First, I'm sorry this one took a while. This is a busy time of year, even (or maybe especially?) for a CockSlut.
So we last left off on that first night when Molly fucked me, using the smaller dildo, trying to get me used not so much to the size, but just the hesitation that comes with someone coming up on you like that from behind. Apparently I was stretchy enough, but just clamped up from nervous anticipation. We used the smaller dildo so that, even though I was clenching, there was still enough room to get it inside me.
Suffice to say that the plan worked. By the third night I wasn't really clenching at all, and halfway through we switched to the larger dildo, the one that was so very close to the boss' cock. Molly insisted, and I agreed, that we practice with it for a few nights just to make sure there wasn't going to be another false start once she handed me back over to the boss.
It wasn't all just work though. After the first night, Molly stopped kicking me out right after. The fourth night, she even slipped into bed next to me, pulling the sheets over us. There was something oddly sweet about it, even though she kept the harness and dildo on, a not-so-subtle reminder of who was in charge, and who was fucking whom.
Starting on the fourth night, I think, she had me start trying to suck her off, using the larger dildo. She said it was to practice, to get used to the boss' size. Apparently the boss was overall happy with my cock-sucking skills, but wanted me to learn to take all of him. I... had no idea how or even if that was possible, but we tried. I got better, but still couldn't take the whole thing, not yet.
On the fifth night, Molly gave me head. It was approached matter-of-factly. Molly said that she needed to get herself in the mood, that giving head turned her on, and that she wanted to before we started. Of course I didn't complain, didn't hesitate really, and was hard nearly instantly.
Now, I'm not hung like my boss is. I've said before, he's over ten inches long, and very thick. I'm nothing like that, but also not entirely a slouch. I'm more or less average, but could maybe make a girl choke if she tried to take it all. Molly, though, must have been a pro or something, because in one motion she swallowed my whole length. She sucked me with surprising enthusiasm, stopping about a minute or so before I would have cum. Apparently that was enough for her, and I noticed as we changed positions just how stiff her nipples were, and how slick her pussy seemed. I guess it did do something for her, and that would have been the end of my curiosity, except that a minute later, while fucking my ass, her hand slipped around and under me, and stroked my cock with each thrust.
A week into our practice, Molly again lay next to me after fucking me, the sheets tenting from her massive dildo. We were close, but not touching. There was no intimacy, certainly no romance: this was just sex.
"I think you're ready," she announced suddenly. We hadn't been talking, and the room had been nearly silent. "I'm going to tell the boss tomorrow. He'll probably want you right after, to make sure for himself. So, you know, be ready for that."
I nodded. I knew that day was coming, and my stomach gently churned with anticipation. "You think I'll do OK?"
"Yeah, honestly. I think you'll be fine. Just remember to breathe and relax. He's just as big as this dildo, but no bigger, so he should feel just like it does." She reached down and grasped "her" cock through the sheets. "If you can take this, you can take him." I only nodded, and again the room fell silent for a while.
"So... then I guess there's no need for us to keep doing this, right?" I asked after a few minutes. Molly shrugged.
"I guess not..." she said, and I swore I heard just the tiniest hint of reluctance. For the first time, I looked at her.
"I mean... unless you want to..."
"What? No," she insisted, indignantly. "I... no I don't. I mean... look it's been fun and all. You're... not a terrible fuck, I guess." That was an interesting statement, considering I hadn't actually fucked her. "Not many guys would let a girl peg them with a monster like this so... you have that going for you I guess. And... you... kind of have a pretty cock, so there's that, but that's it. There's nothing going on with us. This was only because the boss insisted."
I nodded, but couldn't get past the fact that she had actually complimented me, twice. "That's fine," I said, knowing that I hadn't really expected anything. "But you know, if you ever feel that itch..."
"Here's how it's going to work, CockSlut," she said suddenly, turning her body to face me. "When I feel the urge to either fuck or be fucked, I'll tell you, probably before we leave work. You'll come over, we'll do the thing, and that's it, alright? No emotions, no attachments. I don't love you or even like you. You're just convenient and happen to like the things I like. Got it?"
Molly had said "fuck or be fucked". She wanted me to fuck her? I asked her.
"Maybe, sometimes, it depends. I don't know, for all I know you're terrible with that thing." She gestured toward somewhere between my legs.
"I dunno," I said, suddenly finding myself with just the slightest leverage. "I mean, it's not that big, not compared to..." Like she had, I gestured between her legs and the massive pole holding up the sheet.
"So?" she replied, seeming... what? Bitter? That was out of place... "Sometimes bigger isn't better. This thing? It's massive, and would probably hurt like fuck. I can't imagine how you take it, and in your ass no less. A pussy at least is intended to be stretched out a little bit. Your butthole? Not so much. No, your little dick will be fine."
A compliment and an insult, one right after the other. Only Molly. "And what if I don't want to come over and fuck you, or be fucked by you? What if I'm perfectly fine being a fucktoy for just one person?"
Molly shrugged dismissively. "Fine. Do you really think you're the only guy in the office who would race to my apartment if I told him I was DTF?"
"No," I said with a slight grin, "but you basically said yourself that I'm the only one who is into the things you're into. I assume you mean the whole pegging thing. I get it, that's rare, and you're probably not going to easily find it."
She seemed to consider this. "No... no not really." She huffed, a little frustrated. "Fine. Can we just agree to it then? There's no... we're not a couple, no relationship of any kind. Fuck, we're not even friends or fuckbuddies. We're two people using each other to get our rocks off and that's fucking it."
I held out my hand to her to shake. "Deal." We shook.
The following day was a Friday, and while the office was always busy, Fridays seemed to back off a little bit. The pace felt slower, and there was a chance to take a breath from the rest of the week. It also meant that the boss could take his time with me, if he was so inclined. It was the perfect opportunity for our first time.
As always, Molly was there before me, and I swear to god she shot me a brief, but cordial smile when she saw me. "I told him you were ready," she said as soon as I was close enough, and I started to wonder if the smile was related more to her knowing that I was about to get my ass reamed than any actual pleasure at seeing me.
"So is he waiting for me then?" I asked, staying by her desk rather than taking my usual seat as I waited.
"Oh he's ready," she said, her smile growing a little bigger, and maybe just a touch... sinister. "I cleared the whole next hour from his schedule, just so you two can have some... quality time..."
I took in a breath and let it out. "Alright, fine. I'm just... going to go on in then," I said, pointing to the door and steeling myself.
The boss was behind his desk, as always, except that morning, there were no scattered papers, no notepads, no pens, really nothing on the desk at all, and he was actually looking at me when I came in. "Morning boss," I greeted him, locking the door behind me.
"Well, good morning, CockSlut," he said warmly. "Molly tells me you've been doing very well in your training. Is that true?"
I nodded. "Yessir. We had to work up to the dildo you gave us, but I can take it now. I've gotten better at sucking it too. I can get pretty far with it now."
"Is that so?" he asked, sounding surprised and impressed. "You did that just for me, hm?"
"Uh... yeah boss. Just so I could take more."
"How nice of you," he said, sitting forward. "Now is a great time to show me, I think. We should have plenty of uninterrupted time."
I nodded as I started undoing my tie. "Molly said she cleared us an hour. For 'quality time' she said."
The boss chuckled. "Well, the quality will be up to you, now, won't it?"
I didn't reply, and instead just continued undressing, and was soon entirely nude. I had freshly shaved that morning, and carefully. I was as perfectly smooth as I had ever been, figuring it would help to make a good impression.
"Welp, on your knees," the boss ordered once I'd fully undressed. I did as I was told, as he stood and began undressing. I noticed his cock wasn't at all hard or even engorged, not yet. I guess that was all up to me.
He came over to me, towered above me, his monster hanging just in front of my face. No words, no orders were needed: I knew what to do. Placing one hand on his large, heavy balls, and the other around his flaccid shaft, I leaned in and gently kissed and licked the head, sort of humming, sort of sighing. We hadn't done anything, not even this, since the last failed attempt at anal, and, frankly, I missed his cock. The fake one just wasn't the same. This felt softer, warm against my lips. After a minute, I could feel his pulse running through it as he started to become erect.
I kept kissing and lightly licking until he was fully erect, but decided to be a bitch and teased him instead of taking him. I leaned in farther and sucked one of his huge balls into my mouth, rolling it with my tongue, gently sucking. He moaned a little and even gently touched the top of my head for a minute. I took the hint and kept going, making love to his testicle, then switching to the other after a while. Again I sucked it into my mouth, caressing it, loving it, sucking it. The whole time I held his massive cock out of my way, my hand wrapped around the shaft but not moving. That would be my mouth's job.
When I thought I had teased enough, without warning, I removed my hand from his shaft and put my mouth over the bulbous head, pushing down, down, down until I had taken decidedly more than half. I still couldn't do it all, but was getting much closer. I held him in my mouth and down my throat for a minute, humming, sending little vibrations through his cock. Then I pulled back and entirely off him, a string of my saliva connecting my lower lip to his tip.
"You have been practicing, haven't you?" he asked, clearly impressed. I didn't bother replying, and instead again sank my mouth down on him, taking at least as much as before, maybe a little more. He groaned as I pulled back, sucking hard. I stopped while I still had the head in my mouth, then sank again, pushing myself some. I knew I still couldn't get it all today, but I was going to get as much as I could, and not just for him. Fuck, I loved having his cock invading my throat, and I felt a warm rush of excitement when I remembered that it was about to invade my ass too.
I made sure to go slowly the whole time, neither one of us wanted me to make him cum yet. He stopped me after another few minutes of this. I teasingly backed off, taking my time, rolling my tongue over and under him, and let the head out with a pop. "Bend over the desk," he told me, just like last time. I nodded and got to my feet.
The desk again had been cleared, and there was plenty of room for me to rest my upper body on it. I was no less nervous than the first time, even though I kept telling myself that everything had gone right when Molly and I tested this out. He should be able to slide into me without much effort, as long as he used plenty of lube.
A desk drawer opened then shut. I heard a bottle or tube being opened, and then the gently squishy sounds of lube being applied to a hard dick. I tried not to clench, not to panic, and breathed like Molly had said. Then I felt his hands on my hips.
It took a moment to line up, but the boss' cock head wound up pressed perfectly against my puckered opening. I only felt a single hand on me now, so figured he must be holding his long shaft for better aim. Then, the pressure. It was consistent, but gentle, and before I had time to clench, to allow myself to resist, the massive head of my boss' cock pushed into my ass.
I groaned, as he had before. It did feel like the dildo, as far as size, but the pliability and the warmth were completely different, and so much better. Plus, the idea that this was another person inside me, rather than just a piece of rubber.
He was patient, thankfully, and took his time, although probably more than he needed to. Every several seconds he'd push in another inch. It took just over a minute before he was buried in my ass, and I swear to god when I felt his balls press against my own, knowing he was all the way in me now, I almost came right then.
"Fuck..." I gasped, and he asked if I was alright. "Yes... " I hissed, "it just... feels... so damn good..." He said nothing in response, and waited a minute, before he started pulling back out. I could feel my insides collapsing around where he had been, and it felt empty and lonely. He pulled back just to the head, then pressed forward again, filling me to the hilt. "Jesus..." I muttered, clenching my eyes shut.
The boss took his time, working up to a slow rhythm. We were in no hurry, after all, and it was my first time with him, so he was being gentle. Still, it didn't take too long before I was actually, properly, being fucked. Soon the boss was sliding into me easily, with a little bit of force, and with each thrust, his balls would swing up to collide with my own. We were both grunting or moaning each time he filled me, and his grip on my hips tightened.
I had never felt this, not even with Molly, this thrilling sense of excitement and absolutely horniness. I wasn't going to last much longer, and as it turned out, neither was he.
A minute later, I began to cum, hard. Cum shot from the end of my cock all over the floor, each load splattering with impact. Just after, I felt him throb inside me, heard him grunting loudly, then felt the hot, sticky flood of his own cum filling my ass. That only set me off more, and as my ass gripped him, my cock unloaded between my legs. He was still fucking me, letting some of his cum leak out of my ass. It slid down my crack, behind my balls, down my thigh. I groaned, and after a little longer, he pulled out.
I stayed across the desk for a little while after, collecting myself. When I pushed up, I felt suddenly exhausted. I turned to look at the boss, although he wasn't looking at me. His face and chest were flushed, and he was still breathing a little heavily. He cleared his throat then, as he started to get dressed. "Not bad," he said with a nod. "Not bad at all." I realized that was probably all the praise I was going to get, and that was fine. I knew what he meant.
We went for a second round a little later, still within that hour that Molly had cleared. When we were done and I left the office, Molly gave me a knowing look. I just shrugged as I walked past. I didn't go to see her that night, and she didn't ask me to. That's another story anyway.
Editor/Story Consultant: A. Burns