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.
