How to make working with a bitch worth it [M34/F40] [work] [fiction] [oral] [penetration] – Short Sex Story

My work is a sausage fest. Out of over thirty-five employees at my location, four of them are women. Two are old, one is a MILF, but hides in the offices and is rarely seen by the operations team. The last, named Bailey, is the operation managers back up, along with her main job. She’s nice most of the time. But, when she’s in charge a few times a year, she turns into a total bitch. Nobody likes working for her, and, honestly, she doesn’t find out our jobs and thinks we’re all lazy.

Luckily, for me, I was moved to another area late last year and basically became my own manager, working with, instead for, the operations manager. Basically, when Bailey is in charge, she can ask me to help out, but can no longer order me around. At least, that’s how it’s supposed to work.

Over the last seven years that we’ve worked together, me and Bailey actually get along pretty well, even when she’s in her bitch mode. I like to flirt with her, have straight up told her that if she needs to relax, I’ll make her feel good, and nearly got her to send me a picture of her boobs last time she was in charge.

When our operations manager left for a two week vacation last month, I knew it was gonna be hell with Bailey in charge for two weeks. But, I figured I would have some fun and try to get that picture finally.

The days that I work, I’m the second person at the facility, coming in at four in the morning. I typically have a couple hours to do my own job before I begin getting called to help out in other areas. To my surprise, I received a call from Bailey at five in the morning, asking me to come see her in the office. It starts.

I drove up to the office building, walking in too Bailey behind the counter, filing some paper work. She was almost six feet tall, just turned 40, had blonde shoulder-length hair that was pulled back in a ponytail, and was wearing purple shorts that looked like sweats, and a gray sweater. She was all the time cold, despite it getting over 100 degrees during the day. As she bent over, I could tell she didn’t have any underwear on, something she had told me she never wore.

Turning around and looking at me, she said, “Good morning, are you busy today?” I leaned up against the counter and said, “I’m always busy. What do you need?” She sat down in her chair, looking at her computer, “I need your help today. Everybody is behind.” I told her, “I’m behind too, I have orders due last month I’m trying to get done. You want my help, you know what to do.” She shook her head at me, “fine, I’ll send one. Just when those guys get here, get with them to see what they need.”

That was easy. Should I press my luck? Why not? “I don’t know. A picture might not be worth it. I’m pretty far behind and trying to make a push to get caught up. Plus, these guys have been slowing down lately. I might need more.”

She looked away from her computer at me, “like what? A blowjob?” I said sure, why not? And she replied back, “I don’t even give my husband those, so you’re outta luck. Should have taken the picture.”

“Nah, you’re outta luck. You want my help today, I’ll take a picture, let me play with them, and maybe ride me for a few minutes, then I’ll think about helping.”

I turned to leave as Bailey said, “Whatever, you’ll come help.”

I didn’t end up helping that day. I did keep tabs on everybody, letting them know to call me if they fell behind. Hell, most of them have my number and don’t need to go through Bailey to get my help.

The next day, I had been working in my area for about fifteen minutes when the offices yellow golf cart that they used to move around the facility came into my area. I turned off my equipment and walked up to Bailey, who said, “so, where we going to do this at?” I asked what and she said, “flash you and fuck you. Need your help today, so I gotta do what I gotta do.” I told her, “just send me a picture and I’ll come help if they need it. I’ll keep track of everybody and jump in when needed.”

She got off the cart, “you don’t have to worry about a sexual harassment claim or anything. I’m horny and I’m wondering if getting laid in the morning will help me not be so easily upset at everybody.” I said alright and pointed her towards my office.

Once in, I turned to shut and lock the door, turning off the lights as I did so. The office had a few windows that let the light of the rest of the area in, but with the lights of the office off, nobody could see in, if they tried to. I turned to Bailey, and gestured towards her shirt. She lifted it up and over her head, taking her bra with it. Her breasts weren’t the biggest, maybe a large B cup, but they were surprisingly firm for being forty years old. I reached out, taking her breasts in my hands, squeezing them before moving to her nipples. I rolled them in my fingers, lightly pinching them.

I was sitting down in my office chair, and I rolled it closer to Bailey, leaning up to her left breast, and sticking my tongue out to lick around it before sucking it into my mouth. I continued to pinch her right nipple, before switching over and licking and sucking on that one.

Pulling away from me, Bailey said, “you turned on yet? Let’s get this over with.” I reached for my basketball shorts, my ordinary work attire during the summer, pulling them and my garments off just enough for my cock to spring free. I know I’m not the biggest, at nearly six inches, but I’m not a pencil dick, at least, and have some girth to me. I was expecting Bailey to make some bitchy opinion about it, instead she said, “Wow, that’s actually impressive. This might just be worth it.” Like yesterday, she was wearing another pair of shorts, and she immediately pulled them down. She had a neatly trimmed bush right above her pussy, that appeared to be wet already. She stepped her legs over me, grabbing onto my cock with one hand, and then lowered herself down on me, moaning as she did so.

Bailey wrapped her arms around my neck, her feet just barely hanging off the ground, and started to rock her hips back and forth on me. I grabbed her ass, helping rock her, then leaned forward, taking her nipples in my mouth again. She started to bounce harder and faster, her moans getting louder. I was bucking my hips up to met her every thrust. I told her I was getting close, asking where she wanted me to finish. She moaned inside her and I grunted and moaned as I exploded inside her. Pulling her down on top of me, my cum filling her up.

When I was done, Bailey stood up, shaking her breasts in my face as she did so. She got dressed as I pulled my shorts up and we left my office together. When she got in the golf cart she said, “I better see you helping today.” I told her of course as she drove away.

I did end up helping out that day. And the next day. And the next day. Like I said earlier, when Bailey is in charge of everything, her lack of actual work knowledge, really hurts the team. It was that third day of me helping them out, ignoring my own job, that I finally said something to Bailey about it. I sent her a text that said, “you know, listening to you bitch and moan on the radio makes me want to pull my shorts down and stick my cock in your mouth.” I wasn’t expecting a reply, so I was shocked when she texted back to meet her in my office in ten minutes.

I was waiting for her in my office when she came in, shutting and locking the door and turning off the light as she did so. She said, “you have five minutes. Make it fast.” She fell to her knees, pulling my shorts down with her, taking my cock in her hand, jacking it off to get me hard. “I thought you didn’t give blowjobs?” I asked her. Before taking me in her mouth, she said, “I was lying. Of course I blow my husband, I just didn’t want to blow you. Until I saw your dick the other day. Now, fuck my face.” She immediately begun bobbing her mouth up and down my cock. I placed my hand on the back of her head, helping guide her, make her take more and more of me in. Once she started to deep throat me, I started to create up. I grabbed onto her head and started to buck my hips back and forth, making my balls slap her chin. When I was close, I warned her, and she moved her mouth so only the tip was inside her. She wrapped her hand around me, jacking me off until I started to cum into her mouth. When I was done, she removed her mouth from me, showed me the cum inside, then turned and spit it out in my office garbage can. I pulled up my shorts as she went to leave, but I grabbed her arm and pulled her away from the door.

“You said I have five minutes, I still have a minute left.” “That was just to blow you, I need to get back to the office,” she replied back. “Nope, not until you flash me.” “Fine,” she said, and started to pull her shirt and bra up. Once she freed her breasts, she shook them, making them bounce up and down a few times, then pulled her shirt and bra back down. “That better? Can I go now?” She asked me and I told her yes.

Later that day when I went to leave, the office was empty besides Bailey. I was saying good bye to her when she said, “Thanks for making this week not so stressful. Might have to do it again next week.” I told her any time, my office door was all the time open. Or shut, for her.

NSFW: yes


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