Prison Fling

by Cassandra Dee

  “No prob,” I grunted, surveying the crowd. It was pretty packed already, people here for happy hour, talking loud and gesturing as three different football games played from three different flatscreens. Typical sports bar, fake wood paneling, harried servers scurrying about with heaping trays of fries and giant steins of beer.

  And at that moment, the bartender appeared.

  “Get you folks something?” he asked, face sweaty. I felt for the dude. Bartending during happy hour must be fucking stressful. Glad I didn’t have the job, since it probably only made minimum wage plus a couple tips.

  “IPA,” was my grunt. “Sam Adams.”

  The bartender nodded silently. “You?”

  Joanie bit her lip for a moment.

  “Just an iced tea please.”

  And the man nodded, gone in an instant.

  I turned to look at the brunette, brow raised.

  “Sweetheart, what’s with the iced tea?” I drawled. “You dry for some reason? What’s going on?”

  Joanie blushed, biting her lip again.

  “No, I’m not dry. Well, I am, but not by choice. Because I’m not twenty-one yet,” she confessed. “So I can’t drink legally.”

  Aw shit. I’d forgotten. We’re playing with an innocent teen, one who hasn’t even lived two decades yet. Fuck fuck fuck. By contrast, I was a forty-five year old hardened male, who’s been drinking since age fifteen. My cock twitched, entranced by her naiveté.

  “Sweetheart, I’m sure they wouldn’t card you here. Trust me, they’re too busy,” I said, looking around.

  “Maybe not,” the brunette acknowledged. “But I’d be so embarrassed if they did. Because when was the last time you were carded?” she asked. “Probably not in forever right?”

  Fuck, probably not in three decades. Because I’ve always looked older than my real age, huge and hulking by sixteen. So yeah, carding was a thing of the distant past.

  “They’ll serve me, I’m sure,” she said, smiling again. “But I just don’t want to risk it because getting carded would be too humiliating.”

  But I didn’t give a fuck if we broke the law. Hell, she could take sips of my beer if she wanted. And at that moment, the bartender reappeared, two long frosty glasses of amber liquid. The iced tea and IPA didn’t look so different, come to think of it.

  “Cheers sweetheart,” I growled, clinking glasses with her. “Bottoms up.”

  Joanie smiled back at me.

  “Cheers Mr. North. Thank you for making sure I had an amazing day,” she mewled sweetly.

  A lump formed in my throat even as I sipped at the beer. Because it’d been an amazing day for both of us. It’d been so long since I forgot my cares and just let go, enjoying what the city had to offer.

  But a bar is a bar, and lo and behold, the fucker on the stool next to Joanie turned then, eyeing that beautiful body.

  “Hey girl,” he rasped. “How goes?”

  Unbelievable. Did this douche not see me? Did he not see the massive male behind her, ready to beat his brain into a pulp?

  But the slimy jerk just wouldn’t stop, ignoring me though I was mere inches away. The city’s got so many guys like this one. Sleazy weasels, hair overly gelled with big biceps but chicken legs underneath. What a loser.

  But my girl is kind and she smiled back.

  “Hi, I’m Joanie. This is Nick,” she said, gesturing to me. My glower only got more ominous, but the weasel still wouldn’t make eye contact.

  “Hey, I’m Howard,” he said. “You new to town?”

  Joanie laughed, her perfect profile tipping back a bit.

  “I am,” she confessed. “How can you tell?”

  And this Howard dude went for it then. Leaning forward conspiratorially, he said, “The stars in your eyes chickadee. They shine like the sun.”

  I shook my head. This was so fucking stupid. His line was lame beyond belief, and I was tempted to rip off his head, right here, right now. But Joanie went along with it, and she laughed lightly again.

  “I see,” she said. “Well, nice talking to you Howard.”

  But the weasel just wouldn’t let go. He swiveled on his bar stool, eyes intent on that curvy form and started to talk on and on about sights to see in the City, where the get the best deals, where to get the best meals, spewing words like vomit.

  And lo and behold, Howard actually was a tour guide.

  “I run the Red Bus Company,” he proclaimed proudly, puffing up like a penguin. “You see those double decker red buses around town with sightseers sitting on the top level? That’s me. I give those tours, and sweetheart, I’d love to be your guide,” he said lowering his voice and winking lasciviously.

  This was so comical as to be ridiculous now. Because a real threat was one thing. But a penguin slash weasel slash professional tour guide? Please motherfucker. You have no idea how the big boys play.

  And with that, I did it. I’m a dirty asshole. Real nasty, with my mind in the gutter 24/7. So as Howard prattled on and on, his voice a monologue, I decided to mark my female. Oh yeah, right there in the crowded, darkened bar, I decided to brand this beautiful girl with my jizz.

  My hands rested lightly on her hips, scooching the female backwards on the stool a bit. The brunette turned to look at me inquisitively, but moved back a bit so that that big butt hung off the edge of the stool. Perfect.

  And with Harold’s voice buzzing like a chainsaw, slowly I placed two hands on her waist, grabbing the elastic of her sweatpants and inching them over her hips.

  Joanie’s eyes flew back to me, startled.

  “Wha-?” she said before fixing her gaze on Harold again. “I’m sorry, you were saying?”

  The man didn’t even notice. He was talking about his mom now, and how she brought him up to be discerning and perceptive. Yeah, right. Try again, motherfucker, because the girl before you is about to get fucked, and you don’t even know it.

  Because yeah, I was gonna do Joanie right here, right now, in public. It was dark in the bar, most people just shadowy shapes. It was crowded too, but we were way off to one side, the girl perched on the very last stool. So there was no one behind me. No one to see what I was about to do.

  And with slow, careful movements, I pulled the waistband of the sweats down so that her big ass was bared, the elastic stretched tight as it caught around her thighs. The front looked okay for sure, these were Men’s Size XXL so there was plenty of material. But the sight in back was fucking delicious.

  The peach was out.

  That beautiful butt, twin cheeks like moons, beckoning to me.

  And with another slow movement, I pulled her back even more on the stool before plucking that g-string out of her ass and moving it to the right.

  Oh shit.

  Fuck me.

  Because this was perfect.

  Joanie’s bottom hung over the edge of the stool, creamy and inviting. Again, from the front, she looked normal, chatting away with this Howard dude. But from the back, she was one hundred percent nude and full.

  That brown star beckoned, winking between her cheeks.

  Would she be able to?

  Would she be able to take cock up her butt in a crowded bar? While making conversation with a stranger?

  The brunette shot a panicked look at me over her shoulder before smiling again at the intruder.

  “Yes, Howard,” she murmured unsteadily. “Yes, I hear you.”

  I groaned, dick so stiff. Because with those words, she’d wiggled that ass a bit, sliding backwards so that her cheeks parted a smidge. Aw fuck yeah. That brown hole was on display now, baiting, winking and blinking flirtatiously.

  But what the fuck, we didn’t have any lube. So I used the only thing on hand. Reaching beneath her bottom, I stroked what I could of her pussy, the soft folds moist and wet. And as if on cue, the girl gushed into my palm, flooding me precious nectar.

  “Perfect,” I rumbled so that only she could hear. “You’re perfect, sweetheart.”

  And with that, t
he moisture was rubbed into her hole, Joanie struggling to hold still as I stroked her anus.

  “Calm, calm,” came my voice, sotto voce. “Calm.”

  Because shit, I had my cock out now, and if the girl saw this, she’d run screaming. Sure, I was big. I’ve always been big. But there’s big and there’s monstrous, and right now I was monstrous. Veins ran along the top and bottom of my shaft, pulsing with need. My glans gleamed purple, the shaft already coated with hot streaks of pre-cum.

  “Here goes baby,” I rumbled into her ear, breath blowing on that sweet cheek. “Here goes, right here, right now.”

  Because my head was pressing against that tight anus. Oh yeah, this was going down, anal sex in a crowded bar. Gripping her hips, I shifted that bottom a little, getting a better angle.

  And then it happened. Her rectum popped open and my shaft slid in a little. Fuck fuck fuck! Joanie was so tight, and the girl jolted a bit as my cock entered her ass.

  “I’m sorry Harold?” she gasped a little, leaning forwards slightly to improve my angle. “What did you say again?”

  Aw shit, my dick slid in a couple more inches then, hot and tight into that dry, arid rectum. Maintaining a neutral look on my face, I shot a quick glance at Harold.

  Because the poor loser was practically drooling, he was so excited to have a beautiful girl listening to his conversation. Not just listening, but replying too. Too bad he didn’t realize that she was getting buttfucked at the moment, my cock already halfway up her bottom.

  But he kept blabbering on and on about this and that, his two cats if I wasn’t mistaken. I have no idea. I was there but not there, every cell of my being focused on the sight of my huge fuckpole stuck halfway inside that beautiful rump.

  “I’m sorry Harold?” Joanie said breathily again. “Oh, ummm!” she cried out.

  Because I’d just pushed it in deep. That’s right, I slid ten inches of male power into her rectum and those walls squeezed me tight now, pulsing and clamping.

  “Oh ummm!” Joanie cried out again, breasts heaving, the color high in her cheeks.

  But it was too dark to tell. Not unless you knew what was going on. So Harold prattled on cluelessly about his two cats Mittens and Kittens. What the hell? What guy names his cats Mittens and Kittens? What alpha male has cats at all?

  But neither my girl nor I were really listening. Instead, we were both focused on where our bodies met, where my pole had begun a deep slide into her anal passage.

  “Oh!” she cried out again breathily. “Oh oh!”

  Meanwhile, I couldn’t keep completely silent either.

  “Fuck,” was my low growl. “Fuck you feel good.”

  Because this was so wrong. We were in the back of a darkened bar having anal sex. Yeah, my girl was sitting on a bar stool, chitchatting away with a stranger as I buttfucked her from behind, letting my pole slide in and out of her anus. It was fucking unbelievable.

  “Oh!” she cried out again, eyes rolling up so that the whites showed. “I’m sorry Harold, what did you say?”

  And it went on like that for a couple minutes. The girl squirming and squealing a bit, never so obvious as to raise any alarms. Me, hammering away from behind, trying to look nonchalant as my cock worked, coated in ass sweat and pre-cum. The situation was fucking unreal.

  But Joanie’s small. She’s real small, even after taking six guys in her bottom. Because after a few minutes, the sperm began boiling in my balls and I grabbed her hips, fingers pressing into that soft flesh.

  “Fuck,” I cursed softly into her ear. “Fuck fuck!”

  And that was it. Sperm jetted from my cockpole, blasting that sweet bottom with lash after lash of hot jism.

  “Fuck!” I swore again.

  Meanwhile, Joanie gave it up too. Her eyes went real wide for a moment, expression surprised, before the tidal wave crashed.

  “Oh!” she shrieked slightly. “Harold,” she panted. “What was that?”

  Hearing his name on her lips during an orgasm fucking sucked. It rubbed me the wrong way for sure. But there are some things you have to do because it kept the loser occupied, a dog responding to Pavlov’s bell.

  “So then I said this,” he prattled away, picking at a pimple on his chin. “And my mom said that,” he whined.

  Man, this guy was enough to stop an orgasm in its tracks, he was such a turn-off. But it was too late. We were beyond the point of no return and my dick jerked furiously, pumping reams of male semen into Joanie’s butt. The female milked me in turn, spasms rippling through her cunt and ass, squeezing me tight as jizz dripped between our bodies.

  Because there was a lot. I’m a guy who can pump liters on an average day, but this time it was gallons. Blast after blast hit the girl, spraying her rectum as her bottom clenched and clamped around me.

  But enough is enough. Because we were getting a couple weird stares now what with the tiny gyrations and small, helpless gasps. So maintaining a neutral expression, I pulled my cock slowly from her asshole, wet length still glistening and hard. Shit, it looked so good.

  But what we didn’t count on was the massive creampie. Because there’d been so much semen that the moment I was out, a sharp splat sounded on the floor. Fuck fuck fuck! It was like a mini-waterfall, a huge gush of white seed that dropped from her ass to splatter on the wooden planks.

  And unfortunately, Harold jerked awake then.

  “What is that?” he asked, staring at the floor beneath Joanie’s bar stool. “What the fuck is that?”

  It was only too obvious, the jizz bubbly and white, still steaming from her rectum.

  Joanie stammered.

  “It’s, it’s …,” she said, cheeks fire engine red.

  But I’d had enough of this. It was time to go.

  So passing one big hand over her anus, I caught the rest of the jism in my palm before yanking her sweatpants back up.

  “Come on sweetheart,” I rumbled, taking the brunette’s hand. “I already settled the bill, it’s time to go and do more sightseeing.”

  And with that, we swept out of the bar. So what if a couple people stared mystified at the wet spot on the floor? So what if there were some whispered looks as Joanie passed, a small splotch of dampness on her bottom?

  I didn’t care.

  I’d just had anal sex with my girl in public, pounding her as she talked to another guy.

  Nick 1. Harold 0.

  No strike that.

  Nick ten. Harold negative ten. Joanie twenty.

  Because what girl would let me do this? What girl would go out in NYC wearing loose sweats, only to let me fuck her anus as we sat in a bar? Only a sweet butt slut … and that luscious butt slut’s name was Joanie MacAllister, our perfect girl.

  CHAPTER NINE

  Andrew

  Oh shit. I’m gonna kill that motherfucker. And if I don’t kill him, then Aaron’s gonna finish the job.

  Because what the fuck? Joanie was supposed to be on a flight to Atlanta yesterday to meet us. It was our turn with the pretty brunette. It was our turn to enjoy her charms, to take turns stroking those beautiful curves.

  But she didn’t show.

  The plane flew down, sure, but it was empty.

  We were fucking livid.

  “What the hell?” my brother raged, storming about like an angry bull. “What the hell?”

  “You tell me,” I rasped. “Nick and Charlie brought her to New York yesterday. She’s supposed to be here today.”

  We cornered the pilot, a spindly, pasty-looking guy.

  “Where’s the girl?” I demanded. “Where’s your passenger? How the fuck did you take off without a passenger?”

  But the pilot’s hands shook, unfolding a raggedy manifest.

  “There are no passengers,” he stammered, showing us the piece of paper. “No passengers and no crew either. I thought it was weird, but the order came from Mr. North himself.”

  That explained it.

  That fucker Nick had done it. Charlie was probably back in Chic
ago already with no idea what had happened.

  Because Nick North is an asshole. Dude thinks he’s god because he’s from New York. He thinks the world revolves around him, but this isn’t how you play when dealing with other billionaires.

  Try again, cocksucker.

  You’re gonna regret it.

  Because we’re here now.

  As soon as my brother and I realized Joanie was missing, we hopped the plane. That’s right. Tom’s not the only one with a pilot’s license, so we commandeered the G6 and flew straight to JFK.

  This place sucks if you ask me.

  Crowded.

  Polluted.

  People everywhere, nothing like the gracious spread of Atlanta.

  But different strokes for different folks, and the city wasn’t what we were here to see.

  We were here to find our lost girl.

  What belonged to us.

  Taking our share, fair and square.

  So like criminals, Aaron and I lurked outside Nick’s door. It was lame. We’d managed to stroll into his building and come up the elevator, but he wasn’t home. Banging and even kicking the door did no good. It was solid oak with a dead bolt, resisting our frenzied attempts to break in.

  Yeah, my bro and I are ruthless.

  Who cares if there was a camera silently capturing every move?

  I swung around and gave it the finger for good measure.

  Because our female was missing, and we were here to get her back.

  Fuck this.

  But Nick and Joanie didn’t show. Nine p.m. passed, then ten. And just when we were about to head out, the elevator dinged, a low male voice mixing with tinkling female laughter.

  Sure enough, the doors swung open, and out stepped that motherfucker with Joanie on his arm. What the hell? Why was she wearing gray sweats, her face flushed and smiling while carrying a huge box of Candy? What was this? Howdy-Doody gone wrong?

  I growled, hackles rising.

  My bro did the same, two enormous sentinels baring their teeth at Nick North.

  Because what the fuck?

  There clearly hadn’t been an emergency. Nick had been squiring Joanie about all day, taking her to see the sights.