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Training on the Trail

"A Modern woman finds fulfillment in an old fashioned relationship"

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2.1k words 2.1k words

Author's Notes

"Trigger Warnings:  graphic descriptions of elements of BDSM which include but are not limited to TPE, female submissive, nudity, domestic discipline, spanking, and nipple play."

He is quite wealthy, but that is not why Lisa loves him. He is elegant, but that is not it either. He is beautiful, but that does not matter. What matters? His love and care for her. His interest in every detail of her life. His intelligence. His firmness. His kindness.

He is the owner and CEO of a private rail car company, catering to the old money. They, therefore, travel by train. He has told her that he wishes her to accompany him on all of his trips - both business and pleasure. When they are at the office, Lisa Miller is a very professional, highly respected historian for Surrey Train Corp. When they are on the train, however, Lisa belongs to him. Totally.

His private car is decorated beautifully, in a lovely 1950's style but with all modern conveniences carefully concealed. He has overseen everything, carefully choosing the furniture, the art, the linens, and even my clothing. In keeping with the style, Lisa dresses in a vintage manner when entertaining his clients. Demure, sweet, and always modest.

However, in their private car, she will not dress at all unless specifically instructed to do so. Sometimes, he will wish her to wear heels, sometimes a corset, sometimes only pearls. Mostly, though, he prefers her to be nude. He will use her body as he will. She is his humble and loving servant, and he her loving and dominant master. Lisa, a self-assured woman with a Ph.D. in history, eagerly and willingly agreed to all of this, but now she must prove to him that she truly wants this lifestyle forever. After all, actions speak louder than words. 

********

 Their relationship came about in an unusual manner. Or perhaps not. Perhaps it was destiny. Lisa was driving to work one day when her car broke down. This shouldn’t have been a surprise since she bought the thing already used eight years ago when she began working on her Graduate degree in History.

The old jalopy had well outlived its life expectancy, but she didn’t have the funds to replace it yet. She hated the idea of going into more debt, but she was beginning to think that would be the only answer. Only one more year and she’d have her student loans paid off. Maybe this old clunker could make it that long. Sadly, she knew next to nothing about cars, so she did the international “car distress” symbol of raising the hood.

She called the office to let her secretary know she’d be late getting in. She may drive an unreliable car, but Lisa refused to be unreliable herself. Next, she called a tow truck and was informed that it would be two hours before they could send someone out to help.

Wiping the sweat from her brow and hoping that her deodorant would hold out, her mouth dropped open when a  beautiful silver Lexus pulled up and the most stunning man she’d ever seen walked out. He was wearing aviator glasses, so she couldn’t see his eyes, but he was at least 6 feet tall with short dark hair shot through with strands of silver. He was dressed in a dark suit, blue shirt, and blue and yellow tie. He looked familiar, but Lisa couldn’t place him.

“Can I help you ma’am?” he said as he held out his hand. “I’m Braden Surrey of Surrey Train Corporation.”

That was why he looked familiar. “We’ve actually met, sir. I’m Lisa Miller. You hired me five months ago as head historian for your company.”

He dropped his hand, raised his sunglasses, and grinned.

“Well, I’ll be damned. It is you! I’m sorry I didn’t recognize you right away. That was rather rude of me,” he stated, his voice now friendly rather than simply solicitous.

“No problem, sir. You couldn’t have been expecting to see me here. Besides, I probably didn’t look quite so frazzled the last time we met,” she joked awkwardly.

“Probably not. Still, no need to be frazzled. We’re obviously going to the same place. Why don’t you hop into my car and I’ll send a company tow out to take care of your car.” He held up his hand when she opened her mouth to reply. “Don’t argue with your boss. If you’re worried about your car you won’t be giving your full attention to the job. Just good business policy.”

Lisa smiled nervously but agreed.

 Over the next few weeks, Mr. Surrey found multiple opportunities to drop by Lisa’s office. Eventually, he asked her out on a date, assuring her that her job did not depend on her answer.

“To be honest, you’re the best historian this company has ever had. Your work is impeccable. I don’t want to jeopardize that. If going out with me makes you the least uncomfortable, tell me. I can take no for an answer,” he assured her.

“Let me think about it. I’ll let you know tomorrow?” she’d answered.

“Of course.”

Lisa, being an historian, knew how to do research. She discovered that Braden Surrey had been married before but his wife of twenty years had died in a horrible motorcycle accident. They had consciously decided never to have children. The company would, therefore, pass on to his niece when he retired or be sold.

There had never been a sexual harassment claim against the company in its 150-year history. Mr. Surrey and his wife had a monogamous and happy marriage with no known scandal. According to friends, he was devastated when she died of cancer and has not dated in the six years since. On the professional front, Mr. Surrey was known to be an honest and astute businessman, something Lisa had discovered before she applied for her current position. After careful consideration, she accepted Mr. Surrey’s proposal for a date.

One date led to another and then another. True to his word, though, their personal relationship had not affected her job in any way. Over time, Lisa discovered that Braden enjoyed jazz music, Art Deco designs, safe cars, and insisted on traveling by train whenever possible. He was also a foodie and loved 1940s and 50s movies. He was also, by nature, a dominant, something which both excited and intrigued Lisa.

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It had taken a long time for Lisa to come to terms with the fact that she was a natural submissive. Every relationship she had ended with disappointment primarily because the men she dated, even though they were all kind, intelligent, and well-meaning people, had not been willing to set boundaries for her. At the age of 35, however, Lisa knew who she was and what she wanted from a man. She wanted to be able to count on her partner to love and respect her and to take up the reins of guiding both her and their relationship. Yes, she was a professional woman who was in control of her own life, but she wanted something else from her personal life. On their fifth date, she discovered that Braden wanted something very similar.

“Look, my wife and I were perfectly suited. I’m not looking for someone to take her place, no one could do that. I’m also not a one-night-stand kind of man. So, if we are going to continue, and I’m hoping we will, I need to come clean with you. What do you know about domestic discipline?” he’d asked hesitantly.

Lisa leaned over their table at Gillian’s and answered, “Quite a bit, Sir.”

 

********

 

This trip would be a short one - only three days. It would also be a trial run to see if this new lifestyle truly suits them both. Lisa walked into the car and marveled at its beauty. She knew the layout of the car since she had catalogued the blueprint for it, but seeing it in person was simply magical. She turned and smiled at him. He crossed his arms and gave her a pointed look. A hot blush crept up her face. Lisa’s first act was to remove her clothing, but already she had made a mistake. Still, that may not have been a bad thing, since now she would be able to know if Braden was serious about the guidelines they had both agreed to.

Lisa looked down and murmured, “I’m so sorry, sir” and rushed into the bedroom, removing her dress, bra, panties, stockings, and shoes. She neatly folded them and put them away just as he had instructed. All clothing was to be out of the way - out of sight.

She walked back into the parlor and stood before him. He smiled at her, lifted her chin and kissed her, running his hands up and down her sides, back, and arms. He deepened the kiss and grasped her small, pink nipples. Then he squeezed. She gave a little yelp and started to pull away but stopped herself. She heard a deep rumble in his throat and knew he had not missed this tiny lapse. Judging by the half grin on his lips and his shining eyes, though, Braden was obviously pleased that she corrected herself.

He squeezes harder and she whimpered, but felt her will begin to bend to his. Evidence of this began to drip out of her body and formed a sheen of honey that coated her labia and thighs. Lisa began to tremble as he slowly pulled his mouth away. Keeping hold of her tender and now rock-hard nipples, he led her to the dining table. Once there, he released her nips but she remained under his control.

“Legs as far apart as you can. Bend over and grasp the other side of the table. Maintain this position,” he ordered. “We agreed that you would immediately go to the bedroom and remove your clothing upon entering the train, but you forgot didn’t you?”

“I did, sir. I apologize.”

“Are you ready for your first correction?”

“I am,” Lisa stated calmly.

She took a deep breath and steadied herself. She was more than ready for this correction. They had negotiated for hours before deciding upon this trial trip, eventually agreeing upon conduct, expectations, corrections, decorum, hard limits, and a safe word. Now, it was time to see if this lifestyle would suit them both. Lisa felt the chug-chug movement as the train carried them over the rails, and adjusted her stance to be sure she was stable.

The first sharp strike of the leather slapper drew out a surprised cry from her. She grasped the edge of the table tighter and bit her lip.  Four slaps in total- two on each cheek - had her gasping. Nonetheless, Lisa had never felt so excited in her life. When Braden placed a strong but soft hand on her back and said, “Released” Lisa instinctively turned, dropped to the floor, and hugged his legs, thanking him for his correction.

“Thank you, sir,” she murmured.

He placed a hand on her head and said, “Look at me, Lisa. Tell me exactly what you are thanking me for.”

She looked up at him with watery eyes. She smiled and answered, “For holding me to our agreement. For accepting me for who I am. For knowing what I need to feel safe and loved.”

Braden bent down and helped her stand. He gathered her in his arms and kissed the top of her head.

“My love, this is just the beginning.”

********

 

Three days later, he held out his hand and helped her down the steps of the railcar. He helped her, not only because he was a gentleman, but because she could barely walk on her own. Her bottom was red and slightly welted, her thigh muscles strained and shaky, her pussy swollen and tender, and her anus still filled with a rather large plug. Lisa wobbled a bit on her three-inch black pumps, and he steadied her.

“So,” he asked once they were in his Lexus, “do you think this lifestyle is for you?”

Lisa looked at his handsome profile, noting the tension in his jaw. She realized he was anxiously awaiting her answer. Who would have thought that a man used to giving orders would be nervous?

She giggled, pure joy bubbling from her heart, and said, “Sir, I think you’ve ruined me for any other way of life.”

Published 
Written by Anarie
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