Seeing It Through – Part 03

By Cutieboy90

Six months…

Tyler tapped his chin ponderously.

“Is this it, then?” He asked after several tense minutes of silence. “In three months, all you’ve done is one half of the promenade deck?”

Stefan bit his lip.

“The contest is still another six months away, you have the time. I just wonder if you have the focus. Or if it’s being split and spent elsewhere…”

Stefan cleared his throat nervously. “Well… Yeah sort of. It’s just that. Uhmmm…”


“The uh, window frames… They…” Stefan broke a sweat. “Take a lot of time. And uh… I dunno, kinda spending a lot of time…” He trailed off, turning away from the desk to hide his blush.

Tyler happened to glance down and noticed the unmistakable outline of a buttplug at the seat of Stefan’s jeans. One of the big ones. He tried to conceal his smirk.

“You… Seem more relaxed today,” Tyler lightened his tone as he eyed his friend. “Perhaps it’s intentional?”

“Yes!” Stefan replied quickly. “Yes! Uh, very intentional. I planned for this step to take time, and I’ll still be ready for the contest. Yeah.”

Tyler smiled.

“Of course it’s intentional. It’s just… You seemed so eager to finish this project quickly, to be unlocked sooner. And now…” He stepped closer.

“A-and now… I’ve gotten more… Used to the horniness?”

“Right, that must be it…” Tyler nodded. “Well I should let you get back to your… Intent.”

Stefan sighed in relief as Tyler left.

“Oh fucking GOD that was close…!” Stefan leaned against his desk. “If Tyler ever found out, he’d never let me live it down.”

Stefan reached back and pressed on the plug stuffing his backside, waves of pleasure jolting through him.


The truth was, he’d gotten addicted to playing with his hole. He spent all his free time pleasuring himself, and now he’d fallen behind on what was the only real way he could. He had to finish the model in order to get the cage off.

With a moan, he sat down at his desk to resume his work on the promenade deck windows.

Fighting the temptations of pleasure, Stefan got out the tweezers, the glue, and methodically worked the window frames one at a time. He clenched on the plug, bouncing on it lightly as he worked. Stefan Jr. drooled in his cage, re-slickening the toy’s thick neck.

Yeah, Stefan had spent way too much time playing with the large dildos and plugs Tyler had given him a few months before. Now wearing a plug on a daily basis, Stefan felt more content. Still horny as fuck, but somehow less on edge.

Finishing the promenade deck windows, Stefan put his tools down and sat back for a moment. The plug pushed further into him as he took a deep breath.

“Well, I’d better make up for lost time now…” Stefan set the promenade deck aside and tackled the window frames for the various boat deck bulkheads. These didn’t take long, as there weren’t as many to do. The last thing he did was prepare the rigging for the funnel stays, which needed to be threaded through tiny holes in the boat deck.

“Tomorrow I’ll glue the boat deck to the promenade deck,” Stefan resolved as he turned out the light. “But tonight, I think I’ve earned a good fuck. Maybe I can make myself cum…”

Stefan had managed to work up to the second-largest dildo, a fat purple monster of a phallus. So far he had only been able to take half of its great length, but tonight he was determined to hilt it.

“It’ll feel soooo good…” Stefan shuddered in anticipation. He set the dildo down on its base, and sensually lubed it up. Treating it like it was his own cock, Stefan rubbed it down with lots of lube until it was thoroughly slicked. A handful of extra lube went back to his own hole which was still lubed from the plug he’d been wearing. But Stefan knew he’d still need it.

With the big dildo standing proud and ready, Stefan knelt over it and gently lowered himself down with a gentle bouncing motion. Its moderate tip popped in with little resistance, lighting up Stefan’s prostate like a Christmas tree. The toy tapered significantly after the tip, growing thicker toward its base. Its widest point was just after the halfway point.

“Tonight’s the night,” Stefan murmured as he worked himself down, feeling the top third of the toy stuffing him full. “Tonight… When I get this in… I’m gonna ride it till I cum… I know it will…”

Stefan Jr. was now leaking like a broken faucet from all the internal attention. Several long thin trails of clear slimy pre ran down from the end of the cage, flowing over his nutsack, down his thighs, and soaking into the bedspread.

“Yeah…” Stefan reached down to feel up his thighs. All the squatting and thrusting had built his leg muscles up in a way the gym never quite had. His quads were well-pronounced now, as were his calf muscles. His ass had also filled out, in more than just one way… His glutes were nicely round before, but now they were firmer and bigger. He gave them a squeeze, still bouncing down the toy.

“Ohhhh… Ughhh!” Stefan was approaching the halfway point. He slowed his pace slightly and took deeper breaths. “Easy… Breathe… Relax…” Stefan arched his back and looked up at the ceiling. “Just breathe through it… It’s just a stretch… Ahhhh…!”

It wasn’t a painful burn, not exactly. But it was definitely not a pleasurable stretch, either. Stefan stopped bouncing to let himself acclimate. He grabbed his balls in a gentle caress, rolling his tender orbs in his palm. His finger pressed gently at his taint, just behind the metal ring that secured the cage. A moan burst from Stefan’s throat.

“Ohhh… God…”

It was enough to distract him from the stretch. Enough to help ease another quarter inch into Stefan’s tight hole.

“Ahhhhhhh… Fuckk yeahhhh…” Stefan squeezed his eyes shut and he threw his head back. He hesitantly resumed his bouncing motion, even as his thighs were beginning to burn.


In his haze of determined pleasure, Stefan didn’t hear the car engine, the car door slamming, nor the front door. He didn’t hear the footsteps in the hall.

“Stefan? Hey buddy, are you alright?” Tyler’s voice rang down the hall.

Stefan’s eyes shot wide open. Fuck! What was Tyler doing here!?

“You ok in there?” Tyler rapped on the door. Stefan, still naked and holding the dildo halfway up his ass, scrambled to the edge of the bed.

“Uhhh… Yeah, I’m… I’m fine, just uhhhh!” Stefan stammered, trying to hide the mix of pain, pleasure, and now anxiety. “What-uhhh, what are you-”

“You sound like you’re having a heart attack, man. I’m coming in.” Tyler opened the door and froze as he took in the sight of his hot friend perched on the bed, face flushed, cage leaking, the unmistakable purple mass sticking out from under him…

Tyler smirked as Stefan struggled to explain. He shook his head.

“Sorry bud… I thought I had left my magnifiers here so I texted. Came back, and heard all these… Heheh… Pained noises.”

Stefan nodded, his body acting on its own and continuing to bounce on the toy.

Tyler gently approached, helping Stefan back into his kneeling position on the bed.

“Come on man, don’t stop on my account,” Tyler stroked Stefan’s back. He rubbed his hands together and applied some lube. “It might help to get a thicker formula for this, but this will suffice for now. Just breathe…”

Stefan couldn’t help himself. He reached over and held Tyler’s shoulder for support.

“Easy does it, arch your back… Breathe… That’s it…” Tyler’s voice was soft, encouraging. Stefan nodded, finding himself feeling soothed. With Tyler guiding and supporting him, Stefan could focus on his task.

Tyler’s hand caressed Stefan’s chest, abs, and thigh.

“Doing good, buddy. Just breathe through it,” Tyler whispered as Stefan’s legs began to tremble.

“Ohhhhhhhh…!” Stefan suddenly slipped down, impaling himself further on the toy. His prostate had been mashed, his guts rudely rearranged, but it felt so good!

“Here, this will help.” Tyler produced a thick leather bar gag, which he deftly shoved between Stefan’s teeth and buckled firmly in place.

Stefan chewed distractedly on the gag, still recovering from the shock of the latest incremental progress of the dildo. He could feel he was past the halfway point now…

Tyler applied some more lube to the toy. His hands were gentle as they felt up Stefan’s burning thighs, squeezing the individual muscles as they worked.

“That’s it, looking good…”

Stefan slipped further, the fresh lube removing what friction was left. His battered hole had little resistance. He bottomed out, the base of the dildo seating itself with a sudden pop.


“Easy there, breathe… Breathe…”

“UGHHHHH!!!” Stefan squeezed his eyes shut, a couple tears rolling down his cheeks. The pleasure surged through him, overwhelming his senses.

Tyler stroked Stefan’s body, his warm voice a soothing balm.

“You did it, champ. Relax, breathe in… Out… In… Relax. Enjoy it…”

Stefan bit down hard on the gag, breathing through his teeth as his lower body struggled with the large intruder.

“Here…” Tyler helped move Stefan’s legs out from their kneeling position and into a cross-legged seated position. Stefan leaned back against his headboard, his eyes still squeezed shut.

Tyler perched astride him on the bed, lightly stroking his chest.

“Huugh…” Stefan panted as he finally opened his eyes and released the bit with his teeth. “Uhh huhph phaa huh… Wuuh uh humph aa hoo phugh?”

“No buddy, we’re going to keep that gag in place for now.” Tyler swatted Stefan’s hands away from the gag. Too exhausted to resist, Stefan just nodded and rested his head back. He reached down and fondled his swollen nuts, now soaked in the flood of pre flowing from the end of his cage. He hadn’t cum.

“Uhhhhuhhhhh…” Stefan pouted.

“Aww, did you think you’d be able to get off like that?” Tyler tsked. “That sucks, man. Though you won’t need a prostate milking again for a while. Remember there’s only one way you’re getting off.”

Tyler pulled Stefan off the bed, quickly encircling Stefan’s waist with a leather strap that ran between his legs. It held the dildo in place.

“NFFFFF!!” Stefan begged through the gag. The dildo was really beginning to hurt now that it was all the way in, stretching him beyond his limits.

“You’ll get used to it.” Tyler said brightly as he locked the buckles for the harness. “Come on.” He led Stefan back into the workshop and sat him down at his desk. Stefan Jr. spat out a little burst of fluid as Stefan was pushed into the chair, ramming the dildo against his prostate.

“Now that you know you won’t be cumming, you might as well get back to it…” Tyler flicked the lights on.

Stefan sighed and nodded reluctantly. He pulled the Promenade and Boat Deck assemblies over and proceeded to join them. It was hard to focus with the monstrous toy stabbing him from the inside, his burning hole stretching and spasming with every breath he took.

“UUhuhhmmph… Ughu hmph mmhmm?” He pleaded after about fifteen minutes.

Standing watchfully from the door, Tyler shook his head. He wordlessly gestured to the incomplete model. Stefan rolled his eyes and quietly got back to work.

To the continued …

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