Morphing Normality

It’s been 12 days so far in chastity this time, and to be honest, I’ve hardly noticed. It’s just the way things are now.

Sitting to pee is just second nature, I hardly think about it. About the only time it registers is around showering. And even then it’s just procedural: wash it, dry it, put a little lube around the base ring.

You’d think having a tight stainless steel locked to your penis would be a bigger deal.

We’ve had the JailBird for almost 4 months now, and I’ve worn it at least 95% of that time. Male orgasms appear to be a thing of the past now. They are simply not interesting to her at all any more. I don’t even find I crave them that much, although I suppose I could easily fall back into the masturbation habit. I don’t want to, though.

Now that I’ve experienced (what seems to be) female orgasms, there’s just no comparison. The last time we did that, tiny (her name for my cock) was only a little bit hard, barely at all. Mistress stimulated my nipples, touched and rubbed me elsewhere on my upper body, and guided me with her words to relax into building wave after wave of sensation. Eventually  I went over the threshold into this extremely blissful state, with my whole body participating in the sensory experience. It’s hard to describe, but oh so wonderful.

Mistress prefers me to have these “girlgasms” because I don’t get all cranky and grumpy afterwards. Right after, all I want to do is get close to her — even cuddling right next to her doesn’t feel close enough. I just crave feeling her next to me. The next few days I’m extra attentive and loving to her, so appreciative and present. I think we both prefer it this way.

And this works out pretty well with the whole sex-change business. I’m feeling impatient lately. I want to get on with this Becoming a Woman thing. I mentally put myself in that role walking around work every day. Even though am not ready to approach them yet to discuss it, part of me is so ready to come out — all the way out.

Over a dozen friends now know. And in about a month I will be coming out to my “church” community, fully transitioning there so that I can dress as my new female self every Sunday at services and during my other involvements there.

I literally have a closet full of clothes now. Probably enough presentable and normal female clothing for 1-2 weeks at work. I need more shoes though (what girl doesn’t?!). And Mistress has decided that I’ll be having a second pair of ear piercings so I can wear 4 earrings at a time (like her).

Friday I’ll be talking with my gender therapist about next steps to start hormones. We’ll also go over a rough timeline. Bring it on! Let’s get this thing rolling, I’m feeling so ready to make more progress.

Delayed Gratification

This post isn’t about orgasms, it’s about punishment. And it’s not that I enjoy punishment, it’s that Mistress enjoys punishing me.

A few days ago she caught me eating dinner from a regular bowl, not my dog dish (which she lovingly calls my “trough”). I honestly forgot, but this is like the third time in a few months. And she’s tired of me “forgetting” Her Rules.

Instead of our usual red leather paddle, she had out three other severe spanking implements. One is essentially a hardwood board with a rubber tire tread on one side. That packs a wallop. Things proceeded as at other times.

As she started the spanking she told me to explain what I had done wrong. In detail. And to clarify why it was wrong, and how she can be sure it won’t happen again. By this time my ass is quite pink and hurting.

She continues, though, explaining why this incident upsets her. And she talks about how she doesn’t see how she can be sure that I’ll remember next time. All the while she is wailing away on my now painful behind with the big paddle or the wooden hairbrush or the strop. I’m now yelling into the mattress hoping the neighbors don’t hear.

The intensity increases as she proceeds. She explains that she wants to see some bruises this time, and wants to be sure that when I sit tomorrow (as I do all day at work) I remember.

When she decides that’s enough (about 20 minutes later), she rubs some icy-hot type “ointment” (as she calls it) on my red and painful ass. This time she told me to go stand in a corner with my nose against the wall while she watched TV. She left me there another 15 minutes while the cream burned my behind. She turned the volume up to “drown out my whimpering”.

After I came home from work she asked how my behind was. I said “fine”, since that was the truth. And the frown she showed made clear her disappointment. Next time it will be even harder.

Now with more security

Mistress went to visit some relatives late last week. She took the emergency keys to our biometric safe with her. The keys to my chastity cage are in that safe, which opens only by her fingerprint. The safe is cabled securely in our closet.

Until now she had “hidden” those emergency keys in our house. She teased me at times to try to find them, but I dared not look as I didn’t wanted to be tempted to let myself out of chastity. The corporal punishment consequences for that would not be good, and I couldn’t live with the guilt. So it’s actually good that those keys are gone and locked in her relative’s gun safe over an hour away.

We still have a spare set of chastity keys in a tamper-proof box. But the security of my chastity significantly increased by her decision to relocate the keys to our safe.

Before she left she teased me pretty significantly. She reminded me about how why I was locked up: because tiny (her name for my cock) is so small and inadequate for her needs. She said she might find another guy to have sex with while she was away. Some stud with a man-sized cock that could really please her. And she asked me what I thought about that. I said “I want you to be happy, even if that’s what it takes” and I meant it.

In the end she was too busy with the relatives to do anything else — or so she tells me. I expect that’s true, since her finally cuckolding me for real would be a new level of humiliation that I’m quite sure she would want me to experience.

I’m continuing to come out to more friends about my plans to transition into a woman. Mistress is supportive, in fact we told her sister today. I’m hoping to start hormones this month, and am continuing to work with professionals on moving forward. Some days I’m scared about how fast things are moving, other days I’m frustrated that we’re not further along in this (roughly) 2 year process.

Mistress and I went out to a pretty busy restaurant this weekend, and I was dressed up pretty. She went with a rather butch look (jeans, jean vest) while I had on a nice dress with hose and matching low wedge shoes. I seemed to completely pass as a woman, which is great.

Lately I’ve had an issue with the chastity cage when crossdressing. Since the cage is bulky I have to really tuck it between my legs. Twice now one testicle has slipped through and escaped between the base ring and the base of the cage. That’s my own fault, of course, for ordering a base ring 2 sizes larger than I wore on my CB-3000 (which I’ve previously blogged about at length).

The last time it happened I requested the keys to get that testicle back into place. This time I worked pretty hard to push that naughty ball back through that narrow space. Nasty! I think I bruised it. Weird how I can not even notice it slipping out. Yet getting it back through is torture. Ah, what we go through to look beautiful!

For those curious about transsexuality, I’ll again recommend the book She’s Not There – A Life in Two Genders. I finished it, and it was very, very good. Hard for me to read in spots, as it got so personal. But very education, very readable, real, and well written.