Prison Fling

by Cassandra Dee

  And we were caught in a loop. The more semen into my mouth, the harder I swallowed. The harder I swallowed, the harder the alpha pushed his fingers into my cunt, making me cream even more. And then my mouth sucked even more ferociously, milking the man of every last drop of cum.

  It was the best feedback loop ever, the most enticing, arousing situation I’ve ever been in. Because the truth is, I’ve never really touched a man. Nor have I ever let any man touch me, even though they tried. It’s just something that’s never appealed, with the boys gangly and nervous, their breath stinking of garbage.

  But this was a different situation. A different circumstance, pressed into service by a gorgeous, magnetic billionaire. We were on a private charter flight high in the clouds, our privacy guaranteed by his money and power. No one would interrupt us. If the man wanted to throw me into the back room and shove that massive cock into my steaming pussy, there wouldn’t be a peep of protest.

  And the thing is, I would have said yes. If he told the pilot to fly over the Atlantic, extending this flight by another ten hours, I would have said yes. I would have watched as Mr. Dawson locked the door on the private cabin and took me ten ways until Sunday.

  But the seatbelt light had already come on. Damien’s cock, though still firm, was merely dribbling into my mouth now, instead of spurting hot lashes of juice. And my cunt, though still horny and wet, was merely quivering on his fingers instead of clamping hard with every scream.

  The billionaire leaned back in his chair, pulling his hand from my secret space with a obscene wet squelch. Oh god oh god. Even the sounds were so disgusting, yet erotic all the same. Oh god.

  And slowly, I lifted my eyes to meet his, lips slightly parted.

  “There’s a gob of cum on your tongue,” he rasped, eyeing my flushed face. “I’d swallow that before we land.”

  Cheeks going bright red, my mouth snapped shut and I swallowed hard, the gooey liquid disappearing, before scrambling back into my dress. How did I look? With flying hands, I patted my curls into place, straightening the canvas fabric of my apron while stepping back into those high heels. What kind of stewardess wore four inch stilettos, the arch so high that my bust was thrown forwards, hips pulled back? Well, now I knew why.

  And never dropping my gaze, Mr. Dawson tucked himself back in, pulling his blazer forwards to hide the slight wet spot at his crotch.

  “You were great,” he said casually, eyes looking over my heaving form. “Just perfect. I’ll tell them to make a note in your file.”

  And dumbly, my chin nodded.

  “Thank you sir,” came my trembling voice. “Thank you.”

  Turning on my heel, I walked unsteadily back to the front of the plane, disappearing behind the partition where the stewardess’s jump seat was hidden. And only after I was buckled safely, did I let myself breathe deep for the first time in hours. Because had that really happened? Had I just sucked a handsome man’s cock hungrily, letting him stroke my pussy until it creamed deliciously? Had I really gulped every last drop of sperm like an adoring slut, letting Mr. Dawson use my body any way he saw fit?

  And in the dimly lit corner, my pussy pulsed its answer. Because yes, it’d happened. The alpha had taken over my senses with his filthy ways, his unerring air of command. And it’d been so good and so amazing … that I only wanted to do it again.

  CHAPTER TWO

  Joanie

  Drying my hair in the spacious bathroom of my Dallas hotel room, I stared at my reflection. The big brown eyes, the flushed cheeks.

  Was that really me?

  The girl with the curly brown hair and curvaceous form?

  Could anybody tell I was different?

  I guess on the outside, things looked the same. But on the inside, my mind and body were absolutely changed.

  Because I’d done it.

  I’d enjoyed a man’s cock on a private flight, creaming and mewling as he stroked my clit. I’d come all over his hand as he spurted into my mouth, pouring liters of hot man milk down my throat.

  And even now, I could taste that tangy semen. The unmistakable salty taste as I slurped, welcoming the hot fluid into my insides.

  How would it feel in another part of me? Dripping from my pussy cavern? Or pulsing into my ass?

  WHAT?

  My cheeks flared, mouth opening into a shocked O. Because how could I think this? How could I have these dirty thoughts? It was wrong. So, so wrong. This wasn’t the Joanie I knew at all. And yet my imagination went wild, every and any fantasy suddenly up for grabs. Mr. Dawson’s fingers in my sweet channel as I cried out, clutching those big shoulders. His massive cock burrowing deep into my pretty pink place. That giant cock in my ass, slow and steady as I cried out, resisting the stretch.

  Oh god. When did I get so dirty? I’ve seen porn, I admit, on my laptop. But that’s TV. Those are paid actors and actresses, who are acting out fantasies, figments of the imagination. By contrast, this was real. I was a newbie flight attendant working for a private charter company. The situation was totally different. So what was going on?

  But staring at myself once more, I knew it wasn’t going to stop. Because if Mr. Dawson wanted me again, I’d be there. I’d do anything he asked, willingly letting him use my body, to caress and stroke anywhere he wanted, seven miles up in the sky.

  But would I ever see him again?

  Would he even remember me?

  That was the worst part about this whole scenario.

  As a sex-positive woman, there was no shame in my actions. I’ve been taught to own my sexuality, to be proud of my choices. It was the other things instead. Like the surprise ten thousand dollar deposit from Elite Air in my bank account today, labeled “Bonus Pay.” How I had no idea if and when I’d ever see Damien again. Because we weren’t dating. We weren’t friends. The billionaire was a paying customer.

  And the truth made my heart seize painfully.

  Because is this what Elite Air did? Was this why I had a generous compensation package, a full fifty thousand dollars more than the commercial airlines? Was that the reason for the “surprise bonus” in my bank account?

  It was crazy.

  But somehow, I suspected it was true.

  Which meant that the filthiness might not end.

  Was I ready?

  Could it be happening?

  And tentatively, I delved deep, examining my heart of hearts. Because I’ve had a boring life. High school had been dull, and good grades weren’t exactly my thing. I was a shy mouse most days, hiding my figure behind baggy, unflattering clothes, with just one or two close friends.

  But now, the world had cracked open wide.

  There was opportunity at my fingertips.

  The chance to see the world.

  And shamefully, the chance to meet more men.

  Powerful billionaires all. Handsome. Charismatic. Dominating.

  Is that what I wanted?

  Unable to compute, I got into the king size bed, pulling the fluffy comforter over my head. There were too many thoughts in my brain, swirling fitfully, making me toss and turn.

  And the next day, when I woke up, a groan escaped my lips.

  Because there were dark circles under my eyes. Nothing a little concealer wouldn’t fix, but still. Appearance is very much part of my job, and there was no sense in looking pasty and gaunt.

  So quickly, I hopped in the shower and spruced up, dabbing some extra blush on my cheeks. I’ve never been a make-up person, but a perky and professional demeanor was important.

  And bustling through my routine, I got ready in a flash. Good. It was a new day, and I couldn’t be wasting time thinking pointless thoughts. This was a job.

  Stepping onto the G6, I busied myself prepping the plane for my next passenger’s arrival. Don’t think about Mr. Dawson anymore, a stern voice sounded in my head. That’s over and done with.

  So taking a deep breath, my eyes glanced at the manifest. Hmm, only one passenger again. My head shook. Man, these guys had to be Ki
ng Midas if they were able to afford riding alone in such a fancy plane. Such wealth had been unimaginable to me even yesterday, but evidently there were multiple men who had vast fortunes at their fingertips.

  But then my eyes squinted because the name Charlie Childs sounded a little familiar. Hmmm. Taking out my phone, I did a quick search and my eyes widened. Seemed that Charlie Childs was a cosmetics mogul. He ran a billion dollar conglomerate selling everything from nail polish remover to high end perfume. Man, this guy was rolling in dough.

  And from the pictures on my phone, he was gorgeous too. Tall, dark and handsome with movie-star good looks, always a gorgeous woman or two hanging off his arm. The girls were always svelte and perfectly made up, not a hair out of place. Quite the contrast to my own plump form and unruly curls.

  But right. This was a job. Real-life, not the movies.

  And as steps sounded, I pulled myself upright with a smile to greet my new passenger. And suddenly Mr. Childs loomed in the entryway, massive and huge. Unlike Mr. Dawson, he actually acknowledged my presence.

  “Hello,” came that deep growl, blue eyes taking in everything in half a second. Oh god, how many beautiful women he must encounter in his job every day? Top models, Oscar-winning actresses, all dying to promote his products.

  But somehow that gaze was warm and non-judgmental.

  “I’ll show myself to my seat,” he said with a grin. “No one on this ride but me.”

  I nodded quickly.

  “Of course Mr. Childs,” was my stammer. “I’ll be by momentarily with your nuts and champagne.”

  And once we leveled out on our way to Chicago, my hands sprang to work. Out came the small dish of nuts and the tall flute of champagne. Was Mr. Childs going to ask that I serve the almonds on my breasts, like Mr. Dawson? Oh god, oh god. My face flushed, breasts heaving a bit. Because I was ready if he asked. This man was so dark and gorgeous, that anything was possible.

  And wobbling a little in my high heels, I made my way down the aisle.

  “Here you go sir,” was my murmur, leaning over to place the welcome tray on his table. “Welcome aboard, Mr. Childs. I’m Joanie and I’ll be your flight attendant for this trip. I’ve brought you warm nuts, a bit of bubbly, and the day’s newspaper.”

  The dark man leaned back, surveying my form from the jaunty cap on my head to the polished navy blue stilettos.

  “Thank you,” was his reply. “Have you been with us long?” he asked.

  “No sir,” came my dulcet voice. “Just since yesterday.”

  “Ah, yesterday,” rumbled the man, a twinkle in those blue eyes. “Mr. Dawson sang your praises,” he added. “Damien couldn’t have said better things.”

  I flushed.

  “You-you know Mr. Dawson?” came my low voice. “I didn’t realize.”

  Charlie Childs smiled so that his eyes crinkled at the corners, those white teeth perfect.

  “We all know each other,” he said smoothly. “Elite Air was created by a group of us. Guys who wanted to fly private all the time. So we pitched in the for the expense, sharing the costs and benefits. A plane like this goes for fifty g’s,” he said with a wicked smile.

  Fifty g’s?

  That meant fifty million right? Not fifty thousand?

  That smile grew wider, Mr. Childs reading my mind.

  “That’s right, sweetheart. A plane like this costs fifty million dollars, so we split the price tag. Not that I don’t have my own.”

  My mouth dropped open once more.

  “You-you have your own plane, in addition to this one?”

  The alpha threw his head back and laughed.

  “Oh yeah. It’s good to have back-up you know? If one isn’t available for whatever reason, I can always turn to my spare.”

  I swallowed heavily again. The billionaire talked about planes like other people talk about cars. Except this was a fifty million dollar toy, not exactly something you park in your garage.

  “I see,” was my low murmur. “I see.”

  And Mr. Childs smiled again.

  “From your encounter with Damien yesterday, he said you’re very flexible.”

  My head snapped up.

  “I’m sorry?” was my gasp. “Wh-what does that mean?”

  “It means that you’re a good girl,” Mr. Childs rumbled. “Because I like to see everything.”

  “Everything?” I echoed in a whisper.

  “Everything,” he said silkily. “Now everything off.”

  I stood stock still for a moment, not believing my ears. But as those blue eyes roved over my form, my insides went hot and loose once more, nipples pebbling as a low ache settled in my belly. Because we were gearing up for round two, and suddenly I wanted it.

  “Everything,” Mr. Childs rasped once more. “Now.”

  And with that, my hand went to the navy blue hat.

  “No not that,” he corrected. “Let’s leave your hat and heels on. But take everything else off,” that deep voice commanded.

  And slowly, I obeyed. The zip on the back of my dress slithered down, material pooling at my ankles. Like before, I had on no bra, so my girls immediately burst free, creamy with pink tips. But my hands paused at my hips, toying with the sides of the little g-string.

  “Everything sir?” I whispered. “Everything?”

  At the moment, I wore nothing but the hat and high heels, plus this tiny scrap of lace over my secret spot.

  Mr. Childs was relentless.

  “Take it off, sweetheart,” he commanded. “I like my girls bare.”

  And what could I do? Slowly, my fingers rolled the fabric over my hips and down my thighs. But that’s when things got nasty. Because as the material descended, a long strand of pussy cum connected the crotch of the panties to my cunt, evidence of my need.

  “Oh!” I gasped, cheeks flushing red. “Oh!”

  But Mr. Childs was on it. With one big finger he leaned forwards and broke the strand, lifting it to his lips.

  “Tastes good, sweetheart. I’m glad you want me just as much as I want you.”

  Because by now, his cock was out. Oh yeah, that massive fuckrod stood straight at attention, pointing my way. And my pussy melted at the sight, more goo dripping out, a rivulet sliding hotly down one thigh.

  “Yes,” I whispered, hungry brown eyes meeting his. “Yes.”

  But Mr. Childs isn’t a guy that can be rushed.

  “Champagne,” he commanded.

  What? What was I supposed to do? But with trembling fingers, I handed him the flute, every nerve waiting with anticipation.

  “Come here, sweetheart,” he beckoned. I moved closer to him, the space between us disappearing.

  “Closer,” he rasped again. And this time, I moved even closer, so that my nude, lush form was merely inches from that big body seated in the white leather chair.

  The dark man smiled at me then.

  “I can smell your cunt,” he rasped. “It’s dying for dick. But sweetheart, I’m gonna make you feel good another way. You think you can handle it? You think this curvy bod can take what I’m about to give?”

  Wordlessly, I nodded, every nerve quivering, juice streaming down my thighs now.

  “Yes, Mr. Childs,” I whispered obediently. “Yes, I’ll try.”

  “Good,” he ground out. “Because I want to suckle this sweet, meaty cunt flavored with champagne.”

  And dipping his fingers into the flute, he lifted them, dripping with golden fizz. And then slowly, he leaned forwards to paint the champagne over my clit, stroking my throbbing nub and making circles around the pleasure point.”

  “Oh!” I gasped, knees going weak. My hands gripped the back of his chair to stay upright. “Oh god!”

  “That’s it,” Mr. Childs rasped, his eyes never leaving my juicing pussy. “That’s it sweetheart.”

  And he dipped his finger in again, this time painting the golden liquid all over my folds. He stroked my outer labia, getting them soaking, before using two fingers to pull my lips
apart, showing the gleaming ruby red within.

  “So beautiful,” he breathed approvingly. “You’re sopping wet baby.”

  Because of course I was. I was standing before a gorgeous billionaire, letting him play with my cunt. Not only that, but he was painting my private parts with champagne, smoothing fizzy all over my sensitive lips, and now, even into my interior.

  “Oh,” I moaned, throwing my head back, white knuckles gripping the leather seat tighter. “Oh god, I’m gonna come.”

  “Not yet,” he rasped. “Because we’re not even halfway there yet.”

  And the man leaned forward then, placing his tongue against my sensitive spot. Slyly, those lips nibbled at my clit, jolts of pleasure going straight from pussy to spine, making me stiffen slightly.

  “Oh!” came my helpless mewl. “Oh oh!”

  “That’s right,” Mr. Childs murmured from between my folds. “I’m gonna eat this all up.”

  And with that, he began in earnest. The alpha suckled my clit before biting at it, and then running circles around the stiff nub. And then he held my folds open and traced every sensitive crevice, every beautiful crease of my creaming pussy.

  “Oh!” I shrieked this time. “Oh god!”

  And it was so good that I almost fainted. But Mr. Childs gave no quarter. Because he kept kissing and licking and slurping, tasting my insides as female cream mixed with the champagne covering his mouth.

  “Tastes good,” he muttered into my pussy. “Tastes real good.”

  I thought I’d burst at that very moment. But then the man lifted his dark head, blue eyes gleaming.

  “You know what would make this taste even better?”

  I couldn’t’ answer, my breath coming in labored pants. He merely smiled again, chin slick with my wetness.

  “Your puss would taste even better if there was some cum in the mix. Champagne and cum. You think you can handle that?”

  And wordlessly, I’d stared at him, the heaving of my breasts my only answer. Because was this really going to happen? How would it work?

  But Mr. Childs has all the answers. Reaching one big hand down, he stroked his cock slowly, easing out a heavy trickle of pre-cum. And then with the wetness on his hands, he painted my clit again, making me mewl and arch my back with pleasure.