Diaper Boy Stories

Damon stood naked in front of the long mirror attached to his closed bedroom door, or rather, naked but for the braided steel collar that had been locked around his neck and was never to be removed. He admired his reflection, appreciating the taut muscles of his abdomen, the way the deep color of his skin caught the light, the shadows his pecs cast onto his chest. He’d been spending a lot of time at the gym lately, and the hard work was beginning to pay off.

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His gaze traced its way down his body, brushing over his exposed genitals and down to his thick thigh muscles. He lingered on the scar on his knee from that time he’d fallen off his bike when he was twelve and had needed stitches.

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Damon had been a shy kid, quiet in that introverted, slightly nerdy way. At twelve, he’d been obsessed with Pokemon and anime and music. Now, at twenty-nine, his life was very different from what it had been like growing up back in Alabama, and his interests had followed suit. As a kid, he never could have imagined himself going to his first Pride event, and certainly not marching in the parade as he would be today. At twelve, he hadn’t even known Pride was a thing that happened every year, and he hadn’t known that other boys in the world had the same awkward feelings he’d experienced. How far things had come!

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Damon turned from the mirror and crossed the carpet of his bedroom to open his top dresser drawer. He pulled out a small vinyl case and unzipped it, then placed it on the top of his dresser with a faint smile. He returned to the dresser drawer and got out a half-empty bottle of lube, then closed the drawer. He squirted a small amount of the clear gel into his palm and then began slowly stroking himself until he was well-slicked and half erect.

Sighing, Damon patiently waited for his erection to subside, then he grabbed the thick, shiny metal ring from the contents of the vinyl bag and carefully slipped his testicles through, one at a time. He tucked his softened cock through the ring and it almost immediately began to stiffen again. Here we go again, he thought, shaking his head.

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Once the moment had passed and he was flaccid again, he pulled a metal tube from the vinyl bag and fed his cock into its opening quickly, before he began to harden again. Once he was stuffed into the chastity tube, he connected it to the ring with a small black luggage lock with a satisfying click. He started to pull the key out of the vinyl pouch before having second thoughts. More fun if I leave it here, I think.

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Damon went back to the mirror to admire his handiwork. He fingered the device, checking it this way and that in the mirror, adjusting his tight sack for comfort. The chastity tube’s polished chrome gleamed under the lights, enticing and seductive. Can’t wait for the smaller one to get here, Damon thought. This one is just a little bit too long, leaves too much room to try to get hard in it. Sir was right, a smaller cage is definitely needed. He felt heat rising in his face at the thought.

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Chastity had been a relatively recent addition to his toybox, but he’d quickly discovered how much he enjoyed the feeling of frustration and denial. And his boyfriend had appreciated how much more horny, attentive and needy being locked up made Damon.

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Damon returned to his dresser and opened the bottom of the three drawers, revealing several varieties of printed adult disposable diapers. He considered for a moment, then chose a diaper with a blue camouflage pattern, one of his favorites. It would coordinate well with the other gear he would be wearing, and blue was Damon’s favorite color anyway.

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He unfolded the diaper and laid it out on the bed, appreciating the rustle of the plastic. Damon had always been fascinated by the idea of diapers; he called them his 'gateway drug to the world of kink'. As a kid, he’d been completely certain that something was wrong with him for wanting to be put back into diapers. As an adult, he didn’t give a single fuck what others might think of his weird fetish, which was a liberating feeling definitely appropriate for Pride.

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Damon crossed to his nightstand and collected his small container of baby powder and a travel-sized package of baby wipes, but then a moment of inspiration struck and he decided to pull open the nightstand drawer and fish out a black permanent marker. He carefully and precisely drew a padlock icon on the front panel of the diaper, the international symbol for 'there’s a chastity cage under this diaper'. The naked man smiled and nodded at his handiwork, then he capped the marker and put it back in the nightstand.

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Damon went back to the dresser and, from the top drawer, pulled out a fairly small black rubber plug. Nothing too big, gonna be doing a lot of walking today, he thought. He squirted another small glob of lube into his palm and then set to work making the plug slick. Once he was satisfied that it would go in smoothly, he wiped his hand off with a sweet-smelling baby wipe, holding the slick plug by its flared base with his other hand.

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Gritting his teeth a bit, Damon lined up the tip of the plug with his tight hole and began gently but firmly pressing the toy against himself. He had never been a huge fan of anal play, but Sir had instructed him to plug up for the day and he wasn’t about to let Sir down. After a few moments of effort and one sharp moment of burning, the plug was firmly seated in his hole. Damon let the temporary pain fade away for a moment, and then he had to admit it began to feel pretty good.

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Damon carefully laid down on top of his bed and positioned himself on the diaper, adjusting and centering it. Between the snug metal chastity cage, the insistent buttplug and the crinkle of the diaper, Damon’s cock was desperately but fruitlessly trying to expand. The sensation could only be described as glorious, and he reveled in it as he felt his compressed manhood throb in its prison.

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He sprinkled a non-trivial amount of baby powder across his caged groin, then he pulled the front panel of the diaper up between his legs as snugly as he could manage. He smoothed down the wings and then, one by one, began attaching the tapes to the fabric landing panel. Once he was finished applying the tapes, he stood and wriggled a bit, testing the diaper’s fit. He unfastened and reattached the bottom left tape, then wriggled again. Better, he thought.

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When he had first begun talking to his boyfriend online, long before they ever met in person, Damon was hesitant to admit to his interest in wearing diapers. Even though the pair had met on a puppy play-focused Discord server and diapers were fairly common accessories within the human puppy community, Damon was uncertain how to broach the topic and worried about how his new friend Chris would react. After much hemming and hawing and stalling, Damon had finally, begrudgingly confessed his interest.

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Chris had been completely underwhelming in his reply. “That’s all?” he’d asked. “From the way you were carrying on, I figured this ‘secret fetish’ must involve something illegal, damn. You’re not the first pup I’ve talked to who liked diapers.”

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The amount of relief Damon had felt in confessing his deep dark secret and having it so readily accepted was unbelievable. From that point forward, Chris had made it a point to regularly ask for diaper check selfies, and over time Damon had begun to grow more comfortable with that aspect of his interests.

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Damon stood up from his bed and smirked at the faint Damon-ass shaped powder outline on the comforter. He brushed it away and then made his way back to the mirror. Not bad, he thought as he admired his padded reflection. I’m getting better at getting the tapes even. He let his eyes linger over the thick bulge of the diaper, staring at his reflection almost hungrily. The bulge alone made it clear that he was caged under the thick absorbent material of the diaper, and the drawn-on padlock was just the cherry on top. There would be no mistaking that Damon was a locked up pup.

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He reached down and pressed the diaper into his groin, appreciating how the chastity cage prevented even the slightest hint of stimulation from the action. Grinning in spite of himself, Damon walked over to his closet and opened the door. The left side of the rod was all daily wear and work clothes, but the right half of the closet was where he kept his favorite gear. Damon took out his beloved harness and his pup hood, both primarily made of black neoprene and matching bright, almost electric blue piping.

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Damon worked to get the chest harness on. This is easier when Sir helps, he thought. But Sir was busy dressing himself right now, and Damon eventually got his arms through the loops without help. The harness was a basic X pattern that laid neatly across his chest, and it was snug without feeling too tight. Damon decided to save the hood for last, and instead he got a pair of black cotton socks from the dresser and slipped his feet into them. He retrieved his favorite pair of well-worn rubber-soled black boots from the bottom of his closet and slipped his feet into those as well, then laced them up snugly. With as much walking as he was going to be doing in the parade, he didn’t want his feet to be able to shift around in his boots and cause a blister to form.

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Once he finished with the boots, Damon grabbed his pup hood and returned to the mirror. His transformation from 29-year old auto mechanic Damon Greene to playful, bright-eyed Pup Saber was almost complete, and putting his hood on was always his favorite part.

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He and Chris had been dating for nearly three months when Chris had suddenly announced that it was time for Damon to buy his first pup hood. They’d spent a few weeks exploring the many various available options online while Damon worked to develop a sense of who he was as a pup, and they’d finally settled on a white-and-gray hood with a detachable muzzle. Damon still had that first hood, and even though he’d moved on to several other nicer, fancier models since then, he still had an emotional attachment to that first, treasured piece of gear. That had been more than two years ago, long before Chris had formally adopted the role of Damon’s handler, long before Chris had locked the collar around Damon’s neck to proudly proclaim to the world that he was an owned pup.

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Things had changed so much for Damon since then, and he’d enjoyed fully exploring himself and his interests over those years. He’d been so shy at first, especially the first time Damon and Chris had attended one of the local puppy moshes, but he’d quickly found the sense of acceptance and community intoxicating, and it wasn’t long before Damon had become a regular attendee of those events.

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And now, he was about to march in his first Pride parade; not as Damon but as Pup Saber. Sure, as was the annual tradition, people were starting up the “NO KINK AT PRIDE” bullshit on Twitter again this year. But what the fuck is Pride about if it’s not about being your unashamed self? Damon rolled his eyes, then he brought his pup hood up and began working it over his head. It smelled strongly of neoprene, a chemical smell that immediately made Damon think of wetsuits. This was a new hood that would be making its public debut today, and it was custom-made to Damon’s exact measurements so it took extra work to get into.

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Once the hood was on, Damon lined up the eye holes and adjusted the muzzle a bit, then returned his gaze to the mirror. There he is, Damon thought happily. Pup Saber, looking cute as fuck. Damon never felt more like himself than he did when he was in his gear, and this new hood was designed exactly like how Damon imagined his pup self to look, even with the one pointed ear and the other floppy one.

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Damon smiled at his reflection. I’m so goddamn proud of you, pup, he thought happily. Don’t ever let anyone make you feel ashamed of who you are again, you hear me? Now, let’s go show everyone what a good pup you are!

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“Pup, are you ready? I can’t wait to see how the new hood looks!” he heard Chris call from the living room.

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“WOOF!” Damon barked loudly, tilting his head toward the sound. He opened his bedroom door and scurried toward the sound of Sir’s voice, already beginning to slip blissfully into puppy headspace. Today was going to be an amazing day, and Pup Saber was so excited to show off his pride!