I ended up becoming my manager’s sidepiece because of my slutty kitty [FM]

I worked as a waitress for a few years. Not any special sort of place, just a restaurant/bar kind of place that did a fairly steady business. The restaurant was located in a fairly affluent area of town, so the tips were pretty good. They were even better if you could work the bar shift on a Friday or Saturday night. On those nights, we had live music and it was much less of a family crowd. The adult crowd bought more alcohol which, in turn raised the amount of tips waitresses would receive significantly. This was the kind of neighbourhood where a tipsy customer might casually tip $100 if they were in a good mood, and as a starving college student, I loved working those shifts. They made a massive difference towards my financial stability.

The restaurant I worked at did their best to spread those shifts around among the long-term staff members. It worked for most people, and it worked for me too most of the time I worked there. I didn’t want to work every weekend anyways, who would? I ended up with some unforeseen expenses though. My cat got out, and came back a couple of days afterward. I found out later that she was pregnant. Wanting to do right by my slutty pussy’s kittens, I was going to need to pay for some vet bills over the coming months, and I wanted to work as many weekend shifts as possible for a while, so I’d have some money saved up to cover those expenses.

The guy who owned the restaurant was a bit of a womanizer. We’ll call him Jeremy for the sake of this story. He was middle aged, and allegedly happily married, however he flirted relentlessly with female staff members despite his relationship status. He was bald, a little under six feet tall, with blue eyes and a fairly lanky build. Over the time I worked there, he had a couple of “girlfriends” among the staff and they’d always receive special treatment for being his side piece. In short, you’d get to essentially pick your own schedule as long as you were fucking him regularly enough, and while that did piss off some people on staff, namely anybody whose preferred shift you took, it is fairly commonplace in the restaurant industry for dynamics like this to form in my experience.

I had used Jeremy’s flirting to my advantage before, it had gotten me preferred shifts a couple of times, and he often didn’t charge me when I had lunch off the menu when on break. I knew I was going to have to do more than wiggle a little bit, and pretend I didn’t notice him staring at my cleavage if I wanted to be picking my shifts for the next few months. I had heard good reviews from women Jeremy hooked up with in the past, so seducing him sounded like a much better option than trying to find a sugar daddy, or getting another job. I wasn’t the first person he cheated on his wife with, and I wouldn’t be the last. I’ve made bad decisions before, ones that I felt bad about pretty immediately after making them. This was easy for me to rationalize though. My slut of a cat was having kittens, and the idea of throwing them out into the cold wasn’t appealing to me at all. I wanted to keep a couple of the little guys when they popped out.

My opportunity to ask Jeremy about working more weekends came after closing one night. It was a Thursday, and I hung back when everyone else was dismissed to ask him. We were in his office with the door open because nobody else was there. It was a fairly small room, with a desk up against one wall, and a worn black leather couch on the wall opposite it. I was sitting on the couch, and he sat in his desk chair, turning it around so that he was facing me. We were both wearing work clothes, which meant a button down top and khaki pants for him, and a tight black skirt, and tank top combo for me with dressy flats. I sometimes wore heels if I was greeting, but it was way too much pain wearing them all day if you were waitressing tables.

I explained my whole situation to Jeremy, leaning into the “I’m a helpless broke student” thing as much as I possibly could. I wasn’t lying, really. I’m sure I could have picked up a second job, but I was balancing classes at the time and that didn’t seem like something that I wanted to do. Fucking Jeremy just seemed easier, and I was fairly certain he’d try for it if I alluded to my willingness. He launched into an explanation about how weekend shifts are moved around between reliable staff to be fair to everyone, and how nobody would put up with him just giving someone all of their preferred shifts. It was a pretty typical speech that bosses give when they’re shutting you down for something you’ve asked for. I had a trick up my sleeve though:

“You always seemed to let Melanie pick whatever shifts she wanted to work.” My voice was soft, and I hoped, sultry as I said it. Melanie was a friend of mine who had worked at the restaurant almost the entire time I had been there. More importantly, she had given me intimate details regarding her arrangement with Jeremy, so I knew that behind closed doors it was far more explicitly a quid pro quo than they ever let on in public. He stopped talking for a moment, and just stared at me. I think he was considering his options, but I knew he had picked up on what I was alluding to because I could see his cock begin to harden in his pants, the outline running down the inside of his thigh a little bit.

“Yes, well I guess there are arrangements to be made for employees who are truly thankful for them.” He replied, leaning back in his office chair as he said it, and causing the outline of his hardened cock to become more apparent through the fabric of his pants. It took a great deal of my mental fortitude not to roll my eyes at his remark. Personally, it would have been a lot more fun for me if he had simply told me that he wanted me to fuck him for it. Instead, it seemed he was happy to make me beg for it. He was probably wondering how much about their little arrangement I actually knew too.

I sat up straighter on the couch, adjusting my top so that it sat lower on my breasts, showing off red lace which adorned the top of my bra. He watched me with lust in his eyes as he adjusted, and I decided to make him wait a little bit longer before asking. I played up nerves that I wasn’t truly feeling, crossing and uncrossing my legs while I fidgeted, causing my skirt to ride up further on my thighs. I knew that he’d have just shut me down if he weren’t interested, though neither of us had said anything out loud, it was pretty clear from the air in the room what was being discussed.

“I’d be extremely thankful, Jeremy” I said, keeping my voice in the same low tone I had used before. “I’m more than willing to put in the work. I have to pay the vet, so it isn’t like I have much of a choice.” I stood from my seat in front of him, taking a couple of steps closer so that I was directly in front of his knees. He shifted in his seat to look up at me as I approached, raising his hands to grasp my thighs just above my knees, his fingers digging into my flesh as he squeezed slightly. “So what changed your mind? You’ve had more than enough opportunity” It seemed Jeremy was done playing coy about what we were doing, because his hands moved up to grope my ass through my skirt as he questioned me. I pressed back into his touch, and smiled at him before replying.

“I just told you, I care too much about my cats not to do something.” Before I got the sentence out, my skirt was yanked up around my waist, and his hands were groping my ass through my panties. I hadn’t gone with the sexiest ones that morning, but they were lacy as well, and matched my bra. I thought they were practical enough for work while still also being sexy. Jeremy turned me around so that I was facing away from him, and delivered a smack across my ass. It wasn’t the hardest, but it did make a satisfying slapping noise which punctuated our conversation.

“Way to tell a guy you’re not into him. So I’m getting laid because your cat’s a whore?” That made me laugh, because it was exactly the kind of joke I had been making about my cat too. I grinned at him over my shoulder, and nodded.

“Melanie said you were a lot of fun” I purred back at him, wiggling my ass in his face and earning myself another smack across the ass, this one harder than the last. Jeremy turned in his chair, opening one of the desk drawers in his office and taking out a condom. He then tapped on his computer for a couple of moments before pulling up our schedule for the next month.

“Why don’t you have a look at the schedule, and pencil yourself in where you think best fits your current availability?” He had moved behind me, and adjusted me so that I was standing in front of his desk now. The most oblivious person on Earth could have picked up on what he was putting down, so I leaned forwards and gripped the edge of his desk with one hand, grabbing his computer mouse with my other and clicking the first Friday of the month. I heard Jeremy’s pants unzip behind me as I worked through the dates, scheduling myself for all but one weekend the following month.

Jeremy tugged my panties down, leaving them around my knees before he pressed the head of his cock to my entrance. I was scheduling myself for an open Wednesday shift as well when he pushed himself inside of me, causing me to moan. Melanie had not been lying. Despite the seediness of the arrangement, and his apparent lack of morals, Jeremy did have a very nice cock. It was curved slightly downward, and hit several lovely spots with each thrust inside of me. He quickly built to a steady pace, before grabbing my ponytail and tugging fairly roughly and beginning to rail me hard against the desk.

I was expending a good amount of effort attempting to keep quiet, but as he tugged my hair a second time, I remembered that the restaurant was closed. I moaned loudly then, and pressed back into him with each thrust he made. After a few minutes, he briefly pulled out of me to turn me around so I was sitting on his desk. I braced myself awkwardly against his desk and the brick wall behind me as he began fucking me just as hard in this new position, his hand moving to grab my throat rather than my hair.

I’m going to add a small note here. Gentlemen, if you’re going to be rough with a woman please please please ask her explicitly before you go for it. Jeremy had no qualms about using me like the fucktoy I had fully expected to become when I had hatched my plan, but I think probably the majority of women don’t want to be railed harshly by a guy who hasn’t discussed it at all with them beforehand.

Melanie had warned me that Jeremy liked to get filthy, and she hadn’t been wrong. I arched my back, and moaned with an open mouth as he fucked me, and he leaned forwards to kiss me before spitting into my mouth. I swallowed it without hesitation, and looked up at him with my best big doe eyes. He didn’t last much longer, it was a couple of minutes before he pushed all of his length into me, and let out a loud moan of his own as he came inside of me, into the condom.

“Took you long enough, I’ve wanted that for a while” He laughed, giving me an unceremonious pat on the ass before sitting back down on the office chair behind me. I turned around to face him and took a moment to adjust my clothes before I sat on the desk in front of him. We had a drink in his office before going home, and for the next few months, hanging back after close became a regular thing for me.

Source: reddit.com/r/gonewildstories/comments/xtxoao/i_ended_up_becoming_my_managers_sidepiece_because