Riley stood in the quiet kitchen, phone pressed to his ear. Diego’s voice came through from the hotel room two states away.
“You sure you’re okay handling everything with Angelo while I’m gone? I know those sessions take time.”
Riley kept his tone easy. “Yeah, it’s fine. Doctor’s orders. Physical therapy under supervision. Takes a while every now and then, private. Don’t worry about it from the road. I’ve got it.”
Diego exhaled. “You’re the best. I miss you already. Call me later?”
“Will do. Love you.”
Riley ended the call and walked down the hall. Angelo was sitting on the edge of the guest bed in a soft T-shirt and shorts. The boy looked up, big dark eyes still carrying that same soft, trusting innocence from the clinic.
“It’s time, Angelo. Doctor wants us keeping the schedule. Get ready.”
Angelo nodded. “Yes, sir.”
Riley held up the soft black blindfold. “Put this on first.”
Angelo covered his eyes without question. Once it was secure, Riley placed the new jockstrap in his hands.“Everything off, then put this on. It’ll make the exam easier.”
Angelo stood and undressed. Riley watched the soft T-shirt come up and over the boy’s head, revealing smooth brown skin and a narrow, toned torso. The shorts and underwear followed. For a few seconds the blindfolded boy stood completely naked before stepping into the jockstrap and pulling it up his smooth thighs. The pouch cupped him while the straps framed the heavy, perfect curve of his ass.
The sight of him made Riley’s cock thicken against his jeans.
Blindfolded little brown boy getting naked just because I told him to.
“On the bed. Same position as the doctor’s office. Knees spread, chest down.”
Angelo climbed onto the bed and settled exactly as instructed. Riley stood behind him for a long moment, freckled shoulders tight, strawberry-blonde hair falling slightly into his eyes.
How far am I going to take this today?
“Before we start with the tools,” Riley said, “I want you to open yourself up a little. Use one finger. Slow.”
Angelo reached back, found his own hole, and carefully pressed a single finger inside. A soft, shaky breath left him. Riley watched the way those plump smooth cheeks shifted, the way the tight hairless pink rim stretched around the boy’s slender finger.
He unzipped and freed his thick ten-inch shaft. It sprang up heavy and already leaking, the tall man’s strawberry blonde bush at the base contrasting sharply against the smooth brown skin in front of him. He wrapped a fist around it and stroked slowly while the boy fingered himself.
Diego’s tiny brown cousin on his knees, pushing his own little finger into that perfect hairless hole while I stroke my cock to the show.
“Keep going. Full circle.”
Angelo obeyed. Riley stroked faster, precum beading at the tip. He stripped the rest of the way until he stood completely naked behind the much smaller body on the bed.
After another minute he stepped closer, slicked two of his own longer, thicker fingers, and gently guided Angelo’s hand away.
“My turn. I need to check the depth properly.”
He pressed both thick fingers in slowly. Angelo’s moan was immediate and higher.
“Sir… your fingers are… bigger…”
Riley worked them deeper than the boy had been able to reach, curling them against the inner walls. Angelo’s massive bubble butt quivered. The boy’s small cock twitched inside the jock pouch, already starting to fill.
He kept fingering him for another long minute before reaching for the medical dilator.
“I’m switching to the device now. Just relax and take it.”
The dilator sank in slowly. Angelo moaned louder.
“Yes, sir… it feels big again…”
Riley fucked him with it in long, measured strokes, watching the plump smooth cheeks jiggle. After a few minutes he pulled it free and replaced it with a thicker, longer silicone dildo.
“New setting. Doctor said we need to retrain the muscle. Breathe.”
Angelo whimpered as the thicker toy stretched him open. “Sir… so deep… am I doing good?”
Asking if he’s doing good while I stretch his little boy hole.
Riley worked the dildo deeper. After a minute he pulled it almost all the way out.
“I want you to start pushing back on it yourself. Practice doing it alone. Long, deep strokes.”
Angelo began rocking his hips backward, fucking himself onto the thick dildo. Riley stepped back and kept stroking his own cock, eyes locked on the show.
Angelo pushed back harder. Soft, high moans spilled out of him as he worked himself on the toy.
Look at this fresh slut fucking himself on a thick dildo for me. Precum dripping down my cock just from watching him.
“Sir… why does it feel better when I push back harder?” Angelo asked between soft whimpers. “Is it supposed to make me leak like this down there?”
He asks the filthiest questions and he doesn’t even know.
“It’s normal. The pressure stimulates the nerves. Keep going.”
Angelo obeyed, fucking himself more deliberately on the dildo. Only when his moans turned continuous and desperate did Riley pull the toy free, line up the fat, leaking head of his own cock, and push forward.
The broad crown breached the tight ring. Angelo’s moan cracked into a long, broken sound.
“Sir… this setting feels different… like it’s pressing somewhere that makes it hard to stay still…”
Listen to him. Describing exactly how my cock is rubbing his prostate like he was made to whore put his boy pussy like this.
“Just another setting. You’re responding exactly the way the doctor wants. Keep being a good boy.”
Inch by thick, veined inch, Riley fed his ten-inch cock into the impossibly tight heat until his balls pressed against the soft underside of Angelo’s ass. The contrast was stark—his thicker, hairier white shaft disappearing into that smooth, hairless pink hole. He stayed buried for a long moment, then began to fuck him in slow, deep strokes.
Take every inch, brown boy. You think this is medicine. I know exactly what this tight brown hole was made for. Diego has never taken me this deep.
He freed Angelo’s small cock from the jock pouch so it hung free, already leaking.
“Keep pushing back on it. Practice doing it yourself. Long, deep strokes.”
Angelo began rocking his hips backward again, fucking himself onto Riley’s cock with growing confidence.
Riley’s phone buzzed on the dresser.
Diego’s name lit up the screen.
Riley answered, voice forced into something resembling normal.
“Hey, babe.”
“Hey. Just got out of the last meeting. How’s everything going over there?”
Angelo pushed back again, taking Riley deeper with a soft, needy moan that Riley barely covered with a cough. The boy’s small cock was already leaking steadily, a thin string of precum dangling as he trembled.
“Everything’s fine. Just handling that therapy session. Angelo’s doing the exercises.”
“Poor kid. You okay? You sound a little out of breath.”
Angelo rocked harder, chasing the pressure against his prostate. His body trembled more noticeably, small cock leaking freely, but he held back from tipping over.
Is he pushing back harder on purpose? There’s no way… not while I’m on the phone with Diego. He’s just following my instructions. That’s all it has to be.
The thought flickered and vanished almost as quickly as it came.
“Yeah. Just supervising. It’s a long process.”
Angelo whimpered, “Sir… it feels so deep… am I still being good?”
“He’s doing fine. Following instructions really well.”
“That’s good. I feel bad leaving you with all of it. You sure you don’t want me to try and come home early?”
Angelo drove himself back harder, longer strokes now. The boy was trembling harder, clearly close, but still holding on.
“He’s almost done with this part. Just a few more deep ones like the doctor ordered.”
“You’re really good to him. I love you for it.”
“I love you too. I should go. I need two hands for this.”
“Okay, babe. Call me when you’re free. Miss you.”
Riley ended the call and dropped the phone onto the mattress.
The second the line went dead, the urge hit him hard. He grabbed his phone again, switched to video, and angled it down to capture the exact view of Angelo’s much smaller body still pushing back onto his thick white cock—the way those plump smooth cheeks rippled, the way the tight hairless pink hole stretched and clung around his hairier shaft.
“Keep going. Harder. Show me.”
Angelo obeyed. Still trembling and leaking, the boy pushed back several more times, longer and deeper, chasing the pressure against his prostate even though he didn’t understand what he was chasing. Soft, desperate moans spilled out of him as he worked himself harder on Riley’s cock.
Making himself leak and tremble on my cock. Fuck I need this on my phone for later.
Angelo’s movements grew more frantic. He started slamming himself back harder, clearly trying to hit that same deep spot over and over. His whole body shook.
Then it hit.
A long, high moan tore out of the boy as his small cock pulsed and began shooting thick ropes across the sheets. His hole clamped down in powerful, rhythmic spasms around Riley’s throbbing shaft.
Mid-orgasm, Riley set the phone down. Both hands found Angelo’s narrow waist. He gripped hard and fucked the rest of the boy’s climax out of him—rough, deep, possessive thrusts that drove every remaining pulse from Angelo’s cock while that tight smooth hole milked him in return.
Fuckk. That’s daddy’s pussy. I own you, slut. Mine.
Angelo cried out, still cumming, body jolting with every hard thrust as Riley fucked the orgasm through him.
When the last of Angelo’s release finally stopped, Riley didn’t pull out. He stayed buried and spoke low, voice still rough but controlled.
“Don’t stop. Keep pushing back. The doctor said you need to keep the muscle working through the full response. Full strokes. Train it properly.”
Angelo whimpered but obeyed. Still oversensitive and trembling, the boy began rocking his hips again, fucking himself back onto Riley’s thick white cock.
At first the strokes were shaky. Each time Angelo pushed back, that tight pink hole dragged along every thick vein, squeezing and releasing in a wet, rhythmic grip. Riley stayed completely still and let the smaller body
Just came all over the sheets and he’s already milking my cock again because I told him to. This boy was made to serve a big white man.
Angelo’s movements gradually found a steadier rhythm. He started taking longer strokes, pulling almost all the way off before driving himself back down to the root. After a while his small cock began to harden again, twitching and leaking fresh precum as he chased the same deep pressure from earlier.
He found the sensitive spot.
Soft, broken sounds spilled out of him as he started grinding himself back harder, clearly trying to hit that place over and over. His whole body trembled. His small cock leaked steadily, then pulsed.
A second orgasm tore through him. Angelo moaned high and broken as his cock shot again, weaker this time but still thick, painting fresh ropes across the sheets. The second climax made his hole clamp down hard around Riley’s shaft in tight, rhythmic spasms.
That sudden, greedy tightening was what finally broke Riley.
His climax hit in a thick, crushing wave. His cock swelled even harder inside the boy and the first heavy pulse ripped through him so strongly his whole body shuddered. Thick, hot ropes of cum flooded deep into Angelo’s guts.
Riley groaned low through clenched teeth. He couldn’t stay still any longer. Both hands locked on the boy’s narrow waist and he started fucking the rest of his load in—deep, possessive thrusts that drove every remaining pulse deeper while that tight hairless hole continued to squeeze and flutter around him.
Take it, boy. Every drop. You earned daddy’s seed. This load is yours now. This tight little brown hole just milked it out of me and it’s staying right where it belongs.
The second wave hit harder than the first. Then a third. Riley’s balls drew up tight as he kept thrusting, breeding the boy through the last of it.
The final wave hit so hard that Riley’s hips jerked. He pulled back just an inch at the peak of it, and the last thick rope of cum painted across the smooth brown skin of Angelo’s lower back in a hot, messy stripe.
Still overstimulated and throbbing, Riley immediately shoved himself back in—one hard, deep thrust that buried him to the root again. The fat head of his cock dragged firmly across Angelo’s prostate as the last of his load pumped deep inside.
Angelo let out a sharp, high whimper that turned into a long, broken moan. “Sir—ahh—”
Riley held himself there, buried completely, letting the final pulses empty into the boy while that tight hole continued to flutter and squeeze around him.
Only when the last twitch faded did he slowly pull out. Thick white cum immediately began to leak from the stretched pink hole. He quickly pressed the medical dilator back inside to plug it, then carefully wiped the streak from Angelo’s back with a tissue before the boy could notice.
“The fluid from the machine again,” he said quietly, voice still rough. “You did very well, Angelo. You kept working through the full response just like the doctor needs. Keep the blindfold on and rest. I’ll clean everything up.”
Angelo panted beneath the mask, still trembling faintly. “Yes, sir… I try to be good boy… even when it felt too much… and when it was throbbing and filling me… thank you for helping me with the treatment…”
Riley stopped the recording on his phone. His heart was still racing. Diego’s voice still echoed in his ear.
The doctor had been very clear. These sessions needed to happen regularly.
