Top Cat Challenge Top Cat strummed his chin and pondered the latest in a long line of monetary shortcomings. Same old story requiring a fresh new solution. The last raffle was a total bust, the last block party nearly got him arrested, and the bingo game only brought in five suckers just as poor as he was. Altogether nearly a weeks' worth of fleecing had only amounted to the single dime he was lazily flipping while he tried to think of a way to pull in bigger sums. Today the money wasn't the only thing on his mind though. No, as always, money was but a means to an end. In this case, that end was something he couldn't just swipe off the nearest grocer's counter; though admittedly not for lack of trying. Girls, man, the trouble it was to court them. Nowadays you couldn't fool 'em with flowers from the porch and a ten-cent box of chocolates. No, you had to wine and dine them properly, and none of them appreciated the skill it took to sneak into a movie anymore either. TC groaned and caught the coin harshly in his fist. Between the cost of a proper dinner and a show it almost seemed more economical to use less kosher means to relieve oneself. TC's eye's snapped open abruptly. "That's it!" he thought aloud, "No more dealing with tiny sums, just nice big cash payments. Yeah... it could work. Just need some girls..." With a smile and a kick, TC flipped the lid off the nearest trash can and gave it a walloping with a nearby stick. This was a job for the gang. After about three seconds too long, the usual suspects gathered side-by-side in front of their leader. TC started off with a headcount, of course, naming off Spook, Fancy, Choo Choo, Benny; everyone of 'em responded with a cheerful "Present!" or some variation of the sort. One fellow didn't respond in a timely enough manner for Top Cat's liking though? "Brain? Brain?! Okay where's the Brain? Anyone?" He glanced around to his posse but didn't get more than a shrug from any of the fellas he locked eyes with. When he dropped his gaze a foot and scanned again though, he caught a little blue cat raising his hand. "Benny, you have something to bring to the table?" "Yeah, TC, Brain's working today." "Working?! We're talking about earning a living and he's off wasting his time at a job?" Top Cat rolled his eyes and shook his head. "I swear what am I gonna do with you guys?" Thankfully, before they were forced into starting without him, the offending party dashed to the end of the lineup with a cheerful, "Uh, hey, TC. Sorry, I'm late-" TC cut off the inevitable excuse by rapping him between the ears with his stick. "Yeah, yeah, Brain, don't even bother. We got a real idea to make money working here." Fancy chimed in right away, sidling up to the can Top Cat was speaking from and leaning in excitedly, "Oh boy, TC, what's the latest gag? It's been a while since we had a good hustle." "I'm glad you're so excited, Fancy-Fancy, because you get to be a cornerstone of our newest enterprise." Top Cat gave his compatriot an affectionate pat on the head before turning back to the rest of the crew. "Now, men, tell me who here's gotten some physical companionship lately, of the womanly variety?" A chorus of hands shot up, with only Spook and Brain not responding immediately, and before Brain had finished considering the question, TC clarified. "And I mean beyond just a bit of heavy petting." All but Fancy's hands went down, and with a casual motion TC brought that one down as well while he leaned forward on the trashcan. "As you can see, I think we've got a service that's in quite high demand?" Top Cat took a moment to savor the doubt as his crew glanced at one another in confusion and concern. Another chorus of hands shot up after they'd been given a second to consider. He called on the first one he saw, his favorite pink cat sitting in the middle of the pack. After getting the go ahead with a nod, Choo Choo spoke up. "Just so we're clear TC, you're, uh, talking about escorts, right?" "Nah, Chooch, I like the word, but I think it might be a bit too classy for us. I'm talking about turning tricks." Choo Choo raised his hand again. This time he didn't wait for a go ahead though. "Question two: Don't we need girls for something like that?" Top Cat grinned and turned to the brown fellow next to him with a bit of a flourish of his head. Before he could propose step two of his plan, someone else from the back row cut him off. "Well, like, not necessarily, Choo Choo." Instantly all eyes, including TC's turned toward the speaker. Spook either didn't notice the eyes on him or didn't care, because he went right on ahead without the slightest alteration in tone. "Like, there are places where the guys aren't too picky, if you know what I mean." "What do ya' mean, Spook?" Benny asked with a big, na‹ve grin. "I mean, like, I know some guys who'll stick it in anything. And, like, everyone's gotta mouth, right, pops?" Spook shot TC a wink. Top Cat couldn't help but ponder the suggestion for a second, but that wink sparked something of an uncomfortable image in his mind. There Spook was, on all fours right in front of him with a mouthful cock. "O-oh!" Benny's sudden exclamation snapped Top Cat out of the fantasy and back to the alley, though TC also had to shake his head to properly wipe the image from his eyes. "That's what ya' mean." Back in reality, Top Cat surveyed his troops with just a hint of discomfort. Chooch and Benny had both gone rigid, evidently assaulted by the same thoughts he'd had, but Spook and Brain were both quite relaxed still. Brain was even nodding along with the idea, though the usual glazed look in his eye made his understanding of it questionable. That said, two that didn't need convincing and two he could probably convince without too much effort did strike Top Cat as good odds for a gamble. Plus, the boys certainly had some potential. Choo Choo he noted as probably the big seller, looking svelte enough to maybe even pull off a drag act. Then again, Spook had a certain relaxed appeal; a good sway to his hips. Then there was Fancy, lady killer that he was, Top Cat was certain he could lay down enough charm to swindle a few bucks outta someone. After his eyes had lingered a little too long on Brain to size him up too, TC shook his head, realizing he'd been checking out the goods. "What am I thinking?" He looked at Fancy beside him and noticed that he was still holding the guy's hand on top of everything, which, given the circumstances, was making him suddenly very uncomfortable. Slyly, he pulled the paw away and leaned forward on an elbow instead to address Spook. "Ahem! While I appreciate the forward-thinking approach, Spook, I think it might be best if we explored other avenues. Surely one of you fine fellows here knows a lady that would be up for a new business venture?" The crowd went silent remarkably quickly, and a quick glance made it apparent why. Chooch and Benny had gone from stiff to shrinking and were desperately avoiding eye contact. Spook and Fancy were too for that matter. So, Top Cat locked eyes with the one man still staring in his direction, even if it didn't look like he was doing so on purpose. "Uh, but wait just a second, TC," Brain mindlessly raised a paw as he spoke. "If we get a girl in, won't that mean we'll have to cut her in on the profit?" That was the final push TC needed to fully reconsider his initial plan. "Oh, Brain you beautiful, bee-yoo-ti-ful boy. You make a very good point." Top Cat's ears were ringing with the sound of cash registers as he realized the possibilities. He didn't even stop to consider what he'd just said. "Yeah, a girl would demand at least fifty percent, but with you boys all working and a generous sixty percent finders fee for your manager we might actually have something here." He pondered the idea more thoroughly for a moment, or at least pretended to with a paw to his chin. "Eh, but then again how much profit can we really make off of these guys." He shook his head dismissively. "Hey, I feel like I should be insulted." Choo Choo's response was momentarily passionate, but confusion set in a second later. "Then again, is guys not buyin' us a good thing?" Spook threw an arm around his pink friend while his guard was down. The effect was immediate, with Choo Choo stiffening right up again. "He's just, like, pulling your leg, Chooch. They'd be, like, all over you, for real." "Uh-huh... Th-thanks, Spook..." Top Cat just continued to shake his head. "Maybe we got the looks, but you guys just ain't up to snuff." He rolled his eyes and smiled. "Why I don't even want to think about how you take care of yourselves, let alone another fella." Despite his claims to the contrary though, TC did end up thinking about that very thing. The idea of a loyal harem tending to his every need. Even if it was the guys, it didn't look half-bad in his head. "It can't be that different from charming the ladies, right, TC?" An arm coyly wrapped around Top Cat's shoulder and Fancy leaned in close. He spoke with a big happy smile, but Top Cat did notice the grip was a fair bit snugger than a usual reverie at the bar. "I know my way around that forwards and backwards." Fancy finished with a very knowing wink, first to Top Cat, then to Spook. Spook took up the wink and took the floor. "And, like, if someone needs some extra tips I'd be, like, happy to show 'em how it's done." If what Fancy was doing counted as subtle, Spook was anything but. He pulled Chooch in nice and close, pushing their cheeks right up against eachother. Then his free hand went straight for Chooch's hip. "Uh, I think this might be g-getting a bit out of hand, guys." Chooch blushed and stuttered but didn't pull away. Even when Spook's paw slid around his hip and towards the front of his groin, all he did was shiver. "What're you sayin', Chooch. I, like, got it right in my palm." Spook made a point of groping Choo Choo then, holding his balls right, as he said, in the palm of his paw. It didn't take more than a second for the blood to rush from Chooch's face and right down to his dick, leaving him rigid and shocked smack dab in the middle of the alley. Embarrassingly, Top Cat wasn't terribly far behind, but he had the good fortune to mostly be concealed behind his podium for now. The only one that might have spotted it was Fancy, and his eyes were as locked on the show as the rest of 'em. Spook didn't slow down for a second either. He went straight from groping to stroking as soon as Chooch's dick had shown itself. And all eyes were on the shaft as Spook tugged Chooch's foreskin aggressively up and down. All eyes but Spook's anyhow. He was watching his friend's face the whole time, and just as the color started to make its way back to Chooch's cheeks, he leaned in to give the pink cat a kiss on the neck. "Uh! T-Top Cat!" "Don't shout for me, pal. Focus on the customer." Top Cat's fingers twitched as he continued to watch. He hardly noticed Fancy moving closer until the paw started sliding down his shoulder. He caught Fancy's hand just before it reached his hip. "Getting a little over-enthusiastic there, Fancy." "Just practicing, TC." Fancy gleefully responded by forcing his hand back against the hip. "Well practice somewhere else." Top Cat casually slapped the hand away and sidled away. "I'm, uh, supervising." He glanced back to the action and his eyes went wide. In the moment he'd been distracted, Spook had separated from Chooch and gotten on hands and knees in front of him, tail raised high seemingly just for him. Though that was put into doubt when he saw Spook's face, with eyes focused lazily on the dick hovering right in front of him. "Sure thing, TC." Fancy strutted into sight a moment later, lifting his own tail and proudly showing off his thick shaft half-cradled in one paw. This one was definitely for Top Cat though. Fancy confirmed as much with another wink before setting up beside Choo Choo. "C'mon, Chooch, let me show you a trick the fellas love." Fancy made a show of lifting his paw away from his cock with a noticeable glisten around the tips of his fingers. Then, just as Spook was wrapping his lips around Chooch's cock, he unceremoniously grabbed the pink cat's rear with a fierce squeeze. Choo Choo shouted, and his legs buckled. "F-Fancy? Spook? I-" He was cut off by another gasp as Fancy closed in behind him and gave his cheek another squeeze and spread it aside. Top cat was well around his trashcan and craning his neck for a good view at this point. He could get a great view of Spook easing his way slowly down more of Chooch's cock at an alarmingly quick rate. He couldn't make out any of what Fancy was doing though. "Benny, Brain, go get me a camera or somethin'. We're gonna need reference material." "C-can we get it later, TC?" Benny responded shakily as he spent his own time watching the goings-on from a seat nearby. A quick examination revealed a hand covering his privates and shaking with a few uncertain strokes. Brain was sitting right next to Benny, but he wasn't covering up, or even jerking for that matter. He was just sitting and watching, and it barely looked like he was even paying attention. The two things that made it clear he was were the dumb grin on his face and the absolutely massive hardon between his legs. It was at least as thick as Fancy's, and Top Cat could have sworn it was at least twice as long. Top Cat only realized he'd been staring at the thing a few seconds later when Fancy drew his attention away. "Now take it slow, Choochy, just sit down nice and gentle-like." When Top Cat turned to look, it started him to realize that he had gotten a better view of the action, having moved closer to Brain without even thinking. What the better view allowed him to see was what really threw him though. Fancy had taken a seat behind Choo Choo and had his cock aimed straight up at the ass above him. Choo Choo was crouching nervously some distance above it, shakily lowering himself before retreating hastily when he touched the tip. "I-it's not gonna hurt or nothin', right, fellas?" "Like, not if you, like, do it right, Chooch." Spook had mostly backed away for the moment to give Choo Choo some space. Now he was seated in front of his pink friend was a big, strangely casual smile as he watched. After Chooch hesitated a second more, he reached out and wrapped a paw around his friend's cock as casually as that smile would suggest. "But, like, we'll be right here if it does." Spook punctuated his encouragement with a little wink. Choo Choo nervously smiled right back and squatted again, this time only flinching a bit when his hole met Fancy's tip. Spook and Fancy reacted with a squeeze of Chooch's cock and a grope of his ass respectively. Fancy's grope moved up from the cheek the waist, then started to unsubtly pull the pink cat closer. There was a collective gasp in the alley when Fancy went in. Top Cat was knocked off his feet and wound up next to Benny, barely even keeping himself seated with his hands holding him up and his twitching cock fully exposed. Benny folded in on himself, leaning forward for a better view and pressing his hand even harder into his groin. The Brain didn't react quite as violently as his friends but began panting as he started to jerk his own shaft, finally. Choo Choo made the loudest noise though. While Fancy managed to keep himself to a respectable grunt, Chooch almost screamed. He stifled it to a muffle after closing his eyes and biting his lip though, blushing the whole time with embarrassment. His tail twitched aggressively, and Fancy continued to goad him down the shaft. Soon the entire head was sunk in, and Fancy let go of his cock to place the other hand on Chooch's hip. Another tug got another shout from their friend. "F-Fancy! It's t-too big!" Choo Choo leaned forward as if to escape but ended up stopped when his hand landed on Spook's shoulders. Spook looked him right in the eye with that casual smile. "Like, relax, man. You're gettin' the hang of it." He gave Choo Choo another wink, then his gaze went right to the dick in his hand. Top Cat followed those eyes to note Choo Choo's shaft, twitching and leaking like mad, coating Spook's wrist and paw in clear pre-cum. Spook had noticed long before TC, of course, but now he gave in to the temptation such a coating provided, licking his lips and leaning in to wrap his mouth around the shaft again. Choo Choo's legs nearly gave out and he threw himself back when he felt the Spook start sucking. This time Fancy stopped him just short of fully bottoming out, allowing the pink cat to slightly regain his footing just barely above his friend's groin. He followed through to the end a second later though. Chooch gripped Spook's shoulders tight and held in one final breath before his shaky knees let go altogether, and he kicked legs free to lay back against the brown cat behind him. The noise he made then was almost feral; a yowling sigh that came across as almost song-like. It drove TC absolutely crazy with desire when he heard it. "Wow, Choochy, you sure know how to sing," Fancy wiggled his hips and set his chin on Choo Choo's shoulder. "Now c'mon, baby, wiggle a little." Fancy gave Choo Choo's hips another squeeze and a push in time with the movement of his own hips. Chooch followed through with the suggestion, continuing to softly yowl as he shifted on top of Fancy's cock. Every now and again he would lift himself up an inch or so before dropping back down with another particularly sharp breath. "O-oh boy..." Benny froze for second, then broke into a violent quaking as he leaned forward. The little guy grimaced and panted as he came into the palm pressed into his crotch. Top Cat watched a variety of scrunched up expressions play across Benny's face before it settled on a weary panting. He chuckled as his mind and eyes wandered to his friend's groin, where Benny had finally relieved some pressure, allowing TC to see a sticky hand pulling away from a still pulsing, little dick. "Done already, Benny-boy? You didn't even get a turn at practice." "Ehehe." Benny blushed and smiled back at his friend. "That's okay, TC. I've been payin' close attention. Hehe." He shook his head and turned back to the trio, where that practice was rapidly approaching its own climax. TC was increasingly aware of his own need being neglected though, and he wasn't prepared to let it go ignored for much longer. He set a paw on Benny's shoulder. "Now that won't do at all. We need to get you some experience. He pointed to the trio. "So, how about it, what would you like to try first, old pal? I think I'm curious about what Spook's up to myself." Recognizing his name, Spook glanced up from the cock he was sucking and glanced up at Top Cat and Benny. His eyes lowered lazily for a second, and then TC noticed he swallowed. As if on cue, he pulled away from Chooch's groin, revealing the pink dick to be squirting a few dribbles of cum. A quick smile revealed a bit of that cum still shining on Spook's lips. "Like, someone need me, pops?" Spook spoke as casually as ever, even when the two cats began to moan passionately directly beside him. Benny twitched in Top Cat's grip, and TC realized he'd really put a squeeze on his friend's shoulder. Easing up for a second, he tried to respond to Spook with a casual smile of his own. "Uh, nah, Spook. I can see you've been working hard enough." Spook gave his lips a lick as Top Cat spoke. Benny and TC both shivered for a moment before he continued. "I was, uh, just about to help one of the other fella's practice." "Oh! Can I go, TC!" Brain leaned forward abruptly, drawing most of the gathered eyes his way. "I been watching close, so I think I can do it, and besides, uh," he smiled at Benny, "I ain't never been much for just doin' it alone either." Top Cat's brain flared for a moment when he remembered the size of the Brain's third leg, and he tried to ignore the twitch in his dick as the thought came to mind. Instead he stood up, asserting a bit of dominance as he strutted over to the orange cat. "I like the can-do attitude, Brain." He reached down and gave the simpleton a pat on the head. "Go ahead and show us everything Spook's taught ya'." TC shot him a wink, but if Brain noticed he didn't let on. "Uh, okay, TC." Brain crawled to a seat below his boss without a second thought. "So first you stand in front of me, kinda like that, yeah. Then, uh..." Brain set his hand on Top Cat's hips. They lingered there for a second while he pondered his next move. Something about the anticipation was working though. Top Cat felt some butterflies as he stared at Brain, biting his tongue and furrowing his brow. When the orange cat's face relaxed, the butterflies went into overtime. "Oh, yeah! Then, you sit down." Top Cat felt his knees buckle as he was jerked down with a forceful pull. He only barely managed to catch himself mid-squat by grabbing onto Brain's shoulders, and just in time too. He felt the tip of a dick poke the inner part of a cheek and grimaced. His tail began to spike and twitch wildly in response as he caught on to what had nearly happened. He chose to deliberately ignore the fact that his asshole was twitching alongside it. "Whoah, whoah, Brain! I think you might have forgotten something here." "Oh? Uh, what'd I forget, TC?" Before Top Cat could correct the Brain's mistake, he was given pause by Spook appearing on his knees right beside them. "Like, easy Brain, you just took it a little too fast." He turned to TC and set a paw on his knee. Then, without breaking eye contact, he lifted his paw and spat in it, allowing his tongue hang out and drool for a moment after before licking up his fingers. Without missing a beat, he then reached out and wrapped that paw around Brain's cock. "You, like, gotta lube it up first." Spook rubbed the cock gently but made no effort to keep it still. Top Cat winced when he felt Brain's tip slide across his hole, leaving a wet trail on top of it. He didn't move though, even when it passed by a second and third time. By this point he was willing to admit a curiosity. In fact, his only protest came when he noticed Brain was barely reacting to the treatment, just staring up at him blankly. "What's takin' so long, Spook?" He rolled his eyes before looking over to Spook. "I'm need to show the gang how it's done, already." "Like, relax, TC. There's a rhythm to these things." Spook chuckled and set the tip right by TC's hole again. Then he casually moved his hand up and played his wet fingers across that hole before sliding the hand back down Brain's cock. When Top Cat felt that, followed by a little push on his knee, he decided he wasn't gonna waste any more time. With a deep breath and a glare at Brain, he dropped his knees while Spook kept the cock steady. There was resistance at first, but TC forced his way right past that with an exhale. Pain was the first thing he felt, but that was gone quickly as everything in his body started to fire up at once. It was like heartburn after a big meal, and similarly, not only was he not regretting a second of the decision, he was somehow feeling even hungrier after the sensation. The tail betrayed any pain and energy with it's twitching, but TC's face only displayed frustration as he tried to push down further and get that sensation deeper into his body. He could only manage to get another inch deep on his own before he had to stop though, grunting and tossing his head back. "H-help me out a bit here, Brain." He pulled the orange cat closer and arched his back. That got him another bit deeper, and he continued to adjust more in hopes of further correction. Eventually he managed to hit that rhythm Spook was banging on about. Though, annoyingly, he had to pull up and let some go to get down deeper. Brain just stared on vacantly the whole time, first at Spook, then at TC. "Uh... h-how should I-?" "J-just push or somethin'." TC groaned as he got another inch in. There was a mix of terror and excitement as he tried to think of how many more there were to go. By now his asshole was totally on fire, but everything past that was humming with intensity. Top Cat only barely noticed when Brain's grip on his hips tightened again, but once he did everything in his head told him to stop what was coming. Even Spook was shaking his head next to them. He didn't say anything though, and Brain followed through with the threat those hands posed, pulling TC straight down and through all the uncomfortable spot. TC let him, throwing his own legs out from under him. He wanted to scream, but he couldn't breath for what felt like a solid minute. Everything in his body was shouting for him though. Top Cat's tail had gone entirely stiff and his face was locked in a violent grimace. Claws had even extended right into Brain's shirt, threatening to draw blood. The only part of TC that moved for a few seconds was his cock, which was spasming violently against Brain's stomach. Brain, meanwhile, had finally started to move. His body was shaking all over, and his legs started to kick out under his boss. His face scrunched up, and he started to blink like crazy, as if he was holding back a sneeze. "Uh- w-what now, TC." "Don't move a muscle, Brain, that's what." TC groaned and squeezed tightly on the monster inside him, using muscles he didn't even know he had. He tried to turn and look at Spook but didn't have much luck getting a response from any other muscles. "Spook, I can't feel my arms. Help me out." Spook gave his boss a little salute and, without a word, reached out to grab TC's cock. The grip alone sent another spasm through Top Cat's body and made him squeeze down on Brain more tightly again. It barely took a couple of strokes before the squeezing went made as TC's cum sprayed all over his underling's shirt. Brain followed him up by letting loose that big sneeze, blowing himself right onto his back with a loud "Achoo!" and taking TC to the ground with him. It took a moment later for TC to realize that he'd also cum right about then though, when he felt something wet slip past his burning and twitching hole. "Wow! You're a natural, TC." Top Cat's motor control was slowly returning, and he glanced back to see Fancy admiring the show. Choo Choo was lying on top of him, wide-eyed but otherwise exhausted. "Yeah, well, what else would you expect?" He smiled and turned back to Spook. "Say, uh, Spook, you got any more tricks like this up your sleeve?" "Oh, sure, pops, like, tons." "Of course, you do." Top Cat chuckled for a second and shook his head. The feeling still hadn't left him. Brain hadn't even started to soften yet, it felt like. But, even satisfied as he felt he was still definitely hungry. "Well, then, gang, get me off this thing. We've still got lots more practice to get ready for tomorrow." *** The men were gathered and ready to go in no time the following day at TC's call. The plan was simple, foolproof even as far as Top Cat could see it. It had taken a little late night street-walking, but he'd laid out every spot perfectly for each one. "Okay, Fancy-Fancy, you've got a client in the gated district; Chooch and Spook, you've got the docks; and Benny, I've got you set up with a mentor down in the China town. Let's go, men, blur blur blur, you know how impatient those Johns can be." At the order his men dashed off, leaving him alone in the alley and waiting eagerly for returns. Well, it was close enough to alone anyhow. "Uh, what about me, TC? You get me set up with anyone?" Brain raised his hand to get the boss's attention. Top Cat smiled gingerly down at the little guy and shook his head before responding. "You're staying with me, working boy. Can't risk you wandering off again and ruining Spook's beat. Don't worry, you can help me count all our earnings when they get back." He chuckled to himself and turned away too hide a bit of an involuntary blush as he thought of those earnings. Although, it brightened a bit more when he thought about the actual reason for keeping Brain back. The pitter patter of nearby size tens brought him out of his reverie though, and he had to look back to catch good old officer Dibble making his way into the alley, casually swinging his club like he owned the place, as usual. "Good morning, TC, Brain. Being law-abiding as usual, I see." "Of course, officer, wouldn't have it any other way." Top Cat casually waved for Brain to make himself scarce. He wouldn't need the lug for some time if her had to keep the cops occupied. "Right. And where's the rest of the gang then?" "Well, I'm sure I wouldn't know." A plainly suspicious smile crossed Top Cat's lips, and his eyes rolled as he thought about exactly what the rest of the gang was up to. Then, a rather intrusive thought supplanted those imaginary activities. The smile only grew more suspicious. Dibble leaned in closer, setting an arm on the trash can Top Cat was speaking from. Having him closer only made those intrusive thoughts more prominent. "Yeah, right? And I'm supposed to just believe that?" Top Cat just shrugged. Partly it was a half-hearted effort to throw Dibble off, but the other part was reflex. He decided to just give right on in. "You can believe whatever you like, Dribble. But tell ya' what." He shot the cop a wink. "Believe this one and I might just be able to swing you a two for one discount. What do you say?" "Heh. I'll bite. Just what are you up to now, TC?" "Brain, dear boy, come on back. We got a customer."