The next few weeks I started to adjust to not having a job. In all honestly, it felt like I had just switched jobs. Rebecca had started making me daily and weekly schedukes. It became far more Formalized than I had anticipated. She also asked for weekly reports on anything I hadn't finished and would text me through the day asking about progress.
She was generally very pleased with me, and had let me cum more than usual, meaning twice a week. She had sent me a strange text just a few days before our vacation that sort of worried me. She wrote:
"John you've been doing such a good job that I really think you're ready for the next level. I have some training videos and articles I want you to watch. I'm putting together a long email for you, but I'm not going to send it until after our vacation :) "
So, I decided to put it out of my mind and focus on our vacation. I was really looking forward to the break.
We left on a Wednesday and stayed until the following Monday. Rebecca let me fly there without my chastity cage since the pink plastic did have some metal. As soon as we got settled to my room she pulled it out.
"Ok here's the deal. I will let you go without this, but if you can't control yourself from touching that baby dick if you're it's going back on ok? Can you control yourself?"
"Yes plus I'll be with you the entire time!"
"Hmmm. Most likely." I had no idea what she meant by that, but maybe she was thinking about the times when she'd likely leave for a run or go to the massage parlor.
The first few days were a lot of fun. We spent most of the day at the beach. Rebecca would run every morning and I'd grab our stuff and go find an early spot at the beach for us to hangout for the day. We enjoyed the beach drinks too, lots of them.
On the second day I got pretty drunk, and of course I was very horny. Not being in my cage left me with an erection nearly the whole time. But because I was drunk I was also a bit bold. Too bold. I kept hinting at being horny all throughout the afternoon while we sat at the beach. Rebecca was reading her book. I kept rubbing her arm and admiring her body in her bikini. Finally she had had enough.
"John, stop begging and acting like a pathetic child. I will let you cum in this trip but not because you beg. You need to earn it. And earning it starts with self control. Do we need the cage back on?"
"No" I replied sadly. I sat and sulked for the next hour. Rebecca noticed and finally got up and straddled me on my chair. I was instantly hard again.
"I know it's hard baby. Seeing me in this tight little bikini all day. I know." She stayed rocking her hips. People were around but we were both drunk and didn't care.
"Does this feel good?"
"Yes."
"Good. But you have to learn self control. I have plenty of it. You don't think I'm crazy horny right now??"
"You are? I mean I hadn't noticed. And if you're horny why don't we go back to the room?" I asked.
