Tails' New Horizons- Chapter 1
Commissioned By: PandoraYoshi
Written By: Mana Araxis
Classic Tails is the iteration used in this story


It was another uneventful day for Tails at his workshop. Sonic was going about some business, giving the young fox some time tom himself. He noticed a strange Warp Ring in the nearby woods a day ago and today he was going to investigate it further.

“Hmm, it should be here.” Tails thought to himself as he walked through the forested path eventually ending up in the clearing he spotted  the day before. The Warp Ring revealed itself before Tails and began to spin wildly.

“This...isn't right.” Tails said fearfully as the Ring seemed to generate a strong gravitational pull. The cub couldn't resist hard enough and was sucked into the anomaly, vanishing almost instantly.

**Some time later**

“Where am I?” Tails said to himself groggily. He noticed he was on a beach of what appeared to be a deserted island.

“You okay there little fox?” Tails sat up and looked in the direction of the voice. “My name is Tom Nook . What brought you here?”

“Umm...you see.” Tails replied and proceeded explaining his recent events.

“I see, I see.” Nook replied back. “Until you are able to find a way home, why don't you help me develop this island further? I could always use a hand or paw. Ha ha ha ha.”

“I suppose that sounds like a good idea.” Tails replied. And so Tails began his new job on the island keeping the landscape maintained, aiding the other villagers and using a spare house Nook had on hand as his new workshop.

**Few Days Later**

Tails woke up to do some daily crafting when he noticed a message alert on his Nook Phone from Tom Nook himself. Tails opened and began to read the message.

Thanks for all your help these past few days Tails. I think we forgot to discuss the debts related to the house I loaned you for your stay. It comes out to about 500,000 Bells. Of course there are alternative ways you can clear the debt. Come to my office after you get this message and I'll explain further.

“Oof...” Tails thought to himself. He thought it was given to him, but that would have been naive thinking. Nook IS running a business after all. The boy decided to follow Nook's instructions; there was no other way in hell he would be able to raise that amount of Bells in such a short time.
**Inside Nook's Office**

“Hi there, hi there.” Nook greeted as Tails arrived in his office. The office had a long reception desk and two work desks in the back.

“Hiya Tom.” Tails greeted back. “So what did you have in mind so I can clear my debt?” 

“Oh, it's pretty easy. That is, if your up for it.” Nook continued with a twinkle in his eye.

“I am. Please tell me. I'll do anything.” 

“Anything? Well we can start easy today, then go from there.” Nook replied as he rubbed his crotch seductively and slowly unzipped his grey dress pants. “Come Tails, follow me to the store room.”

Tails followed his boss to the storage room. It was dim lit, but it had enough space for the both of them. Nook undressed himself, slipping out of his pants and green diamond patterned sweater.

“Now then little fox, all you have to do is be my toy.” The raccoon dog turned around, sporting a girthy 12 inch member, with a large ball sac to match. Tails quickly blushed, gazing at Nook's naked body, let alone his well endowed equipment. “Think you can handle this up your bum? “Heh heh heh.”

“Oh..umm, I can try!” Tails stammered, rising to the challenge. The cub found a wall fixture he could brace and held onto it tightly and bent over for Nook. Raising his tails, he presented his pinkish tail hole as he spread his legs. The boy's small back sack hung below his taint, his boyhood becoming erect. Nook took notice of Tail's canine like cock. The deep red, tapered tip and small knot at  his shaft's base, it only made Nook fall deeper into a deeper lust. 

“Mmm..” Nook moaned as he approached Tails and began to rim his virgin hole. Saliva coated the boy's anus as he vigorously ate him out. Nook fondled Tail's white furred ball sack as he took in the fox's musk, burying his muzzle deep in him.

“Unghh...unghh.” Tails moaned. Of course this was just the preparation. Gripping each of Tails' wrists, Nook pinned the boy to the wall and slowly inserted his 12 inch member into Tail's tight tail hole. Tails yelped, his eyes widened and braced his teeth as the withstood the sharp sensation of his ass stretching to accommodate Nook.

“Hah..hah...hah.” Nook groaned as he pounded Tails. Pre cum and saliva coated Nook's member as he repeatedly penetrated his new toy. Tails' ass cheeks clenched with every thrust, his boyhood and balls flopping erratically. This went on for over five minutes before Nook was approaching his orgasm.

“Ungh...I think I'm...” Nook said as he slowed down and buried his shaft deep inside Tails.  The fox could feel the raccoon dog's warm seed fill his insides. It was an insane amount to boot. Nook withdrew his cock which was now semi flaccid. Tail's gaping hole dripped of excess cum from Tom Nook. The workout tuckered Tails out to the point of collapsing on  the storage room floor.

“Nice job there kid. Meet me tomorrow same time and we can do more advanced techniques.”
“Ohhh...okay.” Tails replied dazedly. After Tails came back to he headed to the ocean to clean himself up and rested for the day, giving his sore tail hole some rest. He just hoped no one noticed too easily of his gaping anus.