CockSlut Ep. 03

I learned a few things during my first week as a cockslut. For one, when my boss said that sex stuff wouldn't happen every day, he lied. Second, I realized just how difficult it was to overcome a gag reflex. By that Friday, I still couldn't get much more than the head and another inch of bossman's cock into my mouth. He was cool about it though, said he got that I was still learning, and that I'd get there. I don't quite know how far "there" was, if he expected me to eventually suck it all down, or what. Oh, I also learned just how big he was. If you're interested in that kind of thing, anyway. You're here reading this, so something tells me you probably are.

My boss has a 10 ¼-inch dick. Yeah... yeah. Mine, on the other hand, is like 6. Yes, we measured. We had a contest, and the loser sucked-off the winner. Go figure.

I was getting used to some things though, like the taste of his cum, or the plug in my ass. Both were still new and unusual to me, but on their way to working into my everyday life. I wore the plug all the time, even at night. I had considered taking it out at home, leaving it out while I slept, but that seemed counterproductive. It would undo much of the day's training and stretching, and, just between you and me, I was starting to like how it felt. I even kept it in over the weekend.

Monday started like most days: blowjob first thing (this time with him standing), then not much for a while. I kind of just took up space for an hour before the boss announced he had to go.

"I've got a meeting downtown," he announced out of nowhere. I was on the couch, nude as usual, reading a magazine.

"Oh," I said, looking up. "Um... should I get dressed or...?" In the six days I'd worked for him, he'd never left until it was time to go home. I didn't know what the uh... protocol was.

"No." Oh, well that answered that. "You're going to stay here. There's filing to do."

I set the magazine down. "Sorry, what? Filing? I thought you hired me to..." I gestured with both hands to my nude body.

"I did. But now I need you to file." His shoulders raised and lowered in a shrug. "Your title is 'Executive Assistant', isn't it?"

"I thought it was 'CockSlut...'"

"You take the files here, and you put them in there." Molly (by the way, Molly isn't her real name. Just saying) pointed to paper boxes on the table, then to a row of filing cabinets against the opposite wall. "They're ordered by case number, then alphabetically. Think you can handle that?"

I grumbled. We stood in a long storage room, lit only by overhead fluorescents. There were no windows, no other doors except for the one we'd entered through. "You know, I don't get it. I thought I was being hired to do stuff like this, then I find out my job is to suck the boss off when he wants, and now I'm back to..." It took two steps for Molly to put herself directly in front of me and to cover my mouth with her hand.

"Are you fucking stupid?" she hissed between clenched teeth. "No, really? I mean it, are you actually fucking stupid?" I tried to shake my head "no". "I don't believe you. You have to be. Shut up, don't say a word." She took her hand from my mouth. "What happens in that office doesn't come out." She was pointing toward the door, and in the general direction of the boss's office. "That's for in there, and in there only. Jesus, what the fuck? You have a good job, it pays well. Me too. Are you really going to fuck that up for the rest of us?" I had no idea what to say. Stammering, I tried to get out an apology.

"I... I didn't think... the door is closed... nobody..."

"Yeah, you got lucky this time. Next time, maybe not. Keep your fucking mouth shut unless his cock is in it. Got it?"

I nodded. "Yeah, got it."

"Good. Now, how do they get filed?" she asked, suddenly calm, sounding like a schoolteacher.

"Case number first, then alphabetically," I recited.

"Exactly. Get to it." Molly turned and started to storm out, opening the door, but then stopped. She turned to look back at me. "By the way, I'm just fucking with you. Everybody knows you're his cockslut." She grinned, waggled her fingers at me to wave goodbye, then left. I stood still, watching the door shut, dumbfounded.

"Fucking bitch..." I muttered.

As I filed (case number first, then alphabetically), I considered what I'd been told. First possibility, and easiest to deal with, was the idea that Molly had just been fucking with me the entire time, getting inside my head because she was... something? Jealous? Just didn't like the new guy? A fucking psycho? I'm not sure. It certainly fit with the way she treated me. I also had a hunch that she was delegating the filing to me. Technically, didn't an executive assistant outrank a secretary? Probably, but her reply would just be that everybody outranks the cockslut.

The other possibility was even worse, though: that the whole company knew. We take up four floors of a downtown high-rise. There's like... 2000 people? I forget. It wasn't possible that they all knew about me, and about what went on in the boss' office. Right? It had to be kept secret, because HR would get involved, and they'd have to put a stop to it, and the boss would get fired and... plus. Why else would he lock the door? Yeah, no, the "the whole company knows" explanation didn't fit. Molly was fucking with me.

Bitch.

So fine, three people knew: the boss, Molly, and myself. I could almost live with that. Well, that and the daily blowjobs, the plug in my ass, the slightly itchy skin when stubble started to grow in, the acrobatics it took to shave everywhere. I mean, there were worse jobs. I could be working in retail.

I had just emptied a box, and was pushing it off the table, when everything went black. Like, not dark, black. Remember, there were no windows, no doors. No light. "Uh... hey..." I said to the room. It was dumb, but I didn't know what to do. "Molly? Are you fucking with me or...?" There was no reply. "Molly? No?" Nothing. Shit. I didn't want to move, because I couldn't see a damned thing, and because I didn't know where all the boxes were, and would have rather not tripped. I raised my voice a little. "Anybody?"

"Cockslut..." He greeted me like a friend he was surprised to bump into; you know, all cheery and stuff.

"Oh, hey there, boss. Um, do you think you could give me a hand? I think Molly is fucking with me and turned the lights off and..."

"No," his voice interrupted. "That was me," he admitted with all the casual coolness in the world.

"Oh..." I said, starting to understand. "Blowjob in the dark?" I asked.

"I'm good for now, but maybe later." His voice was closer now, but I still couldn't see a thing.

"Ah... alright well... how can I help you, boss?" This was going somewhere new, and who knew where that would be?

"I just came to check on you, see how you were doing," he answered casually, as any boss in any company might do.

"With the filing? Not bad. I'm... maybe a little over halfway done? I'm up to the four-hundreds in..."

"No. Not the filing. How are you doing with your plug?" He was right behind me.

Right. Of course. I really needed to come to grips with the fact that most of my interactions with this guy were going to be sexual, in one way or another. He was the one who made me put in the plugs, he was the one who wanted to fuck me in my ass. It was reasonable that he'd be curious how that was going.

"Oh, fine. It's going fine. Still have it in. Don't really take it out much. I've gotten kind of used to having it in there and..."

"Have you moved up to the second plug yet?" the boss interrupted. I hadn't.

"No... still on the first one."

"Hm... you should be on the second one by now, I would think. Are you having trouble with this one?" He almost sounded concerned.

"What? No, no trouble, just, you know, getting used to it."

"I think you're past that point by now, but we should probably find out, don't you think?" I had no idea what he meant. I should have known better.

"Find out? How...?"

"Take your pants off," he said in the tone I had learned to recognize, the one that meant it was time to perform.

"Oh..." I said softly, now getting it. "Yeah, alright." I stood straight and started undoing my belt. It, and my pants, soon hit the floor. There was a hand on my ass almost immediately.

"Underwear too," the boss almost scolded. Right, right, I was supposed to take my underwear off with my pants. "You keep forgetting that. Do I need to take away your underwear privilege?" I hadn't realized that underwear was a privilege.

"N... no, sorry. I'll..." I didn't bother finishing, and simply pushed my boxers off. "OK, done." The hand was back on my ass again.

"Better." He seemed pleased enough. "Lean forward." I did. I didn't have questions. I knew where this was going. There was nothing for me to say.

"Done." The room was totally dark. The boss was just as blind as I was, so I figured I needed to let him know. I felt fingers on my ass again, moving toward the center, moving toward...

I felt the plug sliding out. There was little resistance, because I guess I really had gotten used to it. That was just the starter one. Plus, I still lubed the living fuck out of it. There was a metallic clank to my right, as the plug was set on the table.

"Now..." the boss said, and pushed a finger into my ass. I moaned, in spite of myself god damn it, but it felt good. I hated myself at the time but, fuck, it felt good. With all the lube, and with the new stretchiness of my ass, the finger went in easily, something the boss noticed immediately.

"There was almost no resistance," he commented, wiggling his finger a little. I let out an "mmf". "I think you've... outgrown that plug, don't you, cockslut?" I nodded, then realized he couldn't see me.

"Uh... yeah I guess..." I felt my ass being stretched again, as another finger pushed inside of me.

I gasped, in surprise and sudden discomfort, but not so much pain. "Motherfucker!" I cursed. "Could you warn me next..." I didn't get the rest out. My words were replaced by a low moan. The fingers started moving. He pushed them in, to his knuckles, then back out. I couldn't speak, couldn't react, almost couldn't stand, and was thankful for the table I was leaning on, and that it was dark.

Out of nowhere, another hand slipped between my legs and wrapped around my hardening shaft. I groaned at the touch, at the pressure of his grip as he started stroking me. We were done with words, which was good, because I couldn't find them anyway.

The boss was slow, almost gentle with me. Clearly he didn't want to hurt me, and he really could have. Instead, those two fingers just glided in and out of my ass, while his hand moved along my shaft. At one point I shuddered just from the overstimulation.

I thought about what was to come, about what his cock would feel like, and my ass clenched around him from excitement. Oh... god, I realized I wanted it. In that moment, right then, with his fingers in me and my cock in his hand, I wanted it. I wanted his huge fucking cock inside my ass. I knew it couldn't happen yet, not until I was ready, and I decided that I would definitely train, become ready for it. The thought of it was what finished me off.

I got out an "ungh!" right as my cock exploded. Cum shot from me, splashed all over the floor, while my ass spasmed around the boss' fingers. He, thankfully, stopped trying to finger me and just left them buried inside, as far as he could. I shuddered, I held onto the table, and I came.

It took a while to come down, for my breathing to slow. He was still holding my cock, still had his fingers in me, but neither hand was moving. My ass was still occasionally gripping him.

"I think you're ready for the second plug," he said in the dark.

"Yeah," I almost gasped. "I think so..."

Sudden, blinding light filled the room. I shut my eyes, and felt the boss flinch, though his grip on me stayed firm. Another voice, full of amusement, spoke.

"Hey boss, hey cockslut. How's the filing going?"

~CockSlut

Editor/Story Consultant: A. Burns