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Today was to be like any other with Mistress Rebecca except that when I
arrived at Her dungeon home, their was a beautiful tall blonde woman there.
Soon I learned that this was Mistress's new friend and a new Domme. New to
the art of Dominating men that is!

Mistress informed me that I was to address this new woman as Lady Debbie
until She had sufficient training, than as Mistress Debbie.

I was more than nervous and intimidated around this beautiful woman. I had
never before "played" with an audience, let alone, another partner! I was red
with humiliation as Lady Debbie sized me up. She seemed to look right through
my soul, as if reading my deepest darkest secrets.

Mistress Rebecca informed me that today, Lady Debbie would be joining in on
our scenes from now on, and that she was briefed about my life as Mistress's
slave. I looked upwards and stole a glance at Lady Debbie's face. She had a
very mischievous smirk on Her face, that told me she knew everything about
me. Mistress must have told Her about my past year serving Her and all that
She had put me through!

Mistress Rebecca caught me staring at Lady Debbie's face and soon jolted me
out of my mesmerizing stare!

"Slave Paul, that is not proper behavior for a slave, you are obviously in
need of some correction I see!" "Deb, grab the slave's handle and lets get
him over to the horse!"

Lady Debbie took hold of my cock and yanked me down the hall. Once in the
Dungeon basement, Mistress stood next to the whipping horse holding the
cuffs. Soon, I was stretched out face down on the horse. My legs were spread
wide and attached to the cuffs on the spreader bar. My wrists were cuffed and
pulled back to my ankle cuffs and secured there too. Mistress Rebecca often
liked to secure me this way. She says it forces me to be more submissive, as
I cannot hold onto anything and the punishments are much more effective this
way!

Next, Mistress Rebecca tightened the waist belt which will hold me tight to
the horse. Mistress Rebecca handed the leather paddle to Lady Debbie, who was
now standing directly in front of me.

"Here you go Deb, I think you should have the honor of doing him first,
since it was you he was staring at so disobediently!" "I will just hold his
head right here and put his tongue and mouth to good use while you teach his
sorry butt some mColletters!"

Mistress Rebecca the grabbed the back of my head and forced Her crotch into
my face! Her heady scent was strong as it filled my nostrils! I stuck out my
tongue and began to lick her wet lips and taste her secretions! I was soon
brought back to reality when Lady Debbie's swats of the paddle sent a sharp
stinging pain through me. Over and over again Lady Debbie swatted and paddled
my butt. My oral attentions had Mistress Rebecca moaning in delight, and soon
She flooded my face with the wave of her juices. Mistress let go of my head
as she sat down briefly to recover from her orgasm.

"That should be enough correction with the paddle Deb, why don't you get me
the crop over there now." "But first, I think my little slave needs to be
properly plugged before we continue with his respect training!"

I watched in horror as Lady Debbie took down the riding crop from it's
hanging spot on the wall. Equally alarming was seeing Mistress Rebecca make
her selection from the tray of vibrators, butt plugs and dildos. She was
holding one of the widest and longest plugs we have!

Mistress Rebecca was instructing Lady Debbie on how to use the plugs and
dildos and to make sure the toys are properly lubed. Mistress Rebecca told
Lady Debbie that normally, some type of lubricant will be used on my hole and
the toys, but occasionally, if she really wanted to add to my punishment no
lube would be used!
This time however, Mistress Rebecca was smearing her own juices around my
tight puckered hole. Lady Debbie was also busy, but she was milking out the
precum from my cock and applying the cream to the butt plug! Then, Mistress
Rebecca was instructing Lady Debbie to hold my butt cheeks wide apart and
watch close as she worked the plug into my hairless tight hole!

Mistress Rebecca took her time teaching and showing Lady Debbie the fine
points of tormenting my rear hole. She would push just the tip of the wide
plug into my hole, then twist and rotate the plug as she drilled it in
deeper. She would stop right when the widest part was stretching my anus as
wide as possible and just hold it there. I was moaning as the pain felt like
I was being ripped apart!

"Your moaning is too loud slave!" "You have just earned additional
punishments that you will receive after the cropping!"

I tried to tone done my moaning, but Mistress Rebecca continued her one on
one training with Lady Debbie! Mistress would hold the plug so the widest
part just stretched me painfully, then she would pull the plug all the way
out. Then push it in again to the wide part and hold it there while she
discussed her instructions with Lady Debbie! Finally, she just shoved the
butt plug deep into my hole and a loud guttural moan escaped my lips!

"That's two more punishments slave paul!"

I acknowledged my errors by saying I was sorry Mistress, and tried to muffle
my moans. Mistress Rebecca then placed her hands on my hot butt cheeks, and
told Lady Debbie to give it a try. Then I felt Lady Debbie grab the plug, and
under Mistress Rebecca's instruction, she twisted and rotated the plug as she
pulled it out! The feeling was indescribable as she pulled the plug from my
tormented anus. I could not help it as another moan filled the dungeon!

"Now there are three additional punishments waiting for you paul!" "Deb, you
must never allow the sub to get away with his disobedience!" "Always hold
them accountable for all of his misdeeds, even if he can't help himself!"

I knew Mistress Rebecca was smiling when she said that! Mistress loves to do
things to me that causes me to react in her favor. She will push me till I
break a rule or disobey one of her orders, only to punish me afterward. My
Mistress enjoys punishing me because she loves to watch me squirm, and she
loves to inflict pain on me, the more the better! This is her enjoyment in
our D/s relationship, and mine is not knowing what she will do to me next!

Lady Debbie was now repeating the steps she watched Mistress Rebecca do to
me. First she pushed the huge butt plug into my hole until the widest part
was stretching me open. Then she rotated the plug which caused me to squirm
and moan again! This was different then what Mistress Rebecca had done and
Lady Debbie was just holding the plug at the widest part stretching my anus
wide, and then twisting the plug back and forth and back and forth, but never
moving it in or out! I was moaning loud again when Mistress Rebecca chastised
me!

"You are not being a very good slave paul, and you are beginning to annoy
me!" "We have a new guest and you are continuing to break the rules!" "You
now have four punishments coming, and since you insist on being disobedient
in front of Lady Debbie, I will make sure that we both deliver them to you
and they will be severe!"

With that said, Lady Debbie then began to fuck my hole with the huge butt
plug, but with a new technique! Lady Debbie would just push and pull on the
butt plug, but not allow it to move very far into my hole. This way she was
just forcing the widest part of the plug in and out of my stretched anus!
Over and over Lady Debbie continued to force the cone in and out of my
tormented asshole! I was moaning softly as my Mistress and her friend
punished my hole.

"You seem like a natural, Deb!" "You must be causing my slave some nice
torments, by the way you got him squirming and moaning!" "You will have to
punish him good for the way he tried to leap up when you twisted that plug in
his butt!" "I think it is time to finish his cropping, it looks like he has
earned enough punishments to keep us busy disciplining him all day!"

I felt the plug being pushed deep into my but, and then Lady Debbie twisted
it back and forth again, while pushing it hard into my hole! I could only
moan and tremble as she did this for a few more seconds before stopping!"

I rested briefly while Mistress Rebecca told Lady Debbie to have me orally
service her. Mistress picked up the crop and told me that she would punish my
butt now for my earlier offense of starring rudely at Lady Debbie! And, that
I should do my best to give Lady Debbie a nice orgasm, only then would the
cropping stop!

Lady Debbie picked up my head and whispered into my ear that she loved
tormenting my asshole, and that she has many more wicked plans in store for
me! She then placed my head tight against her very wet crotch! I inhaled
deeply her strong womanly scent! She tasted much sweeter than Mistress
Rebecca, and I lovingly licked and sucked her pussy for all I was worth!
Mistress Rebecca was busy raining down swat after swat on my sore bottom!
Each swat seemed to cut into me, and my ass was on fire from the punishments!
It was hard to concentrate on pleasing Lady Debbie, but I pushed my own
limits until Lady Debbie was howling in her own thrones of passion! I felt
Lady Debbie release my head as she slumped into the chair in front of me, her
eyes connecting with my own and that wicked mischievous smile on her face!
Mistress Rebecca was giving me a few finale swats before she stopped her
assault on my poor punished and flaming behind!

I was breathing heavy and sobbing as the tears ran down my face washing the
wetness from two sexually satisfied women's orgasms. Mistress Rebecca told me
to stay right where I was, because after a short break she was going to start
with the four punishments that I have earned! "Stay right where I was", I
thought? Where could I go? Mistress likes to torment me in so many ways!

Lady Debbie got up and stood next to my head. I could still smell her aroma
as she stood close to me stroking my hair. She bent down and whispered into
my ear as her hand found my dripping cock!

"I know just what to do with naughty little slave boys like you paul!" "And
this poor little cock is going to be punished when I get my turn on you
paul!" "Your moans will be nothing like the ones when I teased your little
butt either!"

I shivered in anticipation of Lady Debbie's threats, and as her words were
whispered into my ear, my cock was swelling in her hand! I couldn't help
myself, the she was warning me of the intense pain my cock would soon be
feeling, and it was growing larger as she was speaking! Lady Debbie just
chuckled and laughed as she let go of my member and got up to check on
Mistress Rebecca. As Lady Debbie walked behind me, she paused to toy with the
butt plug again, and she pulled on it and twisted it back and forth again!
Then, while I was moaning louder again, she slapped my red stripped butt
cheeks hard, as she walked away!

After a short rest, my two Mistresses walked back into the dungeon looking
all refreshed, and to my worry, ready for much more!

Mistress Rebecca stood on one side of me while Lady Debbie was on the other.
They both began to release me from my bondage, and helped me to my feet. I
was lead down the hall to the bathroom and told to relieve myself, but to not
touch the butt plug. I accepted the warnings and hobbled as best I could with
the large plug embedded deep in my butt. After my brief pit stop, I was
ushered back into the dungeon where I was commanded to stretch out back on
the horse, this time face up!

After Mistress Rebecca re-secured me in the new position, she proceeded to
inform me of how rude I had acted in front of our guest. I watched as Lady
Debbie just smiled and grinned as she knew my punishments would be cruel!
Mistress Rebecca reminded me that I would now receive four punishments for
disobeying her and acting rudely in front of our new guest.

I watched again in horror as Mistress Rebecca retrieved the short penis
whip. This whip was a multi-braded leather whip. The tails of the whip were
soft suede leather, much like those you see on a fringed jacket.

My cock was rising to the occasion, and it was not all of it's own doing
either! Lady Debbie was fondling my cock and balls, which were growing
steadily larger. I was about to protest, and beg and plead with Mistress
Rebecca for mercy, but I know that would only worsen the situation for me.
Once I have earned a punishment, Mistress will not ever back down or allow me
mercy. I learned the hard way many times before, that if I earned the
punishment, then I must accept it. In the past if I had begged for mercy,
Mistress would double or triple the punishment just because I asked her to
stop! I knew that would not work this time either!

Mistress Rebecca handed the short whip to Lady Debbie and told her she would
have the honors of starting with this punishment! And while Lady Deb was
whipping me, Mistress straddled my face and lowered her crotch over my mouth
and nose! Mistress Rebecca then told me to put my tongue and mouth to good
use, while she observed Lady Debbie! Since Mistress was facing my penis
punishment, her asshole was planted right on my nose. I was forced to inhale
her back door deeply as the first crack of the whip caused me to gasp! I
tongued and sucked at Mistress Rebecca's hole wildly! But there was no way to
move my head or my nose. I was trapped and forced to inhale my Mistress as
she just settled in for the ride!

Lady Debbie was enjoying her time with the whip! I was being expertly
flogged from my balls to the tip of my cockhead! Over and over the swats
would move all around my genitalia! My hips were bucking with each contact of
the whip, but being securely tied down I was just jerking to the touch of
Lady Debbie's whip. Mistress Rebecca was rocking on my face now, and each
time she would pivot, she would just grind my nose farther into her asshole.
My head was reeling from the mixed smells of her pussy and asshole invading
my senses!

Without warning the swatting at my crotch had stopped and Mistress Rebecca
was climbing off of me. Next, she came over to me, my face shining from her
juices, and in her hand was a wash cloth. She wiped my face clean and spoke
about how we can't have a messy face for our guest to mount now can we?!

But before Lady Debbie climbed aboard, she was holding a set of the nipple
clamps and asking Mistress Rebecca if it would be all right to use these.

"That is an excellent idea Deb!" "Why don't you work his nipples good with
these, and I will have a go at his penis with the whip"!

Lady Debbie took her place on my face, and after she settled down, her
asshole was pressed tight against my nose too! The two Mistresses were
definitely different as Lady Debbie's pussy tasted great and her asshole was
stronger and more pungent then Mistress Rebecca's!
Suddenly, I moaned loudly into Lady Debbie's pussy, as both the whip lashed
out at my penis and the nipple clamp was cutting into my tit! Mistress
Rebecca was standing on the opposite side that Lady Deb was on, and now my
cock and balls were being attacked from a different angle! Another loud moan
shot up through Lady Deb's pussy as the other clamp bit down into my nipple!
Then Lady Debbie started to twist and pull on the nipple clamps, forcing them
to bite into my flesh!

Soon, the pain in my nipples subsided or the pain in my crotch became more
intense! But all I could think about was making my punishment stop! I was not
even conscience about my oral servitude at the moment, as my cock and balls
and even my nipples were fading into numbness! And like my Mistress had done,
Lady Debbie was slowly rocking on my face, and I could hear her moaning
loudly. I must have made her cum as my mouth was being flooded by her juices
and I had to swallow repeatedly to drink down her cum!

The next thing I realized was that my penis whipping had stopped, and lady
Debbie was standing beside me smiling down on me! I was untied again and
allowed to rest for a few minutes. I looked down at my swollen cock and
balls, and they were completely red and stripped from the whipping! The
nipple clamps were still on me, and I suddenly realized that the butt plug
was still inside of me! I was covered in sweat, and grabbed a towel to dry
off.

Mistress then told me to wipe down the horse and stretch back over it, face
down!

I did as I was told, and once again my Mistresses reattached the cuffs and
secured me to the horse.

"Well, paul, I see you have taken two of your punishments so far, ready for
the next one?"

Two, I said questioning my Mistress?? I thought that I was on number three?

"Well, technically, number three isn't quite over yet, so we really can't
count it yet!"

With that, Lady Debbie released the nipple clamps and then pinched my
nipples as the blood flowed back into them! I howled in pain when that was
done, only to the delight of Mistress Rebecca who was right there to rain
down swat after swat with her crop on my already sore and inflamed ass!

"Paul, now you know we can't have you screaming out like that!"

I accepted her additional swats with the crop, which caused me to jump once
again as they renewed my already sore and tender butt!

"Deb, why don't you remove that plug that has been stretching paul's hole
for so long". "We don't need that in the way of his next punishment!"

Lady Debbie was teasing my asshole again as she first twisted and rotated
the butt plug before trying to pull it out! Then she pulled on the plug but
was purposely pulling the plug out very slowly, allowing the most pain and
agony she could inflict on my poor stretched hole! Once again, she stopped
when the widest part was at my anus stretching it to the limit! Then finally
it was out!

Mistress Rebecca had an "Ace" bandage in her hand as she grabbed the butt
plug from Lady Debbie.

"This is how we stop a whiny loud slave Deb!"

Then Mistress shoved the hot butt plug under my nose and told me to open
wide! I hesitated for only a minute as the crop was swatted across my butt
very hard! I opened my mouth as the wet plug was shoved into me. I was about
to gag, but soon adjusted to it's size. Mistress then went about her duty of
wrapping the Ace bandage around my head to hold the plug in place!

"There, that will keep him quiet while he receives his next punishment!"

Once again Lady Debbie reattached the nipple clamps and my moaning was very
loud this time, as the pain seared through my chest!

"Yes, paul, go ahead and scream, the gag will keep you down to a muffled
moan!" "By the way, you were right, the nipple clamps were punishment number
three, but I think we will just keep on re-tormenting them anyway!"

Next, Mistress instructed me to accept the cropping on my butt as punishment
number four! I was confused at first, because my ass was already beaten as
punishment. But then I felt a set of hands pulling my punished butt cheeks
wide apart. Then a new searing pain shot through me! Mistress was cropping my
ass crack, and the first few swats landed directly on my punished asshole! I
was jerking wildly with each swat. Mistress aimed each swat to really hit the
target and I was jerking and flopping and howling into my gag!

It stopped just as quickly as it started, but then the nipple clamps were
removed again! My nipples were rubbed, pinched and twisted as the hands were
working the blood flow back into them! Then the nipple play stopped too, and
the hands were now pulling my butt cheeks apart again. I can only assume that
Lady Debbie was yielding the crop now! These swats were much harder than
Mistress Rebecca's, or so they seemed. Over and over again, I jerked and
twisted in my bonds trying to get free or get away from the swats! Nothing I
could do would stop this punishment, and then I heard Mistress talking again!

"You will learn paul, I told you that your punishment would be severe!" "I
hope you will not disappoint me in the future either!"

The cropping of my punished asshole continued, as Lady Debbie assaulted my
crack with the crop! Over and over again! I was so glad when my Mistresses
stopped! I was ready to agree to anything to not let them crop me again!
Mistress Rebecca told me to relax and rest for a bit before accepting my
final punishments!

The word punishments, (plural), rang through my head! I wondered just what
it would be and how much more could I take!

Then I saw them standing before me, my Mistresses wearing two of the biggest
strap-on dildos we have!

"You will surrender your butt to me now paul!" "I know how much you crave a
good dildoing, that is why I needed to punish your little asshole first, so
you will remember that this is your punishment, not for your pleasure". "This
will be an equally severe punishment paul, as we are going to rape your
asshole with these big dildos, nice and hard and long!" "And when Debbie is
done punishing your hole, I will have my turn at raping your hole and reaming
your butt very good!

As the butterflies were churning in my stomach, I heard Lady Debbie talking
to me too!

"Yes, paul, and remember when I told you I had a special surprise for you?"
"Well, I am giving you a special treat by using lots of lube on this huge
dildo for you!" "It might smell funny, that is because the lube is "Vick's
Vapor Rub"! "I do hope you will thank me later with a nice long oral service
like before?" I will be sure and leave one of these huge dildos embedded deep
in your hole while you service me too!" I wouldn't want to leave a hole
gapping open like that, it is so unbecoming, don't you think so Becca?"

Mistress just laughed and chimed in about Deb's wicked mind being equal to
her own!

Then Lady Deb's huge shaft entered me. The Vick's was very cold at first,
but the pain from stretching my very sore asshole soon had my complete
attention! Then I realized that Deb was working the dildo deep into me! With
each stroke she drove the huge shaft deeper into my rectum. Finally I felt
her hips and thighs against my hot buttocks! After waiting for a moment or
two, she pulled out, all the way out, and then she let me have it! Wham, all
twelve inches were shoved hard into me! Again, full deep thrusts as Lady
Debbie pulled out completely then rammed her strap-on in to my depths! Each
hard thrust caused me to gasp into the gag, and it was a strange sound as the
butt plug muffled my guttural moans! I lost track of the time, and it felt
like an eternity while Lady Debbie hammered her massive dildo into my
punished and abused asshole! The Vick's had caused a hot burning itch deep in
my rectum which made me yearn for another thrust, like an itch I couldn't
scratch!

Then I felt a coolness and a void back there, as air was passing into my
stretched and dilated hole. I wondered if my Mistress tag team was switching
partners when The searing clamps were put back on my nipples! Owwwie, tried
to come out of my gagged mouth. Then Mistress Rebecca was at my asshole, her
strap-on just touching my hole. Then without warning a new invader plunged
into my depths! Like Lady Deb, Mistress pushed deep into me, making the
entire length penetrate my punished hole! With each deep thrust of Mistresses
dildo, my inner rectum seemed to heat up, and that itch was back tormenting
me! First the itch then the deep plunge of the strapon as it stretched and
reamed my hole! Yes, my Mistresses raped my asshole very good, or very
severely!

I was one punished slave when my Mistress released me! The tears had left my
face wet with shame. Mistress Rebecca removed my butt plug gag and I
immediately thanked her and Lady Deb for punishing me! I repeatedly said I
was sorry for everything that I did, and I would never again displease her or
embarrass her the way I did!

Mistress then told me to kneel before Lady Deb and give her a very nice long
oral orgasm!

Lady Debbie was true to her word too, because as I kneeled before her, she
handed her huge dildo to Mistress Rebecca, and told her to bury it deep!

I moaned aloud when Mistress did just that! Then I spent the next twenty
minutes lovingly licking and sucking Lady Debbie's delicious pussy!

Later that night, Mistress Rebecca finally removed the nipple clamps, and
offered me an orgasm for being a good slave. I squirmed in pain as Mistress
rubbed and stroked my punished cock, but I was able to have a very nice long
orgasm myself, which left a larger than normal puddle of cum in Lady Debbie's
hands! Mistress then commanded me to clean Deb's hands with my tongue as she
slowly removed the huge strapon from my raped asshole! Mistress commented on
how wide open my hole was, and Lady Debbie leaned over to see also!

I was ordered to clean up the dungeon and the toys, and shower before being
allowed to sleep. Tomorrow, Mistress promised another fun filled day with
Lady Debbie!

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