Bitch Boss Ch. 01-02

After graduating from college with a degree in Accounting, I was thrilled when I got a job working for a large regional bank. It was such a relief to know that I wouldn't be searching for employment and might even be on a career path. I planned on continuing my education in the evenings to eventually become a Certified Public Accountant.

On my first day, I was nervous as heck as my boss, Phil introduced me to the other fifteen people in the department and showed me to my cubicle. I guess it was only natural that my first assignments were tasks that no one else wanted to do. No one likes starting at the bottom and paying their dues but I took my tasks seriously and wanted to excel at whatever duties were assigned to me.

I was the youngest person in the department so I kept mostly to myself. I kept my head down and did my work. There was an older guy, Ray, who sat next to me who was going to help me out and answer any questions I had.

On Friday morning at the end of my first week, I saw everyone's heads pop up from their cubicles when we heard the distinct sound of high heels firmly clicking against the floor and approaching our work area.

When a stern-looking woman appeared, everyone put their heads down but I was new and didn't know any better. She looked as though she was in her early forties with blonde hair pulled into a bun. She wore glasses and was wearing a white blouse and a skirt that looked like it was part of a business suit that came down to her knees. She was tall and pretty with nice long legs. I had no idea who she was.

When the woman walked past my cubicle, she saw me staring at her and asked, "What the fuck are you looking at? Get back to work."

I got scared and put my head down but looked up out of the corner of my eye without lifting my head out of fear it would get chopped off and saw her walking into my boss' office. There was some yelling before company security came and walked my boss out of his office.

The woman came out of the office and said, "George is now in charge of this department temporarily until we find a replacement for Mike. Now get back to work," and she walked off with that same stern look on her face.

When I knew that she had left the area, I turned to Ray and asked, "What the fuck just happened?"

"Well Gabe, that's Ms. Huffington. People around her call her the Bitch Boss while others call her the Widow Maker. She's a V.P. and oversees our department. If you cross her once, she'll fire you on the spot."

I decided to continue to do my job and try to blend in so I didn't cross Ms. Huffinton's path. At a minimum, I wanted to stay at the bank long enough to gain some experience that I could use to get a better job somewhere else.

For the next couple of months, I came to work on time, processed invoices so vendors could get paid, and stayed out of the line of fire of Ms. Huffinton. I liked to be at work early and often stayed late to make sure my work was done. On rare occasions, I would catch the elevator with Ms. Huffington along with several others. I tried to stay in the back so she wouldn't notice me.

The thing that caught my attention was that other people on the elevator would try to engage her in idle conversation and she would ignore them. Even a harmless "Good morning" or "Have a nice day," would not be acknowledged. Ms. Huffington wouldn't even smile or look their way.

I would think to myself, "Damn, she has earned the nickname 'Bitch Boss.'"

I was taught there are some basic common courtesies and she didn't display any of those characteristics. Ms. Huffington made everyone feel like they were peasants and not worthy of her attention.

The thing that struck me about Ms. Huffington is that she was quite pretty. She kept herself in decent shape and appeared to have a nice ass and decent breasts. Her long, shapely legs were her best physical feature. If only her demeanor was better, she might be an attractive woman.

The good thing about working for a large corporation is that I was able to meet other women. I was never a popular guy in school because I was tall and slim. I got bullied in high school and began to lift weights to help defend myself. By the time I got into college, I had a toned body. I will never be a big muscled guy but I'm in decent shape. I'm not the most handsome guy around but I'm not that bad looking either. I guess I still suffer from the emotional scars of being bullied so my confidence level isn't that great. That being said, I would have a date here and there but I wasn't having any long-term relationships. I seemed to be stuck in the "friend zone."

After working at the bank for a few months, I began to settle in and even got a slight raise after my probationary period ended and things were going well. I began to notice some questionable expenses coming through that caught my attention. They were for some cheap motel a couple of hours away in some small rural town. One day when another one came through I asked Ray about them.

"Hey Ray, I keep getting these invoices from Ms. Huffington to reimburse her for some motel. Do you know what this is about?"

"I like you, Gabe, so please take my advice and just pay them. If you start asking questions, the Bitch Boss will make your life miserable at best or fire you at worst."

"Okay, message received. Thanks for the advice."

It still got me curious but I didn't think too much of it until I went on a camping trip with some friends and ended up passing by the motel on our way. It looked like a pretty run-down place, not a place where a woman of Ms. Huffington's stature or pay scale would stay. There was some dive bar next door too. It just didn't make sense to me.

When I got to work on Monday, I decided to look at the history of the invoices for the motel. There seemed to be a pattern that we'd get an invoice in the middle of every month. It looked suspicious other than that it was for a relatively small amount of money. It didn't make sense that Bitch Boss would do something foolish for such a small amount of money. I was still curious but it wasn't my job to question expenses, it was to process the payment.

Those invoices weren't an important part of my job. I was processing invoices for much larger amounts so they didn't consume me until I got another one the next month. I was a single guy and didn't have any plans for the following Saturday so I decided to take a leisurely drive and have a drink at the dive bar next to the motel.

I felt a little foolish driving all that way just to satisfy my curiosity but it was something I felt I needed to do. As soon as I walked into the place, I saw several men sitting at the bar and they immediately turned around to stare at me. It was obvious that I wasn't one of the regulars dressed in my khaki pants and polo shirt. They looked like they were construction workers, farmers, or did some other type of manual labor work.

It was too late to change my mind so I saddled up to the bar, ordered a beer, and scanned the menu. The bartender engaged me in a conversation and it was obvious that he was trying to pump me for information about myself. I told him I was passing through and got hungry so I decided to stop in. I ordered a burger and sipped my beer while minding my own business.

As I looked around, the inside of the bar wasn't as bad as the outside but it was still a dive bar. It had a small sitting area near the bar with a larger backroom. It wasn't someplace I could see Ms. Huffington patronizing. She was such a stuck-up bitch, I figured she wouldn't be caught dead in there.

As I was sitting there with my beer and waiting for my burger, I overheard an interesting conversation among the other guys at the bar.

"I couldn't make it last week. Did I miss anything?"

"Yeah, Bev showed up as promised and damn, she was on fire."

Ms. Huffington's name is Sandra so I didn't think they were talking about her.

"Oh yeah, what did she do?"

"There were five of us here and she did us all. She sucked all our dicks and fucked us. She must have cum four or five times herself. She even took Freddy back to her room at the motel and fucked him til his balls were dry. I can't believe a hot-looking lady like that comes in here to get laid. She could pick up anyone back in town."

"Maybe she knows too many people and comes here to let loose."

"That must be the case but I ain't gonna miss next month if she shows up."

"Yeah bro, me neither. She's one hot piece of ass. I wish my old lady liked dick as much as Bev."

I was thinking, "Could they possibly be talking about Ms. Huffington? Naw, she'd never do something like that. Maybe so, but why is she renting a room at the motel next door? Maybe she's having an affair and this is a good hiding place."

Even if they weren't talking about Bitch Boss, it still sounded like an interesting situation. The thought of some hot woman coming into the bar and taking on all comers was intriguing. The guys went on to talk about other times she'd been there and taken on more guys. Was it just a coincidence that Ms. Huffington was around every month when this woman got gang banged? Did she know the woman? Could it be her?

I ate my burger and had another beer before I left for the long ride home. It was worth the trip just to hear that story of some hot woman who showed up at this rural dive bar once a month to get laid by anyone who happened to be there.

On Monday, I happened to see Ms. Huffington getting a sandwich in the cafeteria while I was eating lunch. She would never lower herself to eat with the workers and would take it back to her office. However, while she was there I couldn't help but undress her with my eyes.

She always wore longer skirts or slacks but she had a nice ass and shapely legs from what I could tell. Sometimes, I could see her bra through a white blouse and she appeared to have nice full breasts. I imagined her without her glasses and her hair let down and from what I could tell, she was a very pretty woman. I'd never seen her smile, only that stern look or a scowl but she had pretty blue eyes.

As she was in line to pay for her lunch, I was thinking, "Could it be possible that Ms. Huffington was the woman who would have sex with multiple men in the back of a dive bar? Naw, there was no way."

Even if it wasn't Bitch Boss, it sure was fun to imagine her dressed nicely and being stripped of her clothing in the back of a bar and having guys lined up so she could suck their dicks or fuck them. I wondered if she even took it up the ass. I went home that night and jerked off thinking of seeing Ms. Huffington getting gang banged and getting a piece of her myself. I imagined her on her knees sucking my dick and laying on an old wooden table with her legs spread while I drilled her pussy hard.

I became obsessed with thoughts of Ms. Huffington going into that bar in a couple of weeks. I even turned down an invitation to a party so I could travel there again just to satisfy my curiosity. I had to know if it was her or not. If it wasn't, maybe I'd be allowed to participate in the gang bang anyway. I hadn't gotten laid in a while and needed to get some relief anyway. I had nothing to lose.

On that Saturday, I planned my trip carefully. I doubted Ms. Huffington would recognize me because she was such an arrogant bitch and didn't care about anyone but herself. However, I couldn't take any chances. I normally wore contact lenses at work but decided I should wear my glasses. I put on my flannel shirt, jeans, baseball cap, and hiking boots to try and fit in with the crowd. They would know I wasn't a regular but I couldn't be too obvious about it either.

A million thoughts were running through my mind on the drive to the dive bar. I also got nervous and almost turned the car around several times. I didn't want my adventure to get me fired but on the other hand, if Ms. Huffington was there, she'd have more explaining to do than me.

I got to the bar around 8 PM and ordered a beer and burger. The same four guys were at the bar and I overheard them saying they were expecting Bev to arrive in half an hour or so. I don't know if I was nervous or just anxious to see if my hunch would pay off but I was definitely unsettled while eating and drinking.

At about 8:45, the door to the bar opened and everyone turned their heads to see a gorgeous, long-legged blonde walk in wearing a tight skirt that barely covered her ass, black thigh-high stockings, five-inch, open-toed black heels and a white cami crop top that left no doubt she wasn't wearing a bra. Her unencumbered tits bounced freely under her top and her dark areola were very noticeable. She was wearing a lot of makeup too. She looked like a hooker.

My first thought was, "Is that Ms. Huffington or not?"

She resembled my boss but she was dressed so differently and had on so much makeup, it was difficult to tell. However, when she greeted everyone, there was no doubt in my mind. My Bitch Boss was going under a pseudonym, Bev.

"Hello, boys. Did you miss me?" she said as she strutted to the bar to greet the four guys and the bartender.

"Fuck yeah, Bev. We've been waiting for you."

"You look hot tonight, Bev."

"I feel hot too, boys. I hope you're up for it."

"Shit, I'm already up for it, darling," one guy said and everyone laughed.

The bartender then asked, "Do you want the usual, Bev?"

"Sure do, Donny."

The guys moved aside so Bev could sit down in the middle of them and she kissed them all. Everyone, including me, got a perfect view up her skirt as she climbed onto the bar stool. She wasn't wearing any underwear and my heart started to race as Ms. Huffington's shaven pussy was exposed for all to see. Holy fuck, I had to pinch myself to make sure I wasn't dreaming. My stuck-up, arrogant boss was here to get gang banged. I was now hoping they weren't going to throw me out of the place. I had to see this for myself. I desperately wanted to fuck the gorgeous woman sitting at the end of the bar too.

The bartender saw that I was almost done with my beer and came over to see if I wanted a refill. Before he poured another he warned me about what was going to happen.

"Things might get a little wild in here. If you aren't up for it, I'd suggest you leave now."

"No, I'm good. I think I have an idea of what's going down."

"Well, you better be able to keep your mouth shut or I can't guarantee your safety."

"Hey, man, whatever happens here stays here."

"Good. You might even get lucky yourself. It depends on how Bev is, uh, feeling tonight."

"No problem. I'm good."

He poured my beer and went over to talk to the others where I assumed he told them I was cool with what they were planning. Everyone looked my way and I got scared that Ms. Huffington would recognize me but so far, so good. I panicked even more when they invited me to join them.

"Hey buddy, why don't you come on over and join us?"

I grabbed my beer and slowly walked to join my newfound friends as the bartender went and locked the door and turned the sign over to say "closed." This was the moment of truth. If Bev or Ms. Huffington recognized me, this would be the moment. I had a difficult time looking at her out of fear she would know I worked for her. However, keeping with her selfish personality, she had no clue who I was.

Bev commented as I approached," Aw, look at this, it looks like we have a shy one here."

As she said that, Bev uncrossed her legs, spread them a bit, and crossed them again. I stared at her exposed pussy until she covered up again. I then focused on those long stocking-covered legs and the bare skin of her thighs above them.

The guys introduced themselves but I wasn't paying close attention to what they were saying. I was too busy checking out my scantily clad boss. They introduced Bev and I had to think quickly to make up a name so I didn't risk revealing my true identity.

"I'm, uh, Al."

"Nice to meet you, Al. You're pretty cute and young too. I like 'em young," Bev commented.

I was able to relax now that I knew Ms. Huffington didn't recognize me. We were making idle conversation while the five of us and the bartender were checking out Bev. It was clear she was enjoying being the center of attention while we were practically drooling over her.

When she was on her second drink, some of the guys began touching her legs. Finding no objections from her, the others took turns fondling her breasts. It was such a bizarre situation that it took me a moment or two to join in. Ms. Huffington looked awesome and felt even better.

The nylon of her stockings was so soft as well as her bare thighs. Her luscious breasts felt even better. It was a surreal situation to be standing there squeezing and touching Ms. Huffinton's body along with five other men. Before long, she was purring softly to the touch of the six of us, including the bartender.

They saw Bev was heating up and someone unbuttoned her top to expose her pert breasts. Guys pounced on her immediately to take turns sucking on her nipples. When it was my turn, Bev was rubbing the back of my head while moaning as I wrapped my lips and tongue around her nipple, sucking on it like I was nursing. One of the guys had to pull me off of her because I wasn't moving voluntarily.

Someone was working their finger inside Bev's pussy while a couple of others helped take her top off. I was rock hard by the time I got my chance to finger fuck her. Bev's pussy was wet and tight despite her age. She was moving her hips around in an attempt to fuck my finger in return. My goodness, Bev was fucking horny that night.

When someone said, "Let's get her in the backroom," we all grabbed our drinks and I followed everyone back there.

I stopped to use the restroom first and boy, is it difficult to pee with a hard-on. When I got out, I pulled out my phone to take some video of Bev who was being stripped of her skirt and went down on her knees to start sucking whatever dick was in her face.

One of the guys saw me and said, "Hey, that isn't cool," so I put my phone away.

I took my place as we surrounded Bev and pulled out my dick so she could suck it along with the others. I watched in disbelief as my naked boss hungrily went from cock to cock, deep throating each of them. Who would have thought that Bitch Boss had a secret slutty side to her. She appeared so conservative and uptight at work but once a month she turned into hot Bev, the whore.

When Bev got to me, she looked up at me with her big beautiful blue eyes and said, "Welcome to the party, Al," before she swallowed my cock.

Holy fuck, did she know how to suck a dick. I wasn't the most sexually experienced guy but I knew a good blow job when I felt one. Bev expertly worked her lips and tongue around my dick making me moan and almost causing my knees to buckle.

Bev went around to each of us a few times when she got up, bent over one of the tables, and asked, "So who's turn is it to go first? I'm extra horny tonight."

One of the guys replied, "We have some extra help tonight, babe."

"I'm going to need it, fellas."

As much as I wanted to step up, I was the new guy so there was no way they were letting me go first. I followed their lead and began to strip off my pants and underwear. A big burly guy with a scraggly beard was first to get behind her and slide his dick into Ms. Huffington.

She moaned loudly and said, "Oh god, I need to get fucked so badly. Give it to me good."

She didn't have to say that twice and he started to pound her pussy hard while pushing back against his dick. Her tits were flopping around as she was getting fucked. The bartender knelt in front of Bev on the table and stuck his dick in her face. She began to suck his dick while I watched my boss being spit roasted in a dive bar. The big guy fucking her was now playing with her tits.