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Toby is ecstatic. He finally, finally gets to get out of this God-forsaken house a few times a week, other than the three hours of church service every Sunday. Normally he’s got to spend time with the family, he has too much home-school work left, he’s behind on chores, or he’s grounded.
Things are looking up now though!
He’s finally allowed to work as a delivery driver now that he’s gotten his license, and has been ahead with his homeschool stuff. He’s been trying extra hard to act like a good little girl and stay out of trouble too. He’s so excited even though everyone at work calls him Tabby and his name tag has his deadname on it.
But it’s not like he could come out. Someone would tell his mom. And then who knows what would happen. Would they send him away for “help” or just kick him out? He can’t risk it, not yet.
But it’s worth it. He gets to wear pants and when he tucks his long braid up under his uniform hat, he almost looks like a real boy. So he just takes off his name tag once he gets in the truck and once in a while someone calls him “sir” or “son” when he brings them their delivery. He beams every time. It's better than any tip.
He starts picking up more evening shifts, telling his parents he just really wants to give back to the church and be more responsible for himself. Really, he just wants the thrill of being seen as a boy. With his first check, he gets a couple really tight sports bras, and nobody really notices since he usually dresses in modest layers anyway. But it makes him feel better. At work, more people gender him correctly, so it’s worth the aching ribs and slightly raw skin.
One Saturday night, he gets a delivery to a house he recognizes. A girl around his age that goes to church with him on Sundays, Kara. She once confessed to him that she just went because there was free food after and she grew up so poor that she never turns down a free meal now. So he’s prepared for her or maybe her nice foster mom to answer the door.
Instead, he’s greeted by a man in just a pair of sweatpants, obviously half tented at the front. The guy’s several years older than him, at least 21 if the case of beer by the coffee table is any indication, and he vaguely recognizes him as Kara’s older brother, Kevin. In the background, porn is playing on a big screen tv. He blushes as the shameful sounds hit his ears.
“Ya wanna make an easy 50 bucks?” He asks with a lazy grin.
Toby freezes. He knows he should give the guy his food and go, but Kevin is looking at him like he’s something special and that kind of attention is just too tempting. He nods sweetly and lets himself be led inside.
“So um, what did you want me to do mister?” He looks down at his hands, avoiding looking at the busty women loudly fucking on tv.
“Hey kid, don’t be shy. Ya see this?” Kevin sits on the middle seat of the couch with his legs spread, bulge on clear display. “I’ll make it real simple for ya. You suck my dick, you get $50, no questions asked.”
Toby blushes right to his ears, eyes wide. He’s never even kissed anyone before. He isn’t really sure he wants to do… that. But he could use the money if he wants to save up enough to move out and transition as soon as possible. He nods hesitantly.
“I-I’ve never… not even kissing. B-but I could try.”
The older man grins and leans forward on the couch, beckoning him closer. “C’mere then sweetheart.” He tosses a throw pillow down on the floor in front of him. “On your knees right here for me. I made it nice an’ comfy for ya since it’s yer first time an’ all.”
Toby sits the pizza he’s still holding on the coffee table and kneels down on the pillow, trembling. He doesn’t look up, just focuses on the pattern of the pillow under his knees and tries to control his breathing.
He’s startled into reality by his hat being slipped off his head. His braid falls over his shoulder. “Easy baby, I’m not gonna hurt ya.”
He leans back then and slides his sweatpants down his thighs enough that his stiff cock springs free. Toby wants to look away, but he’s never seen a dick before. Not a real one. And certainly not one being lazily stroked a few inches from his face.
“It’s easy baby, just open yer mouth an’-”
“W-wait! This is…I’ve never even seen a p-penis in real life so just go slow.” Toby blurts out, leaning away a bit.
Kevin leans closer and gently strokes the top of his head and down his cheek until he’s cupping the younger boy’s jaw. “Yer serious, ain’t ya? Okay sweetheart, I’ll go easy yeah? Now open up.”
Tobias tenses, but he does as he’s told. Slowly, he leans in and wraps his lips around the head. It tastes a little salty and tangy but only faintly, and the skin is soft under his tongue. His tongue flicks over the tip cautiously, but he’s still so tense.
The kid’s inexperience and anxiety is adorable, and he almost wants to just shove into that tight throat and watch his pretty face contort in panic as his airway is cut off. But Kevin doesn’t want the pretty little thing accidentally biting him, and ideally he wants the boy to be willing to do this again. So he plays nice, for now.
“Relax yer jaw baby, I won’t do nothin more than this fer now.” His thumb soothes along the tight muscles of Toby’s delicate jaw.
Toby takes a shaky breath through his nose and lets the older man’s touch soothe his nerves. He tentatively laps at the little slit, not sure if he likes the slimy texture of the fluid that seems to leak out faster the more he licks. He’s thinking of pulling back when Kevin lets out a groan and his thighs tense under Toby’s hands.
“Yer a real natural at suckin’ dick, yanno that kid? And here I thought I’d hafta really tell ya what ta do.” He’s not sure why, but the praise sends a heady rush of heat through his body that pools in his belly and makes his thighs press together.
Toby manages to relax his jaw and slide down a little further, the other’s cockhead bumping up against the roof of his mouth. The slide of soft skin there is unexpectedly pleasant and a sound bubbles up from his throat.
Kevin’s hand grabs the base of the kid’s braid and tugs him back until his dick is just brushing against slick lips, grinning when Toby whines. He runs a hand down the long braid and snaps the hair tie, running his fingers a little roughly through the long dark hair.
Tobias whimpers, the tug in his hair making his scalp tingle and his breath hitch. He feels big hands in his hair, guiding him, holding him still while Kevin grinds his slick cock against his cheek. This shouldn’t feel good, and Toby is a little scared, but something about doing something so bad, so against God and his parents and his church that hates the way he was made feels so good.
He turns his head, mouth open and tongue out obscenely, trying to chase that feeling. When he looks up at the older man, Kevin groans and lets one hand cup his jaw, roughly shoving his thumb across the kid’s tongue until it makes him choke. Toby whimpers but doesn’t try to back off, looking at him through damp lashes.
“Awe fuck, baby, were ya havin that much fun? Ya want my fuckn cock again? Open up.”
Kevin squeezes his jaw and slides forward on the couch, shoving his cock into the boy’s mouth, much less gentle this time. Toby’s eyes fly open in panic and he makes a noise, trying to move away but being held by a big strong hand as the older man begins thrusting into his mouth, gagging him with every dragging thrust.
“Easy sweetheart, breathe through yer nose and let yerself relax again. That’s it baby, just let me use yer mouth fer a minute.”
He’s scared and it feels like he’s going to puke, but Toby tries to do as he’s told. Saliva pools and leaks out of the corners of his mouth, dripping thickly down his chin. Kevin’s hands gentle, stroking through his hair and it feels good to be touched like that. When he looks up through his tears, Kevin looks almost tender in spite of the hungry look still in his eyes.
“There ya go. Yeah, that’s my good boy, relaxin’ fer my cock. Just a little more, baby an’ I’ll let ya get back ta work alright?”
Toby tries to nod and gags hard enough that bitter acid hits the back of his throat. But the way the older man groans over him, eyes sliding shut makes it not so bad. Slightly frothy drool leaks out around the cock thrusting in his mouth and vaguely thinks he’ll have to wash this shirt before he works again as it soaks down into the collar.
The hand in his hair tightens and he moans again, the pain blooming across his scalp fading to a rush of hot tingles. Kevin must notice because his other hand fists into his hair and tugs too, hips stuttering as he thrusts in particularly deep.
“Fuck kid, ya like that? I thought ya were all innocent an’ pure, but yer just a little freak, huh?” Each word punctuated with a little tug to his scalp, making him squirm.
He holds himself there, stuffed down Toby’s throat so far he can’t breathe, but the feeling only lasts a few seconds and makes him feel sort of floaty and warm. The crude degrading words make his face heat up, but he does. He likes it. He feels all tingly and hot and dirty and good, good, good.
Toby can’t really think anymore as he’s pulled up roughly by his hair so that Kevin can use his throat better. He’s moaning or maybe crying? He’s not really sure, but the sickly sweet tone of the man using him as a fuck toy makes him ache between his legs, boyshort underwear suddenly uncomfortably wet.
“Fuck, fuck sweetheart, that’s it baby. Gonna cum all over that pretty little face a yers. Gonna ruin ya for anyone else.”
Toby practically sobs when Kevin pulls out and squeezes his jaw, forcing his mouth open.
“Open up fer me, stick out that dirty little tongue a yers, c’mon.”
Toby opens wide, eyes shut as the man pushes up off the couch to stand right over him. Kevin strokes himself once, twice, then he’s cumming, spurting thick rivulets all over that innocent face and tongue. He wants this kid to be completely wrecked.
He milks himself, rubbing the head over the kid’s lips and smearing them with the last of his release when he shuts his mouth and swallows harshly.
“Holy fuck kid. Ya sure that was yer first time?”
He collapses back on the couch, absently stroking Toby’s cheek, rubbing his cum into the flushed skin. Kevin wipes his cum covered hand through the kid’s dark hair.
Toby trembles, thighs pressed tightly together, breathing hard. He doesn’t even know what to feel and he’s caught between tears and pride and something else he doesn’t quite recognize yet.
“Y-yeah. Did I do okay?”
He suddenly needs confirmation that he’s not horrible and worthless and all used up now that he let someone deflower him and liked it. That he did good. His eyes flood and spill over with tears, leaving tracks in the cum on his cheeks.
Kevin’s softening cock twitches at the depraved sight in front of him, this boy crying, covered in his cum. He reaches down and cups Toby’s messy cheek, letting the kid nuzzle into his touch.
“Yer a natural, kid. Real good with yer cute little mouth.”
Kevin tucks himself away and tugs the boy up into his lap. He’s not usually into being cuddly but this was the kid’s first sexual experience and he wants it to be a good one so maybe there will be a repeat. He strokes Toby’s back and murmurs to him until he’s all cried out and blushing cutely.
“Sorry for crying and making you have to pet me like I’m some needy kid or something… I uh, should probably head back though… I’m late for the end of my shift.”
With that, Toby scrambles off Kevin’s lap and straightens himself up, wiping at his face with some random napkins and practically flees the house before he can embarrass himself any more.