The man, Kevin bought diapers but didn't wear them immediately. A week later his dress arrived. Seeing the dress with the petticoats and everything else that had arrived it gave him the impedance to wear them. There was no doubt that he couldn't use the bathroom while wearing his dress and the petticoat so he would have to wear diapers. Realizing that he has to start now, he took off his pants and his underwear and then took out a diaper. The diaper was thick as he wanted it and had tabs. He knew that pull-ups weren't thick enough for him. The first thing he did was pull the diaper around him, but he couldn't get it to stay up while he fastened the tabs. Then he tried it from a sitting position, that didn't work either. The only way he could get it on and properly fastened was to lay down and then wrap the diaper around him. He knew he would have to get used to wearing the diaper all the time if he was going to be able to pull it off on the day of the event.
With the diaper securely fastened, he put his jeans back on and went about his day. It was winter and with bulky clothing no one would know his diapered secret. He waited a while and then decided to relieve himself. But he just couldn't force himself to go. Kevin decided there was no hurry and he would let nature take it's course. Eventually, he did have to pee. He was sitting down at the time, but he couldn't go that way. The next thing he tried was to start walking and seeing if that would help. It didn't. Next he just stood up and let the pee flow, that didn't work. Finally he went into the bathroom and positioned himself in front of the urinal like he usually did, that didn't work either. He knew he had to go, but he just couldn't. It was all psychological. Since he couldn't go, he went back to what he was doing and waited. The pressure built and built and he went through the same ritual as he had before. Finally when he really needed to go, while standing in front of a urinal some pee escaped his penis and he had wet himself for the first time in twenty years. His bladder didn't fully release, but it was better than nothing. He knew that he would have to wear diapers every day all the time until the day of the event to train (or is it untrain) himself to use then.
It only took a few days before he could go in his diapers like he could before. But that wasn't good enough. It couldn't be obvious that he was going. He had to teach himself to go at any time. If he needed to go, he couldn't stand like a statue that would look weird and very embarrassing.He had to be able to go when he was standing, sitting, walking or even dancing. That was more difficult than he realized. It didn't take long before he could go if he was standing even if he wasn't in a bathroom, but what about walking or sitting. To do that took practice, he was determined to do it. It was his girlfriend's big day he didn't want to ruin it for her.
Soon he could pee in his diaper in any position he was in. The outside observer probably couldn't tell. But he had to do better than that. He had to teach himself to pee without even knowing it himself. His muscles would have to become so relaxed that he would go without any conscious thought. He wanted it to just dribble out without any restraint. That was the best way. If he did it that way, then he wouldn't flood his diaper by peeing all at once. The urine would just flow slowly as necessary, giving the diaper time to absorb the flow. He had already learned to feel comfortable with a semi-wet and heavy diaper. As long as the pee wasn't dripping down his leg, he didn't find any discomfort anymore with a wet diaper. The diaper was designed to keep him dry and he bought one that was extra thick for almost any situation.
It took some doing, but by the day of the event, he was completely secure in his diaper. He hadn't any control over his bladder anymore and wearing a soggy diaper became completely normal for him. The diaper even felt more comfortable when it was somewhat wet. A wet diaper could mold itself comfortably to his body in a way that a dry one couldn't. Today was the day and after his shower he put on his diaper as he had for the last several weeks. It was now time to get dressed for real and pick up his girlfriend.
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