This story is a work of fiction. All character within this story are fictional and any resemblance to any actual parties in mere coincidence. Please do not re-distribute for any reason without seeking the authors permission, though the author does encourage you to share with friends. Please feel free to contact the author, Kenji De Sade, for any reason at the address in my profile.
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Part one (?)
We had been chatting online for a while, David and I. We had never met, but we would 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 had worked things out with my partner. See my partner and I already had an open relationship, but an ongoing online thing seemed strange. However, my boyfriend was more than 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 had acquired over the years, which my partner, sadly, did not share. However part of the reason we were dating was due 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!
Therefore, 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 yourself. What I had not 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, you are 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 had 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 would be fine. Within our two-month relationship, I was wearing all the time, and my boyfriend was making random checks throughout 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 well; 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.
After I was all changed I would usually help James cook a meal, and see him off to work, shortly thereafter 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 than 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 had been in trouble before mind you; I had 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. However, 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 throughout 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 did not take much more than 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. It was amazing, it lasted for quite some time as it first started dribbling out, like pent up pressure in a teapot 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 had not anticipated, he called David. I had never spoken to David on the phone; it had not 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.