CockSlut Ep. 04

That night, after the filing room incident, I decided to try the next plug. The boss was right; I kind of had been putting it off and was likely ready for it. The second one had felt good, still felt good, but wouldn't get me ready for his enormous member. I could probably have taken a normal dick at that point, but not what the boss was packing, and I didn't know him well enough to judge the extent of his patience. If he became unsatisfied, he could fire me at any time, and nobody would believe my story. Hell, I'm not sure you believe it, but that's a different issue. If what Molly had said was true, that the rest of the company knew that I was the CockSlut, that included HR. If they weren't stepping in now, they definitely wouldn't once I was fired or quit. I had no one on my side.

Of course, that was taking things a bit far. I didn't want to leave. The money was good, and I'd be getting my first paycheck in a week, in the amount of something like eight times what I was making as a waiter, and double what I could earn as an actual executive assistant. So I had to fuck the boss? So what? It wasn't entirely unpleasant.

Standing in the shower, lube in one hand, plug in the other, I began to brace myself. I kept telling myself that it shouldn't be too difficult, that my ass had already been prepared to go to this next step. It might not be entirely comfortable, but it shouldn't hurt. Still, that stainless steel plug looked awfully big. Did my ass even have that much room inside it?

I backed out of the shower spray; the lube was water-based and I didn't want it to all wash down the drain, then smeared the clear goo all over the giant metal bulb. I didn't use the whole tube, but damn it was a good part of it, to the point that I could only hold it by its handle. The last plug was out already, so I gingerly moved this one back and positioned the tip.

I could already feel just how big this thing was, and my stomach knotted, genuinely from nerves, but also with some excitement. The kinky and the "wrong" had always turned me on, and putting a plug in my ass so I could let my boss fuck me with his ginormous cock was certainly both kinky and "wrong". Around the knots, I felt a little flutter in my stomach. The truth was, I liked this.

You know, that's a good point to bring up right now. I've gotten comments, here and other places where I've told this story, where the person feels sorry for me, for my shitty situation, as though I was forced into this. Let me clarify: I was never, am never, forced into anything. I signed on to this job. Yes, under false pretenses, but with compensation. I'm paid stupidly well, my boss is good to me, and it's not like I was ever entirely opposed to the idea of being with a man, I just never had. To put it bluntly, I'm not being raped. I'm good, although I do really, genuinely appreciate the concern.

Anyway, back to the butt plug... (one of those sentences you never think you'll ever write...)

So I was leaned over slightly, plug positioned at my asshole, covered in lube. I pushed gently, bracing myself, but there was no need. Oh, I felt the stretching, the pushing of previously-set limits. There was resistance, some I could help, some I couldn't, but eventually, the largest of the plugs was inside me, safe and secure and snug inside my ass. Only after it was in, and I stood fully back up, did I notice that I was hard as fuck. Maybe it was the excitement, maybe the prostate stimulation, but either way, I had an erection like no other, that couldn't be ignored, so... I didn't ignore it. I'm sure you don't want the details of that...

Oh who am I kidding? You know you do.

I used a little more of the lube and immediately started stroking myself, not bothering to go slowly. Slow was only for when you were starting, to get yourself hard enough to go faster. The plug had already gotten me there.

I like to start at the base and go to the tip, then back down. Some guys start at the head, I dunno, I don't. It's just me. My grip was firm, strokes even, but growing faster by the second. The plug felt so good I just couldn't help myself. With my other hand I cupped my balls, enjoying the hairless smoothness of them and once again deciding that my boss was right about that part. I fondled and I stroked, and I thought of him fucking me.

Yes... yes I fantasized about my boss fucking my ass with his massive cock. I pictured him bending me over his desk and using my ass until he came inside me. I wanted it. I don't know that I was specifically attracted to the man himself, but I definitely was to his cock and balls. The man was an accessory to the genitals, and even in my fantasies (because there were many more) I focussed on them instead of him.

I stroked and fondled and thought until I came in a massive orgasm, cum splattering on the shower wall. I moaned loudly, the sounds echoing off the bathroom tiles, and I was thankful that I was alone that night.

Finally satisfied, I did the normal shower things, and almost wound up with another erection as I washed down there. One was enough though, for now.

The following morning I told my boss, just after his blowjob, that I had put in the last plug. He told me to show him, and I did. It was now only a matter of time...

Another week, actually. It was another week before the boss decided it was time to try. I at first resented, but later appreciated, that he didn't tell me ahead of time. There was no warning, no "hey, show up tomorrow ready to be butt-fucked", nothing. After it happened, I felt like I had been ambushed, even though I knew that it was eventually coming. Later, thinking back on that first time, I came to appreciate the boss' strategy: telling me would only have made me nervous, tense up, uneasy, maybe not even come in. Instead I had no time to anticipate or to work myself up. I just came in one day a week or so later and... well let me just tell you.

It was a Friday, in fact, the Friday of the week after the filing room incident. I'd had the plug in ever since, all the time, and was finally comfortable with it. I could constantly feel it, hanging around, wiggling inside my ass, but it was a comfortable familiarity now, rather than a constant nuisance. Like with the others, I had decided I could get used to having it around, and kind of enjoyed it. I was also starting to take on the mentality of being a cockslut; of being used for my body, of being paid to be a sexual object. You know, I totally get the argument that a situation like mine can be humiliating, degrading. I know women go through it all the time, often unwillingly. That wasn't my case. Like I said before, I was starting to like my job, such as it was. The thought of being some powerful man's cockslut was exciting, and when alone, I admitted to myself that it was a turn-on. The plug was a reminder of what I was, and more often than not, I walked around the office with a chub.

Even after a couple of weeks working for the boss, the morning routine was still the same: I came in and sat in the outer waiting area, across from Molly as she did her best to pretend I wasn't there, waiting for her to tell me it was time to go in, or for the boss to come get me himself. So I sat and waited, I adjusted in my seat, letting the plug press against my insides and remind me that it was there.

"You on the third plug yet?" I looked up to see Molly glaring at me from across her desk. I cleared my throat, buying a second of time. Was she really asking me that out in the open like this? I looked around, to find that nobody was visible.

"Uh... yeah for a week now actually. Um... a little more than a week."

"You used to it?"

"I think so... yeah..."

"Good," she said, turning back to her computer. To this day I don't know if that was her way of letting me know what was coming, or if she just liked to embarrass me. It didn't much matter though, as the boss opened his door only a few seconds after.

"Come on in," was all he said, and I did just that, following behind him and locking the door without being asked.

"How was your evening?" he asked, which was new. Oh, my boss was never unkind to me, but also never really interested in me in a personal kind of way.

"Um... quiet," I said, beginning to undress. "LIttle TV, little dinner, little beer. My roommate works at night so I have the place to myself."

"You have a roommate?" the boss asked as he lowered himself into his chair.

"Oh, yeah definitely." I was undoing the last couple of buttons on my shirt. "Can't afford not to. Rent in this city isn't cheap, and living outside of it, you make up the difference in the commute. The busses don't run far enough so you have to drive or take a taxi or an Uber or something." The boss just looked at me, like I wasn't even speaking English. "Short answer, no, can't afford it yet."

"You can't afford to live on your own, with what you're being paid?" He sounded incredulous.

"Oh, with what I make now, yeah probably. Very probably." I undid my belt buckle and unzipped my pants. "But I would have gotten my first paycheck today. I haven't even checked my bank account to see if it deposited. That first check would have to cover first and last month, security deposit, a small amount of furniture like a bed, various assundries..." My pants and boxers were off, revealing that I was, like usual, partially engorged, though not yet erect.

"Mmm." The boss nodded his understanding of the situation. "You should work on that though. I'd rather if you lived alone." I thought that was curious, and so I asked about it. "You're in a very sensitive position, I think we can both agree on that. There are certain lifestyle changes I've asked you to make that can become more obvious if you're living with someone. The constant shaving, for one. You have to hide things like your plugs. At least I hope you hide them. There may be more, and having a place to yourself makes that much easier."

Huh. That was a good point. For the moment, I was lucky in that I didn't see much of my roommate, but if he didn't work nights, if he ever saw me walking funny because I'd just put in a larger plug, or happened to notice some stray hair in the shower, he might have questions. "Alright, I'll work on that," I agreed, shoes and socks now off, so that I stood totally nude. "As soon as I can. But what are we doing today? Blowjob as usual?"

The boss pushed back from his desk and stood, a sign that we were about to get down to business. "Yes," he said, then began undoing his tie. I raised an eyebrow: the boss had only stripped nude once: that first time. After that, he always just had me pull his cock from his pants, or he did it for me, and that was it. I didn't think much of it, or didn't put as much significance into it as it actually held, and decided to just go with the flow.

As he undressed, I stepped around the desk, kneeling, and undoing his belt. I pulled his pants and boxers down, then helped him step out of them. Even his shoes and socks came off, so that he was just as naked as I was. When all was done, there I knelt, face-to-face with the huge, beautiful cock I'd been sucking for the past three weeks.

I really had become attracted to it, I'm not going to lie. My boss has a gorgeous cock, there's no other way to really put it. Even when flaccid, its size is impressive, and you can tell that it will only become more so as it grows. The tip hangs just below his testicles as it curves over the sack. His balls usually hang low, unless he's excited, at which point they tighten up, pulling closer to his body. This is all surrounded by smooth, hairless, lightly tanned skin. Still, it's nothing when compared to him erect.

I began with a gentle and polite kiss to his head, followed by a slow lick up the soft shaft and even up a little farther along his pelvis, then dragged my lips back down, over the shaft and the head, and under, to kiss and then lick each ball separately. I decided to continue there until he was hard, so I pulled one into my mouth and began sucking, without much force, and rolling my tongue over it, making soft, slurping sounds as I went. I could feel his cock starting to rise against my cheek, so I moved to the other testicle, wanting to give them both a fair amount of attention before moving on. I used my tongue and my lips, sucking, licking, caressing him with my mouth, until I could feel that he was mostly hard.

I sat back and admired my work: his massive dick was hard, mostly erect. The shaft was no longer smooth, instead sporting a thick vein that meandered along the length. The head, which would eventually turn a light purplish color, was for the moment still its normal skin tone, but it was aimed directly at me, at my lips, as if giving directions. I wanted to lick it, to kiss and suck it, and so I did.

I leaned in, taking the shaft in my hand, and started to kiss and nibble just at the base, to the side and under a little, lifting the big cock out of the way. I could never get the whole thing down my throat, not then anyway, and so this was the only way to give the base any oral attention. The boss always seemed to appreciate it.

I licked back up to the tip, slowly, my tongue flat and wide to cover as much as I could. I sucked the head for a moment, then slid down the other side of his shaft, to the bottom, where again I licked and kissed and nibbled at the base. He was fully hard by then, and it was time to stop playing. Backing up to the head again, I took him into my mouth, head, and a couple inches beyond, then sucked hard as I slowly backed up, letting the end pop out of my mouth. Again I sucked him down, opening my jaw wide, trying to fit more but unable. My gag reflex wasn't kicking in, but my throat just couldn't physically expand enough. I still couldn't force it to relax and accept the visitor. I made up for it with my hand, stroking what I couldn't suck, sucking as much as I could. I bobbed my head up and down on his shaft, humming a little as I went. I was really starting to get into it.

"OK, alright, stop." At first I didn't think I heard the words, then decided I didn't hear them correctly, until the boss gently pushed me back and off of him. I looked up, confused. Was I doing it wrong? Did he not have time? Did he want something else? "Stand up." I stood. We were both hard, and our cocks bumped against each other. "Bend over the desk."

Oh my god. This was it. This, here, now, on his desk, just like I'd pictured it. I was about to be fucked in the ass. My boss was about to bend me over and fuck me in my ass. I was going to lose my anal virginity. I was going to have a cock inside my ass for the very first time. I almost came right then.

"OK, yeah, sure boss..." was all I said before stepping past him, casually brushing my fingers over his cock as I went. I stood where his chair normally would have been, on his side of the desk, facing the office door. I only then noticed that most of his desktop stuff was missing or had been moved to the side. So this had been planned.

Placing my hands on the smooth wooden surface, I leaned forward, not all the way over yet, steeling myself for what was to come. I shook my head in disbelief, then bent all the way forward, arms crossed under my head.

I could feel him moving in behind me, even before he touched me. The air shifted, or the light from the window changed. Fingers caressed my ass, in circles, up and down. They slid between my cheeks, over and around the metal handle of the plug, examining, I figured. They slid underneath me, behind my balls, touching, feeling my smooth skin, then down the bottom of my shaft.

"This excites you," he said softly as his hand wrapped around my cock.

"Y... yes..." I admitted.

"Tell me," he instructed, slowly stroking me.

"W... what? Tell you what?"

"Tell me why it excites you, my cockslut," he explained.

"B... because... because it's wrong. It's kinky and it's wrong and it's also ... right..."

"Mm... yes," he agreed, "but... why else?" I thought I knew what he was getting at.

"Because I love your cock..." I said, eyes clenched shut with delightful humiliation.

"You do? Oh good, I'm very glad to know that, CockSlut. But so far, you've only sucked my cock, and played with it with your hand. That doesn't sound like you love it." His voice mocked my lack of experience as his hand slid up and down my shaft.

"I... I just wasn't ready, but I wanted it, I want it now..."

"Want... what?"

"You... your cock... I want you to fuck me in my ass with your enormous cock..." I was almost pleading by now.

His hand left my own erection, and a second later, I felt the plug slowly being pulled from me, until it left my body entirely, and was placed on the desk with a familiar clunk. His hands were on my ass, spreading my cheeks as he examined. "You've done fairly well," he admired. "Shall we see... if it fits?" I nodded, eyes still clamped shut. Then... I felt him. I felt it. His cock was pressed up against my ass, the head positioned to push inside.

I heard something then, a kind of squirting sound, and couldn't figure it out until I felt the cold goo drop onto my ass. He was lubing himself, and me, and I was both thankful for his care, and annoyed by the further delay. I just... wanted him in me already. I heard the lube snap shut, then the rustle of a paper towel. Finally, his hands were back on me, on my hips this time, firmly holding me in place. It was the first time he'd in any way shown me his strength, and something about it, about knowing that this man was bigger, stronger, more powerful than me, was exhilarating.

Just after his hands touched me, I felt the head of his cock poking at my backside. It slid between my cheeks easily, and a second was pressing against my asshole. I was already stretched and still open from the plug, and yet, he didn't immediately just pop into me. I could feel him pressing, pushing himself forward. My ass started to hurt a little, as it refused to allow entry. At one point, one of his hands came off me. I assume it went to his cock to help push, because the pressure on my ass became greater, but still, he was denied entry.

"CockSlut," he addressed me like a naughty child. "You can tell this isn't working. Why aren't you letting me in?"

"I want you in, boss. I really, really do. I don't know why it isn't working. I wore the plug all week, you saw. You should fit."

"I saw, I should, you're right. Except now your ass is clenching down too much. You're stretched enough, but you're closing up."

"I don't mean to be... I'm sorry boss..."

"It's OK," he said, reassuringly, patting my butt. "Really it is, but we do need to do something about this." I nodded, pushing myself up, understanding that this attempt was done for now.

"What do we do?"

He didn't answer me, not directly anyway. Instead, he pushed a button on his phone. "Molly, come in here please." I grimaced. Not her... no not her... But it was her. She must have a key to the office (makes sense, she's the secretary) because she came in even with the door locked. Taking a look at both of us, each naked, hard, and clearly frustrated, she crossed the room.

"What's up, boss?" Molly asked, as if the scene were nothing out of the ordinary.

The boss didn't directly answer her either, and instead opened a bottom desk drawer, from which he removed a massive, realistic dildo, complete with moulded balls. Using the dick as a handle, he stuck the suction cup on the back to the top of his desk.

"Here," he said, turning to me. "That's pretty much the right shape and size. You're going to take this home, and you're going to practice. You'll get used to having a cock in your ass, not just a plug."

"That..." I pointed toward the rubber toy, "is going to make me not hesitate or close up?"

"No," the boss conceded, "that by itself won't. It's not bigger than the plug, which you took without a problem. Your issue isn't the object going in you, it's the fact that there's another person involved." I looked up at him then, suddenly afraid of where this was going. "Molly, you're going to help. Buy a harness that will fit this dildo, you can take the money from petty cash, and teach my CockSlut to take it in his ass."