Author: Cheerleader Fan
Title:  A Late Night At The Office
Summary: Grant must stay late at the office to help his beautiful boss complete an important project, but things soon take a turn for the erotic.
Keywords: MF oral anal caution

Lets get the easy stuff out of the way first. My name is Grant Lang. I'm an office drone at a company called Anders and Stevens. It's not really important what we do. I just push paper and help make things happen for the guys who bring in the real money and sign my checks. I'm making it sound worse than it is, really. The work isn't difficult and it allows me to flex my creative muscles writing up proposals and such. In fact, writing proposals is exactly where this whole story starts.

I've been here for a few years now and at first it was so laid back as to induce comas in some of us. My boss at the time was an older gentleman without much ambition, which was understandable given how close he was to retirement when I started. Well, that retirement happened a few months back and my new boss couldn't be any less like him if she tried. Starting with that, in fact. She's a woman and quite the knockout, too. She always dresses smartly and professionally, but only just barely so. A typical outfit for her might be a form fitting black skirt several inches above the knee, to the point where if you caught her at just the right moment in her stride you might see a hint of the lace tops of her stockings. On the other end of those stocking she always wears heels. I don't think I've ever seen her in anything less than four inchers. She's already fairly tall for a woman, so even though I'm somewhere around six feet tall we see just about eye to eye. Above her waist the norm is a tight fitting blouse inside a smart suit jacket, pinched at the waist to accentuate her hourglass figure. Her full breasts always look to be fighting with her wardrobe and one of these days I swear they'll win. It should be noted, by the way, that I described this typical outfit because it's what she's wearing today and I'll be god damned if it doesn't make concentrating on my work difficult. It also doesn't help that she's got something approaching super model good looks in the face department as well. Her lips are always painted bright and shiny and her vibrant red hair is smartly done. Usually she wears it up in a bun, but today she's sporting a high ponytail tied with a black and white scrunchie that matches her outfit perfectly. She also wears a fashionable pair of glasses that I think enhance her beauty rather than detract from it.

Anyway, what I was going to say before I got sidetracked by... something... is that as a boss she's nothing like the last guy. (Oh right, how about a name? Hers is Gloria, Gloria Libbey) Gloria is an achievement oriented woman looking to advance in this company. As such she expects a lot more out of her employees than we were used to and she gets it. That was a welcome change for me since without much effort I was already one of the top employees of the department. Now that she's the boss the people that used to be dead weight are pulling their fair share and I can do a much better job with my now smaller workload. In fact the only coworker who was my equal here was her. She even gave me the professional courtesy of informing me that she was going for the position, but I think part of that was that she knew I had no desire to have it for myself. I've got little interest in the world of management whereas she was made for it. I think she was also gauging how I'd feel to have a female boss and hey, call me progressive, but I don't care what's in someone pants (or skirt) so long as they can do the job well.

This workday was finally winding down and I was putting the finishing touches on one of several projects I'd been working on lately when Gloria's door swung open and she casually made her way to my desk.

"Lang," she called as she closed in. Since getting the promotion she'd taken to calling her employees by last name, possibly as a way to distance herself from those who had till a few months back been her peers, I'm not sure. Some hate it, but honestly I quite like it. It's like she's playing formal and I can't deny that because of the way she presents herself, having a woman in charge has quickly become a turn on for me.

"Yes, Miss Libbey?" I like to play formal right back.

"You're a team player, right?"

Her expression was friendly but neutral. I couldn't tell what she was getting at.

"I'd like to think so."

"You know the Michaelson contract, right," she continued.

"You know I do." Of course I had. It's one of several I've been working on lately.

"I just now received word from the higher ups, the timeline has been shifted."

I raised an eyebrow. "And?"

"You know I hate to drop something like this on you last minute," Gloria spoke, appearing to choose her words carefully, "but they need the preliminary proposal tomorrow morning which means I need it tonight. Can I count on you to help me with this?"

"I'm supposed to meet with friends for drinks later, but I'm sure they'll understand."

"I knew you'd understand, too, Lang," she smiled and rubbed my arm in a friendly manner. "It's going to be a lot of work, but I think we can get it done."

"Would you like a pleasant surprise, Miss Libbey?" I asked with a wide grin.

"What's that," she asked, her interest piqued.

"I've had some free time lately," I began as I spun around to face my computer, "so I'm a lot farther along on the Michaelson account than the timeline demanded. I opened the project folder and began clicking through it, showing her much more than we should have had finished by now.

"This looks very promising," Gloria said, sounding much closer than I expected her to be. I turned towards her voice and found my face inches from one of her heavy breasts. I looked up just in time for her to look down at me. "You're quite the wordsmith, Lang. Tell you what, I'll crank away at the graphics and you on the text. We'll meet and compare in an hour."

"Sounds like a plan, Miss Libbey," I agreed.

"Ohh and by the way, they've made a few minor changes, here," she straightened up and handed me a thin folder, "I'm sure it won't take much to incorporate them. I'll ring you soon."

"Yes ma'am," I agreed and got to work as she left my desk. A moment later I looked up to watch her hips sway as she walked the aisle back to her office. Her news wasn't exactly the most welcome, but at least I could watch the messenger's beautiful ass wiggle she walked away.

I looked over the updates in the folder Gloria had handed me and she was right. It wasn't going to be very tough to work the changes in with what I already had so I got down to it. I was hammering away at it as one by one my coworkers filtered out. It was twenty minutes past office hours when Parker, the resident suck up, finally decided to give up on the day. Usually he made sure to be seen as the last one out and I wished he could be. Once the door closed behind him I was alone in the office, aside from Gloria, of course. Only a couple minutes later my phone went off and I grabbed it on the first ring. God I hate that noise.

"Yeah, boss." I answered. Knowing it could be no one else.

"You ready to compare notes, Lang?"

"Sure thing."

"Door is open."

I hung up, knowing Gloria didn't care for time wasting formalities on the phone. I quickly saved my work to the project folder and headed to her office. I walked in and took a seat at the desk opposite Gloria, who wore a satisfied expression.

"How's your end coming along," she inquired.

"I think I'm nearly there, and you?"

"That's what I wanted to hear, Lang. Good progress on my end, too. We can't get much done with you over there, though. Grab a seat on this side and we can go over what we have."

I stood again and made my way to her side of the desk. From my vantage over her I had a fantastic view down the front of her blouse, aided by the few buttons unfastened at the top. I was sure those had been buttoned when she delivered the bad news earlier. Well, now they weren't and not only could I see plenty of cleavage, but I could also see a generous amount of her bra, white silk with fine black lace trim. On her side of the desk now I pulled the stool nearby up next to her and took a seat. This close to her and in her office the scent of her perfume, which I found rather intoxicating, became inescapable.

"OK, let's see what we have here."

The sound of her voice snapped me from my reverie. I blinked twice before focusing on her computer screen. She was quickly cycling back and forth through what we had of the proposal and making murmurs of approval. I must admit, her graphic work was top notch. Knowing the strengths of her people and herself had served Gloria well so far and surely it would be noticed on this project as well.

"Thanks to your prior dedication it looks like we'll finish this thing a lot sooner than I anticipated, Lang," Gloria stated matter-of-factly. "I think it's obvious where we go from here. It shouldn't take much longer before we're done. Anything you need to add?"

"Not really," I began. "It's like we were right on the same page with your graphic work and my content. Given how little we had to go by that's a nice surprise."

"I thought so, too, Lang." Gloria turned in her chair and faced me, satisfaction evident on her face. "You said you were planning to meet some friends for drinks?"

"Yes ma'am, I was," I answered quickly.

"I know we're only officemates," Gloria began as she eyed me casually over her glasses, "but I think we deserve a short break right now and I'd be happy to pour you a drink... if you'll accept."

"I'm not about to turn you down, Miss Libbey," I answered, trying not to let my excitement show. "So, what are we drinking?"

"That depends, Lang, Feeling adventurous?"

"Certainly curious, now," I answered. "How can drinks with my boss get adventurous?" I doubt she'd care to hear how I'd like to make things adventurous.

"Well, the standard route would be some top shelf scotch," she began, "but my pool guy's got some connections and I came into possession of something of a unicorn." Knowing my interest was high she ended her statement by placing a couple low balls she'd fished from a drawer on her desk as well as an oddly shaped clear bottle three quarters full of brown liquid. There was no label. "This," she stated proudly, "is 12 year oak barrel aged moonshine." She eased herself back in her chair and simply smiled ear to ear, hands behind her head.

"Well, you got me," I clapped twice and continued. "I have never had aged shine, can't say I've even heard of 12 year stuff. Everything I've had was like paint stripper."

"Turpentine this ain't. You're down, yes?"

I nodded and she poured both glasses. Over the next several minutes we took pleasant pulls from our glasses as we shot the shit. It started off about work, but quickly jumped to other topics. We each learned a little about the other and as our glasses approached empty she refreshed them, swearing that after this one we were getting back to work. The shine was damn smooth, but also damn powerful so I was feeling a little looser and I'm sure she was, too, when she bluntly asked me why I wasn't pulling in all the ladies. I guess she had heard through the grapevine that I'd been single for quite a long time now.

"To be perfectly blunt, 'all the ladies' doesn't really do it for me when I've got a specific sort of lady in mind." I told her. I didn't really put much thought into what I said, wasn't even sure what I meant by it myself, but it felt fitting.

"And what kind of lady is that?" Gloria inquired, the gears in her head obviously spinning. Did she know what I meant better than I did?

"I dunno," I said with a laugh, "but not just anyone."

"Ohh I think I know what kind of lady you're after," she said with a loud laugh, "but trust me, I'm too much woman for you."

"Wait... what?" I said dumbfounded.

"You heard me. I'd have to be blind not to notice the way you look at me."

"Whoa!" I responded. "You don't exactly make yourself easy to ignore."

She let out another raucous laugh before straightening up in her chair and giving me the eye again.

"So you admit it?"

"Admit that it's hard to keep my eyes off a beautiful woman? Sure."

"That's not what I meant, but we'll have to continue this in a bit, we've a proposal to finish."

"Sure thing, Miss Libbey," I chirped. The ability to switch gears at a moment's notice was another strength I think Gloria appreciated in me. I stood once more, again appreciating her breasts from above, but only for an instant, before heading out of her office. I found it hard to ignore my erection as I made my way back to my cube.

I did my best to put myself into work mode and mostly succeeded, but after our brief conversation I couldn't help thinking about Gloria, her stunning body and all the things I'd like to do with it. I was able to get my shit together, though and I finished my part of the proposal to my satisfaction before the phone went off so I spent the next however long it took just going over what I had with a fine toothed comb. By the time the phone rang I'd managed to find three minor errors and fixed them. Again I grabbed it on the first trill.

"Yeah?"

"You good?" she asked.

"Done and done," I replied.

"Same, come on in and we can finish this."

I dropped the phone and headed into Gloria's office. She motioned for me to again take the seat next to her. The two of us went over what we had and made sure everything aligned well. After she made the last changes Gloria saved the project and closed it out.

"This is fantastic," she gushed, "There is no way the higher ups can be anything but satisfied."

"Good to hear."

"No, I mean it," Gloria continued. "I know you'll be seeing something for this, but if for whatever reason they aren't happy with it I'll find a way to make tonight worth your while."

"Nice of you, boss, but I'm good."

"And what do you mean by that, Lang?"

"This has easily been the best shift of the year for me," I answered honestly. "It's not every day your boss shares her finest shine and some interesting conversation with you. It made the work a pleasure." I smiled to ensure she knew I was sincere.

"You're my best man here, Lang. I wouldn't have come to you with it if I didn't think so and I must admit I enjoyed our drinks as well. If it wasn't so limited a supply I'd pour us another round."

"Oh that's fine, Miss Libbey, as nice as it was I've had enough for now. I'm curious though..." I trailed off.

"Curious about..." Gloria trailed off as well.

"Whether we're going to continue that conversation where we left off."

"I knew it," Gloria laughed 

"Ohh I'm mostly curious about this too much woman brag of yours," I emphasized my words with a bit of a laugh before continuing, "I'm not involved now, but I've been around the block and believe me, I've handled the vast majority of women that walked my way."

"That a fact?" She was taunting me now.

"You can bet that perfect ass of yours it is," I grinned.

Gloria's face turned an interesting shade of red before she finally responded. "I'm going to give you the opportunity to forget this conversation ever happened, Lang, but if you can't do that I'll prove myself right just for you. *IF* you want to try me this never leaves this room on penalty of your job and a sexual harassment suit on top, understand?"

I swallowed hard. I didn't expect her to bring the big guns like that. All of a sudden I wasn't so sure I wanted this.

"Well?"

I knew it was an insane risk given the threat she just levied, but I couldn't pass up such a tempting offer. I nodded.

And like that she was on me. She mashed herself against me and forced her tongue into my mouth in a most violent and surprising kiss. Her hands were all over my body, feeling my chest, grabbing my ass, one hand came right up and clutched my stiff member. I took hold of her ass and did some groping of my own in a sorry excuse for keeping up. It felt as spectacular as I expected it would. I just kneaded it, luxuriating in the feel. Gloria though, she was still groping me the way I'd expect the Hindu Goddess Shiva would, as it felt like she had far more than just two hands.

Finally after what seemed like an eternity Gloria broke the kiss. We were both panting. "Wow," I gasped at her.

"We're only getting started, little man," she laughed. "if you've even got the nerves to handle me, that is." Her hands were on my shoulders now and she was pushing down, with a surprising amount of force for a woman. I could have remained standing, mind you, but at this point I wanted to obey her, so I let her push me to my knees. She looked down at me with a wicked grin and grabbed the hem of her skirt. I looked on, enraptured, as she slowly lifted it, first showing me the bottom edge of her lacy black stocking tops. Gloria moved her hands at a deliberate pace, the clips to her garter belt finally appearing after what felt like an eternity. Another eternity passed and the garter straps came into view along with the pale white flesh of her thighs. Ever higher she lifted her skirt till it reached what had to be the point where I'd finally get to see her panties.

And then she just let go. Her skirt stayed where it was hiding that most precious of places. So focused on that was I that I hadn't noticed what her hands were doing now till I felt a tug on my neck. I looked up to see Gloria holding my tie taught. Our eyes locked and again she gave me that wicked grin.

"I bet you want to see my pussy, don't you?" She was again mocking me. "Don't you?"

That she asked a second time was all I needed to hear to know that she wanted an answer. "Yes, Miss Libbey," I played into her game, hoping that's what she wanted. "I want to see your pussy." 

"Well, that's too fucking bad," She laughed as she released my tie, grabbed the hem of her skirt once more and yanked it to her waist. I was eye level with her crotch so I dropped my gaze to look forward, expecting to see a cute little pair of panties framed by a garter belt hiding Gloria's equally cute little pussy. That is not what I saw, however. She was wearing a pair of French cut white silk panties with black lace trim that perfectly matched both her bra and garter belt, but trapped within those panties was a sizeable lump of cockflesh. Caught completely off guard I dropped back, catching myself with my hands behind me and I just looked up at my boss, confusion painted across my face. Then I looked back down at the monster imprisoned within her panties. It felt like minutes passed as I just stared at her package. 

"Yeah... I didn't think so."

I finally looked up at Gloria again. She looked disappointed.

"If that's all then..."

"Hold the fuck on."

Had I really said that? The gears in my head were spinning now. I was sharp enough to realize that even though this was a completely unexpected turn of events it was also significantly less likely than a once in a lifetime opportunity. Gay, straight, other. None of these things mattered in this moment. If I turned away something like this would never happen again and I know myself too well to know that no matter how it turned out if I did it, if I didn't I'd always kick myself over the opportunity I let slip away. Also, knowing her secret I now knew why she made the threat earlier. I could definitely forgive her, considering.

My mind was made up.

I got back up on my knees before her and reached out to touch it. Her cock felt large and hot against my right hand through her panties as I brought my left up to cup her balls below. I just caressed her womanhood for a few moments. I don't know why it took me off guard when it happened, what with having one of my own, but I was rather shocked when Gloria's penis began to grow in my hands.

"Ohh yeah, that's nice."

I was proud that she liked what I was doing with her member so I did what seemed right. I pulled her panties to the side and pulled her cock out through the leg hole. Once free it leaped out at me so I grabbed it with my right hand, sliding it down to the base. Then I brought my left hand into play, my hands touching at index and pinky fingers. What was utterly amazing was that she still had a number of inches spilling out past my left hand, ending in a large cockhead which was dripping with precum. Again I looked up at her. This time rather than disappointment my boss wore a look of satisfaction. Wanting to keep her happy I looked back down at her twitching cock before considering my next action. It was at this moment I noticed the smell of her womanhood. It was musky and strong, but nothing like mine. Her cock, massive as it was, still held a very feminine scent. Captivated by that I smell I decided I wanted a taste as well. My tongue first hit the underside of her glans, giving me a taste of her precum. It tasted as good as it smelled, so I continued tongue-bathing her penis, licking every inch of what flesh protruded past my hands. I found myself suddenly addicted to my boss's cock, but I felt unsatisfied. Driven by my newfound lust for cock I gave the head a few wet kisses before engulfing it. At that point the noises Gloria made shifted from ahs and moans to grunts. With a bit of effort I could fit the top of her cock in my mouth, but I wanted more. No, I needed more, so I pulled my left hand away and began inhaling more of my boss's beautiful cock into my mouth.

At that point something snapped in Gloria. Her hands grabbed me by the hair and she started thrusting at me. Suddenly I was almost completely out of control. The only thing keeping her from ramming her tool down my throat and choking me out was my right hand and its stranglehold around the base of her cock. This was about to change, too. Gloria shifted a hand to the top of my head, still grasping my hair and forcing me onto her or herself into me. It was tough to tell which was actually happening. Then I felt her left hand grab me right by the wrist. I tried looking up, hoping I could reason with her as she drove into my mouth over and over. It was hard to see past her heaving breasts, but the woman who was my boss was gone. Her face was angry and the only communication she seemed capable of were grunts and groans of ecstasy. I was tired and out of breath so it didn't take too much for her to wrestle my hand away from the base of her enormous member. When it was finally free of my hand she drove herself forward, forcing her fully engorged womanhood down my throat. I fully expected her to start fucking my throat at this point, but that's not what happened.

Buried as she was in my gullet I felt her massive cock start to twitch and I realized then what was about to happen. A moment later she shuddered and began literally pouring her semen straight into my stomach. As out of it as I was I was briefly saddened that this meant I wouldn't be able to taste her cum. Next time, I thought. Yeah, I guess I was already resigned to servicing her again, should she want that. Gloria pulled her cock out of me in one swift motion and I realized she'd already finished filling my gut.

"You OK?"

I looked up and to my relief the sex demon of a few moments ago was gone and my boss was back. I nodded, as exhausted as I'd ever been from using my mouth.

"I must admit, Lang, you did indeed handle me like you said you would," Gloria praised. "Most of my prospective partners are far too intimidated to do anything but run."

"I think it was you that did all the handling, though."

She laughed.

"So I guess you're just fine with all of this," she motioned at her large cock, which appeared only slightly less rigid than it had been when it was jammed down my esophagus.

"It's definitely not what I anticipated, but yeah... it was an interesting experience."

"And you'd like to continue this experience?"

Looking up at her I nodded.

"I notice that you haven't had any, relief, yet," Gloria continued. "Would you like some?"

Again I nodded.

She knelt down before me and approached, initiating another series of kisses. These were much less urgent than they were before. I suppose that orgasm she poured down my throat mellowed her a bit. I reciprocated, enjoying this much gentler exchange. A moment later she broke away, then her hands were at my waist.

"Alright Lang, let's see what I've got to work with here," she deftly manipulated my belt as she spoke and in moments my cock was free. "Hmmmm... this'll do it," she rubbed me to full hardness as she continued her evaluation of my penis.

"It'll get the job done, Miss Libbey," I ensured her. "I'm told it's above average, but I don't think the scale really applies given what you're packing."

Gloria laughed then looked me in the eyes. "I suppose I am on the outer edge of the bell end curve, aren't I?" she exploded into laughter at her joke and I joined her. "But seriously, though," she left the thought hanging as she dove forward and inhaled my penis, leaving me dumbfounded as her nose quickly tapped my stomach.

"Holy f... UHHH!" I exclaimed, my words quickly turning to nonsense as I felt her throat muscles start to undulate. Given what she was doing to me I was somewhat out of it, but it felt like quite a long time before I felt her pull away, my cock sliding back out of her throat. I did not hear her gag or even gasp for breath. When my senses returned I looked down to see her looking up at me, a broad smile playing across her face.

"Did you enjoy that?" she giggled.

"Uh huh," was all I could manage.

That's when Gloria went back to task, again engulfing my entire member. She sent her throat muscles into overdrive once more, but only for a moment this time. When she stopped, she began lifting off of me only to impale her mouth yet again. She continued this action repeatedly. In an absolute blur of motion she fucked my cock with her face. I could do nothing but groan and revel in her expertise. Again I heard no signs of gagging as she abused her throat with my cock. Thankfully she pulled away after not too long because I was fast approaching release. This time when I looked down at her she caught my eye only briefly before giving a sweet kiss to the head of my cock.

"Oh my god, you're incredible," I gushed.

"I get that a lot," Gloria responded. "I figure if you're gonna do a job you do it right. That goes for blowjobs, too."

"Well, you're definitely doing it right," I agreed. One thing though..."

"Hmm?"

"I gotta see those tits of yours."

"That's extremely unprofessional of you, Lang," Gloria reprimanded as she shrugged off her suit jacked and began unbuttoning her blouse. Before tonight I had no idea she had such a good sense of humor. When finished she pulled her blouse from the waist of her skirt, leaving hanging as her hands went to the clasp between her sizeable breasts. She looked up at me and smiled again as she opened that clasp and freed them. Given how well endowed she was downstairs, the way her tits practically defied gravity should not have surprised me. They were perfectly formed and capped with large pink nipples. They were puffy, but not grotesquely so like you might see in some freak out porn. I wanted to taste them.

"Those are incredible."

"Yeah, I know," was all she said. Then she laid back and beckoned me with a finger. I guess she knew what I wanted. I placed my hands on either side of her then went in for a kiss. She seemed surprised, probably because she thought I'd dive right for those tits, but I'm nothing if not thoughtful. We shared another pleasant kiss before I did indeed seek out her breasts. At first I just squeezed them, caressing them gently before I lowered my mouth to her left nipple. I'd never sucked on nipples like these before and I found the experience left me wanting more. I switched to her other nipple, hungrily sucking it into my mouth. With my right hand I began toying with the unattended nipple, pinching and flicking as I saw fit. As I did so Gloria emitted soft little noises of pleasure. I was glad she liked having her tits fondled and sucked. Breasts as perfect as these really should be enjoyed. Wondering how far I could push it I began to nibble gently on the nipple in my mouth.

"Oh my, Lang, you really are hungry."

She didn't seem at all upset so I put a little more force into what I was doing. If her moans were any indication Gloria was liking what I was doing and it wasn't till I was quite literally biting her nipple that she let out a sound of pain and pushed me away.

"Just a bit much there."

"Oops."

"It's alright, but I feel we could be more productive here."

Is she seriously evaluating our sex play professionally? Yeah, she was made for an executive position.

"What did you have in mind?" I asked, curious how she thought we were being inefficient.

"Seems to me we could accomplish twice as much here if you'd fuck my tits."

Her expression was neutral so I honestly wasn't sure if this was more of her sense of humor. Regardless, I definitely agreed. I stood, kicked off my shoes, and dropped my pants. Once naked, from the waist down, at least, I stood over Gloria and lowered myself. As I did she grabbed her tits at the sides and held them apart slightly. I dropped my cock between her perfect white mounds as I settled down. Wasting no time Gloria used her hands to move her breasts over my manhood. I let this go on for a moment, luxuriating in the feel of her supple flesh as it rubbed along me. I was beyond horny at this point though, so once that moment was over I grabbed her hands with my own and the two of us cooperated in working her tits over my cock, but at a much more insistent pace than she was doing it alone.

"See, I told you this would be more effective," Gloria said as the two of us continued stroking my cock with her tits.

"You're absolutely right, ma'am, this is definitely a more constructive use of our time." It seemed almost ludicrous to carry on a conversation about how to most efficiently engage in sex play, but in the moment I didn't care. I began thrusting my hips in time with the motion of Gloria's tits in our hands and I could feel my orgasm approaching. "I'm about to cum, Miss Libbey. Where do you want it?"

"Paint my nipples, Lang," Gloria almost shouted. "Cover them in your cum. That's an order."

"Yes ma'am," I groaned as I lifted to kneeling and aimed myself at her right breast. I only had time to give my cock three pumps before the orgasm took hold and I launched the first shot of cum at my boss's nipple.

"Excellent work, Lang."

She was really getting into the boss/employee power dynamic here. It was definitely doing it for me too. I grunted and launched another rope of jizz, this one at her left tit. My aim was true, painting the puffy pink nipple white. I was losing steam at this point, but I was able to glaze each nipple a second time before I ran out of semen.

"I'm impressed by your production, Lang."

Holy shit, she was still cracking jokes. This woman is amazing.

"Yes, ma'am. I aim to please." I can crack jokes, too.

Gloria laughed.

"You've really made a mess here, though. I'm going to need you to clean it up."

"OK, where do you keep your tissues?"

"I'm sorry, Lang, I thought you were dedicated." Her voice took on a harsher tone. Again I found myself unsure whether this was a joke.

"Miss Libbey?"

"I want you to clean me up with a more delicate instrument than tissues. Your mouth should be sufficient, and this time no biting."

Again Gloria had me in a bind. I definitely wanted this to continue. Whatever this was, but I never anticipated licking my own semen off of her nipples. On the other hand I did let her jam her own cock down my throat and unload in me, and in that moment I felt resentment that I wouldn't get to taste her cum. Is there really such a difference between mine and hers? I guess that settled it.

"I'd be glad to, Miss Libbey."

I again dove for her breasts, this time starting with her right nipple. I gave it a tentative lick, finding myself actually rather curious what it tasted like. I guess that thing about it being salty is true, since that's the first thing I noticed. I don't mind salt so I threw caution to the wind and latched onto her breast with my whole mouth. That's when I was hit with a stronger flavor. Oddly it was sweet. I expected sour or bitter since that what people tend to call it, but I guess not mine. I sucked her nipple clean then licked all around the area ensuring I got it all.

"That's some good work you're doing. The other one now, please."

I moved to her remaining breasts, taking its nipple into my mouth as soon as Gloria instructed me to do so. I was definitely getting into the subordination and if the stiffening cock that was beginning to poke me in the belly was any indication she was getting off on ordering me to do something so depraved. It didn't take me very long to finish cleaning her up and following a few more licks to pick up a stray drop here or there both breasts were free of semen.

"I suppose that'll do it," I said as I pushed myself off of my boss. As I stood her penis stood as well. I was again impressed by its sheer size. I didn't let that keep me from being polite, though, so I reached a hand down and helped Gloria to her feet. Once I did she came in for a kiss and shoved her tongue into my mouth. I felt it swirling around and suddenly realized she was probing my mouth for the taste of my cum. Was it greedy of me to have already swallowed it?

"Am I wrong or did you enjoy that as much as I did?" Gloria asked after breaking the kiss.

"I'd be lying if I said I didn't," I answered, "but I don't know if it's because of what I did or that you made me do it" I hoped this admission wouldn't put her off, but I had a strong suspicion I was right after all.

"See, I knew it," she said. "You do have a thing for me. If that's the case I've got more orders I could give." She grabbed her impressive member to emphasize her point.

"Well, Miss Libbey, you're the boss." I hoped these words wouldn't wind up hurting me, figuratively or literally.

"That I am," she smiled as she spoke. "Lang, your next assignment is to face my desk and bend over. I need to know, though, are you experienced in this position?"

"To be honest, not at all, Miss Libbey," I answered truthfully. "I hope I live up to your expectation, though." I was having far too much fun playing this little game with her, and I knew she was, too. I turned around just as instructed and leaned over her desk, resting myself on my forearms.

"We'll start slow then," she said in a surprisingly gentle voice. I heard a drawer open and saw her flicking open a bottle of lubricant as I looked over my shoulder. I briefly wondered why she kept that in her desk. "Can you spread your legs a little more for me?" As had been the trend tonight I did as Gloria said. A moment later I felt a cool sensation on my anus as she rubbed a lubed finger against it. It was yet another new sensation that I found myself liking. I heard the bottle sputter as Gloria squirted a generous amount of additional lube on her finger and my asshole. "We're going in, Lang," she announced just before working her index finger inside of me. I let out a slight gasp, but there was no pain. She continued inward till I felt her knuckles hit my taint. She stopped there momentarily, then placed her other hand on the small of my back. It felt oddly comforting. I wasn't able to consider that much further though as my boss began withdrawing her finger from my ass before pushing it back in. She began a slow rhythm in and out of my me as she gently caressed the small of my back with her free hand. The whole situation felt surprisingly comfortable. So much so that I found myself leaning forward on my arms, closing my eyes and releasing a deep sigh.

A fairly sharp slap on my ass forced my eyes open. I threw my head around to see what Gloria's problem was. She caught my eyes with her own.

"You're going to want to be awake for this part, I'm adding number two," she announced. I simply nodded. Her hand left my back and I heard the bottle sputter again as she added more lube. "Here we go," she called just before her second hand returned to my back. A moment later she withdrew her finger till just the tip remained, then I felt a second finger join the first. She again pushed in. I let out a sharp hiss. She was definitely opening me up farther. After a little while her knuckles again came to rest against my skin. "Is this alright?" she asked. I faced her and saw that she was genuinely concerned that I was OK with what was going on. I nodded. "OK, I'm going to continue then." True to her words she began to fuck my ass with her fingers. After taking a few deep breaths I relaxed and suddenly it became much easier. "That's it," she said, "you're loosening up good. Are you ready for number three?"

"Yes ma'am"

"Good, good." She didn't warn me this time, she simply added her ring finger to the other two already in my ass. Again I felt stretched, but surprisingly the third finger was easier for me to take than the second. "I see a lot of potential for you in this position, Lang."

"I'm proud to have lived up to your standard, Miss Libbey," I replied, playing the game we were both enjoying so much. "I think I'm ready for the next stage of your assignment."

"You're showing great promise," Gloria replied. "If you think you're ready then I'm inclined to agree." With that she pulled her fingers out of my asshole. "I must warn you though, the next part of your assignment involves a steep learning curve." She punctuated her statement by dropping her large penis onto me. It came to rest in the crevice of my ass. "I have great confidence in you though, Lang. If you can fully accept my... instruction... shall we say, I'm sure the both of us will reap immensurable benefits." She was really stretching the metaphor here, but I was far too invested in the game to care in the slightest.

"I'll do my best, Miss Libbey. Give me your instruction, I'm ready." I felt her apply a fresh helping of lube to my anus, so I again craned my neck because I wanted to see what was about to happen as best as I could. What I saw was Gloria applying lube to the last seven or eight inches of her huge cock, using long slow strokes. I couldn't deny the way it glistened was beautiful. And that massive hunk of meat was about to go inside of me. She caught me looking and smiled.

"I have quite an attractive lesson plan, don't I?" she asked with a grin. 

"I'm looking forward to experiencing it, ma'am," I replied. At this point she'd finished lubing herself up. 

"And I'm eager to give it to you, Lang." I watched enthralled as she brought her left hand down and gripped my hip with it as best as she could. With her right hand she grabbed her womanhood about halfway up so there were maybe four or five inches exposed. She guided the head forward and soon I felt it pressing against my backdoor. "The first part of the lesson is the hardest to take, but I have confidence in you." With that Gloria leaned into me and I felt a great deal of pressure build up on my anus. Pressure turned to pain and I was sure I was going to fail, but to my surprise my asshole slowly began to open, accepting the head of my boss's penis.

"Oh fuck, that's a lot," I moaned. It hurt, but I was determined. Gloria stopped where she was though, as soon as I yelled out.

"Is it too much? I can stop," she offered.

At this point most of the head of her freakishly large penis was inside of my ass. I'm no quitter though. I looked over my shoulder and nodded to her. "It hurts, ma'am, but I can take it. please continue."

"You're a good employee, Lang. Taking one for the team is an important task." She leaned into me again as she finished her little speech and the effort forced the rest of the head of her cock into my ass. I grunted as it did, and with it a fresh blast of pain rocked my poor anus.

"Ugh... oh fuck, Miss Libbey, this really is a lot," I gasped, "Can you give me a little breather here before you continue?" My anus burned, but being stretched as I was added an unfamiliar sensation of pleasure to the pain. I absolutely wanted more of her inside me, just not quite yet.

"You've definitely earned it, Lang," she spoke with admiration. "Not a lot of men can take this sort of instruction." She began caressing my ass as she praised me. "I'm glad I had the opportunity to become your boss."

"Thank you, ma'am. I'm honored to work under you." We were really enjoying the game now. After this bit of chitchat I realized the pain had mostly subsided. "If you'd be so generous I think you can continue with the lesson plan."

"That's the kind of eagerness I like to see," Gloria pushed in another couple of inches and my anus swallowed them with relatively little pain. She then released the hold she had on her shaft, placing that hand on my other hip. At this point I only had a dull ache remaining and I knew I could deal with that. My boss was in position and I knew what was coming. "OK, Lang, it's time to continue." Instead of pushing in, though, she pulled back on my hips, drawing my asshole over her thick shaft inch by agonizing inch. I was breathing hard now and the pain had returned, although not as bad as when she first penetrated me. "You're taking this well, Lang, I'm nearly halfway in."

"Fuck, ma'am. That's a lot," I grunted as she continued working her way inside of me. "How much more could there possibly be?"

"Not a lot, Lang. Six, maybe seven inches," she informed me, "but I have the utmost confidence in your ability." Her praise was definitely working. I swear it hurt less knowing she felt that way. I didn't care that perhaps what she was saying was all part of the game. She said she was happy with my performance and I felt it. Suddenly I felt her drawing out so I looked over at her. "It's all part of the plan, Lang," she assured me as she pulled out till just the head remained, stopped for a moment, then slowly pushed back in. The inches sank in faster this time and felt so much nicer doing so than before.

"Oh wow," I cooed, "Miss Libbey that's starting to feel really good."

"Yes, it's supposed to, Lang," she replied, "all part of the plan, like I said." After getting a bit more than half way in she started to withdraw again. My anus was ablaze with pleasure now and as I focused on it I could literally feel the veins of her cock rubbing past my opening as she pulled out. She didn't wait this time, pushing straight back in once just the tip remained. I moaned in pleasure as she drove in again. She kept the same depth of fucking as she repeated the process several more times. Again she was pulling out, but this time instead of driving back in she stopped, just the head inside, as had been her pattern. I turned to look at her, wondering what the matter was. "This one's for all the marbles, Lang."

"Wha-" I began to ask what she meant but was cut short as Gloria gave one fierce thrust, "OHHHHH!!! FUCK!" In that one thrust she bottomed out in me, her hips hitting my asscheeks hard. I threw my head back and the pain returned a thousandfold, but with it came a wave of pleasure like I'd never felt before. And there she stayed, embedded in my intestines. Once the pain subsided, for the most part anyway, I looked over my shoulder again.

"Bet you'll never forget that lesson, will you?" She was grinning again but I couldn't be angry at her. She knew it hurt like a son of a bitch, but she also knew how good she just made me feel. "You ready for a proper fucking, Lang?"

"I honestly have no idea if I am, Miss Libbey, but I definitely want you to." She blew me a kiss before beginning to pull her massive cock back out of me. This time though she stopped half way and gave another sharp thrust. The pain and pleasure hit again, but it wasn't as intense as before. I grunted as her hips slapped my ass again. I turned forward and gripped my boss's desk tightly as she withdrew again. At the halfway point she again reversed direction and slammed her womanhood home. The hurt was fading now, but I could feel the pleasure radiating throughout my insides. She started pulling out again, this time well beyond the halfway point before driving right back into me. I found myself unable to resist the urge to moan. The pain was but a memory now, but the pleasure Gloria's cock was giving me was overwhelming. I lost count the number of times she'd thrust into me, but I was aware of the fact that she was pulling nearly all the way out now, just the head of her penis remaining wedged inside before she'd inevitably shove it forward, hitting pleasure points I never knew I had as she did. My cock was limp, which I'd later learn was an effect of getting it in the ass so hard, but I was pouring precum like a faucet despite that.

"We're nearly finished with your assignment, Lang." Her proclamation was followed by the hard slap of her hips hitting my ass yet again. "I just need you to take this deposit for me."

"Yes ma'am, I'm the man for the job," I responded between grunts and moans. "Give me your deposit. Every last drop." I think saying that really tickled her because she squeezed my hips tighter and somehow managed to start pounding my poor battered asshole even harder. My knees were weak now and I was barely able to breathe past the moaning. I slumped forward as Gloria pounded me for all she was worth. This new angle did something magical because all of a sudden I felt my cock twitch and the pleasure ratcheted up something fierce. I could only hold on as my body shuddered. Suddenly Gloria rammed herself as deep as she could into my ass and I felt the entire length of her cock twitch as she began to cum, pumping me full of her semen. I let out a decidedly unmasculine cry as  I was hit with an orgasm the likes of which I'd never experienced before. Since I was still flaccid, rather than shooting with any amount of force, the cum just leaked out of my cock and onto the floor of my boss's office as her massive penis simultaneously filled my asshole with its gargantuan load. I swear I could feel it burn as it flooded me, then I could feel nothing at all.

---

"Hey, you there?"

My eyes fluttered open as I turned towards the voice.

"Oh hey, you're back. We lost you there for a bit."

Gloria was looking at me with a bit of concern. That's when I realized I'd passed out from the fucking she'd given me.

"Y- yeah, I'm here," I responded. I could still feel her massive cockflesh buried deep in my ass. "How long was I gone?"

"Only a few moments, but I'd never quite seen anything like it before." Gloria leaned forward and gave me a light kiss. "How you feeling?"

"Amazing," I replied, "sore, but amazing."

"Oh yea, I suppose I should, uhh," she unceremoniously pulled herself out of me. Suddenly I felt very empty. "I, uh... I'm glad you were able to enjoy that."

"So am I," I replied. "I was skeptical, especially when it hurt so bad when you first pushed in, but wow did it ever get better." I straightened up and faced her. "That was really something else, uh... oooh." Being vertical again gravity was a factor now and I felt Gloria's semen start to seep out of my loose anus.

"Whoa, that's so fucking hot," Gloria gasped obscenely before shoving her hand between my legs and gently fingering my well used asshole. Her jizz made fine lube as she played around with me. After the fucking I'd experienced I expected what she was doing to hurt, but it didn't. I was left with nothing but pleasure. She did it for only a few moments before stopping. Once she pulled her fingers out of my asshole Gloria brought them to her lips and licked them clean as I watched excitedly. She then addressed me nonchalantly, as if what she'd just done was the most normal of actions. "We should probably clean this place up and get the hell out of here huh?"

"That's your call, Miss Libbey," I responded, "you are the boss, after all." We shared a hearty laugh at that before we got to cleaning.

~fin~

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