Zork2006

The Lady's Club

Background

To fulfill one of her lifelong fantasies, Deb organizes a club for women who are interested in using a Little Boy for their personal pleasure. She gets various takers almost immediately. Each woman has her own particular reason for wanting to belong to the club, but except for Deb, none have any prior experience in this area.

After being caught by Deb, Tommy was sent home and has been waiting for several weeks for what is to happen next. Deb told him she would call for him when she is ready.

Characters

• Favorite punishment: The milking post
• Favorite humiliation: Toilet training

• Favorite punishment: Severe caning
• Favorite humiliation: Little Boy pleading combined with crying

• Favorite punishment: The milking box
• Favorite humiliation: Male body exam & bodily function observation

• Favorite punishment: The punishment chair
• Favorite humiliation: Making the Little Boy eat nasty stuff

• Favorite punishment: Washing out mouth with soap and penis caning
• Favorite humiliation: Forcing Little Boy to present this previous in public

• Favorite Punishment: Electrical shock
• Favorite Humiliation: Forcing the Little Boy to fuck a rubber doll for points

Chapter 1

Opening Scene

When Tommy arrives, he notices that several cars are parked in the area. He is not sure why since it is a workday. He knocks on the door and waits. Deb opens the door and gestures for him to enter. He can hear voices, apparently all female, coming from the room off to his right. Deb walks ahead into the room and tells Tommy to follow with a short and snappy 'come'.

As Tommy enters the room, he is shocked to see six women, all of whom he has met before in various forums, sitting in a circle, having drinks and talking amongst each other. The room falls silent upon his entry. Deb takes her seat and says: "Go the middle of the room, take off your clothes, (all of them) and kneel on the floor facing me."

Tommy is stunned. First off, he did not expect to see anyone else here other then Deb, especially not ladies he knows. Secondly, he is being asked to strip in front of them without explanation or introduction. Rather then object, however, he decides to do as he is told because he really doesn't even know what to say. He can see a wooden square board on the floor in the center of the room. Each corner of the board has a metal loop attached. He can only wonder what its use is. He enters the circle of ladies and begins to remove his clothing. First he takes off his shirt and drops it on the floor.

"Fold it neatly and do the same will all of the rest of your stuff," Deb commands.

Tommy quickly picks up his t-shirt and folds it. Next he takes off his shorts and places them folded on top of the t-shirt. He can hear a few giggles coming from one or two of the ladies. Next he tosses off his flip flops and places them neatly next to the other clothes.

"You were not supposed to wear any underwear, you idiot" says Deb.

Tommy had not even considered this when dressing. He just naturally put them on. "I didn't even think 3;"

"Shut the hell up, you worthless piece of trash," interrupted Deb. "You are only to talk when given permission to answer. Otherwise, never. That makes two demerits for you so far. One for the underwear and one for the speaking."

Tommy instinctively shrinks together after hearing this. He has no idea what a demerit is, but can guess that it isn't a good thing.

"Now take off those nasty shorts and let's get on with it."

Tommy feels very humiliated and is hesitant to take off the shorts.

"What are you waiting for? My God, don't tell me you're being shy!" Deb laughs and so do several other ladies. "If you think this part is embarrassing, you are in for the surprise of your life!" Again, several ladies laugh.

Tommy takes off his shorts and places them on the stack of clothing. There is a mutter of giggly conversation around the room which makes Tommy blush. "Bring you stuff over here to me" says Deb.

Tommy picks up the clothing and starts walking toward Deb.

"You're not to walk upright in our presence unless we give you permission! On your knees, NOW!" Deb commanded.

Tommy drops to his knees and hobbles over to Deb to present his clothing. She takes his stuff and hands him a collar that looks like a dog collar.

"Put this on and get back to the center of the room."

Tommy, walking on his knees, makes his way back to the center of the room. He gets on top of the board and fastened his collar around his neck.

The Rules

"Meet the ladies of the club" Deb continues. "So far we have six members including myself. I expect we will add more over time. I think you know most of the ladies here, but just in case, let me introduce you." Starting at her right, Deb introduces the ladies by adding 'Mistress' to each of their first names.

"Each member has seen your 'pictures of shame' and anyone of them can tell your story to the community. We are all in this together and you only have two choices: to obey or to be publicly ruined."

"Your main roll in life when with one of us is to serve. Women are gods and you are as low as an insect. We will use you for our pleasure – each of our pleasures being different. Our one overriding theme, however, will be to train you to be a women-worshiper and to get all of your nasty manly urges and desires under control. This means that you will be punished severely if you dare get an erection in our presence. You will be punished severely if you are dirty, smelly, loud, offensive – in short, anything but humble and subservient. Any acts on your part that are overtly male in nature will be punished. To reinforce this, your name will be 'Little Boy'. That is what we will call you and that is what you will respond to."

"For all of your wrong-doings, you will be issued demerits. At various points throughout the day, and/or at our whim, you will work off your demerits through punishment. We will each individually choose your punishments and will either administer them ourselves or wait until we are gathered together to hand them out. "

"You will keep a log book with you at all times. It will be attached to your collar and will contain notes from one mistress to the next. You are not permitted to view the log book. Your demerits will be noted and your methods of punishment recorded. We may, from time to time, ask you to write into your log book and subsequently read your entries to other mistresses upon request."

"Next time you arrive here or the house of any lady member, you will have this log book with you. Purchase it soon. It should be large enough to make thorough entries but small enough to be attached to your collar without hindering your mobility. I want you to find a book like this and prepare it accordingly so that it can be attached to the collar."

Tommy nodes in agreement but does not say anything. Deb sternly says: "You are to acknowledge a direct order with 'Yes Mistress' or 'Yes Madam' – that is another demerit. Now you're up to three already – good start!"

The ladies laugh and smile at each other as they continue to look Tommy over in his center stage position.

"While we are on the topic" says Deb, let me inform you of your ten basic commandments – listen carefully, I will not repeat them ever again, unless in combination with demerit assignments:

1. "You are never to look any mistress directly in the eye unless she specifically tells you to."

2. "You are to always kneel in a ladies presence and to call any lady 'mistress' unless she tells you otherwise."

3. "You are to always have your collar and log book around your neck in our presence."

4. "When first arriving at a lady's house, you are to kneel, bow and then kiss the tops of her shoes or feet as a greeting. If there are several women in the room, you will go around and kiss all of the feet. "

5. "Your basic position is on your knees with your legs shoulder wide apart, and your hands behind your head. This his how you will always be when in doubt or if no other specific instructions have been given. There will be a whole list of positions you will be taught and expected to get into on command. If, for instance, we tell you to get into your 'listening' position, we want you to put your right thumb into your mouth and your left hand around your dick."

6. "You may never eat, drink, pee, poop, or do anything independently unless you have first been given permission. You may ask for permission by first asking us if you may ask for permission. For example: 'Mistress, may I ask you a question?' or 'Madam, may I speak?'"

7. "When you come across any member lady in public, you will overt your eyes to the ground and bow deeply enough so that you are at or below her height. In public you will always address us as 'Madam'. If you fail to properly acknowledge us when we cross paths in public, you will be given loads of demerits the next time we meet."

8. "While in our presence, nothing may ever enter your body (like food or drink) unless it has first been 'blessed' by a lady. A blessing can be given in many ways. The simplest form would be if a lady merely says – 'you may drink that water, it is blessed.' In my particular case, I will require that a part of me is always attached to anything you consume. So in order to be my blessing, I will likely pre-drink or pre-chew your items for consumption before you can partake. But, it is up to each Lady to decide what a blessing requires."

"No, I will not necessarily pre-chew everything, but I will make sure that there is a part of me in anything he eats or drinks. I will likely spit into his water or mix it with my pee or something. As for food, I might give him grizzle that I don't' want to chew anymore or leftovers that come from my plate – along with some spit. He is to remember at all times that I am the ultimate authority and that nothing goes without me. So I will be very creative."

Becky chimes in and says: "That is sort of nasty to me. I don't want to be spitting into everything all day long. But I like the idea of blessing his food. Does anyone have any other ideas?"

Tommy is literally shacking as he kneels in the center of the room. He can't believe his ears. Here were six Ladies discussing how they would humiliate him anytime he wants to eat or drink something. And there isn't a damned thing he can do about it.

"I think I might just get a squirt bottle that I will mix all sorts of nasty stuff into. I am thinking I might collect my discharge from when I brush my teeth and maybe mix in some bath water, toilet water, and snott. I'll call the concoction 'holy water'," says Taylor.

At this, everyone breaks out laughing. They look over at Tommy who must look so horrified that a few Ladies burst into almost hysterical laughter.

Finally, Lisa ends the laughter by simply saying: "I plan on blessing things as I feel like it at each particular instance." Everyone nods and looks back toward Deb to finish instructing the remaining two commandments.

9. "You are never allowed to have an orgasm without permission. This means even when you are NOT with us and alone in your personal space. If you masturbate when you are alone, you might think that we can't find out, but I assure you, we have our ways. Each time you arrive for duty at any club member's calling, you will be asked if you have masturbated since you were last given permission. This will be your one and only opportunity to come clean, so to speak. If you confess you will be given demerits and punished accordingly. If you lie, however, and we figure it out, you will be so severally punished that you will regret the day you first found your penis between your legs. There are many ways women can tell if a male has been masturbating. I won't fill you in on the details, but believe me, we can."

The final commandment is this:

10. Before each visit with one of us, you will have thought of and written down a new and humiliating punishment that we can use on you. You will be asked to present your idea to the Madam you are serving at the beginning of your duty. If she likes it, you are safe from demerits and you will be allowed to enter the punishment into your log book. If she does not like it, in other words if it is too light or too easy, then you will be given demerits and punished harshly."

"Yes Mistress," says Tommy with a serious frog in this throat. He feels light-headed and can't seem to concentrate. Hearing all this just forces the reality of his situation to truly sink in. For a moment he contemplates just telling Deb and the Ladies to fuck off and risk the consequences, but his fear of what might happen if the pictures of him get into the public is just too much for him to overcome.

The First Taste of Servitude

"Ok, let's all gather around in a semi-circle so we have a good view," says Deb. "Little Boy, you are going to get your first lesson in following orders and in a technique we will call 'milking'. Put your right thumb in your mouth and suck on it." Tommy does what he is told. "Now with your left hand, I want you to do what you were doing in that video bought in the porn store. I want you to wack-off until you come."

Tommy takes his thumb out of his mouth and says: "WHAT?"

Deb pounds her hand on her chair arm and loudly says: "Did I give you permission to take your thumb out of your mouth? – Did I give you permission to speak?" Tommy quickly reinserts the thumb and shakes his head to signify no. Deb continues: "That is another two demerits. Now start stroking before I add more!"

Tommy is mortified. This has got to be the most humiliating thing he has ever even imagined. Kneeling in front of six women, naked, sucking his thumb and masturbating. This must be a nightmare. There is no way this is happening.

Tommy's penis stays limp for the first several minutes. The ladies watch intently as Tommy struggles. Some of them whisper to one-another and point at him as he continues on in this impossible predicament.

Then Deb says: "Let's make it a little more interesting. I want you to also cry. Yes, cry. Sobbing would be good, but we will take whatever you can give. But here is the catch, you will be graded on your performance after you're done. So make it good! Start NOW."

Just when he thought it could not get any worse, it did. How was he supposed to cry? He started whimpering in a fake sort of way and could tell instantly from the Ladies reaction that he was not succeeding. He closed his eyes and tried to picture himself in his current position and the things that might happen to him going forward and was able to squeeze out a few tears after a short while. The Ladies showed giddy appreciation for this and some actually clapped.

After about five minutes of sucking, stroking and crying, (it felt like at least a year to Tommy), Tommy could feel that an orgasm might be coming near. He didn't know what to do. He had never cum in front of a group of women before. But at this point he was so far gone, he just went with it. His body jerked forward a few times as several drops of cum ran through his fingers and hit the ground. He let go of his penis and the rest of the milky substance splattered on the ground.

The ladies fell silent as they watched intently at what was happening.

"Wow, nasty!," says Taylor.

"That is so weird!," exclaims Becky.

Deb stands up and walks over next to Tommy who is now just kneeling limply with some cum dripping from his dick. He looks spent.

"You have done what you were asked to, but of course, in the process, disobeyed several rules. – Who can tell me what the Little Boy did wrong?" she asks the group.

Sarah says: "He came without permission."

"Yes, that is one thing" says Deb."

"He had an erection without permission" says Becky.

"Correct" says Deb.

"He just took his thumb out of his mouth and is no longer stroking – we never gave him permission for that, either" says Rachel.

"Very good" says Deb.

Tommy quickly reinserts his thumb and grabs his dick.

"Too late Little Boy" says Deb. "That adds four more demerits to your already accumulated four. What you just did, is called 'milking'. We will milk you as we see fit. Since we want you to learn to control this most nastiest of all male urges, the milking process will never be enjoyable for you – even though it might be for us."

There is general laughter around the room. "Milking will always be associated with humiliation, pain, or both. Sometimes you will milk yourself, and other times we may do it for you. Be prepared to be milked often when in our presence – particularly if you show an offensive male trait of any kind."

"Since you managed to squeeze out a few tears and made it look relatively convincing, I suggest we don't add any more demerits for bad performance. Does everyone agree?" The ladies all shock their heads signifying agreement.

Punishment

"Here is the process. You will go to each Lady individually, and repent for your sins and receive your punishment. You will do this by saying: 'Forgive me for I have sinned – please punish me accordingly.' You will then bend over and present your backside to the lady. She will give you eight stokes in any manner she sees fit. She may also force you to endure other indignities in the process – it is complete up to her. Once she is done, you will thank her for punishing you, and move on to the next lady. Is this clear?"

Tommy is as close to fainting as he has ever been. He can't believe this is happening. The nightmare is not ending and only getting worse. He struggles to say "Yes Madam," but almost sounds like he is crying as it comes out. The Ladies laugh at the sound of his voice. They realize that he is scared out of his mind.

Deb gets into her position and says "You start with me. Come over here and ask for forgiveness."

Tommy crawls over to where Deb is standing and kneels in front of her. He is looking at her knees when he monotonously utters: "Forgive me for I have sinned, please punish me accordingly," and waits for a response. Deb says, "you will be punished," and proceeds to spit on the floor in front of him. "Bend down and lick that up as you present me your backside," she says.

The other ladies gasp in surprise and shock at this added humiliation. Taylor is heard saying "Cool."

Tommy is so resigned to his fate, he does not even question the command – he just bends over and begins to lick the spit off the floor. Almost immediately he feels the first stroke hit his ass. It hurts like hell. He yelps in pain. "Silence!" orders Deb and continues to administer the strokes.

With each increment, the strokes hurt a little less but the pain, burning and throbbing all over his ass was still excruciating. After all eight strokes, Tommy rises and says: "Thank you for my punishment." There are tears in his eyes and Deb gives off a satisfied "You're welcome" in response.

The ladies are still standing in a circle around him, so he crawls over to his right to the next lady in the circle – Rachel. He kneels in front of her and says: "Forgive me for I have sinned – please punish me accordingly," and awaits his instructions.

Rachel says: "Hold out your hands to me."

Tommy is confused but does as he is told. He holds up his hands with his palms facing down.

"No, palms up," says Rachel.

Tommy turns his hands slowly wondering what is to come. Rachel lowers her head and spits right into the middle of Tommy's outstretched hands. "I want you to snort that up your nose, Little Boy," she says.

Tommy gasps as do a few of the other ladies. Deb says, "excellent idea, I'll have to remember that one." Taylor also chimes in again saying: "Wow, the possibilities are just mind-blowing."

Tommy lowers his hands toward his face and looks at the spit wad. Still numb to his surrounding and at the breaking point, Tommy presses his nose into his palms and inhales quickly through his nose. The spit gets sucked in and he momentarily feels an urge to gag but quickly regains control knowing that a reaction like that would probably be very dangerous. After snorting Rachel's spit, Tommy bends over and receives his eight strokes from her. Rachel hits harder then Deb did, probably because she is larger and stronger. Tommy's ass is raw and if he didn't know any better he would be willing to bet that he was bleeding slightly. After Rachel completes the eighth stroke, Tommy raises and thanks her for his punishment. His voice is quivering and the tears in his eyes are clearly visible to everyone.

Tommy moves on, very slowly, to the next lady in the circle. This time it's Becky's turn. He kneels in front of her and asks for forgiveness as before. Becky says: "I don't want you to have any of my spit – that is too personal. I also don't want to punish you're rear end – it seems like it's already gotten plenty. I want you to lean back and grab your ankle with one hand and hold out your penis with the other. Hold is out as far as you can and pull back your foreskin. Tommy wobbled as he tried to get into the position he was ordered to. Finally he found a stable place and braced himself for what was coming. Becky took aim and hit Tommy's penis tip squarely. He shrieked in pain and fell over on his side. He cried out loud and begged Becky not to do that again. "Please Mistress, please don't do that again. I can't stand the pain."

"Get back into position Little Boy and shut up," said Becky calmly. Tommy struggled to gain his composure. As he tried to find a stable position again, Becky said, "You need to learn that this thing you like to use for pleasure is not your's anymore. It is ours. Right now, it's mine. And I will do with it what I please. Plus, you need to learn that masturbating and cumming are bad things and that when you do them, you will feel the pain in the source of the pleasure. She again hit down toward his penis but this time hit his hand. The pain was still extreme, but nothing like the penis tip. "I will let that count. If I can't aim, that is my problem," says Becky. The next six strokes were a little lighter in force and hit both is hand and his dick. Becky must have eased off a bit after the first hit given his reaction. When all eight strokes were given, Tommy, crying intensely now, thanked Becky for his punishment and crawled to the next lady in the circle.

It was Taylor's turn. He didn't know what she would think up next but he really didn't think he would last much longer. He was dizzy and felt nauseous from pain and humiliation. He hoped that he would just pass out and be done with it.

Tommy kneeled in front of Taylor and uttered his forgiveness phrase. Taylor was grinning evilly down toward Tommy and took great pleasure and telling him what she wanted him to do. "Here is what I want from you, in addition to your strokes." She bent over and took off her panties from underneath her dress. She said "watch this" and took her panties toward her mouth, spit a huge wad of spit into the crotch area, rubbed the fabric together as if it were detergent and lowered the panties down toward Tommy. "I want you to suck on this while I beat you. I want the crotch to be clean when I'm done or else I might continue on. She shoved the panties into Tommy's mouth and he proceeded to suck furiously while bending over to receive his strokes. Taylor did not target Tommy's ass, instead going for his thighs. The pain was enormous. Tommy sobbed as he was sucking away. After the eighth stoke, Taylor ordered him to get up and show her the panties. She pulled the cloth out of his mouth, examined it and said, "Good job! Now I know one of the things you will be useful for to me."

Tommy thanks Taylor for his punishment and proceeded to the next lady. It was going to be Lisa next. The repentance phrase was uttered and Lisa said: "tilt your head back and open wide." Tommy did what he was told and saw Lisa bend down ready to deliver spit into his mouth. Tommy involuntarily made eye contact at this very moment and Lisa backed off, slapped his face and yelled at him, "don't you dare look me in the eye Little Boy!"

Tommy pleaded instantly that he was sorry and that he didn't mean it but Lisa just said, "I will add two strokes for that. Now lean back again." She spit into his mouth three times. Then she told him to keep his mouth open and to bend backwards and grab his ankles. She said, "don't swallow that spit until I tell you or else I will add more."

As he bent backward, his mouth wide open, he wondered where she was going to hit him. He soon found out when the first stroke hit his upper thigh. He cried out in pain, but managed to keep his mouth open. A few of the ten strokes hit his stomach too. He almost swallowed after one of the strokes but managed to keep it together. The spit was pooling in the back of his throat and he felt revolted at the thought of what was back there. After all ten strokes, Lisa said, "Ok, swallow" and Tommy did with a slight shudder that thankfully no one saw. Tommy thanked Lisa for his punishment and moved on to the sixth and final Lady.

Sarah was last and was obviously ready. After the forgiveness phrase, she bent over, spat on the floor numerous times and then pointed to her creation saying, "You will rub your face in that while I punish you. I want the floor to be dry by the time I am done."

Tommy bent over and started rubbing his face his Sarah's spit pool. She, in turn began caning the last part of his backside that had so far escaped punishment – his calves and feet. Pain was no longer an object. Tommy was so close to the end, all he could do was finish and survive. When all eight strokes were done, Tommy got up and thanked Sarah for his punishment.

Deb ordered him back to the center of the room and the Ladies took their seats.

As Tommy kneeled there in the center, his entire body ached and he could feel the dried spit of all of the ladies on and around his face. His dick was almost completely shriveled in size and he felt like he was about to die.

Deb looked at him and said: "This is your life now. Today we went easy on you because it was your first day. In the future we will be more demanding and more sever in our correction. Learn quickly, for your own good. Before we end today, you will be given your first assignment to serve a Lady in private. We have agreed already on your rotation schedule and your first Lady assignment will be Sarah. Once you have finished serving her, she will tell you who is next and when you are to report to her. Sarah expects you on Sunday morning at ten AM at her house. Go over to her now for the address and some initial instructions."

Tommy crawled over to Sarah's chair and is given a piece of paper. Sarah says: "Read this later, it has my address and a few other things I want you to prepare for. In addition, I want this," she pointed toward his groin area, "clean of hair. It looks too manly. Get rid of it." She then pointed back toward the middle of the room and said "GO."

Tommy dragged himself back to the center. Deb continued: "That concludes the activities for today. You will now take off your collar and receive your street clothing back from me. Remember all of these steps. If you miss one, there will be demerits!"

Tommy took his clothing and was told to leave the room to dress and then to leave the building. As he exited the room, the Ladies erupted into laughter and applause. They sounded like a bunch of sorority girls after going to a formal. They talked, cheered and recounted the events. The sounds of the celebrating ladies died off as Tommy left the house.

Chapter 2

Before the first duty call

Tommy is out shopping for his book at the local Target and deeply engrossed in trying to find the perfect size and shape. All of a sudden he hears a voice say to him "Wow, so you didn't waist anytime getting your log book. I am impressed. We must have made quit an impression on you."

Tommy freezes. He knows the voice and spins around to find Becky standing next to him with her shopping cart. He quickly averts his eyes to the ground and bows down as low as possible without drawing unwanted attention to himself from other shoppers. He whispers: "Hello Mistress Becky."

Becky grins and says "Hello Little Boy. Carry on. Don't let me disturb you," and she walks away.

Tommy is trembling after he is alone again. He quickly tries to review the encounter in his head to see if he missed any detail that might earn him demerits. He can't think of any, but he also knows that he may not be all that familiar yet with their requirements. He can't believe how quickly these women have transformed him into a subservient person.

After this dangerous encounter, Tommy quickly heads for the checkout with his book. He rushes home and begins to work on modifying the book so that it can be attached to the collar. When he is done, we puts on the collar and log book to make sure it all works together. It's not perfect, but it will surely do.

On Saturday evening, Tommy pulls out the paper that Sarah gave him. On it, she lists her address, phone number and a few instructions.

1. Be on time!
2. Be clean – inside and out
3. Have the collar on before you knock on my door
4. Fall to your knees as soon as you enter the door

Saturday night, Tommy could not sleep all night. He tossed and turned wondering what would happen to him. How long would she keep him. How badly would she punish him. What nasty humiliating things had she thought of.

Sunday morning Tommy got up and took a shower. He cleaned himself like he hadn't ever before. He washed his ass intensely and even poked his finger up his butt a little, just in case. He brushed, flossed, did the mouthwash and put on deodorant. When he was confident in his appearance, he headed toward Sarah's house. She lived close by, as did all the ladies, so he was there in a few minutes.

He parked his bike outside her duplex and walked to the front door. He looked around for a sign of onlookers and when he was relatively sure there weren't any, he put on his collar and knocked on the door.

Duty with Sarah

"You remembered," says Sarah, "Isn't that sweet. And you're wearing your collar with your book and you're on time. Maybe we can make a useful member of the male species out of you after all."

Sarah walks off in the direction of the basement door and gestures for Tommy to follow her. Remembering that he is not allowed to walk upright, he follows her in a half crawl, half squat combination. He makes it all the way down the stairs, still dutifully following Sarah, when she turns and orders him to "strip and kneel in the center of the room." Once again remembering the process from the last encounter, Tommy takes off his clothes, folds them neatly and presents them to Sarah who is now seated on an old sofa along the wall of the basement. As in Deb's house, the center of the room has a square wooden board with four hooks on each corner already set in place. Tommy crawls over to the board and takes his place getting into his 'basic' position as instructed by Deb.

"Well done," says Sarah with a slight giggle. "You must really not want to get punished again. Amazing what a little discipline can do for a Little Boy."

Sarah scans Tommy's naked body from her seat and says: "Nice work on the hair removal. I think I want you to maybe go a little further for me next time. Your front is still too hairy and so is your rear, now that I think about it. So just get rid of all of it for me."

"Yes Mistress" says Tommy, thinking to himself how he will look hairless and how he can explain this to his friends.

"Ok, so here we are," says Sarah. "I guess you are wondering what will happen to you now. Well let me break it down for you. You are here for two reasons. First to serve me in anyway I desire and second to be trained to be a Little Boy that can control his undesirable male urges and can treat a lady with respect, honor, and complete devotion."

"I joined the Lady's Club because I have always despised boys who are like you. Dirty, nasty, macho, egomaniacs that will do or say anything to get laid. Also, I have a sadistic side to me. I like to see boys squirm – either in pain or while being humiliated. So there you have it."

"Let's start by getting the formal stuff out of the way. Did you masturbate without permission since we've last seen you?" she quickly fires this question at him.

Tommy instantly remembers the rule she is referring to. Lucky for him, masturbation is the furthest thing from his mind over the past few days. "No Madam," he says truthfully. Sarah glares at him intently and follows-up: "Are you sure that is your answer?" Even though Tommy is telling the truth, he is suddenly worried that she knows something he does not. But feeling completely innocent, he reaffirms his initial answer. "Yes, Mistress."

"Why not?" she simply asks. Tommy is perplexed, but answers: "Well, for one, I have been in too much pain to use my thing down there, and also, I have not really been in the mood since the last meeting."

Sarah laughs, "Well, that makes sense to me. I believe you."

Sarah continues: "Second question – what punishment did you think-up for me?"

Tommy is totally thrown for a loop. He forgot about this part of the instructions. He was supposed to think of a punishment that would suite the Mistresses. He feels the blood rush to his head.

On the fly he makes up something: "I thought of being made to masturbate in front of you and forced to lick-up my own cum," he finally says.

"That's it?" Sarah responds. "That's totally boring. What the hell am I supposed to do with that? Ten demerits for your piss poor answer. In the future, I would do more thinking on this subject. Use the internet for inspiration if you can't use your own imagination."

"Ok, now it's time we get to business – my business! Come over here to me and bring me that box from the corner."

Tommy crawls over to the corner, retrieves a plain cardboard box from the floor and makes his way to where Sarah is seated. He puts down the box and stands at attention. Sarah opens the box and fumbles around inside for a moment and pulls out a light blue t-shirt, obviously sized for a child. She turns it around and shows Tommy what is says: Baby on Board'. "Here put this on," she says and hands Tommy the t-shirt. Tommy has no illusions that this will fit, but does what he is told. He pulls the t-shirt over his head and forces his arms through the sides. With great effort he manages to get on the shirt but even after pull as hard as he can, it only reaches down to his navel.

"Excellent!" says Sarah. Next she pulls out a can of Vaseline from the box and says: "Put this in your hair and slick you hair all the way back." Again Tommy does as instructed. He takes two fingers and gathers a big wad of grease and proceeds to rub it into his hair. She hands him a comb so he can finish the style. Sarah gives Tommy an appraising once over and again goes for the contents of the box. She pulls out a red ribbon and holds it out to him. "Tie this around your penis and balls – like a little present," she says. As Tommy gets to work tying his ribbon, she continues inside the box.

"As a last final touch, I want you to put on some lip gloss. Little Boys have shinny lips and a rosy complexion so that is what you'll need, too. Put some on your lips and some on your cheeks."

Tommy dutifully does what is asked. He feels ridiculous. He is wearing tiny t-shirt, has a red bow around his privates and now is wearing lip gloss on his lips and cheeks. Sarah sits back and admires her creation. "Not too bad." She says. "Remember all this well, you will have to recreate it the next time you serve me. Plus, at the end of your duty today, you will need to write everything that happened into your log book. I will check it for completeness and grade you accordingly."

"That brings me to the remaining events of the day. You are mine until I release you. Presumably, this will be sometime later today, but not necessarily. If you don't finish your chores, or if I am just in a bad mood, you might have to stay longer. I will be giving you various assignments throughout the day. For each assignment, you can earn a possible 100 points. To earn a perfect 100, you will need to perform the assignment perfectly. This means that everything has to be exactly like I want it or else you get deductions. For each deduction, you will get a demerit. So if you manage a 'C' average you would get a 70 or, 30 demerits. I recommend you try and get a perfect 100 every time. Do you understand so far?"

"Yes Madam," says Tommy with that familiar frog raising in his throat.

"Your first task is to clean the bathroom down here in the basement." She points to a door off to the side. "It hasn't been cleaned in a while and it is kinda nasty. I will give you a bottle of 409 [cleaner] and five paper towels. You may not use running water and you may not flush the toilet until I tell you. I want you to get the place clean with the 409 and paper towels. Also, I want you to collect each hair that is in there in a neat little pile. If I find a single hair anywhere that is not in the pile, there will be deductions. When you're done, I will come in a grade your performance. If I find a job that is less then a 90, I will not only give you the demerits, but you will be ordered to eat the hair and the paper towels as an additional punishment."

Tommy swallowed hard at this last piece of information. How is he going to clean an entire bathroom with just five paper towels and a bottle of 409? This day was starting off worse then he had feared.

He enters the bathroom equipped with his meager supplies to find a small, relatively poorly lit cellar bathroom. It is indeed in need of a cleaning. The toilet has mildew in the bowl, the shower tub has soap scum and mildew, and the sink is covered in hair and a mixture of various beauty product residue. The floor, which is all tile, is also covered in hair and drippings of the same type found next to the sink.

Tommy starts with the sink. He figures he will use one paper towel for each major fixture and hopes to have one or two remaining as backup if needed. He sprays the 409 in the sink and begins to scrub. Hair clumps together under the towel and he remembers that he is supposed to collect the hair separately. He pulls the hairs from the towel and stacks them on top of the water tank of the toilet. He decides to collect as many hairs from the rest of the room as possible first to make room for the scrubbing. It is a nasty task. There are thousands of hairs all over. He knows he can't allow himself to miss a single hair if he hopes to score a perfect 100, but even worse, we dreads the thought of being made to eat all this hair if we fails the task miserably. He is on his hands and knees looking everywhere for a sign of an illusive hair. The pile on the commode has reached the size of a grapefruit. The hair seems to be a combination from various donors. Some hairs are short, some long, some with a reddish hue (obviously from Sarah) and others blond.

Nearly 45 minutes pass and Tommy is relatively pleased with the state of the bathroom. It would be nice to rinse the fixtures with water to get rid of the 409 residue, but it looks presentable. The biggest remaining potential problem is the mildew in the toilet bowl. That stuff is tough and won't yield to the paper towel. Out of fear and desperation, Tommy uses his fingernails to scratch the stuff off as best he can.

Finally, after about an hour, Tommy thinks he is finished and crawls over to the door to alert his Mistress that he is ready. Sarah is seated on the sofa reading a book and sees Tommy kneeling in the doorway of the bathroom.

"Are you ready?," she asks.

"Yes Madam," says Tommy and starts to feel weak in his knees in anticipation.

"Ok, I will check out your work. It sure did take you long enough," says Sarah.

She walks into the bathroom and makes and initial scan of the room. "Not bad at first sight," she says. Next she inspects the tub closely and nods in approval. Tommy is feeling a little more confident now and starts to hope that maybe a 100 is not impossible to achieve. Sarah moves on to the sink and still has noting to say that would indicate a mistake. She looks down at the toilet and smiles as she says: "I can't believe you got that mildew off. Good job!" Tommy is elated. He can feel the 100 already. She looks at the pile of hair on the water tank and the five used paper towels and once again nods in approval. Just as he starts to feel home free, Sarah opens the vanity drawer that Tommy had totally failed to see. She looks inside and steps back. "What the hell is this? The drawer is still totally filled with hair. Are you out of your mind?" Tommy almost passes out when he realizes what he has done. He missed the drawer completely. Who knows how many hairs are in there. Good God, he is screwed.

Sarah pulls the drawer out completely and starts to drop its contents on the floor one by one. Finally the drawer is empty and all that remains is the hair and various other dusty debris.

She sits down on the commode and says: "Let's count and see how deeply you're in trouble." She starts to pull the hairs out of the drawer one by one. When she reaches nine, Tommy starts to shake because only one more hair will mean the worst case is going to happen. After all is counted, there are exactly 22 hairs in the drawer. Tommy is devastated. That means 22 demerits and a meal made up of hair and other nastiness.

Sarah orders Tommy over to her. "Kneel in front of me she says." Tommy comes over immediately. "What did I tell you would happen if you did not get a least a 90 on this task?"

"Mistress said that I would have to eat the hair and the paper towels, Madam," says Tommy with a shaky voice.

"Yes, that's right. And I hope you're hungry," says Sarah with a grin in her face.

"Open wide!" Sarah takes the pile of hair and rolls it into a tight ball about the size of a golf ball. She shoves it into Tommys month and tells him to chew and swallow. Tommy tries to do as he is told, but the chewing doesn't get him anywhere. It only loosens the ball into a nasty tasting fur ball. She watches him intently as he struggles to get down the hair. Finally he swallows and the clump slowly slides down his throat, although numerous hairs still remain behind and irritate his throat.

"If it makes you feel any better, the hair all came from women," said Sarah as she continues to watch him. Strangely enough, this information does make Tommy feel a little better. The thought that men's hair was included worried and revolted him even more.

Sarah makes Tommy open his mouth to prove that the hair is gone. Once satisfied, she reaches for the paper towels. "Ok, here is desert." She holds up the first paper towel, which is all brown and wet from the cleaning and shoves it into Tommy's mouth. The taste is horrible. It is a combination of soap, perfume, and other unknown tastes. He gags. Sarah holds up her finger and says: "That would be a very bad idea." Tommy does his best to swallow the towel. He gets through the first four and only has one to go. Sarah picks up the last towel and notices that it is still clean and dry. She says: "This will be hard to swallow – let me help you out a little." She proceeds to moisten it with a big spit wad and then places it into Tommys mouth. After having to eat the 409 covered towels, this spit covered one was actually pleasant. To his shock and amazement, he suddenly realizes that he is becoming what the Ladies want him to become. A total women worshipper. The fact that having to eat a spit covered paper towel almost feels like a relief to him is incredible.

Sarah stands up and walks out of the room. "You now have 32 demerits. You will get to work them off later. For now, pick that crap off the floor and put it back into the drawer and then follow me for your next task."

Tommy follows Sarah back into the basement's main room. She points toward center of the room where the square piece of wood is still lying. "Over there," she says. Tommy gets into his standard position and waits anxiously for what's next.

"As your next task, I want you to pre-clean some of my laundry. Mistress Taylor gave me the inspiration for his last week," she says smiling. "I want you to go over to the laundry basket and pick out all of my panties. It is so hard to get the crotch area clean in the wash, so I want you to pre-clean them for me. You may use your mouth and a bar of soap. That is it. It you start to run completely dry, let me know and I will provide you with more moisture, but I think you understand that it won't be water."

Tommy didn't think it would be. He is terrified to think what it might actually be.

"You have twenty minutes to complete this task. I will inspect each panty afterwards and give you a score. Anything less then 100 will add to you demerits. You may start now." Sarah points toward the washing machine and Tommy immediately gets going.

He empties the laundry basket onto the floor and quickly sorts through the clothing to find all of her panties. There are about eight all white panties in the basket as far as he can tell, but he does a second scan just to be sure – he doesn't want to risk another oversight.

Once he is sure that he has the entire set ready, he takes up the first pair of panties and finds the crotch area. There has a slight yellowish discoloration in the crotch that is clearly a contrast to the white panty. He puts the crotch area into his mouth and starts to get the cloth wet by gently chewing on the fabric. He then sucks on the fabric for several seconds in the hopes of extracting the soiled portions.

In the corner of his eye, he can see Sarah sitting on the couch watching him while gently rubbing herself between her legs.

The fact that Sarah is enjoying this so much makes Tommy angry but there is nothing he can do about it. After about a minute or so, he takes the panty out of his mouth to check his progress. To his horror, there is no real change in the color. He realizes he will have to use the soap, too.

He takes the bar of soap that Sarah gave him (Dove) and rubs the soap onto the crotch area. He again puts the panties in this mouth and redoes what he did before. The taste of soap is really unpleasant and he gags several times in the process. Sarah seems to get a real kick out of his gags because he can see her thrusting harder each time he convulses.

Finally, after about two more minutes, he seems to have the first panty clean. He places it aside and starts on the second. This one is much dirtier. It has almost a crusty kind of residue on it and Tommy tries not to think about all of the possible things that could be the cause of the stains.

The cleaning continues on all of the panties and he sort of gets lost in time after the fifth or sixth pair. All of a sudden, Sarah says: "You have five minutes left." Tommy gets a jolt of panic. He has two pair left and he is starting to run very dry in his mouth. The taste of the soap is becoming overwhelming and he could really use some water, but he knows that is not an option. He realizes though, that he has to have some help or else he has no chance of finishing.

"Mistress, may I have some moisture, please?" asks Tommy.

"Yes, you may, but first you get a demerit because you didn't ask if you were allowed to speak." She walks over to him and grabs the top of his hair forcing his head back. "Open up and tell me when," she says. Tommy is too shocked to react and just does what he is told. He opens his mouth and sees Sarah start to collect a large quantity of spit in her mouth. She lets it slide out of her mouth into his. The moisture feels great, but he has to concentrate real hard not to gag. After two more spits, he says "When." And Sarah lets go of his head and returns to her seat.

Tommy just sits there momentarily in shock. He can taste Sarah in his mouth and is complete confused at what just happened. Sarah snaps: "Time is ticking" and wakes Tommy back from his trance.

He frantically continues to suck and chew the remaining panties, aided somewhat by the extra moisture given to him. While working on the last panty crouch, Sarah calls "Time". Tommy takes the fabric from his mouth and gets back into his attention position.

Sarah slowly walks toward the small pile of pre-cleaned panties and says: "I wonder how you did. Let's check it out."

She quickly sorts through her underwear collection tossing some panties to the left and others to the right. After she is done, she stands up in front of Tommy and say: "Remarkably good job overall. I only saw two that did not pass muster. That means two more demerits. Jez, I forget how many we are up to now, do you know?"

Tommy quickly recalls what he can and says: "33?"

Sarah laughs and says: "Nice try. No, actually I was just testing you. You have 35 altogether. But now it's 36 since you tried to pull a fast one on me."

Tommy's face is red with a combination anger and fear. He has spent almost two hours with her so far and she has already given him 36 demerits. Where is this going to end? What else will her sick mind think up for him?

Sarah sits back down and says: "I really don't have anymore tasks worthy of your talents for right now. But I can't let you go yet."

Tommy thinks to himself 'PLEASE let me go. PLEASE.'

"I think first we better work off the demerits you have earned so far. If you get anymore, I will have to work to hard all at once giving you your well earned punishment. Little Boy, I have modified a special chair just for your punishments. I have appropriately named it 'Punishment Chair'. You can find it the closet to the right. Go get it and set it on the wooden square in the middle of the room."

Tommy crawls over to the closet and opens the door. He is horrified at what he sees. Inside there is very small wooden chair, possibly a child's chair, that has been modified with all sorts of hooks and pads attached. It resembles a torture device at first glance, but Tommy can't immediately tell how it will be used. He lifts the chair and tries to move it while crawling, but quickly realizes that this will not work. "Mistress, may I speak?" asks Tommy.

"Yes, you may," she responds.

"May I walk upright in order to move the chair?"

"Yes, you may" responds Sarah.

Tommy gets to his feet, a wonderful feeling having been on his knees for hours now, and lifts the chair. He shuffles over to the wooden board and places the chair in the center.

"Now go and get the plastic bag that is also in the closet," says Sarah. Tommy walks back over to the closet and picks up a heavy plastic bag. He carries it over to the chair and places it down.

"Back on your knees," orders Sarah. She stands up and walks toward him. "I have not tested this devise, so it might require some adjustment. You get to be my guinea pig. I want you sit on the chair and tilt your head back toward the head rest pad."

Tommy does what he is told. Once in position, Sarah pulls out a strap from the bag and ties it around his forehead and loosely connects it to the rear of the chair.

"Now slowly slide you rear end off the seat until your knees hit the ground," she orders.

Tommy is confused by tries to comply. He grabs the seat of the chair and slides his rear off the front feeling for the ground with his knees. The strap on his forehead forces his head even further back into a very uncomfortable position. Once he reaches the ground, Sarah tightly secures his head in place. He is now looking directly toward the ceiling. His legs are on the ground at each side of the chair and his mid-section is being forced painfully forward by the seat bottom of the chair. The overall result is that Tommy is bent backward with his midsection protruding and his face pointing upward.

Sarah attaches his legs to the hooks on the board and ties his arms down to the side of the chair as well. He is completely immobilized. He thinks to himself that he finally understands the purpose of the wooden board. Surprisingly, he is not scared. The surrealness of the situation is such that he has no capacity for fear anymore.

Once Sarah finishes her handy work and checks the security of all the attachments, she stands up over Tommy and says: "Open your mouth as wide as you can." Tommy opens and Sarah inserts a round metal loop about the size of a tennis ball in circumference. The loop wedges inside his mouth and makes it impossible for him to close his mouth.

"Here is what is going to happen," says Sarah. "You will be caned around your midsection, including your penis and balls. While I am doing this, I will also, from time to time, spit into your mouth and onto your face. You will get 36 licks altogether. You may cry if you like, but it won't help."

Tommy is shaking violently. The fear definitely set in once he heard the caning would include his privates. Tears are already welling up in his eyes.

"Sarah bends down and ties his balls together with a rubber band. She uses tape to attach his limp penis to his stomach. Tommy can't help cry out some inaudible tone that sounds like a plea. Sarah giggles and continues on with her task. She walks around the chair and picks up the cane. It is a 48-inch [1.20 m], very thin, bamboo stick. She shows him the cane and says: "Ok, here we go. You get 36, and I will count as we go along."

The first lick hits Tommy's penis head. He convulses in pain and cries out in agony, but he is tied so tightly that he barely moves. Sarah leans over his face and release a long string of spit into his mouth. He feels it hit his tongue and the back of his throat.

"You were a very bad Little Boy so far today," she says with a smile. "You will learn to be more diligent and careful." Again she swings the cane and hits his upper thigh, right under his ball sack. The pain is severe but he can't even imagine what it would feel like if she had hit his balls. The next five strokes are mostly on his stomach and tights. One lick hits his chest. At stroke number 15, she hits the bulls eye – his ball sack. Tommy almost passes out from the pain. He can't breath. He is in total agony. Tears are streaming down his face and he is wailing out load. Sarah drops another big wad of spit into Tommy's mouth. She is totally enjoying this. She says: "Oops. I guess that might have been a little too hard." She snorts her nose and collects a lugy and spits it into his mouth. "Maybe that helps," she says.

Tommy can't believe her cruelty. She is a total sadist. And worst yet, he still has 21 licks remaining. Sarah says: "I am running out of spit, so I need to get this over with." She draws back the cane and rapidly fires ten licks down on him. They hit all over the place, but thankfully miss the ball sack. Again she spits, this time into his face and rubs it around with her fingers. "The last eleven strokes are going to be on your penis head," she says. Brace yourself. Tommy is already so far gone and crying so hard that the announcement barely impacts him. He was very close to unconsciousness.

The pain is surreal from the strokes to the penis. Once she finishes, she drops the cane on the ground and walks away. Tommy continues to cry and convulse from the pain for several minutes. He doesn't know what Sarah is doing. Suddenly he hears her moan like she is having an orgasm. As it turns out she is masturbating herself, reliving what she just did to Tommy. Once done, she get up and walks back to Tommy who has calmed down slightly. She sticks her fingers under his nose and he can smell her womanhood all over them. She reaches down between her legs and collects some of her juice from her wet crotch. She smears her fingers on his face and inside his mouth.

"This is how wet it makes me to punish you. So you see that you will have a real hard time getting off without demerits. You better be perfect in the future."

Tommy continues to whimper as she unties him. He slides to the floor into the fetal position, still gasping for breath.

"You have two minutes to collect yourself and be back in position," says Sarah as she walks back to the couch.

Tommy pulls the metal ring from his mouth and tries to catch his breath. His face is sticky from the spit and pussy juice. All he can smell and taste is Sarah. She has totally taken over all of his senses. His body is a wreck. He hurts seemingly everywhere. Most of all, his dick is burning and throbbing. He sneaks a quick look between his legs and is shocked to see a red, slightly swollen and obviously severely abused penis. He starts the process of getting back to his knees, straightening his greased hair and pulling down his tiny t-shirt.

Sarah says: "Put the chair away. You can walk if you need to. Also put all the straps back into the bag and clean up all of the mess." Tommy quickly does as he is told. The only thing he knows for sure is that he does not want to see that chair again anytime soon.

When he is done cleaning up, he swiftly goes back to the board and kneels at attention. Sarah scans over his nether-regions and says: "Oh my, I certainly seem to have done some damage. I hope nothing permanent. I think I need to check your plumbing."

Tommy can't help but give off a slight whimper.

"Get that bucket from over there," she commands pointing to an old paint bucket in the corner.

Tommy scurries over and retrieves the bucket. "Place it in front of you on the board and urinate inside," she says casually.

This is the first order he is given all day that does not frighten or revolt him. He actually needs to pee and was afraid so far to ask permission. Now he gets to do, albeit in front of her, but there do not seem to be any additional strings attached.

Tommy holds his throbbing penis over the bucket and begins to pee. There is a definite burning feeling associated with the urination but at least it still works.

"Thank goodness," says Sarah, "I was worried." The tone in her voice is obviously sarcastic.

"Now to check the other, much less useful function," she continues. "Whack off into the bucket."

Once again she manages to shock Tommy. Just when he thought things were looking up, wham, another seemingly impossible task.

"Mistress, may I speak?" asks Tommy.

"Speak" says Sarah.

"Mistress, my penis is hurting so bad, I can barely touch it. Also, I am afraid of what might happen if I get an erection in this state. Please don't' make me masturbate."

There are several seconds of silence during which Tommy can tell Sarah is starring directly at him. Then she says: "Here are your options. Either you whack off into the bucket and finish within five minutes or else you go get the chair back out the closet. My spit capacity seems to be back to normal."

Tommy instantly grabs his hurting member and begins to stroke. The pain is excruciating. He grits his teeth in an effort to endure the pain. Unfortunately, there is absolutely no sign of an erection and he only has five minutes to cum.

"A wise choice, if I do say so," giggles Sarah. "Come on, you can do it."

Tommy is stoking with his eyes closed and teeth clenched together. He feels himself leave his body and look down on his pathetic state. He is almost naked, kneeling on a board, wearing a tiny t-shirt with 'Baby on Board' written on it. His hair is greased back and he has lip gloss on his checks. His face is encrusted with spit and vaginal juice. He is whacking off into a bucket filled with his own piss and all this in front of a beautify women who is making him do all this. He feels completely out of control. He feels like he no longer owns his body. He has lost all shame, modesty, ego, and sense of self. He realizes that this is what the Ladies want. This is what his life is supposed to be from now on. With the exception of the times that they will allow him to go home, he will basically be their play thing.

Strangely enough, this realization causes him to suddenly feel a slight erection coming on. He tries to think of the attractive qualities of Sarah. He tries to imagine being allowed to eat her out. The taste of her spit still present in his mouth helps him along even further. All of a sudden he shudders and squirts a long stream of cum into the bucket. He continues milking his now rock hard penis and squeezes out the remaining cum. The pain in his dick is still there, but it's no longer unbearable.

"Just in time," says Sarah. "What were you thinking of in order to make yourself come?" she asks.

"I was thinking of how beautiful Mistress is," replies Tommy.

"Wrong answer," says Sarah forcefully. "You are never to think of me in a sexual way. NEVER. Do you understand?"

"Yes Mistress" whimpers Tommy and almost falls to the ground in an attempt to grovel and avoid punishment.

"That's five demerits. You better keep it under ten for the rest of the day or else the chair will see the light of day again" says Sarah.

Tommy's fear is beyond description. He is pretty sure that he will not survive another stint in the chair.

"You have been with me today for going on four hours. I am tiring of this. I think you have learned some valuable things though. Can you remember all of your lessons?" asks Sarah.

"Yes Ma'am," says Tommy forcefully; trying to convince her with his tone that he learned everything possible.

"Well good," says Sarah, "because you now need to record your day's events in your log-book so that all the other Ladies can see how you're progressing. So here is your assignment. I want you to kneel in front of the coffee table here and write about what happened to you today. I want you to write it as if you were an eight year old. I want you to list the tasks, grading and punishments. When you're done, you will read it to me and I will grade you. I will then add my own comments and then dismiss you. Oh, only of course, after you pay for your demerits that I am sure you will earn. Just be sure not to earn more then four, so that means you need to get a 96 or better on this assignment. Do you understand?"

"Yes Madam," says Tommy weakly.

"Then begin. Here is a pen," Sarah commands.

Tommy crawls over to the coffee table, takes the pen from Sarah and begins to write in his logbook which Sarah places on the table in front of him. He tries his best to remember what an eight year old would write like. He figures short and choppy sentences with simple words. He writes things like: "Mistress found hair in a drawer. She was very mad. She made me eat all the hair. It was gross." and "Mistress tied me to the punishment chair. I was very afraid. She hit me all over with a cane. It hurt so much that I cried. I cried a lot and even screamed."

Twenty-five minutes later, Tommy is finished. He re-reads his writing for errors and then tells Sarah that he is done.

"Great," says Sarah "read it to me. And remember, you are to read it like you wrote it. Like a Little Boy."

Tommy starts to read. He alters his voice somewhat to match the writing style. He starts, "Today I went to go see my Mistress Sarah at her house. She made me wear a very small t-shirt and stuff in my hair 3;"

Sarah starts to laugh hysterically. She laughs through the entire story and actually claps when he is done. "That was fantastic. I have to say, you actually seem to have gotten it. I will give you a perfect 100 for that. Good Little Boy. I must be really good at this."

She takes the book from Tommy, looks over the lines again, chuckling and then adding a few lines of her own. She closes the book, and seals with an old-fashioned string and wax seal.

"Ok, all you need to do now is pay for your ten demerits," she says. "Bend over on the wooden board – put your hands as far in front of you as you can and stick your ass in the air. You will be caned on the rear – much easier then the chair, don't you think?"

"You will count for me this time. 'One, thank you Mistress; two thank you mistress; etc.' Do you understand?"

"Yes Madam," says Tommy, his voice again shaking.

The caning event goes off, albeit painfully, but otherwise event free. Tommy manages to hold back any additional tears. Compared to the punishment chair, the caning is downright tolerable.

Tommy is excited about the prospect of being released. He gets back to his knees and expects Sarah to remove his collar and give him back his clothes. Instead, she walks back over to the closet that contains the punishment chair. She retrieves several straps and returns to face Tommy.

"Get up against that poll with you back to the poll and your feet behind it," she orders. Tommy's heart sinks. He is not done after all. The torment will continue. He does what he is told, however, and positions himself with is back against the metal support poll.

Sarah ties one of the straps around his neck, securing his head to the poll. Next, she ties his feet together behind the poll. Finally, his hands are tied behind the poll as well and he is pretty much completely immobile. She places the bucket filled with his fluids directly in front of him so that his limp dick is halfway hanging inside the bucket.

"I decided it's too early to let you go. I will leave you here to rest and to think about what you have learned. I'll be back in a few hours to check on you. Have fun."

At this, she turns and walks up the basement stair, closing the door to the house behind her.

It is very quiet in the basement and all Tommy can hear are footsteps from above. Sarah obviously went right for the phone because he can hear the muffled sounds of her talking and laughing. His position against the poll is very uncomfortable. His knees are killing him and he has only limited mobility to shift his weight from side to side. On top of that, he is thirsty and hungry, but he would not dream of asking for anything from Sarah. Lord knows what she would brew up.

The fact that Sarah placed the bucket in front of him makes Tommy think that he might be here for a very long time. This realization somewhat leads to panic after about an hour because the pain in his joints is starting to overtake all his senses. He feels so helpless. He IS helpless. Not to mention humiliated.

What was going to be next? Beyond today with Sarah. He has this sinking feeling that Sarah is not even the worst of the six lady members. Deb is who really frightens him. But Taylor and Lisa also seemed way too turned on by his pain and humiliation. Becky and Rachel are probably the two sanest in the bunch, but you never know.

About four hours pass and Tommy hears the basement door open and the footsteps of someone coming down the stairs. To his horror, the footsteps seem to indicate more then one person. He strains to see who is coming and finds Deb following Sarah over to him.

"Look who paid me a visit. It's Mistress Deb. She wants to see how your first day went," says Sarah.

"Hello Mistress Deb," says Tommy as politely as he can. Deb smiles and intently looks over his tied up and bruised body.

"Well done," says Deb to Sarah. "Let's untie him and get him out of here so we can go to dinner."

Tommy's heart leaps at the prospect of being allowed to leave. Sarah quickly unties his restraints and as soon as he is able, Tommy dutifully drops down in front of Deb and kisses her feet in greeting.

The two ladies exchange glances of amazement and Deb gives Sarah a 'high five'. "We are accomplishing our goal much quicker then I thought we would," laughs Deb.

Sarah tells Tommy to go empty the bucket in the toilet, and that he is very lucky he didn't have to drink the contents (this time). When he returns with the empty bucket, Sarah reaches around his neck, takes off the collar and tells Tommy to put on his street clothes.

"Have that t-shirt on underneath your clothes next time we meet," she says. "Now here is your next appointment." Sarah hands Tommy an envelope and with that he is sent up the stairs and out of the house. His day is finally over. Thank God!

Chapter 3

Between Assignments

Having cleaned up and somewhat regain his sanity, Tommy sits on this couch and opens the envelope Sarah handed him. Inside he finds a brief message telling him where and when to report next. It will be Mistress Rachel and she wants to see him on Tuesday evening at 6:00 PM.

Even though this is a school day, he knows he can make the 6:00 PM time. He is also encouraged because he figures that he might get off with a short visit given the lateness of the start time.

The note also tells Tommy to be wearing a pair of tight underwear that has its rear section and fabric around his penis cut away. "The goal is to have your genitals and rear end exposed when the shorts are on." Finally it tells Tommy that he is to be shaved clean around his private parts. This seems to be a common theme among the Ladies, Tommy thinks.

Tommy has two days to prepare for the next appointment with his new fate. He knows he may not masturbate (even though this is the farthest thing from his mind) and he also remembers that he needs to think of a good punishment that he can suggest to Rachel when he arrives. To that end, he takes Sarah's advice and references the Internet.

The next day is relatively uneventful. Tommy stays indoors for most of the time except for when he goes to school. Tuesday, he has a hard time concentrating at school. As the time gets closed he grows more and more nervous. What would she do to him? How long would his torment last? Would he be done in time for school tomorrow? He had never looked forward to seeing his class room again so much.

Duty with Rachel

He knocks on the door and waits anxiously. Rachel opens the door and steps aside for him to enter. Tommy has rehearsed the next several actions many times in his mind. He goes through all the motions that his forced servitude requires: Kneels and kissed Rachel's feet; gets into the attention position and waits for instructions. Like Sarah, Rachel takes Tommy into her basement right away. Once downstairs, she orders him to strip and to kneel at attention. She takes his log book and sits down on a wooden chair she places directly in front of him.

Tommy is kneeling on the floor, with his modified underwear in place. His balls are hanging out of the cut area and his rear is exposed as well. He carefully scans around the basement room. It's a square room about 48 by 24 feet [15 x 7½ m]. The floor is concrete and there are three or four support beams in the center of the room. There is no furniture other then the chair Rachel is sitting on. To the far end of the room, Tommy can see a row of windows and a door to the back yard. There is a lot of clutter in the room, mostly in boxes stacked up against the various walls. Other then that there is nothing noticeable or remarkable about the room – it's just a normal cellar.

For the next few minutes, Rachel reads the entries in the book and chuckles out-load several times. Once she is done, she focuses her attention on Tommy and begins by asking: "Have you masturbated since you left Sarah's house?"

"No Mistress," says Tommy.

"Why don't I believe you?" asks Rachel sternly.

"Mistress, I have been in too much pain since I left Mistress Sarah's house. I can barely touch my privates and I have no interest in masturbating," explains Tommy

"Well, I guess that makes sense to me" chuckles Rachel. "So I choose to believe you. But God help you if I find you are lying."

"Now tell me your thought-up punishment," continues Rachel.

Tommy has prepared for this. He spent hours on the internet looking for a good, humiliating punishment that the Ladies would accept.

"Ma'am, the punishment I thought-up goes like this: If I break a rule then I am made to drag a heavy weight around the room by my balls," Tommy explains.

Rachel thinks for a second and responds: "No, I don't like it. It is not really that tough and it certainly is not humiliating enough."

Tommy's heart sinks. Again he earns ten demerits before even getting started.

"I have a good punishment for you that I am sure you will get to experience, particularly since you already have ten demerits. Once you experience it, you should have a better idea of what I am looking for," says Rachel matter of factly.

"Ok, let's begin," says Rachel getting out of her chair. "You will serve me in two ways today. First and foremost, I need various parts of my house cleaned and you will do it for me. Secondly, I will use you for sex education."

Tommy is confused. What does sex education mean? He doesn't say anything, but his face must give away his confusion.

Rachel continues: "As you might know, I have a 14 year old daughter. I am not sure what level of experience she has with Little Boys – she tells me none – but I want her to be able to learn the basics in a safe and controlled environment. Before you get all excited, you little pervert," says Rachel loudly, "you will not even get close to fucking her, touching her, or seeing her naked or even seeing her at all for that matter. All I am going to use you for is for biology lessons. You are the dummy (in more ways then one)," she chuckles.

"When the time comes, I will have her learn about the male parts and how they work by seeing your restrained body as an example. If you want to be in a world of trouble," Rachel sternly continues, "you will fail to control yourself for even one second while this is going on. I can't begin to tell you the wrath you will feel from me if she is traumatized in the least bit. Do you understand, Little Boy?

"Yes Ma'am," says Tommy weakly. Once again, the worst thing he thought could happen has been far exceeded by reality. The humiliation of a 14 year old girl examining his body for sex ed lessons is almost too much to bear. Plus, he can't imagine that the girl won't tell her girlfriends. Teens can't keep a secret. This is getting seriously out of control.

Tommy has very little time to contemplate his fate because Rachel is clearly ready to get started with his work tasks.

"I have told my daughter that you are serving us and what you did to get put into this situation. I have also told her about the club and the proper role of men in the presence of women. You are not allowed, under any circumstances, to have contact with her while you are working. If you cross her path, immediately leave the room, showing her the same respect you show all Ladies. She is allowed to give you demerits, but she is not allowed to talk to you without me present. You are not allowed to talk to her, ever."

"I need you to be properly dressed for your housework." Sarah pulls one of the many boxes in the room toward her and pulls out all sorts of paraphernalia. First she wraps a light piece of white cloth around his mid-section covering his exposed privates. The wrap looks sort of like a skirt / toga combination. Next she gives Tommy a pair of white gloves and tells him to put them on. She attaches a short leash to his collar. Tommy is surprised that she is not covering his upper body, but that does not seem to be a priority for her. Finally, she attaches cuffs to his wrists and ankles, pulling an intricate pattern of thin rope through the cuff loops that force Tommy into a stooped position when he stands and walks.

Having properly prepared him, she grabs his leash and guides him up the stair into the main house. Tommy feels ridiculous. He looks like some sort of freak. He forces himself to not think about his appearance.

Rachel pulls Tommy into the kitchen and points to the sink. It's filled with dirty dishes and the rest of the kitchen is in similar disarray.

"I want you to clean this place spotlessly," she orders. "If I am not happy with it, you get demerits. You have 30 minutes to finish, then I will need to start dinner and you can clean up again afterwards. Here is how I want you to clean. You are to scrape all of the leftover food into this bowl. Nothing gets thrown away. You will use running water and soap to clean the dishes and pans, but you must leave the strainer in the drain so that no food gets washed away. When you're done washing put the food collected in the strainer into the bowl, too. After you finish, go set two places at the table and put out the TV tray for your self – set it next to my chair. You won't be needing a chair."

"Now start." Rachel smiles as she leaves the room

Tommy begins by taking the largest and dirtiest of the pans and carefully scraping the remaining food particles into the bowl. Most of the leftovers are things like dried up vegetables, hardened rice and pasta, and the odd piece of dried-up meat. The bowl is starting to look real gross and Tommy fears that this might be his dinner shortly. He shudders at the thought.

Tommy continues to work as fast as he can to get the kitchen clean. His white gloves are not making things easier – and they certainly are no longer white after just a few minutes.

All of a sudden, the door to the kitchen opens and Laura, Rachel's daughter, walks in. She lets out a short screech and looks at Tommy in dismay and surprise. Tommy drops everything and runs from the room to avoid contact with Laura. Almost immediately he can hear Rachel enter the kitchen and ask what happened. He hears them talk about Laura's encounter. He waits until he hears Rachel order him back into the kitchen.

"You did the right thing, Little Boy, by leaving the room," she says as he enters. Laura is still standing next to her with a little grin on her face. She is clearly looking down at this cloth covering his privates. "I have told Laura about who you are and what you are. She understands your role and the rules I have given you. Now finish the clean-up so we can make dinner for yourselves."

Rachel and Laura leave the room and Tommy resumes his work. He finishes the clean-up of the kitchen within the allowed time. Rachel examines his work and is basically satisfied with what she finds. She gives him two demerits for a few minor details he overlooked, but overall he feels that he came out of this task rather unscathed.

Rachel orders Tommy to go into the dinning room and to kneel at attention in front of his TV dinner tray while she finishes preparing dinner for herself and Laura. Tommy stays kneeling as ordered for what seems like hours. Finally, Rachel and Laura enter the room carrying their dinner plates and a drink for themselves. Rachel sits down and asks Laura to please fetch Tommy's dinner from the kitchen.

To his horror, the bowl of food residue is exactly what Laura comes back with. She places the bowl on the tray in front of him and lets out a short giggle as she takes a seat at the table across from her mother.

"Little Boy, eat that food up and don't waste any. I want you to eat it like the animal you are – no hands or tools. Just suck it right into that useless hole in you head." Laura is grinning from ear to ear and watching Tommy intently as he kneels there staring at the bowl full of slop.

Rachel and Laura start to eat their dinner and to discuss the events Rachel has planned for afterwards. Tommy hears Rachel tell Laura that she will be given an opportunity to learn more about the male body and that she is to pay close attention to the lessons. They are talking as if Tommy were not even in the room.

Tommy is mortified and practically hypnotized to the point of total immobility. He has not touched his food. All of a sudden, Rachel sternly tells Tommy: "You better eat that food we are giving you and soon. You have five minutes to finish or god help you!"

Tommy is rudely awakened to his surroundings. Instinctively, he drops his head into the bowl and begins to suck down the concoction of rancid leftovers. It tastes horrible and smells even worse. It is almost like eating trash from a dumpster. He can hear Laura laughing as she is obviously watching him endure his plight.

Trying to not think too much about what he is doing, he scarfs down the contents of the bowl as fast as he can. It takes him about two minutes to finish.

Rachel says: "Now get back into the kitchen and clean up everything. We have lots of fun stuff planned for you shortly. Come down to the basement when you are done cleaning up."

Tommy is extremely nervous as he begins the clean-up in the kitchen. The dinner preparation did not make too much of a mess, but he certainly feels that he is better off doing the dishes then whatever is in store for him the basement. He can only guess at what Rachel has in store for him. Sex education – what does that mean? Will she have sex with him? He feels strangely turned on at this thought. Rachel is very attractive. She is tall, lean and has long black hair that she usually wears in a ponytail. Her breasts are not particularly large, but they fit her overall body shape. She has a very pretty face with eyes that exude power. Tommy has heard the term 'MILF' before, which stands for 'Mother I'd Like to Fuck' and Rachel definitely falls into the MILF category. Laura is also very attractive. She is still very young and not fully developed like her mother, but Tommy can tell that she will be a total knock-out when she becomes a woman. Her hair is blond and she often wears it in a pony-tail like her mother. She has already started to develop little breast and Tommy noticed in the past, that their size seems to indicate that she will be well shaped when she grows up.

After the kitchen is cleaned up and Tommy collects his thoughts, he heads down to the basement and arrives to a waiting Rachel and Laura. They are sitting next to a large wooden table that they have moved into the center of the room. There are several large industrial type shop lamps on tripods around the table. The scene almost appears like an operating table in some weird lab.

Rachel says: "It sure did take you long enough! Aren't you looking forward to playing with us?" Tommy is too nervous to respond and merely stands planted at the bottom of the stairs. "Get your ass over here little boy and get on this table – on your back – head in my direction." Rachel orders sternly.

Tommy shuffles over to the table and crawls into its surface. The rope-work Rachel applied earlier makes it impossible for him to stretch out completely at first, but Rachel undoes the ropes almost immediately and says: "Lay down spread eagle and be still." Next, Rachel removes the loincloth and roughly pulls off his modified underwear leaving Tommy completely naked in front of the two women. Tommy hears Laura gasp at the sight of him fully nude.

Both Rachel and Laura quickly start to tie his ankles and wrists to the four legs of the table, stretching him to his physical limits. Tommy winces in pain at the tightness of the ropes. Next, Rachel slides a wedge-cushion under his butt, lifting his mid-section up high off the table.

Rachel says: "Laura dear, please sit down and let me instruct the boy on what I expect of him. I will explain everything you're seeing to you in a few minutes."

Rachel continues: "Ok little boy, here is the deal. I am going to cover your head with a pillowcase because I don't want you to look at my daughter while she gets her lessons. Also, to prevent any commentary from the subject, you, I am going to gag you." She inserts what appears to be a soiled pair of panties into Tommy's mouth, puts a piece of duct-tape in place and proceeds to pull the pillow case over his head. At first, Tommy gets a little claustrophobic and worries that he can't breath. He realizes quickly though, that he can still take in air through his nose and that the pillow case is rather thin so that breathing is not a real problem.

As Tommy lies there, immobilized and basically blind, he wonders what is going to happen to him next. He can hear Rachel tell Laura to get ready and to pay attention. He notices that the shop lights are turned on and that the lights are pointed directly at his privates. He can tell because the light is so bright that it shines through the pillow case, and also because the heat of the lamps can be felt on his nether-regions.

"Ok, let me give you a quick overview of the male private parts." Rachel starts. Tommy can hear the familiar sound of a rubber glove being snapped on. "The first thing is obviously the penis." Tommy can feel his shaft being grabbed and roughly waved around as Rachel talks about this part. "The penis is, for a man, his pride and joy. Lord knows why. It is rather ugly if you ask me. This particular specimen is un-circumcised, which means that the foreskin has not been removed." Rachel grabs the tip of Tommy's dick and stretches the foreskin upward. "On many baby boys these days, the foreskin is cut off right at birth, mostly for hygienic reasons. When it is removed, the male does not have to make any special efforts to keep this nasty unit cleaned. In this boy's case, his parents must have thought he can do it himself – we'll see in a minute. The other important thing that changes when a foreskin in removed is the sensitivity that the male has in his penis head." At this point Rachel pulls down Tommy's foreskin roughly, causing him to jerk in his ropes.

"The penis head," she says poking at it with her finger, "is filled with nerve endings. This is the same as our clitoris – only in males, it becomes this large, vulgar, disgusting thing. When the foreskin is removed, over time, the penis head gets so much friction and rubbing that it becomes less sensitive then the head of an uncircumcised penis. This specimen, therefore, is likely very sensitive." Rachel uses her gloved fingernail to scratch Tommy's dick-head. Tommy tries to scream out in pain, but his voice is totally muffled by the gag and the tape.

"When a male masturbates, he uses his hand to rub up and down on an erect penis. The rubbing motion stimulates his nerve-ending in the tip and eventually leads to his having an orgasm."

Rachel simulates the jerk-off month on Tommy's dick. It only takes a few strokes for his dick to start getting hard. Upon noticing this, Rachel slaps his ball sack with her free hand and warns Tommy not to even think about getting a hard-on. "I warned you about this – you better get control over yourself, real fast." That's five demerits.

The pain of the slap causes Tommy's dick to retreat back to a limp state. "Males are extremely weak individuals," continues Rachel, "they have no control over themselves. Even under threat of severe punishment, boys like this will get a hard on at the slightest stimulation. This is just one of the many reasons why males are far inferior to women."

Rachel continues her lecture: "When a male with a foreskin masturbates, his foreskin acts as a natural simulated vagina and helps in the process of achieving an orgasm. Boys that don't have a foreskin often use lotion or other lubricants to masturbate."

"Of course, the ultimate goal for any male is to not masturbate at all, but to be able to put this nasty thing into one of our vaginas. They aren't picky, as long as we will spread our legs for them. They also like us to put this nasty piece of meat into our mouths and suck on it – they call it a blow-job. I for one, do not give blow-jobs. You need to decide if you will ever lower yourself to that extent." Tommy can hear Laura whisper, "No way!"

Tommy feels like he must be in a dream. He is tied to a table, spread-eagle with his privates propped-up and exposed fully to two women – one of them a girl his own age. He is hooded and gagged and his privates are being poked and prodded like he is some laboratory specimen. Normally, Tommy is very shy and the extent to which his humiliation is currently being pushed is incomprehensible to him.

Rachel continues: "The shaft of the penis is basically just a muscle that engorges when the male is aroused. There are thousands of blood vessels that supply the penis with the blood to blow it up to almost three times it's relaxed state. This boy has been told to not get an erection so his dick is basically in its flaccid state right now. I will show you an erect penis later."

"Next we have the testicles or also called 'balls'." Rachel grabs one of Tommy's balls with her hand and pulls it forward which talking. Tommy tries his best to ignore the pain of her rough handling. "Each male has two of these and they are responsible for making the sperm that are useful to us mainly for baby making. They are also useful to us, because they are the most sensitive spot on a male's body and no matter how tough a guy is, he will drop to the ground like a rock if he is hit in this area. You can't even imagine how much pain a male feels when his balls are abused." At this point, Rachel starts to squeeze Tommy's ball between her fingers. At first she squeezes lightly but gradually increases the pressure. Tommy starts to jerk and scream in pain – it reaches a point where he can't stand it anymore – he is about to throw up and is having a hard time breathing with his mouth covered. He starts to cry and as soon as he does, Rachel lets off.

"See what I mean?" she says. "All it took was the pressure of my two fingers and his boys started crying in seconds. That is how much power we have over men."

Continuing her lecture, "Right down here, is where we women have our vagina." She points toward the space between Tommy's balls and his ass. "Men have nothing useful here, but this area is good for punishment and torture. If this boy misbehaves, I will probably make good use out of this space. The male ass, is pretty much the same as ours – only hairier." She pokes her finger into his butt-crack. "We can examine this part of his body later, I will need to tie his legs up over his head to get better access."

Tommy can't even comprehend what is happening to him anymore. The humiliation is too much to grasp. He has never felt so used before. Like a piece of meat.

"Ok Laura, now you can touch and examine the subject if you'd like." He hears Laura giggle with joy and next hears the sound of more rubber gloves being put on. Soon after, he feels a hand reach for his penis. This time it is much gentler and almost timid – obviously Laura's hand, not Rachel's. She gently squeezes his shaft and pulls on his foreskin, examining how it pulls forward and back.

Tommy's dick starts to get hard almost instantly at the thought of sweet little Laura touching him and no sooner does he feel the erection coming on, he hears a loud admonishment from Rachel: "What the hell is wrong with you???!!!" WHACK. He feels his entire insides convulse as something smashes into his crotch. Rachel obviously had some implement at the ready to strike Tommy at the moment she saw an erection.

The pain is so great, he gasps for air and almost passes out. Laura's hand jerks away from his penis and Tommy is left to try and catch his breath. WHACK – Another smack in the balls. "If you get a hard-on one more time, I will castrate you, do you understand?" screams Rachel. "That's another ten demerits!"

Tommy cannot answer. He is seeing stars behind his hood. He can't breath. He is terrified.

A few moments later, Laura resumes her examination. She plays with his balls, but Tommy is still in so much agony that he barely feels her touch. Her poking around his ball-sack is merely a continuation of the pain he already feels. He is quietly crying behind his hood and he hears Laura ask with some concern in her voice: "Is he alright? I have never heard a boy whimper like that."

"He'll be fine," says Rachel, "as long as he doesn't try to get any more erections 3;" she finishes with a rather threatening tone in her voice.

Laura takes a little more time to examine his privates and then says to her mom: "Can I see his thing when it is large?"

Rachel replies: "Are you sure you're ready for that? It can be rather disturbing, not to mention nasty. We can take it slow and you can see it tomorrow if you like."

Tommy is totally freaked out. TOMORROW? When did this become a multi-day event? When was he going to be let go?

"No, I can handle it now," says Laura. "I've seen it in pictures, but never in real life."

"Ok, then I will show you how to make it happen," says Rachel. "Here is what you need to do. Just take his shaft into your hands and rub his foreskin up and down around his penis head. At the same time, very gently caress his balls with your other hand. You will see the results almost instantly. – Boy, you are allowed to have an erection this time," finishes Rachel before allowing Laura to begin.

Laura does as instructed. She starts to jerk off his penis and gently rub his balls. Tommy instantly feels his member swell from the wonderful sensation. Within ten seconds, despite the lingering pain in his groin, his dick is almost completely erect.

"WOW" exclaims Laura, "that is unbelievable. I would never have thought it would happen this quick. And they expect us to put one of these things inside us?" Laura laughs as she says this.

"Well, males are weak creatures and they have no control – as you can see. I beat the ever-living heck out of him and he still gets an erection within seconds. Isn't that pathetic? And, yes, they do expect us to put this thing inside us – but if you learn how to dominate men like I have, you can do it on your terms and only in a way that gives you pleasure."

Tommy is ready to cum at this point and knows that if he does, he is a dead man. Laura won't stop jerking him off while she is talking to her mom and if she continues much longer, he will lose it. Thankfully, in the last second, Laura gets tired of moving her hands and lets go of his pecker. Tommy let's out a sigh that can be heard even with his gag still in place.

Rachel laughs and says: "He must have been real close to cumming. Lucky for him, you stopped. I would have killed him if he had."

Tommy is still hyperventilating behind his gag. Sweat is dripping into his eyes from his forehead. His dick is throbbing, both from excitement and pain. He is scared and at the same time he is resigned to his fate.

"I want to see what is looks like when a boy cums," says Laura to Tommy's horror.

"Well, let me think about that," replies Rachel thoughtfully. "We can finish him off ourselves or we can make him do it for us. I personally think we should let him do it since that is what males typically do to themselves when they need to relieve some pressure. Plus, this boy is being trained right now and he is never to have an orgasm that is enjoyable to him. We want to train his mind to associate orgasms as something bad and painful."

Laura agrees to let Tommy masturbate himself to an orgasm. Tommy lies motionless in anticipation of what they will make him do. Suddenly he can feel his ties being loosened and his arms and legs regain mobility.

"Get up!" orders Rachel. Tommy slowly raises himself on the tabletop and tries to get his bearings. Rachel roughly pulls off the hood from Tommy's head and pull off the tape on his mouth. The tape almost takes his lips off and he screams out loud at the pain. Trickles of blood come from his lips and they feel as if he has been on an Antarctic expedition without Chapstick. The panties are taken from his mouth and tossed on the floor next to the ropes that bound him.

"Get on your knees over there in the corner and face us," orders Rachel. Tommy scurries over to the corner and gets on his knees. Rachel and Laura adjust their seats to face him and both have an evil grin on their face as they look down at him. Laura's grin is a combination of evil and anticipation. She is obviously very excited at what is about to happen.

"Boy, I want you to jerk off and cum for us. At the same time, you will suck your thumb and cry like a little child. Just like you did for the ladies, you better be convincing. Laura will grade you – if she doesn't buy the crying, you will be punished severely."

Laura giggles as Rachel gives Tommy this order. Tommy is mortified. The humiliations just seem to get worse and worse. He will never be able to show his face in public again.

"Start!" yells Rachel and Tommy instinctively grabs his dick and starts to jerk off. He also places his thumb into his mouth and tires his best to start crying. He congers up all of the feelings he has gone through over the past several hours along with the still lingering pain in his privates and lips. Very soon, he is able to cry actual tears. He continues to think of the humiliation being inflicted on him, which helps keep his tears going.

He can hear Laura say: "Cool! Is that what they do to themselves all the time?"

"Yes," responds Rachel. "Isn't it pathetic?

After about a minute, Tommy can feel the orgasm coming on. He starts to rock forward as he continues to jerk off, suck and cry. Then, he exhales loudly and shoots a stream of cum in the direction of the ladies. His body becomes limp and he almost drops to his side from exhaustion. Cum is dripping off his penis tip and through the fingers of his hand.

"WOW!" exclaims Laura. "Is that what it looks like? Totally cool. I don't think I would want that stuff in my mouth though!"

"Well, I wouldn't either. Sadly, we need that nasty stuff to get pregnant. Otherwise there would be no use for it at all."

"Boy, I never gave you permission to cum. That is five more demerits. "Laura, what score do you give him for his crying? Were you satisfied with his acting?"

Laura giggles and says: "Well, I guess he did an ok job. He doesn't need to be punished if you ask me." The authority in her voice is remarkable. She really seems to relish her new found power over him.

Rachel turns to Tommy and says: "You're lucky I wasn't grading you. I would have given you more demerits. My daughter must like you – that is NOT a good thing. Now clean-up your mess on the floor and on your hand."

Tommy starts to wipe his hand on his skin to get rid of the cum but is immediately stopped my Rachel. "With your nasty mouth, boy. I want you to lick up the cum and clean everything with your tongue."

"Gross," exclaims Laura with a giggle, "but I guess if they think it's good enough for us, it should be good enough for them, right?"

Tommy does as he his told. This newest humiliation barely registers with him anymore after all that has transpired. He licks the floor, which is covered in dust and dirt to get all of his cum residue off the ground. After that, he licks his hands clean. All the while, Laura and Rachel are watching him laughing quietly to themselves.

"So that is what a male orgasm looks like," says Rachel. It's isn't pretty but it is what it is. If you get to the point in a relationship where you allow a man to get intimate with you, you will be ready for what awaits you. But, you are still very young and have lots of time to learn more. Plus, little Tommy here will gladly let you experiment on his body until all of your questions are answered, won't you little boy?"

"Yes, ma'am," says Tommy weakly. He is already checked out from the scene. His mind is numb and he no longer feels pain or humiliation. His limits have been reached.

"Ok, Laura, it's time for you to get upstairs and do your homework and go to bed. The little boy and I have some business to finish and then he will be off, too 3; that is if he is able to do what is expected of him."

Laura makes a few objections about wanting to stay and watch, but Rachel firmly sticks to her decision to make her leave. Tommy is only slightly worried about what is to come next since he is still in the trance like state that his pervious torments have caused.

When Laura is gone, Rachel turns to Tommy and says: "You have some demerits to work off before you can leave. Do you know how many you have?"

Tommy thinks hard, but is pretty sure he lost track somewhere at 20. He guesses: "25?"

Rachel smiles and says "No, but now you have 40. 32 was the count, but since you couldn't remember, I will round it off for you."

"Here is my punishment routine. I will sometimes use to cane to beat you senseless if I am so inspired, but most of the time I will use what I like to call my Milking Box'. The milking box is an old cardboard box that I saved from when I bought our big-screen TV. It is just big enough for a little boy to fit in to. You won't fit comfortably, but that is not the point, is it?"

"The purpose of the Milking Box is to teach little nasty boys that masturbating is bad and that orgasms are not for fun. If you demonstrate to me that you can't control yourself, the Milking Box will be used to teach you the downside of your pathetic urges."

"Based on your overall demerits, I will apply a simple formula to see how many times you will need to orgasm while in the box. To prove that you really had an orgasm, you will have to ring a bell inside the box each time you cum and I will hand you a tissue through a small opening in the side. You will wipe your cum onto the tissue and hand it back to me. I will be the judge of whether there is enough 'milk' on the tissue to qualify as a legitimate orgasm. Obviously, with each increasing orgasm it will be harder and harder for you to cum. Also, the amount of milk will decrease each time, but I know what I am expecting and what you need to deliver. You will be tied up inside the box to make the experience as uncomfortable as possible. Your hands will be connected to your tongue using a string and a clamp so that you have to pull on your tongue in order to reach your dick. You will not like the Milking Box and that is the whole point."

"So here is the simple formula: I take the total number of demerits and divide by five. That means today, you have 40 demerits, which equals eight orgasms. Now, since it's your first time and since I don't want to wait forever, I will graciously reduce your punishment to five for today only. This means that you will have to orgasm five times before you can leave. If I don't accept a tissue after you cum because there is not enough residue on it, then you will have to do it again, so make sure you collect as much cum in your hand as possible and don't spill any."

"The main thing to remember is this. You will be VERY uncomfortable in that box. The quicker you get all five orgasms out of the way, the quicker you get out. It is 9:00 PM now and I go to bed at 11:00 PM sharp. If you are not done by 11:00 you will be staying the night in the box. I highly recommend against that."

She walks over to the other end of the basement and pulls a medium sized box into the center of the room. The box has a large Sony logo on the side and has obviously been modified for its intended purpose. There is a very small cut out on the side that will likely serve as the tissue dispenser. The top of the box has been covered with a lid that fits tightly over the top instead of the usual flaps that fold down.

Rachel lifts off the lid and orders Tommy to get inside the box. He is still wearing this wrist and ankle cuffs as well as his collar. Other then that, he is completely naked. He climbs into the box and sits down as instructed. When seated he finds he has no room on either side of him and that his knees are forced into his chest because he is too tall to stretch his legs out any further. By spreading his legs, he can barely get to his dick. He wonders how he is going to be able to jerk off from this position.

Just as he tries to figure out his predicament, Rachel leans over the edge of the box and says: "Open you mouth and stick out your tongue." Tommy does what he is told and Rachel attaches a clamp to his tongue. The clamp is made of plastic and has little rubber nubs on the tips that dig into his tongue and make it almost impossible to slip off. If push came to shove, the clamp would likely slip off but not before causing excruciating pain to his tongue. As it is now, the sensation of the clamp causes his tongue to tingle almost immediately and drool starts to pool in his mouth.

Rachel attaches a nylon string to end of the clip and ties the other end the wrist cuffs, tightening the string to the point where he can only reach his cock when bending as far as he can forward with his neck and upper body. Now all he can do to jerk off is use his two index fingers and try to masturbate while continuously to rocking back and forth. He can immediately see that this punishment is about as harsh as it gets. How is he going to get through five orgasms by 11:00 tonight? That is only two hours. And if he doesn't finish, he will be in this box all night. That might do permanent damage to his spine – not to mention his tongue.

Rachel orders him to 'test' his ability to reach his dick and also to reach the little window that she will use to hand him the tissues. He can barely reach both, but it is enough to satisfy Rachel. She places the cover back on the box, putting Tommy into the dark. He can hear a little tinkle from a bell that is obviously attached to the inside of the lid. Rachel tells him to ring the bell when he has completed his first orgasm.

Dirk immediately goes to work. He reaches down as far as possible and starts to rub on his limp penis. It starts to get hot in the box very quickly and a combination of drool and sweet start to drip down onto his lower regions.

The task is extremely painful and difficult. Each stroke requires him to tug on his tongue and to bend forward to his limit. Thankfully, his dick is hard after a few seconds and he can feel an orgasm coming on after about one or two minutes. Strangely, the predicament he finds himself in – as humiliating as it is – is also a turn-on for him. He can't understand why, but thinking of all that has happened to him today, and in the past encounters with the ladies, makes him come quickly.

After his first orgasm, he realizes to his great horror that much of his cum has splattered on to the wall of the box and then dripped onto his leg. He knows that he has to show enough milk to convince Rachel he had an actual orgasm if he wants it to count.

Quickly, he rings the bell above his head and soon after hears Rachel approach and slid a tissue through the small opening. He takes the tissues and tries to mop up as much of his cum as he can. Then he squeezes the soiled tissues back through the opening.

A few seconds later he hears Rachel say: "That is definitely not enough cum to convince me of anything. But, since I don't think you would be dumb enough to cheat on the first orgasm, I believe you this time. You better do a better job of catching your milk going forward though. You have four more orgasms to go."

After a few minutes to recover, Tommy again starts to stroke his penis. This time, the hardening takes much longer and he can already tell that he will need a lot longer then he did before. It takes him about 15 minutes to reach the second orgasm. This time, he cups one of his palms over his dick right as he cums in order to catch as much of the milk as he can. The result is that much of the substance drips back down onto his groin and starts to ooze between his legs.

He quickly rings the bell and gets another tissue handed to him. He mops up the mess and again pushes the tissue back for inspection.

"Better," says Rachel, "but remember, you will have to be even more careful going forward since there will be less and less each time."

The next time it takes Tommy almost 30 minutes to reach orgasm. By now, the pain is so severe in his back and neck that he can only feel tingling in his legs. His tongue is numb and his mouth dry, having lost all it's moisture to drool. He catches his cum in his hand and tries to keep it there by closing his fist around the substance.

Thankfully Rachel accepts the sample he gives her. He is now two orgasms away from freedom, but he is also running out of time. Rachel tells him that it is 10:15 and at the rate he is going, he will be hard pressed to make it in time.

His privates are completely spent. There is nothing left. He tries his best to get another erection so that he can work on the fourth orgasm and finally, after about twenty minutes, he gets one off. Again, Rachel accepts his sample and Tommy is happy that at least he has found a method to successfully collect the samples.

His biggest problem now is time. Rachel tells him he has 25 minutes left and he frantically starts to rub again. The pain has reached a point where he no longer really feels anything. He is so exhausted that he starts to cry. Nothing is happening anymore between his legs and he is starting to realize that he might actually have to spend the night in this hell-hole of a box. He sobs out loud at the thought. Still, he continues to rub.

At some point shortly thereafter – it only seems like seconds – Rachel announces that she needs to go to bed and that he better finish immediately unless he wants to spend the night. Hearing this, Tommy has such a deep feeling despair and helplessness that he almost passes out, but at the same time it triggers something in his privates that allows him to squeeze out a final orgasm just in the nick of time.

He uses his last remaining energy to ring the bell. Rachel sounds surprised as she approaches lifts the lid off the box, letting in the bright light of the basement.

She looks down on him and almost feels sorry for him at the sight. He is crumpled over and totally covered in sweet. He is shivering from cold and exhaustion and his eyes are red from crying. His tongue is swollen and dry and his penis is limp, raw and sticky.

Rachel unties his hands and removes the clamp from his tongue. The blood rushes back into his tongue causing the pain to shoot instantly back to full force.

She helps him out of the box and lets him sit on the cellar floor for a few seconds to recover.

Finally she says: "You only need to do one more thing before I let you go. You need to put the box away for me and them get rid of the tissues that you soiled in the punishment process. I don't care how you get rid of them, but they have to be gone from here and you can't carry them out in your hands. That basically means you have to either ingest them or else shove them into one of your body cavities. (Nose, ears, ass 3;.) They have to be completely out of sight so if you choose the ass option, you have to force them all the way up there.

Tommy just wants to go. He numbly takes the tissues and begins to eat them. He chews as much as he can and them tries to swallow. The first tissue gets stuck in this throat and Rachel laughs as she hands him a glass of what looks like water. He quickly drinks from the glass and wonders what the strange taste is. Rachel informs him that he just drank a combination of her and Laura's piss water taken from the toilet. He doesn't care, and just continues to eat his cum covered tissues. It takes him five minutes and he is all done.

"Now we just need to record the days events in your log. Come upstairs with me and you will write down today's events for the other Ladies to read."

She hands Tommy's clothes to him and takes off his collar. Tommy is both relieved and apprehensive. He does not trust the apparent end to this crazy ordeal. Nevertheless, he follows Rachel upstairs after putting on his street clothes and takes a seat at the kitchen table per instruction from his Mistress.

"You will recount the major events of this evening and I will check it for completeness. If you don't do a good job, I will enter demerits into the log to be applied by the next lady you visit, so do a good job."

Tommy takes about 45 minutes to accurately recount his visit with Rachel and Laura. As he documents the events, he is struck by the incredible level of humiliation he just endured. He ate trash; was examined in the most intimate ways by two women; forced to masturbate and eat his own cum off the floor; punished by being forced to orgasm five times within two hours and then forced to eat the tissues that were used to mop up his cum. Not to mention the pain and humiliation he was made to endure.

Once finished, Rachel reviews his writing and adds her own commentary, which Tommy is not allowed to see. She seals the log-book and gives Tommy permission to leave her house. She gives him an envelope that contains the next assignment he will be required to attend.

Tommy practically runs to his bicycle and races home as quickly as he can. Once home, he showers and washes every part of his body as though he had just been exposed to some deadly disease. Afterwards he crawls into bed and curls up into the fetal position hoping that he can just go to sleep and forget what has happened 3;.and what is likely to happen next.

Chapter 4

Tommy goes to school and suffers through a day of sitting on his raw ass on the hard school seats. Even though Rachel did not beat him, the box basically did the trick for her. Plus, his tongue is still swollen and he sounds like he has been to the dentist when he talks.

Before leaving for school, Tommy checked the envelope that Rachel gave him. To his horror, the next Lady to summons him is Deb. He is truly afraid of Deb. She seems like the cruelest of all the ladies – not to mention the fact that the entire club was her idea in the first place.

Deb wants to see him on Friday after school. The timing worries him. Since the next day is not a school day, Deb can easily keep him for the entire weekend. He was instructed by Deb originally, to always tell his parents that he was going to a friend's house and might be spending the night, whenever he was summoned. His parents were very easy going and trusted Tommy, so they don't ask too many questions.

As Friday rolls nearer, Tommy becomes increasingly nervous about his upcoming ordeal. What would Deb do to him? What punishment could he recommend to her that won't earn him ten demerits? Would she go easier on him now that he has already learned so much? Would he be allowed to go home the same day?

Serving Deb

"Oh boy, this is starting out great," thinks Tommy. He tentatively walks around the house and finds the lower patio that Deb referred to. It is rather hidden from public view due to several tall bushes that line it parameter. Adjoining the patio, there is a door to what appears to be the basement of the house.

Tommy takes off his clothes and folds them neatly. He expects the process to be the same as he has been taught, and puts on his collar together with the attached logbook. Finally, just in case, he gets on his knees into the neutral position and waits for Deb.

Several minutes later, the basement door opens and Deb emerges with a smile on her face. She looks great! She is a very petite woman, in her 30's with long curly red hair. She wears her hair open most of the time, but today, it is pulled back into a ponytail making her look much younger then she is. She is wearing a simple white dress that might be a morning gown and he thinks he can see her naked skin shimmer through the fabric as the light hits her body.

Deb looks down at Tommy and coolly says: "Get inside. Kneel in the center of the room."

Tommy scurries to get into the house and get into position. Deb follows and closes the door behind her. She pulls up a stool and sits down directly in front of him. She detaches the logbook from Tommy's collar and begins to skim the entries.

While reading she crosses her legs and uses her free foot to gently nudge Tommy's penis and balls as her leg bounces up and down. Her touch, along with the incredible way she looks, gives Tommy an instant jolt of excitement and he has to use all his willpower to avoid getting an erection.

After reading for a few minutes, Deb sets down the book and looks at Tommy. "I really don't have to read too much of this – I have been getting updates for the other Ladies after each of your visits. Also, I am not even going to ask you if you jerked off since visiting Lady Rachel, since I know she milked you to the point where you couldn't possibly have jerked off since then. Finally, I am not going to ask you for your punishment idea, since I have some really good ones already thought up and you can save whatever pathetic idea you had for your next assignment."

Tommy is sort of relieved about the punishment pass. He was sure he would have earned ten demerits right off the bat and now he was still 'clean'.

"Little boy, let me explain something to you," Deb starts. "Each Lady in the club has different desires and expectations from their interaction with you. We all have our turn-ons and we all play a role in the 'grand design' of what the club aims to accomplish. The overall goal is to create a perfect little male creature that will do exactly what we want and will not be burdened with the usual male urges that get in the way of our joy and pleasure."

"To that end, we have all agreed to focus on a particular area as we use and train you. Rachel focused on orgasm control and humility. Sarah focused on following orders and attention to detail. Becky will focus on manners and proper male education. Taylor will focus on sex education, so that you can properly serve a lady. Finally, Lisa will pay close attention to your personal fitness and appearance."

"That leaves me, doesn't it? You are surely wondering what my role is? Well, mainly, I am going to use you for my pleasure since I am the overall coordinator of your training. However, I will focus on your ability to handle pain. That means, I will be looking for and pushing your limits. Primarily your limits in pain but also your limits in other things. I will report back to the ladies and let them know what these limits are."

Upon hearing his, Tommy involuntarily starts to cry. Actually, it's more of a whimper, but the fear of what Deb just said confirms his worst nightmares about her. She is indeed the most cruel and sadistic of them all and now he was going to feel the full impact of her cruelty.

Deb smiles at Tommy and stokes his head gently at seeing the tears well up in his eyes. "Little Boy, I am not going to kid you, you are going to suffer greatly while you are with me, but you will survive and you will be a better boy afterwards. Now suck it up and try your best to learn what I am about to teach you."

Deb attaches a leach to Tommy's collar and leads him to a side room within the finished area of the basement. The room appears to be a simple guest room. It contains a small bed and a nightstand. The bed is stripped of all its sheets and only the bare mattress is visible.

"Get on the bed, on your back, and spread your arms and legs out toward the four corners," orders Deb. Tommy does what he is told. Deb quickly and efficiently ties his arms and legs to the corner of the bed using leather straps. While she is finishing up, she tells him what she plans to do.

"Little boy, I am a single mother with two small children. My ex-husband was a bastard – like most men are. He left me after I had the kids because he wanted 'his bachelor life back'. Well fuck me! Now I am saddled with two kids and no guy wants to have a relationship with a women already tied down. That leaves me alone, bitter and horny as hell."

"So to start the day, I am going to get my rocks off and you are going to help. I am going to masturbate myself to multiple orgasms and I am going to use your face as my dildo. All you have to do is keep your tongue out nice and long and follow my orders. You are not allowed to have an erection and I will punish you severely if you do. Also, I will be grading your performance while I am getting off. After I am done, I will punish you as I see fit based on how well you did. Do you understand?"

"Yes," squeaks Tommy weakly. He is tied to the bed and completely helpless. He does not know what to expect but he can't imagine it will be pleasant.

"Good," says Deb and straddles Tommy on the bed while slightly raising up her gown. Tommy can feel Deb's naked legs touch his sides. She is obviously nude underneath the gown. As she sits on his stomach, looking down on him, he can feel her wet pussy touching his skin. He is instantly turned on but thinks of the most non-sexy things he can to control his impending erection.

Deb slowly pulls off her white gown. It slips easily over her head and exposes her full naked body. She is obviously teasing him. He can no longer control his penis and realizes that he has pitched a tent. Deb looks back over her shoulder and sees his erection. She chuckles and says: "God you men are weak. That's all it takes? Good lord!".

She reaches back, grabs his balls and squeezes with incredible force causing Tommy to almost jump under the ceiling with pain. He gasps and screams but she won't let go for about 15 seconds.

Once she releases his balls and Tommy is able to breath freely again, he notices that his erection is gone. "Good," says Deb and smiles at him.

Next she leans over Tommy's face and spits a big gob of spit right on the center of his face. "That's to help with the lubrication," she says happily. She pulls herself up and positions her pussy directly over Tommy's face. Then she says: "Take a deep breath," and lowers herself onto his face.

Tommy feels the wetness of her pussy envelop his face. Her cunt is directly on top of his nose and his chin is buried in her ass. He can see a little light but the only thing he can make out is pubic-hair.

Deb starts to ride his face with great intensity. She grabs hold of his hair and pulls him tightly into her pussy while rocking back and forth on his face. She is basically rubbing her clit over his nose, using it as stimulation for her pussy. The friction with her public hair causes burning on his skin almost immediately and he realizes that he will likely have a 'rug-burn' on his face for days to come.

"Tongue out," she screams in the heat of the moment and Tommy remembers what she had instructed earlier. He extends his tongue and Deb begins to rub her pussy up and down his face, alternatively using his nose and then his tongue for stimulus. His face is completely drenched with her juices. His face is on fire and he can smell only the strong scent of womanhood.

With each passing minute, Deb gets more and more into her sex frenzy. She begins to moan loudly and increasingly intensifies her rubbing of Tommy's face. He has a hard time breathing and tries to take a breath each time she is at the bottom of her rub-cycle.

Finally, Deb screams out loud and has a massive orgasm, that covers Tommy's face and hair with warm, sticky pussy juice. She slows down the rhythm of her rubbing and begins to relax a little. Then she grabs Tommy's head and uses his hair to clean herself off. She gets off the bed and puts her gown back on.

Tommy is transfixed. He just lays there and does not move. He finally can breath again and his face is completely wet and raw from the chafing. Deb looks down at him with amusement. She is clearly glad to have gotten off, and seems a little more relaxed.

"I am going to leave you here for a few minutes, while I go get a drink. When I come back, I will grade you."

Tommy lays there on the bed, helpless and exhausted. His nose and mouth are filled with pussy juice. His face is starting to dry and develop a thin crust of female secretion in the places that are dry. He can tell that his hair is completely matted and probably sticking-up in all directs like Camran Diaz's hair in the movie Something About Mary. All he can smell and taste is womanhood. He is strangely turned on, but thankfully, his penis does not betray him – he is too exhausted to get an erection at this point.

Deb returns after a few minutes carrying a large bottle of water. She has finished off about a third of the bottle and is obviously trying to regain her composure as well.

"Are you thirsty little boy?" she asks.

"Yes Ma'am" says Tommy meekly.

"Ok, open up," says Deb and takes a large gulp of water from the bottle. She swishes the water around in her mouth and then leans over and lets it run into Tommy's open mouth.

The water feels and tastes good. He is very turned on by the idea of taking it from Debs mouth. She repeats the feeding process several more times and then sets the bottle next to the bed.

She walks over to a closet in the corner of the room and opens the door. Inside, Tommy can see tons of BDSM equipment, tools and toys. His heart sinks. She grabs one of the canes that are neatly hanging on hooks from the closet wall.

Quickly, she turns back toward him and shows him the cane she has selected. It is a thin, long bamboo cane with a leather loop at the end Deb is holding. She waves the cane through the air a few times and it makes a distinct swishing sound that Tommy has come to know and fear.

"I am debating if I should gag you," says Deb. "But, no, I think I want to hear you scream."

Tommy is terrified. His eyes start to fill with tears immediately and he instinctively begins to beg Deb to not hurt him. "PLEASE Ma'am, please don't hurt me. I will do whatever you want. Please just don't hurt me!!!"

Deb laughs. "You will do whatever I want you to anyway! It makes no difference if I hurt you. And I certainly plan on hurting you. So save it!"

"Now, let's see. You got an erection earlier – that's not good; and you forgot to use your tongue until I reminded you – that's not good; and then I would say your overall performance was mediocre at best – that's not good either. All in all, I think you deserve 50 lashes.

"NOOOOOO!" Tommy cries! "I can't take 50 lashes with that thing. It will kill me." He is sobbing uncontrollably and straining at his cuffs that are still tied to the bed.

"Well, that is exactly what I am going to find out. I will stop right before you die," she says with a laugh in her voice. "Besides, I have never heard of anyone dying from a good caning 3;"

Before Tommy can protest any further, Deb raises the cane and unleashes the first swat right on top of his upper thighs. The pain is indescribable. Tommy screams and starts to pled again, but before he can get a word out, the second stroke hits him on the stomach, silencing him temporarily as it knocks the wind out of him. She continues on without pause. She strikes all over his chest and stomach, all the way up and down his legs, under his feet and even on his arms and hands.

When she reaches 40 strokes, she briefly stops. She is sweating at this point from the effort and looks at Tommy who is writhing in pain and squealing at a pitch that she has never heard before from a male creature. His pleas are no longer audible. They are more like the faint screams of a dying victim of a violent crime combined with the occasional sobs and gasps for air that are chocked off by more screams.

She looks down at his marked body and smiles. "You are gonna feel and see this for a long time." "Now for the grand finale," she says and again raises the cane.

This time, the blow lands on his dick and balls. After the fourth stroke, Tommy passes out and is awoken a few seconds later by Deb as she pours water on his face from her mouth.

"You have six more strokes to go," she says in a fake gentle tone. "You can't be asleep for that, now can you?"

Tommy is delirious. Of all the pain and humiliation he has endured over the past few weeks, this is by far the most extreme and the worst he could have ever imagined. He braces himself and Deb continues on, just as if nothing has happened. At the ninth stroke, he again looses consciousness for a few seconds, just to be re-awakened by Deb as before. Finally, the 50th stroke is administered and Tommy is left to recover – albeit still tied to the bed.

About 20 minutes later, Deb returns to the room to find Tommy asleep. He is so exhausted that he half passed out, half fell asleep. She rudely wakes him by slapping his balls and sternly saying: "Wake up you lazy boy. Time to work!"

She unties him from the bed and makes him stand. His knees are very weak and the pain all over his body makes it hard for him to stay standing still. Deb leans down and attaches a male chastity devise to his balls and penis. His dick is still raw from the caning and the devise seems to dig into his throbbing flesh.

Next she attaches a chain to his collar and the other end to the chastity devise. She clips a leash to the middle of the chain thereby creating a double attachment for the leash. Now when she pulls on the leash, his neck is pulled along with his cock. In this manner, she leads him back outside to her backyard.

"Boy, it is time to exercise," she says. "I have a few drills that I have designed for you that you will perform. First I want you to do some relay sprints. You will run, as fast as you can, to the other end of the lawn, drop to your knees (about 40 yards) and ring the little bell on the tree at the end." The bell was attached at the lower part of the tree and Tommy wondered why it was placed in the strange location.

"Then you will sprint back here as fast as you can and again fall your knees in front of me. You will repeat this until I tell you you can stop. And again, remember that I will be grading you. If you don't run as fast as you can, I will punish you. Oh, there is one complication that I should make you aware of 3; your hands are going to be tied between your legs while you do this."

Tommy was totally confused. Tied between his legs? Deb grabs a pair of modified handcuffs from a box she has placed on the patio and orders Tommy to lift his leg. She forces one arm behind and the other in front of him and attaches the cuffs so that the hands met right between his legs. It is as if he is sitting on a saddle made up of his hands and the cuffs. The length of the chain between the two cuffs is just long enough to allow him to get both feet on the ground, although he is sort of stooped over to one side slightly because of the awkward angle his shoulders are bent from the restraints. The metal cuffs start digging into his wrists immediately and he can tell that his exercise is going to be painful and tough.

"Now I am going to count to three and you will get going. And keep in mind, you better run as fast as you can – dig those little toes into the grass and sprint at top speed. Your future pain is going to be directly related to how well you do this."

Tommy is mortified. How is he supposed to run in this state? He hears Deb count to three and starts off as fast as his awkward position will take him. As he starts to run, he can hear Deb laugh and yell, "faster you little twit." Tommy is doing his best to run fast, but without the use of his arms and with his wrists tied together between his legs, there is only so much traction he can get.

He reaches the tree with the bell in about 15 seconds. He drops to his knees and rings the bell by raising one knee off the ground and hitting the bell. He tries to get back up, but it is tougher then he thought. Not having his arms free makes the stability of standing up from the ground so much harder.

Once up, he sprints back toward Deb. It must be a funny sight seeing him waddle toward her in this bound state, because he can see her laughing hysterically the whole time he is approaching. He arrives next to her and drops to his knees again, trying to catch his breath. Deb stops laughing just long enough to yell: "Again, come on, put a move on! At this rate, you might actually die during your next caning!"

Tommy again stubbles to his feet and starts to run. He is running for his life. He is crying, too. He feels so helpless and afraid. He can't go any faster and yet he is obviously not going fast enough. All he can hear is his quickening breath and Deb laughter.

He repeats the course several times more and after, what seems like the tenth time, is so out of breath he can barely move anymore. Deb has stopped laughing and is now merely yelling at him to move it. She has a cane in her hand and each time he gets back to her side, she swats him hard wherever she can find and opening. Tommy's mouth is dry and he cannot catch his breath. He fears he will pass out or vomit. Nevertheless, he keeps going, although at this point he is almost walking rather then running. Soon, he realizes that Deb is rubbing herself under her dress as she watches him struggle to continue on. She is taking great pleasure in seeing him suffer. The more exhausted he gets, the more excited she becomes. Finally, Deb leans back in her chair and obviously has a massive orgasm. At that moment, Tommy is just returning from the tree side of the lawn heading her way. The strain and pain on his face must have pushed her over the edge. When he reaches her and falls to his knees she whispers "Ok, stop."

Tommy collapses next to Deb's chair gasping for air. She grabs his hair and forces his face into her crotch. She smells strongly of sex. Since he hasn't even gotten close to catching his breath, he is forced to suck breath from between her legs and then exhale forcefully through any opening he can find. The sensation of Tommy's desperate efforts to breath causes another orgasm for Deb after a few moments.

She lets go of his head and he drops to the ground like a rock. Deb stands up and walks back toward the basement. "I want you inside in two minutes," she orders as she walks away.

Tommy is left lying on the ground to catch his breath and to regain his composure. After what seems like only a few seconds, Deb returns and unlocks the handcuffs that are still holding Tommy's wrists tightly in place. She picks up her leash and clips it to Tommy's two-point chain. Without saying a word, she drags him back into the basement.

She leads him to a small bathroom next to the guest bedroom where he had been raped earlier. She points to the shower and orders him in. "Get on your knees in the shower," she says as she turns on the water. She only turns on the cold faucet and Tommy is struck by a stream of ice-cold water that takes the remaining breath he has left right out of him.

Deb uses a dirty old rag to scrub Tommy's face and upper body. She orders him to open his mouth and roughly scrapes a bar of soap in and out. Tommy is sickened by the taste of the soap and tries his best not to gag. Finally, Deb turns off the water and proceeds to straddle the sides of the shower-tub, standing directly over Tommy.

"Open up your mouth and let me rinse down some of those soapsuds," she says. "I am going to pee into your mouth, and I don't want you to waist a drop. If you do, you will be severely punished."

Tommy opens his mouth and puts it as close to Debs slit as he can. She starts to pee and Tommy puts all his efforts into drinking a swallowing so that nothing runs out of his mouth. Her stream seems to be never-ending. She just keeps on peeing and peeing. The taste is not nearly as bad as the smell. He feels so degraded. He is usually even grossed out by his own pee and now he is drinking the piss of another woman.

When she is finally done urinating into Tommy, Deb gets off the tub edges and pulls the still wet and shaking Tommy out of the bathroom by his leach. He can still taste the soap in his mouth with thankfully overshadows the taste of pee. He is frightened and tired. What will happen next?

Deb leads him back into the bedroom and orders him to lie back down on the bed as before. She again attaches his arms and legs to the bed as before. Once he is secured, she leaves the room. Tommy is left to think of his situation and uncertain of what is to come next. He thinks about what has happened to him so far. It is almost fantastic. He was raped, then beaten, then tortured. Then he was humiliated and forced to drink piss. Now he is tied naked to the bed, completely helpless. All of these thoughts cause Tommy to have a strange sense of arousal. His feeling of helplessness is, for some reason, a turn-on for him. If it were not for his chastity devise, he would have a full-fledged erection. As it was, however, the devise kept his penis tightly tucked between his legs which was very uncomfortable. This discomfort was nothing, however, compared to the lingering pain in his joints and all over the front of his body from the beating he had earlier.

Tommy hears what he thinks is a workout video and sounds of someone doing exercises to the instruction of the video. He figures that Deb is taking a break from abusing him and getting her daily workout in. The exercising goes on for about 45 minutes and after a while, he is sure that his assumption is correct. Deb is indeed working out.

The video comes to an end and Tommy hears Deb put away some equipment. He is getting nervous again because he realizes that now that she is done exercising she has time to focus on him again.

Deb enters the bedroom carrying a towel and a water bottle. She is covered in sweat. Her hair is braided into a tight ponytail and she is wearing spandex workout clothing. She leans against the doorway and say: "How's it going in there little boy? Are you having fun? Did you miss me?"

Tommy meekly replies: "Yes Ma'am".

"Well good, 'cause I am getting horny again. A hard workout always makes me horny," she responds and starts to walk toward the bed.

Slowly, she peals off her workout clothes and places them on the bed, real close to Tommy's face. He can smell her sweat and her unique BO waft from the clothing. She looks down at him sweetly as she gets on the bed and again straddles him.

"You look so scared, little boy. I almost feel sorry for you. But then I am reminded that you are a male, and I instantly stop feeling bad. I want to fuck you again, so get that little tongue ready for me."

This time, she turns around, so that she is facing Tommy's feet, and straddles his face. She lowers her ass directly over him and says: "Smell me!" Tommy does as he is told. He raises his head as far as he can and sniffs loudly so that Deb will know he is doing it. She smelled like a combination of sweat, sex, rubber and wet spandex. He is not too turned on by this, but that was probably a good thing.

Deb spreads her legs wide and Tommy can see her wonderful ass and moist pussy. Despite the smell, he can't help but marvel at the perfection of the female body.

"Lick me boy," she orders. "Lick me all the way up and down. I want you to sample the taste of womanhood at it's finest."

Tommy is grossed out at the prospect of having to lick her sweat-covered crack. But, realizing he has no choice in the matter, he obeys and runs his tongue from the front end of her vagina all the way back to the end of her ass-crack. The taste is very salty. That is mainly all he can taste. Salt and sex. He continues to lick and Deb begins to rhythmically gyrate as he does.

The next thing he knows, she sits down on his face with full force and continues to rhythmically grind her pussy into his face, faster and faster. Tommy's nose is pushed almost completely into her asshole and his tongue, which he is frantically trying to keep extended, is buried inside her wet pussy. She is moaning and thrashing about – faster and faster and finally she has a massive orgasm which causes her pussy muscles to contract and push gobs of pussy juice onto his already wet face.

She sinks back onto his face with her full weight, completely oblivious of the fact that Tommy can no longer breath. Thankfully, she dismounts him shortly thereafter and Tommy gasps for air. His entire face is covered his Deb's excretions. All he can smell and all he can taste is Deb.

She heads to her 'S&M' closet and retrieves, what appears to be, a double-sided dildo. It's the kind lesbians use sometimes when they both want to fuck and/or be fucked. Deb shows Tommy the dildo and says: "I need to be fucked, but I am not going to use this worthless thing," she slaps his penis which is still confined in its chastity devise. "I need something long and hard inside me and I want it not to be attached to a man. So 3; I am going to stick this into your mouth and ride your face again. You better be careful though, you might like having a plastic dick in your mouth," she says laughing.

Tommy is mortified. Will this ever end? He is reaching his limit. She sticks the dildo in his mouth and covers the other end with some K&Y. It is a large dildo and Tommy has to open his mouth wide to be able to take it all in. He worries that her riding motion might ram the thing down his throat and choke him.

Again she straddles Tommy's face and lowers herself onto the dildo. As feared, the downward pressure pushes the dildo far into Tommy's mouth and he gags loudly.

"You better not choke, or worse yet, puke. If you do, god help you!"

In shear panic, Tommy bites down on the plastic of the dildo and thereby stabilizes it somewhat. Now all the pressure of the fucking motion is being absorbed by his teeth.

Deb gets going almost immediately. She lets out noises like a star in a porn movie that Tommy once saw. She really seems to enjoy this. She rides the dildo (and his face) for several minutes until she again reaches orgasm and slumps over to the side of the bed, all spent. Her breathing is heavy and she has again worked up a good sweat.

Tommy merely lies there, afraid to do anything that might insight some wrath from Deb. After a few minutes, Deb gets up, takes the dildo out of Tommy's mouth, runs the other end (the end she had fucked) through his still open mouth to remove any pussy residue, and then puts her toy back into the closet. Next she comes over to the bed and removes Tommy's restraints.

Just as he is looking forward to getting up and out of there, Deb orders him to turn over onto his stomach and lie down again. Tommy immediately starts to quietly cry. He knows what is likely to happen now. Deb refastens his limbs to the bed and gets a cane from the closet.

"It's time again for more punishment, little boy. Your front is already covered in welts so I don't see the point in beating you there, but your back is still nice and pristine. I think I will go easy on you. You deserve about 100 lashes, but I think I will just give you 50."

Tommy cries out load at hearing this. He doesn't bother to plead or beg, but he cries in anticipation of the pain to come.

"You're crying? You should be thanking me. How would you like 100?" says Deb with an evil tone.

"Th-th-thank 3; yo-yoouuuu." Cries Tommy through his tear chocked voice.

Deb just laughs and begins to pound him with the cane. She counts almost in a singing voice and works her way from the bottom of Tommy's calves all the way up to his should-blades. She spends a lot of time on his ass and basically turns his rear into ground beef.

"You will NOT be sitting down anytime soon, I can promise you that!" she cheerfully announces having reached the count of 40. "Man, that has got to hurt!"

Tommy is in agony. He can no longer cry out load because the pain and exhaustion have taken his voice. He has sunk his teeth into the mattress and tears are streaming from his eyes. As each stroke impacts his body, he convulses from the pain. His whole universe is basically filled with pain.

When all 50 strokes have been given, Deb puts away the cane and again leaves Tommy in the room to recover. He has no idea where she went and has stopped wondering what is next in store for him.

About 30 minutes go by and Deb returns to the room, ordering Tommy to his feet after she unties him. She attaches the leash and leads him back into the basement area. There, she attaches his wrist-cuffs to a rope and pulley system under the ceiling of the room. She hoists his arms into the air and pulls until Tommy is standing on his tip-toes.

"Ok, I want to look you over," she says as she walks around his stretched-out body. She examines every part of him as if he were an object. "My gosh, you will not be able to show yourself in public for a while," she says laughingly. "If I were you, I would wear a lot of clothing – unless you want people to ask all sorts of questions. Shorts are out, t-shirts are out, and even short sleeves are a bad idea. And forget about sitting down. That would not be a good idea."

"So tell me, what have you learned so far today?"

Tommy is dumbfounded. He has no idea how to answer. He is silent and Deb can see the panic in his face.

"Well, let me help you along. What are you good for?"

Tommy thinks and says: "For nothing, Ma'am."

Deb laughs and replies: "Even though that is true in theory, we have seen today that you are good for somethings. Like, being a fuck-toy. And at crying. And at drinking piss. And at amusing me with your pathetic athletic performance."

"Now, what have you learned that you need to improve in?" asks Deb next

Tommy thinks frantically and answers: "I need to be faster at running with my hands tied."

"True," says Deb, "but there are many other things you should have learned, like that you need to toughen up so you don't cry so much; and that you need to be better at using your tongue on a Lady; and that you need to learn to control that nasty piece of flesh between you legs; and that you need to stop having any and all manly urges."

"You see, this is all part of your education. The other Ladies are teaching you certain things and I am reinforcing all of them while you are with me. The faster you learn how to be the perfect male, the quicker your pain and agony will end."

"I have one more thing I need to work on with you today. That is your orgasm control. You must have blue balls by now. So, I am going to introduce you to the 'Milking Post'."

"Lady Rachel had the Milking Box and this is similar in concept. You will be tied to the post and forced to hump the poll like a dog humps a leg. You will have a total of three orgasms in quick succession before you can be released. Hanging from the post will be most uncomfortable. And to help you recover between orgasms, I will be caning your raw ass each time until you are hard again."

As she is telling Tommy about the torment she is about to inflict on him, she is slowly turning his half-suspended body with her hands, forcing Tommy to make little ballet-type steps in order to keep his footing. The cuffs on this wrists are digging into his skin and his toes are becoming numb. Each time one of Deb's hands touches Tommy's skin, pain shoot from the welts left from the beatings. It seems there is no spot that has been left untouched.

Deb takes the chastity devise off of Tommy's penis and gently caresses his balls in her warm hand. She leans in real close to his face and whispers: "This is not going to be fun for you. You will suffer pain and more physical exhaustion. You will learn that orgasms are not a fun thing, but rather very bad and associated with pain and humiliation."

Tommy can smell her breath as she talks. That combined with her touch on this privates, give him an instant hard-on. Deb merely laughs and says: "You just can't control this thing can you?"

She lets Tommy down from his current suspension and leads him over to a wooden support poll that is approximately four by four in dimension. She has obviously prepared the area for her little task. There is a rope and pulley hanging down directly by the poll and there are several restraints on the floor waiting for their victim.

She orders Tommy to sit on the ground and place his legs around the poll so that his feet are together on the opposite side. (He is basically straddling this poll.) As soon as his butt hits the concrete floor, he screams out in pain. Deb giggles and ties his feet tightly together and orders him to stand up. Doing this is not easy. He has to pull himself up on the poll and try not to fall backwards in the process.

She attaches his cuffs to the rope and hoists his hands up several inches. Now he is suspended in a half-standing, half-sitting position. His penis is pressing up against the poll. His face is forced close to the wood as well and he can't decide if it's better to hang from his wrists or to try and stand-up straighter and take the pressure off.

The option to stand is quickly taken from him. Deb ties a thin piece of string around his ball sack and attaches the other end to his collar. Now if he wants to stand, he would have to severely pull on his balls to do so. He is left in the limbo position that is uncomfortable no matter what he does. If he lets all his weight go and just hangs from the cuffs, the pain in his wrists will become unbearable. However, standing in this half-seated position quickly causes his leg-muscles to become over-exerted and they begin to shack violently. Basically, he is in a virtual hell!

It gets worse though. Deb takes one of her vibrators and sticks it into Tommy's ass. The vibrator is set in the on position. "This well help you stay hard," says Deb in a short giggle as she rams the thing inside him.

Once she is satisfied with her 'installation' of Tommy, she steps back and looks at his helpless body. "One more item," she cheerfully exclaims and walks over to the bathroom. She soon returns holding a plastic bag filled with yellow liquid. "This is my nectar and you will drink it as you go through this exercise," she says as she fastens the bag onto a hook that has been attached to the poll near Tommy's face. She hangs the bag in such a manner that a corner is hanging down like a tip of a funnel. She takes out a safety pin and punctures the bag right at the tip of the low-hanging corner. Little drops of piss start to form immediately at the site of hole.

"Don't waste any. Drink up," orders Deb. Tommy puts his mouth on the corner of the bag and begins to suckle like a baby on a tit.

Deb pulls over a chair and orders Tommy to begin humping the poll. Tommy does what he is told and starts to gyrate back and forth with his penis. The friction on his dick soon becomes painful as his foreskin gets pushed up and his penis head is exposed. He does his best to keep pumping until finally, thankfully, he blows his cum all over the lower part of the poll.

He sighs deeply and sinks lower on the poll which immediately increases the pain in his wrists. Momentarily he forgets to suck on the bag of piss and a few drops hit his face and chest. Deb, noticing that he has cum, walks over to inspect his excretion.

"One down, two to go," she says happily. "You have one minute to get another hard-on and start pumping again or else I start to beat you." She looks at her watch and time begins to tick. The vibrator in Tommy's ass is still going full force, but the sensation of it is lost to the pain in his legs and wrists. Tommy tries everything to force his now limp penis to get hard again. It doesn't take very long and his minute is up. He knows it's up because he feels the first cane stroke hit his ass. The pain is terrible. He doesn't know in what direction to jump. His ass is still raw from earlier and these licks are now just hitting raw flesh.

He is near collapse and despair. He screams out between his tear choked cries: "Please stop. I don't care anymore – you can tell my mom what I have done and what a pervert I am. I just can't take it anymore. PLEASE STOP!"

At this, Deb stops. She walks around so that she can look at his face. Tommy's face is contorted in pain and covered in tears. He is almost unconscious.

"Well, I do believe I have reached your limit. That is what I was going for. Now you have a choice little boy. You have this one choice right now – if you want me to stop and to tell the world about you, I will. But there will be no going back if you say yes. However, since I have reached your limit, I will go a little easier on you if you decide to tough it out and learn to be a good little boy." She was sounding very serious now, for the first time today.

"So what do you say?"

Tommy thinks about his options. Neither seems appealing, but the thought of his mother finding out about all this and the look in her face when she see the pictures of him, is to much to bear.

"I will tough it out," he says weakly.

"Good," replies Deb, "because I would have told everyone – not just your mom – everyone I could find. And don't ever forget it. If you ever stop me like that again, it will be all over. Next time you don't get a chance to change your mind, so be really careful when and if you ever pull that one again."

She proceeds to pull the stool she was sitting on up close to Tommy. She sits down behind him and grabs his dick in her hand. Next she pulls out the vibrator from his ass, causing him to moan deeply. "I am going to help you cum the remaining two times. I will give you a prostrate message."

She starts to jerk off his dick and inserts her index finger into his ass at the same time. The next thing Tommy knows, he is shaking violently and spraying cum all over the place. He is shocked. He has never felt anything like that before. At the same time painful and overwhelmingly erotic.

Deb gives him a few moments to recover and does the same procedure again. Tommy is spent. He is just a bag of flesh hanging from the ceiling. Everything hurts. Now that Deb has abused his ass and prostate, his insides are throbbing, too. It feels like someone squeezed his insides clean of all fluid. His dick head is raw, his ass feels like it's bleeding and all he can taste is the piss that he just finished sucking out of the plastic bag in front of him.

Deb releases the tension on the rope holding his wrists and unties the string around his balls. Tommy slowly sinks down toward the ground fully aware of the pain that will strike him when his butt reaches the floor.

Sure enough, he whales out in pain once seated and falls over onto his side as soon as Deb releases his feet from their binds. She leaves him there for a few minutes while she puts away some of her 'toys\ she used to torture him.

"Ok, get up and clean up this mess," she orders after a few minutes. "I will give you a choice again. You can use your tongue and lick the poll and floor clean or else you can use a tissue. However, you will have to eat the tissue afterward if that is what you choose to use."

Tommy chooses the tissue option and begins to wipe off the cum residue from the poll and the floor. He is amazed at the amount of jiz he produced. Once he has cleaned the area and himself, he kneels at attention waiting for Deb to give him further instructions.

"Eat it," she coolly orders, and Tommy stuffs the tissue into his mouth and begins to chew. He has no moisture left in his mouth from all the crying and exertion so it takes him a while to get it down. Deb checks his mouth to make sure it is all gone and again attaches her leash to his collar. His is still not done, it seems. She has more planned for him 3;

It is getting late at this point. Tommy arrived at Deb's house around 3:30 and it's almost 8:00 now. Aside from all the obvious pain and discomfort he feels, he is now also noticing that he is really hungry. He wonders how much longer he will have to endure?

Deb leads him back into the bedroom. He can't imagine that she is horny again! This time, instead of tying his to the bed, she sits him down onto a small wooden chair with simple wooden armrests. She props his thighs over the side of each armrest and ties them in place, thereby spreading his legs wide apart. She ties his hands behind the back of the chair. She pulls up her stool and sits down in front of him getting as close to him as possible.

From a pocket inside her gown, she retrieves a few rubber bands and loops them around Tommy's penis and balls. Tommy is terrified and the old familiar tears again well up in his eyes. Deb leans in real close to his face, almost touching the tip of her nose to his, and says: "Little boy, I love to hurt you so much, I can't even tell you how it turns me on. You need to know and to feel that you are completely mine and at my mercy. Every inch of you belongs to me. I am your goddess. I am your everything. Your life is only to serve me."

Her face is so close that Tommy is breathing her breath as she speaks to him. At the same time she messages his penis and balls gently in her hands. He is completely helpless.

"I want you to see exactly how much I own you. While I hold your privates in my hands I will mark you as mine."

She leans even closer and gently licks across his face, starting at his mouth and moving up toward his forehead. Tommy feels owned! She has complete control of him. There in nothing she can't do. He is so hypnotized by her presence and her unbelievable feminine aura that his penis immediately gets hard. Pain and all, he is a puddle of emotions in front of her now. She continues to lick all over his face and at the same time holds his balls and penis in her hands.

Tommy gets so excited that he thinks he might actually cum right then and there. Just as he thinks he can't hold it anymore, Deb pulls back and tightens her grip on his balls. She looks at his erect penis and says: "Bad little boy," with a coy sound in her voice. She stretches the rubber bands far away from his privates and lets go. They snap back into place on top of his ball sack and cause him to scream in pain. His erection disappears straight away.

Deb giggles. She leans in close again and runs her tongue around his nostrils. He can smell her sweet breath and spit. It feels so good. She plays with his balls and runs a fingernail along the area between his ass and ball-sack. She is oozing sexuality. It seems every trick a woman has ever used to seduce a man is now being inflicted on him. His erection re-appears instantly.

SNAP – the rubber bands do their trick again. Deb giggles: "Bad little boy! Just can't keep his winky soft." She simulates baby talk while teasing him.

Deb continues to tease Tommy like this for several more minutes. He is both in ecstasy and agony. Finally, she stops and takes the rubber bands off from around his privates. "One day, you will be able to have me tease you like this and not get an erection, unless you are told to. That will be the day you are done learning," she says as he gets up.

"Now, two more things before you can leave." Tommy is overjoyed. He will get to leave soon. "The first thing will probably be the most painful thing you will experience all day today, I am afraid. But, it must be done. The second thing will be your entries into your log book which will take you a while I expect, given all we have done today."

Tommy is terrified beyond all belief. The MOST painful? After all that? What in the world will it be?

Deb goes back to the closet and return with a small tool box. She opens the box and takes out what looks like a knitting needle. Then she takes out a pair of rubber gloves and a bottle of sanitizing solution. She puts on the gloves and grabs Tommy's foreskin, pulling it far from the tip of his penis.

"You are going to wear a permanent chastity devise from now on and only the Ladies will have a key to get it off when they need your dick for some purpose. I am going to puncture a hole into your foreskin and put a small pad-lock into place. That way, you can't jerk off but you can still pee – albeit rather messily. You will likely have to sit like women do."

Tommy is beyond words. He opens his mouth to protest, but Deb cuts him off. "Save it. Unless you want this all to end right here and now and me to tell your Mom and the world, don't even bother to beg or plead."

Tommy closes his mouth again. He says nothing. Deb places a short wooden handle in his mouth so he can bite down on it while she pierces his penis. He braces himself and feels the unbelievable pain of the needle poking through both sides of his foreskin. Deb takes her sweet time doing it, too. She watches his face intently as he contorts in agony.

Once pierced, she rubs the disinfectant on the puncture and inserts a small pad-lock made of stainless steel into the holes. It clicks shut and his days of jerking off are over.

Deb releases Tommy from the chair and gives him his clothes back. He takes about an hour to finish making his log entries. He can't believe what he is forced to write. Deb spends a lot of time looking over his shoulder making sure she does not miss any details.

Finally, she adds her comments and sends Tommy on his way with his book and a new envelope containing the next Lady's name that he will have to serve.

Tommy pushes his bike all the way home – there is no way he can sit on the saddle to ride 3; not anytime soon.