Professional Development

I sat in a dark corner of the room and watched. My role for the evening was supposed to be strictly supervisory in nature, but I was slowly concluding I might need to step in and insure the task at hand was done correctly.

The room was filthy, dark, and drab, with peeling paint held on the walls mostly by all the graffiti sprayed over it, and a pile of trash and debris in every corner except the one I had claimed.

Two of my business partners leaned against the wall not too far away, though they too, were mostly in the shadows. They knew their upcoming roles; both had their cocks out and were slowly stroking themselves as they watched our newest associate engage in some on-the-job training.

Stan, the neophyte, stood in the center of the room, under the sole light fixture. On the square table in front of him was a nude woman. Her sobs were quiet, and yet they seemed to fill the dank and otherwise silent room. She was bound, her arms stretched out and up, a soggy cloth gag muffling her cries and screams. Her legs had been spread wide with her knees pushed towards her body and her thighs bound to homemade stirrups mounted under the table. Her bare cunt and ass were ready to be used, right at the table's edge. She lay on top of her dress, which had been cut open to expose her body. The shredded remains of her bra and panties lay on the floor.

Stan's cock looked rock hard, but rather than plowing the bitch's ass as he'd been assigned to do, he was hesitating.

"Oh for fuck's sake." It was Dave, the man closest to me. His voice was a low whisper, but I could here the impatience in his voice.

"Doesn't have it in him," Mike murmured. I could barely make out his words.

"Fucking bone her ass!" Dave commanded.

Stan put his well-lubed cock head against her asshole and began pushing. The woman sobbed louder. Stan's cock met resistance and slipped out of place several times. Finally, he got just the tip going in the right direction and started to open up the bitch's back entrance. Her peals just about broke my eardrums, even with the gag.

Stan had backed off. Fuck! To my side I saw Dave leave his post, his patience gone. He strode to the table, cock bouncing in front of him.

"Stan, what seems to be the problem?" Dave asked.

"Dude, she—"

"She what?"

"She's really scared."

"Of course she's scared. She's about to get her ass gangbanged by a room full of strange men. What is it about this you don't understand?"

"She's really screaming..."

"She's going to scream even more when you actually get your cock into her ass. Look Stan, it's going to happen whether you participate or not, but let me tell you: this is not something you can opt out of. Not and keep your job. Your choice. Fuck or walk."

Dave was laying things out plain and honest for Stan, but fuck, his timing sucked big time. If he continued to berate Stan, the poor fucker would never step up to bat.

I guess I should explain here that in addition to be the newest member of my team and inexperienced at...well, what it is we do, Stan was an anal virgin. No, I'm not talking about his anus (though presumably that too was virginal); I'm talking about his cock: it had never breeched an asshole.

Tonight was Stan's second assignment. His first assignment had been last week. It had been a quick and simple job: we had arranged for our target and us to get stuck in a "malfunctioning" elevator stuck between floors for 15 or 20 minutes. We'd forced her to her knees and made her blow each of us. I thought Stan had enjoyed himself, but now that I considered things, I realized today represented a pretty substantial step up in intensity.

Tonight had involved abducting our target in a van and hauling her into my empty warehouse kicking and screaming. She had fought us like a rabid wolverine, and though not a damn one of us would enjoy admitting it, it had been a serious workout getting her strapped down to the table. The ass fucking she was about to receive was going to be, let's just say, intense, and she was going to scream a lot, at least at the beginning. Stan just might not be up for the task at hand.

So this rapidly disintegrating situation was mostly my fault, I realized. Yet, I had put a fair amount of time into Stan's professional development, and I strongly preferred to salvage the whole situation as well as my new employee. Not to mention, there was a repeat client involved who expected our job tonight to be very, very thorough.

I walked forward, to the opposite side of the table from where Stan stood.

"Boss, I—fuck! I've got this," he protested. He lied. He didn't have it; he was on the path to failure, and it was now up to me to pull him back on track.

I grabbed the sobbing bitch by the hair and pulled her head up so Stan could see her face better. She howled in fear and surprise; obviously she hadn't heard me stealthily approach the table.

"Look at her, Stan." My words were soft, but when I spoke softly, people tended to get more scared, not less. I continued to speak to Stan, but I whispered the words into the bitch's ear. Might as well add a little to the ambience.

"She's crying, Stan. She's crying because you're standing there about to ram your cock up her ass, and there is nothing she can do about it. She's scared. She wants to get free and run away, but she can't. Look at these sweet tears, the sheer dread in her eyes. She knows what's coming to her."

"Yeah, it's not supposed to be—" Stan began to protest, but I cut him off.

"Yes it is Stan. This is exactly how it is supposed to be. I'm sorry if you thought it would be different, but this is how it is. Everything is exactly how it is supposed to be in this room. And we all have a job to do, including you. Now, Dave is right. You, unlike this little slut, are free to leave at any time. But it's all or nothing. You walk away now, you walk away from my company completely.

"I don't think you want to do that, Stan. Mike doesn't think you have it in you to do this job, but I think you do. I think you want to impale your cock into this." I gave the bitch's head a small shake. "I think you know how good her ass is going to feel. Where else in the world can you do this, Stan, and get away with it with such surety and impunity? Where else can you take what you want like this? I'm providing this opportunity, the first of many I promise you."

I could tell I was getting Stan's head back on track. He was staring at the bitch spread open in front of him.

"Stick your fingers in her cunt." I instructed. He complied almost immediately. I have that effect on people, even alpha male types. "Describe."

"She's wet."

"Because..."

"She wants it."

"Part of her does. That's why the little slut ended up here in the first place, after all. But do you know what makes this job so fucking amazing? It's the part of her that doesn't want it. That part is scared shitless right now, Stan. Reach out and feel that fear. Taste it. Grab it." I caressed the sobbing woman's cheek tenderly, brushing away a few tears. More took their place quickly.

Stan's demeanor had changed completely. He actually looked a little—dare I say—mean? He leaned forward and lined his cock up with her puckered hole.

"Mmm...here you go, little bitch," I whispered to her. "Here it comes. You don't have wait much longer."

She cried out, "No, no, no!" except with the drool-soaked gag it sounded more like "dough, dough, dough!"

Stan pushed his thick cock into her ass. The woman started screaming desperately, thrashing out as much as she could given her bondage. We always do a very thorough job in that regard, so she didn't manage to move very much at all. I held her head gently and brushed her hair out of her eyes. "Good girl. You just popped Stan's anal cherry." She screamed again. Despite both of them being lubed up, Stan had only gotten halfway into her, and was pushing slowly in by small increments. Damn, the bitch must be tight.

"That's it, Stan. Now pull out completely, and push it back in. The initial breech of her sphincters is what hurts the most, and you want to be able to enjoy her reaction a few more times before you start really reaming her."

Stan took my sideline coaching well. As he withdrew, her tight ass pushed the head of his cock out with an audible pop. Oh hell, yes, she was tight. Hell, for all I knew, she and Stan were popping each other's anal cherries. How sweet.

The screaming stopped momentarily as her pain abated, then started again as he re-invaded her. She had broken out in a fine sheen of sweat.

"How does it feel, Stan?"

"Ah! Fucking ah! Shit, it feels awesome!"

"Did you hear that, little bitch? He likes what he's doing to you. I don't think he's going to stop."

She moaned pitifully in response.

Stan pulled out completely and reentered her a few more times, drawing a scream of protest with each plunge. Finally, he buried his cock to the hilt in her rectum.

The throaty squeal she made when he bottomed out sent an electric shock straight to my own ragingly hard cock. Every muscle in her body had tensed up with pain. "Shh, shh," I cooed in her ear. "Take it like a good little girl. We're just getting you warmed up. You have 3 more cocks to take in that tight little ass of yours after Stan here." Her sobbing began anew.

I initially was just going to have Stan, Dave, and Mike do her, but the whole scene had revved me up, so I decided, what the hell, I'd jump in too. Four for the price of three.

Stan was going to town on the little bitch now, pounding her ass so hard the table was scooting forward about a centimeter with every third thrust or so. Her screams were turning to moans, slowly but surely.

I freed my cock and began stroking. Dan and Mike were doing the same, eager for their turns.

Her small tits were jiggling and shaking as Stan fucked her. Mike and I each grabbed a nipple and began pinching and twisting them. They were nice tits, like the rest of her. She was a pretty delectable little morsel all around. Smooth skin, not too thin, not too plump. She'd looked polished and coiffed when she'd walked out of her office building tonight, like she'd just stepped out of a high-class salon. But, I liked the more disheveled look she was sporting now, too. I liked the way her eye makeup had streamed down the sides of her face and smeared onto the table. I'm not one to overlook the nuanced details in life.

Dave would be up next, and he was already pushing his pants down and out of the way in preparation.

Stan finished with a roar and series of brutal thrusts. He was still gasping in pleasure and it looked like his legs were about to buckle underneath him. He bent over and placed his arms on the table to support himself. "Holy fuck!!" he growled hoarsely. "Motherfucker!" Little bitch was still crying pitifully, but the tears were well interspersed with moans.

Dave cleared his throat lightly, and Stan hurriedly pulled his cock out of the girl's ass and stepped away. He collapsed in a chair, still breathing heavily, then let out another moan of pleasure that morphed into a victorious laugh. I chuckled to myself. Clearly the lad liked his job. He'd just needed a little kick-start to get going.

Mike continued tormenting the bitch's tits, and I pulled up a chair near her head so I could whisper more sweet nothings in her ear.

"Are you ready to take cock number two, little bitch?" I crooned.

She shook her head weakly. "Dough."

"No? Oh that's too bad. Because this one is bigger. Dave, come show her your cock before you fuck her."

Dave walked around the table so his large, erect member was in her line of sight. He poured a handful of lube on it and stroked its hard length. Little bitch started weeping again, but not before I felt a tremor run through her entire body.

"That'll open you up a little more, won't it, slut?" I asked her.

Dave stepped back into position and plowed his giant tool in to her all the way with no warning, just slow and steady. She screamed, but I could tell her voice was mostly used up, and she was running out of fight.

"You're very sweet," I whispered to her. "You smell like vanilla cupcakes. So pretty." She squeezed her eyes shut and turned her head away, as Dave continued her violation.

I grabbed her head and firmly turned it back towards me. "Look at me." She didn't want to, but she did.

"Good girl."

I wanted to see what was in her eyes. Pain, fear, tears, and—always—the beginnings of that sweet horror I've seen in so many women's eyes when they realize their bodies are starting to respond to things that disgust the rational part of their brains. That's what I do, and I do it well - I cut into their psyche and exposed the darkest, cancerous desires that lie therein.

"Now look at Dave," I commanded her. "Watch him fuck you."

Dave was a pretty mean-looking motherfucker, especially when he was on the job. He was the largest of us: 6'2", over 200 lbs. of solid, muscle-bound bad-assery. Shaved head, tattoos, looked like a biker, though he wasn't. I hate to say he was the token thug in my gang, so I'll just say he made an important contribution to our overall aesthetics.

He had a snarly smile on his face as he relentlessly pumped his cock in and out of her. If I was strapped on a table getting ass-fucked by Dave, I'd probably be pretty scared myself.

Her crying continued. I reveled in the sounds; all the sobs and wails and tears—they are the best fringe benefit my job could possibly have.

Dave was getting close to coming. I knew because he was describing to her in detail how he was about to spew a hot load in her dirty ass. Dave liked to talk dirty.

"Oh. Fuck. Bitch! Your ass is—ahhh!"

He growled loudly in pleasure as he came, and as he did, the woman arched her back and gave out a guttural animalistic cry as well.

The dirty little slut was getting off on it. Color me shocked.

Dave pulled his cock out, quickly getting out of the way for Mike, who promptly set to work himself drilling the woman's poor abused ass.

"Is she still tight, Mike, or did I stretch her out too much for you?" Dave asked.

"Pretty fuckin' tight," Mike grunted out between thrusts. The woman was moaning and clearly aroused now as my team continued the prolonged onslaught of her ass. Her butt cheeks were lying in pool of the juices that were streaming out of her cunt.

"What kind of slut," I ask the woman, "get's off from taking a room full of cocks up her ass? I mean, you don't even know us. We didn't even buy you a drink." I chuckled softly.

She moaned pitifully again and writhed around on the table. I noticed her legs trembling. And I swear to God, despite her bondage, she was making tiny pelvic thrusts in tempo with Mike's pounding. She was about to come again. Mike began thrusting into her fast and hard, and she screamed in pleasure. I felt her head pushing back into my hands as her entire body spasmed.

When Mike added his load to her ass he gave her right buttock a hard slap. She cried out, and he laughed.

"Boss, this bitch likes her ass fucked too much. It's hardly a punishment if she's coming every five minutes. Maybe she needs a little somethin' to remind her she's not supposed to be enjoying it so much." He gave her a dozen or so hard smacks on the ass that had her squealing in pain.

"Mike, if she likes her ass reamed, what makes you think a spanking is going to be any different?"

I was about to drill my own cock into her raw, red rosebud when I noticed Stan had rejoined the audience with a renewed hard on. What the hell, anything for my valued employees, right?

"Boy, you up for round two?" I asked him, and I could see the eagerness in his eyes.

Mike and Dave laughed.

"Gentlemen, we've created a monster," I said to them, then stepped back and motioned for Stan to go for it.

"I don't want to take your turn, Boss," he said, even though I knew his cock was twitching to at the thought of getting into her tight ass again.

"Don't worry, I'm taking my turn from this side of the table." I had walked around to where her head was conveniently close to the edge. I tore the gag off her, grabbed a firm handful of her hair and guided her face towards my cock. Her lips had locked firmly shut, so I just pressed the head of my cock against her mouth and waited. Sure enough, when Stan rammed into her ass again, she opened her mouth with a gasp, and I slid right in.

"Take it, little bitch." I said, looking down at her pretty face as she coughed and sputtered around my cock. I started working it in and out of her mouth, oblivious to any protests. Stan was barreling through his second go with amazing vigor. She was trembling all over again and moaning.

Continuing all the while to fuck her mouth, I bent across the table and grabbed her clit. We weren't there to get her off, but I could sense an immensity of need building in her, and I have to admit I was curious to see what would happen if I lit the fuse. I tugged and pinched her clit cruelly, all the while fucking her mouth as deep as I could. Her trembling increased. At some point she managed to maneuver my cock out of her mouth, and holy fuck, the noises she started making, hell, I can't even describe them. It was as though her vocal cords had morphed into those of some kind of wild beast. Her entire spine arched off the table, and her body shook violently as she came hard, yet again.

I resumed fucking her face, and by the time Stan and I unloaded in her, she was like a limp rag, quiet and spent. She hardly put up a protest when I made her swallow my copious load, or responded at all to Stan's lusty howls as he squirted his cum into her.

I squatted down next to the table so my face was level with hers. Her eyes were open but not focused on anything in particular. A drop of my cum hung from her bottom lip. "You missed a drop, little bitch." I tenderly swiped it onto my finger and tucked in into her mouth. "There you go."

We all toweled off our wet cocks and tucked them back into our pants, and I untied her from her bondage. She curled up in a fetal position on the tabletop. She said nothing, just lay there.

We left her there, ignored, while we gathered up the few items we had brought into the room and packed them into a duffle bag. I chatted briefly with Dave and Mike about some upcoming jobs, congratulated Stan on his strong comeback this evening. The three of them left one by one, leaving me alone with the little bitch.

When I looked back up she was sitting up on the table trying to put on her shredded dress. She looked dazed and confused. God, she was a real mess. My boys and I had worked her over well. I couldn't help admiring our work. A well-executed gangbang is an achingly beautiful thing.

I pulled a bottle of water out of the duffle and handed it to her. She glanced at my offer but didn't take it, then gave me a dirty look. I twisted the bottle open. "Drink." I commanded.

"Fuck you." Her voice was raspy, probably from all the screaming she'd done.

I glanced at my watch. "Technically, I'm still on the clock. I can force you if necessary. Drink it."

She drank half of the water. "You're a fucking sociopath, you know that?"

I smiled. "We all have monsters inside us, baby; I'm just more in touch with mine than most people."

She pushed off the table and tried to take a few steps on wobbly legs, the dress still in hand.

"You can't go out in that," I said, taking the dress from her. "There's a bathroom down the hall. I put some clothes in it. Don't step on any rusty nails."

"Fuck," she swore under her breath, looking around the room. She kicked a big, dead cockroach out of her path with her bare toe. "Christ, this place is a nasty pig sty. You should clean it up. Someone will get fucking anthrax in here."

"What, and mess up the ambience?"