Work Text
It was a day.Tails was at his house sitting on his couch and staring at his wooden floor into space, he was lost in his thoughts super nervous on what was to unfold later that day. today was his first date with his girlfriend zooey and how he feared this day, sure he's been to dinner with the girl at meh burger or invited her to his house to watch tv, but those were not really dates those were just a hanging out thing. this was a real deal they were going to go see a movie, then go eat at some restaurant, after that they're were going to her house to do who knows what. she said they were going to watch tv and "have some fun" what in the name of furry did that mean? the orange fox wasnt sure but it was making him nervous.Talis was too lost in his thoughts to even notice his blue hedgehog friend enter his home like as if it was his own."hows my ladies man doing?!" Sonic said as he walked in and shut the door behind him. Tails snapped out of thoughts as soon as he heard his friend's voice "oh i guess everything's fine" tails said not trying to hide the fact of how nervous he was and Sonic obviously noticed this.the blue hedgehog sat himself next to his orange friend."are you sure about that? you don't sound too good.""e-everythings fine Sonic," tails reassured "I'm just a little nervous that's all." Sonic was confused for 3 seconds but then he remembered about Tails and Zooey's date. he put a hand on tails's shoulder to comfort him. "you shouldn't be nervous buddy, you've went out with Zooey plenty of times!" Tails sighed "i know but those wern't really dates they were just..." Tails was having a hard time trying to explain this to the infamous hedgehog "i dunno but this date is different"Sonic took his hand off tails's shoulder put it on his chin then he said "okay, explain." "well... Zooey and i are gonna go see a movie, then we're gonna go eat at a place that isn't meh burger, then we're going to her house to have "fun" and i have no idea what that means and for some reason its making me feel weird."Sonic laughed after Tails' little rant just for the fact of how the implication went over Tails' head.Tails was confused "whats so funny?" he saidSonic rolled his eyes at his ignorant friend "isn't obvious tails! she wants to have sex with you!" Tails gasped and Sonic patted him on the back "don't worry buddy you'll be okay just wear protection ok"Tails blushed he felt a little weird for talking about this with his friend. "But I've never even kissed a girl before..." Tails said in a quiet voice very ashamed with his ears down and his cheeks red."oh you'll be fine," Sonic assured "first kisses can be great and im pretty sure theres tutorials online somewhere.""yeah but i don't want Zooey thinking im a vigin loser! im like an adult already and I've never kissed anyone." Tails sighed, it was stupid that Tails was upset about this maybe if he wasn't such a nerd he could of gotten some fresh pussy. Sonic was a little confused by this he never expected Tails to be so upset about his sex life it was totally not part of his personality."hey man its okay Zooey doesn't have to know that.""i could do that but Zooey's gonna find out sooner or later and It makes me go crazy!"Sonic went silent and so did Tails. awkward silence was in the air the only noise being heard was the chatter of towns people coming from outside, Tails was looking at Sonic and Sonic was looking at him, a little bit uncomfortable and confused, when suddenly Tails's smart brain got an idea!Tails got up and grabbed his friend by the arm leading him to his room "woah Tails where are we going?'' Sonic asked as his friend practically dragged him upstairs"to my room, duh"when they got there 12 seconds later tails shoved the hedgehog into his room, locked the door and closed the window blinds.Tails looked over at a very confused hedgehog who was next to the door rubbing his arm , he knew where this was going but he didn't want to assume anything."Sonic, don't think this is weird or anything," Tails said nervously walking up to his friend "you've had plenty of experiences with girls right," "uh... yeah." "well i was thinking..." Tails was starting to regret this but he didnt want to seize an opportunity like this "maybe you could teach me the basics of kissing."Sonic almost laughed, he wasn't bothered by this one bit "and you want me to do this... how exactly?""i dunno maybe you could--" before Finishing his sentence sonic cut him off with his talking"i could write it down for you, or look up a video for you, or maybe i could--" "just kiss me goddamit!" Tails yelled, although he wasn't trying he sounded a little desperate but oh well at least he got to the point. "well of its what you want," Sonic said smugly "consider this one of the most useful tutorials ever.""okay but don't think this makes us anything special," Tails said "i just want to know how to kiss a girl" "yeah yeah." sonic said rolling his eyes"im serious! we're just friends! so uh no homo?" xxxxxxThanks to Tails the homo was out of the way and the tutorial could officially begin."so what you wanna do first is grab her by the waist and bring her close.'' Sonic grabbed at Tails by the sides and brought him close to him both their chests toughing and both of them blushing."then you look her in the eyes to really show how much you love her," Green eyes looked into blue showing nothing but lust for a moment Tails felt pretty gay, but he said no homo "then you kiss her." That was the end of Sonic's sentance before attacking tail's lips with a full blown kiss, this was it, this was Tail's first kiss and he would never forget it because he did it with his best friend. Tails felt Sonic bring his arms to his back pulling him closer into a hug. after 10 seconds that felt like forever Sonic pulled away to take a breath, his arms still around his friend. "this is the part where you have to take notes because im done with explaining." Sonic said before pinning tails to a wall and bringing him closer into another kiss. this kiss was a lot rougher though with sonic grabbing all over him this time rubbing at his furry chest at shoulders. Tails melted into then kiss Sonic tasted like mint and all the rubbing felt relaxing he let sonic explore his body, trailing his arms from his chest down to his tails, he pulled at one causing the fox to gasp Sonic took this as a chance to slide in his tongue exploring his mouth and rubbing up against the other's tongue. Tails found his arms going from his sides up to Sonic's shoulders and to his back bringing him closer in a tight imbrace as he explored Sonic's mouth. after a good while Sonic pulled away, a string of saliva connecting to their mouths. They were both out of breath and blushing madly, after catching his breath Sonic could finally speak."so uh, that was something." sonic said awkwardly scratching his quills at the back of his head. Tails didn't say anything he was a little shocked that he just had a make out session with his best friend, but he had no regrets maybe he could even get Sonic to take this a little further..."well hopefully you learned something from this lesson," Sonic said as he unlocked the door "lets never speak of this again by the way."before Sonic could even open the door to leave Tails stopped him by grabbing him by the shoulder"wait i still need you how to teach me to do something else." Tails said, not ashamed at what he meantTails let go of Sonic and the Hedgehog turned around not really suprised at what the fox said but him being Sonic wanted to tease him and see how far he could take this."what do ya mean pal?" Sonic asked in a dumb tone"i want you to teach me how to... you know...?" Tails didn't want to just ask Sonic to shag him it was just out of character."Tails if you wanted to fuck me you could of just asked." Sonic teased. Tails gave him an annoyed look and Sonic gave in. "ok fine but i don't see how i have to show you these things. you just stick it in the hole, its not that hard and aren't you supposed to be the smart one?" Tails sighed at Sonic's annoyance and started to take off his goggles and his belt he always wears. Sonic followed and took off his signature scarf and his gloves. The fox guided his hedgehog friend to his bed and Sonic wasted no time to get on top of him and proceed to hungrily kiss his lips earning a surprised moan from the younger. Sonic's hands trailed all over the fox's body from his furry chest down to his thighs, then he stopped at the place between his legs and started rubbing at his sheath, Tails pulled away from the kiss momentarily at the touch and moaned softly as his friend rubs at the slit to try to get his dick to pop out. seconds later tails's cock comes out of its hiding place and Sonic stares at it "what the hell?'' Sonic says and Tails is a little confused by his statement"whats wrong?" tails asked. was it too small? it wasn't his fault he was much younger than Sonic anyways."i always thought you had two dicks" Sonic laughed at his ridiculous assumption "what? why?!" "well y'know you have to tails so i kinda figured--""sonic that's disgusting!" a flustered Tails yelled and pushed a laughing Sonic off of him "why in the world would you think that?" Sonic didn't answer that question, instead he pulled Tails on top of him and went back to kissing him making Tails forget they even had that coversation. Sonic slipped his tongue inside of tails's mouth once again only this time he forced his tongue in the back of the fox's throat causing him to gag this turned on the little hedgehog and Tails felt his dick push in between his thighs.the two pushed away to catch their breath with saliva connecting to their lips. Tails wiped his mouth and looked down at Sonic who was a panting blushing mess. god, he looked great like this."so uh, what now?" Tails asked, not really sure what to "just fuck me tails," Sonic said sounding a little desperate "usually I'm top but i'll give you an exception since you're my best friend." "ok, but how?" Tails has seen porn before for scientific reasons maybe he could just turn Sonic around and fuck him but that seemed weird and unnatural, is that how guys did it?Sonic rolled his eyes forgetting about how stupid his partner is when it comes to sex. he placed his legs on tails's shoulders and lined his hole up with tails's dick."ok, when i say go just shove yourself inside me okay~" Tails nodded at the instructions given to him and placed his hands on Sonic's hips readying himself."ok, go--" and just upon hearing those words Tails entered Sonic not giving him enough time to ajust before he forced the whole thing inside of him. Sonic screamed and it was at this time he remembered he forgot to prep Tails and of course Tails didn't know you had to do that. Tails winced at Sonic's tightness and he painfully tighted his hold on Sonic's hips adding more the pain the poor hedgehog was experiencing. There was something sonic wasn't letting him tell Tails to pull out so he could lube himself, the pain felt great and his brain was telling him to just suck it up. tears were beginning to form at the side of sonic's eyes and tails felt like he was doing something wrong, he began to pull out and maybe listening to his dick rather than his brain was a bad idea, but halfway Sonic stopped him "i-its ok," Sonic said trying to wipe the tears away with his hand, "i'll get used to it now start rocking your hips" Tails still considered pulling out, he was now regreting letting Sonic have him top. maybe if Sonic took the role of being dominant it wouldn't of been so bad. Tails shook his head and began to rock his hips gently and loosening his grip around his friend's hips. it still hurt like heck in Sonic's end but he just had to relax and then he'll get used to it and it'll start feeling great. eventually sonic did get used to Tails's gentle motions and a small moan left his lips, but this wasn't getting him anywhere, he needed more!"Tails...go faster... deeper.. please" Sonic said in between breaths. Tails did so and changed his pace trying to move his hips a little faster. Sonic moaned and clenched the bed sheets but only louder in the chance of pace. Tails was having a great ol' time as well with little pants and moans coming out of mouth as well, everytime sonic clenched around him and everytime he made a little sound it made him feel great. "T-Tails..." Sonic cryed out and grabbed at the boy's chest "pull out and-- pull back...augh.. in it feels.. greAt" Tails did as requested and he slowly pulled out and slammed himself back into Sonic, the hedgehog let out a scream of pleasure and he gripped at the younger male's chest fur. Tails didnt like the fur pulling very much so he grabbed Sonic's arms and he put them over his head pinning him down with all force, Sonic's cheeks turned redder than they already were. "you're a little grabby and that's gonna get annoying." Tails said before pulling out again as he gripped hard onto Sonic's wrists and slammed himself once more into him hitting his prostate causing him to moan so loud the whole island could probably hear what they were doing.Tails continued this pattern of slamming into Sonic and successfully hitting his prostate each time. Tails went on to grab at sonic's dick and stroked it making the other moan. after a while tails felt a weird feeling at the bottom of his stomach. oh geez, he was about to cum."augh Sonic im gonna cum!" Tails moaned"ah, same here!" sonic said breathlessly. Tails came first, with him yelling Sonic's name and rolling his eyes at back if his head as he did so cringing hard at the intensity of his orgasm and the existence of this fanfiction. Sonic followed and came in tails's hand, mouth gaping open and his muscles tensing.Tails got off if Sonic laying down next to him gasping for air Sonic kissed the fox's forehead "no homo by the way." he said before getting up with shakey legs to go to the bathroom to clean himself up.Tails was so tierd he felt like jello and damn, fucking your best friend sure was tiring. his eyes started to close and he started to drift off to dream land, his bed was so comfy he could sleep for ages. but his plans came to a stop when he felt Sonic really close to his ear, "don't you have that date to go to?" Tails's eyes shot open.