Obligatory Content Warning: The following story contains EXPLICT GAY SEX between HIGH SCHOOL STUDENTS.  If this offends you, DO NOT READ ON!!!  By reading beyond this point, you waive your right to be offended by my work, because YOU WERE WARNED!!!  Now, for those of you I haven't scared off... enjoy!

Keith cursed under his breath as he stood at the urinal, his sheath in his paw.

"What the hell do I need to know about chemical bonds for?" he muttered.  He let out a soft sigh as he relieved himself.

The raccoon's ears perked up as he heard the door open, and he looked in time to see the newcomer walk right in and stand before the urinal closest to the door.

Keith's jaw dropped.  It was Damon, a coyote who lived in his neighborhood.  He'd had a crush on the coyote since middle school, though he had never yet worked up the courage to talk to him.  He was quite sure that the coyote didn't even know he existed.

The raccoon stared, enthralled, as Damon took a spot at the next urinal and started to relieve himself.  He stood a full head taller than Keith, not surprising, considering the raccoon was only a fourteen year old freshman, and Damon a senior.

Damon glanced over at the coon as he zipped his pants up.  "Hey," he said, casually flushing the toilet as he walked to a sink.

Keith blushed and zipped his pants hurriedly, then rushed over to a sink to wash his paws.

The coon struggled to work up the courage to talk to the coyote.  "Hey, Damon," he said.

The coyote didn't look up as he finished washing his paws.  "You're name's Keith, right?" he said suddenly.

Keith blinked, caught unaware.  "Yeah," he said.  "How did you..."

"I know everyone here," Damon said.  "Maybe not personally, but there isn't a fur whose name I don't know.  Besides, you live near me."

"Yeah," Keith said as he finished washing his own paws.  "So..." he said, watching as the coyote rubbed his paws under the drier.  "Umm... you doing anything after school?"

Damon growled as he finished drying his paws on his jeans.  "Damned things never get your paws all the way dry," he muttered, before turning his attention to the coon.  "I've got some lines to practice for theatre class after school," he said.  "You're welcome to come over, if you want to help me learn them."

Keith caught a yelp of glee in his throat at the words.  "Really?" he said, his eyes wide in disbelief.

"Sure," Damon said.  "I need someone to practice with, and most of my friends are busy after school today.  Drop by sometime," he said, and before Keith could reply, the coyote swept from the bathroom.

Keith had to dash into a stall and sit down on a toilet to keep himself from whooping in triumph.  He took a few moments to get control of himself before getting up and leaving the restroom.

The rest of the day went by in a blur for the raccoon as he fantasized about the coyote.  His erection straining against his jeans as he thought of Damon didn't make it any easier to focus on his classes.

Keith was in a similar fog on the bus ride home.  When the bus reached the end of his street and dropped him off, the coon practically sprinted back to his house to drop off his backpack and watch for Damon to drive back home.

He burst through the front door into the empty house and ran right up to his room, throwing his backpack onto his bed before rushing into the bathroom.

The tap squeaked as Keith turned on the cold water and splashed his face a few times.  "Be cool," he muttered to his dripping reflection.  "You may not get another chance like this.  Don't blow it."  He grabbed a towel and dried his facefur vigorously, and was just patting it down when he heard a car honking outside.

Keith dashed downstairs and looked out the window.  His jaw dropped as he saw the familiar red Mustang sitting out front, Damon behind the wheel, looking at the house, waiting.  The raccoon burst out the door, nearly forgetting to close it behind him, and ran up to the car.

"Damon!" he said, trying not to sound too excited to see the coyote.  "What are you doing here?"

"I'd wanted to offer you a ride home," Damon said, smiling mischievously, "but you left school before I could find you."

Keith blushed a bit.  "Yeah.  I was a little... distracted," he said.

Damon chuckled and shook his head.  "Well, if you're not busy now, hop in, and we can head back to my place," the coyote said.

"Sure!" Keith said, and got into the passenger seat, gasping as Damon started driving before he'd even shut the door all the way.

Granted, it wasn't a long drive.  Thirty seconds later, the car was parked in Damon's driveway, and the coyote twirled his keys on his finger as he waited for the raccoon to get out of the car.

Keith followed the coyote to the door and into his house.  His heart was aflutter as he looked around.  Damon plopped his backpack down on the couch, and Keith yelped softly as Damon flung a script at him.

The coon's paws fumbled for the script, and he managed to catch it before it fell to the floor, earning a chuckle from the coyote.

"Open up to page fifty-seven," Damon instructed as he pulled out his own script.  "I need you to read the part for the Amy, the female lead."

"O-ok," Keith said, slowly opening the script.

They started to practice lines, and Damon growled softly and threw his script down.  "You know what?  I need you to get into character so I can do this," Damon said.  "Why don't you go up to my sister's room and put on some of her clothes."

"What?!" Keith said, startled at the request.  "Umm... sure... where's her room?"

"Top of the stairs," Damon said.  "It shouldn't be hard to find.  It's the pink one."

Keith gulped.  "And... your sister... won't mind?"

Damon laughed heartily.  "She's spending the night with a friend.  She'll never know!"

"Alright," Keith said, the script held tight in his paws as he slowly ascended the stair case.

"I wanna do Act Two, Scene Four when you get back, so be sure to check that!" Damon called after him.

Keith took a deep breath as he walked down the hall.  He found the pink room, just as Damon had said, and walked in, opening the closet and looking inside.

As he perused the clothes, he thought about what Damon had said.  'Of course his sister would be gone... she's the most popular girl in class.  Probably has a dozen friends to sleep over with,' he thought as he pulled out a spaghetti strap top and a skirt.

He held the clothes to his chest.  Sure enough, it looked like the coon could easily slip into Damon's younger sister's clothes.  He blushed as he undressed right there in the middle of her room, removing his jeans and t-shirt and replacing them with the skirt and top.  He looked at himself in the long mirror on one of the walls, and blushed deeply.  'I wonder if Damon will think I'm sexy...'

He contemplated pulling on a pair of the girl's panties, to complete the illusion.  His footpaw tapped the script, and he picked it up and briefly skimmed the act that Damon had said he'd wanted to do.  A small gasp escaped the raccoon's lips as he saw that there was a kissing scene in the aforementioned act, and his blush deepened as he felt his briefs getting tighter at the thought of kissing Damon.

Keith made up his mind.  He put down the script, pulled off his briefs, and dug through the dresser until he found a pair of pink panties.  He pulled them on, grabbed the script, and started back downstairs, stowing his clothes in the upstairs bathroom before returning to the living room.

Slowly, the raccoon walked back downstairs.  As he reached the bottom of the stairs, Damon got up from the couch and grinned at the raccoon.

"Perfect," he said.  "You make a beautiful girl," he said with a barely concealed snigger.

Keith felt his face burn under his fur as he stood before the coyote, and he opened his script.  "So... wanna start?" he asked.  "Act Two, Scene Four, right?"

Damon stared at Keith for a moment, then nodded.  "Alright," he said, opening his script.

Keith timidly opened his own script to the appropriate page and waited for Damon to begin, shivering softly in a mix of cold, embarrassment, and anticipation.

"But, Amy," Damon said, the script held in one paw as he approached.  "You know you're the only one for me."

Keith swallowed as he began to read the lines.  "But... after s-seeing you w-with Brenda... h-how can I t-trust you?" he stammered, blushing hotly as the coyote approached.

The coon shivered as Damon put an arm around his waist and pulled him close.  "I love you," Damon whispered, "And if you can't trust my words... trust in our love."

Keith barely had time to glance at the script before he felt the coyote's lips pressed to his.  His eyes fluttered shut and the script fell from his paw as he wrapped his arms around the coyote and parted his lips slightly, hoping beyond hope that Damon would deepen the kiss.

In a flash, Keith's senses were overwhelmed as, in a moment, he felt the coyote's tongue slip past his lips, one paw cupping the back of his head as the other grabbed his ass.  He let out a soft, pleasured moan around Damon's tongue as the coyote pulled him close.  Keith could feel Damon's toned body against his slim chest, and his stiff erection pressing against the coyote's thigh.  He imagined, or rather hoped, that Damon was just as hard as he was as his soft tongue made contact with his.

Time stood still for the raccoon as he stood there, wrapped in the arms of his secret crush.  He whimpered as he felt Damon pulling back from the kiss, and gasped as he felt the paw on his ass move to his crotch.

"Feels like you're excited," Damon whispered.  Keith could only blush as the coyote's paw caressed him through the panties.  "Come with me," he said, releasing the raccoon and walking upstairs.

Keith followed obediently.  He wasn't sure what Damon was going to do, but after the kiss, he was willing to go along with anything.  He briefly wondered if Damon had really meant what he said as they walked into the coyote's room.

The coon stood in the middle of the room, clutching himself, waiting for Damon to do something, say something, anything.  His eyes scanned the room, but nothing sunk in.  All of his senses were reserved only for Damon.

Keith gasped as he felt the coyote's paws on his shoulders.  Next thing he knew, the panties he had put on were around his ankles, and Damon was holding him from behind, nuzzling his neck as his arms wrapped around Keith's waist and held the coon close.

He felt Damon straighten up behind him and lay his chin on atop his head.  "Keith," Damon whispered, grinding his crotch into his lower back.  "Do you feel that?"

"Y-yes," Keith replied, leaning back to feel the coyote's erection against his back.  He imagined what it must feel like for him, the throbbing coyote cock straining against his jeans.

One of Damon's paws grasped Keith's.  The coon felt something in it, and grabbed it as the coyote's paw pulled away.

"Put it on me," Damon whispered into Keith's ear.

The coon looked at the object in his paw.  His eyes went wide as he saw it, and he looked up at Damon.  "Do... do you..."

Damon pressed a finger to Keith's lips, silencing the coon.  He pointed downwards, and Keith followed his finger.  He gasped as he saw that Damon had already unzipped his jeans, and his red cock was out, a drop of pre at the tip.

Keith dropped down to his knees as he stared at Damon's cock.  It wasn't quite as big as he'd imagined, but it was still plenty big enough for the coon.  He leaned in and tentatively licked the drop of pre from the tip, earning an appreciative moan.

Slowly, Keith leaned in and took as much of the thick coyote cock into his muzzle as he could fit, the condom forgotten in his paw as he savored the flavor of Damon's flesh.

"Mmm... you like having my cock in your mouth?" Damon whispered between moans.

Keith nodded his affirmation as he swirled his tongue around Damon's shaft.  He shut his eyes as he savored the sensation, his secret fantasy fulfilled as he felt a throbbing cock in his mouth for the first time.

His first attempt at oral was short-lived.  With a grunt, Damon pushed Keith's head back from his cock.  "Aren't you forgetting something?" Damon said.

Keith looked up at him, then back down at the condom in his paw.  "Oh..." he muttered.

"Stay there for a moment," Damon said, as he took a few steps back to his bureau.

As he waited, Keith fumbled with the wrapper, his paws shaking as he freed the latex condom from its plastic prison.  He gasped as he saw Damon standing before him again, his cock waiting.

"Don't forget to pinch the tip," Damon said as he stood before the raccoon, awaiting the latex sheath.

Keith gulped and nodded, pinching the tip and panting as his still-shaking paws unrolled the condom over Damon's waiting cock.  He felt it throb in his paw as he put the condom on, and looked up at Damon as he finished.

"Good," Damon whispered, putting his paws gently on either side of Keith's head.  "Now get on the bed."

Keith looked up at him, still blushing deeply, and, guided by the coyote's strong paws, walked over to the bed.

"Get on your paws and knees on the bed," Damon whispered.  "And lift that cute tail of yours."

The coon blushed deeply under his fur as he listened to the coyote's instructions, and he did as he was told, crawling up on the bed and kneeling, his ass held high, his tail swishing slowly above him.

He felt the bed shift as Damon got on, and shivered as he heard the sound of a bottle opening behind him.  "Just relax," Damon whispered.

Keith gasped as he suddenly felt a cold liquid against his pucker.  He squirmed as he felt Damon's finger rubbing the liquid all around, and whimpered as the finger pushed into his tight, virgin pucker, spreading the cold liquid deep inside him.

"C-cold," Keith muttered.

"It warms up fast," Damon replied.

Keith shivered as he felt a second finger penetrate his tailhole, slowly spreading it.  It was a curious feeling, having the coyote's fingers in his tailhole, a little painful, but not overwhelming, and the feeling of closeness to the 'yote left butterflies in Keith's stomach.

And then it was over.  Keith whimpered softly as he felt Damon's fingers leave his ass, and was about to protest when he felt something much larger poking at his hole.

Keith shivered as he felt Damon leaning over him, gripping his hips.  He felt the hot breath of the coyote against his neck, and heard him whisper, "Try to relax."

Keith gasped and bit his lip to keep from screaming as suddenly his tailhole felt like it was on fire.  He whimpered loudly, barely registering Damon's grunts as he invaded Keith's tailhole.  The coon saw stars before his eyes as the coyote pushed in, the pain making his eyes water.

"Mph... tight," he heard Damon mutter.  "Dude, seriously... relax... it'll make it easier for both of us."

With another grunt, Keith felt Damon's hips meet his.  He whimpered softly as he felt the coyote's balls, hanging out from his jeans, slapping against his from behind.  He struggled to control his breath and tried to relax as Damon instructed.  Keith felt Damon's paws gently stroking his sides and belly, and he started to relax under the gentle attentions of the coyote.  Sure enough, as he did, the pain lessened, though his tailhole was still sore from being so stretched.

As the pain lessened into a dull ache, Keith felt Damon pulling back.  He bit his lip, wondering whether Damon was going to pull out or continue.  His question was answered when, with a grunt, Damon thrusted back it.  It didn't hurt as much this time, but he still couldn't get over the soreness of his tailhole.

Keith gasped as suddenly, he felt Damon's paw wrapping around his cock.  He panted and moaned as the coyote started thrusting into him slowly, rubbing his cock in time with his own thrusts.  Keith shivered as a feeling of pleasure starting building, dulling out the pain as the coyote rubbed his cock and picked up his pace of pounding into his tailhole.

"You're not as big as I thought," Damon whispered into Keith's ear, making the coon blush deeply.  "I like."

As Keith struggled to register these words, he felt the coyote picking up pace, and something large pressing against his tailhole with each thrust.  From the pictures he'd seen online, Keith knew that canines had knots, and his eyes widened as he realized that Damon might try to tie him.

Damon let out an ear-piercing howl as, with a powerful thrust, he forced his knot into the coon's tight ring.  Keith's vision blurred as a wave of pain mixed with pleasure flooded his body as the thick knot penetrated his already-sore ring.  He whimpered as he spilled his own seed onto the bed below him, his senses overwhelmed by all of the feelings.

Damon collapsed onto his side, clutching the exhausted raccoon to his chest.  Keith flicked his ears as he felt the coyote licking them.

"We'll be like this for a while," Damon whispered.

"I don't care," Keith replied.  "Damon?"

Damon's paws rubbed over Keith's stomach and chest slowly.  When he didn't reply, Keith went on.

"I... I love you, Damon," Keith whispered, wincing a bit as Damon bucked his hips forward, causing another dull ache in Keith's stretched out hole.

Damon's breath came hot against Keith's ear, and he whispered something that made Keith's heart stop.  "Love you, too, babe."

Keith wriggled against Damon.  He heard the coyote groan as he wiggled around on his cock to face him.  "You... you mean that?" Keith asked, looking into Damon's eyes.

Damon smiled and nodded, and leaned down to plant a tender kiss on the raccoon's muzzle.  "I've watched you for years... gotten to know you largely by asking around... I wanted you... more than I've ever wanted anyone."

Keith nodded and rested his head against the coyote.  "Why me?  You could get anyone..."

Damon kissed the top of the coon's head.  "But I wanted you... you're everything I could want... and now you're mine."

Keith grinned and nuzzled Damon's chest, hugging tight to the coyote, enjoying the warmth.  They remained like that for a while, until Damon's cock softened and slipped from Keith's tailhole.

Damon stood up and stretched, leaving Keith on the bed for a moment, and looked at him.  "Looks like we need to clean you up," Damon said, slipping out of his clothes.

Keith blushed and looked down at himself.  Sure enough, his own seed was matted against his crotchfur, and the lube left the fur around his ass equally disheveled.

"I'll see you in the shower," Damon said with a wink as he walked out.

Keith grinned and leapt up, throwing off the top and skirt, and followed the coyote out to the bathroom.