Last night my wife/keyholder allowed me out of the CB-6000 because she wanted to use me for her pleasure. However, by the time we finished watching a couple episodes of South Park, she was too tired. So I was able to sleep last night without my chastity device on for the first time in a week.

She woke up horny, and wasted no time in getting me hard and inside her. I took some time, letting her enjoy the sex we were having, and I focused on her. After a short while she had what seemed to be a very nice orgasm. I stayed inside her and we cuddled. I was hoping that I might be able to orgasm too — ideally without singing (see Violation).

Unfortunately some of our animals had an issue downstairs just then which required our attention. The moment was lost. Later she said I could have an orgasm, but I had to choose: either sing the song, or be locked up for another month. Damn! I nicely told her that I really didn’t want to sing the song, and she said that was fine, it was my choice, and that I should lock myself back up. Argh!

She said maybe she would give me another chance next week at the play party, where she might let me sing the song for our friends. I told her I wasn’t very likely to do that either. She said “Fine, it’s still your choice. I just know that it’s pushing a boundary for you, and I like to see you squirm about it. It just seems like a month is a long time, just because you don’t want to sing a little song.” I just agreed, dropped the subject, and locked Tiny (her name for my cock) back into his small plastic prison.

In my last post I said I’d write more about something we talked about a few days ago. I was locked up and she was sexually teasing me as she loves to do. We were also talking, and the conversation turned to crossdressing, which is something I like to do (I feel fortunate to be passable). She asked if I would like to be able to “live out”, meaning dress as a female all the time. I said that I would like that, and we discussed that in more detail.

Later in the conversation she asked me if I thought I was a man in a woman’s body, which I know is a basic issue with many transgendered people. I said no, but that I am extremely intrigued by the idea of actually being a woman physically. She spoke about having me castrated and how surgery could turn Tiny into a vagina. With some female hormones my body fat would redistribute, and I would grow some real breasts. Although I knew all this, I listened politely.

She asked me if I ever thought about that, and I truthfully answered “yes, more than once.” She asked me to rate how serious I would be about that, on a 0-10 scale. I thought about it, and said that it varied since sometimes I enjoy being male. My final answer was sometimes as low as 2, and sometimes as high as 7. I said I’d lived several decades as a man, and that I thought I would enjoy living some as a woman.

We discussed it some more, and I could tell she was really trying to get a sense for how I really felt about the issue. I don’t remember if I have mentioned here before, but her career has been in the medical profession. So if she wanted to figure out how to make it happen, I’m pretty sure she could accomplish it (legally). This conversation felt like an assessment of how likely I would be to provide consent for such a thing. I probably would not hesitate if she were sexually teasing me. That’s sort of frightening yet intriguing. Would my wife actually want to turn me into a woman?

She pointed out that we would still legally be married, even though we would both be biologically and legally female. That seemed pretty wild. She said that she would want to pick my new name, and I said that I would like that. One that came to her that we both liked was Mara.

Tonight we have tickets to a sold-out show, and we had talked about the possibility of me going crossdressed. I suspect it won’t happen for various reasons. Most likely I will start week 2 of being physically locked up. I note that, if this lasts a whole month, that will be 5 weeks without an orgasm for me. I really, really, really don’t want to sing that song, but can I last that long?

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