Teasing the Boss

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 15 many years ago this week.