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My Mean Boss

I was lucky to get this job since I didn't have great grades in school in
spite of spankings by my parents for bad grades. They at least respected my
modesty by having me go to my room and putting on my pajamas before going
back down to lean over the back of the couch for my spanking. They just
used a ping pong paddle which wouldn't have been too bad if there hadn't been
so many spanks. They based it on my grades. "A" no spanks, "B"20 spanks
"C" 30 spanks and "D" 40 spanks.
Unfortunately I usually got Cs and Ds so with five classes I always got
more than a hundred. By the time they finished I would be bawling like a baby
and my poor butt would be deep red and stinging, burning and throbbing all
at once. When done I was told to go to bed and the only thing that helped
was rubbing my butt.
I often had to rub for an hour before it stopped hurting.
Anyway I got a job as a receptionist and felt proud when they thought I
was capable of dispensing the petty cash from a locked drawer in my desk.
The other girls teased me about my frumpy clothes but Mom had bought my
clothes with the long skirts and loose blouses. Even if I could have afforded
to buy new clothes I wouldn't have bought the slutty skirts they wore which
came up to mid thigh. Mine well below the knees were fine. Mom had told me
it was important to be modest and I saw it was true by the way men leered
at the other girls but treated me with respect.
The job did not pay very well so I was broke by payday in spite of
skipping lunches. I lost weight but I have a weird body. I only lost weight in my
stomach and my 36D boobs and 36 in butt looked huge next to the tiny waist.
It embarrassed me so much I covered up the bottom part of my mirror so I
could only see myself from the neck up.
Then disaster struck. My car broke down and I lived too far from a bus
route to get along without it. When the mechanic called me to tell me the
repair bill I realized I was a hundred dollars short of being able to pay it.
I decided to take a hundred from the petty cash drawer and pay it back by
payday. They never counted the money my boss would just put more in the
drawer when I told him it was running out.
Unfortunately I had to have a tooth filled and couldn't pay it back payday
or the next payday.
On Friday my boss told me to come to his office after work. I really hoped
it was to tell me I got a raise in pay since I was so broke.
He was sitting behind his big desk and waved me to a chair in front of
him. When I was seated he said, "You may not know this but every night before
I go home I check your petty cash to see if I need to stop at the bank to
replenish it."
I knew I was in trouble and stammered, "Iii can explain."
"Shut up and let me finish."
I slumped and nodded.
"Two weeks ago I found you were short a hundred dollars in the accounting.
I gave you the benefit of doubt and assumed you had forgotten to document
it but it has been two weeks and you are still short so I can only assume
you stole the money. Don't come to work Monday I will call the police and
tell them to arrest you at home to save you some embarrassment. It is a shame
even after you get out of jail you will have a hard time getting a job
with a prison record."
I cried, "Oh please don't do that. I'll pay you back. I'll pay double."
It is too late for that besides by having you arrested the insurance
company will pay the loss."
"Oh please! Can't I make up for it in some way. I'll do anything!"
"If you are offering sexual favors, forget it. You could be trying to trap
me and sue me for sexual harassment."
"Oh no I wouldn't do that. I was thinking of you punishing me in another
way. My parents spanked me when I was bad. Could you be satisfied with that?"
He looked interested and said, "Maybe we could work something out.
Describe your
parents spanking."

I blushed realizing I had never told anyone about being spanked even my
best friends but I had started this so I said, "On the day I was to be spanked
I had to go up to my room and put on my pajamas. When I came back down
there would be a dining room chair in the center of the room. I had to lean
over the back and hold on to the seat for the spanking."
"I see. What did they use to spank you."
"A ping pong paddle."
"Did that hurt?"
"Yes! I only had the thin pajamas and my panties to protect my bottom."
"How many spanks would you get?"
"Up to a hundred. My poor bottom would hurt until the next day."
"So you would be willing to take a hundred spanks to make up for the
hundred dollars?"
I thought that was really reasonable since stealing was much worse than
bad grades and said, "Oh yes if it will make you forgive me."
"From the clothes you wear and the fact your parents allowed you to be
fully covered in pajamas you are evidentially quite modest. Right?"
"Oh yes. I even waited to shower at home after gym classes."
"Well I am sure you agree that stealing is much worse than anything your
parents spanked you for doing so to make your spanking worse you will be
completely nude for it. Do you agree."
"Oh no. Please! I would die of embarrassment."
"No-one can die from embarrassment although it would add to your
punishment both by the humiliation and the sharper sting of spanks on nude skin. But
it is your choice. That or Jail."
It was an awful decision. I had never been nude in front of girls let
alone a mean old man but even that would be better than going to jail.
I whined, "If I have to. I will."
"Good but I will take no chances on being sued later. Look behind me and
you will see a security camera. I want you to look at it and say, "I am very
sorry I stole money from you and to make up for it I want to take a hundred
spanks on my nude body."
I understood. I had read about girls collecting huge amounts of money for
sexual harassment although I saw nothing sexual about spanking. My voice
kept breaking so I had to repeat it several times before he was satisfied
even adding "Please spank me" at the end.
He said, "Follow me into the conference room and I blanched thinking it
was going to happen."
In the conference room he said, "It may surprise you to know that other
girls have preferred spanking to losing their job so I have gathered some
instruments for that purpose."
He opened a cabinet and started laying scary things on the table. A paddle
about the same as a ping pong paddle except it had a much longer handle
and had holes drilled in the paddle part, a long thin bamboo cane, a 36 inch
really thick ruler, an 18 inch long leather strap, and scariest of all a
whip with five tightly braided thongs like small ropes.
He allowed me to stare at them in fear for a moment and then said, the
paddle, cane and ruler is for fleshy parts like your butt and thighs. The
strap and whip may be used anywhere on your body."
I knew I would have to choose the paddle, cane, or ruler because I
could not
conceive of being hit on places like my tummy or shocked at the thought
of my
breasts or
crotch.
I whined, "It is an awful choice to make. All of them look as if they
would hurt a lot more than a ping pong paddle. I am sure I may faint before you
finished a hundred with any of them."
"Oh I agree. You would either faint or become so numb it would no longer
hurt so we will have five sessions of twenty spanks each. Monday, Tuesday,
Wednesday, Thursday and Friday."
It would be a long terrible week but I thought it would only take seconds
to give me twenty spanks and said, "Yes. That would be better."
Good but since you are undecided on the instruments I would like to give
you one spank with each so you will know what they are like. Do you agree?"
"I guess I should know before I commit myself to twenty."
"Good. On bare skin. Do you agree?"
I was hoping to put off that ordeal but I knew it would have to be that
way. I gulped and said, "I guess it is the only way I will know. Will these
count toward the total?"
"No this is for your benefit so you will know what they will feel like."
"Oh that doesn't seem fair but okay."
"Fine but there should be no doubt this is your idea. Face the camera and
say,' May I please take off my clothes so you can hit me with each one so I
will know how they feel."
God. It seemed like the minute I agreed to one indignity it was followed
by another. I was so nervous it took three tries to get my speech right.
When he was satisfied I looked sincere he said, "Okay. You may disrobe."
I stalled taking things off slowly and folding them to put them on the
table not realizing my slow strip was good for him. When my blouse, skirt and
slip was off he said, "Jesus. You have a beautiful body. I assumed you
would be fat."
That both pleased me and embarrassed me. Nobody had ever said I was
beautiful before but no-one had ever seen me so naked.
When I took off my bra he was again pleased saying, "Great your big
breasts have hardly any sag."
They didn't sag since they had been supported for years with my big bras.
I just nodded at the compliment and blushed.
He was not so pleased when I took off my panties saying, "That is
the hairiest crotch I have ever seen. Don't you ever trim it?"
I blushed and said, "No I thought it is the way nature intended."
"Fuck nature. This weekend you will trim it."
I had never touched my crotch except the quick washes in the shower. The
idea of standing in front of a mirror to trim the hair made me blush even
deeper.
Then he had me bend over to grab the end of the table and made me say,
"Please hit me with the paddle." I heard a "Whish" as the air went through the holes then the worst pain I had ever experienced as it splatted against my butt cheek. It was much
worse than the ping pong paddle and tears came to my eyes with my shriek.
I rubbed my bun to lessen the sting then I had to say "Please hit me with
the cane."

He hit my other cheek with it and it was also horrible but different.
It seemed to cut into me deeply to make the pain go deeper causing another burst
of tears" I rubbed both cheeks then had to say "Please hit me with the ruler."
I looked at him and he held the long ruler in both hands like a baseball
hitter and brought it back behind his back. Then it was a blur followed by
terrible pain. He had hit across right at the crease where my bottom meets my
thighs. It must be an especially sensitive spot since that one hurt the
most so far. It caused me to dance and sob and rub all at the same time.
He let me calm a little then had me say ,"Please hit me with the strap."
He had me stand up facing the camera then stood beside me. He told me to
tighten my stomach muscles and I sucked in my tummy.
He hit across my tummy just above my pubic bone. It really stung and left
an angry red stripe but actually it was not as bad as the ruler. I had been
able to absorb that pain with just a gasp so he had me say," Please hit me
with the whip."
He told me to put my hands behind me and to pull my elbows close together
and suck in my tummy. It made my breasts stick out and was cruel. I
expected to be hit again on my tummy but the whip came in a blur to snap into my
breasts flattening and jerking them causing pain to radiate all through my
body. I caressed my poor stinging and throbbing breasts with the angry red
stripes not caring that he was watching with great interest..
He allowed me to dress which returned my modesty but the bra irritated
the stripes especially the one across my nipples which had swollen to look
like a couple of little thumbs.
When I was dressed I wanted to leave but he said, "What will you do to
prepare yourself Monday?"
I remembered what he had said about my crotch hair and said softly, "I
will trim my crotch hair."
"It is not your crotch hair it is all your cunt hair and I have changed my
mind.
You will shave every hair off your cunt. I want you to look as if you were
4 years old. Say ,'I will shave every hair from my cunt and asshole. If I leave any I will get another spank for each hair."
I recoiled at the term "cunt." as I had only heard the word as a very
derogatory term and the thought of being that naked appalled me.
I whined," Can't I just cut it short with scissors?"
"No. Say, 'I will shave my cunt so you and the witnesses will see every
inch of my slutty cunt."
The word witness scared the hell out of me. I cried, "Witnesses! You
didn't say anything about anyone but you seeing my shame!"
"Oh it won't be many. Just my partner and some girls that were also
spanked. Now say it!"
I thought at least the other girls would feel sorry for me and with a
sick feeling I said ,"I will shave every single hair from my cunt and asshole so you and everyone can see my slutty cunt."
That finally satisfied him and he let me go home.
When I got home I could hardly wait to get the clothes off that were
irritating my welts and filled the tub with soothing lukewarm water.
While I soaked I thought about my horrible experience and dwelled on the
fact the whole next week would be painful and degrading. I should have hated
him but I hated myself for stealing to make punishment inevitable by
either him or the court. Then I remembered reading about the jails being
rampant with homosexuality and that butch dykes ****d other girls. That convinced me I had made the right choice no matter how painful and degrading it may be.
Finally all the stinging sensations went away leaving only a throbbing
sensation in my breasts that was not unpleasant. I remembered about my crotch hair and got a scissors and razor. I cut the hair as close as I could with the scissors and then shaved it. I had never touched my vaginal area so
much before.
In spite of myself I began to enjoy the feeling of my fingers holding my pussy lips tight while the razor glided over my skin. That made me feel guilty and
when I was done I whispered, "There you nasty cunt. Now they can all see
you."
For the first time since I had moved into the apartment I removed the
curtain covering the full length mirror on the closet door and looked at
myself. It was amazing how naked the loss of the hair made me and I blushed although I was all alone.
On Sunday I remembered about the penalty for any hair missed in shaving
and since it was so close to he ordeal I had caused I decided to punish
myself by pulling the few remaining hairs with my eyebrow plucker. It hurt and I
made it hurt more by slowly pulling on them until they ripped out. I even
squatted over a mirror to pull any I found around my asshole in spite of the
tears that came to my eyes.
Although I never drank I decided a drink may help me stop dwelling on
tomorrow so I decided to go to the corner liquor store to buy a half-pint of
whiskey. I thought that since I now looked like a slut I would act like one
and decided to go to the store with no underwear. I didn't want anyone to
know though so I put on one of my heavy long wool skirts and a wool bulky
knit sweater.
It turned out to be a wild experience. I had never gone without underwear
before and my naked legs and butt and breasts rubbing on the wool strangely
excited me.
When I bought the whiskey I impulsively picked up a mans magazine
blushing as I
told the clerk it was for my husband and when I got home I took off my
clothes
and compared myself to the girls in the magazine
To my surprise my weird body seemed to be the ideal and all of them had
shaved pussies. I began to think that maybe I should be proud to show my body since the girls in the magazine were probably paid big money to show
themselves.
The whiskey didn't help much and I was not able to convince myself it was
alright to be naked in front of the people in the office. It did help me
sleep though and the next thing I heard was my alarm going off at six since
he had told me if I was late for work he would assume I had changed my mind
and would send the police for me.
Even though I took a long shower and spent extra time with my hair and
makeup I still got to the parking lot at 8:00 AM and had to wait dwelling on
what was to come. I still had not made up my mind on the instrument. From
the marks on my body it was obvious the strap and whip caused the least
amount of damage but on the other hand it would allow them to hit my most
sensitive places. I decided to wait until the last minute but thought I would
probably go for the ruler or maybe the cane.
Finally it was 8:30 AM and the doors were unlocked.

MY MEAN BOSS 2
==============
I went in and sat at my desk thinking the seat may not be as comfortable
the next day.
My Boss came in about 8:15 and told me to follow him to his office.
At his office he did not tell me to sit down so I nervously stood in front
of him.
He said," Obviously you have decided to accept your punishment."
I hung my head and said softly," Yes. I thought about it all weekend and
decided I should be punished and degraded. If it hurts bad I deserve it."
"Good girl."
That seemed to be his favorite thing to say when I agreed to pain and
humiliation. Weirdly I wanted that approval.
"Did you do as I asked?"
"Oh you mean shaving my crotch? Yes I did."
"Come here. I want to see if you earned any penalties. Pull your skirt up
to your waist."
I blushed as I had hoped showing myself could be put off as long as
possible but lifted my skirt. He pulled my panties down to my ankles then knelt
in front of me to stare at my pussy to my mortification.
Looking was not good enough he began feeling it with his fingers saying,
"Touch is sometimes better than sight to find stray hairs."
I blushed in shame. He was rubbing and touching and opening my pussy lips even more than I had shaving it. But the worst thing is it began to excite me. He looked up at me and grinned saying," You are not the prude you pretend you are. Your pussy is wet."
I whined. "I can't help it. My mind is appalled at what you are doing but
my body likes it."
"Whatever, I am just glad to see you are not frigid. You may return to
work. Oh by the way have you picked your first instrument?"
"No I thought I would wait until the last minute. The paddle is awful but
I am afraid of where the strap may hit me."
"Yes. It is planned that way the buttocks can take a lot of punishment
while the strap will not cause any inner damage when used on your stomach,
breasts or your cunt although it makes a lot of sting."
"My cunt! My God! I had never thought about being hit there. That would
be awful!"
"Actually the girls that were hit there tell me it is no worse than the
stomach as long as the pussy lips are allowed to protect the clitoris and tender opening to your fuckhole."
That made sense to me since the stomach and cunt had the same skin but
the thought still made me cringe and I decided I would choose only the
paddle or ruler.
I went back to my desk barely able to concentrate on my work. Time dragged
since I spent most of the time watching the clock tick off seconds till
the dreaded five PM. As I watched it I thought that if I was hit once a
second it would all be over in twenty seconds. Even twenty seconds seems like a
long time when you watch them ticked off one by one but I thought I could
take almost anything for twenty seconds and of course I deserved all the
pain he could give me.
I skipped lunch since I had no appetite and just walked out on the street
wondering what people I saw would think if they knew I would soon be naked
and beaten.
All afternoon I thought about all the things I could have done rather than
steal. I could have worked out a payment plan with the mechanic, I could
have borrowed the money from my parents, I may have been able to get an
advance on my salary, or I may have been able to borrow the money from my boss
but I took the easy way out.
By the time five o'clock came I had totally convinced myself I deserved
the punishment and actually was getting a deal because I really deserved
twice as many spanks.
My boss came to me shortly before five and told me to follow him to is
office. I went willingly anxious to get this over with.
At his office he said," Are you sure you want this punishment rather than
what a court may think is appropriate?"
The blinking red eye on the camera let me know he was just providing more
proof this was my idea but I didn't care and made him happy by saying,"
Yes. I deserve being punished severely. I hope it hurts a lot."
He took me to the conference room and I saw the table had been pushed to
the wall and a straight chair was placed in the center of the room in front
of a half circle of other chairs. Girls from our office and his partner
started coming in to seat themselves.
The girls seemed nervous and excited but his partner stared at me with a
look of pure lust. I didn't know if the chair was there to be familiar to my
parents spankings or not but the avid audience made that similarity remote.
He told me to take of all my clothes emphasizing "All" so I started with
my shoes and knee high stockings, then my blouse, skirt and full slip. The
girls were cruel laughing and saying," Check out those Granny panties. I
didn't think anyone under seventy wore those." Another laughed and said, "Yeah
and look at the industrial strength bra. I think it is made out of canvas."
I was hurt and thought about saying, "At least they are not slutty like
the underthings you probably wear." but I thought better of it hoping they
may be sympathetic toward me.
When I took off the bra and panties though I got some satisfaction as one
said," That is a great body. In spite of all my years in the gym I don't
look that good." Another said, "Yeah. Awesome." My bosses partner said," I
had no idea she had that wonderful body. The clothes she wore made me think
she was fat."
I understood that since my big boobs held the blouse out to make room for
a big belly if I had one. The admiration did not make me feel any less
naked since I was standing in front of five near strangers since none of them
were my friends.
I stood there with my hands at my side and my head down in shame blushing
like crazy. The weird thing was no-one commented on my shaved pussy making
me think they were also shaved.
I found out my ordeal would not be over in twenty seconds when my Boss
said, "We all have our favorite instruments. Mine is the paddle. When you
choose the instrument the person familiar with it will give you five spanks and
then a rest for the next set of five."
I groaned realizing I would be naked much longer than I had hoped and also
unlike my parents spanking I would not get a chance to become numb.
Since my crime was against my boss I gulped and said," Please use the
paddle."
He led me over to the chair and I leaned over to grasp the seat. He told
me to open my legs to brace myself.
I heard the "Whirr" then my left butt cheek exploded in pain making me
jerk to make my big boobs jump and sway. He let the pain radiate then hit my
right cheek which hurt just as bad and my jerk and sway was joined by a
little dance as I shifted from leg to leg trying to ease the pain by flexing my
butt muscles. Again he waited for the pain to radiate all though my lower
body before the next on my left cheek then my right and a final terrible
one low down on my butt.
As I leaned there crying he told my audience to check his work. They came
to me and created massive mortification by feeling my cheeks to comment on
the heat and the beautiful red marks. I could hardly believe the cruelty of
one girl who said, "She has tough skin. I think you can hit harder."
He did hit harder for the next five and the ten following until I was
crying hysterically and someone said, "Oh wow. Her ass is going to be just one big bruise tomorrow."
I was sobbing so hard I got hiccups. Instead of feeling sorry for me
someone said, "This is great! All that sobbing makes her tits dance."
Even then it was not over. He had me stand against the wall with my hands
and legs open like a big X to be displayed while I thought about my crime.
I stood there for what seemed like forever while people poked and prodded
my sore buns then he said," I think you should thank me for letting you off
so easy."
I moaned, "Yes. Thank you sir." and I meant it knowing I could have been
hit even harder with the leverage the long handle of the paddle provided.
When everyone had a chance to feel and poke my sore buns I was told I
could dress. When I reached for my panties my boss said, "We all hate your
underwear. From now on you will wear no underwear. No bra, no panties, no slip.
Just a skirt and a top."
I moaned knowing my big boobs would sway when I walked to make it obvious
I was naked underneath. My Mom had only bought me wool skirts since they
would last forever. When I put it on the fibers of the wool stuck my sore
butt lie a million little needles and any movement dragged the needle against
my inflamed skin to make me whimper.
When I put on the blouse I found my nipples were super sensitive and
movement made the blouse rub on them. When I walked I discovered for the first
time that my hips swayed as I moved causing the little needles to sc**** n
my poor cheeks. I found it was more pronounced on stair and our cheap boss
had our parking lot on the top floor of the parking garage to save money. By
the time I got to my car it felt like my butt had been sandpapered to make
it even more sensitive. I also found the stairs made my boobs rub on the
blouse to make my nipples hard to increase the sensation.
When I sat down in my car the needle really dug in to make me gasp and
raise up. there was no-one around so I got out and pulled my skirt up o my
waist to sit on the smooth vinyl seat. It was cool and felt much better and
as I drove it warmed to feel very sensual. Each bump made my boobs move to
keep my nipples hard and so sensitive.
When I got home I took off my clothes and backed up to the mirror. I
gasped as I saw my whole butt was a reddish purple color which explained the
throbbing. I must have rubbed it with cold cream for an hour before it felt
good enough for me to go to sleep. Just before I went to bed I leaned over
with my legs open to see what the audience had seen. I gasped and blushed as
I saw for the first time that position made my pussy even more visible than
a front view.
I finally got to sleep by lying on my tummy with no covers to rub on my
sore ass.

MY MEAN BOSS 3
===============
I woke up the next morning to find my butt was no longer hurting although
there was some throbbing. I got up and went to the mirror to look at it
hoping I was well. The girl was right my butt was covered with bruises making it obvious I would have to choose an instrument that was not confined to my butt also the thought of another spanking by my boss with that terrible paddle was frightening.
I put on another skirt hoping it would not be as scratchy but it wasn't
then I put on a loose sweater so being bra-less was not so obvious. looking
in the mirror proved it was right because there was no bump in the material
from my nipples. However, when I walked to my car I found that the sweater
caused even more sensation to my nipples and try as I might I could not
keep my hips from swaying to stop the scratching on my butt.
I planned to pull up my skirt before I got in my car but there was a man
standing by my car so I didn't have a chance and then I was in traffic so
had no chance to do it on the way. By the time I got to work I was super aware
of my butt and nipples which only increased going down the stairs.
At work it took all my nerve to face the smirks of my co-workers but
thankfully they just nodded at me and continued their conversation.
A little later Mary, the tall blonde, came out and stopped by my desk to
say, "I noticed you are fidgeting in your chair. Are your buns still sore"
"Yes but the main problem is this damn wool skirt rubbing on my buns."
" I'll bet. You really screwed up choosing the paddle. The holes in it
make little blood blisters that take a long time to heal. You would have been
better off with anything else."
"Yes but I owed the spanking to the boss and he said the paddle was his to
use.
Besides I was afraid of the other things because they could be used on my
breasts and I found they were real sensitive."
"Yeah I suppose because of that all the instruments are about the same.
The reason I am talking to you is that we girls think that with a makeover
you could be pretty. The boss agrees and I am getting my portable sewing
machine at noon to fix your clothes while Debbie and Joan do your hair and
makeup. Be at his office at 1PM."
I had seen makeovers on TV and thought that may be nice as long as they
didn't use too much makeup to make me look like a prostitute. I had found a
light colored lipstick was sufficient.
When I went in it was not just the girls. My boss and his partner were
standing there with big grins on their faces. Debbie and Joan were the other
two witnesses so all the people who had enjoyed my punishment were there.
Mary had me stand straight in the center of the room with my hands behind
my back then she unsnapped my skirt and pulled the zipper part way down so
she could slide my skirt down until the waistline was barely above my butt
crack and nearly to my pubic bone. Then as I blushed she ran her hand down
he front of the skirt to feel the bottom of my crotch. Now knowing just
where my slit could be seen she took a piece of chalk and marked a new hem line
about six inches below the bottom of my crotch.
Then she used the chalk to make a Vee from my shoulders to just below my
breasts. Then she drew another line from my shoulders under my armpits and
then back to my shoulders. Finally she made a horizontal line a few inches
below my breasts.
She stepped aside and said to my Boss, "What do you think?"
He grinned and said, "That should be fine."
Mary said, "Okay take them off and I'll sew them up While Debbie and Joan
do you."
I whined to the boss," Would you men please leave?"
He just grinned and said, "No chance. I want to see the transformation."
I knew argument was futile so removed my clothes blushing clear to my
tummy.
Debbie led me to an armchair and started taking down my hair. I had always
worn it in a bun behind my head since it was easy to do and kept my fine
hair from blowing in the wind.
When it was done Debbie said, "God. It hangs clear to your waist. How long
has it been growing?"
"All my life except for trimming on the ends. Why?"
"It hides your whole back. We don't want that do we Boss?"
"No, Cut it shoulder length with a curl on the ends."
I felt bad about that since it had taken my whole life to grow it that
long but then I thought it had taken my whole life to grow my crotch hair and
at least they weren't going to shave my head.
While Debbie cut my hair Joan put on my makeup including curling my
eyelashes and plucking my eyebrows which I had never bothered doing.
She put the pluckers in her mouth and suddenly lifted my legs to put them
on the arm rests of the chair. I blushed in shame knowing that exposed my
vagina clear to my anus to the delighted grins of my Boss and his partner.
Then she ran her fingers over my pussy and pulled any hairs she found.
It hurt more than when I had done it because I had jerked them out while she
pulled them slowly grinning at my whimpers and gasps of pain.
Finally it was over and they told me to look at myself in the mirror on
the wall. I was relieved to see the make-up did not make me look like a whore
but more like a model and I had to admit the hair-style was much more
becoming than my severe bun.
My boss confirmed it by saying," It is amazing what a little make-up and a
hair style will do. She is lovely."
I blushed but enjoyed the compliment.
Mary had finished with my clothes and held the waistband open for me to
step into then slid it up my legs. All it amounted to was two square strips
of material held together with elastic bands like a ladder at the sides of
my hips.
I blushed knowing it would be obvious to anyone that I was not wearing
panties and worse the elastic only came down to the bottom of my butt so the
material could provide flashes of my butt and even my vagina if I took any
big steps.
She put on my sweater and now it fit skin tight and the vee neckline
showed all my cleavage nearly to my nipples and the missing sleeves with the
cutout under my armpits showed the sides of my breasts to prove I was not
wearing a bra. My midriff was bare to the top of the skirt but I consoled my
self by knowing rock singers were just as bare.
I whined," I can't let anyone see me like this!"
My boss frowned and said," You can and you will. This is what you will
wear for the rest of the week unless the girls come up with a better idea."
I went out to my desk and prayed no-one would come in the door which was a
possibility since most of our work was done on the telephone, letters, or
e-mail.
The UPS guy came in about four PM to pick up and deliver. Always before he
had just dropped a package on my desk and impatiently waited for me to
sign for it.
This time he hung around watching intently as I bent over to sign and
talking about the weather. Just before he left he said," You are beautiful.
What happened to the homely girl who had your job."
I blushed and said," She quit."
I liked the compliment and it seemed better to be a new person rather than
have him recognize me.
Five o'clock came and I sat there nervously as employees who weren't
witnesses left blushing as some of them said on their way out that I looked
beautiful.
The boss came out and locked the door then waved for me to follow him.
I followed him meekly to see my audience awaiting eagerly in the familiar
chairs. I stood there nervously until My boss said," Mary. Mark her exposed
areas with a lipstick. We don't want marks that will be visible."
She lifted my skirt slightly then marked all around my legs then lifted my
sweater to mark the top of my tummy and my back.
It frightened me that it would leave a small area to hit me and also that
she had marked my front as well as my back.
I knew I did not want the paddle again or things that could be used on my
front so I chose the ruler.
The Boss told me to pick it up and take it to his partner. I was surprised
that it weighed more than I suspected. Doing that seemed to make it look
as if I wanted it. Then I bent over the chair but he said," No. Stand on the
chair with your hands on your head."
I liked that idea as it allowed me to keep my legs together.
When I was in position he hit across the back of my thighs and slowly
worked up higher. It stung awful but certainly not as bad as the paddle until
the last one at the crease between my butt and thighs that made me yelp.
Then he had me turn around and took the same path on the front of my
thighs. Thankfully my hip bones protected my pussy but the one on my
pubic bone was so awful I shrieked.
Thankfully that was the last one and this time instead of standing against
the wall I had to turn slowly in front of each of them as they felt the
welts.
After all of them had a chance to comment on the heat and size of the
welts I was allowed to dress and go home.
I was so unlucky! there were a couple of men on the sidewalk who stared at
me and I had to insist that another man go in front of me on the stairs
since I knew from behind he would see everything. From then on I brought a
raincoat to work with me so I could wear it to my car and to my apartment.
At home I took off the skirt that had been torturing me all the way home
and looked in the mirror. I was pleased to see the ruler had not marked me
nearly as bad as the paddle and after a long soak in the tub the stinging
was gone.
The experience had exhausted me and I slept like a baby until the alarm
went off.

MY MEAN BOSS 4
===============
The next morning I got up to look in the mirror noting how I was getting
used to being nude. I was glad to see that the marks were not bad with just
bruises where the edges of the ruler had dug in. I decided I would pick the
ruler again since it was better and also his partner was not as mean. I
was relieved since it seemed the punishment was getting less rather than more.
I started to put on the hated sweater and skirt but then I thought there
was no need to suffer until I had to. I decided to put on a raincoat and
wait until I was alone in the parking lot to slip them on.
I no sooner pulled into my space when Debbie pulled in beside me. She came
over and said," I see you are hiding yourself with that raincoat. The Boss
won't like that, you had better take it off now."
I whined," I can't. I am naked under it."
"That is your fault. You had better put on the outfit before someone else
comes by."
I was able to keep from exposing myself by sliding the skirt up under the
coat but I had to take the coat off to put on the sweater. She grinned at
my gasp as the sweater slid over my nipples.
I whined," You won't tell anyone will you?"
"Maybe not. Let's go inside."
She teased me on the way by rubbing my skirt on my butt or the sweater on
my nipples enjoying my little gasps as the needles dragged on my sensitive
skin.
When we got inside she told me to follow her into the bathroom. When the
door closed she said, "You know the Boss would really be pissed off if I
told him you had cheated with the raincoat don't you? The whole idea of the
outfit was to embarrass you and cause irritation."
"Yes. Please don't tell him."
"I might not if you give me some kisses."
I remembered how my parents had been shocked and disgusted when they
showed a gay pride parade on TV and said," I can't do that. I am not a lesbian."
"Me either but I still like a good kiss from anyone. But if you don't want
to I guess I will have to tell him."
I whined," I'll do it." and gave her a peck on her lips.
"Not there silly. Here."
She lifted her skirt to show a shaved vagina like mine. I gagged at the
thought and whined," Please No."
"Okay but God knows what the boss may do when I tell him."
"No! You promise not to tell him?"
"Maybe. It depends on how well you do. Now get on your knees and start kissing my cunt."
I felt totally degraded but got on my knees and kissed her crotch as far
from the slit as I could get noting that at least she did not smell bad."
She said," Not there. On the slit."
I groaned but gave her a little kiss there dying of mortification.
She said," Better. Now do it again."
As she said that she put her hands by her cunt and pulled the pussy lips open to show the wet inner cuntlips. I gagged again but when she said impatiently,"
Do it!"
I kissed her there feeling the moist lips against my lips to make me gag
again.
She said, "Better. Now stick out your tongue and lick it."
I did it although my stomach was churning but even that was not enough,
she made me lick the whole length of her gaping cunt and on her clitoris
until my cheeks were wet with her pussy juices.
Thankfully she said, "Oh wow that is enough. Any more and I will cum and
not be able to work."
She left and I washed my face until it felt raw and rinsed my mouth a
dozen times but I could still taste her. Even though it was not a bad taste it reminded me of how low I had become.
When I went to my desk she came out of the boss's office. I said in alarm,"
You didn't tell him did you?"
"Yeah I did. I thought about it and it was more important to see you
suffer more."
I hung my head feeling this terrible feeling of betrayal. I couldn't
understand how she could be so mean after what I had done for her.
In a few minutes my Boss came out of his office and beckoned me. I went in
fear wondering how many more spanks would be added to my punishment.
He closed the door after me and said," I understand you tried to avoid the
little irritation of your sweater and skirt. Is that true?"
"Yes but it is more than a little irritation. The scratching on my
sensitive skin drives me crazy."
"You will find that your skin may be irritated much more. Sit on the edge
of my desk, open your legs and lift your skirt to your waist."
I did it in fear that he may spank my vagina but he scooped some little
paper clamps out of his drawer. He pulled my slit open and clamped one on the naked pussy lip. I gasped and tears came to my eyes at the terrible pinch. He didn't care he added three more then four on the other pussy lip so my whole cunt hurt terribly. Then he lifted my sweater and put one on each nipple which was even worse.
Tears gushed from my eyes as I begged him to take them off but he said,"
You must learn to follow orders. You may come to my office at your ten o'
clock break and I will remove them. That will give you an hour to remind
yourself that you are never to ignore an order again."
I went back to my desk with my legs slightly open since my thighs would
drag on the clamps. Pain was radiating all through my front and I hoped I
would get numb but I didn't. The pain just changed from a sharp bite to an
agonizing ache. Time goes very slowly when you are in pain and I guess I made it worse by constantly watching the clock.
The Boss started out the door and I asked him how long he would be gone
but he wouldn't tell me just saying," I don't know. I just have to do a
little shopping."
I was hoping to know how long he would be gone so I could take off the
clamps for a while but now I couldn't.
I had to get a file for Mary and just walking that short distance to the
filing cabinets made me make little groans as the clamps dragged against my
sweater and skirt.
Debbie noticed the agonized expression on my face and said," You look like
you are hurting. What did he do to you?"
"He put paper clamps on my pussy lips and nipples. It hurts awfully. You
should be ashamed for telling on me."
Rather than apologies she just yelled, "Mary, Joan. Follow us to the
bathroom you have to see this."
She took my hand and led me to the bathroom with the other girls quickly
catching up with us.
When inside she lifted my skirt as I blushed in embarrassment then said,"
Wow.
They are really digging in. I didn't know the springs were that strong."
"Yes. They hurt awfully."
She lifted my sweater and said," Wow they have totally flattened your
nipples."
Then she hit one with her finger to make it jump.
I yelled, "Oww. Don't touch them. That makes them hurt more! It hurts just
to walk and have the fabric catch on them."
She just grinned and said," I'll bet it does."
They let me go back to my desk but from then until ten they had me running
errands for them especially where I would have to stretch up to high
cabinets or bend over to low ones until every clamp hurt and throbbed.
Finally it was ten and I knocked timidly on the Boss's door for entrance.
When I was in he said," I suppose you are here to have me remove the
clamps."
"Oh yes please Sir. I promise I will never cheat or disobey you again."
"We will see but I think I will have you suffer another ten minutes. Do
you agree you owe me that?"
I had suffered for over an hour so ten more minutes did not seem so bad if
it made him forgive me and after all I deserved it for trying to cheat.
"Yes I owe you that."
"Good. Take off the sweater and skirt and stand against the wall facing me
with your legs open."
I didn't mind that. I was sure I would have to take them off for him to
remove the hated clamps and it was actually a relief to get rid of the
scratchy things.
When I was naked and had opened my legs far enough to please him he picked
up a box and put it on the chair beside me. that is when I saw what he had
shopped for and what he had been doing since he returned.
The box was full of four ounce fish weights with fish hooks tied to them.
He picked one up and I shuddered at the thought he was going to put the
hook in my skin but what he did may have been worse. He put the hook in the
clamp on my nipple then dropped it. I made a little scream as the clamp
seemed to tighten even more making it hurt as much or more than when it was put on. He kept hooking them on every clamp until all he original pain came
back plus more.
I stood as still as possible although I could not stop my breasts from
heaving from my sobs He came up with more torture. He told me to get up on my tip toes and walk around the room. The tears in my eyes blinding me and the pain made me so uncoordinated I stumbled several time creating even more pain as the weights jerked.
When he finally told me to stop and lie on my back on his desk the relief
of the weights no longer pulling was so great I said, "Oh thank you."
ignoring the fact that I would not have needed that relief if he had not put on the weights.
He began to take them off and blood rushing back to my tortured nipples
and pussy lips caused a new pain that again made me sob.
When they were off he began rubbing the deep indentations they had left
and it felt so good it didn't even occur to me that he was rubbing places I
had not allowed boyfriends to do with all my clothes on.
Then he did something incredible. He began kissing and sucking on my
nipples as he rubbed my vagina then rubbed my nipples with his hands as he
kissed and licked my vagina. A feeling of indescribable ecstasy raced through my
body followed by a great feeling of release I later found out was an
orgasm.
He stepped back and said," You are incredibly responsive."
"Oh that was wonderful. I have never had a feeling like that before."
"Well sometime we will have to make new discoveries but right now I have
to get to an appointment and I want to be back in time for your punishment
session."
With everything that had happened I had completely forgotten that I still
faced that. I whined, "Haven't I suffered enough today?"
"What happened today so far has nothing to do with the completion of the
punishment you agreed to suffer. This was just an extra punishment for
cheating.
Incidentally don't blame me for what happens later. I will just be a
witness."
He left and I put on my scratchy clothing and went to my desk. I was
surprised to see it was nearly noon. Time had flown while he was soothing my
hurts.
Mary took me to the bathroom and lifted my skirt to say in amazement," You
have incredible skin. All the indentations are gone with only tiny
bruises."
I knew I was well thanks to the Boss's rubbing, licking and sucking but I
didn't tell her and just agreed I seemed to have good healing powers.
She said," Good. You may need them after this session."
I ignored her knowing I would choose the ruler which had caused little
damage and returned to my desk remembering the incredible feeling of his lips
and tongue on my vagina. It was all I could do to keep my hands away from
my crotch.
I must have daydreamed a lot because I was surprised when Mary came over
to me to say," It is time to go."
All I wanted to do was get it over with so I could go home to masturbate
so as soon as I was in the door I stripped off the skirt and sweater and
went over to pick up the ruler.
The boss said," No. You have had the ruler and paddle. You must choose
another instrument."
I was shocked I had not even considered anything else and went over to the
tale to pick up the cane, then the strap, then the whip. The cane seemed
light and I remembered it had been used on my butt so I picked it up and
said," Whose is this."
Debbie raised her hand with a big smile and I took it to her then bent
over the chair.
She said," No chair. I have something special planned for you. Get on the
conference table on your hands and knees."
I did and she came over to me carrying a sack. She took three scrub
brushes out of the sack and arranged them below my breasts crosswise with the
third lengthwise below my crotch.
She told me to lie down on them and I let myself down as gently as
possible feeling the stiff straw dig into my nipples and breasts and the whole length of my cunt. Just lying on them would have been punishment enough but
that was just the start. She had me open my legs driving the needles deeper
into my pussy then got between my legs. I felt a terribly sharp pain at
the outer edge of my buttcheek from the tip and down my thigh with the
length of the cane. It made me yelp and convulse causing more pain to my
breasts and cunt. She kept on moving from the outer edges of my buttcheeks
toward the center which hurt so much I hardly noticed the needles digging in to
my breasts and crotch. She spaced them closely together but even then she
was hitting between my cheeks towards the end then she said," This is the
last one. You know where it is going."
I knew and sobbed," No!" but the cane came down with the tip hitting my
tailbone and the rest hitting my asshole and into my pussy to cause a blood
curdling scream of agony.
I laid on the brushes sobbing and squirming until she said. "It is over.
You may get up now."
I got back up on my knees to get my breath before getting down and then
went to look in the mirror thinking I must be bleeding since my perspiration
was rolling off me.
My breasts and crotch looked as if I had been attacked by a million
mosquitoes but there was no blood. Debbie showed her first bit of compassion by
saying," I think we should let her wear her raincoat home. She has suffered
enough and the marks will show under her skirt."
My Boss agreed and I thanked them for the relative comfort of the coat
rather than the skirt and sweater.
When I got home I backed up to the mirror to count nineteen nasty red
welts from the top of my butt to half-way down my thighs. Then pulled my
buttchheks open to see the final one which left a welt on my asshole and to the tender inner lips of my vagina.
I went to bed and began rubbing my breasts and pussy until the good
feeling overcame the pain thinking at least I had learned how to combat the pain.

MY MEAN BOSS 5
===============
I woke up lying on my stomach for good reason. When I sat up I winced as I
felt pain in my butt and thighs.
I got up to look in the mirror and counted 19 reddish purple lines running
from the top of my butt down my thighs with the center ones running inside
the crack and down the inner thighs. The whole area felt raw.
I caressed the lines with some hydrocortisone salve but it didn't seem to
help much and I knew the wool skirt would be horrendous but I reminded
myself that I had caused this punishment and would just have to live with it.
The good news was I only had two more days to suffer.
I put on the sweater noting that the scratching on my nipples seemed more
exciting now than painful then put on the skirt. The lines showed below the
short skirt so I put on my raincoat to hide them.
The walk to my car made me wince as the skirt rubbed on my welts but
sitting on the seat made me gasp as needles seemed to dig into my raw thighs.
At the office I took off the raincoat to show everyone that I was wearing
the hated outfit. Debbie, Joan and Mary had me go to the bathroom so they
could study and probe my welts enjoying my little gasps of pain.
Mary said," Wow. The cane really leaves dandy welts."
I said angrily," I would hardly call them dandy. They still hurt even
though they had all night to heal."
Mary said," Well no matter if you choose me or Joan we won't hit you on
the welts. Right Joan?"
"Right. That may make them bleed."
"Really? Thank you for that. I have been living in fear that they would be
hit again."
Debbie grinned and said," You know how to thank them."
I said in alarm, "Oh please don't make me do that. I am not a lesbian and
it is horribly degrading. Besides there is no time."
Mary grinned and said," Did you forget you came in early? We have a half
hour till nine. I guess we could change our mind about hitting the welts.
Right Joan?"
I hung my head in resignation and sobbed. "Oh okay. I'll do it."
I got on my knees and they stood in front of me with open legs and raised
skirts to pull my head into their vaginas one then the other then back for
the whole half hour while I died of shame feeling my face get wetter and
wetter as I drove my tongue deep inside them and wiggled it as ordered.
When the time was up I washed and gargled but could taste them for a long
time.
At ten o'clock Mary said," Come into the boss's office. I made you a new
dress."
I hesitated wondering if this would be made of barbed wire but followed
her in.
While the boss watched she had me take off the sweater and skirt and
helped me put on a dress that was long enough to hide the welts. It had a zipper
up the front and when she zipped it up the dress made of black spandex
that fit so tightly it was like a second skin. Although it covered me
completely to my neck I still seemed naked since it looked like I was just wearing
a coat of black paint. You could clearly see the bumps made by my nipples
and even the indentation of my navel, and the raised portion of my stripes.
It didn't hurt though and did cover me so I thanked them.
My boss said," I thought this costume would be better since any welts
would be hidden from public view."
I moaned remembering either the strap or whip could be used on my belly
and breasts that were exposed by the sweater and skirt but at least any welts
would not be scratched by this material so I thanked him.
Mary grinned and said," She really knows how to thank you. If you tell her
to she will go down on you."
He grinned and said, "Is that right?"
I moaned I had only seen a penis once in a sex education course and had
quickly turned the page in embarrassment but at least that would be
heterosexual activity and Monica Lewinsky had seemed to enjoy it. I hung my head and
said," If you want me to do it I will Sir."
"I think that would be adequate thanks. Come over here and kneel between
my legs."
I knelt there and as ordered unbuckled and unzipped his pants and pulled
them and then his shorts down to his ankles. I was amazed. The quick look
at the picture had not prepared me to see the penis about eight inches long
and a couple of inches thick with big veins in the shaft capped with a
mushroom like head.
I didn't know what to do but he was glad to direct me telling me to lick
it from the head to the base as I watched it grow and get hard in amazement.
Then he had me lift it so I could lick the underside and his hairy
testicles. I was dying of shame knowing only the lowest slut or prostitute would
do this and the girls made it worse by giggling and making comments like,"
She is a born cocksucker."
It became very hard and he had me take it in my mouth then grabbed my hair
to push it deep into my mouth to make me gag then pulling me back only to
pull me forward again to gag again over and over until suddenly it pulsed
in my mouth and I felt his semen shooting down my throat. To my surprise
there was little taste to it although it felt like phlegm.
He held it in my mouth until it softened and then said," Good girl. That
was a nice thank you. You may go back to your desk."
My life was hell for the rest of the day. The girls would put things in
their mouths and grin at me as they sucked them to remind me of my shame and
then they began to whisper to other girls and point at me so I knew they
were telling them I was a slutty cocksucker. I knew the word would spread
until the whole office knew of my terrible behavior. The worst thing was I had
done it with no threats. I assumed I would be punished if I didn't but I
didn't know for sure and should have at least made a token resistance to
find the alternative.
By five o'clock I was so angry at myself I was actually hoping the
punishment would be really terrible.
At five o'clock I went to the conference room without being told then had
to wait while the others came in.
Mary laughed and said," She is really anxious to get punished."
I scowled at her but I had to admit it was true.
When everyone was seated I unzipped the dress and let it fall off my
shoulders to the floor. I blushed as I realized I was pushing out my chest and
sucking in my tummy which I knew from looking in my mirror made me look
good. Again I hated myself for wanting to look good to people who wanted to
see me hurt.
The boss said," Pick your instrument,"
I started toward the table then noticed the chair was missing and in it's
place was a pair of shower clogs about three feet apart and what looked
like small dog collars attached to a rope coming down from a pulley in the
ceiling.
The rope went to a boat cleat on the wall.
This was new and frightening. I said with a quaver in my voice," Where is
the chair?"
My Boss said," For these last two instruments your entire body must be
accessible."
I shuddered realizing I was finally to the point my most sensitive place
may and probably would be hit. I whined, "That will really hurt. Won't it."
Mary said," Yes but you deserve to be hurt. Don't you?"
I whined," I guess so."
She said, "Don't guess! Say you deserve to be hurt!"
I winced at her sharp tone then said," I deserve to be hurt." then I
surprised myself and my audience by adding," I deserve to be hurt so much I will
scream and cry."
Mary grinned and said," We will see to it. You may scream all you want.
Everyone has left the building."
That seemed better to me it had been a great effort to muffle my screams.
I went to the table and picked up the strap and the whip trying to decide.
Although I knew I should be hurt the whip scared me and I chose the strap.
Debbie cried. "Oh Goody. That is mine! Bring it to me."
I took it to her feeling my breasts move with my faster breaths of air
from nervousness. She took it from me and rubbed it on my inner thighs saying,
"I am going to hit you here. Does that frighten you."
"Oh yes that is really sensitive."
she just grinned and rubbed it on my belly across my pubic bone. Saying
"Here too."
I just groaned knowing that would hit the top of my pussy lips.
She rubbed it across my breasts making my nipples pull and said," These
will really bounce."
I whined," Please not hard there! That will hurt awfully."
"Yes but you need to be hurt don't you. You know you deserve it."
"Oh Damn you. Yes."
"Say, Hit my tits until I scream."
I hesitated frightened at that thought until she said," Well?'
"Oh God. Hit my tits until I scream."
She grinned and said, "Put your feet in the clogs and buckle the cuffs on
your wrists."
I thought it was really mean to make me prepare myself for pain noting the
clogs were pointed towards them so they could see every lash to my front.
I had to open my legs to put my feet in the clogs that were nailed to the
floor. I blushed as she said, "Great. That makes her cuntlips open. But
next time I think they should be even further apart."
I clumsily buckled the cuffs nervous and frightened by what would follow
and then crossed my hands over my groin to hide the obscenity of my open
lips.
She said," Good. Tighten the rope."
My boss went to the rope and started pulling it down to lift my arms to
end my brief effort to hide my pussy. He pulled it until my arms were above
my head but he didn't stop there and continued to lift me until I felt my
body stretch.
Debbie said lift her until her heels leave the ground.
Now I felt vertebrae open and pain to my shoulders as my breasts lifted
and my skin tightened over my ribs.
Mary said, "Oh wow. Look at how that stretch has raised her tits so even
the little crease under them has gone and her waist has shrunk to nothing.
I'll bet her skin is super tight. Let's go feel her."
Suddenly hands were all over me squeezing and pinching to make me cringe
and blush at the indecent probing of my most private parts.
Debbie felt my vagina to deepen my blush as she said," God even her pussy
has tightened." My Boss said," Her ass is tight too."
Debbie said, "Ooo I just want to hit her tight parts. Get her wool outfit
and mark her.
They held my skirt against me and marked below the waistband at my pubic
bone and above the hem just below my buttcheeks then held the sweater against
me.
I said hopefully," If I wear this you can't hit my breasts. The marks will
show."
Debbie grinned and said, "No problem. We can just safety pin the cleavage
together."
I whimpered," Please don't do that to me. It fits tight already. Pinned
every fiber will dig into me."
"Duhh. That is the idea." She drew a line at the top of my cleavage then
at the former crease below my breasts.
Mary said," Wow that doesn't leave much room to hit her. About three will
cover her butt and boobs."
"Oh I can double up. I figure five to her butt, five across the front of
her hips and five to her boobs."
The ones to my butt and the front of my hips didn't scare me too much
since I knew my hip bones would protect my vagina but the ones to my tender
breasts really scared me. I decided to try to bargain.
"Please can't I just have two to my breasts and eight to my bottom.
That will hurt a lot."
"No five to each but don't you want to know where the last five will go?"
I had forgotten I was to get twenty and cringed at the thought of where
the last five would go. I whimpered," On my belly?"
"No silly. They would show there. Guess again."
I moaned, "Oh God no. Not on my vagina!"
"If you wish to be formal but I would rather hear you say. 'On my cunt.'
If you said that I may not hit as hard."
I whined," You are going to hit me f