CockSlut Ep. 05

That same day...

After having failed to relax enough to let my boss fuck me in the ass for the first time, and then being dismissed from his office, I figured it was time to catch up on my actual job, whatever that was, exactly. The thing is, my role outside of sucking and fucking the boss wasn't really well-defined. Despite the lofty title ("executive assistant"), my role really was little more than office bitch-boy, running errands here and there, copying, filing, faxing. Molly usually had things for me to do, which at least could keep me busy on a slow day, or on one where my ass failed to cooperate. So I took my list of chores and went, trying to avoid her, the boss, that whole part of the building as much as I possibly could.

Molly's list was fairly comprehensive, and was taking me to floors that I didn't realize the company even owned. Come to think of it, I don't think they were all ours. Still, I went, because I had nothing better to do, or at least, nothing I could do while there. Everywhere, I watched people, watched them watching me. Did they know who I was? What I was? Had Molly been telling the truth when she said that everybody knew there was a new CockSlut in town and I was it? I thought I caught a smirk once or twice, maybe a head nodded in my direction, not to me, but about me. "That's him, yeah that one over there." I could prove nothing, not even to myself, but I felt it. I felt the eyes on me.

Eventually, errands finally run, I made my way back toward the boss' office. It was the end of the day: time to pack up and get the hell out. I needed to collect the practice dildo and figure out with Molly when... how... what the details were on the order for her to "help" me with it.

"Hey so..." I said, standing close to her desk, leaning over some so as not to be overheard. "Where's... you know... the thing? So I can take it home?" Molly's eyes flicked up to mine, and she smiled sweetly.

"Oh, it's in my backpack. Don't worry."

Don't worry? "Um... I'm supposed to take that home and..."

"No," Molly cut me off. "No, I'm supposed to use it to train that ass of yours." She made little effort to keep her voice down.

"Hey!" I whisper-shushed her. "Could we keep it down about that?" She just grinned.

"I told you, everyone already knows. So, are you ready to go?"

"Go? Where?"

"Well, it's the end of the day, isn't it? Unless you want to do it here. I guess we could but the office would be locked so... it would have to be on that couch over there." She gestured behind me and I turned, looking at the uncomfortable couch that the boss made people he didn't like use when they were waiting for him.

"N... no, that's fine," I agreed, turning back to Molly. She had a key to the office, I was pretty sure, but wasn't about to argue the point. "So where are we going then?"

Molly stood then, a big smile on her face. "You actually get to come to my place," she explained, uncharacteristically cheerful, and as if all I had ever wanted. "You certainly can't expect me to go to that shithole you call an apartment."

"Hey now wait a minute!" I protested. "Look, it's what I can afford and it's not that bad and... besides... how do you know anything at all about where I live?"

"I don't," she said, stuffing a file into a bag, "I just assumed, and then you confirmed." I was dumbstruck for a moment. "So until you move somewhere nicer, any... extracurricular activities like this will happen at my place. Got it?" I was too embarrassed to do anything other than nod.

Unlike my poor, plebeian self, Molly drove her own car; a nice one, in fact. It couldn't have been more than a year old, and with every bell and whistle that model could have come with. She drove confidently, weaving us through traffic as if stop signs and red lights were suggestions, and seeming to obey them at her own pleasure. We passed through downtown, then into one of the seedier parts of town, near the warehouse district. Surely there must have been nicer places we could have gone, but I assumed she wanted absolute anonymity, and couldn't decide if that was because she didn't want to be seen in a sex shop, or with her boss' cockslut.

On the outside, the place was kind of a dump: an old mexican restaurant, windows now boarded up, parking lot mostly empty and lit here and there with bright sodium lights. A police car sat in a space, and I wondered if the officer was a guard, or a customer.

Inside, however, was an entirely other story. The place was brightly lit, and impeccably clean. Shelves were arranged neatly, while pleasant but unobtrusive music played quietly. I had never been in a sex shop, hadn't known what to expect, but was pleasantly surprised.

"This way," Molly instructed, moving off in a direction, as though she knew just where she was going. Perhaps she did. I shrugged and followed, until we stood before a wall covered in various leather, rope, and nylon contraptions. She was scanning, arms crossed beneath her breasts, scrutinizing. I had no idea if she was looking for style or fit or what, but could tell that she was looking for a harness, as the boss had instructed. A harness that would fit the dildo he'd given her. A harness with which she would fuck me. Tonight.

"Um... you know... I uh..." I'm not sure what I was going to say, some kind of protest. The nerves were starting to kick in.

"Shut up, I'm looking," she hissed under her breath. "Stop acting like a nervous asshole and just stand there quietly."

"But... my asshole is nervous," I insisted, and I swear to god, she actually smirked at that. Queen Ice Bitch herself found what I'd said... amusing, at least. She still didn't say anything, though, and continued looking, until she found what she wanted. "There, that one," Molly said, pointing. She had picked a classic black leather harness, without many bells or whistles. It could adjust at the waist and thighs, and came with a couple different-sized metal rings, for holding the back of toys. Leaning in, she flipped the price tag over, and gave a little shrug.

"Yeah this will work," Molly confirmed with a nod. "Now we just need a dildo."

I pointed toward her purse, where the massive toy from earlier still hid. "We have one, don't we?"

"Obviously," she said with an eye roll. "But part of the problem is the size. You can take one that big, but you get nervous and start to close up. You need something smaller for now that I can get in you even if you start to clench shut. Then once you're used to that, we can move up to the right size." She wasn't bothering to lower her voice, and I looked around nervously, wondering just who might have heard.

"OK, OK," I whispered, just trying to shush her. "Fine, whatever you say. Let's just get the smaller one and get out of here."

"You're damned right whatever I say," she replied, indignantly. "Come, let's find something your ass can take."

A few aisles over, a plethora of rubber toys were on display: large, small, realistic, fantastical, motorized, stationary, and in every color imaginable. Molly, with me in tow, headed straight for the realistic rubber dildos, ones with a back that would be compatible with the harness. They all had molded balls attached, which only added to the realism. Honestly, that didn't bother me at all. Hell, I'd already had the real deal in my mouth, so why should a toy that looked like it be a problem? She found one a good size or so smaller than the other, and our boss' real one. It was still large, but not quite the monster in his pants. Molly actually held it up for me, to get my approval. I was a little touched at that, and nodded. It would work. I could tell just by sight that I'd be able to take it.

With the harness, dildo, and a large bottle of lube in hand, we made our way to the register. The clerk, a thirty-something stoner who was one fat blunt from completely short-circuiting his mind, eyed our items, then me, then Molly. One of his eyebrows raised, before he gave an approving nod. What the hell did he care what kinky shit we were about to do? He was getting paid, so no bother for him, right?

Molly, for her part, was all business. The clerk gave a total, she nodded, handed over a card, signed her name, and the transaction was done. Our stuff was loaded into a black plastic bag, and that was it. The clerk gave us a general "have a good evening" that could have carried more meaning than it seemed to, but might not have.

We were silent during the drive to her place. Molly lived on the other side of downtown, in the "nice-but-not-mega-nice" part of town. There was a parking garage though, and she had a designated space. The garage was connected directly to the apartment building, and she led the way. I carried the bag.

The apartment was nice, even a little big for someone living alone, but hell, if she could afford it, why not? Two bedrooms, each with their own bath, plus a half-bath for guests. Full kitchen, dining area, fireplace. Compared to my shithole, it was a palace.

Molly dropped her purse on the couch, then gestured to the opposite side of the apartment. "Bathroom is through there. Go shower. I'm not fucking you if you don't take a shower. I'll be in mine." I knew better than to suggest we take one together. "I'll meet you in the guest bedroom. Stay in there until I come. And take those with you." She nodded to the black bag and our new toys. "Ten minutes." With that, she turned and headed toward her own room.

The guest bedroom was larger than my living room, which was depressing until I remembered how much I actually made now, and realized that I might be able to afford a place like this now, or soon anyway. It helped some.

The shower was hot almost immediately, another upgrade over my own. I scrubbed with the provided soap, washed my hair, double-checked my shave, not that I could have done anything about it then. I seriously doubted if Molly would also provide a razor and shave gel. After drying off, there was nothing to do but wait.

It was more like fifteen minutes before the bedroom door opened and Molly stepped in. My eyes flicked to her, and I was surprised to find her already nude. She even allowed me a minute to take her in and appreciate: tall for a woman, but not intimidatingly so, maybe... five-seven? Pale skin, light hair, maybe Scandanavian descent? I had observed before that she was shapely, but only had a vague sense of it because of her sensible office attire. Now, I could see full-on that Molly was a knockout: firm, rounded, pert breasts with perfect pink nipples, already slightly aroused; slim waist; rounded hips. I couldn't see her butt, but assumed it must also be statuesque. Her pubic area was bald, just like mine, and between her thighs I could just barely make out the vertical slit of her pussy. She stood on long, toned legs that occasionally crossed as she stepped across the room to me.

"Go ahead, might as well look," she said, distractedly, as she looked for and found the bag.

"Yeah..." I said a little breathlessly, "I am, trust me."

"Enjoy it while you can, loverboy. Don't expect to see it all that often, and not at all once you're ready for the boss." She had pulled out the harness and was adjusting straps.

"So I was wondering..." I started to ask, as I watched her. "Am I going to get to...?"

"Fuck me?" Molly finished. "I don't know. Maybe. We'll see. Lord knows I've got to get something out of this. Trust me, strapping on a rubber cock and fucking your pathetic ass isn't really going to do it for me, you know?" I just nodded. "Maybe I'll let you go down on me or something. If you're good." By now she was stepping into the harness, sliding the leather up her legs. It slid into place like a pair of panties, before she started adjusting.

"I want you to start getting excited. Start getting hard," Molly instructed as she tightened one leg strap. "I'm not going to do it for you. Don't ever expect me to suck that pathetic little cock of yours." The look of disgust on her face was unmistakable.

"Now... wait a minute," I argued. "It's not pathetic or little. It's perfectly average and..."

"Yeah? Compared to the boss?" OK that was a point. Compared to the boss' monster, I was... eh... I didn't... measure up (see what I did there?).

"Fine," I relented, before spreading my legs and taking my own shaft in hand. I had already felt a gentle tingling in my balls, the feeling I get when I just start becoming aroused. Between my motions up and down, and Molly's display, it didn't take long to become semi-erect.

As I took care of myself, Molly found the smaller dildo, the new one we'd just bought, and began figuring out how to attach it to the harness. It wasn't difficult; the suction cup on the back fit inside the steel ring at her pelvis, and just took a little effort to insert. Once in, she twisted her hips back and forth, making the fake cock flop back and forth, testing its staying ability. "That'll work," Molly confirmed.

"Alright," she said, having found the lube and opened it. "Hands and knees, cockslut." My stomach, and my ass, clenched. "How much of this do you need?"

"Um... plenty?" I wasn't sure how to quite describe the amount I usually used on the plug. "Less isn't more. More is more." Molly seemed to get this, and rather than mocking my weakness, she only nodded. I figured I wasn't going to get any more instruction at this point, so I let go of my cock, which was still not fully hard, and crawled up onto the bed, leaning forward, exposing my ass to her.

That first time, I felt every move she made: the compression of the mattress as she knelt on the bed, the soft touch of her hands on my ass cheeks while she stabilized herself, the cold of the lube as it dripped onto my asshole and around the plug's handle. I felt her fingers tighten around the metal handle, and the gentle pressure as it began to slip out of me.

"Once it's out, I'm not really going to wait. I might give you a second or two, but I have to get in before you close up. Got it?" I was a little surprised by her care in giving me the rundown of what was about to happen, but nodded my understanding and my assent. A few seconds later, the plug slipped out of me and plopped onto the bed.

I felt her gripping my hips, then one hand disappear as she used it to line up her cock. I felt the head pressing against my opening, and an almost complete lack of resistance as she pushed forward. I couldn't help it. I groaned as Molly's cock slid into me. I felt the false veined surface, the thickness, the slight yielding of the silicone, not unlike a real cock. I felt her balls press against mine when she finally slid home, all nine inches of her inside me.

"Ohhh... fuck..." I groaned, leaning my head down.

"You alright?" Molly asked, with more care and concern than I'd ever expected. I nodded after a second.

"Yeah... I'm... mm... I'm good." And I was good. She had managed to time her insertion just right so that my ass hadn't collapsed yet. I was given a few more moments to adjust, before she began moving.

At first, Molly moved an inch at a time, letting me get used to the odd feeling of a foreign body part moving inside me. It felt good. No... it felt good. Damned good. I was immediately rock hard, and I'm not sure how I didn't cum right away. Even then, inexperienced as I was, I knew she was pressing on my prostate, and that many men ejaculated instantly when it was stimulated. I didn't, but wasn't far from it either.

It took almost a full minute for her to back all the way out of me, and then the same to reinsert herself. My ass clenched around her cock, at one point making it more difficult for her to enter. We both powered through, she pushing into me, I pushing back against her, until our balls again met. I gritted my teeth against a pleasure so intense it was almost unbearable. I need more, needed more of this girl's cock.

"Molly... don't... don't fuck me... not yet I can't... but just... You don't have to go too slow."

"Is this turning you on, cockslut?" she whispered devilishly. "Do you enjoy having my cock inside you?" I could have said "no", but that was not believable. Saying "yes" would have brought on more ridicule, I was sure. My options were limited. I nodded. "I can tell. Mm... you are a cockslut aren't you? If you want it, you have to ask for it."

Shit. She was going to make me beg. But damn it, I did want it, and not only because it would keep me in good with the boss. "Please, Molly. Fuck me," I hissed.

"Oh... no no no..." she replied, mockingly. "No, be a good little cockslut. Beg."

It wasn't enough that she was fucking me in my ass, she had to humiliate me as well. "Molly, please, fuck my ass... with your... big cock. Take my ass, have it, do what you want with it. Just... just put your cock inside me, please..." God... even now as I remember, I sounded so pathetic.

I loved it.

"I guess that'll do," Molly condeded. "I'll have to teach you some time though." And with that, the teasing was over. Again, she didn't fuck me, but her hips, and her cock, were now constantly in motion, filling me, emptying, filling again. I felt my toes curling and my balls tightening with each stroke, as that long, thick cock penetrated me for the first time. I didn't last long.

I think I managed about a minute my first time, which wasn't bad I suppose. One minute of a large rubber cock filling my ass. I still get butterflies thinking about it right now, and at the time, could only wonder just how wonderful my boss' real cock was going to feel. It was that thought that finally sent me over the edge: of my boss finally filling me with his massive cock, opening me even wider and deeper than Molly was now; of him taking me from behind like this, and her taking my mouth, or maybe one of the clients, so that I had a real cock behind and in front. That was when the first spurt of cum shot from me and splattered onto the clean, white sheets.

I flooded the bed between my knees, my thick cum shooting in heavy bursts, the whole time Molly still sliding in and out of my ass, riding me as I came. I was moaning, panting, possibly saying words without any real meaning. After what seemed like hours, I finally came down. Sensing that I was done, Molly pulled out, then slapped my ass with her new cock.

"Fuck, cockslut!"

"Hmmf? What?"

"You made a fucking mess on my bed."

"Hm... sorry. Couldn't... help it really."

"Uh huh. Well, you'll need to clean that up."

I nodded. "Where are your paper towels?"

"With your tongue, dumbass."

I lowered my head again. Of course with my tongue. I pulled in a heavy breath, then nodded. I got back on my hands and knees, then rotated, so that my ass faced away from her, so she could watch. My mouth hovered just over the pool of my cum. I didn't look at her, I couldn't. Instead, I just got to work.

I lapped it all up, every drop of the white sticky substance. It wasn't bad, as I've said before, and of course eventually, me swallowing my own cum would become fairly common. At the time, though, it was still new. I could sense Molly moving, changing positions to watch, to see if I was really doing it. Of course I was.

When I was done, I finally looked up at her. Her arms were crossed under her breasts again, as she appraised the job I'd done. "So... what? Do I go down on you now? Fuck you? Suck your tits? Something? You said you wanted something in return..."

Molly smirked. "I changed my mind. Your cock is too small to fuck me, and from what I just saw, you're god-awful with your tongue. I'm just going to get the dildo the boss gave me and fuck myself with it. It's bigger than you are, and it'll last a lot longer. You should get yourself cleaned up and call a cab. You're not sleeping here tonight." With that, she turned, cock wobbling, and left the room. I didn't see her again that night.