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Bending Over Backwards

Bending Over Backwards

Cassidy's first day as an intern turns into the most intense and kinky day of her life.
It had all started so well. Jessie had lent me that gorgeous mini dress and the matching killer heels for my first day as Melinda Thorpe’s intern, and I rushed to her office in excited giddiness. Every female student in my senior course wanted to intern for her. She was said to be incredibly strict and demanding, but she was also the queen of contracts in this town, the ruthless and beautiful mistress of business mergers and company syndication. Her face regularly decorated both business newspapers and fashion magazines. She was only in her early forties, but men and women ten years her senior tended to behave like school children with a crush around her.

My giddy steps came to a stop in an empty office. The desk was bare, nothing but the big monitor and the telephone giving away the fact that someone used to work here. I didn’t know what to do.

And then the phone rang, startling me, the sound loud and shrill in the empty office and tugging on my tense nerves. What was I supposed to do? I waited for half a minute, hoping the problem would go away, but when the persistent ringing didn’t let up, I crossed the few steps to the desk and hesitantly picked up the receiver.

“Cassidy Summers, this is Melinda Thorpe’s office, hello?”

“Where’s Melinda?” The male voice on the other end of the line was gruff.

I noticed with relief that the display on the phone listed an internal number. I had no idea what I would have told a client. “She’s not in yet. I only just arrived myself, Mister…”

“Shit!” he bellowed through the line. So much for appropriate choice of words in a business environment. “Bloomstein and Hardenberg are here, from BHP, and Melinda was supposed to get them to sign the contract.”

He paused, and I just listened, unsure what to do.

“Summers,” he finally continued, “you’re new?”

“Yes, I’m the new intern…”

I didn’t get to finish my introduction.

“Fetch April Carruthers, she’s the only other senior consultant in the house right now and have her deal with them.” His voice grew quieter. “I’ll have them set up in conference room twelve. Don’t let them wait too long.”

The busy signal ended our one-sided conversation and I stared at the receiver, my heart beating fast. Just who had that been? But then his order came back to my mind, and I hurriedly put the receiver down and hustled down the corridor, reading all the name plates as I went. I finally found the right office and knocked, but there was no reply. I opened the door and found her office equally deserted.

My heart started to throb in my chest. What to do? I stood there for a long minute, trying to come up with a plan. I didn’t know anyone else here, so I had no idea whom to ask.

Ask! I head to reach Mrs. Thorpe somehow. After rushing back to her office, I fumbled a bit with the phone, but I finally managed to open the built-in phonebook. R… S… T… There it was! Thorpe, Melinda - mobile. I quickly pushed the dial button and picked up the receiver.

I waited with bated breath for her to pick up on the other end, and I was about to put down the receiver again when I finally heard a crackling sound followed by a mumbled, “Yes?”

“Mrs. Thorpe? This is Cassidy Summers, your intern. I’m calling because…”

“Just a moment,” she interrupted me, and I could hear her voice from far away. “Yes, just like that. Oh god, that’s wonderful!” The next few words were muffled and I couldn’t understand them.

My breath hitched. Was she having sex while she talked on the phone? A massage, I decided, it was surely just a massage. Still, having one of those while she was supposed to meet with a client was not how imagined things should be.

“Continue!” Her voice was loud again.

“This is Cassidy…”

“I heard that already! Cut to the point.”

I felt like a fool. “Uhm, two people from BHP are here for the contract signing.” I was glad to remember the company’s name, even though their surnames had fled my mind already. “They are waiting in conference room twelve, but there’s nobody here to talk with them.”

“April can do it. She’ll be in the office at the other end of the corridor.”

“I looked there already, but she’s not in either.”

“Shit. Cheeky little bitch, I told her I might be late!”

“What shall I do, though?”

“I’ll be here in an hour. You go and entertain them. The final draft of the contract is in the left upper drawer of my desk, they can read through it already. There are three copies, read one yourself, and if you can answer any of their questions, all the better.”

“Okay,” I confirmed, though a bit meekly.

“What was your name?”

“Cassidy, Ma’am.”

“Good, at least you have manners. Listen closely, Cassidy! You fulfill every wish they have. If they want champagne, you bring them champagne. If they say jump, you jump. This is a big deal, and I won’t see it lost. You’re going to bend over backwards to make sure that they sign that paper, or at least wait for me in a good mood. If they aren’t here anymore when I arrive, don’t bother waiting around, just pack up and leave. Understood?”

“Yes, Ma’am.” My heart threatened to burst from my chest.

“Good. See you in an hour.”

I once more stared at the receiver. This day was playing out altogether different from what I had expected. I began to realize that all the stories I had heard about interns coming home crying after their first day were probably not exaggerated.

I pulled the contracts from the drawer and started to search for conference room twelve.


“You’re not Melinda.”

The words hit me with a verbal slap the moment I stepped my foot into the room. The two of them were seated next to each other on an expensive looking leather sofa with a low, dark wooden table in front of it. They were both, if I dared a guess, in their late forties.

He was tall and muscular, wearing black trousers and had the upper two buttons of his white shirt open. His hair, dark and neatly trimmed, was already beginning to thin and showed some streaks of grey. He was the one who had spoken, and a hint of annoyance danced in the corner of his mouth. His eyes were grey and calculating.

The woman next to him had a strong jaw and high cheekbones. The dark tan of her skin and the shiny black of her long, sleek hair hinted towards a southern European origin. She was almost as tall as her companion, and her wide shoulders and huge chest, with a lot of her impressive cleavage visible in the dark red satin dress, made her an imposing figure. Her dark eyes were focused on me, and I almost curtsied.

My heart played a drum solo. “I’m sorry,” I managed without too much stammering, “Mrs. Thorpe has unfortunately been delayed, but she will be here in an hour. I’ve brought the contract with me, so you can familiarize yourself with it, if you’d like.”

They took their time responding, but the male client finally stood up and extended his hand.

“I don’t believe we’ve met before.”

I bridged the few steps and shook his hand. “Cassidy Summers. I work for Mrs. Thorpe.”

“Jacob Bloomstein.” He didn’t let go of my hand, and his strong grip sent a strange tingle through my body. “I haven’t seen you before. I guess you’re new.”

Did his thumb just stroke the back of my hand or had I imagined that? “It’s the first day of my internship,” I blurted out and immediately bit my lip. Shit, I shouldn’t have said that!

Only a flicker of a smile showed that he had caught on to my dilemma. But I didn’t have time to worry about it, because the woman also rose from the sofa.

“Celestina Hardenberg.” Her grip was equally as strong, but what immediately captured my senses was the flowery, sweet perfume with the slightly bitter and intense footnote, matching both her dark, melodious voice and her sensuous but strong appearance. “It is nice to make your acquaintance, Cassidy.” Her voice had a breathless quality.

Something about her mesmerized me. “Likewise,” I managed to stammer awkwardly.

“It must be nice to work for Melinda, no?” This time I was sure that I didn’t imagine it. Her thumb flicked over the back of my hand, quick and softly like butterfly wings.

“It is,” I confirmed, “though I haven’t met her in person yet. I only started today, after all. But it is exciting…”

My voice trailed off when her amused smile and the raising of her eyebrow suddenly made me aware of the possible double entendre. The room seemed to become smaller.

“God, I’m rambling!”

“You ramble nicely.”

The way she smiled at me made my breath hitch, and I don’t know what would have happened if she hadn’t let go of my hand. It took me a moment to get back my bearings, but I remembered the contracts at last and handed both of them a copy.

“Thank you.” Mr. Bloomstein took it from my hand with a sly grin, and they both took their seats again.

“Can I bring you anything to drink? Or do you wish something else? Feel free to ask for whatever you desire.”

“Something to drink would be nice. Just a glass of water for me.” Mrs. Hardenberg smiled softly at me.

“I’ll take a nice, eighteen year old… whiskey.” The way he looked at me made it clear what he was alluding to. God, he was really hitting on me! They both were!

“Of course,” I hastily confirmed and bustled over to the liquor cabinet set into the wall. Thank god it had both, and I filled a big glass of water and a poured some of the golden whiskey into a smaller one, shielding my trembling hands with my body. Remembering my visit to one of the posh bars a few weeks ago, I also filled a small bowl with ice cubes and picked up the thongs to go with it.

I set the glasses down next the contracts they had opened on the table and acknowledged their thanks with a nod and a smile.

“I’m curious,” Mrs. Hardenberg suddenly said, “how you plan to keep us busy until Melinda arrives. From what I see, the contract is exactly how we asked her to word it, and both of our time is too expensive to waste it.”

I blushed. This was what I had feared. “If there’s anything…”

“There is.” It was him talking now. “But tell us, knowing Melinda, she has given you a set of directions to work with. What did she tell you?”

Shit. They were both leaning against the backrest now, their arms crossed and expectant grins on their faces. The room was quickly turning into a vortex that tried to suck me in. I couldn’t tell them, could I? But I watched Mrs. Hardenberg’s nails tap impatiently on her upper arm and knew that I had to start speaking. I bit my lip, but nothing but the truth came to the forefront of my panicked mind.

“She told me to fulfill your every wish. To jump if you say so. To bend over backwards to keep you entertained.”

My breath hitched audibly when I watched her run a finger along her cleavage while she licked her lips.

“Bending over backwards? What an interesting image.” She looked me up and down, and I did my best not to tremble from embarrassment. “I believe you would look exciting like that.”

I blushed, and my cheeks burned and tingled, as if my skin was growing too small for me.

Mr. Bloomstein chuckled. “Why don’t we start with something a bit easier than acrobatics, dear, perhaps something like undressing?”

“Oh god!” The words rushed out of my mouth before I could stop them, and my face flushed with the deepest crimson.

“What happens if we leave now?” She knew exactly what would happen.

My lips started to trembled. I waited for the ground to open up, swallow me and take me away from this place. It didn’t, and when the silence became palpable, my mouth confessed on its own. “I’ll be fired.”

“We would not want that, would we?” She asked her companion with mock concern, but her flustered face and gleaming eyes showed that she had me exactly where she wanted me.

“Oh, I’m not sure I care all that much,” he replied, his gaze locked to my face, “we can always get ourselves a pretty, willing intern if we so desire.”

The message was clear. God, I should be running away by now anyway. If there hadn’t been all that sexual tension already, I probably would have. But they both fascinated me in their own ways, and before I knew what I was doing, my trembling fingers nestled with the zipper of my dress.

My breathing grew shallow and the room appeared to spin around me, but I couldn’t deny the sudden wave of arousal that washed over me when I bent my shoulders slightly forward and let the dress tumble to the floor. I felt my nipples stiffen and a gentle heat build up between my legs.

“She’s pretty,” he commented, “but then, Melinda does only take on the prettiest.”

“You are a B-cup, no?” Her question was rhetorical, but I nodded nonetheless. “It is nice to see a pair natural tits for a change. I can understand the need to have them inflated to incredible proportions, but small ones like yours have their very own beauty. Be a dear and let us see them in the flesh!”

There was no turning back now. And by god, the hungry gleams they both had in their eyes made me tingle all over. I reached back and undid the clasp, then slowly pulled away the intricate black lace. My nipples stood proud and long. I had always been self-conscious about their length, and I never dared to go braless, because they were always so obvious through the fabric of a t-shirt.

“Magnificent,” she declared breathlessly.

My eyes widened when I saw her shamelessly stroke Mr. Bloomstein’s bulging crotch, and the certainty that this wouldn’t end once I was naked took my breath away.

“Come here,” she ordered softly, and I complied without hesitation.

Her hands, strong and skilled, stroked over my front side, and I my head tilted back on its own volition while a needful gasp escaped my throat. I had never been touched this way by a woman before, but the intensity of the moment made me lose all inhibitions. Sparks jumped from her fingers. It felt wonderful, and my body jerked when she touched my nipples.

“I wonder,” she murmured, but her companion cut into her sentence.

“Not yet, dear.”

“You are right, of course.”

And then her fingers picked up the waistband of my panties and she slowly drew them down my legs, exposing my shaven pussy that was glistening with moisture by now. I answered with a tiny, high-pitched whimper of embarrassment.

“Oh, how delicious. Step out of them, dear.”

I did, a bit awkward because of the high heels I wasn’t used to, but she finally held them up with a slight smile of triumph, before handing them over to Mr. Bloomstein.

“Knowing you, you will like to keep those as a memento, no?”

I trembled in my nakedness, arousal and embarrassment warring for dominance, but I managed a quick “No!” of protest at losing the panties Jessie had lent me.

“Do not worry,” she soothed, and I did stop doing so because her hand came to rest on my heated pussy, “we will buy you a new set if you are a good girl today.”

Her fingers started to rub back and forth, and my hungry snatch met her motions halfway. A slight slurping sound accompanied every movement, and I blushed even more. I had never been this wet before.

“You are going to be a good little intern, no?” Sarcasm coated her voice, but I didn’t mind.

“Yes, oh god yes!”

“Sit down on the table, dear.” It was his voice, filled with barely contained lust. “It is time to take you up on your offer.”

“Take me up? How?” I stammered even while my bum met the cool wood of the table, my mind in too much excited turmoil to wonder when the contracts and glasses had been put away.

His hands pushed down on my thighs and he looked hard into my eyes. “It’s time to bend over backwards, my dear!”

Mrs. Hardenberg had stepped behind me and softly guided my shoulders down on the table. My head dangled over the edge. My legs were pushed wide apart, and I realized what the lewd display was meant for.

“You’re going to…” I couldn’t voice the word.

“We will,” he confirmed, already having opened his shirt’s buttons and slipping it off, exposing a muscled, hairless chest, “like I said, we aren’t here to waste time.”

I trembled. He looked good. Fuck, he looked delicious.

Fabric rustled behind me as well, and I looked back to see her breasts look even more impressive, held up by an expensive-looking, blood-red half bra. But something made no sense. She pushed down her panties, and my breathing stopped for a moment. A huge cock, veined and stiff and with a shiny, purple head sprang free of its confines.

“But…” I stammered.

“Surprise!” She grinned down at me, judging my reaction.

I had heard of transsexuals and shemales, of course, but I had never in my wildest dreams imagined meeting one - much less getting intimate. Still, with all her femininity, something also looked incredibly right, and the glimmering passion in her eyes made me forget all about any natural order of things. Her tall, strong body, her forceful jawline and her shapely thighs - all that made complete sense now.

“One more thing, before we begin.” Her voice was throaty.

She bent forward and her cock dangled right above my face, rigid and mouth-watering. A light pain shot through my nipples and I gasped when I looked up. She had attached two tiny, golden bells to them with small, toothed clamps, and when her fingers let go they started to tinkle audible with every little movement.

“Oh god,” I whispered in a bout of lucid panic, “what if anybody hears and comes in?”

“We don’t mind.” It was him.

And when he pressed the tip of his cock against my pussy, guided the silken tip through the wetness between my lips and circled it around my already engorged clit, I wasn’t sure if I minded either.

“Oh god!” I groaned once more, “Yes, fuck me!”

He didn’t need to be told twice. He pushed his manhood inside me, slowly but without relenting, and drew whimpers of incredulous pleasure from my throat.

My vision darkened and something hot and smooth touched my lips. Her cock. She had knelt down in front of my head, and this had brought the stiff organ to the perfect height. I wondered for a second if the height of the table was truly coincidental, but then she tapped my lips again and I opened my mouth to welcome her cock.

The one in my pussy was picking up a steady rhythm. In, then a short pause, then out again, and each thrust seemed to touch deeper inside me.

Hers soon found a matching pattern and glid velvety over my wet lips, as if they had done this a thousand times before. They probably had.

The tinkling of the bells filled the room and was joined by their combined moans, my own lustful gasps muffled by the hot, throbbing flesh that slid in and out of my mouth, coated with a shiny sheen of my saliva. My whole body was awash with pleasure, and every time the cock speared my pussy and pushed its walls apart, fresh torrents of lust shook me. My vision was filled with her balls, thick and long, shaking with every thrust, and with tanned, strong thighs.

Suddenly I was lifted upwards, his cock still buried deep inside me while hers slipped from my lips. I got a bit dizzy from the sudden movement, and when I got my bearings back, he was reclining on the edge of the sofa and I was sitting astride his pelvis with bent knees.

He pulled me close and kissed me hungrily, his tongue entering my mouth and exploring every corner, spreading a taste of mint and whiskey. I twirled my own tongue around his and tickled it, drawing a pleasured moan from him, a tiny victory in my submission.

My body suddenly stiffened, and I let out a meow of protest. Something pressed at my pucker. A finger? No, bigger? My eyes widened, but he kept my head where it was with gentle pressure and continued to kiss me.

“Remember, whatever we desire.” Her whisper tickled my ear. “Relax!”

I did my best to do so, breathless with outraged, exhilarating lust. And for the first time in my life something that wasn’t a fever thermometer slid up my bum. It felt incredible and dirty when my tiny muscle stretched with slight twinges of pain to accommodate her huge organ. Deeper and deeper it slid into me, slippery with my saliva and spearing me relentlessly. My thighs started to tremble.

“Good girl.” Her voice shook with excitement.

I couldn’t believe when I felt her pelvis touched my bum. She was all the way inside me, I was stretched to my limits in both openings, and I could even feel both of their cocks press against each other through the small sheen of flesh. My breath hitched in a staccato pattern.

And then she fucked me, slowly and steadily, and colored spots started to dance in front of me. My body was wracked with tremors, and I jerked and writhed between them.

He never stopped kissing me, and the dance of our tongues became a duel of sorts, faster and greedier with every surge of arousal. We grunted and moaned into each other’s mouth, and behind me, she moaned as well.

I could do nothing but take the fucking, let myself get filled up to the rim with fleshy, steel-hard cock. I was feeling like the biggest slut in the world. It was glorious.

A hand squeezed my tits roughly. A finger pressed down on my clit. It was as if lightning was striking in all those spots, and my loins exploded with pleasure. My whole body jerked, and I felt my bum filled with a long, hard thrust before both cocks pulsed inside me and spurted their cum into my body.

I felt like flying. It was wonderful. All three of us trembled and jerked in the throes of our passion, prolonging each other’s climax, and it was like we were a single, orgasmic entity.

We were sweaty and breathless when we came down from our blissful high. I whimpered in disappointment when first one, then the other cock was pulled from me.


Clapping sounded from somewhere across the room, and my head swiveled around in shock. It was Melinda Thorpe! My boss, beautiful and elegant in her dark business dress. My heart hammered in my chest. How much had she seen?

“Well done, my dear!” She stepped closer while the other two sat down on the left and right side of the sofa and pulled me into their middle.

“You’re the first intern in a long time to pass that test.”

“Test?” My voice shook.

“Test. To see if you have what it takes to make a business deal at any price. I don’t waste my time with weaklings.”

Oh my god! “So you’re - when you make a deal - you…” I couldn’t say it.

I didn’t need to. “I don’t partake myself in our - incentives,” she winked, “that often anymore, that’s what April is here for. But she’s growing too old by now. Our clients want fresh, young flesh.”

“Flesh?” It hurt. “I’m flesh?”

“Hey, hey, no need to get hysteric.” She sat down on the table in front of me, right where I had been earlier, and I realized that a puddle of my juices had to be right under her bum. If there was, she didn’t let on. “I only take on the best. You’ve just proven that you are among the best. And you have to admit,” her hand stroked up my thigh and made my breath shudder, “that you have some very nice flesh on you. But tell me, would you have pleased Celestina here just as well if she had had a pussy instead of a cock?”

My face felt as if on fire. “Yes,” I stammered.

“Then show me.” Her skirt fell away and I was pulled from the sofa and to my knees.

She pushed her panties to the side, and I got my first close-up view of a pussy, clean-shaven and swollen, small pink strips of velvety skin peeking out between her outer lips. I extended my tongue and ran it through her folds, tasting slightly tangy but also sweet aroma.

“Yes,” she whispered softly above me, “I had a feeling you would be the one. Yes, just like that! Oh god, that’s wonderful!” I had a déjà vu, but I couldn’t care less.


I was able to shorten my last year at university by half. Sleeping with all your professors obviously came with rewards. Even gay Professor Edwards couldn’t resist my bum. Hell, he came back twice for more. And I quickly became the best-paid intern in town, because I worked on commission. Melinda hired me full-time the day I graduated. After a year, I was able to pick my own clients.

I thought my initiation had been the peak of kink. I quickly learned otherwise. But welts healed well on my body, and Jacob and Celestina’s company, Bloomstein-Hardenberg Pharmaceutics, had incredible remedies to cure stretched and chafed body tissue. I learned to suckle toes and kiss bum holes, to have my nipples clamped and my tits slapped, and I took whole fists in both of my openings. In short, it was glorious. So much better than sitting in front of a computer all day and typing stupid figures, like most of my coeds did.

Every new deal was exciting, and I wouldn’t have traded the depraved, guilty pleasure I got just from looking at the signatures for anything else.

A soft cough drew me from my memories. Melinda grinned at me from across our office, knowing too well how my perverted brain worked.

“You can give my feet a tongue bath,” she declared, kicking off her heels and extending her legs with a sigh, “then we’ll watch the video of your last performance, and if your persuasion techniques are still up to par, I’ll allow you to bum-fuck the new intern with the big strap-on you like so much. How does that sound, Cassidy?”

“Brilliant,” I quipped, closing the file I was working on before crawling across the carpet to her, “you know how much I love working for you, Melinda.”

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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