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.
