Diaper Boy Stories

Trip grinned to himself; this had been much easier than he expected. He looked down at the unconscious wolf lying on his bed, snoring loudly, and chuckled. The guy that had sold him the stuff had promised it could take out an elephant, so one black wolf had been no match for the tranquillizer. Justin was sure to be unconscious for at least another several hours, plenty of time for Trip to put his plan in motion.

The hard part had been getting the larger wolf back to Trip’s place and into his bedroom. Thankfully, Nana had been out again, having a Friday night bash with “Brenda and the girls”. With much grunting, swearing, and more than a little dragging, Trip had managed to get Justin inside and on his bed. Now came the fun part.

Trip began stripping Justin of his clothes, again with much effort. Undressing dead weight was proving to be a surprising challenge. But Trip was dedicated, and eventually he had the wolf out of his hoodie, t-shirt and jeans. Justin was lying in a heap on Trip’s bed in just a pair of nicely filled-out red boxer briefs. “Shame you’re such an asshole,” Trip muttered as he appreciated Justin’s nearly naked form. The athletic wolf was muscular without being chunky. His jet-black fur was offset with patches of a smoky gray that ran down the front of his body, accentuating his musculature beautifully under the right lighting. Justin’s tail was long, thin and tapering, and it ended in just the smallest tuft of pure white at the tip.

“Let’s get those undies off, you won’t be needing those for a long, long time,” Trip muttered. Trip worked the boxers off Justin’s form, slowly shimmying them down the wolf’s thick legs, at last leaving the wolf completely naked. He tossed the boxers onto the pile of the rest of Justin’s clothing.

Trip then walked into his closet and returned a moment later holding a box of his supplies. “Let’s make this look good for the camera, shall we?” he mused as he unpacked the box on the bed next to Justin’s unconscious body. One very, comically thick diaper, baby powder, a relatively small butt plug, a chastity cage, a bottle of lube, an oversized baby pacifier, and a snap-crotch pastel blue romper covered in teddy bears made their way out of the box one after the other.

Next Trip worked to get the diaper under the unconscious wolf. It proved to be a great deal more work than Trip had expected, but after nearly twenty minutes of stop-and-go work, he managed to get the crinkly undergarment lined up roughly where it needed to be. He stepped back and took a few pictures with his phone, then sprinkled plenty of powder, stark white against the wolf’s black fur. Another few pictures down.

Trip then picked up the chastity cage with a wicked grin on his face. The device was made of very shiny metal and it came with several rings of various sizes. Eyeing the sleeping wolf’s bulging sack, Trip decided to start with the second largest ring. He worked the ring around Justin’s tight sack and sheath, just like he’d practiced on himself countless times before. Once the ring was secure, Trip squeezed a bit of lube into his palm and then slowly began stroking Justin’s sheath. “I’d be lying if I said this wasn’t kind of hot,” he told the sleeping wolf with a smile. Justin, for his part, merely snored.

Once the wolf’s sheath was slick, Trip began slowly working it into the chastity cage. It was going to be a very tight fit, but the ring size he chose seemed to be fine. Once everything was lined up where it needed to be, Trip snapped the lock closed. “Say goodbye to your little buddy, little buddy. You won’t be playing with him for a good while,” Trip said, stifling a giggle.

Next, Trip picked up the buttplug. It was fairly narrow because Trip was certain Justin had probably never had anything up his ass before, and he didn’t want the pain to be enough to wake the wolf. Trip lubricated the plug and then ran his slick finger along the entrance to Justin’s hole. “God, you’d just die if you knew what was happening to you right now, wouldn’t you?” Trip carefully but firmly inserted the tip of the plug into Justin’s slick rosebud, pushing until the device was all the way in. The wolf’s cock stirred a bit at the sensation, as much as it could while trapped in its steel cage, anyway. Trip wiped the lube from his paws using Justin’s discarded t-shirt, then snapped another few pictures, always making sure to angle the camera to get Justin’s face into the shot.

Trip sprinkled a bit more powder over the chastity cage, then pulled the front of the diaper up over Justin’s chastity bulge. The effect made it look a lot like Justin was tenting his diaper. “Oh, perfect,” Trip muttered. He taped the top tapes down securely, then did the same with the bottom tapes. He carefully rolled the wolf onto his side with a good deal of effort, fastening the tail tape snugly over the base of Justin’s tail. Trip stepped back to admire his handiwork.

The diapers he had chosen fit the large wolf’s form perfectly, and from this angle it looked like Justin was rocking a hell of a hardon in that diaper. Of course, it was really just the curve of the chastity cage pushing through the diaper, but a casual observer certainly wouldn’t have seen it that way. Trip snapped another dozen or so pictures, from many different angles. “Not gonna lie, big guy, you do look kinda hot like this. Oh well, you’ll still be embarrassed half to death so I guess you might as well look good doing it, hmm?”

Trip hoisted Justin up and fought the unconscious wolf’s form for a few minutes, dressing him in the snap-crotch romper. Getting the shirt part on was challenging enough, but getting the back pulled down over the wolf’s extremely diapered ass enough to get the snaps to connect required a lot of rocking the wolf back and forth. “Good thing this tranquillizer stuff is working so well,” Trip grumbled.

At last he got the front and back panels on the romper to meet between the wolf’s legs. The overall effect was striking, really emphasizing the ridiculously thick diaper bulge between the wolf’s legs and making it painfully obvious how juvenile the big muscled jock looked right now. After a moment’s rest, Trip slipped the pacifier into the wolf’s muzzle and then took several more pictures of the “sleeping angel”, putting his body in various poses for the camera.

Once he was satisfied that he had enough blackmail evidence to destroy the wolf, Trip then went back into the closet and returned with a second box. This one was full of various restraints, and Trip thought it would be wise to make certain Justin was well secured before he came to. Trip first removed the pacifier from Justin’s mouth and inserted a much larger, bulbous one in its place. This one buckled around the back of the wolf’s neck and had another strap that was meant to be wrapped around his muzzle to hold it closed around the gag. Trip then slid the wolf’s paws into a pair of baby blue leather bondage mittens, rendering the wolf’s claws and fingers useless. He attached a pair of matching leather wrist restraints to the wolf’s thick wrists, then attached the other end of each to his cast-iron bed frame. He did the same with the black wolf’s feet, spreading them apart and attaching them to the footboard. A waist restraint was looped around the wolf’s tight waist, then Trip ran it down and under the bed and back up the other side, securely attaching the wolf’s middle to the bed.

At last Trip was satisfied that the wolf was secured. Through it all, Justin never moved and only made some small snoring sounds. All that was left to do now was settle in and wait for Justin to wake up and meet his fate.

“I can’t fucking believe this worked,” Trip said to himself quietly, triumphantly. All these months of careful planning, of using inheritance money left to him by his parents to order the supplies he needed from online sex shops and BDSM boutiques, of working to obtain high-powered animal tranquilizer illegally… Trip had been so certain that something would have to go wrong and bring his plan to ruin. And yet here Justin was, tightly bound and gagged on Trip’s bed, wearing only a butt plug, a chastity cage, and a huge, thick, babyish diaper.

Trip looked over the results of his handiwork. Justin was trussed up like some sort of giant toddler, every part of his body under Trip’s control. Trip could feel himself growing aroused at the sight of the formerly intimidating wolf jock lying there looking so powerless and ridiculous in his giant baby diaper. No, won’t do to rub one out right now, Trip thought. Later, once all this is done, I can look at all the pictures. Oh, speaking of, I need to upload them to the cloud for insurance. I’ll do that while I wait for Sleeping Beauty to wake his ass up.

Trip took a seat at his desk chair and began tapping on his phone, uploading all the pictures he’d taken to the cloud. He wanted to have plenty of room free on his phone so he could video this next part. The corgi settled in to wait for his prey to awaken, a contented smile spread across his face. The wolf would be awakening to a whole new world soon, and Trip couldn’t wait to tell him all about it.