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Subject: {ASSM} Story: "My Day with Mistress and Her Friend"
Date: Sat, 28 Oct 2000 12:10:26 -0400
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This story involves adult sexual content. FemDom, BDSM, oral, anal and spanking
themes. If this offends you then do not read it. Please direct any comments to
me at: p8730@aol.com (FF/m, B/D, D/s, spank, anal, oral)
"My Day with Mistress and Her Friend"
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 suffiencient 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
mischeavious 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 mesmurizing 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 manners!"
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
occassionally, 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 pre-cum
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 contined 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 gutteral moan escaped my lips!
"Thats two more punishments slave paul!"
I acknowledged my errors by saying I was sorry Mistress, and tried to muffle my
moans. Mistress Rebbeca 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 indescribeable 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 mis-deeds, 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 begining 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 breifly 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 mischiveous 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 resecured 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 grined 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 occassion, and it was not all of it's own doing
either! Lady Debbie was fondling my cock and balls, which were groing 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 genetailia! 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 alright 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
flesch!
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 smilling 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 seering 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 yeilding 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 dissapoint me in the future either!"
The cropping of my punished asshole continued, as Lady Debbie assulted 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, (pural), 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
gutteral 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 dialated 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
embarress 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 strap-on 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!
--
Pursuant to the Berne Convention, this work is copyright with all rights
reserved by its author unless explicitly indicated.
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