Dirty Dawg: Big Boss Booty

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It had been a while since I got laid; too long in fact and I was fit to be tied. Work presented no opportunities as of late with the added enhancement of a nasty rumor circulating about me and Holly, (See: Dirty Dawg: Big Tit Derby) one of my coworkers in the mail room. There was some truth to the rumors however as Holly and I had engaged in some X-rated follies one Saturday afternoon. Her husband Derbin, a perpetual underachiever had lucked into a job at U.P.S bringing stability to their usually turbulent household and an abrupt end to whatever it was we were developing.

I managed to hang onto a tenuous friendship with Holly more out of ego than anything of true substance. I was actually coveting her massive breasts and the fact that she’d denied me the opportunity to pound the living shit out of her using Derbin’s employment status as a caveat whether we’d get physical or not. That being said, I didn’t seem to have any options around the office. It seemed like Human Resources was intent on hiring the most unfuckable women possible. I know how this sounds, but I’m distinctly particular about where I put my penis.

Friday Evening, 6:58 PM

It was the end of my shift and I was suffering the effects of an eight-hour bout of acute Blue Balls. Holly was parading around the office in a form fitting wife beater that accentuated her gargantuan bust in the most abusive manner possible for all the poor male and lesbian employees. She’d even left a few buttons undone treating only the bravest of us to a view of her cavernous cleavage. Holly put on a few pounds since we’d hooked up with everything appearing to land in her tits and hips. It was all I could do not to cop a feel considering our past. Holly was a true country girl with a solid frame built for power and prone to brawling as one overzealous coworker discovered after exposing himself to her. She was wearing a pair of jean print leggings that added to the visual offense seemingly disappearing into the crack of her chunky, looking butt.

“Checking me out?”

“Uh, I take the fifth Holly.” I replied salty after noting the smirk on her round face which still reminded me of a living cabbage patch doll.

“What’s the matter; not getting enough on the open market?”

“Like I said before, I’m taking the fifth.”

“You’re sounding a little put out honey; we still good and all so I don’t know why you’re copping an attitude.” There was a light glibness to her voice that told me she knew the reason behind my attitude. She seemed willing to stock the fires of a pending argument but I wasn’t going to let her off that easy.

“It’s been a little slow lately but I’m good; sorry about the attitude.” She stood there with a half-smile frozen on her face not knowing what to do since I apologized.

“I was there before, it can get a little grating at times but lately Derbin’s been beating the wheels off my pussy like it’s going out of style.” The joyous tone in her voice added to the uncomfortableness of our exchange.

“Yeah, is that right?”

“Sure it is, the other day I woke up after he jerked off all over my titties; I was a little pissed cause of the mess but he fucked me so hard, I forgot about why I was even mad.” Holly, how shall I put this? The young lady originally from Tampa Florida proper, lacked a few social graces.

“So, he’s on the Viagra now?” She did a double take at my question not realizing I was ribbing her.

“Fuck you talking about; this is all the Viagra he needs!” Holly cupped the undersides of her breasts jiggling them inches away from my face.

“Sure.” I replied sarcastically.

“You’re just jealous honey; Derbin’s taking care of business every day.” Her voice faltered a little signaling that I’d managed to throw her a little bit off kilter.

“I didn’t ask.” I reminded.

“You can’t handle this; you’re just mad.” Her comment doubled my resolve to give her nothing.

“We both know I can; I gotta go Holly. Tell Derbin to jerk one off on those big ass titties for me too.” I took the liberty of slapping her right butt cheek on the way out of the office as she gasped.

It was a gamble considering Holly had already pummeled two guys in our office and miraculously still retained a job. I ducked into the bathroom just in case Holly changed her mind for a piss break before stepping out in the corridor to find her clocking out. My gaze travelled down to her expanded rear as I noticed that Holly was wearing a thong.

“You clock out yet?!” I found my boss Martha, standing uncomfortably close behind me looking like she wanted to take me out.

“I’m about to.”

“Not yet, I need you for a little overtime; come with me.”

“Not even gonna ask are you ma’am?” I’d had enough of Martha raking me over the coals for the past few months ever since I’d made a target of myself after commenting on a photo of her daughter. It was sitting on her desk catching my attention as I made a few ill-advised calls thinking Martha was out to lunch. casino siteleri I was setting up an evening excursion making the mistake of describing the young college age student’s prominent breasts. I’d failed to notice Martha standing in the corner taking in everything I’d said. I’d always wondered why I hadn’t been fired those six months prior.

“I’ll ask you if you’d like to be looking for another job by Monday morning.”

“No ma’am.”

Her threat was clear and I made a mental note to start looking for another job as soon as possible. I didn’t like anyone having something to hold over my head. I was tired of looking at the rough-hewn forty-seven-year-old and fed up with her standoffish attitude which extended to everything she was in charge of in the office. Martha led me down to a sublevel which the company used for storage all the while talking at a mumble which left me clueless. It was her style I guess and it rubbed people the wrong way ninety percent of the time. Martha had this sort of oval shaped face in which the features on it appeared to be distorted giving her the look of a woman aged well beyond her years. Her wide flaring nose and thick lips served to make her eyes look smaller than they were along with what could be described as freckles or black heads dotting her cheeks. She wore her hair in long afro-centric braids drawn up into a jagged ponytail neck of hear the back of her scalp. Her body appeared blocky and masculine obscured under an extra-large collared, short sleeved business shirt and matching loose fitting pants that appeared a size larger than she required. People joked that she looked like she worked for UPS from Hell and the large, bulky work boots on her feet. I sometimes joked that she looked like Morgan Freeman’s evil sister or something. It wasn’t so much that she was unattractive, it was just that she appeared to be perpetually lost in thought when she wasn’t being an absolute bitch to her employees.

Martha directed me to move a large number of boxes around in anticipation of a pending company wide audit. These boxes were not light by any means and a lot had been down there for years leaving my hands and shirt covered with a considerable amount of dirt. I was wearing a white long sleeved Adidas shirt and jeans which ended up soiled and Martha could’ve cared less as she stood back admiring my handiwork.

“Well, we sure did a good job of getting this place whipped into shape.”

“We?” Martha stood back during most of the evening “supervising” the mass reorganizing of the room and hurling verbal barbs that had me wanting to flip her the bird.

“Don’t be insubordinate; you’re only two write ups away from the street boy. There are some boxes in the hallway; take them to my car parked in front of the building.” She never looked at my face as she walked around looking at the room.

“Yes ma’am.” I replied acidly.

“I’m driving a burgundy jeep grand Cherokee; there’s more than enough room in the back for the boxes. Don’t do anything cute, boy.” The manner in which she called me “boy” was grating and I found myself gritting my teeth.

“I’ll meet you downstairs in about ten minutes, boy.” She tossed me the keys like I was some kind of valet directing her attention to a terminal in the corner of the room.

There were seven more heavy boxes in the outside corridor that I struggled to get into the elevator dropping a couple by “accident” on the way to Martha’s car.

Friday Evening, 8:50 PM

“Good job.” I was stuffing the last of the boxes into the back of her vehicle when she approached me getting angrier by the moment. I was ready to tell her where to shove it when I turned around getting the shock of my life.

Martha was standing before me in an Adidas tank dress that was fitted to her body like a second skin. Her chocolate skin stood in contrast to the dark purple material covering her body. The triple stripes on her sides appeared almost neon in the darkness of the streets. Martha had this most pronounced “Pear Shape” I’d ever seen and the most distinct “Ass to Waist” ratio. Martha had what I termed an exaggerated “Coke Bottle” shape. It was mind boggling stopping time right there on that side street. This woman’s head didn’t fit the body it was attached to and I was at an immediate disadvantage as Martha fished around in a small purse producing two fifty dollar bills.

“I can’t pay you for the overtime; hope this covers the work you did. Thank you young man; I’ll take those keys now.” Her toned arm hung in the air offering the money as my gaze remained on her flat stomach and wide hips. I probably looked like the village idiot.


“Uh-Sorry, I got distracted ma’am.” She pushed the money into my hand with a sly snicker while gingerly pulling the keys from my grasp.

“Checking me out little boy?”

“UHM; NO!!”

“Really?” Martha flashed me an uncharacteristic smile before gently shoving me aside to close the back door of her güvenilir casino car. My gaze was rewarded with a view of her backside which was not only large but thick and voluminous in girth. Not only was it wide, but it seemed vertically elongated and chunky with each huge cheek a muscular looking oval. The fit of her dress left no mistake about the fact that Martha wasn’t wearing panties. I was struck dumb at the sight as my cock elongated with the jack knife action and speed of a switchblade.

“You ARE checking me out, aren’t you, boy?”

“I’m not blind.” My ego wouldn’t allow me to simply answer her question.

“Hell, I can see that; I just want to know if you like what you see, boy?” She was starting to get into my ogling raising her arms while doing a pirouette for me to get another view of her dimensions. I marveled at the manner in which her butt stuck out far with a shelf like quality that could have easily supported a mug of beer.

“I fucking love it ma’am; why’re you always calling me boy?” The question came out of nowhere without conscious thought on my part.

“Why are you always calling me “ma’am”, huh?” She struck back quickly.

“Because you are my boss.”

“Well, just call me Martha; you make me feel like an old lady, son.”

“You don’t look like an old lady to me.”

“That’s because you’re looking at my ass.” I facepalmed realizing that I’d never stopped glaring at her lower half even while she was talking to me. Martha didn’t sound all that upset about my actions.

“Sorry.” She laughed an older woman’s throaty, deep belly laugh making me feel like a kid after all.

“It’s okay, I’m used to it; why do you think I wear those bulky clothes at work? No one would ever take me seriously if they knew what I was working with.” It made perfect sense to me; I was still burning a hole in her dress.

“Yeah; I, can see what you mean, in fact, I’m all messed up right now Martha.”

“How so?”

“I don’t want to offend you; I feel like I’m really getting to know you right now.” She continued laughing as I tried to explain myself.

“I bet you do; I can see how much you want to “know me” boy.” She reached out touching the rising tent in my pants with a pointer finger and laughing when I nervously jumped back. Martha really seemed to be getting a kick out of getting my goat with her body.

“Very funny Martha; you gonna hold that against me?”

“Why reward you?” It was my turn to laugh this time as she took it all in with her arms folded across her modest chest.

“Well, I did help you out with those boxes.”

“And I paid you.” Martha motioned towards the money still visible in my fist.

“I’d be happy to take it out in trade.” I offered the money in my outstretched palm as my boss did a doubletake rolling her neck in a stereotypical manner.

“Are you serious; you do realize I’m your boss?”

“Sorry, you had me at hello; seriously though, you caught me off guard and I’m at a loss how to move things along. I’m usually more savvy but your curves are killing me Martha. I-I mean fuck, I know I probably shot myself in the foot right now…” My words trailed off as I crashed verbally.

“You think?” She laughed putting me at ease.

“Big hole in my foot, Martha.” I scratched my head feeling like the village idiot. Martha jiggled her car keys in her hands staring me down before turning to enter her car.

“Don’t worry about it; besides you couldn’t handle this anyway, boy.”

“Yeah but who’s running?” I blurted out figuring she would dry away no matter what was said. It was a face saving move designed for my failing ego. Martha surprised me by opening the passenger side door of her jeep grand Cherokee. For some reason, I got in to the strains of “Magic Mona” by the Phyliss Hyman playing on her radio. There was a sly look on her face that made me feel like some inexperienced virgin as she cradled the back of my seat backing out of the parking space. The old-school tunes continued through our jaunt down the next few streets until we got onto the freeway. I was worried because she was going in the opposite direction from where I lived but I couldn’t find my voice to inquire about our destination. “People Make The World Go Round” by the Stylistics serenaded us as she drove onto Western boulevard humming the words to herself having not regarded or spoke to me since I sat in her vehicle.

I was familiar with the neighborhood having experienced an eventful street breakup with a self-proclaimed hoodrat in the area two years prior. This wasn’t exactly a safe place to be caught during the evening hours being on the borderline between two warring gang factions. In the past I always made it a point to keep my trips through the area as brief as possible. Martha was driving with her right hand on the steering wheel while the other was checking messages on her phone.” Inside My Love” by Minnie Riperton was drifting through the car as I found myself bathed in canlı casino a light bluish illumination that emanated from a large rectangular sign hanging from the side of a drive in “hood” motel. Martha was singing along with music doing a surprisingly good job. I wondered about her daily life measuring my place in it minute as it might have been. Part of me wondered, or worried what would occur after she parked.

“Look in that glove compartment and give me that little green coin purse.” She casually ordered putting the engine in park. I followed suite watching as she removed and lit a joint taking a few puffs before regarding me with a knowing smirk.

“What?” She removed the cigarette blowing a wisp of cigarette smoke into the air. I noticed her arm cradling the back of my seat again as she leaned forward bringing her weathered features inches from my face.


Her lips appeared too large for her narrow, weathered face devoid of makeup telling the tale oft heard of strong, black women. Her demeanor left me a little put off with slivers of stereotypical, female masculinity common in our community. During the early days of my youth it had always thrown me off balance leaving me exposed as a nervous teen to throngs of heckling sisters. In fact, I didn’t come into my own socially until my early college years. I felt like Martha was challenging me, challenging me to assert my manhood by simply leaning over like some kind of shark. I was determined to prove her wrong if she thought of me as prey.

Friday Evening, 9:57 PM

My own prominent lips pressed against hers in a serious of light bird kisses I hadn’t intended before coming together with Martha’s mashing wetly together. I could taste the joint mixed with the strawberry flavored chapstick she’d coated her lips with before we’d spoke. Before I knew it, her tongue had found entrance into my mouth swirling around in a sensual manner that had an immediate effect on the tightness of my pants. Her teeth nipped on my bottom lip before Martha began sucking on it before going at it again. My hand cupped her left breast; my thumb rolled a prominent nipple making the older woman shudder. Her own well-manicured nails raked my crotch before her thin fingers pinched my tumescence.

“So, you’re getting a room or are we just fooling around?” She asked plainly after we broke our embrace.

“Uh; yeah, right?” I felt even more inexperienced as I fumbled for my wallet.

“Hope you’re not expecting me to pay for a room, boy.”

“Nuh-No ma’am!”

“Room?” Her fist hung in front of my face as the pointer finger extended towards the check-in window. I nearly tumbled from the car cursing myself all the while for coming off like some nervous cherry boy fucktard. I could hear sirens in the distance as I passed a chubby prostitute and her john heading off to a room to do their business. I was starting to resent my place in this approaching tryst and Martha’s “Alpha Female” attitude as I paid the thirty bucks to the window clerk mumbling small talk to the inattentive Korean teen. He was watching some reality show from his country.

“Room Five; three hours!!” His tone made me want to take him to task for his attitude but luckily, I was distracted by the chirping sound of Martha’s car alarm being switched on. I could see the light from her joint in the darkness and her outrageous pear shape accompanied by the buzzing of the hotel door. I was struck by her proportions pausing to watch her walk into the room leaving the door cracked. Her silhouette reconfirmed and vitalized the lust that had waned from Martha’s initial presentation goading me into a purposeful jaunt over to room five.

As soon as I pushed the door open, Martha was waiting grabbing me by the collar and shoving her tongue into my mouth. Her hands were locked together in the small of my back as my own found the swell of her prodigious backside. My hands drew from the top of her buttocks to her cinched waistline and back again taking stock of the extraordinary disparity. I’d became greedy dipping a bit at the waist to get more of her big butt into my palms when Martha suddenly shoved me onto the bed. I took silent exception at her roughness sitting up on the edge of the bed to find myself peering at her washboard abs and crotch. Martha took another hit from her joint waiting expectantly as I traced the shape and form of her rounded hips. The form fitting dress extended down to the top of her calves. I reached down rolling the material up until it was resting easily on the top of her hips.

“Where are your panties?” Her mound was shaved clean provided a look at her juicy, looking cameltoe.

“Are you serious?” Before I could retort, Martha slowly turned around revealing her thick, meaty elongated buttocks. “Donkey Butt” was what it would be called by those in the know if they were fortunate enough to get the slightest glimpse. I considered my fortune as I ran my fingers over her dark chocolate skin. I cupped the underside of her muscular, oval cheeks weighing and marveling each. Martha’s feminine scent was strong, even more when her thick cheeks were parted.

“You really want me to put some underwear on little boy?” She spoke like a woman who knew what she was bringing to the table.

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