His Extreme First Time: Four Extreme First Times!

Story by the roo on SoFurry

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#3 of His Extreme First Time

Been wanting this toy action for atleast a month now! Enjoy


Warning: 18+ Naughty Stuff

Night One:

On a normal, every week day night, Artie lay down in bed. That natural feeling was calling to him, the head of his big throbbing lion cock poking out past the rim of his green workout shorts. Groaning and growling playfully all at the same time, he pushed those shorts down past his thighs as he tweaked at his right nipple and roughly fondled his balls before stroking along his shaft. There was a big grin on his face as he continued to stroke, his eyes half lidded, catching the light flicker of the light coming off the TV, the sound on mute. He didn't need porn to jerk off while he had his imagination. He just thought of sick dirty thoughts, just like how he was imagining three other males banging his girlfriend. There was a rough looking Doberman going at her pussy, a big looking stud fucking her ass, and a busty looking hyena gagging her with his barbed cock. What could he say; his mind was a freak show.

It was getting late into the night and Artie felt frustrated as he stroked over his thigh and aching cock at the same time. But no matter how many dirty cunts, yeah fuck her asses, or other dirty talking, he couldn't seem to build himself up. "What is wrong with me tonight?" Soon he started pumping fiercely, growling, baring his teeth. After forty five minutes, nothing. After forty five minutes, his wrist even started to hurt. The muscular lion suddenly kneeled on his bed, tweaking his nipple harder and stroking himself once again. Turning his head to see himself in the mirror on his dresser, he realized how stupidly desperate he looked. He was confused, he felt that usual aching feeling between his sac and his asshole...but he couldn't satisfy himself.

You know where it's coming from.

He question himself, "Huh, what?"

You know where it's coming from. You should focus back there than up front...

Artie's natural curiosity got the best of him and he suddenly found himself sliding his right paw along his butt... a single padded digit stroking over his extremely tight virgin pucker. As he tickled his circular, pink rim, it sent an almost orgasmic jolt through his body. He quickly pulled the finger away, "Nah nah, I've never wanted that before..."

Why not? No one is watching...

"But...but...I'm not gay..."

So? It's not like you're asking some guy to put it in your butt. It's just you here, all alone, like a hundred times before.

Artie hesitated, his finger hovering over his asshole.

Try it!

He clenched his maw, wondering if it would hurt a lot.

Do it!

Artie gasped, sucking through his teeth as he pushed his middle finger as deep as his tight pucker would allow. For a split second he felt a sudden relief from that aching feeling, but it was overwhelmed by a burning pain as his rim tightened around his knuckle. Hissing, he pulled it out, "It hurts!"

Get lube dumb ass!

His paw shaking, Artie pulled a bottle of lube out of his top dresser drawer, usually for when his girl was really tight or when he wanted a little more encouragement while jerking off. Twisting off the blue cap, Artie found himself uncontrollably drenching two of his thick, padded fingers. Panting hard, he ran his free paw through his short, black mane that flowed down into a chin strap beard as he position those two fingers against his wanting hole. Grunting in pain, he slowly slid the fingers deep into his bowels, his jaw hanging open. He nearly collapsed forward, forced to hold himself up as the pressure in his virgin ass felt like something had plowed into him.

Artie moaned uncontrollably, sliding his fingers in and out, pushing them even deeper each time until he found that amazing little G-spot for males. "Oh fuck!" He worked hard at his hole, pumping in and out until finally, he willingly slipped in another finger, his shortest finger and thumb tapping at his toned butt cheeks. When he was all well worked, the lion stud slid his fingers out before shoving in his thumb, his other digits working at his teint as he jammed his thumb over and over again against his prostate! "Feels...good! GAH!" As a single thick drop of jizz fell to his bed, Artie cuffed his free paw under the barbed head of his cock, feeling a heavy strand of jizz shoot out of his dick every time he smashed into his insides with his thumb. Gasping out of pure release, Artie pulled his thumb out, his asshole throbbing, expanding before tightening, aching in a relieved way from the new experience. The lion kneeled there, his paw full of cum, gazing up at the ceiling.

All of a sudden a thought passed in his head, You know what might REALLY feel good...?

Day Two:

It was a month later, and Artie was sneaking his way into his room. It was during the day and he had decided to skip school. Luckily his mom didn't come home till late and hopefully she would never find what was in the brown paper bag with the bird and bee on it. He was so eager to pull it out of its bag; he didn't even take his sneakers off as he pushed his shorts down to the floor. As his cock bobbed and hung half way down his thighs, Artie climbed onto his bed. Reaching into the bag, he dropped it on the floor as he pulled out a somewhat pink colored rubber, human dildo. It was about seven inches in length and two inches in girth, completed with the mushroom like head. He even noticed the thick, detail veins running along its side. This was the replacement for his fingers...which had for some reason failed to satisfy after a while like jerking off. He hoped it was worth all the time and money he had spent convincing the porno store guy to let him have it... he was just under eighteen.

Starting to pant wildly as he thought of what he was about to do, he dropped the dildo on his bed, his fat cock dripping pre as he reached over to his dresser and pulled out the huge bottle of lube that had replaced the previous empty one. His paw shaking, he flipped the cap with his thumb and licked his lips as he watched the clear liquid slowly drip down that rubbery shaft. Breathing sporadically, Artie kneeled on his bed, squatting his slightly stretched hole over the mushroom head of the dildo as he positioned it just beneath his butt. Taking in a deep breath, he gasped, nearly choking on his tongue as the head of the toy pushed pass every muscle behind his rim.

It was different, compared to his fingers. There was an immense pressure and he could feel the head driving up into his insides. At one point, he forced himself down too hard and he cried out in pain. Gasping, slowly... ease yourself onto it! But as the pain slowly died away, the lion moaned, lifting his ass up and down, feeling the dildo slide out of his butt with the help of the lube. Pleasured by the rubber rod pushing against the walls inside him, his whip like tail smacked against the bed. By the time he had adjusted to it, he was smashing the mushroom head into his g-spot. Curling his toes, he nearly went cross eyed as he burst out a moan, furiously stroking his cock, spraying all over his chest. Stroking himself none stop, he suddenly wanted to cry out, but slapped his paw over his maw, looking at himself in the mirror as he rode the human dildo, cum dribbling over his fingers...

Day 3:

It was a boring day at college as Artie sat in class. He was leaning against his desk with his ass back against the seat. Struggling not to moan out loud, he felt his jeans pressing against his stretched asshole, which had long been expanded by the various toys he had bought over the past year. Panting, he touched his book bag, barely concealing the new toy he had picked up earlier that day, its head straining against the material. Biting his lip, he felt his cock head poke out of its sheath. Desperately thinking to himself, he grabbed the bag, "Fuck it! I need this now!" Huffing, he ran out of the class room, forgetting most of his books, trying to get to the bathroom before his cock tented in his pants.

Slamming open the bathroom door, Artie checked all the urinals and the stalls before rushing into the handicap stall. Panting hard, he unzipped his bag and wrapped his paws around the pointed shaft with a pinkish tip and purple coloring at the base, lines of spike like ridges along the shaft. The tip of the dragon cock was already dribbling cum lube from the mere touch of his paws. Staring at it, he admired the sheer size and design of the toy before he got to his knees, pushing his jeans to his ankles as he placed the flat end of the cock against the bathroom wall. Excited beyond belief, the lion moaned, feeling that wet, cum covered tip push into his stretched hole, "Mmph!"

It felt utterly amazing as he slid back on this thirteen inch cock, feeling its ridges pushing against his walls. Once he had found his stretching point, Artie moaned, moving his strong hips until the toy was making wet slurping sounds in his butt. "Oh yeah..." His pounding back on the wet rod grew faster, harder as he adjusted to it, stretching himself even further. Panting, he felt his cock jump each time that rod pounded into his stomach. With a loud, lust filled grunt, he couldn't contain himself anymore, he loved it up his ass, "Ungh FUCK ME! FUCK ME HARD!" His girlish cries for cock drove him over the edge and he was suddenly shooting load after load onto the tile floor. Collapsing forward, the dildo fell out of his ass as he rapidly jerked his dick, reaching around to finger the gaping hole which was his rim, loving the feeling of being wet and stretched. He panted on the floor, slowing his jerking pace, moaning each time he felt a breeze in his stretched butt as cum lube dribbled down his ball sac and onto the floor.

Day 4:

It wasn't much longer before Artie walked into his room, carrying a large, seventeen inch package. Standing next to his bed, his foot-paws tapped against the mound of toys hidden beneath it. Some were canine shafts with knots, smaller dragons, barbed males, smooth orca cocks, glass human pricks, much of them still covered in cum lube after usage. But as the lion once again pushed his shorts down past his ankles, he stepped out of them as he grabbed hold of the box. A knot of excitement building in his chest, he slowly opened the box and pulled out the hug, leathery black, pink spotted horse cock waiting for him. Looking over his shoulders as if anyone could throw open his locked door at any minute, Artie gave the huge monster toy a gentle squeeze and a glob of thick, gooey cum dribbled out of the small, round piss slit at the tip of the phallus crown. Just the sight of that slick cum made his ass ache for cock.

Positioning it on the wooden floor, the lion literally had to spread his legs, positioning his butt crack over the phallus toy. He made sure it lube him up nice and good before he let out a heavy moan, feeling that knuckle like head spread his already stretched hole. Suddenly, that feeling of pressure from his first time with a cock came rushing back, like he had never taken a cock before. "Oh fuck...so...big!"

Only having a quarter of the monster cock in his ass and he already felt stretched. But he was determined now; he was going to take that cock up his ass! Whimpering, he had to reach back, holding the shaft up straight as he slowly lowered down onto another quarter of the dildo, feeling it stretch him further. Rapidly panting, he pushed himself, moaning at the amazing feeling coming from his ass, running up his spine, turning his nipples rock hard. When he was finally able to lower his knees on the hard surface of the floor, he looked between his legs, seeing there was only so few inches left, but he was satisfied with what he could take.

All of a sudden, as he moved an inch, he felt a large pop and an immense pressure and he cried out, digging his claws into his knees. With sweat building up on his forehead, he looked down to see an unfamiliar bulge in his abdomen. It seemed so unique to him, he started to ride up and down, noticing the bulge grinding against his abs. With rasping breaths he moaned, "Oh yeah, oh fuck!" He could feel the horse cock pumping the cum deep into his insides, feeling it slide down its shaft, smearing on his ass.

Pressing his foot-paws hard against the base of the leathery shaft, he threw his head back, supporting himself with his paws as he rode the cock non-stop. "Oh yeah, fuck me big boy!" The barbs on his cock flared, feeling the ring of the horse cock grinding against his prostate. "OH FUCK!" His cock spastically twitched, pushed past his limit, shooting hot strands of cum all over his face and maw. Even as he felt his load cum to stop, he continued to ride that monster cock, loving the feeling of a big, thick, wet rod grinding into his ass!

End.