Well… I finally had “the conversation” with my PussyBoy last night.
He had just finished going down on me and we were snuggling in bed together. His penis was locked up, as usual, and was still twitching and throbbing as it does when it’s trying to get hard but can’t because of the chastity device. I was gently rubbing his balls for him in an effort to comfort him. He always loves and appreciates that.
I asked him how he thought our relationship was going, and how he felt about things. He said he was very happy and felt that our relationship was perfect. I asked him if he still had a hard time with anything. He said that he hates the punishment spankings, that they are very painful, and that he always feels terrible afterwards for disappointing me.
“Is that all,” I asked.
“Yes,” he responded.
“What about your penis,” I asked, “do you understand why I keep it locked up and have to restrict your orgasms?”
“Yes,” he answered.
“Remind me. Tell me why,” I asked.
“Because I’m a masturbator and you need to break my habit. And I can’t be trusted. And because I’m more respectful and worshipful and attentive to your needs when I haven’t cum in a long time.”
“Exactly,” I said.
“What about the strap-on, tell me how you feel about that,” I asked.
He hesitated a little. Then spoke. “I used to hate it. It used to be very uncomfortable for me. Sometimes it would hurt. But I guess I’ve gotten used to it now, and I know how much you like fucking me that way.”
“Do you like it now?”
He hesitated for a second, then answered “yes”.
“Good. I thought so. I’ve noticed how you don’t resist it anymore.”
We kissed and he thanked me for rubbing his balls, and kissed some more. My hubby has always been an amazing kisser. Then after a while I continued the conversation.
“I’ve been thinking that it’s probably time for us to take the next step.”
“What do you mean?”
“The next step in your training as a PussyBoy. You do want to be my PussyBoy, don’t you?
“You do want to please your Mistress, right?”
“Can I ask what the next step is?”
“Do you really want to know ahead of time, or do you want it just to happen?”
“I’m not sure. I guess I’d rather know.”
“Are you sure?”
“Do you remember what I told you a while back about how much Johnny likes to have his cock sucked?”
“Well…”, I hesitated to think about how I wanted to put it, “I think it’s time for you to start sucking cock. It’s the natural next step. And I think we’re going to start with you servicing Johnny the next time he comes over. Rather then a stranger.”
He got very quiet. I could tell he wanted to say something but was stopping himself. I’m sure that inside he was flipping out.
“Don’t worry. I think you’re going to make a really good cocksucker. You’re already very good with a pussy. And when you think about it, in a lot of ways, it’s the same skill really. And besides that… Johnny has a really good tasting dick. In think you’re going to like it.”