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Junior had two large hands roaming around his body, teasing him, touching him, getting him riled up. No thanks to Keith, he had a short black, frilly dress on with embarrassingly no underwear. Where his shitty mentor found the thing concerned him, but he didn’t have time to worry about the specifics. Now, he had to worry about where Keith was going, how his hands set him down on his bed with his ass up and in full view. Hearing a bottle pop open and a splurt, Junior tensed up when Keith grabbed his behind.
“What the fuck are you doing?!” Junior shrieked at the cold substance spreading throughout his skin. He didn’t know why he was asking in the first place and why he pretended to be grossed out. He knew his perverted mentor wanted to touch him in all the wrong places and make him pay for his behavior during training. Why Junior agreed to everything was way, way beyond him, but the thrill of doing something so wrong and immoral with his mentor excited him even if he didn’t want to admit it. As Keith undressed him, tore off each piece of clothing to toss aside in favor of a dress, Junior couldn’t help but whimper in excitement. His red, flustered face gave away his eagerness. He learned to take Keith seriously the first time he was forced to crossdress after their rocky start together. He had a feeling that eventually, he would end up bending — literally — to Keith’s will.
Keith loved it. Pouring lube all over Junior’s cute, small ass, the skirt of the dress lifted up to give a full view, he brushed his fingers by the boy’s tight hole. Barely touched or played with, Keith had the privilege of going all the way with his rookie.
“F...Fuck…” Junior cursed. “...f-feels so fucking weird…”
“Hey, we didn’t even start yet, kid,” Keith circled around it, teasing him while wearing a smirk Junior couldn’t see. “Gotta be quiet, too, ‘less ya want Faith to catch us. Don’t make me get somethin’ so I can put that loud mouth of yours to use, yeah?” and after he said that, Keith pushed his finger inside, causing Junior to yelp.
Junior moaned into the mattress underneath him, drooling when Keith hadn’t gone that far yet. “Fuck you…” he muttered loud enough for his mentor to hear and felt his tiny cock twitch at the slightest touch to his ass. That DJ wasn’t even here tonight.
“Not yet. ‘S my turn first, ‘sides you’re a little too small to start thinking of fuckin’ me, pipsqueak,” Keith smirked. “Just stay still, baby boy. You’re too tight for me,” he kept pushing in, going further inside Junior.
“T….Tight….?”
“Mhm, yeah. You’ve never done this before, right? Don’t wanna break ya in half with my cock.” Keith sounded proud of himself, and Junior hated his smugness.
“Shit! Fuck off! I-I can handle it just fine, you shitty ass perv mentor… Get your finger out of me!”
“Oi, that’s a lotta string of words there. Fine. Don’t say I didn’t warn you,” Keith listened to Junior for once and slowly pulled his finger out of him, making sure the boy would notice just what he was losing. “Didja want to stop ‘cuz you were afraid of cumming early? Look at ya,” he teased two fingers on Junior’s hole, and immediately, he whimpered, wiggling on the bed. “How badly do you want my cock, Junior? Tell me. Bet my fingers would do just fine for ya.”
Junior didn’t want to reply. He panted, cock leaking for a dire need of attention, and he moaned on the sheets. Looking back at Keith, his mentor wore a smirk as he moved away yet again. Keith grabbed his belt, and Junior’s body tensed up.
“Just… fuck me…” he said under his breath, head hanging low.
Unzipping his pants, Keith had an idea pop into his head. He took his cock out and waited for Junior’s reply, grabbing the lube to slick up his length. “Hm? That’s it?”
“Fucking… fucking please! Please, Keith... I need it!” Junior looked at him again and saw Keith’s hard cock out in the open. His jaw dropped at the sight. There was no way someone could be that huge. “D-Dammit…” Junior hissed, slightly jealous of Keith’s size.
“Cat got your tongue? It’s alright, you still got plenty of years to grow up. C’mere, Junior-chan.”
“The fuck do you want me to do?”
“What d’ya think?” Keith suddenly hovered over Junior’s body, grabbing his thin arms. “I wanna see your face when I fuck you, ‘s all,” he pushed Junior toward him and turned him around. “You’ll sit on my lap like a good lil baby boy,” the words entered right by Junior’s ears, and it sent a shiver down his spine. “You like that, don’t ya?”
“C’mon, Keith…”
“Right on my lap, baby,” Keith sat down and took Junior with him. “So easy to carry, so easy to fuck,” he taunted, groping Junior’s ass. “Spread them reaaaal nice for me.”
“S-Shit… I don’t think I-I can- N-No, I got this!...” Junior took a deep breath and hesitantly wrapped his arms around Keith as he went down, trembling when his cock brushed by his hole. He remembered the size of it and wondered how he was going to fit everything inside. “Keith…. Keith…. Fuuuuuck…!”
Groaning, Keith kept squeezing Junior’s ass as the boy eased his way down. “Right there. Yer doin’ good,” he complimented. “So fuckin’ tight, too,” he murmured under his breath, a prominent smirk on his face. “Ya gotta relax, kid.”
Everything burned the right way, and Junior was too stubborn to stop. He could feel Keith’s cock split him in half, his blue and gray eyes brimming with tears as every inch filled him up. Unable to control himself, Junior sniffled, his grip on Keith tighter than before. “I-It’s...so fucking big…” he whimpered into the other’s chest, quiet. “I...I’m so full…”
“Fuck, sayin’ things like that…” Keith pulled Junior away and made him look up. The boy blushed red. “And you’re crying, too. I thought you could handle it, kid.”
“I...I can!”
“Oh, yeah? Think you can ride me or is it too much for ya, huh?”
Junior gulped. “Yeah… I-I can do it! Watch me, shitty mentor…!” his voice wavered at those final words. Taking another deep breath, he prepared himself both mentally and physically. He could take Keith’s cock. It was fine. The problem was not turning into a babbling mess and letting him have the last laugh.
Keith scoffed at his hesitation, but he wasn’t going to stop Junior or scold him. He sat back and watched his rookie move his body, rolling his hips. Clumsy, whining each time the tip of Keith’s cock pushed itself right back in, Junior’s entire being trembled. It was music to his ears hearing Junior moan, watching his dripping small cock twitch with every movement. Mumbling his name, Junior picked up a rhythm, bouncing on Keith. The dress fluttered along the way. It fit Junior’s small frame perfectly, a purchase not gone to waste on Keith’s part.
“B...Bastard…” Junior couldn’t speak without whimpering, but as Keith’s cock went deeper in with each bounce, he realized something dire. “You just didn’t want to do the work, right? Fuck you!” he cursed, though that didn’t stop him one bit as he curled his fists to go faster.
“Little too late to complain about that, Junior,” Keith sneered. “You can come closer, and I’ll make it up to you. Promise,” his arms snaked around Junior’s waist and lifted him. “C’mere, baby boy.”
“Keith—!”
Brought forward by Keith’s pull, Junior yelped and found himself against his chest once more. He reeked of booze and cigarettes as always, a faint smell prominent enough to make Junior dizzy. The smell got worse as Keith cupped his face, kissing him without warning. The alcoholic taste made Junior shiver, more so as his mentor groped his body again, but he didn’t think twice about Keith’s kiss. It felt good, tongue and all, and Junior clung to his body not wanting to let go.
“M...more…” Junior panted when Keith broke the kiss — his first-ever kiss, but he wouldn’t dare admit it. “K-Keith, you shitty mentor… I want more—” he shivered feeling Keith’s cock ready to enter him again.
“Yeah? Can you beg a little more for me, baby?”
“Fine...fine,” everything felt so degrading in the black dress; any masculinity Junior had left was stripped away with each word he spoke. Gathering the courage to look Keith in the eyes, he begged again. “Please, Keith, I need you to fuck me again and again, your cock feels so fucking good in me and it’s all I want, please,” he needed to feel the sensation again of getting filled up, stretched out by Keith’s length. “I can’t believe I’m fucking doing this, you piece of—Keith!”
Back against the bed, Keith pinned down the young boy and smirked. He lifted the dress and Junior’s legs, slamming into him. Fucking him was too easy and too pleasurable. Keith could get drunk on the boy’s body.
“Shit, shit, fuck, it’s so big, Keith...!” Junior sobbed, and there was nothing he could do as Keith overpowered him. There was no complaining on either end, just a bed creaking with each powerful thrust and the mix of whimpers and groans.
“And you’re still tight,” Keith groaned. “So tight you’re gonna make me cum in ya… want me to do that, baby boy?” he paused to hear Junior’s reply. Instead, he got a hurried nod with a shameful expression on his face.
“Fuck yes, please!”
“Aww, you’re so excited, Junior-chan. Didja like my cock that much, huh? Want me to go deeper? You want me to fill every single part of ya with my dick?” each question came with its own thrust, fucking Junior within an inch of his life. “I’m gettin’ close, Junior. Wanna cum together?” his hand wrapped around Junior’s tiny cock, immediately getting a reaction.
“D-Don’t do that…!” Junior yelped. “I-It’s sensitive, I’m sensitive, Keith!”
“Oh, I know,” Keith kept going, grinding his hips as he jerked Junior off. “Cum for me, baby.”
“Keeeith! I can’t… I can’t fucking hold it in—Shit, shit!”
It didn’t take Junior too long to give in. His body tightened at the height of his orgasm, holding onto Keith as he came. Keith let go of his dripping cock and focused on fucking him hard. Hearing Junior’s whimpers and sniffles brought him to the edge, slamming into him one final time before emptying every drop of his seed.
Junior cried again, shuddering at his very first sensation of someone finishing inside him. It was addicting. He wanted more, and he’d go more if his body could allow it. “Fuck… I-It’s hot… it’s so hot…”
“Mhm, yeah,” Keith pulled out, staining the sheets underneath with cum — not the first time he spilled something. “You’re so good, Junior, I wanna do it again…” he lazily kissed Junior on his lips and cheeks.
“Fuck no. I’m sore, you asshole…” Junior tried to move his face away, annoyed at Keith’s alcoholic breath, but they shared another kiss to finish everything off. “Keith…” he blushed despite his stubbornness and expected Keith to say something.
He didn’t get a response. Keith fell silent and laid next to him after they kissed, snoozing.
“Oh, you shitty fucking mentor! You’re so fucking sleazy!”