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.