CockSlut S02E01

First, let me recap:

I was tired of working my dead-end job, making next to nothing, always wondering if the next rent payment was going to get made. I answered an ad for an executive assistant, but quickly learned that the job wasn’t quite what I expected. I became my boss’ CockSlut. I was his personal sexual assistant, which was immediately a challenge, not because I wasn’t into other men, but because he was just so… big.

My boss has the largest cock I’ve ever seen, in person, or in porn. No joke. It’s enormous, and it took a long time to get used to it. I was motivated, though, both because I wanted the job (the paychecks were really good) and because damn it, I really liked that cock. Like that cock. I still do.

Eventually, with time and with some help from Molly, his secretary, I was able to take him most of the way down my throat, and in my ass. Sex with my boss became a regular thing, usually in his office, though not always.

I was also used as a kind of relationship-builder during important business meetings. My first time was with a nice guy named George. I liked him, and it was nice to be on the giving end for a change. Usually the dick went in me. Even with Molly.

She’s another story. Originally a complete bitch, Molly seemed to resent me. Of course, the boss had other ideas, and decided that she would help train me to take his cock. He gave us, or really her, what had to be an exact silicone replica of his own member, which she used on me regularly. Technically, she was the first person to successfully fuck my ass. I wasn’t allowed to fuck her.

It was on that business trip, the one with George, when I finally understood Molly’s issue with me: she was the first, the OG CockSlut, rejected by the boss probably because she was a woman. He’d allowed her to stay, to keep her rather extravagant salary, and continued the search for his perfect, male, CockSlut.

*****

I’m required to tell you, by the way, that during the break between the previous entry and this one, my boss learned that I was posting these stories here. He waited until I was going down on him to tell me he knew, then insisted that I keep blowing him while he read them. We went through one a day, each time with me under his desk, on my knees, his cock in my mouth. Actually we went through them a few times, even doing another one today. As I’m writing, I can still taste his cum in my mouth…

He also made me tell Molly, and honestly, I think it was just to see what sadistic little punishment she would come up with. By now, of course, he knows all about that… relationship… So now I’m sitting at my desk, nude except for a pair of her panties, which don’t really fit. Either my cock or my balls wind up slipping out, but those are the rules: every time I write one of these, especially if it involves her, I have to do it in her underwear. There are… worse things, I guess. Actually… it’s not that bad.

Anyway, alright. Season 2, Episode 1. Here we go.

*****

Molly didn’t say anything for several moments. Her eyes left mine, shifting down, then away as she leaned back against the headboard. Her look confirmed my suspicion though: she was the first CockSlut, the first person hired to sexually service our boss, and the only woman. Why had that failed? Was the boss gay, especially since the other three in the position were men? Was Molly just… not good at it? I seriously doubted that. I also didn’t want to ask what happened, since the whole subject was clearly bothering her. She was the one to finally break the silence.

“Three years ago,” she started, still looking straight ahead. “I replied to an ad for an executive assistant. I thought it was odd at first because it didn’t list any qualifications really, no degree, no experience. I knew I was qualified though. There were plenty of postings for the same kind of job and I met all of those requirements so… yeah, I applied. You probably know how the interview went…” I did. In fact, I’m sure that much of what happened to me on that first day also happened to her.

“I was good. I was damned good,” she insisted. “You know, I could almost take him all the way down my throat on that first day? Just a talent I have, apparently. And we had normal sex, plenty of it, but he always wanted my ass. From day one, he told me that he was going to fuck my ass. Even gave me toys to help prepare me.” I squirmed very slightly, suddenly feeling the plug I always kept in my own ass. “I got there, too, faster than you did. He was so happy that first day, me bent over his desk while he fucked me there. I… I won’t lie, I liked it. Hell, I loved it. I loved feeling… desired, and even used a little.” I nodded here, understanding exactly what she meant. “Every day he’d have me go down on him, then fuck me both ways, although eventually there was more butt sex than anything.”

Molly sighed, stopped for a minute, took a few deep breaths. “It lasted five months. He never had me take care of clients, but he and I would fuck every day, and not just at the office. Sometimes he had me go home with him. He lives alone, not married, so it wasn’t difficult or awkward. I’d stay the night then he’d drive me into work. It was nice, but never became, you know, romantic or anything. It was a job and we both knew that. But I liked… I loved… the attention. Then one day it just stopped. He stopped asking me to come in and strip, stopped inviting me home, stopped fucking me. He eventually said that he wouldn’t need those ‘services’ from me anymore. Can you fucking believe that?” Anger was now creeping into her voice, anger and hurt. “Those ‘services’, like I was his whore or something. He told me I could stay, that he’d find me a position and make sure my pay didn’t change, and fuck… I needed the money and the stability. I swallowed every bit of my pride and became his fucking secretary. A couple weeks later he asks me to put an ad online for a new executive assistant.”

She wasn’t crying, but was only barely holding it together. Molly felt something for the boss, probably not love, but some kind of need for his approval or acceptance. His rejection must have hurt deeply, and the search for a new CockSlut just twisted the knife.

“I hated the other two, hated them, partly because they took my position, and partly because they were men. The boss wanted something that I never could have given him, but he hired me anyway, set me up for failure, just because he couldn’t admit that he wanted a man instead. I wanted to hate you too, and I did for a little bit. I wanted to sabotage you, to make you want to quit, and when the boss told me to help train you, oh, at first I thought it was wonderful because I could absolutely humiliate you. But… you weren’t humiliated, and then you turned out to be a good guy, and…” Molly’s eyes turned up to mine again, for the first time in several minutes, and a tiny smile tugged at the corners of her mouth.

“Don’t get the wrong idea, CockSlut. I’m not coming on to you. I’m not about to profess my love for your or anything. I don’t know that I even like you at all, but I also don’t hate you, OK?” The look she gave me said something a little different, that in fact she might like me, at least a little bit. “You’re an alright fuck, so there’s that. And you let me do what I want with you, which is a plus. Don’t think that this is going to turn into anything though. We’re not going to start dating or whatever. This isn’t some oddball romance. Maybe… maybe… we’ll eventually be… maybe friends but… no guarantees. For now we’re fuck buddies and that’s it.” I nodded my understanding. “We’re still going to do it like we have been, as in, me fucking you in your ass. But we might throw in some more normal sex too, just… because.”

“That… would be nice…” I agreed, thinking of how it felt to have her on my lap, riding me. “Do I get to fuck your ass then?” I quipped, figuring she’d chuckle then turn me down.

“Probably,” she answered after a second’s thought. I arched an eyebrow. “What? You already know I like it so…” We shrugged together, and that got another almost-smile.

“I’m going to sleep,” Molly declared after a few minutes of comfortable silence. “No cuddling, OK? This isn’t that.” I nodded and, as I lay down, turned away from her. Somewhere in the middle of the night I woke to find her body pressed against mine.

*****

When I came out of the shower the next morning, Molly was gone. Checking the clock, I decided that she was most likely back in a meeting with the boss and the client, George, and I again had nothing to do until someone gave me something. As it turned out, I wasn’t going to be needed for the rest of the trip.

The following day we headed home. The meetings with George had been productive, even successful, partly thanks to me, the boss said. I won’t lie; I was a little proud of that. There’s something about taking pride in a job well done, even if that job was to fuck some guy and let him suck you off. This was, honestly, the first job I was at all good at.

Molly wasn’t speaking to me, hadn’t said a word to me since that night in bed. I won’t say that she ignored me, exactly. She seemed to acknowledge my presence, even apologized for stepping on my foot as she tried to get past me to use the plane’s restroom, but otherwise we didn’t talk.

I used the time to think, to look back on the past few months, trying to really put things into perspective, and to understand what was going on, and what it meant for and about me. Of course I asked myself if I was gay. Obviously I must be, at least to a degree. I had never actually been with a man before the boss, had never given head or jerked a man off, had never been fucked in my ass. I’ll admit that, sometimes when watching porn, I looked at the male actor more. I could appreciate the nude male form, I guess. Some men were attractive, and I understood that there were things I liked and didn’t like. Of course, any hemming and hawing about my possible attraction to men was now moot, given that I was in a regular sexual arrangement with one.

Of course, I was in a regular sexual arrangement with a woman too, or at least, so it seemed. I still didn’t really know what was going on with Molly, where that was headed, if anywhere. I knew I was attracted to her, from a physical standpoint at least. She had made it clear that there would be no romance between us and I was fine with that. Sex only. Fuckbuddies. That worked for me.

It was late afternoon when our plane landed, and early evening by the time we left the airport, each in our separate taxis. By that time all I wanted was food, a hot shower, and an evening in my underwear in front of the TV. I wanted to release myself from the world, at least until the next morning. I showered and shaved, I ordered takeout, and I watched a House M.D. marathon in my boxers. All in all, it wasn’t a bad night.

“Hey boss,” I said cheerfully, shutting and locking the office door.

“CockSlut,” the boss said by way of greeting. I was reaching for my belt when he stopped me. “Not yet, keep it all on for now,” he instructed, holding up a hand.

“Oh? We going somewhere?” I asked, reseating the leather.

“No, but someone is coming here. We have a meeting in a half hour.” He gestured with the back of a pen toward the seating area to the side of his office.

“Oh, alright. For now I should…”

“Sit and look pretty,” he said, looking back down toward his papers. I did just that.

Not long after, our visitors arrived. I was introduced to Ted, a higher-up in another company we dealt with, although as more of a peer relationship, rather than as a client. Ted was around my boss’ age, with just a touch of gray showing at his temples. He was in good shape from what I could see, though much was hidden. I had started discovering that I was checking men out nearly as much as I did women, now that they were options as sexual partners. I figured I’d probably wind up fucking Ted, or vice-versa, or at least sucking his dick or something.

Ted brought Mark along with him, and introduced him as his own executive assistant, which caught my attention. Was Mark also a CockSlut, or whatever term his boss used? He fit the part, which was to say he was young, attractive, built well. There were no other clues, though, and the meeting pretty much got right to business after the introductions.

To be honest the meeting is kind of a blur. I didn’t understand a lot of it, and wasn’t asked to do anything, so I sat, like the piece of eye candy I was. I did catch a couple of sideways glances from Ted, and maybe one or two from Mark as well. My boss, on the other hand, had no reservations in letting his eyes slide all over Mark, and I wasn’t sure if that was just because he liked men, or if there was something else going on.

“Well, I think that’s as far as we need to go for today,” Ted was saying, wrapping things up. Nobody moved, though, other than a quick nod from my boss. Ted was suddenly grinning, and his whole body seemed to relax. “I brought you a present,” he said. “I know there’s been some issues, so I thought I’d bring Mark along for you.”

Well there it was. Mark was a CockSlut. I wanted time to process that, to work with the idea that I was not unique, that maybe my profession was far, far more common than I thought. It was the oldest one, right?

As if taking a cue, Mark stood and began to undress. Shirt, tie, pants, shoes, socks, they were all removed quickly. Rather than boxers or briefs, Mark wore a green pair of bikini briefs which snugly held his package. The outline of his cock was clearly visible.

“I like those,” my boss said, gesturing to Mark’s underwear. “You should get some,” he said, turning to me. I nodded in… understanding or agreement, I wasn’t sure.

Mark slid the underwear down and off, then stood, presenting his nude body for us. He was certainly fit, with defined musculature, a tight stomach, strong legs, and almost-chiseled chest. His cock hung to the side a little, decently-sized, in front of a very attractive set of balls. I can’t really explain what makes balls attractive. Honestly they look kind of weird, but Mark’s were nice.

My boss stood, as did Ted, and both began to strip. I figured I was expected to join the party, and did so as well. Mark watched, eyes mostly on my boss, and then mostly on his pelvis. He was waiting, anticipating. He either knew firsthand, or had been told and wanted to see for himself. His eyes widened just slightly, but he openly grinned at the sight of my boss’ massive cock. He wasn’t hard yet, and already he was a little bigger than my own. Honestly, if scenes like this one were common among powerful men, I was certain my boss had to be a legend.

Once we were all in our birthday suits, Mark took a step toward my boss, hand slightly extended forward. “May I?” he asked, eyes still on the prize. The boss nodded, and Mark gently touched just his fingertips to the shaft. It twitched, but Mark only pressed more, sliding his fingers around. “They told me… but I had no idea…” he said, a little breathy.

Ted moved to the side a little, probably to get a better view, then took a seat on the couch. He waved me over, and I sat next to him, thighs touching. “Impressive, isn’t it?” I asked.

Ted nodded. “I understand you still can’t take it all.” It was more just a comment, without any real meaning, although I felt a little pang of failure.

“Not yet,” I confirmed, “not all the way down. I can in my ass, but I can’t suck down every inch yet. Still learning.”

“I heard. That’s why I brought Mark. Champion cocksucker, that one.” He seemed pretty proud of his own CockSlut. “Although, I haven’t tried you yet, so…”

For the first time I turned a little more toward Ted. “Oh, did you want me to…?” I stopped. That was a stupid question. “Right.” I repositioned myself, moving back, then kneeling on the couch. I got a good look at Ted, and wasn’t disappointed. Again he was older than me, my boss’ age give or take, so early forties. He was in shape, and probably used the same gym as my boss. His cock was average, cut, still not hard yet, although he was gaining a chub. He didn’t shave, not like my boss and I did, but had trimmed well, which I appreciated.

Ted leaned back into the couch and spread his legs. I took another look at Mark and my boss, watching the other CockSlut stroking him to erection, up and down the long, thick length. I started to do the same to Ted, slipping my fingers around his shaft, lifting him up, gently pulling and stroking. He groaned a little.

When he was mostly hard, I leaned forward and gently licked the tip, before opening my lips and lightly sucking the head. It twitched in my hand, and I took a little more, maybe another inch past the glans. I swirled my tongue over and around him, and felt him harden even more. It stood up enough that I no longer needed to hold the shaft, and instead switched hands, supporting myself with one, cupping his balls with the other. Before he could complain about my hand being removed, I slid down the entire length of the shaft, taking every single inch of him.

Ted groaned loudly this time, as I carefully rolled his balls and started to suck. I didn’t let any of him out of my mouth, instead holding him tightly with suction, until I finally started to slide back up. I let him pop out, letting him feel the cool air against his wet cock, then took him again into the warmth of my mouth, rolling my tongue as I went all the way down again. Keeping him in, I bobbed my head up and down, still slowly, not wanting to finish him off too soon. I felt his hand on the back of my head, not pushing, just… kind of a sign of appreciation I guess. I hummed a little as I slid up and down, the vibrations tingling his cock.

After a minute I let my eyes slide over to the other two. My boss was still standing, but Mark was on his knees, his hand wrapped around the base of his cock while he kissed and nibbled it from the side. For a moment, I inwardly grinned, figuring that even Magnificent Mark was stalled by the sheer size of the cock he was trying to pleasure. That inward grin dropped instantly as he removed his hand and, without hesitation or difficulty, sank all the fucking way down my boss’ cock. His nose pressed against my boss’ pelvis, bottom lip against the top of his scrotum. The fucker even managed to slip his tongue out and slide it over the balls. I growled in jealousy, in envy, in desire to be able to do the exact same thing. It wasn’t even a matter of my job anymore; I wanted to do it for him, and for me. That was my cock that this other guy was sucking, and doing a better job of it. I wasn’t jealous. I didn’t care if my boss fucked other men or got blown by them, but damn it, that cock belonged to me and I should be the one who sucked and fucked it the best.

A grunt from above brought me back to my side of the room, where I realized that I had stopped moving on Ted. In apology, I sucked hard, again taking the entire shaft, feeling the head press against the back of my throat. A moan confirmed I was forgiven, and shortly after, I felt the balls in my hand tighten. Ted erupted in my mouth, a handful of quick spurts that I immediately swallowed. A few seconds later and he was starting to go soft.

I sat up, then back, licking my lips, more for show than out of necessity. Ted was grinning, eyes shut, head leaned back against the couch. “Pretty good,” he praised, patting my thigh. “You’re not bad at all. I see why he likes you.” Ok, I smiled at that. “I’m done though, for a while. Why don’t you join in over there?” He gestured toward where Mark was still swallowing my boss’ giant cock. “Mark can take care of your boss… you take care of Mark,” he suggested.

The logistics of three men enjoying two blowjobs was a little complicated. We wound up with my boss sitting at one end of the long couch, with Mark knelt on the couch next to him, on all fours, and me on my back, under Mark. I could only hear what was going on above my head, and so tried to not think too much about it, paying most of my attention to Mark’s dick. By now he was hard and, to be honest, his cock was beautiful. Smooth in the right places, perfectly-shaped head, very slight upward curve, and a single thick vein running down the side that was fun to run my tongue over. In this position, Mark was the one who had to do the moving, mostly, and every time he pushed into my mouth, his heavy balls rested on my chin.

After a little bit, I felt him pull up and out of my mouth. I looked up, confused, and saw that he and my boss were changing positions. Mark spun around and again straddled my head. I thought I knew what was happening, and my suspicions were confirmed when he leaned forward and took my own cock. We each could easily take the other fully, and did, while I watched my boss approaching Mark from behind, holding his enormous member.

The groan against my pelvis when Mark was entered sent vibrations through me. There was an undefined kind of grunt once he was fully impaled, and then the gentle smacking sounds of flesh impacting flesh.

Sex is funny, and if you can’t laugh at sex, you’re doing it wrong. One of the most vivid memories I have of this encounter was my boss’ balls bumping me on top of my head with each thrust. I told him about it later and we had a good chuckle.

Mark was going to town on my dick, sliding up and down, licking, rolling his tongue, sucking hard. I was trying to do the same for him, though his hips were mostly still in the up and down direction, so I had to do most of the work. I sucked, I licked, I even nibbled, and I rolled my tongue up and down that fun vein, until I heard the telltale sounds coming from my boss. I had learned the noises he made when he was about to cum, knew them intimately, and could probably have set a watch based on the time from the start of the noises until the first spurt of cum.

I knew that, at that moment, the giant dick was throbbing in Mark’s ass, pulsating, stimulating. Between that and my mouth, Mark didn’t have a chance. He came just before my boss did, just before I did, and I took the second load of cum, from as many sources, of the day. Of course I swallowed, and damn it, I had to admit that I liked Mark’s cum. As much as I wanted to hate him, to loathe him for being better at this than I was… his cum was nice.

At the same time, my boss and I were shooting our own loads into him, at either end. Like a champ, he took them both, not spilling a drop from either of us. My boss pulled out first, and I heard the heavy, wet sound of his cock slapping against his thigh. Mark waited a minute, and before getting up, placed a light kiss just next to the base of my shaft. I tried to give him a “what was that for?” look, but he never turned his eyes directly back to me.

Mark went to clean up, while the rest of us just used some wipes that we kept around for such things. A little while later we were all dressed and shaking hands, as if nothing had happened other than a totally normal meeting. Ted and Mark left, and it was just the boss and me again.

I sort of flopped on the couch, while he went back to his desk. “Well that was nice,” he said jovially.

“I bet,” I replied, letting just a little bit of the bitterness leak out. He looked over to me.

“What?” he asked.

“Oh. Nothing,” I said, trying to sound casual and not making it.

“Don’t be a passive-aggressive bitch. Tell me what’s wrong.”

Well. I had never been called that before, neither thing actually. “I just…”

“Are you jealous? Seriously, CockSlut, are you actually jealous of that guy? What was his name? Matt?”

“Mark,” I corrected. He shook his head.

“See? I don’t even remember his name.”

“No, but you remember that he could swallow your whole cock,” I returned. He didn’t say anything for a moment, just looking me over. His voice was suddenly… a little softer when he replied.

“Look. Yes, he took my whole cock. He’s also supposedly a prissy little bitch who makes Ted buy him presents all the time. Did you notice his watch?” I hadn’t even noticed that Mark was wearing a watch. “Rolex. Seriously, a fucking Rolex. I don’t even have one of those. Wouldn’t want one. All you’re getting is the name, but that’s beside the point. That guy wants to be pampered. He wants to be some kind of little prince or something, kept in a high tower and to come down, when he pleases, to ask for something and to suck a dick to get it. You? You’re not like that. You’re a guy who sucks my dick and lets me fuck him, and I pay you a decent salary, more than decent, and that’s that.”

I let that hang in the air for a minute. So that was what he liked in me? That there was no bullshit? That we had our simple deal, we both kept to it, and it wasn’t complicated?

“If you’re worried about the dick thing, I mean, you’re getting there, right? You and Molly are practicing?”

I nodded. “Yeah. The uh… dildo you gave her is surprisingly close to your own, so it’s good to practice with.”

“It should be,” he said, suddenly grinning, “it’s a mold of mine.”

I chuckled, tension suddenly dissipating. “You molded your cock to make a dildo so I could practice with it?”

He was visibly more relaxed as well. “Something like that. But look. Yeah, that guy gives really good head, but so do you. And you’ll get to the point where you can take it all. I’m not in a hurry though, alright?”

I nodded, feeling suddenly secure in my position, and in my cock-sucking abilities. I mean, I had come a long way, right? From having never sucked one before, to now being able to take nearly all of the largest real one I’d ever seen. I smirked, then stood. “Alright, I’m going to go get lunch. Thinking about that sandwich place down the street. You want anything?”

“I’m good for now, thanks,” the boss said, before looking back down to his paperwork. “Maybe check with Molly though.”

“Yeah, good idea,” I said hesitantly, before leaving. Molly… was a whole other can of worms that I didn’t care to open at the moment. We’ll get into that another time though.

~CockSlut

Editor/Story Consultant/All-Around Badass: A. Burns

Source: reddit.com/r/Erotica/comments/lgdo0g/cockslut_s02e01