Winning Ways Ch. 02

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I just won the european lottery so what do I do now?
3.6k words
4.05
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Part 2 of the 2 part series

Updated 11/01/2022
Created 08/19/2009
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(thank you for the feed back on my first Submission. I ask you to please read these in order)

_____________________________

"Welcome Imogen."

There was no smile from me. This was part of our trade. I was to take control and dominate from the start.

"Take off your coat, slut."

She glanced across, noticing that the blinds to the office were open. Anyone in an upstairs room of the overlooking building opposite would see her.

"I said, take off your coat, slut. What's the problem?"

"Yes, master, but...."

"When I tell you to do something you do it, understand?"

There was silence. Her eyes seemed to be trying to find some spot on my newly fitted carpet. I even found myself following her gaze, so intent was she on looking at that one particular area. I smiled to myself. She was in role. She was mine. It was confirmed as she slowly began to unbutton the long leather coat, so incongruous on such a hot summer's day.

Then ever so slow revelation of first one full, natural breast and then the other made me quietly suck in air. Her nipples were as hard as diamonds, and projecting her shame. More buttons. The lightly bronzed skin shone under the office down lights and as her shaven mons was revealed to my intense gaze, I saw that she had been investing in a new collection of jewels. Her clitoral hood and labia were bedecked with diamond studded gold rings.

"So, is your cunt an investor's paradise now as well?" I asked sneeringly, mocking her for her wealth, knowing I was now her peer financially. I spat the word 'cunt' out like it was something to be regarded with disdain, knowing how she would feed on the humiliation.

"No sir, I had it done specially for you, but..."

"Shut up, whore, I don't want to know. Go crawl to the window, stand up and close the blinds, then get back on all fours like the bitch dog you are and crawl back to me."

I could see her sex lips glistening. This was arousing her intensely, yet there was hesitation again.

If you are seen by my neighbors then all well and good. Perhaps Mrs. Shah can be persuaded to leave that religious nut of a husband and join us," I joked, knowing the young woman in the flat opposite was kept a virtual prisoner by her fundamentalist partner. He was one of those who chose to distort the writings of his religion so he could keep his woman under foot. She wasn't there in a consensual way judging from the pleading look in her eyes that I had seen in those rare glimpses out on the street.

I stared at her with an aching desire to push my dick hard between her arse cheeks as she crawled for me; her firm buttocks high and the little puckered opening so inviting. It was almost too much imagining piercing that secret place whilst running my hands over the suspenders and stockings she had worn on my instruction. But no, it was as much fun to be the voyeur, watching her sex entice and sway between her legs, and the anus pucker like a kiss at me. It was also enjoyable to know that she was dirtying and probably laddering a perfectly good pair of stockings. Her ridiculously high-heeled shoes would be scuffed too as she crawled. How pleasing to force her to spend on new things, I thought. How delightful to have as much money to waste as she had. What a delicious thought after years of scrimping and saving, living on my business overdraft. Almost better than sex. No, nothing is better than that. Well, not when it is at the end of a lengthy BDSM scene.

And this was going to be one of those, with an unusual twist.

Imogen was crawling back; her head low but it was easy to see from the fiery red of her ears that she was shamed and embarrassed. She stopped at my feet, forehead to my Church's brogues.

"So, did anyone see you then?"

"Yes, master," she said, her voice quiet and with a slight tremor to it.

"Who?"

"It was that woman opposite. She was staring and staring at me and..." "And what?"

"Her hand gestured...to her breast...it was only fleeting but it was so...obvious!"

Hmmm, I thought. Just as I had suspected.

"You did well, slut. Now, suck on this."

I had my cock out, hard and throbbing. I knew she loved its thick and lengthy meat deep in her throat, and I enjoyed seeing her lipstick paint the shaft as she enveloped me with soft and full lips. As she raised her head, keeping her arse high like a primate, I saw the lusty smile on her face. What a beautiful, pervy woman.

And what an amazing feeling as she served my aching cock. But this was the entrée. I had other needs to be delivered on my menu.

"Suck slut...suck and drink it all down."

I came quickly. I had no desire to hold back. I watched almost dispassionately despite the shivers of orgasm that rippled through my body. I painted her throat with repeated spurts of hot cum. I was notingwhether she spilt a drop, hoping she would so that I could punish her but she cleaned me up from my cock-head to the base of my balls. She knew my exacting standards and had accepted them long ago.I could see and feel the hunger. I knew she loved it.

"Good slut," I said, praising her obedience.

"Thank you, Master."

"Now come to the desk and sit on it, facing me."

I gestured for her to sit on the centre of the large oak desk, but with her legs wide open, facing my black leather office chair and with her feet on its arms. I said nothing, but reached out to her cunt, plucking at each piece of jewellery; pulling the fine workmanship and stretching her cuntlips as much as was possible. She was so good, not flinching one bit, but her sex flowed with its own honey.

"Wet little cunt isn't it?"

"Yes, Master," she whispered, head down, eyes never meeting mine. Beautiful. Subservient just as I wanted her.

"Right slut, take that pad and pen to your right and take notes of what I have to say. You are to say nothing unless it is a question relevant to what I want you to do for me. Also, your face must not react to what I say either."

"Yes, Master," she said, voice bolder now; her body twisting to pick up the items. Her tits swinging freely, and the nipples so obviously aroused, it was hard to not push her back and fuck her there and then, but that was for later.

"Give me the riding crop to your left."

She twisted the other way now, picking up the leather tipped crop. She knew that she would be punished if she deviated from my instructions, but then that was the fun for her and for myself. I equally knew she would be unable to stick to these rules. That naughty side would crave its punishment.

I accepted the crop, given to me correctly in both hands and with a gentle kiss of its handle. I smiled and felt my cock rise, still free of my business suit. I slashed the crop down hard on the desk between her open thighs, watching her wince and then smile, inviting.

"Right, now listen, whore. I have won £75m on the lottery."

I watched her face, inscrutable. Shame. I wanted to strike her impudent breasts, so firm and full, so proud.

"Oh, you are cool aren't you?"

"If you say so Master."

I struck hard and fast across her right tit. She was caught out, breaking my instruction. Her scream was muted, but I knew it had hurt. Her thighs pulsed slightly; the creamy honey flowing as pleasure overtook her pain. Her essence was sweet and wonderful in the air. I laughed at my trickery.

"Now listen! I have met a new woman who frustrates me with her reluctance to marry me. She believes I am poor and of course I was bar the overdraft on the business and the services of my slut. She knows I am divorced and that I am a fucking good lover."

I stopped, scanning her face and body for reactions. Nothing. I had deliberately put that arrogant statement in.

"She seems to be implying that no matter how much we love each other she will not give herself fully to me. She wants first to have guarantees that I am solvent, that her daughter will be safe -- the bloody spoilt bitch that her eighteen-year-old is -- and that we move to a bigger house (which of course I could not do when penniless). Only then will she give me 'everything' as she puts it."

Not a move, not a sound. Impressive; especially for a mainly naked and open-legged woman. How did she look so regal wearing so little? My cock twitched and strained, hoping her composure would break.

"I want you to draw up a marriage contract. I want it to be a pre-nuptial that we both will sign and that contains some specific clauses that both protect me financially now but also specify what 'anything' will mean in the marriage."

"Can I please ask what the financial protection you want to build in should be?"

"Simple, if we split I want her to accept that she will be entitled to what she came in with, plus £1m only. Her bitch of a daughter can have 50,000 pounds only. I would also insist that she keeps the house under let, just in case. If there is any mortgage or loan against it, then I will pay that off. I doubt a divorce will happen but I want safeguards."

"Very sensible Sir."

I striped her left breast with four strokes in quick succession.

"You forget so easily."

"Sorry Master."

Her face was a picture. She realized her mistake too late.

Four strokes of the crop striped the right tit. She stifled another scream. I laughed, heartily, enjoying watching her go from pain to an expression akin to orgasm, but not quite there... yet.

"There are some sexual practices that she, Nirvana, is resistant to. In fact she has some serious hang-ups about sex. It's a complete paradox. One minute she is a horny bitch, pushing my head between her legs to lick her shaven pussy but then will avoid being kissed once my face is covered with her cunt juice. Do you think that is weird? Also, if she pisses or shits at home or a relatives she has a shower immediately afterwards. Her cunt has no smell it is washed so frequently. When working or travelling, she will hold back her shit until she is home. Then she has gut problems, the stupid bitch, from that holding back. If she has to squat and piss or use a public toilet, she will wash and wash if there is a sink. However I have known her hold her piss until when home she has wet her panties dashing to the toilet. On those occasions she has laughed afterwards, as if there was some pleasure gained but she would not admit it. There is over many things a sense that behind the repression is a slut of a woman wanting to get out.

So, what does this have to do with you?" I stopped, noticing her face.

The stripe made over her left titty was inevitable. I had seen the quizzical look. She had failed my order, much to her chagrin and my pleasure. I smiled, pleased with her discomfort.

"I want a clause included that states she will as part of our marriage agreement receive exactly one quarter of my remaining fortune after payments (of my choosing) to my children and ex-wife. To receive the total sum of about £18.5m, which will be given in stages over a 15 year period (with cumulative interest of course) she is to agree to sexual therapy with the clinic of my choice. Make sure that there is no get-out clause in the wording. I know exactly who she is going to, but she is not to be aware of what type of therapy this will be or how I will ensure she is 'loosened up'."

"Yes, Master."

The rapid flick of the whip across her pussy must have seriously hurt, yet she made no change of expression. Only her body moved, absorbing the pleasure and the pain. Good girl, but of course that is not what I told her.

"You are a disobedient slut today. I think you will be going home looking like a burger fried on a griddle. I'm going to criss-cross your body mercilessly."

God, I was hard! I wanted to really punish her. Did having all this money usually make people feel so powerful, almost invincible? Now I was on a roll. Here was my chance to really control more than just this slut who was there for the BDSM and the fucking. I could control the woman I loved and it was not incompatible to love her and humiliatingly control that dusky maiden. I knew that would give me the greatest pleasure.

"Also, I want it written in to our agreement that she will dress to please me. In particular, she will never wear knickers again unless it is a hygienic necessity. Do not specify precisely when that might be, as I want it written in that such times will be agreed with me.

Finally, I promise to her the greatest pleasure. I pledge that my whole focus will be her happiness. She will never have to lift a finger to cook, clean or shop unless those activities bring her personal pleasure. Her currently badly spoilt daughter will be well cared for. Put in some positive wording, but suggest -- and only suggest, do not make it a promise -- that should I be given joint rights to bring up the child I will give the young woman a significant sum when she achieves an appropriate age and level of maturity. Imply that I will expect some changes in methods of punishment and reward. Tell her that she may wish to consult her daughter to ensure she knows there is a choice: her mother need not marry me and have access to such a fortune and she can be free to do as she does now. That should challenge the Bitch's mind.

Have you got all that? You can speak now."

"Yes Master, I just have a few questions but they may be best to ask when I have drafted the core document and then I can come back and work with you on the final document. It will take me about a week."

"You have two days slut and that is all."

Her face screwed up. I knew from a previous conversation she had an important corporate client to deal with. Why was I being so cruel? Because I needed it and I knew she did too.

I beat her so harshly, the crop slicing across her breasts and belly, criss-crossing as she lay back accepting this was for her misdemeanor. I was methodical now, keeping each stripe an inch from the next, then stepped to the side and came across the other way creating that 'burger' pattern. I laughed at her, insulting her as I knew would turn her on, the perverted little slut. I soon had a marvelous pattern as her tears streamed down her face and her body quivered, pain and pleasure only a fine line apart.

"Turn over bitch."

Her backside had four purple marks, but I knew they were not from me. Who cared? I didn't. I just added more stripes and instructed her to get up on all fours.

"Now, I want you to tell me all that you have been doing since we last met. Tell me about your lovers, male and female. Tell me which ones you think could help us pervert Nirvana and which you think could be good clients to send my way. You know how I like to mix business with pleasure. Incidentally, I have not intention to give up my job but I do intend to expand the company and maybe even explore partnership with yours? Think about it as I spank and fuck you..."

"Yes Master, but please, please spank me because I have been so naughty since we last met."

I raised my hand and with the fingers wide apart spanked her gorgeous firm arse, while I kept a recording going to capture the information that I would give to my trusted PA, Ms. Mapledorum. Now she readers, is a woman chosen for her discretion but whom I knew (from watching her on my discretely placed CCTV) is a secret sexual minx. This tape would tease and torture her with its strong sounds of whipping and spanking; not to say rampant fucking and sucking.

Imogen screamed, but this was not with pain. It was an orgasm induced purely by my hand striking her arse cheeks. It was a small one, nothing like some I knew she would have, but I smiled knowing that I could get her off just with such a simple but cruel action.

"Oh, Master forgive me for cumming so quickly. Please, I have been very naughty and will make up for it with my true stories."

* * *

Imogen left striped not so much like a hamburger on a grill, more like a fine piece of graph paper. I used the crop everywhere, and I mean everywhere. However, she did not flinch once, absorbing all the pain to get the gain. She had so many orgasms and I did not deny her a single one. I was too kind that day, but then I wanted excellent results from her and I knew that if I played her correctly, I would get them.

Oh, was my cock sore readers. I had fucked her all afternoon front and back, had my dick sucked repeatedly and yet still managed to listen to some of her most sordid tales. I'm surprised the Bar has by now not struck her off. She has fucked and sucked her way through more clients than I have had hot dinners, but then she has so many secrets in her safe about them all that they daren't complain, I guess. Plus, she has just started a concerted effort to transfer to the bench and become a judge, so is now collecting dirt on the best of the judiciary. I had never realized, for example, that Lord Stokes of Mapworthy was a foot fetishist who had spent all of last Saturday night naked on Imogen's cold kitchen floor. She had kept him lying prostrate whilst licking her feet to a state of pristine cleanliness; cumming all over the stone and lapping it up on command. He may be 70 years old but he is still as randy as he was in his 20's and Imogen described his dick as the longest and thickest she had ever seen; apart from mine that is.

Nor had I expected that Judge Judith Smithers was a raving dyke who had kept Imogen under the table at a dinner party for her lesbian friends. My lawyer had spent all night on her knees licking Lezzie pussy whilst dressed in what was apparently 'a ridiculously short maid's outfit with no panties,' she said. However, the horny lesbians were too stupid to notice that Imogen kept her little shoulder bag with her at all times. Ms Mavis Mapledorum would love transcribing the evidence for her that had come off the micro-recording device she used and the pinhead lens camera. Just a few minutes of slurping mixed with some very indiscreet conversations top of table and jerky but explicit images below would be worth so much to further her new ambitions. Judge Judy had a marvelously distinctive mole on her inner thigh. Very nice place for a beauty spot Imogen told me. However, was it my imagination, or did bi and lesbians scream louder when they came than hetero women? Whatever, that group had been particularly uninhibited in their pleasures and now I had the evidence to share with Imogen. I would ensure Mavis made a copy. Well, you never know when I might need it readers, do you?

When I got to Nirvana's that night; I was in no mood for more fucking. I stayed for dinner, gritting my teeth as 'The Bitch' made her snidey comments whenever I raised an opinion different to hers. Then, after the meal she proceeded to hog the TV control, never asking what her mother or I wanted to watch. Yes, she was one spoilt motherfucking cow who hopefully in a few weeks would receive the shock of her bitchy little life. I made my excuses, noting the transgressions in a little notebook I'd taken to keeping since I'd started dating her mother. 'One day' I had thought to myself, uncannily confident that there would be a time when I could exact either revenge or better still some correction of her daughter's behavior. Of course in that book I also kept thoughts on the things her mother needed to do to break out of her prissy self. I smiled that night as I felt the power my new wealth gave me.

I drove home with a cock so hard it ached inside my Calvin's.

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AnonymousAnonymousabout 2 years ago

The life of an enriched, sick fuck. This protagonist seems the type to run for public office so he can buy into the "flesh sales" trade (for Brits, you call it "grooming", before the "sale"), age non-restricted.

Sadist would be a term too acceptable for the level of ignorance included (even if this is supposed fantasy, I can see the guy being a cuck under it all, especially since he is in the Euro-zone and has ZERO morals)

AnonymousAnonymousalmost 3 years ago

U A BIG DCK

sdbnncsdbnncover 14 years ago
Looking forward to reading more!

The fantasy of a lottery win coupled with a very realistic portrayal of the needs of submissives and Dominants for the power exchange of their relationships makes for interesting and engaging reading.

Again, please get a proofreader or editor to assist with tuning up grammatical glitches to further enhance the reading experience for those of us who are put off by those things.

You are telling an interesting story very well! Thanks for sharing your talent.

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Winning Ways Previous Part
Winning Ways Series Info

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