Naughty Office Shenanigans

A young intern at a law office gets friendly with her older, distinguished boss.


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The summer I was 18, after I finished high school before I went to college, I got a summer job as an assistant at a law firm. I was going to become a lawyer myself and considered myself lucky to have gotten this job, even though my father may have had a hand in it. His lawyer was the one that owned the prestigious firm. There were many partners there and it was the busiest firm in town, lots of people in and out all day at that place.

I was to help in the office of Bradley Andrews. He was a nice man it seemed, around 42 years old, a family man and an estate lawyer. Not a very exciting branch, mostly paperwork, not any exciting murder trials or anything like that, but there needs to be ones for doing the more mundane tasks as well, and he seemed a stable sort and that kind of law suited him. I put in long hours at the firm wanting to know and learn as much as I could to better help me for my future career in law. I hadn’t yet decided what type of law I wanted to practice, but all this paperwork kind that he did didn’t seem very exciting to me.

As it was summer, some of the regular girls were on holidays and we were often short staffed, so the girls that were there often had to put in extra hours to make up for the missing ones. One night Mr. Andrews asked if I could stay late and help with the usual mountain of paperwork that had piled up during the day and I said I could, so we ordered some takeout and had dinner at his desk before starting in for the hours of work ahead.

“Thanks so much, Emily,” Mr. Andrews said.

“No problem,” I replied.

“You seem to be a hard working young lady, I am sure you’ll go far if you do go into law, it’s a profession with many workaholics in it,” he confided.

We waded our way through the work and as we worked away he told me things about his personal life, things he maybe shouldn’t have mentioned, but he seemed lonely. He admitted his marriage wasn’t going that well, they were drifting apart, his wife was a Dr. and too tied to her own career, their children were teens and nearly out on their own. He just seemed lost and alone and filled his hours with work and even said his marriage was over in every real sense years ago.

“But you’re still a young man, you’re talking about yourself as if your life is over and set in stone,” I said.

“Well, I don’t have anyone I feel close to anymore, I feel alone in so many ways. I wish I felt alive again. I’m filing for divorce in the new year I believe, things can’t go on like this,” he admitted.

I felt bad for him, he was a handsome man, around six foot two, black hair, blue eyes, didn’t look his age. After him telling me these personal details, I started to think of him in a different light. As we finished the paperwork and I said goodnight and went home, my mind was filled with little else other than my late night with him and how a good looking man like that didn’t have anyone. Even though married, they lived as roommates and little else. I didn’t have a boyfriend at the moment either and shouldn’t have been thinking what I was thinking about him…

The next day I went to work wearing a nice sundress, perhaps a bit too low cut for the office, but it was summertime and seeing a bit of skin wasn’t out of the realm of possibility. When I took Mr. Andrews in his morning coffee I could feel his eyes looking at my cleavage as I set the mug down on his desk. He didn’t say anything, but he noticed, not a doubt. I was filing some contracts in the filing cabinet and bent over without bending my knees, and I think he could see the tops of my stockings as I did so.

At lunch he asked me into his office and told me I was looking very nice today. I noticed a slight bulge in his pants and smirked to myself knowing I was the cause of it. He wasn’t going to be the aggressor here, I was certain of it. He would be too afraid of appearing out of line, so I’d be the one to make the first move, I knew I’d have to.

“Do you need me to stay late again any night this week, Sir? I don’t mind at all if you’d need me,” I said coyly.

“Well, if you don’t mind, I really did fall behind today after going out with that client this morning for a while,” he admitted.

“I’m glad to do it, Mr Andrews,” I offered.

After everyone went home, we were the last two left and we again ordered takeout, ate at his desk and then settled in for the nights work.

“Mmmmm, let me see,” I teased.

“You have a bit of sauce at the corner of your mouth from the pizza,” I stated.

He tried to wipe it off, but was aiming for the wrong side. This was my perfect opportunity.

“No, you didn’t get it, here,” I said as I leaned in and kissed it off the corner of his mouth and licked it with the tip of my tongue.

When I pulled back, Mr. Andrews looked shocked. Then he reached forward and took my face in his hands and pulled me close to his face and softly kissed me on the lips. It was a gentle, sweet, almost shy kiss, like he seemed hesitant to move forward, even though I’d all but given him a gold engraved invitation with my actions. Again, I felt I would have to be the one to push, so push I did. I pushed him back in his chair and straddled him, my legs dangling over the arm rests as my ass fell squarely over his lap and I could feel his growing bulge get harder by the second.

“I think you’ve been without far too long as it is, Mr. Andrews,” I stated.

I started to loosen his tie and unbutton his shirt and run my hands underneath his shirt to feel his well muscled chest under my fingers. He grabbed my ass cheeks in his hands and squeezed them and kneaded them as his tongue slipped past my lips and into my eager mouth. It’s about time, I thought to myself. He seemed to loosen up and lose himself more deeply in this kiss and I could tell his passions were rising, along with his cock. We kissed for a long time, him unbuttoning my blouse and cupping my breast in his hand as he kissed me passionately. I got off of his lap and walked over to the door to lock it and returned to his chair and sat on his desk, parting my legs so he could see the sheer panties I had on underneath that revealed my slit through the flimsy fabric. He slid a hand up my inner thigh and started to lightly stroke my pussy through the panties. It felt wonderful to feel his hands on me, teasing me.

I reached over and undid his belt and unzipped his pants and reached in and grabbed his cock which sprang free of his boxers. I grabbed it firmly and started to stroke it up and down, caressing it and marveling at it’s size. He was quite well endowed, I’d bet over eight inches and he smiled at me as I took in the great size of it. He had a prideful look on his handsome face as he saw me take it in with my eyes. He continued to tease my pussy lips through the fabric and as he saw me biting my lip in frustration and bucking against his hand, he finally slid some fingers inside and felt my sticky wetness on his fingers as he made little circles over my stiffened clit. I continued to masturbate him and smooth his copious amounts of precum all over his shaft making it slick and shiny from his own juices.

A few more circles from his fingertips and I came all over his hand and seconds later he had my fingers covered in his hot cum that was all over my hand to the wrist, which I then licked off as I looked him in the eyes.

“My wife would never do that in a million years,” he said as he watched me lick it all off my fingers.

“Well lucky for you I’m not her. And she doesn’t know what she’s missing…,” I purred.

He sat back down in his chair, pants around his knees and I straddled him once more and felt that huge cock slid into my pussy, stretching me open. It was so big it hurt a bit at first until I slid up and down on it a few times and got used to its girth inside of me. Fuck it was big. Long and thick. I’d been with a couple of guys before, but they had nothing on this monster cock. He had his hands at the small of my back, his fingers laced together so I could lean back and ride him. I was grinding against him as he sucked on my nipples. I could feel another orgasm welling up inside of me and I kept bucking and bucking against him until I came all over his cock. Seconds later I felt him gush inside of my pussy and cum with rope after rope of cum. I collapsed in his arms and he just held me as we sat in that chair just trying to catch our breath. After a few moments I climbed off and started to straighten my clothes. He had a bathroom attached to his office so I went in there to get cleaned up a bit before going home.

As I came out of the bathroom, he said, “I think you can call me Brad from now on, ‘Mr. Andrews’ seems a bit formal now after all we’ve shared.”

“Alright Brad, I shall see you in the morning,” I grinned as I left the office and walked out to my car. Yes, I think this would be an interesting summer after all, I thought to myself.



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