Lessons In Humility Pt 1 (Diaper)

By Kenji De Sade

Part one (?)


We’d been chatting online for a while, David and I. We’d never met, but we’d exchange more pictures then anyone should ever have of himself. David was 45, Irish decent, a black mustache and goatee, gray at the temples, salt and peppering toward the black thatch of obsidian hair adorning the top of his head. His eyes were a beautiful blue, accented by black thinly framed glasses. He said, and appeared to be about 6'1" with a large frame, the type that looks a little overweight, but oddly like it was just misplaced muscle. His body was covered in thick black fuzz with gray sprouts here and there. His cock was a menacing thing, about 7" of what looked to be a pretty thick hunk of meet, not overly gracious, but a damned good helping.

I was partnered, but very interested, so we’d worked things out with my partner. See my partner and I already had an open relationship, but an on going online thing seemed strange, however my boyfriend was more then willing, when he found out the whole idea was for me to get a chance to relieve the sexual tension I built up; by playing out games with this man involving the fetishes I’d acquired over the years which my partner, sadly, did not share. However part of the reason we were dating was do to the fact that he was greatly into the idea of me getting off, so my need to explore in whatever way possible was easy for him to accept, in fact he even offered to help make sure I did the things I was ordered to do!

So it was with this that my life as a diaper boy began, but not nearly how it ended. At first it was mild, David sent me an e-mail from time to time explaining my orders for a few days, to wear diapers for 8 hours here and there, to piss them while wearing them. There were a few rules that were standard procedure. I could not touch a diaper once it was secure and in place until I had used it and was permitted to remove it, I was only allowed to orgasm when permitted or when my partner and I had sex, mind you I was allowed to masturbate all I wanted. The rule attached to that was that whenever I came I had to have something up my ass. It was a way to make the subconscious relate orgasm to anal stimulation.

This last subject was further emphasized as the training progressed and I began listening to hypnosis files designed to make me more subservient, more attracted to the idea of wearing diapers, more comfortable to losing control when in diapers, and finally the most stimulating of the files, one designed to make it easier to orgasm simply from anal stimulation. I tell you that last one worked like a dream. While all the other files were working in a way I barely noticed, I quickly realized the benefits of being able to orgasm without ever having to touch your self. What I hadn’t realized was that more and more my mind was being drawn away from my ability to touch my own penis. Slowly my mind was being ridden of the burden of my own manhood.



As time progressed and this point became more and more clear, my mind began to wonder toward the idea of bending the rules a little, after all, your not guilty if no one knows right? However by this point my online Dom had me wearing 24/7. At first this had been an issue, as I’d wondered about the idea of someone at work seeing the bulk and realizing that I was wearing a diaper. I was assigned new hypnosis files and assured I’d be fine. Within our two-month relationship I was wearing all the time, and my boyfriend was making random checks through out the day to assure I was doing as told. With the constant vigilance of the diaper wearing by my boyfriend, my time to jack off into oblivion was rare and hard to come by. I was doing good, really I was, until David and James, my partner, decided I needed to start going through some anal training.

It was decided that I would start out my mornings cleaning myself out with an enema or two, showering, inserting a small sized butt plug, something that wasn’t too much strain for my ass to take, then I powdered myself, and put on my diaper. Latter during my lunch hour during my diaper change I would remove this first putt plug and move up a size, then re diaper myself. I started to express that the hard on this gave me might make the bulk even more noticeable at work, thusly increasing the risk that I might be caught. It was explained to me that I was a boy, a diaper boy, and needed to learn a few lessons in humility, and this was the mere beginning. After I got home, when James was waking up, he was a bar tender so our schedule left us seeing each other coming and going a lot. James would come into the bathroom with me and watch me change my diaper while he took his wake up piss, this way he could watch me change from the medium sized butt plug to one that was again larger in size.

After I was all changed I would usually help James cook a meal, and see him off to work, shortly there after I would report to David online. Usually I would clean the kitchen at this point; perhaps the bathroom and anything else David and James had discussed needed cleaning. I would perform these housekeeping tasks clad in nothing but a t-shirt, my diaper, and my socks. This was to ensure that our roommate Rick would get a chance to see that I was a humble diaper boy who was not ashamed of his place in life. Yea right! The first few times he made fun of me, calling me a big baby boy, telling me how silly I looked waddling and dusting. Eventually James was talked into getting me a onesie and from then on I at least had something to cover the diaper, but as Rick pointed out, it just made me look more like a silly baby boy.


I would be allowed one last diaper change and one last butt plug change, to an even larger size, the largest we owned thank goodness. It was designed to hold the ring of my ass open as far as the most bulbous part of the plug before it, and I swear the bulk of this one was slightly larger then my own hand. A cock ring was added to the mix, and then I was re diapered, drank five glasses of water, and laid down for bed with a hypnosis file playing on my mp3 player. It was difficult for me to get used to this, as the cock ring, the extraordinarily large butt plug, the diaper, the building in my bladder, and the building sexual tension had me squirming for at least an hour and a half before I could even think about actually resting.


It was due to this that I was brought to learn my strongest lessons in humility. James usually got in from the bar around 4:30am due to restocking and close up procedure once the clock hit 2:00 and the bar called last call. Some nights however if it had been a particularly busy night or he and the bartenders decided to stay in for a little after-hours bar tender bonding; he wouldn’t stroll in until 6 or 7 in the morning. As I left for work by 8 and liked to have a slow start this sometimes led to us having less time together before I left for work, this time however it led to me getting into big trouble.

I’d been in trouble before mind you, I’d touched my diaper a few times, which led to me having to keep my hand in mitts for a few hours. Or I’d try to hide my diaper from Rick, which led to me wearing a diaper to the bar and having James feed me enough drinks to have me leaking all over my pants before I was allowed to leave. I complained about it, so I was sent to the market to buy more diapers, leaking once again. But nothing was like this; nothing else had enticed the intensity of the training I was about to graduate too. Or rather, drop down too.

I had woken up so hard I was sore, my ass had gotten used to the plug, but I could feel it as I clenched the muscles in reaction to my cock being pressed against the warm wet diaper between it and the mattress. I had been leaking pre cum through out the night, a fact that was made obvious as my dick slid against the natural lubricant when I shifted my body from the first stirs of waking. In that instant my body shuddered, my hips thrusted, and in five strokes I made a decision to break the rules. It didn’t take much more then three more thrusts, but I had paused, I had consciously made the decision, I had taken time out to think it over, and I was boldly undoing all the time put into keeping me this frustrated, and it was amazing, it lasted for quite some time as it first started dribbling out, like pent up pressure in a tea pot starting with a low whistle and gradually building up into a crescendo of screaming. I realized this analogy fit when my ears adjusted past the blood rushing in them and to the loud moans of pleasure I was making as the dribbling turned into cannon ball blasts of lubricating diaper boy juice on the already piss warm insides of my diaper.

As the warm feelings of pleasure ebbed off of me and backed away, I opened my eyes to greet the warm rays of light shining through the window blinds and to my horror, shock, and utter dismay, James was standing over me with an utter look of disappointment. The look was so purely genuine that it hurt to see it. David made a tisking sound with his tongue and shook his head at me. My cock deflated completely before I could notice it and I felt ashamed of myself. David reached in his pocket without taking his eyes off of me and retrieved his cell phone. While staring me down he did something I hadn’t anticipated, he called David. I had never spoken to David on the phone; it hadn’t occurred to me that James would.

“David? This is James, I just caught the diaper boy being naughty.” The fact that I could not hear David’s response made me more nervous then I already was. My mind was racing and confused, so I sat there, slowly feeling worse and worse, feeling tears begin to well up in my eyes as James starred at me. His large frame filling the doorway, my only escape route from his gaze, his reddish beard framing the frown his lips held even as he talked. One big beefy hairy fore arm crossed over his belly, the other held to his ear with the phone. The conversation continued from James’s end.

“Well you see, he managed to avoid breaking to many rules while breaking one of the top two on your list.” there was a pause “No surprisingly it’s the other one, I thought he was doing really well too, his progress was mapping out well and everything.” another pause” Right, then I’ll fallow the procedure and talk to you latter tonight. I’ll make the proper arrangements and call his boss. Thank you David, look forward to seeing you” James hung up.

By now I was completely frozen, completely cornered, afraid, embarrassed and mostly ashamed. Tears had begun falling from my eyes but I still made no sound, I sat there and watched James as he reached into the closet to pull out my toy bag. I watched him unzip it and pull out the duct tape, the rope, the wrist and ankle restraints, a couple of fresh diapers, and my head harness with ball gag and blind fold. I watched him as he walked over to me still on my belly, still staring up at him, still laying in my wet cum filled diaper, still crying. He Soothed me then and said “Don’t worry Daniel, it’ll all be fine. Your going to be punished, what I’m about to do is in preparation of your punishment. What you did was bad, severely bad, and Daddy David and I have decided you need sever punishment and further training.” As he spoke he had begun putting the restraints on my ankles and wrists and had already moved on to rolling me over and changing my diaper, he cleaned me off, removing my spunk from my flesh, and wiping me down, then he lifted up one diaper and a small pick and began poking holes in the diaper, then he lifted my bottom up and placed this diaper under me, and began removing the butt plug

“Now, I had to poke those holes in the first diaper” he said as he turned the plug around slowly inside me. “So that when you start to pee, it can drain down to the next one as it starts to fill, I’m not sure how long I’m going to have to keep you here” He began pulling on the plug just as I was about to ask what he meant about keeping me there. Instead I let out a groan as he pulled slowly but steadily keeping constant pressure until the bulk started to push my hole further open. I’d been doing this program for over two weeks now, so this part wasn’t too bad, but with my legs up in the air and the stimulation, my cock began to react once again.

“My goodness boy! Your just too preoccupied with your cock aren’t you? We’ll fix that don’t worry. Eventually your cock wont even be of any concern to you.” with that he finished pulling the butt plug out, smacked my cock with the flat of his palm before he grabbed it to position it properly for the diaper that was being pulled up simultaneously to cover it. Shortly fallowed by the second diaper, which to my surprise he proceeded to duct tape the waste of, and a pair of blue plastic snap pants. Fully re-diapered and with restraints dangling from my appendages James began laceing the rope through the o rings on the restraints, and oddly, I thought, tied my ankles and wrists together, instead of spread eagle to the bed. He told me to spread my legs, to ensure I was comfortable around the bulk of my diaper, then tied the rope to the bed frame, and did the same with my wrists. As I realized I was being bound, with no knowledge of release or what was going to happen after I thought to ask.

“James, please, tell me what’s happening, what’s going on? Why are you diapering me like this and tying me up?” the pleading could be heard in my voice, and I struggled to show as much emotion on my face as possible, to no avail.

“See Daniel, that’s where I think the problem lies. You know I’m your boyfriend, and I only want the best for you, and David and I have been talking for a while, and he’s convinced me, daddy knows best, yet you keep questioning him. He’s helping you out, the way you asked, the way you negotiated with me, and your breaking rules you begged to have in place. Well, to stop you from doing that, were gonna make it harder for you to question what Daddy David says”


With that the gag was fitted into place and my eyes covered by the blind fold, the head harness was strapped and I was now bound, gagged, blindfolded, diapered, and confused beyond belief. It was only after the head phones for my mp3 player were put on my head that I thought “Well, it can’t get any worse!”

I’d undergone so many inductions by now that the hypno file didn’t take log, before I was spiraling down into a blissful trance of suggestions and guidence. I thought a few times that this one sounded strange, I didn’t seem to recognize a few of the words, but after they were repeated over and over I didn’t much seem to care, I just floated, unable to speak, unable to see, unable to move, unable to tell how long I lay there, blissfully drifting with words being spoken into my ears. Eventually I must have fallen asleep, I only realized this as the blind fold was removed from the head harness and my eyes focused on the man I’d only seen in pictures, the man who lives hundreds of miles away, and had only had virtual interaction with me to this point.

“Good evening boy” David smiled down at me “it would have been much nicer to see you under better conditions”

As my mind crawled out of it’s hole of sleepiness I began to realize a few things about the human bodies functioning. Apparently, when your gagged with a ball gag, you drool a lot, enough to cause a large cold wet spot beneath you when you wake. Secondly, a person can pee a whole lot, enough to add twice as much bulk to one diaper, let alone two. And thirdly, not all of that bulk was urine, for the first time I had done something I never thought I’d do, and I learned a lesson about the human body at the same time. After weeks of remaining open most 24 hour periods, and a little push from your subconscious through hypnosis, a person can let loose a lot of pooh in there sleep. I could smell it as soon as I realized what the extra bulk was. David could tell by my facial expression. And he laughed

“That’s right boy, your shitty behavior has turned you into a shity boy!” he laughed, which made me more embarrassed, and as I heard James’s laughter join in, it worsened ten fold. “Don’t worry boy, you’ll get used to it soon enough.” and with that I felt defeated and once again began to cry softly.

David soothed me by running his hand through my hair, as he began to untie my wrists and ankles from the bed. “Don’t worry boy, everything is gonna be alright, daddy’s here now.” with that he stood and began rotating my body, first rolling me onto my back, then seating me on my full diaper load. At first I felt as though I were sitting on a small pile of...something, and I was, soon I learned that something was squishy, and it began to spread up trough my crotch and around my testicles, up the back of my diaper, and I swore I could feel it smushing around the sides. Thanks to the duct tape however none of it seemed to be escaping, not even the liquids!


I gave David a look of question, attempting in my dampened state to ask what was happening, but he said nothing and lifted me off the bed and asked James for help hoisting me onto his shoulder, I began squirming and making noises of protest, but with the bondage, the smelly diaper, the weary ness from having just woken up, and both David and James, I could do nothing more then land on his shoulder and be carried off. Past our bedroom door, down the stairs and into the back seat of what appeared to be a rented SUV. The night air had been cold, and the vehicle hadn’t kept it out. I lay there chilly and watching through the car window, sitting in the back seat on my own filth, ands and ankles bound, gagged, and waiting for unknown events to occur, watching James and David bring down luggage with what I could only assume were my cloths. Listening to the two of them throw them in the back and what little of there conversation they allowed me to hear
“Thanks for coming down David, I was really surprised when you said it, but you’re right, it is for the best. You’ll only be gone a little while thought right? I don’t know how long I can wait!”

“It might take a while, the training I mean, I’ll call daily, within a week or so you and he should be communicating again, Don’t worry I won’t let you miss him too much.”

With that they closed the back hatch and said goodbye; David got in the front seat, buckled up and began to drive. While he drove he explained.

“Daniel, I know this is shocking, I know it’s all very sudden, but you’ve been slipping for a while now, making mistakes, you’re boyfriend and I just thought it would be better if you under went a little more strict training. We talked it over, for some time now. I’ve made a few suggestions, and he’s liked them all. I can’t tell you everything that’s going to happen, as it might ruin some of what I have planed, but I can tell you, the first week is going to be pure punishment. And I can give you a few preliminary rules just to give you some idea. You will only be allowed three diaper changes in a 48-hour period, less if I Don’t feel like changing you. Once were at my place, where I have the proper equipment, you’ll be locked into your and fist mitts. I doubt either of these will ever be taken off for any real length of time. You will not be allowed access to the Internet, the phones, really your only communication will happen out in public, and that’s if you’ve earned the right to leave the house without a gag in. Now I know you’ve always said the idea of being a big baby doesn’t really appeal to you, however that’s part of the point, the whole time your with me and are allowed to wear cloths, they will be baby print baby style cloths. In fact your meals will be from baby bottles and baby food jars, your bed will be a special crib I had made especially with you in mind, and you will crawl as much as possible, just like a baby. You couldn’t be trusted with responsibility, so most of them are simply being taken away from you. As I explained to David, I’m not sure how long this will take, but in the end, I’m sure he’ll be pleased with you, and that’s all that will matter.”

As well pulled into the airport parking garage, David explained that he would be releasing me from my bondage, and if I was a good boy, he would leave it off as we went through the air port and would wait until we got on the plain to go. He also explained that no, my diaper would not be changed yet. I had three changes every 48 hours, and frankly he didn’t feel I’d earned one yet. And we were off to the plane.




So I’ve added to the ending of the first story, and am re-posting the new extended directors cut precluding the beginning of this next chapter. Please, find your favorite chair or couch or computer chair, put on a fresh warm diaper, drink as many glasses as you can before you feel to full to swallow, and sit back and enjoy the continuation of...duhn duhn duhn (dramatic reverb)