The bittersweet tale of the time I fucked my boss

7 min read

photo: SexArt

I got into my car and started to drive away.

Anxiously I thought to myself, “Oh fuck. I just fucked my boss. I have to leave the business, I won’t be able to find work for awhile, I don’t have any savings. Oh fuck, I just fucked my boss.”

Then, the devious pervert inside my head inserted a comment, “You just fucked your boss in a delicious, sweat filled, spit filled, lustful, two hour rock’em sock’em session… and you loved it.”

The corners of my mouth spread out involuntarily and my lips opened up into a full grin. I felt the same tingle inside of me that I felt two hours before and then my dick got rock hard as I began to think about the affair.

I worked at a restaurant as a “jack of all trades.” I was the waiter most days, I was the maitre’d on others, the stock person in the mornings and then the secretary, answering phones and setting appointments. I liked doing these things and I was good at all of them. My boss was a beautiful, independent woman who was voluptuous and had a stunning smile. The only thing that kept me from being a complete pervert around her and undressing her with my eyes every time she spoke to me was that she was such a good business woman. I wanted to open my own restaurant one day and I figured I could learn from her, so I put my perverted thoughts away.

One Saturday, I worked the late shift and we were hectic. We had an enormous number of people at the restaurant and were short staffed. I was on point in my productivity and even she had to pitch in and take orders while the chefs turned out food like machines. We ended the day and we did great but were super exhausted. We closed the door to the restaurant and as the chefs cleaned up the kitchen, I cleaned the main floor as she was in the back counting the day’s take. Slowly, people started to finish up and go home. I eventually finished my work and started to pick up my things. My shirt was sweaty so I went to the employee’s back room to change it before going home.

I took off my shirt and had my keg gut hanging out when my boss walked into the back room. She startled me and my head shot up, jerking my dry shirt onto my chest as if I was a prude virgin.

“Really?!” she said, walking into the room. She laughed and then so did I, embarrassed at my reaction. “Can you help me with one thing before you go?” she asked me. I nodded and put on my shirt. I followed her to the back office. She said, “I just need you to help me put these papers back and put the boxes on the top shelf. Pleeeease, I’m so tired.”

She was wearing a black blouse and at this time of night she had unbuttoned the top couple of buttons. Her D cup cleavage was visible and her dark brown hair was loosened so it fell just so onto her shoulders. She looked terrific. I, of course, agreed and I helped her stack the papers.

My perverted mind began to peek out and direct my eyes to look at her sexually. I was starting to undress her with my eyes — I thought about the bra she was wearing underneath her blouse. It probably matched with her panties, she was so sophisticated. Her belly was flat and tan and her stomach curved down into her pelvis and inner thighs. Her pussy was probably smooth… She jerked my wrist, “Hey, hey, are you falling asleep on me?!”

She smiled at me and I could see her lipstick had worn off her lips. She had full lips and a megawatt smile so I wanted to grab the back of her head and pull her into me.

“Yea, I’m fine, sorry, haha,” I said. I began to lift the boxes and put them on the top shelf.

“Oh my god, thank you so much for staying,” she said and then she hugged me. I felt her tits press against me and I grabbed her waist and pulled in for the hug.

She pulled back and smiled at me again. My dick was starting to get hard. She stepped back and grabbed the back of her neck.

“Oh fuck, my neck,” she said. “I sooo need a massage,” and she continued to rub and knead her trapezius. I turned her around and I put my hands on her traps.

“Let me help you,” I said, and I began to rub my fingers on her and give her a massage. She didn’t say a word and didn’t pull away. I began to lightly knead her muscles and I could feel my dick get rock hard. Her ass was a foot in front of me so she couldn’t feel it, I was ok. I couldn’t resist and I dug in deeper to her muscles. She exhaled and her body backed up into mine. My dick was right in between her tight ass cheeks. She raised her arm and started to touch my hands. She slipped her fingers under mine. I stepped all the way forward and wrapped my arms around her.

I started grinding my erection against her ass cheeks and I felt her hips rock, then begin to grind over me. I unwrapped my arms slowly and our fingers interlocked as we were feeling every sensation, not saying a word. One of her hands slipped out from mine and went backwards to touch me. She cupped my erection and she completely gave her body to me, leaning her head back on my shoulder. I pressed my hand onto hers which was cupping me. I started to kiss her neck. We kept grinding on one another in this position, our hands rubbing everywhere. I put my hand between her legs, on her pussy. I rubbed it up and down and we were clutching, breathing heavy and enthralled.

She turned around and we kissed; she clutched my face and we stuck our tongues over one another desperately. Our hands were pulling at our clothes. I started to bite on her neck and she yelped. She returned the favor and kissed my neck with hungry kisses. She licked my neck and then we went back to kissing each other even more passionately than before, licking our lips and thrashing our tongues together.

She kneeled and started to unbuckle my belt. She did it desperately and rushed. She unzipped my pants and pulled out my cock. It was sweaty from the day and she swallowed it. She deep throated it and started to suck on it very hard and fast. After a bit, she took it out of her mouth and started to slap it on her tongue, teasing me. She swallowed me again.

I lifted her up to her feet, crazy with desire, and moved her to her office chair. I pushed her down into it and knelt down.

“Take off your pants!” I demanded.

She started to unzip them and said, “Take them off! Take them the fuck off!” I yanked her legs up to my shoulders and pushed my hands under her waist, tugging at her pants. As they reached her calves, I dipped my head underneath them and rammed my face into her pussy. My tongue hit first but I had to take a full sensual bite so I opened my mouth and put all of myself onto her pussy lips. As my lips touched I sucked her lips in my mouth and made her scream. I began to flick my tongue on her clit and then I took her clit in my mouth. I sucked on it as hard as I could and she was screaming. I didn’t want to stop. I was blind with lust.

She pushed me off of her and said, “Lie down on the floor!” I lay back and looked up at her. She took off her pants and her panties. She straddled me and grabbed me. She brushed my cock head onto her lips and slipped down on me. She pushed on my chest and started to fuck me. Her pelvis rocked on me over and over and over. I pushed up into her and she started to sit on me. After a few minutes, as she started to slow down, I sat up and I looked her in the eyes. She caressed my face and I hugged her body. I kissed her cleavage and kept hugging her as I took over and started to pound her into me. We stayed hugging and kept fucking.

As the time passed, we started to get tired but were still high off of our lust. We got up wobbly and I nudged her over to her desk. I bent her over and she smiled. She did so willingly and propped one of her legs on the desk.

I slipped into her warm pocket of silk and I wrapped my hands around her waist. I thrust into her and made my final pushes. I slammed into her and my hips made a slapping sound against her ass. I pulled her up to me and we fucked standing up. I started to play with her clit, moving my fingers in circles as I rammed up as far as I could inside of her. We clutched and fucked and all of a sudden, she came hard, grabbing me as tight as she could. As her pussy tightened, I felt the urge and pulled out of her, exploding all over the floor and my hand.

We were emotionally drained. Several minutes passed as we collapsed in separate areas, breathing heavy, wiped out.

Two hours had passed into the night since the last person left the restaurant. No one was walking the boulevard in front of the store and only the night security guard was in the immediate area. As we recovered, we began to straighten ourselves up. She went to the bathroom as I put my clothes on.

I sat in the office chair and she walked in — face washed, hair straightened, blouse and pants on and wrinkled but looking clean (and so fucking hot).

“I think we’d better go,” she said. I nodded and got up to walk out. We walked out without saying a word. I opened the door for her and she walked out first. She told me, “Go home, I’ll lock up. I’ll see you at work soon.”

I felt awkward. “Ok, see you,” I said. I walked to the parking garage and wondered what had just happened.

I got ready for work the next day expecting her to have the worst attitude in the world. Between stop lights, I began to look at restaurant job posting websites on my phone. I walked with trepidation into the restaurant and saw her talking with one of the waiters over an order. I put my head down and walked to the back. I worked the whole shift, and she didn’t say one word to me. She was working hard, as rightly she should; “This is her business,” I thought. I was still turned on but was more relieved.

When I finished my shift, I went to my locker and picked up my stuff. I saw a green piece of paper with my things and my heart jumped. I knew it was from her. I said goodbye to everyone and began to walk to my car.

I pulled the note out of my bag and it read, “Last night was wonderful. You’re a great lover.

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