Doretta's Mistake - Cover

Doretta's Mistake

Copyright© 2012 by Amasterfound

Chapter 1

BDSM Sex Story: Chapter 1 - Doretta has a big gambling problem and it will cause her to lose her freedom when she can't pay back a loan shark. The twist? It's not the shark, but her brother Anton who claims ownership of his little sister.

Caution: This BDSM Sex Story contains strong sexual content, including Ma/Fa   Consensual   Reluctant   Heterosexual   Incest   Brother   Sister   BDSM   DomSub   MaleDom   Spanking   Rough   Sadistic   First   Oral Sex   Anal Sex   Sex Toys   Squirting   Size  

Doretta sat at the table and thought that she had really done it this time. What could she do? She had to come up with five thousand bucks and fast. If not, she was in hot water! Why had she ever borrowed that kind of money from a loan shark in the first place? Damn, she thought, it was a sure thing when she bet on that horse! In the last lap, it stumbled! Shit, of all the luck! If it weren't for bad luck, she'd have no luck at all!

Doretta tried to see how she could get out of this newest jam! Fuck, why didn't she learn her lesson the last time? She dreaded going to him again! He warned her the last time around what would happen if she got herself into another such jam and he had to bail her out. Why did her father have to put that fucking clause in his will! When she was sixteen and that drunk driver killed her parents, she found out that her brother was to be her guardian. Anton was five years older than Doretta was. She resented the fact that she couldn't touch her part of the millions that were left to them without his consent.

Damn it! Why did her father have to be so fucking Old World! Even her brother had the same damned attitude as him. She understood her father, since he was from Greece and that was the way his family had lived for centuries. They felt that a woman had to be under a man's rule throughout her life. When Mom and he moved to America, his beliefs had not changed. Her brother threatened the last time she messed up that if it happened again she would no longer be a single woman. She'd fall under the complete authority of a man. Even worse, he claimed to know which man would control her, but he refused to tell her his identity.

Doretta didn't agree with the idea of male dominance. The very concept of being dominated by a man terrified her. She was afraid that it would cost her the freedom that she worked so hard to achieve. That was not an easy job, given her family's way of life. While still a virgin at the age of twenty-four, she wasn't narrow-minded or vanilla. She simply hadn't found the sort of man who interested her enough for sex. Her brother also made this difficult for her. He constantly "discouraged" any male attention, including from his own friends. He was extremely over-protective of his sister, especially since they lost both of their parents and she was his closest relative left.

The ringing of the telephone startled Doretta. She knew whom it would be instinctively. It had to be "Big Ed", wanting his money immediately. She contemplated not answering the phone, but knew that this tactic would only infuriate him further. She'd put him off too long already.

"Hello?" she answered.

"Ya got the money, sweet cheeks?" "Big Ed" asked in a patronizing tone.

"Um ... not yet. I had trouble getting it. Can you give me a couple more weeks?" she begged.

"That's what you said two weeks ago. I told you then that it was your last chance. Time's up. I'm getting my money, one way or the other!" he warned her.

"What do you mean by 'one way or the other'?" she asked fearfully.

"If I don't get my money within the hour, you'll find out, Missy. The clock is ticking now!" he hung up the phone without saying another word.

Shaken, Doretta looked at the phone, realizing that she was in deep shit. There was no way she could get five grand in less than an hour without going to Anton. What would she do? What would "Big Ed" do? She feared what her older brother would do even more than she was afraid of the loan shark. Should she call him? She picked up the phone and decided to ask him if she could have five thousand to "gamble" with. That might work, she thought to herself, if she came up with a believable reason to bet.

Doretta dialed his phone number, waiting anxiously for him to answer it.

Anton looked at his caller ID, noticing that it was Doretta's phone number on display there. His sister seldom called unless she needed something or was in trouble. He knew that she disliked the idea of his being in charge of the money. He wasn't going to give his sister her share of the inheritance yet. She hadn't proven enough maturity in financial matters. He only hoped that this time she hadn't gotten herself in serious trouble, but he had a gut feeling that she had.

"Yes, Doretta, what do you want this time?" he answered.

"Hi, Anton. Why do I have to want something to call my favorite brother?" she buttered him up.

"I'm your only brother and any time you start to butter me up, you want 'something'. Now, what is it? How much money do you owe this time and to whom? Or is it that you want to gamble away money again?" he asked her, getting too close to the truth for her comfort.

He had always disapproved of her gambling habit.

"Uh, I wanted five grand to take Candy to the casinos for a girls' night out? She's been kind of depressed over her last break-up, and I wanted to cheer her up," Doretta pleaded.

Anton objected to Doretta's friendship with Candy, who always seemed to get her into trouble. Candy was also, unfortunately in Anton's opinion, a very modern, "liberated" woman. She was notorious in high school and ever since as indiscriminate with her sexual partners, which was something that Anton frowned upon. He did not hold to the "abstinence until marriage" school of thought, but neither did he like sluts. Candy seemed to have a lot of "one-night stands" compared to serious relationships. Her boyfriends usually didn't last very long, either, hence the latest incident.

"No, I'm not going to give you and your slut 'friend' cash to fritter away on slot machines and alcohol! You're both liable to lose it all, get drunk, and find yourselves 'knocked up' by some irresponsible jackasses! If she's so 'depressed', go over there and find an alternative way to cheer her up. You don't need to blow a shit load of money and get wasted to cheer her up. That is my final word on the matter! Understand me?" he demanded.

"But... ," she started to say.

He interrupted her, saying, "NO, that is my final word! Or is there another reason you need this money so bad as to ask me after you know I've already put my foot down?"

"No, no. Not at all. I just hoped that you would let me do it this one time. I have been good lately," she implored.

"You ask me again and I will take you over my knee! I am the head of this family and you'll continue to be in my hand until I marry you off to the man of my choosing! Now, do you want to continue pressing your luck? You are way overdue for a serious spanking, you know," he scolded her.

"I'm twenty-four fucking years old. This is 21st century America, not ancient Athens! I'm far too old for a spanking from my BROTHER! I just want to spend time with my best friend! Why do you have to be such a male chauvinist... ," she screamed.

"If you say 'pig', I will show you how much of a chauvinist I can be! Feminist slogans are no way of getting money out of me! Like it or not, Dad left me in charge of this family and your money, so get over it! If you want anything, ask me with the right kind of attitude and a legitimate reason, not some silly request and defiance! Now, if you want to continue this conversation, I suggest that you walk up to the main house and talk to me in person without being a smart-ass!" he interrupted her.

"I'm sorry, Anton! I didn't mean to be defiant and rebellious! I'm just somewhat embarrassed at being treated as a child when I'm in my mid-twenties and most of my friends can do as they please. They control their own finances, but I have to depend on my brother's approval. It's just so old-fashioned," she feigned contrition.

"Your friends also get themselves into more trouble than they can handle, especially that Candy! Old-fashioned or not, that's the way we were brought up and that's the way I will remain! I don't approve of the 'modern, feminist' attitude that women have these days. The old ways worked well for Mom. She had a great husband and provider. She never once complained, either! Like it or not, that's the way this family will be, " he stated authoritatively, "Now, come up here for dinner in an hour and a half, and we'll discuss any other requests of yours at that point. Cora will have supper ready at that time."

"Yes, Sir. I'll be up there within ninety minutes. Bye for now," she slammed the phone down when she heard his response.

Damn, how would she get out of trouble now, Doretta thought to herself. She'd just have to tell her brother the truth and face the consequences. She knew that he'd be furious over her deceit, not to mention her waste of money, but he'd be even angrier if he found out what happened through another source. She looked at the clock and realized that forty minutes had passed since she had talked with "Big Ed".

Doretta got ready to go up to the main house. She chose to wear a dress that her brother particularly liked. He was none too fond of pants on women, but he never actually forbade her to wear them. He picked his battles, but in this instance, she resolved to do his bidding. She didn't want to unnecessarily upset him even more than she already had. She knew that he'd be angry enough when he learned the truth. She didn't want to make it worse.

An hour and a half later, Doretta walked from the guesthouse into the main house, letting herself in. She walked nervously toward his den. She could hear him shouting on the phone. She thought that she heard her name in the tail end of the less than pleasant discussion.

"I will take care of Doretta shortly! You will have your money within the hour, Mr. Bancroft!" he hung up the phone furiously.

"That's it! She's done it this time! No more Mr. Nice Guy! If she thinks that I'm tough already, wait until she sees what I have in mind for her," Anton fumed.

"Oh shit!" Doretta thought as she heard him hang up the phone and rant about her.

How had "Big Ed" known her brother? She was in serious trouble now. She should have told him the truth before now. She walked into her brother's office, saying "Hi" as if nothing was the matter.

Anton turned around and looked at her. He was more than furious. She had never seen him this mad! She contemplated turning around and hiding out for a few days until he calmed down to a dull growl. He must have seen what she thought.

"Freeze right there, young lady! I've just gotten off the phone with a 'friend' of yours. I can tell you that things are going to change right now! As of this moment, you will live upstairs and no longer on your own in the guesthouse! All of your spending has been cut off! You will get the spanking of your life after we eat dinner! How could you think to get away with borrowing money from a loan shark? Did your brain quit working or something? I told you the last time you got into trouble that you would not like the outcome!

"Now I find out that not even a month later you did something that reckless. Did you think that I wouldn't find out? Not to mention, you lied to me earlier when you told me that fucking story about wanting money to go gamble with Candy. In fact, you needed it to pay off an earlier gambling debt! That is the precise reason I don't like you gambling. That is why I don't trust you, Doretta. You're too immature to run your own life. Basically, you are grounded for now. You will live under a man's control from this moment forward," he yelled at her.

Doretta was at a loss for words. He even found out that she had broken her word within the month of her promising not to get into trouble again. She turned around and started to run for the door, but he was quicker and stopped her in her tracks!

"Where do you think that you're going? Shall we begin the paddling now? I'll make sure that you won't be able to sit down at the dining table. Think of how the servants will view that? Of course, they will hear your cries later, when you're in my suite getting your punishment! They won't come to your rescue, though, no matter what happens! They are loyal help and come from a long line of servants, back as far as our great-great grandparents, before Mom and Dad arrived in America. Now, I believe that Cora has dinner waiting for us. I don't like eating a cold supper," he announced.

"Yes, Sir," she gulped hard.

Anton took his sister's arm and led her to the dinning room. Just as he said, Cora had dinner waiting on them. He put his sister at his right side as he sat at the head of the table and Cora served them their food. Doretta sat there and said very little while she ate her dinner. She feared what was to come. What did he mean that she was to be under a man's control now? She wasn't ready to marry. She didn't even have a steady boyfriend. Whom did he have in mind? She was also afraid of his paddling her. Would he spank her bare bottom like her Dad always insisted on, or would he do it over her dress and panties? Damn, she thought, she should have put on a regular pair of panties, not the thongs that she wore. If he decided that she was to be bare, what would he say about her thongs and the fact that she shaved? She shuddered at that thought, but was jolted out of it by his next statement.

"Since it appears that you're no longer hungry, we shall adjourn to my suite. Cora, that was a very delicious dinner you made. My sister doesn't seem to be very hungry, as she is about to be punished severely for a few mistakes she has made. Can you please have all of her things packed and brought up from the guesthouse? She will now use our mother's sitting room and bedroom, connected to my master suite," Anton informed Cora.

"Yes, Sir!" Cora replied, not at all surprised at what went on.

She'd heard the previous master discipline his wife. Cora's mother told her that was how this family handled their wives' disobedience and wrongdoings. It was about time, she thought to herself. That girl needed a serious spanking for a long time now.

Anton led Doretta up to their parents' suite, into which he had moved after their untimely deaths.

"I'm glad that you chose to wear a dress, though, of course, it will be removed for your bare-bottom spanking. You will like the changes I made to Dad's old study. I even enlarged it, taking out the nearest bedroom. I haven't had the opportunity to use it since the renovation. Tonight is the perfect moment to put it to use," he laughed wickedly at his hidden meaning.

"What kind of changes did you make? Why do you have to spank me on my bare bottom? Can't I just wear my dress? I'm sure it's not proper for me to be nude in my brother's presence. What would Dad and Mom say?" she rambled nervously.

"Concerning the changes, you will soon see them for yourself. As for the bare-bottom spanking, that is the 'proper' way to do a spanking, period. Regarding the nudity issue, I am the master of this house. Like Dad during his reign saw you naked, so will I. I want to make sure that you don't have any silly piercings or tattoos that you might have hidden from me. About what our parents would say, they wouldn't have a problem with you getting your bare ass whipped," he firmly replied.

At this point, Anton reached the master suite. He led her through the sitting room into his new and improved study. She was, to put it mildly, "taken aback" by the changes she saw. It appeared that her brother was heavily into the BDSM scene. Why, it looked like a torture chamber in there! Their father's old desk and couch were gone. In their place was what appeared to be a spanking bench, similar to what she saw in her Internet surfing one time. It had a small table near it. She had a good idea that it was there for him to lay his instruments of torture on it, while the victim was prepared or punished.

The walls were lined with paddles, whips, and floggers of all shapes and sizes. There was a metal table set against one wall that had various handcuffs, chains, butt plugs, dildos, and vibrators on it. She also spotted what appeared to be a collar of some sort. There were also bolts mounted to the ceiling and on the floor. He stood there and watched her take in the new look of his study.

There was also a large "spreader bar" which allowed the master to place the victim in such a way as to restrain and spread a person's legs for any reason. The biggest shock of all, in the middle of the room, was a large bondage bench that enabled a victim to be bound to it in any position that the sadist wished.

"What do you think of my remodeling? Now, do you see my spanking bench? You will soon be turned over it and strapped in it. First, however, we need to remove all of your clothes. I suggest you do it now, or I will do it for you!" Anton warned her.

"I ... Uh ... When did you do all of this? I didn't know that you're into the BDSM scene. What are you planning on doing to me?" she stalled.

"Enough stalling! Get those clothes off now!" he reiterated.

Doretta quickly removed her dress, while her brother watched with hidden but growing excitement. Once the dress was off, she hesitated to remove her undergarments.

"The panties and bra too, Sis," he instructed.

Doretta removed her bra first, revealing her massive tits, and then slowly removed her thong, unaware of the fact that she turned her brother on more by doing so. How long had he wanted her in such a position? It had been far too long and he finally had her there. He wouldn't let her get away from him, either!

This was Anton's major reason for chasing off the other men. No other man would steal what rightfully belonged to him. He planned this for several years, seeking what society denied him by its taboos. He was a different kind of rebel from his sister, but he was less orthodox than he first appeared.

As Anton had remodeled the room and bought everything in it, he pictured Doretta on or in every piece of furniture. He imagined every toy being used on her. Every whip, paddle, and flogger he handpicked to train his sister into the proper role Nature had assigned her. While he planned to correct her misbehavior, he wouldn't damage or maim her perfect olive skin. He was stunned after she removed her underwear to discover that his virgin sister shaved her pussy bald.

Anton watched his younger sister stand in front of him, naked as the day she was born. He was pleased to see that she had no piercing or tattoos on her smooth flesh. He instructed her to remain still, hands down by her side, as he circled her and inspected her entire body. He ran his hand over her bottom, which would soon be red from a serious assault with a whip.

Doretta didn't seem to realize the severe danger that she brought upon herself by going to low-life scumbag like "Big Ed" Bancroft to borrow money. The loan shark was notorious for collecting debts from women in the form of brutal rape and sodomy. She was lucky that "Big Ed" wanted his money more than he wanted sex this time. In this situation, the loan shark knew how to get what he really wanted.

Anton also made it clear that he'd better leave Doretta completely alone in the future, neither lending nor "collecting" any other loans. He was determined to inform his dear "Sis" of the truth behind the gangster's vague threats. He had found out the ugly facts about Bancroft after his friend's girlfriend had been raped for failure to pay up. He remembered the man's name after the frightened woman told her beau and refused to go to the police about it. That was when Anton especially started cracking on his sister's gambling habits and became even more protective of her in general. There were too many "Bancrofts" in the world, looking for easy victims like his sister and his buddy's girlfriend.

He suddenly smacked her bare ass with his hands, repeating the action twice.

"Why do you need to shave your pussy or wear thongs, Doretta? You're a fucking virgin, for God's sake. At least, you'd better be! I want to be the one to take your cherries! You're my sister and you will remain mine! You'll be under my control! As I said before, I'm the head of the house and I will remain the head of everything in it. That includes you, my dear sister," he shocked her.

"Everybody does it! Candy does it all of the time! She says it turns men on!" Doretta protested with mock innocence.

"Well, your friendship with 'Candy' is over. You must behave like a true lady, not a tramp like Candy! Anyway, if Candy stuck a needle in her veins and shot herself up with smack, would you?" he responded.

"No, of course I wouldn't! Besides, Candy is my best friend and she doesn't get me into trouble! I do what I want to do! Candy is not a tramp! She just likes men. You have no right to pick my friends, anyway! I'm a grown woman!" she retorted.

"I have every right to choose your friends! I am the master of the house. I control your finances. Dad intended that I be in charge of you, just as he was in charge of Mom. Moreover, Candy is a tramp! She doesn't just like men. She likes every man she has ever seen! That will be the end of this discussion! Understood?" he demanded.

Anton grabbed Doretta's arm and led her over to the spanking bench. He bound her to it, spread her legs apart, bent her over it, and secured her arms into place. This left her ass and pussy open to his assault. He walked in front so she could see him and disrobed himself swiftly. As he removed his pants, his hard, well-endowed cock jumped out into her view, stunning her at its sheer size and stiffness. He was quite aroused at what would happen to her.

"After the whipping, your throat will be the first hole that I take. You'd better not resist or harm me in any way, shape, or form. If you do, the next hole will be taken roughly and without any lube!" he ordered her.

Anton walked to the wall in front of her, where he kept all of his paddles, whips, and floggers. He selected a whip that would hurt like hell without causing any permanent harm. He also chose a "pussy" whip to use.

"For this offense, you'll receive your punishment with a whip, not a paddle. Because the seriousness of your actions could have possibly cost you your life, health, and safety, a whip is in order here. Most of your minor corrections will use either my hand or a paddle. Penalties that are more serious will require a whip or strap. Floggers and canes will be used for outright defiance or constant repetition of a lesser infraction. I'd better not have to use either on you very often, if at all," he forewarned her.

He walked behind her with the two whips he had picked out. He laid the smaller one down on the table near him and raised his arm to begin her spanking.

"You'll receive fifty strokes from each whip. That will be one whip on your ass and the other on your pussy. I know you may think that this is a harsh punishment, but it is necessary to teach you the consequences of what could have happened to you! After each swat, you will count and ask for the next one saying, 'One, Master. Thank you. Can I have the next one please?' You will do this so that you don't 'tune out' the spanking. You will have to pay attention to what is going on," he directed her.

Anton lowered his arm with force, striking both ass cheeks at once. Doretta was unprepared for the force with which it hit her, so she cried out. After this, she counted as he instructed her. After the tenth swat, she had a hard time counting, but she continued for fear that it would get worse if she didn't. By the time that the fifty swats were over, she sobbed hard and begged for his forgiveness.

"I'll never do something so stupid again! I'm sorry! I'll be good from now on! Please, no more! I can't take any more! Don't whip my pussy!" she sobbed.

"You can take it and will take more!" he insisted.

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