THE LADY'S CLUB

BY ZORK2006

[ part 4 ]

Tommy wakes up the next morning still groggy from the previous evening. The pain all over is body is now constant and all encompassing. Even though he knows that his recollections of the events are real, part of him thinks he just had a bad dream. The very real pain, however, brings him back to reality.

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 friends 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 10 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

On Friday after leaving school, Tommy heads over to Deb’s house at the time she ordered him to appear. He parks his bike next to her house and heads for the front door. After ringing the doorbell, he hears from an intercom speaker “Boys are not allowed to enter in the front – walk around back to the lower patio and strip. Wait for further instructions.”

“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 10 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 4 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 2 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 2 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….”

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 4th 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 6 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 9th 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…..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 3 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 3 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 10th 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 2 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 2-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….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 chock 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…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 3 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 4 by 4 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, 2 to go” she says happily. “You have 1 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 2 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….

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, 2 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….not anytime soon.