Workplace Shenanigans

I think everyone's had a boss that liked to drink a bit too much and flirt a bit too much, but I was fortunate that my example was a fiendishly hot 45 year old woman. Though she was nearly double my age, and married, I still sensed that her flirts weren't just innocent fun...

It finally happened one Friday morning, at 3am. We were on the night shift together with some other employees, serving the regular menagerie of drunks and stoners finishing up after a night out.

She came out of her office with a bottle of Jack Daniels, taking sharp swigs. Commenting on how great our uniforms (that she picked) looked around our bums, she sidled up behind me and gave me a quick pinch. I jumped up and turned around, thinking to confront her but only getting her cute smirk. She asked if I wanted to come back to... read more

The boss had always text or suggested that we should have sex at work in the middle of the day, he would often suggest that we meet in one of the many rooms that were upstairs and overlooked the showroom floor. It always excited me the thought of being fucked while looking out at people below...
Directly outside the boss's office was his manager and directly opposite him was his PA.
One afternoon his manager had gone out for lunch and his PA was in the warehouse doing something, I walked into his office and he said walk around here I want to show you something, as I walked to the other side of his desk his pants were unzipped and his cock was standing tall.
He told me had been having thoughts of fucking me over his desk while no one was outside the office.
With that I closed the door and lifted... read more

When I was 20 I worked in a supermarket on the checkouts and as such I work with a lot of very attractive women. There was one in particular who I couldn't help but stare at. She was 18 and had long blonde hair, a perky nice sized set of tits, very sexy curves, a phenomenal ass and amazing legs that seemed to go on forever. She often knew I was checking her out and would deliberately bend over to show off her ass or if we were in the small cigarette kiosk, teasingly rub her ass against my cock if we had to squeeze past each other. On day we both had to watch many awful training videos. There was a small room that this happened in and due to the general noise of the store we had to have the door shut to hear them. The room was... read more

It all happened when I was in a meeting with my manager Anna. Anna was mid forties, divorced and hot. Anna and i have been working together for about 10 years, so we know each other well (That is what I thought so) During this meeting she asked me wheher or not I had a question for her. I said yes. I asked why all of a sudden xxxxx's were at the end of all of her work related emails. She was open to me and said she wanted me inside of her as she liked my fitter body and found me attractive. My cock sprang up to attention and I told her I would fuck her in her office after everyone else went home. Later that day I turned up hard and with pre-cum on the head of my cock. I knocked on her door of her office she... read more

His cock was too big for the biggest condom. Working out at the Venice Beach gym, LA his sweaty muscles were pumped. Captivated, silky wet love beads ran down my legs. I watched him hold himself out perfectly horizontal. All I did was my job, massaging his arm, after he injured it.

I was confined using walking sticks. He carried my bags upstairs to my room. Between my toes with that cock, then between my fingers, he massaged me, pulsing. Every crevice of my body, he worshipped. Every ache bar the one for him inside me, sated! He carried me next day across the hot sands. Returning he slipped his fingers deeper into me. I wondered how I could say no again. His tongue twisted, making me cry out. My bed became soaked in my own gushing. His cock was too big for the biggest condom. On day 3, I left... read more

I had a very brief, but crazy fling with a guy at my work many years ago. I was a legal secretary aged 24, and he was 38. The chemistry between us was palpable, but unfortunately I ended up getting hurt. I left the practice a while after, and some time after still we were having a drink and ended up talking about our affair. He had felt the same was I did - wanted to fuck within days of us working together. He knew it was 'wrong' and felt conflicted. Chemistry is a strange thing. The early days after it ended I became very miserable, but now I'm a bit more 'meh' and honestly wish him well.... read more