Tails - Coming Out on Top
Story 1 - Caught by the Covenant


Tails had been captured by the Covenant of Despair, a terrorist organization made up of Mobians hateful towards humans. The fox had been careless while scouting one of their hideouts. Fortunately for Tails, Despair only held a grudge against humans. Doubly fortunate for him...his captors were all female. Not that the organization didn't include males, it just so happened that several of their top agents were femme fatales. So, his captors were giving him a bit of a warm welcome... rather than punishing Tails for spying, the ladies were intent on using their charms to win him to their side. Of course, the foxy hero was doing his best to resist, even as they tied his arms to a soft, warm bed. "Wh-what are you doing? Whatever you try, I won't talk!" Tails insisted. Three ladies stood around him. A pink skunk and a purple echidna were tying him to the bed while a dark grey wolf smirked at him. The wolf had one eye covered by her hair, and all three were wearing the tight, black leather uniforms of Despair, which perfectly accented their curvy figures. The wolf stroked her fingers around Tails' muzzle, chuckling softly. "There's no need for you to talk... We'll just get you to moan..." she said, "My name is Fera, and you will be my newest ally. Daisy and Violet here will help you realize that." the wolf told him. Tails looked from Fera to the others. Violet was the echidna, clearly, which made Daisy the skunk. Tails struggled against his bonds a little. "Y-you'll torture me?" he asked nervously. Daisy stepped back, and grinned as she started to unzip her tight uniform. "Quite the opposite..." she winked. Violet was starting to unzip as well, a bit more slowly. "You're so cute... I can't wait to let you take me..." she whispered seductively. Tails blushed, his eyes widening as he saw Daisy's suit slip free first, her nice, juicy melons held by a bright green bra. Tails couldn't believe what was happening. He could feel his loins stirring as he watched the girls strip for him. They wanted to fuck him!

Tails' eyes darted back and forth, looking for any escape, before he gave up and settled his gaze on Daisy. She was unstrapping her bra, letting it slowly fall to the floor. Tails blushed deeply, feeling his member rise to life quickly as he got an eyeful of her luscious breasts, covered in soft white fur like her belly. Daisy smirked at his reaction, playfully lifting his boobs in her hands for him to see. "Yeah, I think you know a good thing when you see it..." she purred, approaching him slowly, her own eyes drifting down to look at his hardon. Tails gulped. "I-I won't be b-brainwashed by you..." he said nervously. Daisy licked her lips, leaning closer to his dick. "You're so big... so beautiful... I need to feel that fox meat..." she cooed, her breasts wrapping around his shaft in the next moment, the skunk holding her tits around his length! Tails gasped, blushing deeply. Her breasts felt so soft, so warm. He wanted them...and he was getting them. Yet somehow he had to keep his mind under control. He struggled lightly, letting out cute gasps as Daisy began to move her breasts up and down his length. She let out a lustful purr. "Your dick feels nice on my tits... Mmm, don't you feel it?" she whispered, bending her head down to kiss his throbbing head. Tails squirmed, gasping as he tried to free himself. He was only succeeding in helping his cock move between those lovely breasts. "Ahhh… N-nghh… I-I can't..." Tails huffed, desperate to get away, and also desperate to fuck her. He looked away, only to see Violet watching him with a smirk, wearing nothing but her underwear. He lost some of his inhibitions in the moment, thrusting his cock into Daisy's tits and smacking her chin with his tip! She panted excitedly, grabbing his head with her lips and sucking it with a lewd moan while her hands grabbed her bust and squeezed it over his cock. Tails rolled up his eyes and moaned. "P-please...ahh...m-more!" he huffed. Daisy released his tip from her mouth and licked her lips. "I thought you'd never ask..." she cooed.

The lovely pink skunk climbed atop the fox, slowly lowering her pussy onto his length. Fera and Violet were watching with smirks, confident that they would break their new pet in the end. Indeed, Tails seemed well on his way to breaking, already looking at his captor with lust, blushing and moaning softly as her wet pussy lips accepted his cock. "Mmm... Such a big boy..." Daisy cooed, lowering herself down until she'd taken most of his dick inside her. She bent down over him, rubbing his fluffy chest and giving him quick kisses to his muzzle. "Once you're ours, we can play like this all the time..." she teased, rising up and starting to ride him, moving up and down along his foxy pole slowly and sensually. Tails gasped and softly moaned, grasping at his bonds not to struggle anymore, but just to grip something while jolts of incredible pleasure shot through him. "Ahh... Ohh… F-feels so good..." he huffed, his ears folding submissively as the lovely skunk rode his cock. He watched her breasts jiggle as she sped up, eagerly hopping up and down, panting blissfully as she felt his cock piston deep into her walls! "Ohh! F-fuck! H-he's so good... C'mon and fuck me, little man!" she panted, her eyes looking at Tails pleadingly, begging for his cum. He couldn't hold himself back anymore. Tails began to thrust up his hips, willingly pumping his dick into Daisy's warm, wet passage. She let out a gasp, letting Tails take control as she rode his pounding cock, lustful cries escaping her as he kept going. "Yes... ahh, yes! J-join us! Ahh, we need your cock! F-fuck!" Daisy moaned, getting wetter and wetter by the moment. They wouldn't be able to contain themselves much longer. Tails thrusted again and again, pushing himself to the edge. Soon, he and Daisy moaned together, both of them cumming hard! His seed shot deep into her, leaking out and down his shaft, and Daisy fell over him, kissing him deeply. "Mmmm… You're ours..." she purred.

Tails was hardly given time to rest between Daisy getting off him and Violet approaching. The purple echidna had gotten undressed while Daisy was playing with the fox. Tails glanced at her, breathing hard while he tried to rest, and his eyes widened at the sight of her breasts. They were actually smaller than Daisy's, but they looked quite lovely anyway. She was smirking as she knelt down, taking hold of his cock. "Mm, covered in your cum... Looks tasty..." she whispered, her other hand cupping his balls, "And you still feel so full down here... I like a virile boy like you." she purred in a sultry tone. Her flirty voice was getting him hard again, and he whined softly. He wanted her. Violet grinned, knowing it. She slowly slid her tongue along Tails' shaft, cleaning the cum off it and moaning softly. "You're so big... Mmm, so tasty... You have to join us..." she cooed, lowering down to kiss his balls before lapping her tongue back up his length. She was worshipping his cock, kissing and nuzzling it between licks. The fox whimpered, his hands still bound. He pulled on his bonds a bit, his thoughts filling with the desire to pin the girl down and plunge his dick into her. But for now, Violet was teasing him, driving him wild. She slipped her lips around his tip, sucking him a bit while her hands fondled his balls and butt. "Yeah... You want to fuck me, don't you? I can tell, you're so hard..." she cooed, kissing his tip and then licking his length nice and slow. Tails groaned softly as he squirmed. "I... I want to... Y-yes... Please, I need to m-mate..." he huffed. Smirking, Violet started to stand up. "Alright...I'm going to set you free..." she whispered.

True to her word, Violet untied Tails' arms, allowing him to freely sit up. He blushed, looking around. Daisy was resting, Fera was slowly unzipping her uniform and Violet was on the bed, legs open for him. Tails couldn't believe that instead of torture, these Agents of Despair were lusting over him. He couldn't take it. He suddenly grabbed Violet's wrists, his hard shaft rubbing her slit as he pinned her down on the bed! Violet gasped softly, lightly struggling against him for just a moment until she felt his tip poke her entrance and begin to push inside! "I-I'm sorry... I n-need this!" Tails gasped, pushing his cock into her deeply, looking down into her eyes before leaning forward to kiss her! Violet moaned into the kiss, her tongue meeting the fox's eagerly as she laid back and let him take control. Tails slid his hands slowly up her arms, his hips thrusting into her quickly, his cock sinking deep inside her again and again. As the kiss broke and they gasped for air, Tails took Violet's lovely breasts into his hands. "Y-you feel so good..." he huffed, licking at her nipples gently while he cupped and rubbed her boobs. Violet gasped and squealed in delight, grabbing his head in her hand, encouraging him to keep lavishing her tits with affection. "Y-yeah, keep going you adorable ball of fluff! Ahh, f-fuck me! I-I'm yours!" she panted, eyes rolling back into her head as she took his thrusts, feeling his cock massage her walls furiously. He was ramming so close to her weak spot, teasing her body. His two tails twirled behind him as he nipped at her nipple, keeping up his pace. "Sh-she's mine...ahhh…" he parroted her sentiment, blushing as he felt himself getting close. His cum would mark her as his! He released her breasts, his hands grabbing her own as he thrusted harder. Violet's body arched and her eyes widened as she felt him strike her weak spot, making her moan out as her pussy clenched over his shaft! Tails couldn't hold on, he started to pump his cum deep into the echidna, gasping lustfully as he filled her! He blushed, ears drooping as he looked a bit embarrassed. "O-oh, my... I-I'm sorry..." he huffed. Violet moaned softly, cumming over his cock as it was stuck inside her. "Don't leave us... Mmm..." she cooed, laying under him with a tired expression.

Fera was next, and she approached the bed wearing a black bra and panties, holding a leash and collar. "Now... It's time for me to break you, so that you'll happily serve us from now on..." she said with a smirk. She was moving closer to him, clearly planning to slip on the collar and have her way with him, when the fox hopped off the bed and closed the distance to her himself. Fera was surprised when he cuddled up to her, one hand lowering her arm that was holding the leash while the other wrapped around her curvaceous frame. "You don't need that leash... Shh, it's okay..." he cooed, nuzzling into the surprised wolf's neck! Fera lifted the leash briefly, but lowered it again with a gasp as she felt Tails' hands grab at her covered breasts, tugging at her bra! "N-naughty fox! What do you think you're doing?" she huffed, her red eye looking into his baby blues as he stepped back, slipping her bra from her chest. "I'm coming willingly... I need you, Fera!" Tails cooed, blushing deeply as he got an eyeful of her lovely breasts, bigger than Violet's but not excessively huge. He had to touch them! As he grabbed them into his hands, cupping them softly, he pressed his lips to Fera's and kissed her, making the wolf gasp and moan from his lustful actions! Tails reached down during this, and casually took the leash from Fera. Then, once the kiss broke, he lifted it up for her to see. "Maybe we could still use this... If you trust me..." the fox cooed, his hard cock poking Fera's belly as he stood close to her! The wolf felt a blush come to her cheeks, quite unusual for her. She placed her hands on his shoulders and smirked. "This isn't how it's supposed to go..." she sighed. Tails reached around her neck, slipping the collar on her without resistance. "I'm not hearing you try to stop me..." he whispered, his length starting to rub against her black, wet panties. Fera inhaled slowly, looking at him defiantly for a brief moment. However, as he teased her through her panties, she gasped and grabbed on to him. "Give it to me... F-fuck me, fox boy!" she begged!

Fera was lowered down onto her hands and knees, Tails sliding down her panties from behind as he gripped her leash. He briefly sniffed at her arousal and wagged his twin tails. "Ah, man... I can't control myself anymore..." he huffed, rising over her and gently slapping her naked butt with his hard cock. She gasped softly. "Damn, h-he's still hard as a rock..." she whispered. Tails leaned over her, feeling her big fluffy tail rub up against his chest as he lined himself up. "So...instead of my joining you...think you'll join me?" he cooed, nuzzling into her neck. Fera felt his tip push into her wet pussy, and she gasped softly, trying to lower her face to hide her shamed blush only for Tails to lightly yank her leash, keeping her up! She was supposed to make him fall for her, but instead she was falling for him. Tails pushed his cock in further, and the wolf let out a needy moan. "D-damn you...!" she panted, trying to act defiant. Tails reached around her, giving her soft breasts a nice grope to make her gasp loudly. "So, you don't want me to keep going?" he asked, taunting her. The wolf let out a lustful sigh as he gave her ripe melons a squeeze. "Ahhnn… F-fuck me...!" she gasped, blushing deeply. The fox's twin tails wagged back and forth behind him, and he pulled his dick back before roughly thrusting it back into the wolf, nice and deep! She let out a loud moan, and Tails smirked, thrusting again. Violet and Daisy were watching, sitting nearby, rubbing their own clits as they watched Tails take their commander. The horny fox had one hand fondling her breast and the other groping her ass while he pounded deeper and deeper into her pussy, panting lustfully as he went. Fera rolled up her eye, moaning as she accepted his every touch, completely seduced by him! "F-fuck, ahh! F-fox boy, h-how?? How are you so g-good??" she panted, feeling his cock throb within her, readying his third creamy load! Tails lightly nipped at her neck, licking at the spot after. "Fox instincts..." he whispered with a sexy growl, giving her a few more deep thrusts, gasping as he felt himself ready to blow! Fera moaned along with him as she felt his seed pumped inside her, filling her pussy and marking her his!

Tails rested on the bed for a moment, and noticed the three girls gathered around him and blushing heavily. "Wh-what?" he murmured, blushing back. "You're really cute sitting like that, master..." Violet cooed, sidling up next to him. "M-master?" Tails asked, blushing deeper. He was just reacting to the situation, he had no interest in becoming their master... Not that he was complaining. Fera sat at his other side, purring softly. "We understand if you're tired... But a foxy stud like you, mmm, I so want to have your baby..." she whispered, petting his head gently. Daisy knelt down between his legs, nuzzling his cock. "Oh, yes... Get us all pregnant, master..." she purred. Tails' jaw hung open. This was beyond anything he'd imagined. He pinched himself... Yup, it was really happening. These girls had accepted him as their mate. Perhaps it was their mating season? He decided not to question it too much. Chances like this don't come along every day! "Alright... Let Master take care of you, girls..." he said softly.

Staying seated on the edge of the bed, Tails grabbed Fera's crotch, rubbing his fingers against her wet pussy lips. Violet was laid behind him, tangled in his tails, gasping softly as she felt the skilled appendages rub her pussy and tease her breasts. Meanwhile, Daisy climbed into his lap, his free hand holding her atop him as her flower accepted his cock once again. He smirked and kissed the pink skunk as his shaft pumped up into her passage, drilling deep into her, seeking her womb! The three girls all gasped and purred in lust, loving his touch. "Ohh, yeah... Such energy! D-don't stop, master!" Daisy moaned, riding in his lap!

Soon enough, Tails was on his back, and it was Violet's turn to ride his cock! The fox's eyes were fixed on her bouncing purple breasts as the echidna moved up and down eagerly, moaning each time his dick plunged deep inside her! Daisy and Fera saw how he was staring, so they leaned over the bed and put their own boobs in their master's reach. "Here, master, would you like a taste?" Fera purred, stroking Tails' yellowy bangs. He blushed and reached his hands to cup and jiggle those pretty tiddies, leaning up a little so that he could give Fera's nipple a lick, followed by Daisy's. Violet huffed softly, speeding up her motions to make sure she wasn't forgotten. "Ohh, ahh! T-tailsy, c-cum for me!" she panted.

Once finished with Violet, Tails was back on top, pinning Fera to the bed and holding her legs spread as his cock plunged back inside her! Behind him, each of his two tails took one of the other girls, rubbing Daisy's pussy and giving Violet a soft titfuck! But his focus was on their leader, Fera, who had wanted to make him theirs, and who was now all his. He looked at the lustful gaze in her crimson eye as he pounded into her passage, his balls smacking her with each thrust, still full of seed to pump her full! The wolf rolled up that eye and let out a short howl, grasping the bed sheets under her as she took the fox's powerful thrusts! "Aaaahhh! T-tails... B-breed me, ahh, and I w-will... make our Covenant yours... m-my king..." she huffed, blushing hard. Tails blushed back, hiding it by leaning down and kissing her deeply. He moaned into the kiss, his thoughts swirling with ideas of breeding any girl he desired. His cock pulsed. He couldn't contain himself. Breaking the kiss, he moaned out, shooting his load deep inside the lustful wolf...

...Months later...

Tails was resting on a throne within the former headquarters of the Covenant of Despair. With Fera and her allies out of the equation, Despair had been easily defeated. Now, the fox calmly looked around this throne room, admiring the followers of his own sort of covenant...one dedicated to pleasure. Fera, Violet and Daisy all stood around him, sporting plump baby bellies and wearing loose-fitting clothes to accommodate that fact. "Master, we have an offering for you..." Fera said, bowing slightly for him. Tails climbed to his feet. "Oh, my, so unnecessary. You three should be looking after yourselves, you have our pups to consider." he said, hugging the wolf and giving the others a warm smile. "Oh, I think you'll like this, master." Daisy winked. "Come with us, and then we'll take a little break..." Violet smirked. Wanting them to look after themselves, Tails agreed to follow them. Together, they wandered to the master bedroom, and opening the door, Tails was greeted with the sight of a light blue fennec girl sitting on the bed, naked and blushing, while a white fennec who appeared to be her twin sister was tied up by her wrists and ankles on a chair in the room. Wait, Tails recognized her. "Gemini!" She'd helped his friends in some previous adventures. Admittedly, Tails found her quite attractive, being a fox like himself. Fera rubbed his shoulders and smirked. "She was hiding a runaway agent of Despair, Libra..." she said, turning Tails' head to the freed fennec. "H-hey there..." Tails waved. Libra grinned and waved back. "They told me how cute you were...and how virile. I thought... I might want to join your new coven..." she blushed, "My sis, Gemini, needs more convincing." she added. Gemini's ears folded. "I was kidnapped..." she said. Tails glanced at the others, but Fera, Violet and Daisy were already leaving. He let out a sigh. "Still gotta work on training them..." he murmured. He then felt Libra's arms around him, her finger landing on his lips. "Let's give Gem a show, and you can decide what to do with her after..." she cooed.