Tails’s Demise


Fiona grumbled as she walked to a nearby restaurant, she needed to drown her frustration in something to eat or else she felt like she was going to burst in anger. Not only did she lose a great catch just a few days before, that catch being none other than Shadow the Hedgehog himself, but her now former best friend left her tied up and completely at the mercy of a 50 horny dudes horde. She didn’t even think that her holes could fit so many dicks until now, nor had she experienced a level of pain that she wouldn’t find arousing, yet here she was. She sat down, grumbling as she looked through the menu in search of something good enough to drown her sorrow, when her eyes caught another customer, on the table right in front of her. It was a yellow male fox with two tails and kind of a good look. She studied him, then it hit her: that had to be the twin-tailed genius Rouge told her about, Miles Prower also known as Tails. Fiona looked at him up and down and grinned slightly: maybe things weren’t over yet. This guy could maybe be even better than Shadow after all. She got up from her chair and went towards Tails’s table, swaying her hips as she did. Tails noticed her through the corner of his eye and blushed as he saw the curved fox beauty going straight for him. He was a sucker for a good old pair of bouncy boobs and hoo boy, she had the bounciest pair in town for sure. She sat in front of him, placed her elbows on the table and laid her chin on her entwined hands, flapping her eyelids as she effortlessly charmed him.


“Uh… H-Hello…?” asked Tails, flustered and maybe a bit creeped out.
“Hello to you, cutie…” she said, giggling softly and still flapping her eyelids as she never lost eye contact with him, her light blue eyes fixated on his light blue eyes almost maniacally.
“C-Can I help you?” asked Tails, he had never been good around girls and surely this one wasn’t making things easier for him.
“Yes, you could, I guess… You could tell me what’s a fine looking cutie like you doing in this hole of a place… And your name…” she chuckled sensually, waving her furry tail ever so slightly.
“Oh. Uh, My-my name is Miles… B-but my friends call me Tails…” he stuttered, his blush growing in intensity as she kept staring at him. “A-and I’m here to… To see some of this place’s nice places…” he finished, rubbing the back of his nehad as his blush grew.
“Really now? And tell me, is one of those places the BDSM Club?” she asked, grinning and making him wince.
“H-HOW DO YOU… I-I mean, uh… no?” he asked, trying to lie.
“Pft… Please, I know there is nothing worth seeing here rather than my club… But let’s not talk about jobs here… You don’t happen to know Rouge the Bat, right?” she asked, changing the subject to ensure a false sense of security with him.
“Uh, yes. I work with her at G.U.N.” said Tails, indeed he found some calmness as the topic changed to something not sex related.
“Heh, really? You know, she is one of my closest friends. She did tell me a lot about you.” said Fiona, flirting with him a bit.
“Really? She did?” he asked, waving his tails a bit.
(More than you can think of, shorty...) she thought, snickering.
“Yes, she did. Only good things, mind you. She said you’re a real worker.” said Fiona, giggling a bit.


 Tails was very giddy hearing that, since he held a lot of respect for Rouge (and something else too…) and hearing that from what he thought was one of her best friends made him feel very important. The two’d chat a while and Tails offered her lunch, which she gladly accepted, until he had to go to the bathroom.
“I’ll be back!” he said, going inside.
“...Take your time, shorty…” she mumbled as he was gone and took a small bag out of her cleavage. She rustled in it and took out a small pill, dropping it in what remained of Tails’s food then she patiently waited for him to return, which he did after a few minutes. He sat down, finished eating and unknowingly swallowed the pill, then they resumed talking until Tails started to feel a bit woozy.
“Hm? What’s wrong, Tailsy? You look out of it…” said Fiona, acting innocently.
“Mngh… I feel… So tired… Yet I have slept… well and… I’ve taken a nap… On the bus…” he groaned, struggling to keep his eyes open and to stand straight but failing as he felt more and more sleepy until he straight out plopped his head on the plate, snoring lightly as the pill had done its job. Fiona chuckled, finished her meal, paid the restaurant then she lifted Tails on her shoulder and headed straight for her club, patting the back of her new catch with a satisfied grin.
(This was so easy I almost pity this poor fool… Almost...) she chuckled in her mind as she walked past the door and went into the fun room, getting everything ready for when he’d wake up. He woke up a few minutes later, groaning as his head spinned and he felt like his body was made of cement due to how hard it was for him to move. Tails groaned and tried to focus, only then realizing that he was now wearing latex gloves and socks, his arms have been tied behind his back and his legs have been also tied together along with his tails and he now had a collar on his back, ending on a six feet long leather leash. He gasped and tried to shake free but the ropes were tight and actually dug a bit in his skin and fur, making him whine as it hurted and making him even more confused as to where he was.


The door opened and Fiona came in, dressed in her dominatrix uniform completed with a whip at her side and followed by her male servants carrying a big carton board box with TOY BOX written on it.
“W-What the?” he asked before having the whip crack on his chest, making him cry out in pain.
“Silence, pipsqueak. You are only allowed to speak when I say so.” Fiona commanded and gave his body another crack of her whip, making him sob silently and fall on his chest as she walked in front of him.
“Let’s make this clear: I’m going to turn you into my personal sex slave, my personal pet. I was very close to having one but my so-called friend took that away from me. Now I’m taking you as his fill-in. You have great potential, sure, but you need the proper training. Which takes us to the here and now. I’m gonna fuck you up so badly that you won’t be able to tell what’s pelasure and what’s pain anymore…” she said, grinning and tugging her whip in her hands, making Tails gasp at the idea, though if it was a scared gasp or a kinda turned on gasp, she couldn’t tell. She rummaged through the box and took out a plastic ring, not wider than 7 inches, then she pushed Tails on his back and pinned him down.
“First, I’m gonna check your length… If you know what I mean…” she said winking and raising her plump butt, showing Tails her vagina and butthole. Just seeing that turned the twin-tailed fox on, but then she slammed them on his face, smothering him with her butt.
“Mmmmm, now that’s more like it…” she cooed, rubbing her ass on his face as she got comfy “You know, I’m so used to sitting on others’s faces that now I can’t never be comfy with a normal chair anymore…” she said, grinning at his muffled moans vibrating on her pussy “Hey, you better get used to the feeling and taste, pipsqueak. Because you’ll be doing this for a long time.” she advised him, chuckling as she rubbed more. Tails moaned as he felt her kinda heavy ass squishing his facial features and her pussy pressed against his muzzle, so he shyly started to lick it which made her apply more weight on him.
“What was that lame-ass lick? Do it better or I’ll squish you!” she grunted, which scared Tails and made him lick her pussy crack deeper, letting him feel her taste and warmth and being rewarded with a small coo from the fox.


“Hehehehe… Better. Keep it up until I tell you to go deeper, pipsqueak. Remember that I could crack your skull like a coconut with my ass any moment…” she said, grinning evilly as she rubbed his face with her ass more. Tailsdì groaned as all he could do was savour her pussy and sniff her butt so he did it, mainly because he didn’t want her to whip him or, worse, squash him. She purred and wagged her tail as Tails savoured her, rubbing her shapely butt on his face more and making him whimper in her pussy, the vibrations adding to how good it felt.
“Mmmm… Deeper, shorty…” she moaned, her pussy growing wetter the more Tails savoured her. He gulped and pushed his tongue inside her vagina, making her arch her back a bit and shudder, the wriggling muscle inside her turning her on as it wiggled and squirmed against her folds. Soon, Tails made a slightly louder whimper which made Fiona open her eyes and see that he had gotten hard, and hoo boy was that a juicy hard on he had! It was a whopping 8 inches long, with plump balls and a bit of a girth on it as well, all making it the best dick she would have wished for.
“Ho ho, jackpot for me…” she chuckled “Since you’re servicing my butt so nicely, I’ll give you something sweet in return: sweet release. But, if you cum before I order you to, you’ll face my wrath. Is that clear, shorty?” she asked, bumping her ass onto his face more to make him moan in response.
“Taking that as a yes…” she chuckled and wrapped her big wobbly breasts around his cock, starting to massage it and sucking the tip too, which was the only thing coming out of her tits. She smirked and slipped the cockring around his root, squeezing it and preventing him from cumming. Tails whimpered in discomfort as the ring squeezed his cock hard, so much that nothing would come out of it, and it kinda hurted him, despite the insane bliss coming from having his tip sucked and the rest of his dick rubbed by her perfect furry tits.
“Mmmppphhh… Mmmbbb… Just making sure… Ssslllppp… That you’ll not cum…” she said between suckings, loving how hot and salty his penis felt against her boobs and mouth as she teased it. Locked in a dirty 69, the two kept pleasing each other until Tails started to get sloppier, a clear sign that he couldn’t take it anymore: his balls had actually swollen a bit due to how much cum had gathered in them and his cock had grown more veins and turned redded with all the blood rushing towards it, the pressure inside it growing at such a constant speed that the twin-tailed genius was genuinely scared of it popping. Fiona too was at a breaking point: between sucking and rubbing that juicy cock while having her pussy and ass treated was making short work of her sexual stamina, but she would never cum first, so she secretly loosened the ring enough for Tails’s cum to literally erupt out of his urethra and into her mouth, making her gasp as she wasn’t expecting such a huge load from him but she still happily swallowed the cum, then she lifted her butt from Tails, making him gulp down fresh air as he panted.


“What. Did I. Tell you? Did you hear me saying that you could cum? No. Yet you came. A lot too. I think you need a bit more discipline, boy…” she glared at him, grinning evilly as she unraveled her whip and struck him down a few times, making him tear up, then she topped and smothered him again, this time with her boobs. Tails made a muffled moan as the furry boobs pressed on his face, her fur tickling his nose and her sweat tricking on his eyes. She massaged his head and face with her nice, big tits, giggling and wagging her tail as he squirmed under her, all he could see was boobs and fur and all he could breathe was her lust-infused smell and sweat. He writhed and struggled under her, unwillingly rubbing his cock between her asscheeks which made her chuckle and squish his face harder, earning herself a moan that sounded both pained and horny.
“Huhuhuhu… Someone likes it rough, huh? You’re so my type, foxy…” she said smirking evilly and pinning him harder continuing the hellish sexual abuse of Tails until she started to feel him growing number under her due to the lack of oxygen within her tits, so she moved away and let him catch his breath,k his chest rising and falling as he gulped down oxygen with his eyes closed and an expression between discomfort and bliss plastered on his face.
“You may speak, boy. I wanna know what you think of this so far.” she said, getting up and placing her hands on her hips while striking a suggestive pose.
“Hah… Hah… Cough, cough… Wh-Why…? Why are you… D-doing this? Wh-What did I do to you… T-to deserve this…?” he asked, starting to sob and tear up while he coughed lightly. She narrowed her eyes and planted a foot on his face, trampling him and making him whine and lower his ears.
“I guess you’re not as smart as my ‘friend’, Rougey, said you are… I’m not doing this because you did something to me, you little shit. Heck, I don’t even know you. But like I said, you seemed like the perfect sexual slave and, if I want something, I’m used to getting it, no matter what. But Rouge took away what was rightfully mine, so now I’ll have you take his place.” she grunted, applying more pressure on his face with her foot.
“You’ll never leave. You’ll kiss your sorry ass life goodbye and live to serve ME for the rest of your pitiful, perverted life. Is that clear? Because I hate repeating myself and I’d hate to break you before I got a chance to really play with you, pipsqueak.” she hissed, swaying her tail and moving her feet away, then she lowered herself on him, widening her legs and lining her pussy with his cock. Tails widened his eyes as he couldn’t take it anymore (or could he?) and struggled hard, even though the rope gave him friction burn, to try and impede it. Of course, that was pointless and Fiona smirked at his pathetic attempts to get free before her pussy swallowed his dick completely.


She hissed through her teeth as his dick filled her pussy completely, rubbing against her inner walls and sending pleasure up her spine, but she managed to not look as pleased in order to still show some dominance. Luckily, Tails was too lost in pleasure to notice: Fiona’s pussy was hot, slimy and squishy and it pulsed and rubbed around his cock and she wasn’t even moving. Then she started moving her hips up and down on his cock, making his dick move inside her, soon she was joined by him bucking his hips, thrusting his cock deep into her while moaning loudly. He couldn’t keep his tongue in his mouth, drooling on the floor, and tears of bliss escaped from his eyes along with sweat as he got worked up pretty quickly, due to the foreplay before.
“Mnf… Mnf… Throbbing already, huh? You’re such a disappointment…” she said, mocking him with a smirk as she kept moving on him, torturing his penis with her good-feeling pussy as she utterly dominated him. But then she suddenly stopped moving, keeping his penis inside her but not making him move by pressing down on his chest with her hands.
“H-Hn?” asked Tails, already looking lost.
“If you wish for this to go on, you must agree on becoming my slave, Tailsy… Do it, and I’ll let you cum inside me all the time you want… Or don’t, and be forever cursed to either cum outside or not cum at all…” she said, grinning. Tails groaned, he wanted this. He wanted to cum inside her, to feel good, but was it worth it tossing away his dignity? The answer came embarrassingly shortly after, and came out of his mouth so quickly that even he was surprised by it.
“I-I will. I will b-be your sex slave! J-just please, PLEASE, let me cum inside! Let me cum inside, I’m b-begging you… M-Mistress!” he shouted, trying to move under her but being stopped by her. She grinned and lifted him in a sitting position, burying his face in her cleavage and resuming her fucking motions.
“Good pet… Here, have you reward and then some…” she chuckled as she moved his face to her nipples, giggling as he wasted no time in taking them in his mouth and greedily sucking them while he let Fiona dominate him. Surprisingly, Tails showed how resistant he was, holding on to his orgasm and letting Fiona ride him in the cowgirl position for a few more minutes until he really couldn’t hold it anymore and, with a loud moan muffled by the nipples in his mouth, he came buckets inside her, making her moan loud as she felt the hot, slimy spunk fill up her womb and trickle down her pussy while she also lactated, having Tails drink up her warm, sweet milk as she coed and moaned, wagging her tail before wrapping it around both of them to keep Tails in place as his orgasm slowly died down. When Tails was done cumming, he laid his face between Fiona’s boobs as they both catched their breaths, their sweat and drool mixing with milk, pussy juices and cum in a puddle on the floor. Fiona opened an eye and smirked tiredly, petting his hair and making him look up at her.
“G-Good job, pet… Now… You are… MINE…” she whispered as she petted him. 
“...Y-Yes… M-Mistress…” he cooed, the horror of being owned by someone muddled with the excitement of the many years of bliss to come.


The End