My wife, Mistress, and keyholder locked me back into our high-security chastity device last night.

It was the first time I had the JailBird on since we got it back from having the base ring resized. So far it feels fantastically comfortable (as far as male chastity goes, anyway). She seemed quite happy to have tiny (her name for my cock) secured back in the stainless steel cage. The separate Steelworxx lock through my PA piercing prevents pull-out.

She had some trouble with the fingerprint scanner on our new bio-safe where she now stores the chastity keys. She ended up reprogramming it, which required the emergency keys. Fortunately those keys were still with us and not in her son’s gun safe over an hour away. So one strike against this inexpensive bio-safe. Hopefully, if and when she wishes to unlock me, it will scan her finger properly and open.

The safe is now securely cabled to a shelving unit in our master bedroom closet. It’s not super high security, but there’s no way I’ll defeat that without her knowing. She appreciates how convenient the key safe is there, yet it is still well out of reach of our bed. Her fear of me opening the safe with her finger while she sleeps has been fully addressed.

Once the emergency keys are out of the house, there will be only two ways of getting out of chastity. One is for her to open the bio-safe using her fingerprint. The other is me breaking the emergency key box, which she would know about also (since she has custom decorated the emergency key box). In a true emergency, I’d be forgiven, of course.

However, based on our new written chastity agreement, any attempt by me to defeat chastity or otherwise cheat is cause for her to abandon chastity in our relationship – forever. So that’s another strong incentive for me to be good. However, I prefer not to even be tempted to pleasure myself, and the cage addresses that for both of us.

At this stage I like being locked up. Stay tuned to see if my attitude changes as the weeks and/or months add up without any release for me. I’ve actually missed being in my cage. Being out of commission for three weeks due to that nasty skin infection really sucked. But it seems fully healed now.

I feel safer having my genitals caged. There is a sense of relief knowing that I cannot escape due to the lock through my Prince Albert piercing. And returning to the humiliation of always having to sit to pee feels strangely welcome and appropriate too. It’s kind of hard to describe, but I’m back where I want/need to be.

We have yet to see if the resizing was fully successful. Last night Mistress did a “stress test”, stimulating my nipples as I groaned, bucked, and tried to get hard. While there was no pain, it also wasn’t as intense as a few other times where I was super aroused and really, really straining against the cage. That’s when it would seriously hurt (in a bad way), as the smaller base ring was too tight against the base of my engorged genital area. I’m sure we’ll have a “super stress test” soon enough.

Last night Mistress paddled my ass harder than she has in years. My transgression was small (leaving the dinner dishes unwashed, particularly my trough), but she used it as a “correctional opportunity”. I think she was trying to get me to cry, which almost happened. I certainly was yelling a lot. Afterwards she had me apply one of those hot/cold ointments which caused it to hurt even more. It was actually painful to sit, and was tender all through the next day at work.

My first counseling appointment regarding my gender identity issues went well yesterday. After one more appointment and some tests she will have an evaluation and recommendation for me. I’m still not sure where this is all leading. But I am getting clarity that I’m unhappy about not being able to express my feminine side more in my daily life. Limiting my crossdressing to just at home feels like I’m denying a very real part of myself. I’m in the closet; I just don’t know exactly what it’s all about yet.

One awesome development is that my wife is starting to bond with my feminine self. Although she is bisexual, my “ditzy blonde” persona, which has been most prevalent in my past crossdressing, has never appealed to her in a sexual or relationship way. Sure, I was fun and an easy target for humiliation, but not all that appealing as a partner.

However, as I’m expressing my female side more, she’s seeing a new part of me that she is enjoying, perhaps even falling in love with (those are her words). When my long hair is down, and I have my soft pink or lavender pajamas on, and we’re cuddling in bed, she’s comfortable with me as her lesbian lover. Wow. I can’t say how great it feels to have that part of me accepted and appreciated (rather than rejected).

I’ve updated my stats to reset the clock for this new block of time in chastity. Mistress has given me no sense at all about how long she will keep me locked up. She doesn’t seem interested in release schedules, or scorekeeping, or any more formal method of determining chastity duration. It’s all at her whim. I guess I don’t mind that. And I suppose that could change, especially if she got some ideas on-line.

Anyone want to guess how long this lockup will be for me? I’ll watch for your comments; thanks.


I am expecting my wife and keyholder to decide to return me into chastity full-time sometime over the next week. My serious skin infection is healing nicely, but being on two antibiotics has really sucked.

I’m looking forward to putting the cage back on. I haven’t even tried it out since the resizing, and I feel sad about that. The new base ring dimensions will, we hope, solve the arousal/pain problem, allowing for long-term use with no need for removal.

I posted previously about discussions that my wife and I have had about my body, genitals, and gender. She teases me sometimes about having me castrated – which apparently is a very quick and relatively simple procedure when performed by someone qualified. She recently reminded me that I’m the one that brought it up early in our relationship, something I sincerely don’t recall discussing with her. But I suppose I did. She’s even teased about turning me into a full eunuch (no genitals at all).

More substantially, though, we’ve been talking about my gender role and identity. As I’ve been able to spend many more hours per week crossdressed at home (and sometimes carefully in public), things feel different. My wife commented how happy and content I seem to be when I am in my female role.

While at face value the comment didn’t surprise me, we talked further and I realized that she had a substantial point. I feel better, more complete, whole, myself, feminine, comfortable, at ease, happier, and so on when I am presenting as a woman. We both realized this could be something deeper.

Since that conversation we’ve talked a lot more, and I’ve observed myself and my emotions more closely. I was surprised about several things. I realized I do feel somewhat resentful of having to wear my “boy clothes” to work and elsewhere in public. It occurred to me that I have disliked my body hair for decades. Now that I’ve grown out my hair, I love brushing it, and I (surprisingly) don’t resent the extra effort.

We both took the BSRI (BEM Sex Role Inventory) test on-line (you can too – please add a comment about your results). My wife scored +18, I scored +11. Most men would score below zero (e.g. -20). Now since this test was developed in the 1970s, some professionals suggest it needs to be recalibrated for societal shifts since then. Still, it’s a well known professional tool.

Another wonderful aspect of all this is that my wife is completely supportive of this journey of discovery for me. She’s helped me find some gender identity counseling resources in our area. I have my first appointment next week. And she’s made clear that she is committed to me regardless of what genitals I may (or may not) have.

Since she is bisexual and tends to find women more attractive than men in general, there’s an interesting relationship dynamic there too. She said “It would be wonderful if you could get on hormones and grow some real breasts”. She is also happy to consider us living in public as two lesbians, if that’s where things end up.

Is this just some sex-change fantasy thing? It feels like more than that (to both of us). Until recently, when I have had the safety of this relationship and her unwavering love and support, I haven’t been able to even think such thoughts. It simply wasn’t an option to even consider, so there was no sense in seeing it as any more than a fantasy. But now, my sense of self and identity feels called into question, in a sincere and somewhat frightening way.

I shared with my wife a thought experiment I came up with. Consider this: You are offered all necessary gender alteration surgeries for free with no side effects or risks – would you do it? My wife’s answer for herself is a strong no. My gut-level instinctive answer is yes, but I feel myself block that answer with all sorts of fear and rationalizations and junk.

Miguel Ruiz, in his book The Four Agreements, beautifully clarifies the role of society as responsible for “domesticating the human”. I have been domesticated as a male. But is that who I am inside? How do I integrate these seriously feminine aspects of who I am without damaging my existing relationships (e.g. family, work, etc)? I easily feel overwhelmed about this lately.

I also realized that, as long as I can orgasm, which genitals I have doesn’t matter to me that much. My wife pointed out that my strong desires for chastity and useless penis humiliation could indicate a psychological dissatisfaction with my male genitals. That blew me away.

Am I just getting off on this as a fantasy? No, these discussions don’t turn me on, if anything they illuminate the fact that I’ve fallen into a rabbit hole, destination unknown. I’m experiencing a lot of confusion, many strong emotions, some loss of that sense that I know who and what I am, and some fear that I don’t know where this will lead. I’m open to all possibilities, including remaining just as I am after some counseling to get my head straight.

Oh, and my wife made it clear that we definitely would be getting a female chastity belt for me, if I end up as a woman. She wisely knows that the sexual servant/slut part of me would have an extremely difficult time being chaste. She also clarified that she would have no interest in a dildo attachment for my belt (to fuck her), as that’s what her other (likely black) male lovers would be for. But she certainly would look forward to strapping one on herself and fucking me in all of my holes.

Since this blog is primarily intended to be about my experience in chastity, I promise to return my focus to that – as soon as I am locked back up. This is only the beginning of my gender identity journey. And likely the beginning of some long-term chastity too, very soon.

P.S. In case it needs explaining, the title of this post is a tweak to the word “ambidextrous”, whose first dictionary definition is “using both hands with equal ease”. As I explore androgyny and my feminine side, it seemed to relate.


Mistress surprised me last night by telling me to “remove the ring”, which means only one thing: she wanted to have intercourse with me. What a treat!

I removed the 8 gauge captive bead ring in my Prince Albert piercing, applied a touch of lube, and was in position to enter her in near record time. Once inside her, it occurred to me that she might not let me orgasm. I found out later that she was indeed thinking about exactly that – after she had her orgasm(s), of course.

I’d been completely faithful lately under her restrictive honor-based chastity, avoiding even stroking tiny (her name for my cock). So the feeling of sliding into her warm, snug, wet pussy was so very wonderful. No hand job or blow job can compare to the amazing sensation of being inside her.

I took my time, and at one point I just stopped and stayed perfectly still. I had a sense, and I just watched as her orgasm built over the next 30 seconds and then crashed like a wave for her. It felt so fulfilling to be the object of her pleasure like that. I waited a bit, and then asked her if I could have an orgasm.

She thought about it, apparently changing her mind (as I found out later) and allowed me to proceed and cum inside her. My orgasm was tremendous. Denial really does amplify the eventual release, for me anyway. Good thing our windows were closed, I’d have woken the neighbors.

Last weekend we discussed a very interesting topic: my gender-identity issues. As you know, I love to crossdress and have been for decades. My wife has been wonderfully supportive, helping with makeup and hair and even buying me clothes and accessories. But this talk was about my body and my sense of my gender.

It’s complicated. Am I a woman trapped in a man’s body? No. Do I crossdress just for the erotic aspect? No. What do I get out of it? A feeling of contentment and fulfillment, of being myself and whole. And to finally have this side of me accepted is such a gift (my first wife completely rejected that side of me).

Yes, fantasy stories of forced feminization including male-to-female surgery is hot. But expressing my female side is more than a kink or acted-out fantasy. I so look forward to weekends now, as my wife encourages me to let this side of me out as much as possible. Saturdays I am her housekeeper, in white hose and my housedress and satin slave collar, scrubbing her floors and cleaning the house. Sunday she lets me dress however I like. Today is a black skirt, topped by a red/black fun blouse and feathered earrings she bought me. I did my own hair and painted my fingernails black just for today.

Anyway, she was genuinely curious about it all. It felt so wonderful for her to care so much to ask such intimate and meaningful questions. Obviously some paths along these lines could seriously change our relationship. For example, if I wanted to become a biological female and date other men, she was clear that we couldn’t remain married. Ok, that makes total sense. Fortunately, I don’t want to date other men!

She admitted at one point that she would find it hot if I had female breasts that she could play with and suck on. Being bisexual, she enjoys it all. She even admitted that us living together as either literal or apparent lesbians would be totally ok with her. And that sounded exciting to me too.

Don’t think, dear reader, that this is some whim or minor fantasy of mine. I’ve seriously considered my gender issues for many, many years. I would love to be able to live full-time as a woman in the world for some months to really see for myself how far this part of me goes. My wife has offered for us to take a long weekend vacation out of town and do just that together. I love her so much!

My wife even contacted a post-op friend of ours, and a TS-friendly therapist, and has some recommendations for me – professionals I can talk to. I’m seriously thinking about starting that dialog to see where this rabbit hole leads. As I’ve written before, I don’t think I’m a slam-dunk M2F transexual. Then again, if I could get to the point of sexual reassignment surgery as an option, I’d have to seriously think about it.

Perhaps I am an androgyn. I scored lowest on the masculine scale on the Bem Sex Role Inventory (which you can take yourself online here and read more about scoring here). I scored outside of the Androgynous zone just into the “Nearly Feminine” range. My wife took it too (scoring Feminine, not surprisingly) and when she saw my results exclaimed excitedly “we’re lesbians!”. Honey, it’s just a test we took online.

Androgyny is a new role for me to explore. My wife encouraged me to dress androgynously yesterday when we went out to dinner. It was fun. Here is an interesting recent article on an androgyn in the news. Although he’s way too skinny, I’m jealous of his ability to look so damn good!

My wife and I need to talk a lot more. I have no idea where we’ll go from here. I’m going to ask her about talking to a therapist. One thought I had is maybe I can get one of those cards that could keep me from getting arrested for being crossdressed. Yes, in my state it’s a crime for a man to be dressed as a woman in public (6th degree sexual misconduct, if I remember correctly). Stupid, but true.

I’ve been paying a lot more attention to what I’m noticing about other people lately. With women I notice hairstyle, makeup, clothes, fingernails, and especially shoes and boots; although I still observe and appreciate a fit and sexy body shape. With men I’m finding less repulsion (so many men seem conceited and slobby), and that a lot of body hair is gross. I’ve been trimming my own body hair short lately as I don’t like looking or feeling hairy.

I’d be interested in any comments folks have about gender-identity issues.


  • Calendar

    • September 2020
      M T W T F S S
  • Search