On parole

I’ve been unlocked for 1 week now, although Mistress told me she thinks she should put me back into chastity. It might even happen tonight (she’s a little ticked off at me about something). I haven’t masturbated or even played with myself. I’m staying true to Her Rules and being chaste, even without wearing my cage.

A week ago she suggested we could have sex. So later in bed I asked her if I could cum inside her. She was taken aback, and told me that’s not what she had in mind. But if that’s what I wanted, well, ok. I wasn’t expecting such accommodation, but I wasn’t about to pass up the chance for another boy-gasm.

We were both disappointed. Intercourse wasn’t that great for her, and I found my orgasm to be a letdown. We both were left wondering if our experiments with alternative, “female orgasms” with me are changing things for me. I haven’t started hormones yet, so it’s not that.

We’ve been out several times together over the last week or so, with me crossdressed and passing in public, for dinner or shopping. Once with a good friend. I’ve outed myself as a transsexual to a handful more people. It’s getting easier to talk about with people.

I’m reading a book called She’s Not There – A Life in Two Genders. The author transitioned from male to female later in life, as I am doing. Some doesn’t fit for me, a lot does; some makes me want to cry it’s so close to home. It’s well written, more of a biography with some humor. If you’re curious about transsexuality, it’s a gentle introduction.


  1. Great post. I always read your blog updates but just don’t often reply. 🙂

  2. I might check out that book one day. I really don’t know much about this. Do you like being out of the cage?

    • Other transgendered people have it much harder than I do. Some have struggled seriously all their lives, hating their bodies, etc. One study showed that 41% of transgendered people have attempted suicide (and I guess I’m part of that statistic). I was very, very good at denial and stuffing, learned at a young age. But the cat’s out of the bag now, and I’m loving it! Being out of the cage is nice in some ways, but often I feel like I’m not serving Mistress as fully as I could by surrendering my genitals to her in that way. I’m locked back up now, and emotionally it feels better to me to be in chastity.

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