Will Kisses Jailbait

Story by ewald on SoFurry

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#2 of Will Fucks Jailbait

What seems like a simple weekend job to grab more money takes a turn for the worse when Will ends up locked up alone with a horny teen for a weekend. And the boy has difficulty taking no for an answer.


Please leave a comment and a watch if you enjoy this!

Note: I don't condone the behavior Will espouses in this series. Part of my goal is to communicate how many shades of gray there are, how people can easily fall into temptation, how horrifying it can to be put in these situations, etc. I find that most stories that are ageplay-centric tend to take a lackadaisical approach that either unilaterally paints these relationships as positive or exploitative, or completely foregoes the moral issues.

Anyway--enjoy, you kinky fucks.


Dinner passed with only minor incidents. The thought of food had been enough to quench the fire in Will's dick and motivate him to say the word "No" sternly enough that the kid backed off, even if those accursed thoughts did keep bubbling up in his head whenever he let his mind wander.

He couldn't blame Alex entirely. The boy was just a kid. Will thought back to when he'd been fifteen, and he certainly wouldn't have understood just how horrifying it'd be for an adult to have a boy hit on them like that. At that age, Will had just been a horny little fuck jerking it three times a day, trying to get blown by all the gay boys in high school.

It was an hour later that Alex tossed something at him on the couch. Reflex took over and he gripped hold of it, then squinted at it. Some kind of narrow aerosol can, like for cleaner or air freshener or something of the sort, but he couldn't tell what since the label had been ripped off. He stared at it for a few moments before looking up at Alex's shit-eating grin. And--and, Alex wasn't wearing anything but underwear. Tight, pastel-blue briefs.

The realization had him go from zero to erect in seconds. The boy's eyes watched his groin and saw it all, and he cackled.

Will sighed, and glanced away. "This is... your toy, isn't it?"

"Yup," the teen said, dropping himself down on the couch.

"Could you put some clothes on, please?"

"Nope."

Will sighed and inspected the toy. Long and thick. "So, this goes in your ass?"

"Yeah. Feels real good. You wanna try it?" The boy sat up, then turned himself around so his chest was towards the cushions and his ass facing back. His pretty, firm rear, was just barely covered by those tight briefs. They hugged his contours so nicely. His tail lifted up, and... Will was staring longingly at some kid's shapely ass. And dear God, was it shapely. Will jerked his head away--Christ, he didn't want to look at that. He didn't want to face the reality that this half-naked kid's ass was probably the hottest thing he'd ever seen.

The boy pushed something else over at him: a bottle of baby oil. Will squirmed, huffed, and sighed. "No. No, no, no. I'm not..." He dropped the toy and the oil on his opposite side, and the boy thumped his ass back down on the couch again, crossing his arms and pouting.

"I can't," the teen said, miming his tone. Alex... crawled over his lap towards his opposite side, and picked back up his toy, now sitting to Will's right. Alex thumped the thing against his other palm. "Pussy."

Will looked the boy over. Alex was... a supertwink. Pretty, lithe, and with a surprisingly pronounced bulge in those briefs. "Jailbait little freak."

"It's, like... eight inches," Alex said. "I can totally take you. I meant it, I *am* a bottom."

Will reached over and tried to snatch the toy from the kid's hands. "It's dangerous to use that as a toy."

Alex held it back and above his head, grinning. "Pff, no it ain't."

"Yes, it is." Will growled. "Butt toys have a flared base, so they don't get stuck. That thing could slip inside you, and..."

Alex squinted, then grinned. "Yeah? Then why don't you give me a better toy to use, huh?" The kid's leg kicked out as he said that and brushed up against Will's straining groin.

Will's hips jerked back out of the boy's range. His eyes followed the curvature of the teen's slender abdomen, down towards his groin. "How many times do I have to tell you no," he said. "Put your fucking clothes on, it's..."

"You don't like how horny I get you, huh?" The boy was grinning.

"I hate it."

"You can't even look at me without gettin' hard."

Will's mouth opened to spit fire back at him, but the boy slowly brought the hand holding that toy closer to him. Will's eyes followed it, and... the cold metal of the makeshift toy touched his nosetip. The maned wolf found himself unable to move. This thing had been in the kid's ass, and now Alex was taunting him with it.

"Kiss it," the raccoon said.

And Will listened before he could stop himself: his tongue slipped out and gave a long lick to the boy's makeshift anal toy. One lick turned to two, then three... the maned wolf wasn't sure how long this went on for, just that, once his eyes re-opened, the brat had a shit-eating grin on his snout and seemed to be barely holding back a laugh. That was a power-drunk look on his snout, of a teen feeling in control for one of the first few times in his life.

"Are you jealous?" the boy asked. When Will opened his mouth, the jerk pushed the cold metallic cyllinder into his mouth, earning a prompt "Mmf" from Will. Will didn't particularly love sucking dick, but he sucked on this dumb kid's makeshift dildo automatically, while pre leaked into his pants. His hands gripped at the upholstery of the sectional.

He met the boy's eyes, and the can moved in and out of his mouth a few times before slipping free. Shame was a foreign emotion to Will, who was typically an unwavering bastion of confidence. "Very jealous," he said when he could, voice wavering.

"You don't have to be," Alex said. "You can fuck me so much better than this thing can, I bet."

Will closed his eyes and bit his lip. He wiped his mouth with the back of his hand to clean himself of drool. "When do you turn eighteen? I'll fuck you the second the clock strikes midnight."

"Fuck me NOW," the raccoon said, giving the adult a light smack atop the head with his toy. "That's in three fucking YEARS. I want it now!"

Will grabbed hold of the boy's toy and shoved it underneath one of the sectional cushions on his other side. He sat up straight, lips pulled back into a snarl. "Trowing a tantrum when you don't get a way? You fucking child."

"You're so turned on," Alex said. "Like. You want it SO bad, don't you?" Will said nothing, didn't even look at him, and the boy made a sound that was halfway between a frustrated whine and a growl. "It's--it's not fair! You want it, I want it, no one else is gonna know about it... why the fuck can't we just do it?"

"It doesn't--" Will frowned. "It doesn't work like that. You'll understand when you're older."

"Don't be a fucking dick," Alex said, then followed it with a cute growl. "It's just--I did everything right. I get you hard as fuck, you think I'm hot... and that's, it's not enough. Because I'm just too young? Like, I did the best I fucking could and it ain't ever gonna be good enough for you?"

Was the boy giving up? ...part of him really hoped not. The more sane part of him knew this was good, though. "...yeah. You're just too young. Sorry, that's the way it is." He grunted, his tongue struggling to form words.."You... make it hard to say no. I hate it, and it's uncomfortable. Because I can't say yes." Felt like he was talking over eggshells.

"But my parents--they..." Alex whined. "They never have time for me. And they don't let me go out, and they don't let me have friends over. I--I know I'm gay, but you're right, I've never... tried it before. But you're here, you're hot and you have a.... huge cock. Ten inches?"

Will thought back to how the adorable noises the boy made as he'd whispered those words into his ears. And that was when he realized they were back to square one again, both hard, both looking at each other, both clearly wanting to fuck. But something was different now.

Will tried to divert. "You should talk to them about how unhappy you are."

The kid guffawed. "Have you--oh my god, have you met them?"

Will's ears fell. "Is there--is there anything I can do to help? You know. Besides sex."

The boy came to sit beside Will. He was... nearly naked, still. The teen's hand reached over, but not for will's cock. Adolescent fingers gripped his wrist and pulled it in, guiding it to the boy's flat, slender belly. Soft. So soft. The raccoon's eyes closed, and he made the cutest little chittering sound.

In that moment, he saw a vulnerable boy who just wanted affection and attention, who didn't know any way to get it but acting out and seeking sex. A pit sank in his stomach. Should he fuck the kid? Would it help him? ...was Will just wrong and trying to justify his lust for jailbait?

His hand roamed the boy's abdomen, then moved up higher to his chest. He detoured to stroke along the developing curves of muscle on the teen's arm, then went up higher. The boy turned his head to the side, eyes still closed, and brushed his whiskers against Will's hand. The teen pushed his fuzzy head into those fingers, ears flickering now and then, then sighed in contentment.

"You're a very beautiful boy," Will said.

"I know."

Somehow, Alex ended up sprawled over his lap, facing up. The almost-naked jailbait boy of his apparent dreams was so vulnerable and exposed. Both hands explored the teen's body. The raccoon made little noises that grew louder the closer he strayed to Alex's groin, and those briefs could barely contain him. Boy was seriously huge. No joke, maybe just an inch or so smaller than.

"You have a seriously huge cock yourself, kid."

"You won't be bigger for long." Alex said that with a grin and a squirm of his hips. The grin went away when Will's hands neared his waistband, melting away into a moan and a cute boyish hump of his hips.

"I'm s-so hard," the boy said.

"I can see."

He stared at the boy's bulge. He imagined squeezing it. He imagined tugging it out and beating the kid off--more gentle than fucking him, certainly, wasn't it? He imagined pulling it out and blowing the boy right here. Hell, he'd make such cute sounds when he came. But he wouldn't be satisfied there--neither of them would be--and it'd only be a downhill slide.

Will wasn't a bottom. But the closet size queen in him, the part of him that liked at the very least frotting with something around his size, lit up. And maybe, just maybe, Will's tail lifted slightly.

"It's insane that you're fifteen and this hung."

Alex's loud confidence had drained, and all he could venture was a squeak. Will's hand pressed atop the boy's underwear, right beside that bulge, not quite touching it. He measured it out with his fingers. Seven, eight... nearly nine? At least eight. Hard to tell by eye, but shit. Kid was capital-H hung. Both sides of him were hot... even if Will absolutely did prefer the backside.

His hand moved past the bulge in those briefs (and the wet spot where tip of the boy's dick lay) to stroke along those thighs, and the other returned to the raccoon's beige midsection, giving his fur soft, gentle strokes. His hand came to the boy's sides, at which point Alex slowly sat up, facing him, sitting in his lap.

Will straightened and got both arms around the boy. Something was happening. The boy leaned in, and those pretty green eyes stared into his. Whiskers brushed against his nose, threatening to tug a sneeze out of him. Alex's eyes were pretty. So pretty.

Alex wanted to kiss him. The boy was inexperienced, didn't know how to do it. He wanted Will to take the lead. Will wanted to kiss him. Fucking an underaged boy was a no-no. Kissing one? Enough of a gray area that his brain lagged just enough to convince him that yes, he could teach this kid how to kiss. His tongue flicked against Alex's nose, then they met together.

Awkward, at first, but damn was that whine cute. Will's brain watched with horror as, just like with the kid's toy, one kiss turned to another, to another, to another, to five more, ten more... and they were sprawled out on the couch, tent against tent, and Alex was so, so greedy for them. So vocal, all those little grunts and chitters.

It was only when Will lowered his snout and nipped firm at Alex's neck that he realized things had gone way, way too far. And in the moment he didn't care. Alex arched and moaned loud and it was fucking hot. The moan caught in his throat and two quick, huffy breaths followed it as Will's tongue traced up the fifteen-year-old's neck. Alex had leaned his head to the other side to bare his neck in utter, complete submission. His tongue trailed up to the teen's ear, then between them, then to other ear, then down to the other side of his neck... and then they were kissing again, hot and heavy. They couldn't seem to stop, mouths and tongues pausing only to breathe and pant. Bright eyes stared back into his, and Will couldn't look away, couldn't stop. God, he was cute.

It went on and on with building heat, and soon those boyish arms were wrapping around him and squeezing as two sets of hips frotted roughly together. Fuck, but this kid's dick was fucking huge. They dry-humped on the couch and Will's mouth just couldn't get enough of this beautiful teen and he didn't even like making out and Alex's hand was on his cock, and a hot, needy whimper melted into his ear:

"Please."

Greedy, teenaged fingers struggled to close around his throbbing dickbulge. Alex's other hand guided Will's hand down to his ass. He didn't even realize where it was at first, just copped a squeeze and--yeah. Boy butt. Of course. His middle finger ran down the crevice between those cheeks, blocked from reaching the kid's ring by his tight underwear. Still, the kid's back arched and that pert little ass ground back against him while its owner whimpered, and--

Reality hit him like a slap in the face and he stood, letting the kid (because he was a fucking kid for Christ's sake) tumble down to the ground. And of course, the first thing the dumbass raccoon was grab his bottle of lube and offer it up towards Will, and that made the maned wolf see red.

Will snapped. "Here I thought you were being sweet, but you're just a little fucking slut who wants to get fucked in the ass. You... fucking anal freak."

He spat the words, and Alex's brow furrowed. He wilted, dropping the bottle in his hands.

Fuck, what was he thinking, kissing jailbait? They must have made out on that couch for a good ten minutes straight. Maybe more. His eyes found the clock... twenty minutes?! The self-anger directed itself outward towards Alex, who quivered like he was on the verge of tears.

Will bent himself over to get on the boy's level. His hands rested on the boy's shoulders and he gave the kid a rough shake. "Can you go... Five. Fucking. Minutes. Without trying to get my cock in your ass, huh? Christ, you little fucking slut."

The boy shrank down until he looked like he were half his size, hugging himself. "I'm--I'm sorry. I--"

Will thumped down on the couch and rested his cheeks in his hands. "God fucking dammit, kid. I didn't..." He sighed. "Look. Why don't we both cool off, huh? You go to your room and... do whatever it is kids do these days. And I'll... take a cold shower. And..." He gripped his own fur a bit too tightly.

Things had all been fun and games up until this point, a nice little dance of him and this kid teasing each other, but this was... too real. He didn't want to be in the papers next week. He didn't want to warm a cell when this brat inevitably couldn't keep his mouth shut and his crazy overbearing mom inevitably found out the truth and used all those piles of wealth to hire the best damn lawyer she could to lock him up.

"I think--" Will spoke with as much confidence as he could muster, sitting up straight. "I should call your mom. I should tell her, I can't handle this. I wouldn't be the first, right? She can figure something out, I'm sure. I..."

"If you call Mom," Alex started, "I'll tell her."

Will froze. "Don't..." He felt cold. "Don't be a bitch. I told you, this isn't cool. I have to get out of here."

"Call her, and I'll tell you how we kissed. I'll tell her how you called me beautiful." He leaned in and sneered. "I'll tell her what else you called me."

"Alex, don't--"

The raccoon leaned in and got right in his face. "Mooom, he said I was an anal freak..."

Will took in a deep breath and balled up his fists. That was all he could do, because if he spoke up, he'd verbally eviscerate the little shit. If he moved, he'd probably punch the kid. Adrenaline surged and he had to fight it with all his being.

This was a nightmare.

"You're such a fucking child," Will said. He leaned in; he and Alex were an inch apart but it was so much different than when they'd been about to kiss. "Do I need to get you a sippie-cup? Do I need to put you in time-out?"

Something was off, though, because Alex wasn't cowing away; the more Will talked, the more he struggled to hold back laughter. The ensuing cocky sneer looked so out of place on him. "Yeah, you're right. I'm a child. ...and you really, really wanna fuck me. Don't you?"

Shut up. Shut the fuck up. He tried to say the words, but it would've been pointless even if he got them out. He wasn't in control here anymore. Denial flared up and he wanted to say: You're not a child, Alex, you're jailbait, but that was a technicality in a battle no one wanted to fight.

Will picked the little shit up and carried him off to his room. He tossed Alex down on the bed with a growl. The raccoon spun himself around, eyes wide, and for the first time, Will saw fear.

"Stay in your room," he barked, with all the authority he could muster. "If I see you outside, I'm just gonna pick you up and throw you right back in. Got it?" He paused. "Don't. Fuck. With. Me. I'm done playing games with you." He really didn't have any power over the teen, but he must have come off as just threatening enough to finally make the boy cow.

Will turned and closed the boy's door behind him. He held the knob, ready to deny the boy exit if he tried, but Alex's room remained silent and still.

Freedom, at last.

God, he needed to jerk off. Several times.