Hello everyone, welcome to the new version of DWC, now under a new title. I've kept a lot the same but I chose to add in a little more and try to make this into a halfway decent story. I originally planned this to be a smut fic. But its grown into something more. Anyways I hope you enjoy and I'll see ya at the bottom.

Chapter 1.1

Tails had always been a hard-working, young fox for as long as everyone knew him. He was also very bright for his age, at the age of 16 he'd already completed high school and lived at home working on his projects. Hence, why he was now currently walking up to one of his neighbor's homes. Upon arriving at the place, he took a look around and frowned. He saw a red brick home, the paint had faded and chipped away and was obviously in need of some work. But that wasn't all, his sky blue eyes took a look around the yard, seeing the grass had grown too high and wild. Trash, namely broken beer bottles and other things littered the whole yard. This greatly upset Tails cause he had a high respect of nature and didn't like when people abused it. With a sigh and a shake of his head, he walked up to the old, brown, wooden door, knocking a few times he waited for the owner to answer. Hoping it was the female in the house and not the male. As he waited, Tails found himself thinking back on how he got into this situation.

Flashback

Awakening to the smell of fresh waffles filling his nose coming from downstairs, Tails sat up in his bed yawning as his blankets fell down around him. Stretching his spine with a loud pop, he jumped out of bed and made his way out of his room and down into the kitchen. Finding his mother; Rosemary, standing at the stove, cooking, she was clad in just a lacy baby blue gown which left her back exposed along with a decent amount of cleavage.

"Good morning hun," she said, setting down a plate of waffles, covered with thick syrup, along with melted butter, in front of him as he sat at the table. Tails blushed upon seeing his mother's chest being exposed as the gown hung down while she bent over.

"Aw, mom, I told you to call me Tails, like all my friends, do," he said, pouting slightly, picking up his utensil's and digging into his food.

"Now Miles, you know you're my son. I'll call you whatever I want to," she said with a stern tone.

Tails, of course, knew better than to argue with his mother. Many on the council had learned that the hard way. Rosemary was kind and sweet, but piss her off and well... yeah. "Yes mother," he replied calmly as she ruffled his hair.

"Good boy," she said, walking over and sitting down across from him as she started eating her own plate of food. "Oh, by the way. I got you another small job. I know you've been looking for some extra money."

Looking up from his food while chewing on some, the young fox blinked curiously. "Job? What job?" he asked, now curious, like his mother said he had been looking for some extra work but figured he could find his own.

"Oh, one of our neighbors; Mrs. Fox, needed some help around her house. Since I know you've spent all your money on your projects, I offered your services to help her out."

Tails frowned a bit, "Mrs. Fox? Do you mean that female red fox who married that green hedgehog who's always fighting with people? I thought they hated and didn't want anything to do with us?" Tails asked, having finished his plate, he looked over at his mother.

"No dear, she's actually very nice. When I offered your help, she just jumped at the offer and said to send you right over. Now put your plate in the sink, then wash up and head over. She's expecting you any time now."

Tails nodded, going and placing his dirty dish in the sink, then he went upstairs to clean up and head off for the day.

End Flashback

Still waiting outside the door, Tails knocked again a bit harder. He began to wonder if anyone was even home. 'Maybe I should just go back home, I still wonder though why she jumped at the idea of having me help her? Seems a little odd...' Tails thought to himself.

Tails were so deep in his thoughts he didn't hear the door open, or the sexy female voice say "hello?" After a few seconds, he blinked and looked at the open door with his eyes open wide. A red furred vixen with short chestnut brown hair and deep ocean blue eyes. She currently wore nothing but a soft, fluffy black towel around her figure, which didn't leave much to the imagination. She looked down at Tails, who still had his own eyes locked on her and suddenly found his mouth to be dryer then the hottest desert.

A sly smirk forming across her smooth lips she spoke in her sweet voice, "you must be Tails?" she said.

Blushing a lot, the male fox quickly averted his eyes away from the female in front of him. "Ah yes I um am, and you're Mrs. Fox?" he said, trying not to stutter.

"Call me Fiona," she said, teasing the younger fox by just slightly letting the top of her towel slide down, just enough so that he could see the slightest hint of her areola before she pointed at a nearby shed. "All of the tools are in there, just use what you need to get the job done. I'm sure a cute stud like you can make it happen. I'll come to check on you later." she said, closing the door, giving him a sexy wink, swaying her tail in front of him before she closed the door.

Tails stood there, completely dumbfounded for several moments. Being 16 he was going through typical hormone changes, and that female fox was one hell of a beauty. 'Did she just hit on me?' he thought. 'You know she did! You almost saw her tits!" his mind told him with pure excitement. "Wait what?! AH! Forget it!" Tails said, shaking his head as he went off to the shed to find the tools she said were there for him to use.

Meanwhile, inside the home, now currently in the bathroom, stood Fiona. "Mmm he's even cuter than his mother told me," she mumbled to herself.

Grabbing the black towel, she tossed it off, revealing her full sexy figure in the mirror. Sexy B-Cup sized breasts, with perky pink nipples, a killer hourglass shaped figure, well-toned legs and an ass any man would die just to touch. She knew she was sexy as fuck, even now at the ripe age of 27, she'd managed to keep her amazing figure. Hence, why she was married to her current husband, everyone knew he'd married her for her figure of course. But as of late, he'd basically been ignoring her. She knew he was fucking around behind her back, all the late night's and the phone calls he'd been getting, it was obvious. Fiona may have made some mistakes in her life, but she wasn't stupid as Scrouge seemed to think she was.

"Hm... Maybe I can use that young stud out there," she mumbled to herself, walking over to the window, she looked outside, seeing Tails currently pulling some of the overgrown weeds in the yard. "Mmm, oh yes, I think I can," Fiona said, watching Tails as she slid a hand down between her legs to brush her now wet slit. Smirking, she started up the shower as she began to think up her newest plan and how to pull it off.

"Ah! Come on, almost... Got it!" Tails said, falling back onto his rear and laughing softly holding up said weed in his hands. "Tough little bugger weren't ya?" he said with a smile then looked around. "Phew, I think that's the last one, now onto the grass," he mumbled, looking around the yard and seeing the bushy grass stare back at him like saying come try to take me on. So far, he'd been at this for a few hours now and was quite pleased with the work he'd accomplished. The yard definitely looked a lot better than it had been before. "Let's see.." he mumbled, checking off the list in his brain to make sure he missed nothing else. Standing up and dusting himself off, he walked over to the nearby lawnmower and went to start it up, only to hear Fiona's sweet voice calling his name.

"Oh, Tails!" Fiona called, watching as he ran over and almost fell dead in his tracks at the sight before him. The sexy fox was standing there now all finished from her shower, but that wasn't what stunned him. It was her outfit, she wore a skin-tight black crop top that left her whole stomach exposed. Her breasts bounced with each movement she made and her cream furred stomach were in full view to him, he saw it was still slightly damp from her shower. She also wore black pants, which were just as tight as the top and they fit so perfectly onto her figure Tails could make out the outline of the panties she had. 'She's wearing a thong!' he thought only to blink when she waved her hand in front of him. "Tails? Mobius to Tails, you alive there?" she asked.

"Huh? Oh! Yes? What's up?" he asked, blushing and looking away so Fiona couldn't see he'd been staring yet she knew he was.

Letting a slow smirk cross her lips, Fiona chuckled softly. "Well, I figured since it's so hot outside and you've been working pretty hard. That maybe you'd like to come in and have some nice cold lemonade?" she asked, placing one of her hands on her hip while she looked down at him.

"Ah, um, sure, sounds good," the young male said, now following Fiona back inside her home. Naturally, his blue eyes were glued to her rear, which swayed side to side with every step she took. He swore she was doing this on purpose.

Once inside the home, she led him into the nearby kitchen "have a seat on one of the stools." she said, heading over to the fridge. Tails plopped himself onto the nearest stool, sitting at the counter. Watching as Fiona opened the fridge door to get them the drinks. 'Time to put operation fox into motion' she thought, with a sly smile. Fiona knew Tails had been staring at her rear as she walked inside, just like she knew he was staring at her right now. Slowly and intentionally she bent over into said fridge, making sure she leaned over enough for Tails eye's to land right on her plump, but well-shaped butt. Her tail swished around her behind, almost like it was enticing the male fox to come get a taste as she proceeded to tease him.

When she began to stand back up, an idea crossed Fiona's mind, "mm I know it's in here somewhere" she said, now bending down even lower which caused her pants to slide down just enough so Tails could barely make out the lining of her black thong. Chuckling she waited a few minutes, then stood up as Tails quickly looked away, a slight redness staining his cheeks, Fiona, of course, knew he'd been looking. Naturally, he hadn't been the only one, while he worked outside, she'd, watched him from the windows. Under his fur, was a body that was building muscle and still growing. Fiona knew Tails would grow up to be quite a young stud and she was gonna make sure she had herself a taste. And keep him all for herself if he performed properly, what Tails didn't know was while he worked outside, she'd gotten off in the shower watching him. Grabbing a couple of glasses, she set em down and poured some of the drink for them. Fiona handed the glass to him and began to make some light conversation. "So Tails, what do you do in your spare time?" she asked curiously.

"Oh well not much, besides helping my best friend Sonic defeat that crazy Dr. Eggman. I'm usually just working on my own personal projects or keeping busy since I've already finished high school. My mom says I'm a real prodigy." he said, blushing embarrassed while taking a sip of his drink, finding it tasted amazingly delicious. "What about you? I'm sure married life must be interesting in its own way?" Tails asked.

Fiona scoffed and waved his question off with her hand. "Tch, not really. Unless you count your" making quotations with her hands as she spoke. "Husband being gone all day and night, out chasing any tail, he can get his grubby paws on." Fiona shrugged, obviously, this wasn't a topic she cared to discuss.

"Oh, I'm sorry to hear that. Must get kinda lonely no?" he said, finishing his glass. He felt he was in an awkward situation. He wanted to get back outside, quickly and away from this. Fiona shrugged again, "don't be, I'm not. Besides he's pretty much a loser anyway. Sometimes, I think I was stupid for letting myself marry him in my younger days." she said.

Frowning, Tails spoke without thinking "what? You're still young and well um.. beautiful." As soon as the words left his mouth, Tails felt like he'd planted his foot within his mouth.

Fiona smirked, knowing she had him now as she placed a hand across her chest, a slight blush forming across her cheeks. "Oh really? You find little ole me beautiful?" she asked.

Tails knew he'd put himself into a mess now. "Well um... I mean, um..." He tried to speak.

Fiona chuckled, slowly standing up. "Well..." She walked over and climbed into the chair where Tails was sitting and planted herself on his lap. He could smell the scent of her perfume, it was like an intoxicating drug he found that he couldn't get enough of. "Mmm, well Tails?" she whispered into his ear, letting her fangs graze the tip of his twitching ear.

The way she spoke, using that sexy yet sweet tone, sent shivers down, Tails spine, making his whole body shudder due to her actions. "I um, ah, um, well yes you're very beautiful," he said, feeling his hormones begin to take effect on his young virgin mind. Tails slowly began to pant as Fiona smirked and leaned closer, pressing her body against his own.

"Mm, how about you come get your payment then?" she whispered, only to pull away and walk towards the nearby stairs.

"But, but I haven't finished the work yet?" Tails said, now confused as Fiona just smiled sweetly.

"Oh, don't worry about that. You've done more than enough. Now come on follow me." Before the young fox could anything more, Fiona walked upstairs, the tip of her tail the last thing Tails saw before she disappeared.

Licking his lips, the fox downed Fiona's glass of lemonaid, then made his way up the stairs, seeing her tail pass into a nearby room. He followed, opening the door, only to stop dead in his tracks. Laying there on a bed with white lacy sheets and matching pillows was Fiona. But now she was clad in only a skimpy black lace strapless bra, it was obviously a size too small for her along with a sexy transparent black lacy thong, and matching long black stockings. Smirking at Tails, she slowly crawled on all fours to Tails, slowly licking her lips. "Mmm, ready for your payment?" she said seductively.

Tails was one hundred speechless, currently, his virgin mind was locked in a duel with itself. The more logical side was saying "run, run home now!" The other more lustful side was saying. "take that girl! She wants you bad!" While Tails was dueling with his own mind Fiona had climbed off the bed and made her way over to him. The next thing he knew a pair of soft, sweet lips were pressing against his own. "Oh my gosh! She's kissing me!" he thought, now surprised when her tongue slid out, licking his lips as he gasped allowing her tongue to side into his mouth.

Her tongue finding his own, they began to duel while her arms slipped around his neck, pulling him closer. Purring low, she broke the kiss slowly and smirked down at him. "Looks like someones excited," she said with a giggle.

Tails looked down, then gasped in shock. "AHH!" he said, quickly covering himself with his hands. His fox hood had poked out of his sheath. All eight inches, which were now covered by his hands and twin tails.

'Mm, damn! He's younger and bigger then Scrouge!' Fiona thought, licking her lips while smirking. "Don't hide it," she whispered. slowly moving down onto her knees in front of Tails. Grabbing his hands and tails she pulled them away, revealing the aching shaft. The tip was swollen with pre and throbbing. Reaching up with her left hand, she slowly gripped the thick shaft, earning a soft moan of pleasure from the young fox. "Hehe, mm, like that? I'd bet you're a virgin who doesn't even masturbate, aren't you?" as she said this, her hand was now stroking his meat, feeling it throb and ache under her soft touch.

Watching as he nodded, clearly embarrassed yet turned on by what was happening, Fiona went down and gave the tip of his pecker a soft kiss. Her eyes went wide at the sweet taste, making her want more, even Scrouge didn't taste this good. He was bitter whereas Tails was like the sweetest fruit she'd ever eaten. Opening her smooth lips, she began to take his shaft into her mouth, inch by painfully slow inch. Tails who was now moaning loudly, couldn't even believe this was happening. Here he was getting a blow job from the hottest fox he'd ever met in his life. Another loud moan came out from between his lips, feeling Fiona's wet tongue running down the underside of his baby maker, he could only describe these feelings as mind-numbingly good. Her tongue was clearly well skilled, running up and down the whole shaft, lapping at the twitching tip to get all of his sweet pre as it oozed into her mouth. Reaching up with one of her hands, she began to fondle and massage his swollen twitching balls.

Soon, Tails felt himself thrusting forward, trying to get more of his dick into the vixens mouth and to feel that amazing feeling that was now filling his whole body. "Ah, ah Fiona. I'm... something's coming!" he screamed.

Quickly, Fiona took his shaft from inside her mouth. Slowly licking her lips, she grinned up at him. "Mm, yep you are a virgin, but I won't let you finish... yet." Standing up, she sat on the bed again and motioned with her finger for Tails to come over to her. He did so, slowly and once he was standing in front of her, she grabbed his hands and placed them on her bra right over her breasts. "I'll bet you've never felt a nice pair of tits before, have you?" she asked, teasing him. Tails who was now unable to speak could only nod. His hands feeling the soft mounds through the lacy material of her bra. Fiona reached up behind her and Tails could hear the sound of a snap which caused said bra to fall right into the foxes hands as the vixen just grinned.

"Mmm, suck my tits, baby," she whispered, reaching up and pulling him by the back of his head down to her breasts. Knowing he couldn't do much else, he leaned forward, taking the erect left nipple into his mouth. Giving it a soft yet slow lick with his tongue, Fiona moaned softly and leaned closer to him. "Good boy." she cooed in pleasure. Tails liking the compliment licked it again. This time, a little harder than before. Using the roof of his tongue, he ground it against the hardened bud. But not to leave the other one undone, he began to work the right one with his fingers. Taking it in his grip, he slowly pinched and tugged it forward. Fiona threw her head back, letting out a loud moan of pure bliss. Obviously, she was enjoying this very much. "Mmmm, you're such a good boy. My so-called husband never pleases me like this," she said, pulling harder on his head as he switched nipples, sucking on the right one now while his fingers worked the left one.

Tails continued switching between both before he finally pushed them together and began to suck on both nipples at the same time. Earning more and sweeter moans from Fiona as she enjoyed every bit of this. Eventually, she pulled him off, then stood up in front of him. "Do you want to see more? How about this?" she asked teasingly, shaking her hips in front of him as she pulled his hand down between her legs to let him feel the crotch of her thong. It was soaked and very warm to the touch. Feeling that, along with the musky scent of her arousal coming off her panties was driving Tails crazy with lust. He nodded eagerly, wanting those panties off more than the air, he needed to breathe, he watched as her fingers hooked the waistband of said thong and slowly slid them down over her hips and all the way off. Smirking, she then placed it on his head, making sure the crotch was right over his nose, allowing him to get a full-on whiff of her wild scent. When he reached up to pull em off, Fiona slapped his hands away, "ah, no, no, they stay on cutie."

Laying down onto the bed, she pulled Tails down with him now between her legs. Being unsure what to do he was nervous, so she guided him. "Lick here," she commanded, guiding his hands onto her wet slit. Slowly Tails used his fingers to run up and over the smooth lips a few times before he leaned forward. Taking a deep breath to inhale more of that musky scent she had, slowly he slid his tongue out and gave her slit a slow but steady lick. Finding the taste a bit bitter, but also tangy. Tails licked it again, this time a bit more. Using his tongue, he probed around. Dipping it inside her seemed to affect her more as she gasped and arched her hips forward. Her hands pulling Tails closer as she dug her nails into the back of his head. "Mmm, yes right there, don't stop," she said feeling, his tongue sliding from the upper half of her slit down to the bottom then back up to where her clit was. Finding the small hard nub, Tails licked it slowly at first. Earning louder moans from the vixen as she cried out, her hips wrapping his around his head trapping him. Tails figuring she liked that, licked it again and again, harder this time as he wrapped his lips around it, sucking it gingerly at first then harder. As he pleasured her, Tails used different motions with his tongue, from zigzags to stroking up and down motions.

Tails noticed Fiona's pussy was getting more and wetter, so he slipped his tongue as deep into her baby hole as he could reach. Feeling the slick, wet inner muscles squeezing his tongue trying to pull him further inside her, while he twirled it around within her working to pleasure her. Fiona had to admit; for a virgin, this kid was fucking amazing. As Tails continued to pleasure her, she then caused him to stop when she pulled him up, planting a hard deep kiss on his lips, tasing her own juices upon them. Grabbing the thong she'd place on his head, throwing them aside, while pushing him down as she climbed over him. "Mmmmm, how about we do the best part and make you a real man now?" she asked seductively.

Tails instantly knew what that question meant. "Ah, ah but ah, we can't, your marri-" he tried to say before he was silenced by her soft lips capturing his own in another sweet kiss.

Breaking the hot kiss after a few moments, Fiona gave the young fox a sly smirk. "So? You want this as badly as I do." Fiona said, looking down at Tails twitching rock hard cock.

Reaching with one of her hands, she grabbed his hard fox hood in her soft grip, causing another sharp gasp from Tails lips. "Ah, but, but I don't have any protection!" He said nervously, hoping that maybe this would convince the female fox not to go through with this.

Fiona just smirked slyly as she chuckled. "Oh, don't worry, I'm on the pill. So we can go all we want," she said, lying of course. Fiona wasn't actually on any pills, but it wasn't like she was gonna tell Tails that. Grabbing his hard 'baby maker' with both her hands, she pressed the swollen tip against her wet slick pussy lips. "Mmm, now watch my hot pussy devours your virgin cock," she said smirking.

Pressing herself down slowly, Tails was forced to watch as his hard throbbing cock, slid into Fiona's tight folds. Feeling the slick muscles quickly envelop his entire shaft, he moaned out loudly, unable to believe what he was feeling. His cock felt like it was in pure paradise, a blissful pleasure so good it was mind-numbing. Her pussy was so tight and so wet, squeezing his cock tightly. Fiona was moaning loudly herself, Tails shaft stretched her almost to the limit, it'd clearly been a while for her, so now she was much, much tighter than usual. It blew her away that Tails was so huge and thick. 'Fuck! He's big!' she thought, pushing her hips down till he was fully sheathed inside her. Both of them moaning out.

"Mm, like that, baby? Feels so fucking good don't it?" she cooed, looking down at his face, which was completely contorted into a look of pure pleasure. Smirking, Fiona slowly brought her hips up, till just his tip was inside her, then slammed them back down hard, creating a steady and hot rhythm with the fox. Tails still couldn't believe this was happening, but now he was so horny he couldn't take it. Bringing his hands up, placing them on Fiona's bouncing rear, he gave it a hard slap, The sound of his hands slapping her flesh filled the room as Fiona screamed out. "Oh! Yes! I'm such a bad girl! Spank me, baby!" Fiona called out so Tails did it again, slapping her rear even harder this time. Each slap the male fox gave her, only turned Fiona on even more.

Her thrusts became harder, pressing herself more against Tails. But, he then surprised her by flipped them over, so now he was on top of her. Fiona was quite turned on by the fact that the young stud was taking full control of the situation. Now laying under him, her breasts swaying up and down with each hard and deep thrust the fox made into her. Moaning out, feeling the head of his shaft hitting the entrance to her womb over and over again. Enjoying every bit of this, she could feel the pressure building down between her legs. Knowing she was getting close, she could tell that Tails was too. His shaft had swollen to almost double it's size, while he rammed faster in and out of her. "AH! Ah!, Fiona, I can feel it coming!" Tails moaned out.

Grabbing the fox by his face, she hissed. "No! Not yet! Just a bit longer! I'm soo close!" she shouted. Tails tried his hardest to hold back the rushing orgasm that had been building in his aching balls. The feeling of Fiona's wet, inner walls, and the way her pussy squeezed and stroked his cock. Soon became just too much for the young virgin fox to bear.

A few deep thrusts later, along with a loud cry, Tails rammed his cock balls deep into her open womb, shooting his hot and fertile fox seed deep into her. Nine fertile strands filled her womb as the feeling of that warmth inside her, sent Fiona over the edge. Throwing her head back, she screamed louder than she ever had and came hard. Her tight pussy spraying her hot juices all over his orgasming cock. As they rode out the numbing pleasure Tails fell down on top of her, breathing hard and trying to catch his breath. Both of them were clearly worn out from this, panting hard, he looked up at her as she gave him a soft kiss on the lips. "Mm, fuck! You're quite a stud babe." Giving his ass a slap she smirked. "I think I'll defiantly keep you. Mmm, want to be my secret lover baby boy?" she asked him while placing feather kisses along his neck and collarbone.

Looking down at her as he still tried to catch his breath, Tails gave her a slow nod, laying his head back on her B-Cup sized breasts. Fiona watched as he rested with a smile on her face, this had worked out perfectly in her eyes. Several hours later, Tails woke up in her bed, finding that Fiona was gone, sitting up slowly he listened for anyone in the house but only heard silence. Looking around, he saw a note on the nearby nightstand that was addressed to him. Picking it up he saw it read

'Hey, lover boy had to go with the douche bag to a party for one of his friends. Thanks for all the work. Here's a special surprise you can enjoy later tonight when you think of me. You're baby Fi'

Under the note was the same black thong Fiona had worn earlier in the day, it had a stain of red lipstick on the front. Tails blushed a deep red, quickly stuffing the thong into his glove he left the house before anyone would know he was there.

Seeing it was now almost dark out, Tails quickly ran home as fast as he could. Upon arriving home, he found his mother, Rosemary sitting on the couch reading a book. She was clad in her usual purple dress and set the book down upon seeing Tails. "Hello hun, you've been gone all day? Did you have fun doing all that work?" his mother asked.

Tails briefly recalled his encounter with Fiona and blushed, but quickly got rid of it. "Oh, yes, I got all of that work done. She sure had a lot for me to do. But I made some decent money." he said, smiling at his mother. "I'm a go shower, then settle in for the night," he said, headed up the stairs before his mother could say anything more.

Rosemary smiled, but raised an eye at the way Tails acted, it seemed like maybe he was hiding something, but she chose to leave it be. "Okay, goodnight Miles," she said as he went upstairs.

Upon entering the shower, Tails let out a soft breath, 'that was close, I can't let mother find out what happened.' he thought, turning on the shower as he removed his shoes, socks, and gloves. Finding the thong he stuffed inside them, thinking back on the day he'd had, it still felt like just a dream. Climbing into the shower he didn't know that this was only the beginning of the newest adventure of his young life.

(End Of Chapter 1.1)

Well I hope ya enjoyed this updated version of chapter one. I'll post the other two chapters when I get the chance. Till next time.