Well, there have been many changes (and many nappy changes) since billie was first exposed to Alex, my carpenter friend, as the true sissy he had become. The railing was fantastic and it really created the effect I was looking for in a toddler-style cot (or crib). I soon found plastic bumper padding at Toys R' Us to go around the sides of the bed, inside the rails. And, as a piece de resistance, Alex even presented billie with a soft, fuzzy, stuffed bunny (named "Poopsy") that spent Billie's nights with him in his new infantile bed.
Alex became a regular visitor and he and I developed a kind of "friends with benefits" physical relationship. All the while, I began noticing certain male residue in billie's nappy after most changes, especially after Alex had spent the night. I mentioned this to the ladies at the shop and Maria asked me if I had considered putting our little masturbator into a chastity device. I did a bit of research and found the perfect lock and tubing.
Then, one particular Saturday morning, when I was changing his nappy, it was very evident that billie had pleasured himself not long before I came into the nursery. "Have you been playing with yourself Miss Priss?" (By this time, billie had earned a few nicknames. In addition to being beckoned by the ladies at the shop with the monicker, "Sissy", he had also collected the names "Prissy", "Miss Priss", and "Twinkles". I'm not sure exactly who came up with them, but it was clear that billie did not like being addressed by any of those names.) billie, surprised by my question, was in a very vulnerable position, as I had a firm grip on his member while I was lotioning him.
I had placed the device in one of Billie's drawers the night before and it didn't take me long to slip the ring and the tube on and then lock the device in place. billie hardly realized what had happened, but then, after I took my hands away, I showed him the key. "Since you seem to find my nights with Mr. Alex especially arousing, I thought I'd give him the key. He can decide when you get unlocked. Won't that be nice? Buuut... you might have to do something special for him in order to get your own special feeling." The shock on his face was priceless as I pinned billie into two cloth nappies and then covered them with some frilled plastic rhumba panties. Pulling a "My Little Pony" top over his head, I continued, "Now come into the kitchen. I have a special treat for you and another surprise."
Once in his high chair in the kitchen, I brought out a new pink plastic bib, which had a little pocket along the bottom. On the front, Maria had so thoughtfully embroidered the words, "Sissy's cum catcher". I showed it to billie, and then tied it around his neck. I then went into the freezer and pulled out a banana popsicle which I unwrapped and handed to billie. "Here you are sissy. I want you to start practicing with this and, hopefully, in no time, you'll be ready for the real thing."
Billie got over the shock (and the taste). Once he realized that the only way he was going to have his chastity device removed would be if he pleased Alex enough, it wasn't long before billie became a regular part of our "benefits". He was soon greeting Alex and curtseying all over the flat as the sissy tried to please the real man. He knew that he had to ask, in a high-pitched babyish voice, to be given the honor to pleasure Mr. Alex.
After the act, if Alex decided he was worthy, he would remove Billie's device and I would unpin his nappy and start using the lotion on his privates. Only, for our entertainment, billie was required to speak in baby talk as I was lotioning him. At the moment he wasn't "babyish" enough, all lotioning stopped and his nappy was pinned. It only took twice for this to happen before billie got very used to babbling away like a two-year-old in order to get what he sought.
So that's pretty much how billie is today. It's amazing how far the haughty has fallen, but I believe that billie just found where he truly belonged, in nappies and learning how to be a real sissy.
Thank you for your letter Lucy. Like so many sissies Billie is obviously a chronic masturbator so your solution was the obvious one though with the interesting and exciting caveat to obey your friend as she would you and even though I may not personally approve, each of us that engages in this lifestyle makes their own choices.