Risk Versus Reward Ch. 09

Author's Note

Risk Versus Reward is a prequel to Girl Friday and focuses on the story of Karin, the 'H.R. Lady' who provided Charlotte's rather unique interview experience when she was hired. You do not need to read Girl Friday to understand what's going on in Risk Versus Reward. But if you enjoy this story, Girl Friday should most definitely be on your reading list.

In the last chapter, Karin got to experience the joys of The Academy's own special version of home economics class as she was turned into a living appetizer tray under the direction of a slightly sauced Miss Chowdury. And while Karin was served up at the faculty luncheon she finds herself intrigued by an attractive woman she refers to only as Miss Spiced Latte. So intrigued in fact, she decides to offer her mystery woman a happy ending under the luncheon table. But what will become of Karin's chutzpah?

I hope you enjoy Karin's continuing story.

WaxPhilosophic

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Chapter 9: Spirits in the Night

Dinner that night was the usual weirdness. We were served a wonderful gourmet meal by the lovely lab-coated wait staff and the wine seemed to be available to us in endless supply. All we had to do to get the royal treatment was to follow the advice of the flat panel monitor that showed a cartoon girl pressing a rather uncomfortable-looking conical-shaped plug between her butt cheeks. The animation was especially amusing tonight in that it showed the poor girl in various stages of frustration and having to try again several times -- once with lube, another time by placing the plug on a bench and sitting down, and then finally with the help of a friendly cartoon girl sporting a lab coat and nitrile gloves.

If you've never sat down to dinner with a plug up your butt -- and really why anyone in their right mind would do that outside of The Academy's walls I don't know -- but you do sort of get used to it after a while. I'm no scientist, but I suppose that after being stretched long enough, the human sphincter muscle sort of adapts to the new reality and accepts the fact that things are indeed bigger on the inside. Add to that the wineglass that was never allowed to become completely empty, and except for when I shifted my posture I really didn't take much notice of the plug. I don't think any of the other girls paid it much mind either. Everyone seemed to be laughing and talking and enjoying the culinary delights presented to us.

I sat with Desi of course. We were nearly inseparable these days. But rather than being seated right up next to each other in sets of two, all of us girls sat along one of two long benches with plenty of elbow room factored in. Celia was on my other side, and nobody was tied at the wrist at the moment which definitely made it easier to enjoy our meal. Just a bunch of girls having a nice dinner while our butts got stretched. We talked about the classes we had this morning, and it's definitely Contemporary American Literature for me tomorrow, though a couple of the girls look positively enthralled as Desi and Celia recounted my luncheon experience in all of its harrowing detail. The way they talked it up I wouldn't be surprised if Miss Chowdhury had a full class tomorrow.

Desi and Celia also knocked back a fair share of wine as they gabbed, and though not quite as pickled as Miss Chowdhury was at ten in the morning, they did start to get a case of the wandering hands. As a result one or both of them would plunge a finger between my thighs or their own and then bring it up above the table to be presented to any one of us, or in some cases selfishly kept and savored alone. Soon they really got going and started likening it to the sorbet used to clear the palate between courses. Except with those two, the sorbet seemed to come with every third bite.

"What's with you Karin?" Celia teased. "You've been so somber since lunch. Miss Chowdhury wore you out, huh?"

I shrugged. I knew what it was and it wasn't Miss Chowdhury, that was just the warm-up, the introduction. The current source of my whoa was Miss Spiced Latte all dressed up in a white suit, but I wasn't about to tell these two characters. I'd never hear the end of it.

"She just needs another sorbet, that's all." Desi grinned as she and Celia both presented me with their fingers simultaneously.

"Thanks." I slurped them both off with a great smacking of lips and curling of tongue and that was enough to convince my two slightly obnoxious friends to leave me alone for a while. So every few minutes I would slurp at a juicy finger to let them know I was still here, but otherwise I let my mind turn inward to the woman I had met while cling-wrapped to a platter serving up appetizers.

Why was I so obsessed with her? She was fucking gorgeous, yes, but then that was pretty much the norm around here. It certainly wasn't her charming personality, she had barely said two words to me other than saying she was impressed by my chutzpah. I even had to look that up to find out what it meant. The dictionary seemed to imply it could have either a positive or negative connotation associated with it depending on how it was used. So when she said my shower performance had chutzpah was that a good thing? And when I decided to stuff my face between her thighs under the table was that chutzpah too, or was that simply bad manners?

The thought of her never left my mind that evening, nor did the nagging feeling that not all of my chutzpah was viewed as the good kind.

* * *

I had trouble sleeping that night, and was eventually awakened by a stirring and swishing of sheets in the big harem-style bed where I lay spooning Desi while she in turn held onto the diminutive Celia. Judging from the dim light and the many girls still slumbering I guessed the hour to be sometime just after bed, but not so late that the dawn would be creeping through the window at any time soon. I thought maybe I'd go have a pee since I was already awake.

I blinked and blinked again. I found that I was looking straight into the eyes of Headmistress Hendricks, and you know what? -- she was still wearing a pencil skirt, stockings and heels, even in the middle of the night. But she was also wearing a mask. It was one of those masquerade ball type masks all glittery and bedazzled, and the bottom of it rested right on her cheekbones, really only succeeding in covering the area directly around her eyes so it's not like she was hiding. Still it was enough to be a bit unnerving, particularly in the middle of the night when I thought I was just getting up to pee.

Headmistress Hendricks was flanked by two other figures also in masks, a half-face white one that reminded me a bit of the Phantom of the Opera and a second but much more sinister-looking one that was a straight out of a horror movie kind of scary. It even had horns twisting up from the top and I swear I heard a few bars of Toccata and Fugue running through my head in some sort of hyper-realistic auditory hallucination when I gazed upon it.

Once I stopped fixating on the masks I could see that in each one of Headmistress Hendricks' hands she held a strap. That made me nervous -- being immobilized at lunch was enough for me, thank you very much. Each strap was about two feet long and if I'm not mistaken they appeared to be made of black leather. I wasn't too sure about the details because the light was dim and I was slightly freaked out at this point, and that was entirely due to the other two masked figures. The two flanking apparitions in Headmistress Hendricks' entourage were even scarier in their attire, that besides the masks, included a couple of unmistakably large flesh-toned appendages dangling from about their waists.

"Des," I said, "I think we have visitors."

No sooner had the words crossed my lips than I felt a hand grasping my ankle and dragging me over to the edge of the bed. I found myself staring bug-eyed and open-mouthed right up at Headmistress Hendricks. I was wide awake at this point, my fight or flight instinct kicking into overdrive and if it weren't for the headmistress's words I honestly think I may have bolted for the door and run screaming all the way back home.

"Shh, Karin. It's alright," she said as she brought up one of the straps -- definitely leather, I could smell it as well as see it now -- and placed it over my eyes. She tied it around behind my head and stroked my hair a moment in an attempt to calm me further. It wasn't really working, because I still had a small sliver of sight where the strap didn't fully cover my left eye. And through that little crack I could see Desi with the strap being drawn tight between her lips before being secured around the back like mine.

And in my terror I had a vision of three monkeys, one with hands over its eyes, another covering its mouth and the third holding its ears. See no evil, that was me. Headmistress Hendricks had quickly realized her mistake and adjusted the blindfold so that I could see nothing but blackness now. That started me quivering anew because I could still hear, and what I heard was Desi -- speak no evil -- as she grunted and cried against her gag. I'm guessing that one of the masked figures flanking Headmistress Hendricks had just impaled my friend with that wicked-looking thing hanging between her legs. By this time I had also guessed that the hear no evil role was being played by the other harem girls with whom we shared our bed, because while Desi's mewling had reached a fever pitch, I don't think a single one of them moved a muscle, at least not that I could detect.

"Karin," Headmistress Hendricks intoned softly while stroking my hair, "you started something at lunch that you really should have kept your nose out of, so to speak. But since you were unable to control your urges, and you were also not able to satisfactorily finish the job ... well, let's just say you've let the genie out of the bottle and now she's here to collect. Hands and knees dear."

"Yes, Miss." I suspected I knew exactly who she was talking about, and when I caught a whiff of spiced latte I was sure. It was the mystery woman in the white suit, the woman whose legs I had stuck my face between regardless of the fact that she was wearing pants to signify she did not want my attentions under the table. And when I felt the tip of something large being pressed against my opening, I knew I was going to be paying for my actions tonight.

She presented me with an interesting dichotomy, my mysterious Miss Spiced Latte. She was gentle in that she filled me slowly rather than impaling me all at once as I suspected Desi had been, but she was also rather insistent on teaching me a lesson, because once she was in to the hilt she began to fuck me. She fucked me like I had never been fucked in my life. There was that one time with Billy Jonas, the star pole vaulter of the boys track team, I let him nail me while I was still riding high from our victory at the state championships, but that was more like masturbation for him with me just happening to be there to provide the friction. This though, this experience with Miss Spiced Latte was a true fucking, I know that now and I know what I've been missing out on.

I grunted and moaned as she filled me over and over, mercilessly driving me on toward first one orgasm and then another. The first one surprised me with its quickness and I wasn't quite sure it had actually happened, but the second one announced its presence after a good strong build-up and I roared and shook as it hit. I was sure I had attracted an audience by now, but I heard no applause like during my shower performance, in fact I heard nothing but Desi's continued mewling and panting as I assumed that she was being treated to a similar sort of lesson. Though for the life of me I could not think of what Desi's infraction might have been.

I had just sailed through my third orgasm and you may not believe this, but it was actually starting to think the next one would hurt. I didn't know if it was possible to die from too much coming, but I was a little afraid that I might be forced to find out this evening. I was shuddering and screaming into a pillow as I went over. And it did hurt, but it was also wonderful in a way and I welcomed the sensations, good and bad equally as I steeled myself for another. My arms had long since given out and if it weren't for my spiced latte infused goddess holding up my backside with her fingers digging into my hips I think I would have been a quivering puddle of useless flesh melting into the sheets. But right before I was sure I was about to die, I suddenly felt empty.

My goddess had pulled out. Every inch of that wicked appendage that had been battering my insides for what had to be the past hour or more, it was all suddenly gone. As rough as she had been with me I was a little sad that it was over. It was so incredibly intense, and I have to credit her with bringing me to the realization that I can be multi-orgasmic under the right set of circumstances. The fact that one of those circumstances happened to be long and thick and hanging between her legs was not lost on me.

"Let's see what else you can do," she leaned over my quivering body to whisper into my ear. "I don't think we've quite found the limits of your pleasure yet."

This is pleasure? I thought. I'm being impaled mercilessly for over an hour and then left in a heap, and this is pleasure?

But it was. It was mind-bending pleasure. Being woken up in the middle of the night to be blindfolded and fucked by some mysterious woman whose name I didn't even know was proving to be quite an exciting trip for me. So when I felt a cold splash of lube on my backdoor and that massive appendage being pressed up against it, I just sort of went with it. I raised my hips and pressed back until I felt the tip working its way inside while I silently thanked the lab coat girls for their help getting the butt plug situated before dinner and their insistence that I have a bidet before bed. I felt fuller than I have ever been and wanted nothing more than to expel that wicked thing before it tore me apart, but after a few deep breaths I eventually managed to regain some calm.

"Shh. Just relax my beautiful girl," My spiced latte goddess whispered to me. "You're going to love having me in your ass." After burying the thing in me to the hilt she stopped and just trailed her fingers over my lower back for a while, presumably to let me adjust which I was thankful for with all of the spasms and threats of cramping coming from down below. And after a while her tender words and caresses worked, because I started to relax. She started to move again after that -- slowly at first, but then picking up speed. I couldn't hear Desi anymore, so either she was done being used for the night or she had shuffled off this mortal coil and died of pleasure. I was beginning to think that an orgasmic death would be my fate as well. It felt good -- like really good -- but it was just more sensation on top of what already felt like it might have been too much.

"Ohhh," I started to moan as Miss Spiced Latte Goddess continued building in speed and intensity. She was more gentle than she had been with my poor pussy -- I was going to be sore for days I just knew it -- but other than being stretched and filled to my limits, this was not an altogether uncomfortable experience. It's almost if she wanted to make sure I enjoyed it. She kept right on trailing her fingers over my skin and praising me, calling me her beautiful girl and her wonderfully adventurous little kitten. I liked that name, Kitten, and as my eyes rolled back into my head I actually began purring while she continued filling my ass with a gentle insistence.

And it was good! I never would have believed it if someone had told me that it would feel so fucking good, but it did. Soon I felt the first quiver that was not due to the spasms of exhausted muscles. It began building in my core and I could feel my poor empty pussy clenching at nothing but air as the pleasure from that dildo buried inside me increased. But every time my pussy clenched my ass did too, and that doubled the wonderful sensations being dished out by the Goddess Miss Spiced Latte. She was the one, I knew it now. If this woman took me as her submissive like the way she took me tonight, I would be happy for the rest of my life. I would bathe her, and cook for her, and fetch her wine every evening when she walked through the door if she would but bestow upon me even half of the pleasures she was opening my eyes to tonight. Yes, I would be hers. Yes! Yes! Oh my goodness! I've got her dildo in my ass and I'm going to ...

And then she pulled out. The goddess left me hanging on the brink.

At that moment I let out something that was between a shriek and a whimper as I as ground my hips into the mattress of that big harem bed twitching and straining for release. Every muscle between my legs was cramping up at once and I squeezed my eyes against the pain. She was going to do it, she was going to let me suffer. I heard her snickering as she grabbed my hip and rolled me over to ensure that my orgasm stayed out of reach, that I couldn't grind myself to release.

"Karin is off limits tonight girls." It was Headmistress Hendricks. I had almost forgotten that she was still here, until she spoke. "She needs to learn a lesson in what it means to be left unfulfilled. So unless you want extra squat-thrust lessons for the rest of the week I suggest you leave her to suffer in solitude."

And in my frustrated state, I was left with two distinct thoughts vying for space inside my head -- Oh my goodness, that was the most amazingly intense pleasure I've experienced in my life, why does it have to end? and It was pretty bold of her not to at least ask first before dragging me over and fucking me within an inch of my life. I struggled with that last thought for a while. Yes, I had done something uninvited under the conference room table, but two wrongs don't necessarily make a right, do they? Was my leaving the goddess unfulfilled at lunchtime an automatic pass for her to have her way with me in the middle of the night? Is this what I was signing up for? Getting fucked whenever and however she felt like it? But in the end I couldn't deny how amazingly intense the whole experience had been and decided to overlook the issue of consent for the moment.

The blindfold was pulled from my eyes and I looked around to see my audience. The semi-circle of girls who had watched me being fucked right up to death's door and then left hanging. Not a single one of them uttered a word, but their faces said it all. They were mortified -- as shocked as I was at my rough treatment -- but at the same time they loved every minute of the show. Their pupils wavered and their mouths hung agape, salivating in anticipation of more. So when our masked tormentors departed and Desi and I remained huddled together shivering, the other girls engaged in an exclusive orgy of their own creation to relieve their collective need. I listened to their moans and watched them recreating some of the same techniques I had experienced firsthand by using their fingers on each other, while various places between my thighs twinged or spasmed with the recent memory. But after a while I settled down as my mind focused solely on my goddess who smelled slightly of spiced latte, my own personal tormentor this evening, and I felt a smile beginning to spread over my lips.

This may sound arrogant as hell, and it probably is, but I honestly think that the entire evening had been orchestrated for my benefit. The coincidence was just too good to be true. What are the chances that tonight's dinner appetizer would be buttplug a la lube, and that the wine kept flowing so readily, and that the lab coat girls practically dragged us through the bidet before sleeping. And a demonic companion just happened to show up to keep Desi occupied. Was it all so a certain woman with the presence of a goddess and the aroma of spiced latte could have her way with me, punishing me for an indiscretion, but at the same time not have to worry about shredding my virgin ass or having me soil the sheets?