--Disclaimer---
This story is entirely fictional and doesn't/shouldn't represent any real life situations. It is strictly for entertainment purposes.

The music pulsed echoing through the club. The DJs beats pulsed happy vibes as Amy's Birthday party became an even greater celebration. After last year's debacle of a murder mystery train party, Sonic and Amy seemed closer than ever. However no one had expected Sonic to finally propose to Amy. It shocked everyone and kicked the normal vibes into high gear. That is all except for two of them. Tails always liked Sonic as more than a friend, but he never told him the truth. Now he was heartbroken to discover he and Amy were going to settle down. Similarly Shadow secretly had a thing for Amy, but his constant rivalry with Sonic kept his true feelings at bay. He thought the concert tickets he got her last year would be perfect to squeeze his way in, but she just went with Sonic anyway. Sitting at the bar as everyone danced, Tails bitterly sipped on his virgin cocktail watching his crush dance into Amy's arms. 

“A beer and a shot,” Tails heard from his left side. Shadow turned, scoffing at the newly engaged couple before sitting down next to Tails. 

“Some party, huh Shadow,” Tails mumbled, staring into his glass. 

“Damn faker,” Shadow grumbled, throwing back his shot of whiskey and leaning back on the bar. “Never thought he'd actually do that.” 

“Yeah me neither,” Tails said, not to cry.

Shadow, ever observant, couldn't help but see how upset Tails was. It was only then that the young fox's actions over the years clicked together in his mind. He certainly always suspected it, but it seems he was right all along. It was still early in the night, but Shadow wanted to confirm what he was sure of now.
“Wishing he'd have asked you instead?”

“Yeah,” Tails sniffled, then jumped and back peddling waved his hands. “I mean, NO! What? Of course not! That would be weird! It's not like that!” 

“Pffft, Ahahaha!” Shadow laughed, “caught ya! I fucking knew you had a thing for him!” 

Tails sighed, “Oh whatever. Not like it matters now. Might as well just tell everyone I'm gay tonight too.” 

“Hey don't be so hard on yourself kid,” Shadow replied, punching his arm. “That faker is just too oblivious to have appreciated you anyway.” 

“Hehe, thanks.”

As the night marched on, Shadow and Tails remained at the bar just talking. The music shifted from club jams, to pop, and eventually into slow dancing. By that time though Shadow and Tails weren't facing the dance floor anyway. While Tails had to stick to non-alcoholic drinks, Shadow managed to sneak him a few sips while the bartender wasn't looking. By the time the party was wrapping up, Shadow was rather tipsy, and Tails had a mild buzz.”

“You know Shadow, you're easier to talk to than you look.” Tails said, blushing. “Wish I'd have opened up to you sooner.” 

“Hey. Hey youuuuuu’re, a cute kid. No plablphlem.” 

“Are you gonna be ok to head home?” 

“Oh, don't yooooou worry about me, I'm…” THUD. Trying to stand up. Shadow immediately fell face first into the floor. 

“Shadow!” Tails shouted, rushing to his aid. “Are you ok!?”

As he rolled his drunken friend to the side, the bartender came over and crouched down beside Tails. 
“Hey I went ahead and called you two a cab 15 minutes ago. They're waiting out front for you.” 

“Oh my gosh, thank you so much.” 

“No problem, make sure he sleeps that off. You two had a rough night.” 

Thanking the bartender profusely, Tails pulled Shadow to his feet and the two stumbled out the door into a taxi. Giving the driver Shadow's address, the car sped off away from the club. 

… …

Helping a still tipsy Shadow inside, Tails thanked the driver and waved as he drove off. A bit of fumbling and another faceplate later and Tails was sitting with Shadow on a couch. Getting comfortable in his seat, Shadow's head started to clear enough to speak again more readily. 
“S…sorry about all this.” 

“Don't worry about it.” Tails shook his head in reply. “I won't leave you alone tonight.” 

“You…really are a great kid.” Shadow looked up at him, then casually gave the young fox's body an up and down glance. His body was nice, slender, and petite. Not that dissimilar from Amy. His tender touch was perfect against Shadow's fur. Perhaps, he thought, Tails was just what he needed. 
“That faker is an idiot for not choosing you. Any guy would be lucky to have you.”

“Hehe, thanks,” Tails rubbed the back of his head and blushed. He wasn’t used to hearing such things from the dark hedgehog. 

“I bet you're great in bed too! Like damn, with that figure you'd drive ‘em wild,” Shadow said, getting more bold. His inhibitions still very low from the alcohol, he was ready to make a move.

“Wait, what?” Tails stopped rubbing his head and looked at Shadow. Was…was he seriously giving him that kind of compliment. 
“I mean thanks, but I've never actually…Shadow?” As Tails tried to rationalize Shadow's behavior the dark hedgehog tilted his head and leaned toward him. 

“I guess we'll have to get you initiated then.” 

“Initiated into wha…MRPHHH!” Tails eyes shot open as Shadow pressed their lips together. Hands up in surprise he wasn't sure what to do as the dark hedgehog gave him his first real kiss. 

Puckering off of him, Shadow's eyelids lowered as he looked at the young fox with drunken lust. 
“How was that, little man?”

Tails was stunned. The stoical rival of his best friend just kissed him. He knew it was likely just the booze in his system talking, but there was an exciting flutter that rushed through his chest. Oh how he longed for years to be noticed by another boy, but he never expected it to be Shadow. 
“Shadow…” Tails mumbled, trying to come up with a response. “...Why?”

“Heh,” Shadow smiled, figuring it wasn’t the worst response. “Cuz you're pretty damn sexy for a kid I guess. What do you say, little man. Wanna lose your virginity with me?” 

Oh WOW!, Tails thought…was this really happening? Sure Shadow wasn't Sonic, but here was another mobian hedgehog offering to take his innocence. Just like that. No strings attached. 
“Shadow I,” finally moving himself out of his shocked state, he placed both hands on Shadow's chest. Feeling his warmth, Tails closed his eyes and thought things over. 
“I…I think I'd like that.” He finally said timidly, opening his eyes, and looking at Shadow. 

Shadow smiled, knowing his night was about to finally turn around. Shifting to the side, he slipped out of his shoes and pulled off his gloves. Tails in turn did the same matching him. The young fox then returned his hands to Shadow's chest, running his bare fingers through the tuft of thick white fur. Meanwhile, Shadow held Tails’ forearms as he leaned forward kissing him gently again. 
Muwah.
Tails giggled, as the butterflies in his stomach tingled more and more. His heart was racing as he felt another boy's touch. It was everything he imagined it to be and more. Shadow was surprisingly gentle, allowing him to get more comfortable at his own pace. 

“You're really soft, Shadow. I’m…not really sure what to do though.” 

“Just relax little man. You're the first boy I've done this with anyway,” Shadow sheepishly admitted. 

“Hehe, ok.” Tails giggled. 

“Ok, so I'm gonna kiss you again but this time open your lips more so I can put my tongue inside. Then you kinda push yours against mine.” Tails nodded and parted his lips. Shadow pressed against him, and as he said slipped his tongue past the fox's lips. 
“Mmmmmph,” both boys mumbled as their tongues danced together for a few moments. 
“Mwah!” A trail of saliva dripping between them as they both breathed more heavily. 

“Whoa,” Tails gasped. “That was crazy!” 

“That's a real kiss, little man. Now why don't you lay back, and I'll get you started.” Tails looked at him confused but did as he was told. Falling back on the couch cushion, he propped up his head on the arm rest and watched as Shadow knelt between his legs. Reaching down to the young fox's thighs, Shadow pushed his legs apart revealing Tails’ bulge. It was still small considering how young he was, but not bad for an 11 year old. With a clear view of Shadow's as well, Tails noticed how much larger the 18 year old hedgehog was. Tails gulped, as he never really thought about Shadow's size until now. 
“Let's see now,” Shadow said, raising his right hand above Tails’ package. Placing his palm on the little fuzzy lump, he rubbed up and down, coaxing out the fox's boyhood. 

“Ah!” Tails yipped in surprise. Having never had anyone touch his privates before, it was a sudden but pleasant sensation. “O…oh wow!” 

“Hehe, feel good?”

“Ah, y…yeah.” 

“That's good. Now show me what you're hiding in here,” Shadow chuckled slyly. Sliding one finger around the bulge, he found the folded flap of skin and tugged. In an instant Tails’ cock sprung loose into the open air. The young fox covered his eyes in embarrassment as he was now fully exposed for Shadow to see. 
“Damn little man! You're pretty big for your age!” Shadow was surprised to see that Tails already had a 5 inch erection. The red rocket was impressive to see jutting up from the boy's body. Though he'd never really thought of another boy's dick as sexy, Shadow found himself licking his lips regardless. Reaching out with his left, he tugged further exposing the young fox's balls. Unlike his shaft, Tails’ balls were more akin to his age. Hugging tightly against his lower knot, it seemed they  just recently had descended. Shadow smiled once again and returned his right hand to the task. Grasping the fox’s twitching boyhood, he gently began rubbing up and down. 

“Ah, ah, ah,” Tails began moaning in his high pitched innocent voice. He never would have guessed he'd be getting touched like this by Shadow. While he knew it felt good to rub himself, it certainly didn't feel this good doing it by himself. 
Shadow was surprised at just how much Tails’ boyish moans were turning him on. He could feel his bulge tightening as his cock desperately needed to be released from its fleshy prison. Letting go of Tails. Shadow sat back on the couch and scooted himself forward so his bulge was pressed against Tails’ balls. Looking up to see why Shadow had stopped touching him, Tails gasped as Shadow's cock flopped out against his own.
“Whoa!” Tails gasped, as Shadow smirked.

Shadow's cock was a monstrous 9 inches, and had barbs on one upper side from base to tip. It pulsed, leaking precum down onto Tails. 
“Sorry little man, I couldn't hold back any longer. How do you like it?” 

Tails reached down with both hands and wrapped them around Shadow's length. His jaw hung wide as he got a feel of the ultimate lifeform's thickness. Instinctively Tails began rubbing it just like Shadow did to him. 

“Oh yeah, that's it. Rub it together with yours too,” Shadow's lower lip quivered. Tails’ young hands felt incredible on his cock. His fur gently tickled his sensitive member. With his instruction, Tails pushed his boyhood up and then rubbed it against Shadow's. Immediately both boys let out a long moan, letting their lustful desires fuel their actions. 

“Ah, Sh…Shadow,” Tails moaned. “This feels…so…good!” 

“Fuaaa! Yeah, keep going!” Shadow replied, breathing heavily. Falling forward, Shadow propped himself on his palms, which rested on the couch. As Tails rubbed them together, Shadow began bucking his hips adding to the friction. 

“Ah Shadow. I’m…ANGH!” The pleasure seemed to be overwhelming for Tails and without warning he was forced into an orgasm. His legs shot up in the air and wrapped around Shadow's back. Shadow immediately reached underneath him, and scooped the young fox up hugging him close. Both boys moaned as Tails’ boyhood throbbed, spraying a short blast of thin and clear liquid onto Shadow's chest. Shadow ground his teeth as he rubbed Tails’ back, soothing the fox as he came. Shadow felt so proud that he brought the inexperienced boy to climax so quickly. For some reason having Tails’ thin boy-cum soaking into his fur just felt right. 

Knowing he was far from finishing, Shadow eased his hips, and just held onto Tails for now. Letting the young fox ride the waves of please back to reality, he eased the boy back down and watched him close. As soon as he was sure Tails had caught his breath, he kissed him. Shadow was sure to let the last of his youthful moans disappear between their lips. “Mmmmmmh, hmmmmm. Mmmmmmh. Mwah!” The boys stared deep into each other’s eyes, smiling. 

“Oh, Shadow. That was…wonderful. I didn't think sex would be so much fun.” 

“Pfft, that wasn't exactly sex, Tails” Shadow chuckled, “But it was a great start.” 

“Huh?” Tails was confused. “That wasn't sex?”

Shadow stared at him momentarily, deciding on how blunt he wanted to be with the boy. Both of them were still rock hard, so he decided it wasn't worth waiting too long. Lowering his head down beside Tails’ left ear, Shadow whispered softly. “I'm going to put my cock in your tailhole, little man.” 

“Tails’ eyes went wide. That was the last thing he ever expected to hear. Jaw dropped, he stuttered as Shadow pulled his head back and smiled, staring at him. 
“My, t…t…t…t…t…t…”

“That's how boys have sex,” Shadow said. Reassuring him it wasn’t some weird joke. “Do you still wanna do it?” 

Tails felt his knot swell just at Shadow's words. He never imagined that's what sex really was, but despite the shock he couldn't help but be intrigued. Just having Shadow's cock rub against his own already felt amazing. He began wondering just how good it would feel from the inside. Closing his mouth and gulping, Tails nodded hesitantly. 
“Y…yeah. I…I wanna have sex with you, Shadow.”

Shadow nearly came just from hearing that. The young fox's timid voice asked for it…it was the most perfect thing to ever grace his ears. 
“Ok little man, wait here a minute.” Shadow said, pushing up off of the couch. “I gotta go grab something, first.” 
Shadow might have been leaking precum like a fountain, but he wasn't dense. This was Tails’ first time, and lube would be a MUST. Luckily Shadow always kept a tube in his bedside table. A quick run there and back, and they were ready. Shadow knelt back on the couch as he was before, admiring Tails’ continued enthusiasm. 
“I'm gonna get you started with my fingers first, ok?” Shadow squirted a little of the lube onto his right hand and rubbed his fingers together. Tails nodded nervously, as his left leg was lifted up over Shadow's shoulder. With one finger the dark hedgehog traced around the edges of the fox's tailhole, coating it with the slippery liquid. Once he was satisfied with how much was applied, he gently pressed the tip of one finger into Tails. 

“Ack!” Tails yipped. He wasn’t quite sure how it was going to feel, but the sensation was unlike anything he could have expected.

“You ok?” 

“Y..yeah. Sorry. Go ahead.” 

Shadow smiled and pushed the rest of his finger in. Tails let out a soft and involuntary whimper as his tailhole was penetrated for the first time. Shadow could immediately feel how tight the boy was. Even after loosening him up, he knew it was going to feel amazing inside him. Slowly the dark hedgehog worked his finger in, out, and in small circles. Making sure to add extra lube as he worked in the starting portion, eventually Tails seemed to get used to the feeling. 
“Ok little man I'm gonna add another digit.” 

“Mmmhmm,” Tails hummed in compliance.

Starting with just the tip as before, Shadow slowly pushed a second finger inside. Tails gasped feeling his tailhole stretch wider, which to his surprise sent a spike of electrifying pleasure through him. Seeing Tails’ cock throb, Shadow knew he was starting to enjoy the sensation. Speeding up a little, Shadow spent an extra minute pumping both fingers in and out.

SHLUCK SHLUCK SHLUCK SHLUCK 

Tails bit his lower lip and moaned. It wasn’t even another boy's dick yet, and he was already in love with the feeling. He couldn't wait to feel what the older teen had for him next. 
“O…oh, Shadow!” Tails gasped, feeling another well lubricated finger probing at his entrance.

“Still doing ok?” Shadow asked, already knowing the answer. His own dick twitched leaking precum onto the couch. The tightness around his digits kept him aroused as he fingered the young fox. 

“Y…yeah. Put the next one in.”

“Hehe, you got it little man.” 

SHLUCK!

“Ah, yes!” Tails shouted, now completely intoxicated by Shadow's touch. It was one of the best sensations he'd ever experienced. He couldn't believe he waited so long to open up about his feelings. Shadow was perfectly guiding him through his blooming sexuality. 
“That feels so gooood!” Tails moaned. “I…I need more.”

Shadow was a little surprised how quickly Tails had turned slutty in front of him. The 11 year old was practically begging to have his innocence taken. By this point most of the buzz Shadow had from earlier in the night was gone, and he was about to fuck the boy's brains out. Everything felt perfect. Neither cared about Sonic or Amy anymore. It was just them. 
“Get ready, little man. Here comes the real deal!” Shadow said, quickly pulling out his fingers and pressing his dripping member against Tails. 

“Do it Shadow!” 

“Ungh!” Shadow grunted, pushing the first half of his 9 inches deep into Tails’ body. 

“Oh hell yeah!” Tails screamed, his tailhole stretching wide. His legs shivered and he gripped the couch cushion tight as his virginity melted away. Immediately as Shadow pushed inside, the young fox could feel his boyhood seemingly being touched from the back. He couldn't have known, but this was his still underdeveloped prostate getting its first jolt of pleasure from another boy. 

Shadow was only halfway inside, but was already in love with how warm and tight Tails was. It was better than any girl he'd ever been with. The fox's tiny body squeezed him tight, causing a long stream of precum to splash inside. Not giving his little lover much time, the dark hedgehog gave him the first hump forcing his cock in even further. Tails gasped followed by a satisfied moan as with just a few more humps and Shadow was completely inside. 
“Oh fuck!” Shadow groaned, “Your tailhole is the best!” 

“Ah, Shadow…l…look!” Tails gasped looking at his stomach, seeing a lump where Shadow's massive cock was pressing up.” 

“Oh damn, are you ok?” 

“Y…yeah. I …It feels so goooooood!” Eyes rolling back slightly, Tails let his head fall back and he wrapped his legs up around Shadow's back once again. “S…sex is awesome!” 

“O…ok. Now h…hold on tight.” Shadow stuttered. Getting well balanced Shadow took a deep breath and then began thrusting in and out. 

PLAP PLAP PLAP PLAP PLAP PLAP PLAP PLAP 

Both boys breathed heavily. Their moans all but synchronized as Shadow pounded Tails. The young fox's cock slapped back and forth between his and Shadow's groin. Hands gripping the couch he closed his eyes letting the pleasure of having his tailhole destroyed by Shadow guide his thoughts. Every thrust sent electric sensations through his whole body. It was like he was made for taking cock. His twin tails wrapped around his lover's back, as he could feel every inch of Shadow inside him.

Shadow couldn't help but enjoy just how quickly Tails became accustomed to him. Holding the fox's legs for support, the black hedgehog smiled as he watched the range of emotions on Tails face. He looked so cute as he panted and moaned, completely surrendered to the pleasure of his first time. The boy was taking all 9 inches of him like a champ, too! No girl he'd ever been with had been able to take the whole thing, and here was this 11 year old, virgin, fox, squeezing him tight and begging for more. Tails was the most perfect lover he's ever had. With so much awesome pleasure Shadow was nearly at his peak. He could feel his balls swell as the familiar sensation began to build. Reaching further with his hands, he pulled Tails up to his chest just as he b began to cum. 
“Argh, Tails!” 

Tails gasped as he was lifted up. The change in position caused a loosening of his tailhole,  letting Shadow's full length to easily slip completely inside as the first blast erupted from him. The young fox let out a high pitched yelp as Shadow's hot seed painted his insides. His eyes shot open as he felt every rope of the hedgehog's thick love juices. His own cock throbbed wildly giving him an additional minor orgasm from the feeling of getting filled. His body shivered as Shadow held him tight, gritting his teeth, and groaning as he claimed Tails for himself. 
Having let go of the couch, Tails now had his arms wrapped around Shadow's neck, letting his lover ease down from his climax. The two boys holding each other in such an intimate way, felt wonderful. 

Finally catching his breath, Shadow looked up at Tails who was smiling at him. Without the need for a single word, both boys pressed their muzzles together sharing a long, passionate kiss.
“Mmmm. Mmmmm. Hmmmm. Mwah!”

“So, how was that little man?” Shadow chuckled, still balls deep inside Tails.

“Reeeeeally good,” Tails moaned. “Thanks, Shadow.”

“Glad to hear it. Oh, I should probably pull out now.”

“No way!” Tails protested, latching his legs around Shadow's hips. “I wanna stay like this! Your thing feels so good, so just leave it in.” 

“Haha, ok then.” Shadow replied. Easing them both down, the two laid together the rest of the night. As the two boys eventually became flaccid, Shadow's dick slipped out of Tails letting his cum dribble from the young fox's tailhole. Neither seemed to care, as they stayed close in each other's warmth. After a few minutes in silence Tails finally spoke up.

“So…what do we do about Sonic?”

“Hrmph,” Shadow grumbled, nuzzling his head on Tails’ shoulder. “That faker can do whatever he wants, but there's no way he can have you now.”

Tails giggled and snuggled closer to Shadow. 
“Yeah,” Tails sighed in relief. “Hey, Shadow? C…can we have sex again tomorrow?”

Shadow hummed, rubbing Tails’ back. 
“Of course, little man. We can do it any time you want from now on.”

“Hehe, thanks Shadow.” Tails replied, closing his eyes. 

Neither of them would have guessed at the beginning of the night they'd end up in each other's arms. No one would have expected Sonic to propose to Amy, but that was now history. Despite once being enemies, the young fox and the brooding dark hedgehog were now lovers. Held in their warm embrace, the two boys would one day share their love with their friends, but for this first night the secret would remain in the shadows.