Getting used a cock cage and diaper at night

I am the domme and the key holder of my fairly new submissive. He's younger, feminine and girly and he loves to be dominated. I met him through his step sister who is also one of my friends and an occasional lover. I started locking his cock about a month ago. He had been with me about a month because we were getting into the ownership/training thing gradually. When I told him we were going to a new level he first thought I was going to start using a different implement for his spankings and this seemed to excite him. He always gets a hard on when I spank him so I know he likes it. Anyway I told him no, we are staying with the strap and belt for now but we are starting is cock restriction. I took him to the classy sex store where i get a lot of our equipment. The owner is a friend. We showed him the models she had on hand and they included silicone and steel. I told him he'd be in steel so look the four over she had laid out. He chose one so we looked at some bondage gear and then left. When we got home I told him he be locked in after his bath and before bed. When we got to that point I had him strip naked and and gave him the cock ring part of the cage. He has worn cock rings so he knew how to quickly get into it. I had talked to a couple other girls who complained when they caged their boys that it was hard getting the cock into the metal cage. I solved that easily by putting some lube on is cock and stroking him just enough to start getting hard then I slid the cage over his cock and locked him in. As part of the ritual also had him lie on the bed and put him in wrist and ankle restraints attached to the bed. He wears nylon panties, bikinis, and a nylon short night dress to bed but tonight I gave him a pair of nylon briefs to wear after I unlocked his restraints. He sleeps in the same room as I most of the time and I noticed he was having a hard time getting comfortable. He told me it was because he couldn't get used to the metal cage. After the first few nights he figured out how to find a comfortable position.
The next challenge was the first Saturday night he was caged because Sat. night is when he receives his maintenance spanking. After the spanking I always diaper him and have him wear a pair of tight plastic panties. This particular Saturday would be his first spanking while wearing the cock cage. Since he the cage on had him bend over a padded chair before I administered the strapping. That way he wasn't laying on the cage. I give him the choice of keeping his panties on or pulling them down and that night he opted to keep them on which meant four extra strokes of the strap. I gave him the standard 20 strokes and then he asked for four more which I gave him. After I was finished I rubbed oil on his behind to sooth the heat. Next it was time for the diaper. After I had him diapered I asked how it felt and he simply said "crowded but OK." I gave him the panties which he put on. Once they were on he said that it was tighter than usual but that he liked it. That night he slept in my bed which is the routine. He's either shackled or leashed with a long leash attached to his collar. I asked which he preferred that night and he chose the shackles. It was obvious after we went to bed that he was having a hard time getting into a good position. At some point he drifted off. Like the first few days in the cage it was a learning process. To make it easier I diapered him with the plastic panties every night for the next few days and it worked. I didn't have him in diapers for the two nights before Saturday though. That next Saturday he had no trouble sleeping with the diaper and plastic panties on over the cage. I occasionally put him in a diaper and plastic panties of course, during the day. I asked him after the first day if he had any problems and he said he didn't mind it. So I guess the moral after that long story is to let other domes know that your subs won't be able to adapt to a cockcage for sleeping right away. Take your time.

 

One post script. I get his plastic panties from a source in Canada called b4ns.com. They have a great selection of various sizes, fits and s colors, both pull-on and snap-on.

 

The purpose of the diaper is first training and second because he has had wetting problems in the past which leads me to this addition to what I already said about diapers. My sub is still going to college part time. He hasn't started his new term yet so I had to get some advice about wearing the cage at school. The consensus is that it shouldn't be a problem and that goes for when he might have to be diapered as well. Another tip for those who have young men who have to be diapered but are not in chastity or at least not yet. One of my young cousins has to wear diapers daily although most days he stays dry. He complained that it was sometimes uncomfortable in hot weather to wear a diaper and plastic panties so his step mother had him wear regular nylon panties, the full brief style, with feminine over night pads in case of any leaking. he liked that because it was cooler on hot days.