TEASING THE BOSS (M/F) - Boss Takes Control of Teasing Paralegal

When I was 20-years old, I started working as a paralegal in a
small but well-known local law firm. The attorney I worked for,
Doug, specialized in matrimonial law.

I was immediately attracted to Doug. For starters, he was
gorgeous. He was 38-year old, and his 6’0”, 170 lbs., very fit
body towered over my petite 5’4”, 110 lbs. frame. His dark brown
hair and beard flecked with gray beautifully accented his deep,
dark eyes and warm smile, contrasting my blonde hair and green
eyes. He was also an impeccable dresser who loved fine clothes.

Doug also had a warm and funny personality, and always treated me
professionally and respectfully, never trying to take advantage
of me because of his position or my age. He often took his
secretary and I to lunch and was ever the consummate gentleman
with us both.

After several months in the office, I began to learn more about
Doug. I learned that he was separated from his wife and was in
the process of divorcing her. I also learned he did not date very
much, choosing to focus on his practice instead of “jumping back
into the pan” as he put it. He was also funny, sweet and a
brilliant man. And despite his occasional and secretive glance at
my legs, he was never inappropriate. Indeed, I found his company
to be so far superior to that of men my own age, who were only
concerned with sports and getting into my panties.

Over time, my attraction to Doug turned to lust and infatuation.
I wanted him so badly, even if it was just for one night. As a
certified tease since high school, I knew how to get a man’s
attention. I knew Doug was a legman so my skirts became a little
higher, as did my heels. And I always made sure to wear stocking
instead of pantyhose for those moments when he might catch a
glimpse of my stocking tops and garter straps.

This went on for several weeks, with his attention to my legs
becoming more noticeable. Plus, as our relationship warmed, so
did he. He began to tell me more about himself and our
conversations became ever more flirtatious.

This all reached critical mass as he was preparing for a large
trial. As his paralegal, we were putting in long hours preparing
documents, indexing transcripts, and other trial prep work. One
night, we were working very late in his office surrounded by
Chinese food and stacks of papers. He asked for me some document
and, in keeping with my ongoing teasing of this fine man, walked
over to desk, bent at the waist with my ass facing him, and began
sorting through some papers while trying to give the best view I
could while bent over in my 4-inch heels. I heard him move behind
me but did look to see what he was doing, so I was startled when
I felt his hand caress my ass, then gently slide down to my
stocking covered leg and then back up my ass under my skirt,
taking his time enjoying the contrast between my stocking top and
my bare thigh.

“Alissa,” I heard him say, “I have enjoyed your little teasing
games for quite some time. But now I’m very tired and very horny
and I’m going to fuck your little pussy, understand?”

I almost had an orgasm when he said that. I could only respond
with a moan and by resting my arms on his desk to ready myself
for his cock.

I felt his fingers move my panties aside while his other hand
caressed my now drenched pussy, massaging my clit with just the
right speed and pressure. Then I felt the head of his cock push
its way into me, easily sliding inside of my wet pussy. As soon
as he was inside me I had a powerful orgasm.

Then I felt him take my hips in hand as he began to fuck me,
telling me how good my “hot little pussy” felt, how a “cocktease”
like me needs a “good fuck now and then” and how lucky he was to
have a “sexy little slut” like me for a paralegal. No man had
ever talked to me like that before and it made me so fucking hot.


The more he fucked me and talked dirty to me, the more turned on
I got. So I began fingering my clit too. “That’s it you sexy
little slut, play with your pussy for me. Cum all over my cock
again.” And I did, just seconds before he filled me up with what
felt like gallons of his own cum.

Eventually we got our senses back, kissed and cuddled a bit, and
finished our work. Then he took me back to his home for the
night, and the night afterwards, and so on. But our office sex
was always our favorite. I personally loved giving him blowjobs
when he was on conference calls with judges.

But the first time was the best because it was with me bent over
my boss’ desk in stockings, heels with his cock buried in my
pussy that I fell in love with my future husband.