I Screwed the Boss and Rose to the Top
In some ways Ive been very lucky, in other ways no doubt
skill played a large part in my rise to the top ranks of my
profession as a high level administrator. Still, there
is that nagging feeling that my looks and appeal may have
had more to do with it than I would like to admit. After graduate
school I definitely paid my professional dues for several
years before I started to rise within the organization.
Some women deny it altogether while others see it as selling
out or using your sex appeal to get ahead, however, I see
it as just good common sense to always look your best and
dress the part. Ive simply made it part of my life and habit
to always try to look like a knockout, dressing immaculately,
staying in tip top condition and always having my hair styled
and wearing the right jewelry and accessories. My makeup
and color have come only from the top salons and colorists.
Some women might say my lipstick and eye shadow are a bit
too dark for the corporate world and others would say my
very long perfectly manicured nails are too sexy for the
office. I say, however, that all these things have a place
in commanding the attention needed to get ahead in a mans
world. Men, all men, simply love it.
Ive always been a little too flirtatious and Ill admit
that at times it tends to demean me in the eyes of others but,
again, men love it. Even my husband gets off watching me
drive the establishment guys crazy at parties and even
in public. Fortunately for him, he isnt aware of a number
of things Ive done along the way to help myself become more
successful. Weve been married since before graduate
school so the list of my misdeeds is longer than Id care
to admit, but in rationalizing my behavior, I have to think
that it ultimately benefitted us both financially and
socially. There can be no doubt that Im devoted to my husband
and love him with all my heart, however, I have needs and
urges that go beyond what he needs to know and for all I know,
he may also have his secrets, probably does in fact.
I remember well that in my mid twenties, I was particularly
ambitious and willing to do things I never would have imagined
just to get ahead in the corporate world, yet in my heart,
I never felt I would compromise my marriage. During a two
or three year period early on I worked for a division headed
by a loud and blustery, obnoxious character named Stan.
He was relatively intelligent and he thought he was hilarious
and apparently somehow sexy. I cant count the times Ive
faked laughs at his crude humor and sexual innuendo while
all the time thinking Id like to scream and run out of the
office or at least slap his face. To my shame, however, I
never did that and what I did do makes me cringe but sometimes
still makes me quiver down under late at night.
Stan was a little unusual, at least in my experience, as
he was very Jewish but stood at least 6'6" and
probably weighed a good 275 lbs. I hate to stereotype but
most Jewish guys are small in stature and I assume elsewhere.
On the other hand, Black guys are all supposed to be well
hung and Ive found that definitely not to be true. At around
50 years old Stan was not in good shape, a large belly hung
over his waistline and he was balding quickly. What was
left of his salt and pepper hair matched his beard perfectly
and he had a booming, braggadocios voice and style that
put most everyone off, including me. I was easily young
enough to be his daughter and the thought of ever actually
doing anything with him sexually had never remotely occurred
to me, although I did go along with his sexual banter and
innuendo. I never talked back to him in such a manner but
I did condone it and maybe encourage it a little.
Stan would ask me to stay late at the office at least 2 or 3
times a month and very rarely was there any evidence that
it was necessary. Wed sit in his office of a conference
room and unnecessarily crunch numbers or go over spread
sheets, sometimes just talk work related chatter but never
really accomplishing much at all. It was obvious that he
just wanted to be around me and flirt, and inevitably we
would end up going out for dinner or ordering in. He was inappropriately
forthright at times about wanting to have a more intimate
relationship with me and the late nights would almost always
end up with me laughing and rejecting his verbal advances.
He always backed off quickly and it was never really all
that uncomfortable I suppose.
One particular night before Christmas we were working
late in his office, which was an overly large corner office
in downtown Baltimore. We were sitting at a conference
table finishing up a Chinese take out dinner when he pulled
out a bottle of very expensive Scotch from under his desk
and said Hey, look what someone gave me just this morning.
My people dont celebrate Christmas so I cant take it home.
Whadda ya say, lets have a little Christmas cheer, well
be here another two hours at least. Itll help the time pass.
Id been in public with Stan many times when hed been drinking
and he definitely becomes more obnoxious and aggressive,
but for some reason I said OK, but Ive got to drive home
later, so just one. The fact of the matter is, like most
women, Im a terrible drinker. It goes straight to my head
and, in my own way, I act as stupid as most guys when I drink.
Stan poured a couple and we made a little toast of the occasion
and pretended we would get back to work. At this point he
was behind his large mahogany desk and I was across from
him re-applying my lipstick as he looked at me intensely
and said, You know why they call me the Big Boss around
here dont you? I looked at him and laughed and said Stan,
Im sure its got nothing to do with your weight, right?
He gave a big resounding laugh and said, I may be a little
older and out of shape in some ways but Im built like a racehorse
where it counts. I guarantee you, youve never seen anything
like it and you wouldnt be able to resist if you did.
God, I hate that kind of talk, especially coming from an
older man, one whos my boss and one who I can hardly stand
to look at. However, I was somewhat intrigued that this
old out of shape guy would even have the gall to say such a
thing to me, a young and very hot looking young executive.
Jesus, I could have him fired in two minutes if I filed a sexual
harassment complaint against him. Besides, hes married
and has two grown kids in college. I decided to play along
for a few minutes. Stan, thats a lot of big talk, coming
from a guy like you, but I havent seen a thing that backs
it up. I had definitely had too many Scotchs. I couldnt
believe I even said that. My face flushed with heat and embarrassment
as he smiled from across the table. Oh, youre ready for
the proof now are you? Come around here and Ill show you
something like youve never seen before, I guarantee
he bragged. Damn! He sure knew what to say to intrigue a girl.
At this point I honestly was curious and a little turned
on, not to mention quite tipsy. Well you reel it out there
Stan, and Ill come around and have a little looksie, OK?
I still couldnt believe I was flirting with him and apparently
about to take it to a more uncomfortable level. I felt like
the cheapest little schoolgirl but I couldnt resist the
temptation just to look and humor him. I still wasnt sure
if we were just talking or if he was serious, I was just too
stupid drunk to tell so I just sat there laughing nervously.
He did appear to be undoing his zipper and smiled from ear
to ear as he repeated Come on, Im ready, all you have to
do is look.
I stood up and grabbed the desk I was so tipsy. I held onto
the edge of the table as I guided myself around to his side.
He tilted his large leather chair back and put his hands
around to the back of his head and smiled as I made my way toward
him. His pants were completely undone and spread apart
as he spun his chair around toward me. I looked down between
his legs and gulped as my eyes focused on his cock, his very,
very nice looking cock. He was a good 10 inches long and very
thick and straight. I could hardly believe my eyes that
this less than handsome older man who Ive known for three
years could possess such a magnificent piece of equipment.
I admit I had a hot flash come across my face and between my
legs as I admired the scene.
The longer I stood there and looked, the harder he got as
I said a little breathlessly, Well, Stan, you werent
lying this time. Who would have thought you were such a monster,
in a good way. We both laughed as he took his cock in his hand
and started to stroke it and we watched it grow even more.
Why dont you come down here and get a better look, Sandy.
Anyway, I know youre going to want me to fuck you in a minute.
I think you know it too. I really could hardly breathe at
this point I was so turned on. I walked a step closer and went
down to my knees in front of him with both hands on the arms
of his chair to steady myself.
I stared at his cock which was now throbbing without either
of us touching it. I could literally feel the heat from his
crotch as I moved my face closer. He started to breathe more
heavily as my face moved a few inches closer and he leaned
toward me to get a better look at what I was about to do. His
dick stood straight up as my hands moved from the arms of
the chair and I positioned them around him. It was so thick
I could barely get each hand around it. I put both hands around
him at the same time and started to stroke it around the rim.
He grew even more as I moved my lips right up to the head of
his cock and I stuck my tongue out for the first taste. Mmmmmm,
as my tongue lapped the head of his dick he moaned loudly
and pushed his head back. My God, thats good. I always
knew this would happen, I just didnt know when.
I actually had a slight feeling of discomfort in hearing
his voice reminding me who he was, as strange as that seems.
Id worked with him for years and never had a sexy thought
of him in any way whatsoever. Now here I was about to suck
his cock and who knows what else. God those long sexy nails
were your giveaway from the start. Dave and I used to talk
about what we thought that was about and it had to be about
pure sex appeal. I knew you had something burning inside
when I first laid eyes on you. Now you just enjoy your dessert
and Ill sit here and watch. It almost sounded like a command,
but I actually didnt mind being commanded right then.
Afterall, he was the Big Boss. My long red nails embraced
his dick and I lightly scratched him from top to bottom as
he flailed in my hands. His hips moved upward toward my face
to try to force his way into my mouth. I stroked him long and
hard as finally I plunged my mouth around the head of his
dick and began sucking ravenously. Not only did it look
wonderful, he had a sweet taste that drove me crazy. I know
I must have looked like a nymphomaniac as I sucked and slurped
his cock into my mouth and ran my tongue all around him. He
moaned very loudly and I worried that if anyone else were
in the office building, theyd be able to hear him. Apparently
he wasnt worried about that as he practically screamed.
I was so turned on I know my pussy was dripping. I reached
down with one hand and started to finger myself as I continued
to suck on Stans hard cock. He kept pushing toward my face
with his hips and finally I looked up and said, OK, you win.
Fuck me. God, fuck me. I reached down and pulled off my panty
hose and underwear as I turned my back to him and started
to sit on his lap. At first I wasnt sure hed be able to fit
into me as my pussy lips met the head of his dick but after
squirming for a few seconds, I could feel his huge dick making
its way into my very tight cunt. Aaaahhhh, my pussy was
being filled on all sides as I pushed down and pulled back
up. I raised up just high enough for his dick to come out of
me and then squished back down again to let him go in even
deeper. I closed my eyes and hoped that he wouldnt say anything
at all since Id rather not concentrate on the fact that
I was screwing Stan. He moaned and reached around to grab
my nipples as my full weight came down on his cock. I was doing
most of the work since my hands were on the arms of the chair
lifting and lowering my weight to his absolute pleasure.
I could feel him growing even larger inside me as he squeezed
my breasts hard and I pumped up and down. See what youve
been missing all these years he said, as my spirits were
somewhat lowered by hearing his voice. As I started to say
something pithy and clever, I noticed my voice was gone
and I couldnt utter a word as I kept pounding upon his hardness.
I just muttered something like yes, yes and continued
enjoying my ride as I panted. After a good ten minutes of
incredible fucking, I lifted myself off his lap. My legs
were literally trembling and I briefly held onto the edge
of his desk for support.
Im going to fuck your ass now and youre going to love it
Sandy so dont even think about saying no, he said as he
stood up from the armchair. He clenched his dick in his big
hand and waved it toward me. I really didnt like the idea
of this but I just gulped and caught my breath as I said fuck
me anyway you want. Yes, fuck me in the ass but be careful.
I grasped the edge of the desk as he moved in behind me. Do
it with your fingers first or youll rip me apart, I managed
to say. Ill rip you apart one way or the other anyway and
youll love it, so just relax. He reached into his top drawer
and pulled out a bottle of lube and doused me down quite liberally.
He did finger my silky ass first and it felt very nice. He
said breathlessly, Ive been saving this for a long time
and I knew Id get to use it one of these nights with you as
he poured on more into my ass. I reached back and grabbed
his dick with one hand and led it between my cheeks and up
to my ass. He immediately started pushing too hard and I
had to hold him back slightly. As his dick penetrated my
ass, it hurt for a few seconds and he backed out and fingered
me some more. He came back at me with his dick and pushed it
about halfway in. I literally gasped and fell forward on
the desk waiting for the pain to subside, which it soon did.
He moved his cock back and forth very slowly for a while and
suddenly I said Ok, stick it all the way in me. God, now.
Its funny how I was able to simply look at this strictly
from a sexual point of view and enjoy it, because nothing
could ever have been further from my mind than fucking my
boss, especially a big out of shape creep like Stan. I wasnt
just having some casual experience, I was letting him fuck
me where my husband has rarely gone. Stan fucked my ass very
strongly once he was sure I could take it and again my legs
started to tremble. I could feel his dick moving up through
me and putting pressure on parts of me I didnt know existed.
It felt like his dick was going up into my stomach with each
lunge up my ass. God it was good. I bent my head down as far
as I could and pulled up my skirt so I could see him penetrate
me from below. I could see his gigantic balls banging against
my butt as his dick slid in and out of me bringing me from one
orgasm to another. Finally, I just laid face down on the
desk and let him do whatever he wanted. It took him another
few minutes before he said, Sandy, Im about to cum. I want
to cum in your mouth. In my mind I was thinking Hell no,
that would be like eating my own ass but what I actually
said was Yes, yes, fuck my mouth, fuck my face, I want your
cum in my mouth. I heard my words and could hardly believe
it was my voice.
I spun around and fell to my knees again as I looked at his
swollen dick shining in the semi-darkness of the office.
This was the first time Id actually looked at him since
we started fucking but instead of being repulsed by him,
I really wanted to satisfy him more than anything else.
I said, let me do that as I took his dick from his own hand
and rammed it into my mouth. At first I sucked very hard but
it was evident that he wasnt quite ready to come so I slowed
down and worked my tongue all around his dick. I licked his
balls and sucked them until he screamed as I stroked his
dick from top to bottom with my fingers. I could feel him
growing even larger and I could feel the inner squirt as
cum started to fill his cock, ready to emerge. I grew even
more excited as I grabbed him with both hands and squeezed
hard, placing my lips over the head of his dick.
I tasted a slight bit of cum in my mouth which actually brought
me to a mini-orgasm. I stroked harder and he said Im cumming,
damn, here I cum, he seemed to me like he might have a heart
attack as he yelled Oh, God, God and rammed his dick into
the back of my mouth. He filled my mouth with warm cum and
I almost gagged. The taste was wonderful but there was so
much I didnt want it dripping on my dress. I moved back slightly
and let cum run down my mouth and fall to the carpet. I sort
of sputtered cum from my mouth as I looked up at him and said
Is that all youve got?. He laughed loudly and grabbed
his dick, squeezed it very hard and slapped my face with
it. He popped it up and down against my mouth and cheeks and
slapped me with some force across my nose and forehead.
I was not offended. I absolutely was in heaven. More,
I said as he pounded his big wet dick on my face. I pulled his
hands from his cock and replaced them with mine. I slapped
his dick against my face with my tongue sticking out to lick
every chance I got. Ill bet youve dreamed about these
long red nails on this monster dick a thousand times havent
you? I teased. You might be kidding, he said struggling,
but I actually have. God I love that sight, this is too good
to be true.
No sooner did he finish talking than I felt his jism filling
his cock again and immediately start to erupt. Again, he
laughed as he slapped his dick hard against my face and I
stuck my tongue out to lick him as often as I could. I grabbed
his cock ferociously and slammed it against my lips and
started to bite the monsters head fairly hard. Aaaahhhh,
he yelled as I started to laugh uncontrollably and continued
to bite and gnaw at him. I couldnt tell if it really hurt
him much or if he was enjoying it. All I know is that he started
the rough stuff by slapping my face with his cock and now
I was returning the pain by biting him. I soon had my answer
as I looked up and smiled, opened my mouth for another bite
and felt him jerk several times as a huge load of cum ran out
of his dick and into my mouth. It was not a hard spurt but rather
a long creamy stream of white cum dropping on my lips, chin
and into my mouth. I wouldnt have thought he had that much
left but the stream seemed never-ending and I didnt want
it to end either. God, Im a fool for a guys cum. I lapped
up every drop I could force into my mouth and deepthroated
his cock pretty much all the way although I did gag a couple
of times.
In the end, I just collapsed on the floor at his feet as he
sat back into his overstuffed leather chair, and I think
he actually fell asleep. The room was swirling around,
I was so drunk, and my body was shuddering from countless
orgasms as I lay there sweating. I knew it would be awkward
coming into work tomorrow morning and facing him, but I
also knew my career had just received a potential boost.
For the next two years my star was definitely on the rise.
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