As her family was not entirely well to do, Tanya grew up telling herself that in order to escape the poverty that she had “suffered” during her formative years, the only way was to marry rich. Thankfully she was quite the looker and thus had her many fair share of suitors. She modelled part-time during her poly studies and once in a while did a stint or two as a social escort. It wasn't the terribly sleazy type for no sex was involved and it was, for her, a way of getting to know the rich. Things seemed to be going rather smooth for her and by the time she was in her final year, she managed to hook up with a relatively rich and single businessman who was in his early thirties. By the time she had graduated, they were planning their marriage and at the age of 21, she was happily married to this rich guy and living the life. It literally was a bed of roses for her as she lived the life that maybe could only dream about. Hi-tea and social functions, shopping almost everyday, and the man she married was a decent enough guy, albeit a little boring, who gave in to her every whims and fancy.
But as a wise sage once said, all good things must come to an end. The economic downturn loomed near and as businesses began to fail and crumble, her husband's business was not spared. To make things worse, his investments also lost a whole lot of money. And in the end........he took his life, a bunch of sleeping pills and it was over, for him at least. As for Tanya, all she got was an apology letter and a whole truckload of debts which were thrown on to her by the fact that she was his wife. And thus, at the tender age of 26, she was a widow and a bankrupt. It wasn't so much the loss of her husband and wealth that devastated her, but the humiliation of having to return to the life she used to live with her poor parents that she could not stand. And so, it was a mere matter of months before she was back onto the “circuit” in a desperate bid to find another rich man. Now the business associates of Tanya's now-deceased husband were all more than happy to shower their sympathetic condolences on her, in a bid to get in her pants. The only problem was......they were all married. But it was also a known fact that Tanya was sorta the money grubber, for.........let's just say (out of respect for the dead) that Tanya's deceased husband was not the good looker and thus it didn't take rocket science to piece it together. And so.......straight in her face, the business associates offered her “terms” of luxuries if she'd only be their kept woman. The terms were rather tempting, honestly, but I guess apart from the wealth.........Tanya wanted a certain amount of status as well. The social circle that Tanya and her deceased husband use to mingle with was relatively close and she knew almost all of their wives. It was already a loss of face to her that her husband had “cowardly” (as she put it) took his life, and so she wasn't going to “degrade” herself further by being some kept woman to one of the husbands of her rich tai-tai friends. The rich women in her social circle were also beginning to be wary of her, for she was one of the youngest among them and they knew that many a time their own husbands had looked at her with such lust for minute too long. And so they began to shun her, also for the obvious reasons that she could no longer afford the past-times that they use to enjoy together.
Then came along Mr Ng, one of the wealthier businessmen that mingled in their social circles. He was well respected, solidly rich and most importantly.......a widower. The only problem was.......he was in his late fifties and fast approaching his sixties. Well Mr Ng did not exactly “come along”, in fact when Tanya's husband had passed away, unlike the rest of the associates, he merely offered his sincere condolences and never once attempted to offer the “terms” that the rest of the men had offered. It was rather Tanya who made the first attempt. It was a rather calculated move on her part, and maybe a last ditched effort. For it seemed that most of the other men, whom she knew were all already married and were only willing to take her on as a mistress. At the same time, she did not have anyway of “penetrating” into the other rich social circles for returning as a social escort was deemed by her as too humiliating and she did not have the funds to pay for her way in. And then she remembered Mr Ng. When he had sent his condolences, he had told her that if she needed any help, she could approach him. And so after much thought, she decided that, despite his age, it would not be as humiliating as being a kept woman. Problem was, it was only a thought on her part, for Mr Ng had not made a move on her and never did express any interest in her. Nevertheless, Tanya had set her sights on him and decided it was a make or break in trying to “hook up with him”.
And so, dressed in her sexiest outfit, that didn't scream slutty, she made her way to his office without an appointment. Thankfully he told his secretary to let her in and soon enough, the flirting began. Now, the information that I collected on this phase is not sufficient for me to describe it in full detail. But what I do know is that, Mr Ng resisted her advances at first. He knew that it wasn't because of who he was that Tanya was hitting on him, but rather of what he had and could provide for her that she was doing what she could. He found it a little repulsive at first, but then a thought dawned upon him. He wasn't getting any younger, his children had all grown up and moved out (and on with their own lives), he was in a sort of semi-retirement (until his children could fully take over the reins of his company), and it was starting to get a little lonely and quite boring. Then her was this pretty young thing who was throwing herself at him...................and plus, he could sense the desperation in her. The sort of desperation that could pave the way for a little power play. But still he wasn't so sure. And so he decided to open up a little to her advances and took her out to dinner a couple of times, which usually led to a hotel room (at Tanya's subtle suggestion on all occasions). All this time, Mr Ng was just playing along with her advances and debating in his mind if he could take her as a companion. Like a shrewd businessman, he used the same mindset towards his decision. Then one of the nights, as they both laid on the bed, he sat up and matter-of-factly told her that he knew the “motivation” behind her advances. It took Tanya by surprise, for she thought that she had “masked” her real intentions pretty well (but it was pretty obvious according to Mr Ng but he had played along and not exposed her), and she tried to deny it. But only the initial few words came out before Mr Ng cut her off and asked her to let him finish his piece.
It seemed more like a business deal (to me at least when he related this to me). Mr Ng offered his terms to her. He made it clear that he was not looking to remarry. He was however open to the possibility in a life-time, live-in companion (until the end of his lifetime at least). He was willing to provide a life of comfort and luxury, and also at the end of his life, if she stayed with him throughout, he would will him a substantial amount that would last till the end of her lifetime. However, there were some restrictions. There was to be no toy-boys, he would not except infidelity. She was not to fight over the company with his children. And it was his way or the highway. Strictly his rules and whatever he said goes. As his companion, there were social functions to attend and there was a certain way she had to carry herself. He had a reputation, and he did not want it embarrassed. He wasn't conservative, but rather traditional in the Asian patriarchal sense. Some would call it MCP but well, its all about perception (as Mr Ng would say). He had intended to give her a few days to think about it, but I guess........since the cards were laid on the table so clearly, she accepted almost immediately.
She moved in the very next day, but before it was all made formal, Mr Ng had an agreement to his term (seriously) done up by his lawyer for her to sign. It even had a clause, which if she found it unbearable or for whatever reason wanted out of the relationship with him, she could, just that all of the benefits promised after his death would be rendered null and void. Talk about consensual.
So back again, at the age of 27 years old, Tanya was back to the life on a bed of roses but this time, with a guy 30 years her senior albeit much richer. The first few months were similar to the “honeymoon” phase that many couples go through. And once again, Tanya was in the company of the rich tai-tais who had shun her when her husband had passed away. Mr Ng was quite the gentleman but he wasn't the pushover that her deceased-husband used to be either. He knew exactly what he wanted and he never failed to remind Tanya about the agreement on “his way or the highway” whenever Tanya tried to bully him into going her way. Of course he did play along and accommodate her on trivial things every now and then, but on bigger issues, Mr Ng made the decisions. Especially for social functions. While Tanya was like a “medal” on his arms during such functions, thus he acknowledged the fact that he dresses could be too frumpy, like what most of the middle-aged or older tai-tais wore, but he wasn't about to have her dressing like a slutty young girl out to prom either. Sometimes, little arguments (more like verbal debates) would ensue over the dress Tanya wanted to wear but in the end, it was Mr Ng who made the final decision. Punctuality was also an issue to Mr Ng. He hated to be terribly late for functions, and in fact he found it terribly embarrassing. But one time too many (in Mr Ng's opinion), Tanya would take a hell of a time in her preparation to get dressed that they either had to rush or were a little late. Not that the hosts or other guests minded but to Mr Ng, it was about principle......his principle. The way one carried oneself was also an issue sometimes to Mr Ng. I guess, gossiping loudly and shrieking with laughter is sometimes frowned upon. I guess there was also the expectation that Tanya be by his side at the functions and make small talk with the frumpy old wives of the men that he would be talking to at that time. But the age gap between them made common topics far and few. Tanya was more comfortable talking to the younger wives, who were closer to her age, but the problem was that they were wives to men who were lower in the corporate ladder and thus not the men who mingled around Mr Ng. The ladies of that social strata were also probably not confined by their husbands to stay by their side during the functions. And many a time, they would be in a corner themselves gossiping and chit-chatting away. Whenever she could, Tanya would slip away and join them in their “wonderful” conversations, which sometimes would get a tad loud. Mr Ng was pretty understanding, as he let her off to mingle but expected some consideration on her part to remember to return to his side after a while. Of course this sometimes didn't go to his liking, especially when she would get carried away and he would have to walk over with a smile to “get her back” to his side. He never lost his temper in public, reputation I suppose, but ever so often, he would whisper in her ear, his slight dissatisfaction, with a smile still so that everyone else would be nonethewiser. Of course once they were in the car, he would sometimes give her a dressing down as the driver drove on in silence. Tanya would normally try to butter him up and with apologetic words and the sheepish girlish words that she really got carried away. This worked each time, although Mr Ng would each time give that “Make sure it doesn't happen again, or else....” He never elaborated on the “or else” and Tanya did assume that the or else was just his old eccentric way of being stern.
Oh but was she wrong.
Mr Ng told me that he actually had “darker” plans (well spanking plans) from the start, which would explain his “my rules” agreement, but he decided to give a few months before he made his move. And when he made his move, it was a classic situation. One of those days when everything goes wrong. There was a social function, and Tanya was feeling lazy and did not want to go. However Mr Ng insisted and thus she had no other choice but to get ready. Of course, being reluctant, she took her own sweet time, and by the time she got ready, they were close to being late, but would have made it on time if they rushed abit. However, being in the mood that she was, Tanya chose a dress she fancied but knew that Mr Ng would frown upon. Of course Mr Ng was not about to let her go for the function in that dress, and after a slight “verbal debate”, Tanya grudgingly changed into a more “suitable” dress, but by that time they were already late. By the time they reached the function, they were an hour late and Mr Ng was quite the irritated gentlemen. While the usual smile was on his face as they entered the function, he made know his irritation to Tanya as he whispered into her ear and told her that she'd better not make it worse by disappearing longer than she should today. Tanya on her part was also slightly irritated that she had to make her appearance, and thus decided (to herself) that she wasn't going to care at all today. And so at least three times, Mr Ng had to “get her back” from the group of young wives and by the last time, some irritation could be seen on his face. Knowing that if he stayed any longer, he may end up losing his temper and his reputation, he took his leave from the function early and got on the car with Tanya, who at that time was secretly happy that they were leaving early. However, when they got in the car, Tanya noticed that instead of “nagging” or scolding her in the car like he normally would when she disappeared from his side during such functions, there was a stern silence and look on Mr Ng's face. Wondering if she had “pushed his buttons too far”, she tried to butter him up as she normally did. But instead of the usual response she would have gotten, her attempt at buttering him up elicited a rather harsh verbal lashing instead which ended with a “Wait till we get home.” And then there was silence.
Reaching home, Tanya didn't really know what to expect and just proceeded to shower. When she came out of the shower, in her bath robe, Mr Ng was sitting on the edge of the bed looking sternly at her with his arms crossed across his chest. He looked more serious and upset than usual, but Tanya avoided his eyes and walked towards the dressing table. But she had only taken a few steps when Mr Ng asked her to come over. He asked her to seat next to him and asked her if she remembered what their agreement was. She nodded, but he asked her to say it out verbally which she did. And when she got to the part about “his way or the highway”, he stopped her and asked if she knew what it meant when she agreed to that. Not knowing what answer he wanted, she mumbled that it meant that she was supposed to listen to him. She tried to play the nice-sweet-little-girl as she said that for she leaned her head on his shoulder. Mr Ng didn't budge but kept silent for a moment, then said that she didn't seem to be listening to him but rather at times seemed to be purposely testing his patience. This drew a girlish giggle of a response from Tanya. To which Mr Ng reached over her shoulders and patted her head as he commented a “So you really think this is funny.” (Or something like that)
Then with a “It's alright......this is what we'll do.”, he pulled her across his lap. She giggled as she tried to struggle, thinking he was playing around, but he held her down (he was quite fit for someone in his late fifties) and gave a rather stingy spank to her bottom (which was covered by her satin bathrobe and offered little protection) as he sternly told her to keep still. Beginning to suspect (or realise) that Mr Ng didn't seem to be playing around, she held still but gave a girlish kinda whine (I can't describe it, but its the kind of whine that you know your female partner would give when they wanna worm out of trouble, but are not yet pleading for mercy yet?). To this whine, Mr Ng gave another sharp spank to her bottom and told her to keep quiet. Mr Ng then went into this long lecture over what he actually meant about “his rules” in the agreement and that corporal punishment was something he had in mind all along. He continued that he had taken the past few months to see how much was needed and after that “terrible showing” that night, he concluded that much “work” was needed. He then asked Tanya if she had ever been spanked before. Tanya didn't reply much to Mr Ng's irritation and he gave a harder spank this time to hard bottom as he repeated his question. To which Tanya responded with a rather loud gasp-no (a gasp and a no at the same time) but also added a wisecrack question of “didn't you ask me to keep quiet in the first place”. This resulted in a further sharp spank to her bottom (which drew another gasp) from Tanya, as Mr Ng commented that it wasn't going to help her bottom if she was going to be a “smart ass” and also said that it wasn't too late to learn what a proper spanking was. And then he started spanking her, at a constant pace for around a minute of two. It must have been relatively hard for she kicked and gasped and pleaded from the first spank onwards. And as soon as he was done, Mr Ng told her to get up and remove the bathrobe. But Tanya knelt down clutching her bottom, giving a pout and insisting that she had learnt her lesson and didn't need her bottom to be spanked anymore. But Mr Ng would take no bargaining, and simply told her that it was up to her. She could leave or she could “follow his rules”.
There was silence for a short moment and then Mr Ng asked, “So? What will it be?”
Keeping that pout, Tanya got up, removed the bathroom and let it drop to the floor before slowly going back over Mr Ng's knee. The spanking that came next was faster and more furious, as Mr Ng spanked at her bottom for a full five minutes, leaving Tanya gasping and all teary and pleading for Mr Ng to stop. And the moment Mr Ng did stop, Tanya slumped off his knee and onto the floor, clutching her bottom and sobbing softly. Mr Ng helped her up and sat her on his knee as he massaged her bottom lightly.
“I guess we will stop here for now.............its getting late...........but I promise you.......things are going to change from tomorrow onwards.” Mr Ng said softly to Tanya.
“Yes darling, I'm sorry.........it not going to happen again.” said Tanya. I guess she misunderstood Mr Ng, for he actually meant that he was going to resume the spankings the very next day.
The very next morning, bright and early, Tanya had all washed up and was about to wake Mr Ng up to go for breakfast. But as she walked out of the toilet, it was as if it was deja vu for she saw him sitting in that eerily familiar position on the edge of the bed as the night before. Brushing of that thought of familiarity in her mind, she gave a smile and walked towards him to plant a kiss on a forehead and clasped his hand as if to lead him off to breakfast. But instead of feeling Mr Ng get up to follow her, she felt resistance and then a pull which result in her over his knee again. But this time, before she could even struggle or voice her protest, Mr Ng held her down and told her to keep quiet and “Let's have a little warm up before breakfast.” as he gave a “warming” spanking for a couple of minutes. And as he spanked he reminded her that he had promised her that things were going to change from now on and this was how it was going to change. Tanya of course tried to voice her protest to this to which Mr Ng pause for a bit and asked “So are you saying that you intend to leave?”. This was met with silence from Tanya and Mr Ng gave a “I didn't think so.” as he continued to rain down the spanks. He didn't lift her bathrobe this time (only a warming up he reckoned), and as soon as he was done spanking her he let her up and told her that they would continue this after breakfast.
During breakfast Tanya tried to plead and “negotiate” if he could not spank her, but Mr Ng gave a warning that if she tried to “fuss” about it anymore, it would be worse. This stopped anymore pleadings from Tanya and the conversation went on to other more frivolous things.
After breakfast, which was actually sort of like brunch, Tanya remained at her seat in silent anticipation, not knowing what Mr Ng had installed for her. She thought she had heard him wrongly when he asked her to get change for they were going shopping. But when he repeated himself, her heart jumped and rushed to get ready thinking that he must have felt bad for spanking her.
When they reached the boutique they normally shopped in, Mr Ng told Tanya that they had five functions the following month and told her to pick out five suitable dresses for the functions. He then told her that he had to meet an associate to settle something and they arranged to meet for tea at one of the hotel restaurants a few hours later.
Time flew as Tanya shopped and hi-tea at the restaurant was pretty enjoyable. It seemed as if the spanking was just a one off and a distant memory thought Tanya as she sipped her tea.
But she soon realised how wrong she had been when they reached home.
As soon as they reached home, Mr Ng told Tanya to bring the shopping up to the bedroom and he was going to inspect them.
As soon as she place the bags on the floor, Mr Ng asked why were there seven bags instead of five. Matter-of-factly Tanya responded that she had bought seven dresses. Giving a sigh and shaking his head, Mr Ng replied that it seemed that she wasn't following his instructions once again for he had only told her to get five dresses. Tanya tried to defend herself and said that she didn't know that it was some sort of test and that she wasn't supposed to buy more than she was told.
But Mr Ng was not going to hear any of her excuse. Gently leading her by the hand to the edge of the bed, he reminded her once more that he had already told her the day before that thing were going to change. And he lead her over his knee but paused and then told her to get up and remove her clothing. Tanya hesitated but Mr Ng's warning that it would be worse if she resisted saw her quickly remove her clothes.
Then it was over the knee and he gave her two minutes of handspanking for each extra bag of clothes. She was tearing by the time the four minutes were done but it wasn't over yet.
Mr Ng then told her that he had let her shop alone and pick out the dresses to see if she would listen to his instructions of picking “suitable” dresses for the functions. Then pointing to the first bag, he told her to put on the dress. Tanya gulped as she wore it for she knew that it was one of those dresses he did not like her to be wearing for their social functions. Shaking his head as he looked at her dress he asked if Tanya if she felt he would agree to such a dress. Tanya kept her eyes down and shook her head. “So why did you buy it still?” Mr Ng asked. Tanya kept quiet not knowing what to reply.
Removing his belt he told Tanya to put her hands on the bed, bend over and stick her bottom out. He then gave her ten hard lashes with the belt in quick succession. The stokes were fast and hard leaving Tanya gasping and crying out softly and teary with each lash. And then he told her to remove the dress and put it back into the bag, and then to get back into the same position. Once again, he gave her ten hard strokes with the belt. As she squatted down clutching her bottom after the last stroke, Mr Ng told her that this was going to be the same punishment for each of the next six dresses if they did not meet his expectations.
The next two dresses once more were an obvious show that Tanya had “purposely” chose the dresses that Mr Ng would not like for the functions. And thus both times, she got the twenty strokes (ten with the dress on and ten with the dress off). She was a sobbing wreck by then and so when Mr Ng told her to assume the position once she had put on the fourth dress, Tanya was already crying before Mr Ng landed the first stroke. By the second stroke, Tanya could not keep the position and was kneeling on the floor clutching her bottom pleading that she could not take anymore.
So then Mr Ng walked out off the room and brought back with him four restraints that could attach to the bed (it was a four-post bed). But Tanya was still pleading that she couldn't take anymore. So Mr Ng sat on the bed and told her firmly that the punishment was going to be given. She had only three choices. 1 – Get back into position and stay there. If she got out of position, he would start from zero. 2 – He would use the restraints, but that would mean two extra strokes per set. 3 – She could leave and the punishment would cease immediately.
Tanya sat there motionless for a few minutes, sobbing and rubbing her bottom. Mr Ng waited patiently, himself slightly amused and wondering which option she would take. Then with a deep breath, Tanya got up took the restraints and told Mr Ng that she wanted to be restrained.
So she was restrained. With the dress, Mr Ng restrained her in a stand-up spread eagle position. And without her clothes, Mr Ng restrained her spread eagle on the bed. With the extra two strokes per set, this meant 24 in all for each subsequent dress. And none of the dresses made the cut, which meant 24 strokes each for the fourth, fifth, six and seventh dress. I guess Tanya knew that that would be the case and thus chose to be restrained.
After the last punishment for the last dress, Tanya was a crying loudly and pleading and apologising. Mr Ng stood back for abit admiring her red quivering bottom. He left had left her in the restraints for he had one more thing he had to do. All that spankings had left him with a major hard-on. Removing his clothes, he climbed onto her and pounded her as she was restrained in her position. There was some slack in the restraints and he was able to lift and manipulate the angle slightly. Amidst the tears and pain of Mr Ng's groin slamming onto her reddened bottom was also the pleasuring feeling of his manhood piercing into her swollen privates. It was not the first time they had sex, but it was the most erected that she had ever felt him. And as she buckled in a powerful orgasm of pleasure and pain, he shot his load and collapsed on her whispering, “Let's see how you fare tomorrow at the boutique.”
I am going to stop here as I noticed that this is already very long. I guess I will have to split this whole story into parts. So stay tuned!!