Taking Chances: Ch 1 First Time

Story by the roo on SoFurry

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#1 of Taking Chances


Warning: 18+ Naughty Stuff

In a local supermarket, the constant beeping of the register was hypnotizing. Thick, padded paws were on auto-pilot as they grabbed items and ran them over the scanner. "Excuse me? EXCUSE ME!" Justin's foot long ears tipped, the roo coming out of his zombie like state. A somewhat frustrated she-fox was calling to the cashier in his blue collared shirt and tan cargo pants. "Yes, Miss?" The middle age fem with short brown head fur and glasses stared at him curiously, "You scanned some of my items twice, hun." At least she was nice about it. Some people just freaked out and started yelling at him. "I apologize Miss." She clicked her tongue and smiled, "You're such a polite boy. Having a long day?"He nodded and smiled with a blush, "Yes."

After she had just adjusted his mistakes, the brown and gray furred bear in her collared shirt noticed the roo's ears drooping again. It warned her that he was nodding off while standing at his register, AGAIN! Walking away from her manager's podium, Jackie grabbed Kylie, another roo coming off her break, and took her over to Justin's register. When he was done with his latest customer, "Justin, Kylie is going to come in so you can take your lunch break." she said in her rough, smoker's voice. The roo was all too eager to get his apron off and take his break. But as he stepped out of the register, she grabbed his arm and grumbled, "...And I suggest you take a nap while you're gone."

Justin dragged the ankles of his large sneakers, walking out the front door of the market. He was so tired and his backside ached so much, he was ready to lay down on the break bench just outside by the soda machine next to where they lined up the carts. Taking a seat and tucking his tail beneath the bench, the roo rested his long muzzle in his palms. His eyes darted across the parking lot, watching the cart pusher, Mark, pushing the carts back and forth. He couldn't help but watch with a blush on his tan color cheeks as the black cat with white paws and a single white tipped ear bent over the carts to attach the cable to pull them. As soon as the cat's white briefs tightened around the male's bubble butt cheeks, Justin nearly melted on the spot.

All of a sudden there was a grunt and the roo jumped, nearly falling off the table. Standing over him was a thin, adorable lion with a feather light dirty blond mane, wearing the same uniform as Justin. "Oh god...it's the sexy feline bagger..." he thought to himself, tensing up. "Do you have a crush on Bryan or something?" Justin flinched at the question as the lion's eyes narrowed and pierced into him. "What do you mean?" he stammered. The lion nodded towards Mark out in the parking lot, "Do you have the hots for Bryan?" Just then looked out towards Mark, "That's not Bryan...that's his twin brother, Mark." He struggled to swallow as the male stared at him, "You...you can tell by the white blotch on the tip of his right ear..."

The lion's maw curved into a grin, "I didn't know they were twins..." He tucked his leg under the bench and sat down next to the roo, sizing up the average sized male. "...would make things interesting, wouldn't it?" Justin ears twisted in a perplexed way, "What do you mean?" The lion scooted forward, "You're gay, right?" Justin nearly choked on his own tongue, shocked, being asked that for the first time. He saw the look on the marsupial's face, "Oh don't worry, I am too." he said in his very feminine voice. The lion only smiled, "My name's Jeremy."

The roo hesitated, but he finally managed to utter his name, "Justin..." He was clearly shocked that someone would just openly admit that they were gay. The last time he tried to come out to his parents, they told him how looked down upon it was to like other guys. But here was this lion, just sitting there, talking about doing gay stuff. For most of it Justin just listened. "Look...Justin; I think maybe you should come with me to the festival tonight. You can see what it's like to let loose and have a little fun..." The roo's heart was pressing against his chest, not only excited to meet another gay male, but to get to hang out with him too. "Sure! What time? What's your address?" As he keyed the lion's information into his phone, Jeremy stood up, "Hey, I got to get going now, but remember, six forty five, don't be late."

The excitement built up in Justin's chest even more as he hurried home on his bike, not have a license to drive just yet. Bursting through the door of his two story house, he rushed passed his mom in the kitchen, heading for the stairs. "You're home early, aren't you?" she asked. "They let me leave early!" When he reached the top of the stairs, he dashed into the bathroom, jumping in the shower, scrubbing every bit of his body and washing every patch of fur. After showering, he got dressed, making sure to wear his nicest summer outfit. He didn't know why, but he wanted to impress Jeremy. As fast as he had arrived at the house, he'd left, gliding down the hill that led to the lion's neighborhood, coasting almost the entire way.

Ringing the doorbell of Jeremy's small, two story house, and the lion greeted Justin with a smile, wearing his own light summer clothing with his bare foot-paws touching the floor. "Come on in, we just have to wait for my friends to get here...we'll be hitching a ride with them." He led the roo into the nearby TV room and welcomed him to sit on the brown, cushiony couch. "Is there anything you'd like to watch?" Jeremy asked, turning on the TV. Justin watched as he turned it to some reality TV show. The roo didn't mind them, but he didn't love them either. "Not really..." Jeremy realized that Justin was one of those people who someone just had to peel the layers off of. Thirty minutes went by. Then an hour, and then two hours. "When are your friends suppose to come?" Justin asked, feeling himself start to nod off. "They were supposed to be here by now..." As Jeremy got up and started dialing on his cell, Justin's eyes slowly closed and he leaned his head on his right shoulder.

The next time Justin opened his eyes, he looked out the window behind the TV, noticing that it was already dark out. "Wha...its dark already!?" He suddenly felt something scratching at the base of his ears. Somehow he had been sleeping on Jeremy, the skinny male having his arms wrapped around the roo's shoulders, his tail wrapped around his waist. "Jeremy?" He was shaking as the lion's paw slid up the back of his shirt, working down his back, sneaking into his pants, massaging his padded fingers around the roo's thick tail. "Jeremy..." he muttered, leaning his head against the male's chest, nuzzling into him as the lion took complete control of him.

Jeremy gently maneuvered Justin onto his back, the roo sinking into the material of the couch as the lion lay on top of him. He gasped as he felt the male's body press into his, feeling Jeremy's sharp teeth nibbling at the spot between his neck and shoulder. Hesitating as he reached up to touch him, the roo felt around Jeremy's back until he was grabbing the lion's soft ass, running his fingertips through the tan fur. His eyes widened as he felt something round and solid running over his tongue, the roo blushed when he finally realized it was a tongue piercing, nestled in the center of the lion's sandpaper like tongue.

The male then took the roo's paws, placing them on the front of his jeans and Justin eagerly started to undo the button. Both managing to get their pants off, they grinded against each others' cocks, Justin's thicker with his slippery roo shaft, Jeremy's longer, curved with a barbed head. The lion took a hold of both their cocks, roughly jerking them, sliding his fingertips down to Justin's pulsing sac as it hung over his raging hard shaft. He pushed his paw along the roo's shirt, pushing it up so that he could get at the male's hard, excited dark nubs on his chest with his maw, forcing a moan from Justin as he nipped at the bit of flesh with his sharp teeth.

Justin's big toes curled as Jeremy pulled him closer, his legs pulled around the lion's waist. He gasped, the lion putting his thick roo tail to the side, fully exposing his tail hole, touching his barbed head to Justin's pink, virgin pucker. "Do you want to do this?" he asked, looking into the roo's nervous eyes. Justin took a moment to seriously think about doing this, "What about a condom?" Jeremy gave a smirk, "Don't worry, I'm clean." The roo felt like he didn't have long to make the decision, too eager to have his first time, "Yeah...I wanna do this."

Jeremy placed his paw to his maw and gave it a good lick before putting his palm to his aching barbed head. Justin braced himself, gripping the sides of the couch and curling his toes. He took a deep breath, he cried out as he felt Jeremy's naturally lubed head break his pucker. The pain of his first time took him by surprise. And then he was completely caught off guard as the lion bucked hard into him. Whimpering a looking up at Jeremy as his hole burned, he placed his padded palm against Jeremy's flat stomach, trying to stop himself from begging the hot male to stop.

The roo gasped, his large foot-paws bobbing in the air as Jeremy propped his ankles over his shoulders, pounding away at Justin's hole. Justin's jaw hung open as his ass suddenly went numb, gripping the sides of the couch. His moans became louder the deeper Jeremy's stiff cock seemed to go. The roo started to feel the lion's head brushing against his prostate. Crying out hard, he pushed hard against the lion's crotch, locking his ankles around Jeremy's ass. Breathing hard a loud, he threw his head back, feeling cock spasm out of control. Throwing his hips in the air, he was breathless as he shot his load all over his thigh, strand after strand of jizz running down his leg.

Jeremy drove himself to finish, tapping Justin's ass fast and hard. Reaching out to the roo's chest, he held on tight, feeling his sac churn as he tapped against Justin's butt. His body tensed up as he felt himself getting close. Justin lay there, dazed from his first orgasm with another male, enjoying the feeling of the barbs of Jeremy's cock brushing against his insides. Throwing his head back, Jeremy grabbed onto Justin's hips, thrusting hard and shooting his load deep into the roo. Justin moaned, letting his jaw fall open as he felt the air rush over his wet hole as Jeremy pulled before thrusting back in. Completely overwhelmed by the amazing feelings inside him, the roo laid his head back, easing back into sleep as the lion fondled the spent stud's cock.

When they were dressed again and waiting outside, Justin felt like Jeremy was keeping to himself. It was like the lion didn't want to talk to him after what they had just done. He stayed on the left side of Jeremy's garage door and the lion was on the right, smoking a cigarette. It was awkward for the roo, standing there, his hole wet and his insides warm. He had to keep his tail tucked to keep so that he could keep his used hole tight.

Suddenly a car pulled up and Justin was shocked to see who was stepping out of it. Other than a gray and black furred female canine with flowing black hair, a big bellied gator with bronze and swamp green scales stepped out and the car lifted up. The gator's name was John, someone Justin couldn't stand in school. As they locked eyes, the gator's size wasn't what the roo was afraid of, the scaly more fat than muscle. No, it was the gator's big mouth he couldn't keep shut...