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 massage."

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.