Training Tiffany
Chapter 1

Caution: This Romantic Sex Story contains strong sexual content, including Ma/ft, Consensual, Heterosexual, MaleDom, Spanking, First, Slow,

Desc: Romantic Sex Story: Chapter 1 - A wealthy man with a taste for classic cars, gives a troubled teenager on probation work experience on his estate. When she takes one of his classic cars for a joy-ride, he doesn't react as you might expect. Just a two-part tale with some mild D & S.

My name is Peter Weston. I'm a wealthy man. Some would say 'rich', others 'comfortable', yet others 'filthy rich'. It's not my fault, I inherited it. But I didn't – and don't – think it makes me better than anyone else. Wealth is a responsibility. Wealth means that, with care, one can transform lives, towns, districts, even countries, by careful investment. When you have as much money as I have, the occasional loss doesn't really matter. Even without interest, it would be difficult for me to spend all the money before I die. With income, it's a forlorn hope. I think ... I hope ... that I have done some good. But this isn't about my philanthropy.

I don't see why I shouldn't enjoy the finer things in life. I have a nice yacht, and I am competent to sail her. I own a light aircraft, and I am working on the various qualifications there, too. I have motorbikes, classic ones, which are carefully maintained and I ride them. No point in having it if you don't use it.

And I have cars. I like cars. All sizes and types, stored with the bikes, in a climate-controlled garage that was once a coach house belonging to the mansion which is my principal residence. And that ... is where the story begins.

One of my ... I suppose you'd say 'Charitable Involvements' ... was taking in, from time to time, troubled youngsters who would otherwise be in some sort of juvenile detention. It was no strain financially and mostly my staff kept an eye on them. They helped the groundsman, housekeeper and the full-time mechanic who kept my toys on the top line.

Tiffany was one of them. Just over average height, straight brown hair, thin to the point of emaciation from her life on the streets ... and fascinated with fast cars. To be sure, she did her share in the house and garden – the staff made sure of that – but the rest of her time was spent tinkering (under strict supervision), valeting or wax polishing my cars and bikes.

She was due to leave, to go back into the system, and I was intending to give her a good report, I was going to suggest she be put into a mechanic's apprenticeship or something similar – and fund it if necessary. She'd been quiet and in all honesty I'd hardly noticed her, so my good opinion was based on reports from Bert in the garage, Hannah the housekeeper and Jimmy the gardener. (Apparently, her main involvement in the grounds was driving the ride-on mower, which was really a small tractor. Jimmy said she was expert.)

So it was quite by accident that I was just getting out of my Ferrari when I heard the unmistakable sound of my irreplaceable D type Jag starting. I didn't think anything of it at first – motors have to be run from time to time and Bert was insured to drive all the vehicles, of necessity. I watched through the, still open, door and saw the Jag, exhaust burbling with that gorgeous rumble, roll past.

Except it wasn't Bert at the wheel, it was Tiffany. Okay, she was overstepping the mark, but as long as she kept it in the grounds, I wasn't about to go ballistic. I did get back in the Ferrari, started up and rolled it back out. That was when I saw the back end of the Jag as it disappeared through the main gate.

I didn't think, I just reacted. There aren't many D-types still in existence, still fewer are road-legal, and mine was probably irreplaceable. I set off in pursuit. I'm sure it would have been better to call the police – the Jag had a sophisticated tracker on board – and just maybe I'd have got it back undamaged. As it was, though, I went for a drive.

The first obstacle was the gate, which opens automatically ... and slowly ... and had closed after Tiffany, so she was well ahead by the time I got out and on the road. We're not far from the motorway and she'd headed for it, so I followed and as soon as I was able to relax a little, called Bert. Aren't voice-activated Bluetooth sets wonderful?

Traffic, even on the M1, was light and she wasn't pushing things, so I held back. I don't know if she knew I was there before, but clearly realised it as I followed her onto the exit slip for North Muskham. She sped up. Seventy on the motorway – legally – is one thing. Seventy plus on the two-lane single-carriageway country road that is the A616, is quite another. For one thing, the speed limit is sixty.

I had no trouble keeping her in sight and we made it through Kneesall without incident, but the roads get narrower after that, with some sharp corners. I was okay in the Ferrari, but the Jag is a lot of car and she pushed a little too hard on a very sharp right-hand bend and lost it, the nearside of the car wrapped around a substantial oak tree. Ouch. That was going to be expensive.

Bert had been onto the Police and I updated him as I pulled onto the verge and got out. Tiffany was still sitting in the driver's seat when I got there. She looked up at me; she was trembling, but there was a defiant look on her face.

"Don't move," I said quietly. "Any pain?"

She shook her head. "No."

Well, that answered one question. When I said 'don't move', I was thinking of spinal injury, but it seemed her neck was okay, at least.

"Well, wait until a paramedic gets here to check you out, anyway. But, oh dear, I think the term is you've 'really screwed the pooch', Tiffany." Her lips tightened into a thin line. "I was going to recommend you be found an automotive apprenticeship. I was all set to give you a glowing testimonial. What the hell did you think you were doing?"

"Sorry." It was sullen, dull, and she stared straight ahead through the tiny windscreen.

"Sorry? A quarter of a million pounds worth of damage to an irreplaceable car and all you can say is 'sorry'?"

She turned her head to face me and I saw twin tracks of tears coursing down her cheeks.

"Okay," I said more gently, "you are sorry. But you have to face up to the consequences of your actions."

As I was speaking, a paramedic first response car drew up behind the Ferrari, followed shortly after by a Police patrol car.

The paramedic thought she'd come through undamaged, but wanted her to be checked out by A. & E. One of the Police went with her and her partner took my statement.

"You'll be pressing charges?"

"Probably," I said, but had been chewing the situation over. "I want to talk to her Probation Officer first. There may be a better ... more productive ... way. She was doing so well until this morning."

It was evening before Jonathan Sparrow, her Probation Officer ... who I knew and respected ... turned up with Tiffany in tow. She was subdued ... resigned, I suppose.

"Go and find Hannah," I said to her, "while I have a word with Jonathan here."

Her eyebrows rose, almost in unison with Jonathan's, and she left us in my office.

"She was doing so well," I said, and he nodded in agreement.

"I hate it when this sort of thing happens," he said, then smiling, went on, "not that I often have one of my clients steal a classic super-car!"

"I don't suppose so," I smiled back. "Jon, I don't think putting her back in the justice system is the way to go. The car's insured, but we'd be writing Tiffany off." He nodded. "So, I'm going to propose she work off the debt."

I'd managed to shock him to the core. "What are you suggesting?"

"If we can swing it, we work out a plan where she earns the cost of repairing the Jag, and earns her board and lodging, along with eventually gaining qualifications as a mechanic. At minimum wage, we'd be looking at a very long indenture, maybe twelve years, but at the end she could have a new life. If the Courts will go along with it, I'd be willing to give it a try. If she screws up again, she can go back into the system."

"Okay," he said slowly, "I'm willing to give it a try. If ... and it's a big if ... Tiffany is going to be committed to making it work."

"One other thing..." I said, "off the record?"

He raised an eyebrow, "Off the record."

"I shall be strict. I will be imposing a discipline that is ... rather outside the usual. And Tiffany will have to agree to that. You won't know about that ... officially."

A slight smile touched his lips. "I didn't hear that. But it would probably be best if you didn't repeat it as I might have to take official notice. I'm going to see if the estimable Hannah Barlow can find me some of her delectable fruit cake and a cuppa."

Tiffany sidled into my office and stood in front of my desk, shifting uneasily from foot to foot.

"You told me you were sorry," I began, "and I thought you really meant it. What should happen now, is that you go back to the Court and back into the system. Is that what you want?"

"No! Please! If there's some other way..."

"Okay, Tiffany. You've been more or less looking after yourself most of your life., so you're independent and impulsive and, frankly, selfish. You can work when you decide to, and you seem to have a ... talent ... for things mechanical. What I'm suggesting is probably not legal, but the end result can be that you are free of the system with a qualification as an automotive technician – probably a Higher National Diploma – maybe even a degree. You will have bed and board, you will work here and you will study. The study will be included in your working hours. You will work eight hours a day at minimum wage, initially, anyway, to pay off the repair to the car. That will take about ten to twelve years." She gasped. "Work it out," I said grimly. "About a quarter of a million pounds at six pounds an hour ... say, forty thousand hours, five thousand days, fourteen years if you don't take a day off and don't get a pay-rise. In the meantime, you need bed and food, so you'll need to work, say, five hours a day to earn your own living."

It appeared I was getting through to her as her dejection deepened. "Okay." It was barely more than a whisper.

"I am not going to put up with any bullshit," I went on, bluntly. "You will do what you are told, when you are told, without argument. Any serious problem, and you're out on your ear. Minor problems, I will punish you. I will personally punish you. I will not lay this on Hannah, or any of the other household staff. Do you understand?"

"How will you punish me?" She was looking nervous now.

"I will spank you. Either with a paddle or a crop, perhaps even a cane – depending on the seriousness of the offence, and it will be on your bare bum."

I'm not sure if 'shocked' or 'horrified' would be closer to her reaction at that point.

"I'm laying it out, up front," I went on, "so you can make your choice now. I won't be arbitrary, and make up things to punish you for. I'm not going to get sexual with you. I can get that elsewhere without complications. Clearly, this isn't something that can be formal. In fact, if you wanted, you could agree, then get me into trouble by complaining. So, make up your mind." I stood, and was about to leave the room.

"I'll do it," she said. "and I promise I'll try to keep out of trouble and I won't make trouble for you."

"Let's go and find Mister Sparrow," I said.

The long and short of it is that she quietly got on with work until she went back to court, where I was given custody until her eighteenth birthday, a year and a half hence. The magistrate was stern. "You are a very lucky young woman to get this chance. Bear in mind that if you get in trouble again, you will be tried as an adult. The youth services clearly have no more to offer you. So make the most of your opportunity," the woman smiled, then, "and when you are a qualified mechanic, I'll bring my car to you for servicing."

The next morning, Tiffany came to my office, asking to see me. "I've been thinking," she said. "I'm going to ... earn ... the cost of the repairs to your car, but some of the work is stuff I'd enjoy doing anyway. It's not a punishment..."

"And so?" I wasn't about to make it easy for her, though I thought I knew where she was going.

"I want ... I need ... for you to punish me for taking your car and letting you down. And ... Mister Weston ... I need for you to take charge. I need to learn to submit."

Well, floor me. I had thought she might ask to be punished, but not that. I looked steadily at her. "That's serious," I said eventually.

"I know," she nodded, still meeting my eyes, "I talked to ... someone ... and they said if I met someone I was sure I could trust, I should ask them to be my master ... or mistress."

"And you trust me?"

"I do."

Did I want this responsibility? "Do you want to put any limits on this?"

"No. I trust you."

"Tiffany, I want you to go and get on with your work now. Think about what you're asking and come back here tonight after supper. If we do this, you are putting your life in my hands. I will require total obedience. You will address me as 'Sir' in public and 'Master' in private."

"Thank you ... Master."

"Go, Tiffany." I made the rounds of my staff and asked Hannah, Jimmy and Bert to come to my office after lunch. Then, did a little shopping; I visited a pet shop and the riding equipment shop.

When lunch was over, we gathered in my office; Hannah, Jimmy and Bert all appeared intrigued, as I rarely called them all together.

"This about that Tiffany?" Bert was probably the most incensed by what he saw as her treachery.

"Easy, Bert," put in Hannah. "I reckon Mister Weston has something effective up his sleeve."

Jimmy just stood there, as he had the least interest in the girl.

"Right," I said. "I'm going to need your support, and you need to canvass the other household staff. If anyone is going to have problems with what I'm proposing, I need to know. It's going to happen, but anyone who has a problem with it can have a comparable job at a different site. That's easy, and it's a matter of conscience. That applies to yourselves, incidentally."

"Now, you've really got us on tenterhooks," Hannah smiled.

"Okay. I'm going traditional. First of all, Tiffany is going to repay the cost of restoring the Jag ... in labour. You can work it out that it'll take some time. Up to fifteen years, in fact. During which, she also needs to earn her living. So she's going to work eight hours a day for the Jag, and five a day for her living."

Three pairs of eyebrows were in danger of disappearing into hairlines. At least, one pair would have been if Bert hadn't been bald. His face gradually changed from anger to a sort of sublime pleasure as he considered the justice of it.

I couldn't resist singing the line from 'Mikado'. "My object all sublime, I shall achieve in time, to make the punishment fit the crime, the punishment fit the crime..."

Hannah seemed less happy. "That seems a little rough on the girl..."

"Those hours include everything, including training as a motor-mechanic. I will also be giving her bonuses and so on and paid holidays. She doesn't know that, by the way."

Hannah's face relaxed. "Okay..."

"The other matter is more difficult. It is, by the way, something Tiffany brought up herself. If she slips, she will be punished. The punishment will be proportional, and it will be corporal. I know that is politically unacceptable, but I believe it to be effective and necessary. It is also, as I said, something Tiffany herself raised. I have custody of her for eighteen months. After that, legally, she can just walk away, but I think ... I hope ... she will want to remain. Does anyone have a problem with this?"

They looked at each other, and Hannah spoke up. "If it were anyone else, yes. I'd have a problem with it. But, Mister Weston, I think you're probably the one person I would trust to be fair." Both Jimmy and Bert were nodding. Hannah went on, "There's one might be a problem, and I'll deal with her. She can go to the London flat, that's best, I think."

Tiffany duly presented herself at half-past eight, modestly dressed in slacks and a t-shirt.

"Master? You said to come after supper."

"I did. You want to carry on as I suggested this morning?"

"Yes, Master. I do."

I held up a sheet of paper. "I've prepared a list of my expectations, most of which I mentioned this morning, but what you said has changed things a little for me. You want me to be your Master, and you've indicated that again by addressing me as such."

"Yes, Master."

"Very well. In private, I will address you as 'slave'. In public as 'girl'. My first instruction to you, Slave, is ... strip."

I wondered if she'd baulk at that, but she didn't hesitate. She unbuttoned her slacks, slipped them down her legs and stepped out of them. Peeled the t-shirt over her head and placed it with the slacks, then reached behind to unhook her bra, releasing neat breasts that probably didn't need support anyway, and finally, with a little reluctance for the first time, stepped out of her panties. I stood and walked round her, and she stood still, though her head moved as her eyes followed me.

"Look straight ahead, Slave." I completed my inspection and returned to my seat.

"You are underweight, Slave. You will eat three full meals a day; I will speak to Missus Barlow about that. I want to eat at least one of those meals a day with you, if I am in the house. That had probably best be breakfast. Before breakfast, you will exercise in the gym for an hour, either with me or George. George will prepare a fitness programme for you. If necessary, we'll get you a physical to see if there's more than just inadequate nutrition involved. Hannah, Bert and Jimmy will co-operate in preparing a schedule of work, which will include two hours a day of study. Any questions so far, Slave?"

"No, s ... Master."

"Very well, then. Kneel." When she obeyed, I went on, "Are you sure you want to go ahead with this?"

"Yes, Master."

I buckled a broad dog-collar round her neck – the sort of collar you see on a greyhound or whippet. It was, literally, a leather dog-collar, not anything from a fetish store. "This, Slave, is a symbol of your status and you will wear it at all times except in bed or the shower, unless I specifically give you permission to remove it. From now on, you keep your eyes down unless you are told to look at someone with authority. For the moment, that is myself, Bert, Hannah or Jimmy. Okay, then. Stand."

I was not looking forward to the next bit. "Slave, you said you needed to be punished." I got out a paddle, a crop and a cane, thin and vicious. "Punishment was your choice. What instrument do you consider appropriate?"

She shivered, I am sure from fear. "Master ... the cane would be hardest, wouldn't it?"

"I think so."

"Then it should be the cane. Ten ... hits ... at least."

My heart sank, but... "Ten strokes? Very well, then. You need to count them and thank me after each one. Bend forward and rest your head on your arms on the desk." I knew better than to try to minimise the punishment. Her position exposed her vulva, which was initially closed.

I struck and heard the gasp of pain, the initial weal clearly visible. There was a pause. "One, thank you, Master."

I knew a pause between each stroke would give time for the full effect to build, though I hated myself as I did it. But as I continued, as Tiffany counted and as I could hear stifled sobs, I noticed two things. She was becoming aroused, her pussy dampening, blossoming open ... and so was I, becoming aroused, that is.

We reached the full count of ten and I told her to stand up; she was clearly weeping copiously, but there was also the scent of an aroused woman.

"You may dress, Slave."

Watching her dress, hoping she would not find the fabric against the stripes on her bum too painful, was quite arousing in itself. I stood by the desk, half watching, half trying not to watch. When she'd finished, she stood, waiting for further instructions.

"Slave, you are forgiven."



"May I hug you?" She was actually quivering, whether with fear or excitement or something else, I didn't know.

"Yes, you may."

Suddenly, I had about seven and a half stone (a hundred and five pounds, or forty eight kilos, if you aren't familiar with English weights and measures) of teenage girl wrapped round me like an anaconda. I could feel her breasts against me and the erection which had almost subsided returned with full force. She pressed against me and I'm sure she wriggled. The top of her head was about level with my jaw and her face pressed into the junction between my neck and shoulder. I could smell her shampoo. It was very, very pleasant. Too pleasant for comfort.

But then I realised she was crying again and I could hear the words, somewhat muffled, "Thank you, Master. Thank you, thank you."

I gently detached her. As I did so, her eyes flickered, momentarily, to mine. I saw a slight smile touch her lips, but it was so fleeting I wasn't absolutely sure and tears still streaked her cheeks. I handed her a clean handkerchief.

"Mop up, Tiffany, and go and relax for a while." Her eyes widened and flickered up to mine again, but still so momentarily I couldn't make an issue of it. Besides, I'd just slipped, hadn't I?

The next few months slipped by, largely without incident. Tiffany adhered to her schedule and was, for the most part, an exemplary 'slave'. Each day we ate breakfast together if I was not away on business, of course, and she gave me a run-down of what she'd done since the last meeting. I was getting very fond of her. From time to time, there was a minor incident – a broken cup, a miss-judged turn on the mower which cost several plants, perhaps an unacceptable expletive – trivial things, accidents or understandable omissions. In each case, Tiffany told me at breakfast before Hannah, Jimmy or Bert could. I'd have been tempted to let such things go but realised that was the wrong message. I had her undress and bend over the desk, and gave her five, or ten, strokes with the paddle as appropriate.

Each time, I finished once she'd dressed, by giving her a hug. Each time, she returned it with interest.

It was becoming apparent that the regime of good food and exercise was paying dividends. She was filling out, her bones no longer clearly visible, a very attractive young woman; everything in proportion, curves in the right places. Not for the first time I had a tickle of doubt about what I was doing, but I ignored it; there was just too much pleasure ... in looking at her, yes, but also in watching her blossom.

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Ma/ft / Consensual / Heterosexual / MaleDom / Spanking / First / Slow /