Tires crunch on gravel as the red station wagon pulls out of the driveway of a suburban, neatly-manicured home. Conrad holds back the curtains from the window, watching as the couple drives off on their date, leaving him alone with their son Miles. He waves at the mother in the passenger seat as they pull away, then lets the curtain fall back into place and turns back to his young charge for the evening.
The Dobsons aren’t paying him a ton, but Conrad doesn’t mind that much; he actually enjoys babysitting. It keeps him from sitting around the house bored all evening, and he always finds the enthusiasm of little kids really endearing. Might as well make a few bucks at the same time. He also weirdly enjoys being in other people's homes; the Dobson's house is picture-perfect suburbia, all pastel carpets and white walls covered in smiling photos. It feels like being in a magazine.
“So, squirt,” he says to the tousled, eager-eyed young child. Miles is slim, dirty-blond and rosy-cheeked, his face round like an apple. “What do you want to do this evening? Should we play some games?” He’s noticed that there’s a state-of-the-art console plugged into the TV, and an extensive shelf of video games, most of which are child appropriate.
Miles is clearly a chaotic child; he’s barely been able to sit still since Conrad got there, running back and forth between the living room and dining room the entire time his parents were explaining the house rules to Conrad. Even now he bounces eagerly up and down as Conrad tries to talk to him.
“I wanna play Mommy and Daddy!” he exclaims, eyes bright.
“You want to play house?” Conrad asks, surprised. It’s not what he was expecting from a little boy Miles’s age, but who is he to play gender police? If that’s what the boy wants to do...
But to his surprise, Miles shakes his head. “No! I want to play Mommy and Daddy’s game!”
“Okay,” says Conrad. “How do you play?”
Miles dashes to his side and grabs his hand, tugging him towards the floral-print living room sofa. “Here!” he says. “Lie down here!”
“Okay,” Conrad agrees indulgently, lying back with his neck supported by the arm of the couch. “Like this?”
Miles nods and begins to clamber up onto the other end of the couch, crawling up between Conrad’s knees. Then, without warning, he buries his face in Conrad’s crotch and rubs it back and forth, nuzzling at the babysitter’s groin. As Conrad’s eyes go wide and he bites back a curse, Miles starts making exaggerated moaning noises.
“What’re y- Holy sh-” Conrad stutters as Miles begins to open and close his mouth along the cloth-covered shape of his burgeoning erection. Conrad is only fifteen; he absolutely cannot be held responsible for the reactions of his body when treated in this manner. He’s already half-hard and stiffening quickly.
“Now you say nice things about me!” Miles insists, pausing for a moment in his ministrations.
“Buh?” Conrad manages, unable to form full coherent words.
Miles takes one of Conrad’s hands in both of his own and places it on top of his own head. “Say nice things! Whenever Mommy does this, Daddy always tells her that she’s doing a good job and how much he likes it!”
“Oh, I- I seEE-” Conrad’s voice jumps an octave as Miles returns to his previous task, rubbing his face all over Conrad’s cock through the fabric of his pants, pausing every so often to lightly mouth up and down the length of it. What he lacks in skill he is certainly making up for in enthusiasm.
Conrad’s hand tightens involuntarily in the short, soft strands of Miles’s hair. “O-oh,” he says, clearing his throat. “That feels- that feels really good. You’re doing such a good job. Yeah, just like that...”
His hips buck upwards, out of his control, pushing his crotch up against the boy’s face. Too much of this and Conrad is going to come in his pants.
“Thanks!” says Miles, beaming. He sits up, and while Conrad continues to watch slack-jawed, shuffles forward until he’s straddling Conrad’s hips. He then proceeds to sit directly onto Conrad’s erection, grinding his little butt down against the straining spike beneath. He wiggles his hips to make himself comfortable, and then starts moving himself up and down in exaggerated motions.
“Oh yeah Honey,” he says, “you’re so big! I love your meat! Now tell me how nice and tight I am.”
Conrad chokes. He grabs Miles’s arm, stilling him so that he comes to rest sitting on Conrad’s lap. Conrad’s eager cock twitches against the boy’s cloth-covered behind.
“Where- where did you learn this?” he asks, hoarse.
“I watch Mommy and Daddy do it all the time!” Miles announces happily, completely lacking in any kind of shame or embarrassment. “After bedtime sometimes I get up real quiet and I sneak up to their door and I watch through the crack. They play this game all the time! They really like it a lot.”
“Oh,” says Conrad, still shell-shocked. “And are your parents... naked when they play this game?”
Miles’s eyes widen. “How did you know? Have you played this game before?”
Conrad licks his lips. A horrible, unforgivable thought is working its way slowly through his brain, and he can’t stop himself. He shouldn’t. He can’t. And yet...
“Do you want me to show you how to play it properly, just like your parents do?” he hears himself ask.
Miles claps his hands together. He looks thrilled. “Yeah! Show me! Show me!”
Conrad clears his throat. “Then, uh... let’s go up to where your parents play this game, huh? In their bedroom, I’m guessing?”
“Yeah, come on!” Miles doesn’t need to be told twice. He scrambles off of Conrad’s lap, bounding towards the stairs.
Grateful to have a moment to collect himself, Conrad slowly sits up and follows at a more sedate pace. His dick is a solid steel spike in his pants, tenting them forward like it’s sniffing after Miles’s scent, eager to go after him.
Conrad mounts the stairs behind Miles as the boy scrambles up each step, peering back periodically to make sure the babysitter is still following him. When he reaches the landing at the top of the stairs he darts into an open door on the right.
Conrad follows him in to find a neat, unassuming bedroom with a well-made bed. The walls are lilac, with a matching bedspread. As he’d hoped, there are tissues and a small, discreet tube of lube on the simple white nightstand. He clears his throat once again.
“Now,” he says, “let’s both get naked, like your parents do.”
Miles already has his shirt half off before Conrad is even finished with his sentence. He shucks his clothes without modesty, clearly unconcerned about being nude in front of a near stranger. He stands with his legs braced apart and his hands on his hips as Conrad himself finishes removing his clothes. He's still all beaming smiles.
“Now what?” Miles asks.
Conrad sits on the bed and reaches for the lube. “If you’re going to play the part of Mommy,” he says delicately, “we’re going to need to make your body, uh... more Mommy-like. It’s playing pretend, right? I can get you ready, but it’s going to take a second.”
“Okay,” says Miles, sounding only a little skeptical. He puts his hands on his chest, one over each tiny pec. “Do I need big boobies like Mommy?”
Conrad laughs, turning it quickly into a cough. “No, not- not that. Here, let’s sit on the bed and I’ll show you.”
He gets up onto the bed and lies down in the center, partially upright against the pillows. Miles scrambles up after him; he is short enough that he has a little trouble, but he eventually manages without assistance. Conrad arranges him mostly perpendicular to his own body, with the boy’s face over his crotch and his rear end tilted slightly towards Conrad.
He picks up the tube of lube and opens the cap, spreading some of the gel inside on his fingertips.
“Now,” he says, “why don’t we start the game again.” He takes his cock in one hand and gives it a pump. “You can put your mouth on this, and I’ll start getting you ready to fully play the part of Mommy, okay?”
“Okay!” says Miles amiably. And without any further instructions, he once again lowers his face to Conrad’s crotch and begins to nuzzle at his cock.
Conrad lets out a winded huff before focusing on the task at hand. With one hand he reaches for the little boy’s buttocks, grabbing one and pulling it to the side, revealing the tight little treasure nestled between. “This is gonna feel a little weird,” he warns, before beginning to massage the pucker of the boy’s hole with his slicked-up fingers.
Miles once again switches to mouthing Conrad’s cock, lipping it gently up and down the length of the shaft. He doesn’t really appear to know what to do with it, but that’s fine by Conrad; if the boy went fully down on him right now, he’d probably just come immediately.
He continues to massage the boy’s anus for a few minutes, gradually relaxing him and getting him used to the sensation of pressure at his entrance. Then, when it seems like the boy is focused on his assigned task, rubbing his nose against Conrad’s balls, he begins the penetration.
He slips one fingertip delicately into the boy’s hole, not pushing very hard or very deep, just lightly breaching him. “That okay?” he asks.
“It feels weird,” Miles admits.
“I told you it would,” Conrad replies. “Just bear with it a little.”
Slowly, steadily, he pushes the finger deeper and deeper into the orifice, sliding into the tight, velvet-soft cavern. His mouth waters at the feeling of it, although that might also be from the sensation of the soft skin of Miles’s cheeks sliding up and down the shaft of his cock.
When the finger is as deep as it can go, he draws it out just as slowly, nearly all the way, before pushing forward again. He fingers the boy, smooth and delicate, cautious, waiting for him to be fully relaxed, to unclench around the digit, before he dares to add a second one. He repeats the motions, slowly driving two fingers now into the boy again and again and again with painstaking care.
“You’re supposed to be saying nice things!” Miles reminds him.
“Oh, of course,” says Conrad, putting on a bright smile. “You’re doing a great job! You’re so cute, Miles. And your body is so soft and welcoming.” He slides the fingers home, as deep as they can go in the boy’s ass, and pulses them there a few times, just brief pressing motions at the apex of the penetration. He stretches them as wide apart as he can, then brings them together and pulses again. Then stretches, then pulses, looping the motions again and again. “I’m so happy I came here tonight to play this game with you.”
Conrad is so hard his head is spinning. He needs to move this along. “Hey,” he says, “before we switch to the next part of the game, let’s do this how your Mommy really does it. Open your mouth as wide as you can and see how much of my thingy here,”—he gestures to his cock with his free hand—”you can fit inside at once. Try to get the whole thing as wet as you can with your spit.”
Miles looks curious, but he obediently opens his mouth and descends onto Conrad’s dick. It’s all Conrad can do to keep from bucking his hips up immediately and choking him as the warm wet cavern envelops his member. He brings his free hand up to Conrad’s head and buries it in the strands of his hair, tugging lightly.
“Oh yeah,” he says encouragingly. “That’s right. Just like that. Take as much as you can. Fuck. That feels good.”
Miles’s mouth is pretty small, and he can’t fit more than half of Conrad’s cock inside, but he makes up for this with an enthusiastic tongue, slobbering all over Conrad’s dick like it’s the best thing he’s ever tasted. He even starts bobbing his head up and down, like he’s apparently seen his mother do, forcing Conrad’s cock into his mouth over and over.
“Suck on it,” Conrad instructs. “Like a popsicle.”
Miles sucks, his cheeks going hollow, and Conrad chokes, nearly coming right there.
Miles backs off, looking up at Conrad from behind the spike of his penis. “Okay, it’s all wet. Now what?”
“Now,” Conrad says, “back like you were before. Straddle my hips, knees on either side. Yeah, just like that.” He only needs to touch Miles lightly to help him into position; the boy is back kneeling over him in moments.
“Okay,” says Conrad, taking a deep breath. “When Mommy and Daddy play this game, the trick is wet to wet. My wet prick goes up your wet hole. And then when you go up and down, like you did earlier, you’re actually moving my thing around inside you. Does that make sense?”
“Oooooh,” Miles says, eyes wide.
“Here,” says Conrad. He holds his dick in one hand and guides Miles’s hips with the other. “Let me show you.”
With a little maneuvering, he lines them up until he can feel the very head of his cock resting against the tight ring of the boy’s anus. “Deep breath,” he instructs, “and here we go.” And he begins to lower Miles down onto the spear of his phallus.
Miles makes a high, surprised cry as he’s breached, starting to squirm as Conrad’s erection pushes further and further up inside him, cleaving him open. Conrad keeps pulling the boy down relentlessly, holding his hips in both hands, forcing him down inch by painstaking inch. The boy’s rectum clenches around him deliciously, so tight it seems unreal. Conrad can’t stop.
He keeps forcing the boy down onto his cock until Miles comes to rest, once more sitting on his lap, but this time much less innocently. His dick is fully buried inside the child, filling him up. “Fuck,” Conrad breathes. “You’re so tight. Jesus that feels good.”
Miles smiles at him, although it’s a little watery. “Really?” he asks.
“Oh yeah,” Conrad reassures him. “You’re so good at this game. You’re a natural, I swear. I’ve never seen anyone as good at this as you are.”
“It feels weird,” the boy admits.
“I know,” Conrad says. “But we’re not done yet. You still need to bounce up and down on me like before. I can help you, if you want.”
“I-I can do it!” Miles insists. His voice sounds shaky, but he’s as good as his word. Moments later he’s flexing his legs to lift himself up, then slamming back down with full force. Conrad gasps as his breath is knocked out of him. “Like this?” Miles asks.
Conrad clears his throat. “Y-yeah. Like that. You don’t have to do it quite that har-”
His voice is cut off as Miles proceeds to fuck himself with abandon on Conrad’s dick. With all his youthful exuberance he begins to bounce himself up and down, sliding Conrad’s cock in and out of him over and over with surprising enthusiasm. It’s all Conrad can do to hold on as the little boy rides him, slamming his ass down onto Conrad’s cock again and again.
It doesn’t take long; Conrad was already close, and the amazing heat and softness and tight pressure all around him is altogether too much for him. Within only a few minutes he comes helplessly, holding the boy’s hips still as he creams into him, filling the child deep inside with his cum. “Yes, yes, yes,” he gasps as he unloads.
When he finally regains his senses, Miles is watching him curiously. Conrad pants as his dick begins to soften, slipping out of the boy’s ass even as Miles still sits on his lap. “How was that?” the boy asks.
“So good!” Conrad enthuses hoarsely. “Really good. Really. Um. Wow. You did a great job.”
“Really?” Miles’s eyes are once again bright and full of stars. “Does that mean we can play again?”
Late in the evening, Conrad looks up from the couch where he’s reading on his phone when the front door opens. Miles’s parents slip inside, looking tired but happy. They smile when they see him. “How did it go?” the mother asks quietly.
“Well!” Conrad says, smiling in a way that he hopes projects calm confidence. “He’s asleep in bed. I also gave him a bath first, I hope that’s okay.” He’d had to. It hadn’t been easy cleaning away the remnants of four separate orgasms from the child’s rectum. At least the two that had gone into his mouth had been swallowed.
“Of course,” the boy’s mother says with a smile. “Thanks for doing that.”
Miles’s father holds out a hand to him with some cash. Conrad looks at it blankly for a moment before remembering that he’s getting paid for all this. He takes it.
“It was nice to finally get a date night out,” the man says with a grin. “I don’t suppose you’d be willing to come and sit for Miles again sometime?”
“Oh, sure!” Conrad blurts, before clearing his throat and trying to reign in his enthusiasm a little. “Thank you, Sir. He’s, uh, he’s a good kid. Happy to come take care of him whenever you want.”