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Tommy is frustrated. Frustrated at his dumb body, mad at his dick to be specific.
His hands never satisfy. During his 4 years of being a teen, he hadn’t come once. He’d lay in bed for hours, fisting his poor spent cock, the tip purple and shaft red. Hours wishing for a simple release, every fiber of his being straining to stay on the edge to hopefully fold over, but never coming.
Tears filled his eyes, his hips gently thrusting into his dry palm, gripping the sheets as he prayed to every god there was that he would cum! But it never came. “Fuck. FUCK.” Tommy punched his pillow. “Stupid. Fucking. Body.” He pulled his boxers up and sat there, cock painfully pushing against his boxers, hands in his hair.
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Tommy sat at his desk, chewing his fingers gently. Was he really about to ask for advice on how to mastubate from Wilbur? His hand shook softly as he hovered over the call button. Second thoughts blasting through his mind. His finger clicked on the video call, there was no going back now.
The older man's face popped up, he gently swiped the hair out his face. “Ayup, hello Tommy!” Wilburs cheery voice rang through the teens ears, echoing off every corner of his mind. “Hey wil.” Tommy spoke meekly, shyly pulling his leg onto his chair, wiping the hair out of his face.
“And what have you called me for? You said it was important?.” Wilbur spoke softly, his tone of worry showing through. Tommy’s face flushed. “Well..” the boy trailed off, instinctively running a finger across his nose, “it’s an embarrassing question.” Tommy breathed softly, scared even a breath would scare the older. “Well Tommy, nothing you say could be too embar-“
“How do you cum Wilbur?”
The older froze, mouth hung slightly agape, “Pardon?” Wilbur broke the silence. “H-how do you cum?” Tommy asked, now much shyer. Wilbur sat up and adjusted his seat. “Uhm..that is nothing to be asking meTommy.” Tommy sighed, “I know wilbur..I’m just desperate. I haven’t cum. Not once. I..I just need help. Please.” Tommy felt tears prick his eyes, his fist clenched tightly, “it..is so..fucking annoying Wilby.” Wilbur felt his stomach drop as his pants tightened.
Why was the boy begging so hot?
Wilbur gulped deeply. “Have you tried anything special?” Tommy shook his head softly. “Well there is this one way I know of, I heard it’s a good try?” Wilbur suggested softly, his voice lowering to not scare the boy.
Tommy thought for a second, choosing to do whatever Wilbur suggests. “Mm, I’ll do it.” Tommy smiled softly, clicking on his camera, “show me what it is, please?” Tommy puppy dog eyes the camera, gently pushing out his lip. The brunette smiles widely. “I sure can, baby.” The blonde blushes at the pet name, inching forward in his seat.
“Now, it’s a bit weird at first, but most likely worth it.” Wilbur took his shirt off, Tommy’s breath hitched, eyes raking over the oldest body. His lightly tanned skin reflected the purple of his lights, skin as soft as silk meshed against formed muscles. “Do the same Toms.” Tommy clumsily ripped his shirt off, feeling cold in the darkness of his room.
“Now, just do what I do okay?” Wilbur gently slickens his finger with saliva. “Okay Wilby.” Tommy follows suit, feeling the watchful eyes of Wilbur follow his every move.
Wilbur brought us another hand down to his pants, pulling them down to release his hardened cock. Tommy’s body buzzed, his own hand following suit. Wilburs cock was bigger, and definitely had more girth than Tommy’s. Wilburs hand stroked himself slowly, “come on toms, you’re being such a good boy.” Wilbur spoke softly.
Tommy’s hand gripped himself, moaning as he stroked himself at Wilbur’s pace. Wilbur brought his slickened fingers to his..bellybutton?
Tommy tilted his head in confusion and opened his mouth to speak before being cut off by a loud moan from the elder. “Oh! Fuck.” Wilbur hissed, “sorry if I scared you toms, please continue.” Tommy sat shocked as Wilbur curved his fingers into his naval, watching with awe as the man quivered at his hand.
Tommy hesitantly pushed his fingers, the weird sensation made Tommy almost quit, but as he curled his fingers he clamped his teeth on his lip. The moan he let go was music to Wilbur. “Oh? How does that feel, baby?” Tommy hummed softly as he breathed heavily, recovering from the shock of pleasure he felt. “It felt so good.” Tommy slurred, high on the pleasure he was receiving.
Wilbur laughed softly and continued his movements, moaning at the sight of the teen before him, a shaking mess in his chair, sweat sticking his golden locks to his forehead.
Tommy’s hand shot up and down his erection, really wishing he had used some lube. The friction was eased by the amounts of precum leaking from the teens cock. The pre made a slippery mess. “You look so beautiful baby, you can cum whenever you like, okay? You certainly deserve it for being such an amazing pup.” Tommy’s back arched at the olders words.
He had never felt this close before, his body electrical at every twist of his fingers in his naval, rubbing against the special part of himself. The heat of his breaths clouded his mind, moans of Wilbur faded, a snap in his stomach was made.
Tommy screamed, thankful his parents were out, releasing ropes upon ropes of his pent up cum onto his stomach. Clenching his toes and arching his back hard, stroking himself furiously through his first orgasm. “Oh my fuck! Wilby! Wil! I..I feel so good, fuck! Thank you wil! Thank you Wilby!” Tommy rambled, fingers slicked, tears streaming down his face from pure pleasure.
Wilburs eyes bulged, the sight before him holy. His fist went faster, reaching his release not long after Tommy. “Fuck toms, you’re such a good boy! Holy fuck you are so hot baby. You make me feel so amazing, baby.” Wilburs eyes screwed shut as he burned the image of Tommy into his mind.
Tommy slowed his hand and blushed deeply, “I did it!” He chuckled softly, his voice scratchy from screaming. Wilbur smiled softly and sat up. “You made quite the mess.” Tommy looked down at himself, his stomach and hand covered with cum, fingers dripping cum. “Oh. So this is what this stuff feels like. Heh. Sticky.” The blonde smiled as he felt and pushed around the cum.
Wilbur grimaced “go clean yourself up weirdo.” Wilbur giggled as he grabbed tissues to clean himself. “You were great Toms.” The older one reassured as Tommy stood. “Thank you again Wilby, I hope this isn’t the last time we do this.”
Tommy walked away, leaving his headphones on the desk.
“I hope so too.” Wilbur spoke to no one.