrew knew the girls trimmed the hair there, and it made it easier for him to see her pussy glistening with her juices. Andrew breathed in her musky aroma. "You have the best smell of all the girls," he said.
"Thanks," gasped Winnie as she felt Andrew's lips latch on to her pussy.
Andrew used his tongue as he licked her labia and sucked her clit, savoring her sweet juices and pushing her legs further apart. He knew most of the girls enjoyed this, but rarely returned the favor. Winnie's pussy was his new favorite. He slid his tongue inside her, making her purr softly and squirm. A wicked idea entered his mind. He slid two fingers inside her pussy and Winnie squealed as her pussy clamped down and his face was suddenly coated with her sweet juices.
"Damn Winnie!" he exclaimed. "That was amazing!"
Winnie giggled. "Thank you."
"So, how do we do this next part?"
"I'll get on my hands and knees, like this," explained Winnie, as she quickly moves to her hands and knees, facing the foot of the bed. "You'll need to go slow at first. Maybe stick your cock in my pussy first to get it good and wet. That always helps."
Andrew smacked Winne's ass hard. "Such a filthy mouth you have."
Winnie jumped and moaned. "You weren't saying that when your cock was there."
A second blow befell Winnie's ass, creating a redness on her cheeks. Both were glowing red now as Winnie shook her ass and said, "That's it, Andrew! Give it to me!"
Andrew grabbed her hips and slammed his cock into her pussy. Winnie inhaled sharply as her eyes rolled back into her head. Andrew's cock filled her the way no man before him ever could. After a few pumps he pulled out and gently pressed the head of his cock to her rosebud.
"Like this?" he asked.
"Yes," moaned Winnie. "Now, push gently, but don't go too deep to start. Give me time to adjust to you. You're bigger than most."
Andrew smiled. Though he suspected she was just saying what she did to make him feel good, he didn't object. He pressed until his manhood just entered her anal cavity. The tightness was a feeling he'd never experienced before.
Winnie gasped and panted. She knew his cock would be a tight fit, but she also sensed he'd be gentle. After some time and gentle squeezing of her ass around the intruder, she said, "Okay, now slowly thrust forward, going deeper with each push of your cock until you are all the way in."
Per her instructions, Andrew began to pump, pushing a bit deeper until he was fully in her ass. "Now fuck me!" cried Winnie.
Andrew began to thrust faster, fucking her ass the way he hoped to one day fuck her pussy. It wasn't long before he was pounding her ass. His balls slapped her pussy. The bed beneath them squeaked, the headboard slammed against the wall, their moans echoed within the room, and the aroma of raw sex filled the air.
Andrew reached down and grabbed a handful of her blonde hair, pulling her head back. In front of them was the dresser with a large mirror. They smiled at each other as they watched their reflection. With each thrust, Winnie's breasts swung, the bed squeaked and shook, and the pair panted and moaned. The sight of seeing themselves fuck fueled their desire and pushed Andrew over the edge.
"I... I..." stammered Andrew.
"Yes!" screamed Winnie. "Fill my ass!"
Andrew's cock pulsed as his spunk filled Winnie's ass, empting his seed within her anal cavity. Winnie's pussy soaked his balls with her juices. The orgasm for each was mind-blowing and incredible. Once his cock was soft, Andrew withdrew from her ass and the couple fell onto the bed. Andrew wrapped his arms around Winnie, spooning her in the bed.
"Winnie... that was... wow!"
"I... agree," she gasped.
Andrew nuzzled her neck, kissing the back of her earlobe. "Next time, I want you to be on top."
Winnie smiled. "You want me again?"
"I don't want anyone else."
Winnie knew he was talking in the moment, but she didn't care. Even her late husband never spoke to her in this way. She just closed her eyes and pretended for the moment she wasn't a prostitute and he wasn't her client. In that moment, he was her husband and they had made love.
The pair cuddled until the sounds of another couple reminded them both their time was up. The pair quickly dressed, Winnie checked her hair, and then the pair returned to the downstairs where Winnie performed for the crowd.
Winnie worked for Miss Lenore for several years until the gold mine dried up and the need for prostitutes dwindled. Andrew kept his word and only enjoyed Winnie's company, despite the offers of Miss Lenore and the other girls. Miss Lenore decided to sell the Fallon Hotel and Theater, and offered it to Andrew and Winnie. It was no secret to anyone that the pair were madly in love. With her earnings from working for Miss Lenore, and some savings Andrew had, they bought the hotel and were married with the old staff present. Miss Lenore even paid for the wedding and reception. Together, Andrew and Winnie ran the hotel without the brothel element, bringing in local talent and other entertainers.
Though the gold mines had dried up, the town, unlike so many others, survived thanks in part to the copper mines discovered in the neighboring town of Copperopolis.
Over the years, Winnie gave birth to four beautiful children while helping Andrew run the hotel. The couple enjoyed a long happy live and a passionate sex life, always thinking back on how fate brought them together.
Jun 23, 2018 in anal