Prison Fling

by Cassandra Dee

  Helena nodded efficiently, noting something on her clipboard off-screen.

  “Of course,” she said, voice calm. “Of course, I’ll have that couriered to you right away. And our customers appreciate your precautions, Joanie. Usually, we don’t let the girls on board unless they’re using contraception, but we needed someone to start immediately. So you’re an exception.”

  My mouth opened, unable to speak. Clearly, Elite Air had a system going. They knew exactly how to prime and prep the girls for their dirty job.

  And soul numb, I clicked off my phone. That hadn’t worked at all. I’d called Helena, seeking solace and comfort. Much use that’d been. The woman was an emotionless robot, someone who knew her priorities. Because she was there to serve the billionaires, not me. She was on their payroll, and not mine.

  So my one ally hadn’t turned out to be an ally at all. I was completely alone, the whir of the A/C my only companion.

  And with slow steps, I heaved myself up from the bed and into the bathroom. A ghost stared back at me from the mirror. Curls wild and tumbled, brown eyes so big they almost took up my entire face.

  But there was something different for sure. It was the knowing look in my eyes. I’d been transformed by my experiences, pushed into womanhood with one sweet thrust of a man’s cock. Or four mens’ cocks, if I was being honest.

  And slowly, I parted my legs. Oh yes. My thighs were sticky still, pussy lips moist and swollen even now, hours after the encounter with the twins. With a slow hand, I reached down and stroked over the cakey whiteness. Their cum. My own juices. The fluids mixed so that it formed a tantalizing brew, flaking off slightly now.

  Slowly, my hand cranked the water to the shower, hot steam immediately filling the en suite. But I couldn’t make myself get in. That was the truth. Because I couldn’t bear to wipe off the sticky sperm, the mark of Andrew and Aaron. It shouldn’t have been like this. I should have been dousing myself with hot water, scrubbing hard, trying to get myself clean. For my emotional health, not to mention physical hygiene.

  But somehow, I couldn’t get myself to step into the stall. Instead, my fingers kept playing between my legs, stroking through my folds again, imagining the four men.

  Damien.

  Charlie.

  Andrew.

  Aaron.

  Yes, yes, yes. Touch me again. And right there, in the hotel bathroom, it happened. With one finger smoothing my clit, and another eased into my hole, I came all over again. Four cocks, in my mouth, in my hands, between my breasts. Deep in my private hole, and soon my back hole as well.

  A jolt ran through my spine.

  Because I wasn’t supposed to want this. I wasn’t supposed to give myself to the ecstasy, to anticipate whatever dirty acts would come next.

  And yet, here I was, stroking my curves, dreaming about the four men. Coming hard on my hands, pretending it was their cocks in my puss. Imagining the cum flying once more, hot sperm filling my inner cavity with goopy, satisfying warmth.

  Oh yes.

  That call with Helena had been pointless, not to mention totally unnecessary.

  Because I wasn’t going to lie to myself anymore.

  I wanted it.

  I wanted to engage with the billionaires over and over again.

  Unprotected.

  Hard. Hot. Heavy.

  Their sperm in all my chambers, making me feel good.

  And screaming in the bathroom, my cries reverberated, loud like a banshee. But these weren’t screams of distress or agony. These were the screams of a girl who wanted it all.

  Because how many more passengers were there?

  How many alpha billionaires would use my body, beckoning me to the dark side?

  And shamefully, I wanted it.

  But there shouldn’t be shame. I’m an independent woman, making a buck on my own time. Who’s to say that what I’m doing is wrong?

  And with that, I collapsed, gasping and panting on the floor of the bathroom, curves spilling everywhere. Because it was too good. Mindblowingly amazing, every nerve alive. And my mind was made up. This was my life, and I wanted to live it to the max, for as long as I was welcome. How long would that be? Another month? Another three months? Even a year?

  But there were no more tears. Instead, there was only the daze of fulfillment. The knowledge that I’d made the right choice, even if it was entirely internal. Because being a virgin doesn’t mean that I’m dumb. The opposite. It made me sensitive to the newness of the experience, endowing me the ability to see with fresh eyes.

  So I was here now, a stewardess with Elite Air. And my future unfolded, steamy and hot, filled with twists and surprises. What would it bring? Who knew? The only difference was me, aware and vibrant, heated yet knowing. Because I couldn’t wait to meet my next passenger.

  CHAPTER FIVE

  Joanie

  Showing up the next day, there was a bounce to my step.

  “Chipper eh?” asked Martin, the baggage guy.

  I waved cheerily.

  “A good night’s sleep will do that,” was my reply as I clattered up the metal steps to the plane. “Lots of zzz’s.”

  Martin just shook his head, swinging some expensive luggage into the hold below.

  But as I prepped the nuts and champagne, no one showed up. Weird. There was definitely a passenger, their suitcase was already here. So where was our missing billionaire?

  Suddenly, footsteps sounded on the metal rungs, a cheerful whistle lilting in my ears.

  “Captain Tanning,” greeted Martin from below. “Good to see you again sir.”

  A deep male voice sounded.

  “Good to see you too,” he replied. “We’ll be taking off in, oh, about five minutes. Just give me some time to get settled in.”

  And then the captain appeared. I did my usual perfunctory nod, but then stopped mid-way. Because this man was gorgeous. Tall, at least six four, that dark head almost brushing the ceiling. Incredibly bright blue eyes twinkled my way. Were they natural? Or was it colored contacts? But as he smiled, I realized there was no way this guy was wearing colored contacts. Because those eyes danced with humor, the sparkle real.

  “I’m Captain Tanning,” he said, holding out a hand.

  I took it, blushing a little. This is just the pilot, came my internal voice. Get yourself together. He’s probably going to hear all the moans going on once the plane’s taken off.

  So smiling a little nervously, I took his hand.

  “Nice to meet you Captain,” came my stilted voice. Oh god, why did I sound so weird? So I tried to be professional and business-like. “Estimated take-off time is in five, but our passenger hasn’t shown yet,” I said, shooting a worried look at the clock on the wall. “What should we do? Should I radio the control tower and see if they know where he is? I’m not even sure what to say because the manifest doesn’t list his name,” was my admission.

  But Tanning’s smile grew even wider.

  “Naw, no need to do that. I’m the passenger,” he said, that Crest-white grin dazzling to behold. “A couple years back, I got my commercial pilot’s license, so we’re taking this baby ourselves.”

  I gaped at him.

  “You’re the passenger?” I stammered.

  The gorgeous man smiled again.

  “Aye-aye mate,” was his reply. “Headed to Tucson today for a business meeting, flying is what keeps me sane, you know? Some of those meetings go on for hours, you’ve got to have ways to release the stress.”

  I immediately liked Tom Tanning. Not only was he insanely handsome, but the guy had a sense of humor as well. He was lighthearted, the type of guy who probably never fell into a depression.

  “All aboard,” he grinned again. “Now if you’ll just let me get this bird in the sky.”

  And with that, the door to the plane closed. It was just me and him in the G6, the cabin empty. But I was in good hands because Captain Tanning was all business then. Pulling on the headset, those blue eyes narrowed and focused, calm
hands guiding the G6 as it nosed its way out of the hangar. And before I knew it, we were up in the sky, cruising the blue highway with nary a care in the world.

  But I was here for a job. So with trembling hands, I put together the welcome tray. Nuts and champagne, as always.

  “Mr. Tanning. I mean, Captain Tanning,” I stumbled nervously. “Can I offer you champagne and almonds?”

  The man glanced sideways at me, showing that smile again.

  “Naw sweetheart, no drinking on the job. Maybe a glass of water though. Could you?”

  Immediately I nodded.

  “Of course sir. Happy to.”

  And in a minute, I was back, a tall glass of water in my hand.

  “Here you go sir, I’ll just place it here,” I said, indicating a small console in the middle.

  “Not there,” he interrupted, big hand covering on mine. Oh god, it was so warm, his strength reassuring. “Over here,” he nodded to his left side. “Don’t want to get water on some important controls.”

  I stared at him a little before jolting into action. Because to put the water down, I was going to have to reach across Captain Tanning. That’s right, I was going to have to brush my boobies across that massive chest in this small space, we were practically going to be glued together. But this is what the job’s about right? And shamefully, my insides melted a little, gooey stickiness trailing between my thighs.

  But there was no more time for shame. No more time for regrets. Because I’d made a vow to myself. This is what I wanted, and I was going to own it. No more lies, no more half-truths. I’m a woman who loves her body, embracing the unknown. And that unknown was now.

  So purring a little, I leaned across the man slowly, the vee of my dress dipping low and revealing the shadows within.

  “Here you go,” was my coy murmur. “Here you go, big guy.”

  And oh shit, but as I pulled back, one large hand snaked into the drop of my décolletage.

  “Hmm, seems you’re getting the hang of it, aren’t you pretty girl?” asked Mr. Tanning. “The other guys loved you.”

  I colored. Because clearly, the billionaires talked. But I was beyond that now. I was going to own this situation.

  So instead, I just smiled again as one big hand stroked a nipple in my dress, the aching pink stiff and nubby.

  “I’m so glad I did a good job,” was my throaty purr. “When my customers are happy, then I’m happy.”

  Those blue eyes gleamed.

  “I don’t think it’d be too much to say that you’re the best we’ve ever had,” rumbled the alpha, his smile like a wolf now. “And I mean the best.”

  The blush was immediate. Holy cow, I was number one? How was that possible? I was a virgin just yesterday, unpracticed and shy. Plus, these guys have had dozens of women, the most beautiful and desirable ladies in the world dying to date billionaire CEOs.

  But Mr. Tanning merely smiled again.

  “It’s not about flashy looks or perfect hair,” he ground out. “It’s about a sweetness and innocence, plus a beautifully curvy body. And you have that in spades. Now what do you say sweetheart? You want to show me that body?”

  I was ready for this. So standing up, slowly, I pulled the back zip to my dress down, the fabric pooling at my feet. And today, I’d worn soft, slippery black lace lingerie.

  “Shit,” the pilot rasped, eyes roving over my figure, eating everything up. “Shit, shit, shit.”

  My coo was immediate.

  “But how do we do this?” was my innocent smile. “You’re flying the plane. You can’t just up and leave.”

  Mr. Tanning’s smile was wolfish.

  “Haven’t you heard of autopilot sweetheart? You just flick a switch here,” he said demonstrating, “and then we’re good to go.”

  I gasped. Of course. These planes can practically fly themselves now, especially one as high-tech as the Gulfstream G650. Heck, they were even talking about self-driving trucks these days, massive machines that would trundle along our great country’s highways without a driver. So autopilot was absolutely an option.

  But Mr. Tanning’s eyes gleamed again.

  “The plane will fly itself baby, but that doesn’t mean I can leave the cockpit. Someone’s still gotta be here to monitor things, so that means you and I will be getting’ down here.”

  I nodded, cheeks blushing. There wasn’t a lot of room, but that’s okay. By now, the tent at his crotch was enormous, and I wanted a peek. More than a peek. I wanted to feel something in my snatch again, huge and full. My pussy was so hungry and that man meat was just the thing. Oh god, how did things get like this? When did I become such a creaming slut?

  But my head shook again. This was the new me. The new Joanie, who was assertive and confident. So cocking one hip to the side, I purred at the man. Literally purred.

  “How do you want it then, big boy? Where’s the hot seat?”

  That while smile flashed again, blue eyes gleaming.

  “Well before we get to that, sweetheart, first things first. You know I have a job to do. Auto-pilot is one thing, but you can’t just go totally hands off. I’ve got to keep the speakers on and keep in contact with flight control.”

  I nodded, a little confused.

  “Sure,” was my whispered reply. “Of course.”

  Did he not think I was sexy? Why was Mr. Tanning pulling back all of a sudden? But the billionaire nodded to a bag in the corner.

  “Reach in there and get out the gag, will you?” he asked casually, like he was requesting a glass of water. “The one that’s black and cock-shaped.”

  Now my mouth really did fall open.

  “Wh-what?” was my stammer, face going red. “The what?”

  His grin was careless.

  “The cock-shaped gag,” he said. “You know to keep you quiet when you scream.”

  That’s what I thought. I stared for a moment longer, luscious curves heaving. But there was no denying it. So with trembling hands, I reached to the black flight bag and pulled it open. Oh shit, oh shit! This wasn’t a normal knapsack with a laptop, an iPad and maybe a book or two. This was a bag of horrors, straight out of a fetish store. My eyes took in a leather colored whip of some sort, the strands tied together neatly, as well as an assortment of dildos, and even a couple butt plugs.

  “Oh my god,” was my involuntary gasp, hands trembling on the nylon straps. “Oh my god.”

  But Mr. Tanning wasn’t fazed at all.

  “It pays to be prepared,” was his drawl. “They taught us that in flight school.”

  My eyes snapped up to meet his, brown clashing with blue. But Mr. Tanning just flashed that million dollar smile again.

  “That’s right sweetheart,” he rasped. “Now get the gag out. There’s only one in there, you can’t miss it.”

  And with fumbling fingers, I obeyed, pulling out the black leather strap with a tiny two-inch dildo attached to the front. Oh god, how did this thing work? But it was all too clear. The dildo would pass between my lips, teeth biting into the soft rubber, as the leather straps fastened around my head. Oh god, oh god. This was so wrong.

  But Mr. Tanning couldn’t be denied.

  “These things are great,” he rumbled, fingering the black leather thoughtfully, one big thumb rubbing against that small shaft. “They work perfect when you’ve got a screamer. Come here, sweetheart. Let me put this on you.”

  And with slow, masterful hands, the alpha slipped the dildo between my lips, two inches of black rubber muffling my startled cry.

  “That’s what it’s there for,” he rumbled, eyes gleaming. “So you won’t make a peep as I fly this plane. The people in the control tower can hear, you know. Not this very second, but I can’t be on mute forever.”

  And with that, he fastened the metal buckles around my head, pushing my shoulders away to take in his handiwork.

  “Beautiful,” he complimented. “Perfect.”

  My brown eyes stared back at his. Because this was filthy, rolling in the gutte
r type dirty. I had a penis-shaped gag in my mouth, the tiny dildo stuffed in my throat. My curves were on display in the merest scraps of lace. And even worse? We were going to do it as he flew a plane.

  But Mr. Tanning was experienced.

  “Good sweetheart,” he rumbled. “Glad we got that settled. Now straddle me sweet girl, and let me play with that pussy.”

  Oh god, oh god. Yes, this is what I needed. So as he leaned back in the pilot’s seat, I threw one leg over his hips so that we faced once another.

  “Let’s get you out of this, hmm?” he asked, unfastening my bra.

  I could only nod wordlessly, the gag impeding my mouth.

  But no words were necessary because Mr. Tanning was already coasting, staring at the luscious curves that’d just been revealed.

  “Shit,” he rasped. “So beautiful. Let me taste.”

  And in a second, the man lowered his head to pull ravenously at one pink nipple.

  “Mmmph!” I squealed through the gag. Oh god, his tongue sent jolts straight from breast to cunt, making me moisten down below. “Unnf!”

  But the man wouldn’t let up. With another low growl, he reached between my legs and pulled those sopping panties to the side, baring my steaming cunt.

  “Gorgeous,” he rasped again, breaking from my breast to eye my swollen lips. “And dripping like fuck too.”

  Because this was a man who knew what he wanted. Mouthing my breast once more, he stroked my clit a bit before pinching that hard nub.

  “Mmmph!” I squealed furiously, struggling a bit in his lap. “Mmmph!”

  And at that moment, a voice crackled on his headset.

  “Everything okay there?” a woman’s worried tone sounded. “Everything okay, Captain Tanning?”

  My billionaire didn’t even bat an eye. Flipping the mouthpiece down, he spoke, smooth and casual.

  “A-okay ground control. Must have been static.”

  And then he flipped a switch and we were back on.

  “Does this pretty pussy want some finger?” he rasped, now licking my nipple as he finger fucked me below. “You want some hard fucking in this slutty cunt?”