Transition Update

Life has been so busy!  I am continuing with my gender transition.  I’m working with some of the best professionals in my state, which rocks.  8 months now on female hormones, and I definitely have some cute breasts.  My wife loves to tease me about how much larger my ass is (yet she says she loves my “girl butt”).  I have filed paperwork to legally change my name, and have started talking to gender reassignment surgeons.

This week I’m going to talk to HR at my workplace to set plans in motion to transition on-the-job.  One day I will simply start as a female.  Yes, really.  I’ve learned my employer has recently gone through this with someone else already, which is heartening.  I’ve been living as a female for many months now everywhere in my life except at work.  It’s time to come out there and go “full-time”.

I received a comment or email from a reader who wondered if becoming a transexual was a natural or common eventuality for a feminized husband in chastity.  My short answer: no.  It’s a great fantasy, and I’ve loved the stories I’ve read on-line over the years.  But the reality of changing your gender for real in this society is very different.  I’m sure there is the occasional “forced” situation, but I estimate that’s far less than 1% in real life.  What you don’t realize is that there are plenty of transitioning people all around you.  Some estimates as low as 1 in 200.  Of course that includes the entire transgender umbrella, not just transexuals.

Some of the women you know might have been born male.  That’s just reality.  But please don’t ask them.  Think about it — a genetic female will likely be very offended that you thought they were born male; quite a buzz-kill on a date.  Like me, most transexuals want to transition and live the rest of their life as peacefully as possible.  I just want to be in the world now as a woman.  Eventually I will legally be female.  And my wife and I will simply want to get on with the rest of our (lesbian) lives.

Some aspects of my situation were not really that unusual:  a lifetime of private activities exploring my female side (crossdressing, reading TS stories, playing with makeup, wishing I was female); deciding to explore it more seriously after getting heterosexually married.  One aspect of my situation is very unusual:  my wife and I plan to stay together.  The harsh reality is that most relationships cannot survive one spouse changing their gender — I think the partnership failure rate is over 90%.  The suicide rate for transgender people is also very high (over 30%) — I’m fortunate to be a survivor, in fact.

But back to the question.  It very well could be that a husband willing to be feminized and put into chastity does have some latent gender identity issues.  But they may not be as serious as full-out transexuality.  There is nothing wrong with loving to crossdress (I did it for decades), and for many it ends there.  Other have a stronger pull away from their genetic gender, but life circumstances prevent them from acting on them (I was also there for decades).  A full transition is not cheap — at least $30,000 start to finish.  If you are interested in more details of transitioning, let me know.  I don’t want to bore my readers!

Let’s revisit my dog dish (see prior post).  I haven’t messed up once!  But I will relay one story.  My wife’s sister moved to our city about a year ago, and she comes over sometimes to chat or eat — or the three of us girls go shopping!  One day she was over and she brought her two little dogs.  I came home from work and saw my dog dish on the floor, and her dogs were eating out of them.  I didn’t know if my wife had told her or not.  And I didn’t dare ask.  But it was clear that my wife noticed me noticing, and she really got off on the humiliation that it provided.

I’ll end on a chastity development.  Today I’ll be removing my PA piercing.  That’s a major deal for me.  I’d wanted that ring in my cock for so very long, and it meant so much when my wife decided to have it installed.  But gender surgeons apparently recommend letting that hole in my penis heal.  I guess it makes sense, since they will be turning tiny inside-out when they surgically transform my male genitals into a vagina and labia.  It’s amazing what they can do today (google for “SRS photos”).

But removing my PA ring signals the end of an era.  No more chastity.  Having my cock locked up was such a focus and big deal to me.  And I’m feeling some loss about that.  Mistress still dominates me, of course.  But not with forced orgasm denial.  She’s threatened a female chastity device, but those always come with a waist belt, and she has never been ok with those.

At some point I’m going to sell my whole high-security chastity setup:  lock, JailBird cage, bio-safe, etc.  If you want to be notified, drop me an email or blog comment.  That will be a sad day too for me.  On the other hand, it truly does feel awesome in so many ways, to finally become the woman that I’ve dreamed of being — and to have my Mistress/wife with me on the journey!  Heaven!

A New Phase

Well, it looks like I’m well on my way to never needing to have tiny (my wife’s name for my cock) locked into a chastity device.  Several times she’s happily remarked on how well my “chemical castration” is coming along.

What she’s really referring to are the hormones I’m on as I progress in my transition to becoming female.  I’ve been on estrogen for 2 months now, with maybe a little breast, and hip growth (but hardly any so far).  The sprio though, which blocks testosterone, is what she was referring to.  It reduces the male sex drive and, over time, shrinks the testicles.

Recently I realized that my PA ring may not be long for this world.  It was integral to the 100% secure stainless steel chastity cage we used not that long ago.  But it’s getting uncomfortable now that I’m tucking my junk away to look more feminine “down there”.  And sometimes that damn ring gets really uncomfortable, squishing things in strange ways, particularly when sitting.

It also occurred to me that it may be a problem later when I go to have sexual reassignment surgery.  Since, basically, the penis is turned inside out to make a vagina, it probably won’t be good to have a hole in it.  That’s 1-2 years away at this point, but still something I’m thinking about.

I asked Mistress about it recently, and she suggested that I may as well just remove the ring.  That was a bit of a shock to consider, since my PA piercing will probably close up and heal over pretty quickly (a week or two maybe?).  What shocked me was facing the end of serious male chastity in my life.  Funny, that hit me harder than not having sex.

The extensiveness of this blog probably makes it pretty clear that chastity was a pretty important thing to me.  Masturbation, sex, and male orgasms certainly were also.  But they aren’t any more.  I’ve changed, and I’ll continue changing.  Not only has my male desire for sex been suppressed, my whole sense of sensuality is changing.  I’m amazed at how erotic simple touching can feel now.  I’ve always been a tactile-sensitive person, but hormones have turned it up to 11.

Anyway, lately I’m coming to grips with letting go of my manhood.  Chastity represented that, in a way.  My cage was an illustration of how I needed to have it controlled, lest it be out of control.  Thinking about selling my awesome metal penis prison makes me sad.  It’s a rite of passage, I suppose – if atypical.

Of course, to see me typing this with my hair up and wearing this bright, fun sun dress – you wouldn’t guess that I’m struggling with my masculinity.  And I’m not, really, I’m doing well at letting that go, because I feel so great as a woman.  But chastity – wow, letting go of that part of my life is harder.  Necessary, but a heart-felt loss.

In terms of my transition, I’m living at home and in public as a woman over half the time that I’m not at work.  My immediate family knows (parents, children, siblings), and probably 100-200 friends.  We have new friendships in the transgender and transexual community, which is wonderful.  This fall I plan to come out at my workplace, which I’m expecting to go well.  Between then and now I’ll be legally changing my name.  Serious progress.

It’s been busy, with extra appointments, investing time in new relationships, additional shopping to get my closet ready for going full-time, hair removal activities (laser, IPL, electrolysis), etc.  Mistress and I are both really looking forward to the time when we can just get on with our new lives together, without so much focus on these transitional steps.  Again, necessary, but sometimes frustrating.

And she is excited to be growing into a lesbian relationship.  Being bisexual, this is seriously working for her.  She can’t wait for me to have fuller breasts, a vagina she can have men of her choosing use, and labia she can torture.  After all, I’m still her submissive pet, regardless of my gender.

Just thought I’d update everyone.  Thanks for reading.  As always I’m open to questions and comments.

Male Chastity Devices

In this post I’m going to discuss some of my perspectives on male chastity devices. I will focus on their purpose and security issues. And I will detail how we dealt with these issues in my current experience of chastity.


The two main purposes I see for locking up a man’s genitals are: control and prevention. Much has been written about the ways that a keyholder can control the sexuality and behavior of someone locked into chastity. What and how to control is a very broad topic that I will not delve into today. My links page has a few good articles about control.

Prevention is an easier topic, being more limited and practical in nature. What activities does the device prohibit? I see three primary levels of prevention: stimulation, orgasm, and intercourse. Devices can prevent all, some, or even none of these. So when selecting a device, it seems important to know what you wish to prevent, and whether a given device actually achieves that goal.

In my situation my wife/Mistress/keyholder wants to prevent orgasms and intercourse, but she also wants access for stimulation as she loves to tease and deny. To prevent stimulation as well, a properly fitting full belt style device could be used to block all access.

Devices that enclose the penis can severely limit stimulation, but many can also transmit the sensations of a vibrator. For some men such vibrations can be enough to achieve an orgasm. For others (like me), a vibrator against my chastity device can only tease, arouse, and frustrate.

Tube or cuff style devices which fully expose the glans would not work for us. A tight, even painful, shaft restriction does not prevent me from being able to masturbate to release. It’s possible that I could even have intercourse and orgasm with such a device. I think they look interesting, but I suspect they would prevent very little sexual activity for me.

Another, secondary aspect of prevention is visual. Some devices show more of the male genitals than others. Cages and clear plastic models allow the penis to be seen, whereas tubes, opaque plastic, and full belts keep the cock partially or fully out of sight. Since men are sexually visual creatures, one opinion is that the inability to see their own manhood will increase the psychological impact of a chastity device. I think that would be true for me.

One advantage to visibility is that it allows the keyholder to see and possibly access the cock for teasing. I believe cage designs offer a sweet-spot of both visibility and minimal access for stimulation while severely limiting or preventing the ability to orgasm.

Visibility is also closely related to ease of cleaning, which in turn can relate to wearing time. Having to remove a device for periodic cleaning can be desirable or undesirable. In our situation, we appreciate being able to stay clean without having to remove the device.

Another secondary prevention feature of almost all chastity devices is limiting or preventing erections. Attempts to get hard will reinforce the state of being in chastity. Sometimes this can also interrupt sleep patterns due to nocturnal erections.

Some devices offer optional spikes to more severely discourage erections. Some keyholders enjoy this punishment effect, which can discourage behaviors like using pornography or having sexual fantasies, physiologically training him to actively avoid arousing situations. Keyholders can also use it to inflict genital pain by purposely arousing him.

A final secondary aspect of some devices is to prevent the use of urinals. I was able to stand and pee with my CB-3000, but not now. Always having to sit to pee reinforces being in chastity and can be humiliating. Some keyholders enjoy reinforcing this with sissiness or feminization teasing. All my boy underwear has been replaced by panties, for example.


I’m going to use the word “inescapable”, but I must define it first. I consider a chastity device inescapable if the only way out of it requires: 1) damage to the device, 2) damage to the genitals, or 3) access to the key(s).

True inescapability is impossible in reality. I use the term instead to indicate a sufficiently high level of effort that the wearer would not or cannot accomplish.

I could easily escape from the CB-2000 and CB-3000 devices that we have used before. Without a piercing, I don’t believe that any ball-trap style device (even my current metal JailBird cage) could contain me. The flaccid penis can be amazingly flexible – stretching, bending, twisting, etc.

Tipping a ball-trap device forward allows me to easily pull out the back. When soft, I could just as easily slip back into it. I also know I’m creative and handy enough to easily defeat something like the Points of Intrigue. While I never did escape and masturbate, I always knew I could.

Trust enters the equation here. If chastity security relies on trust, then I don’t see the sense in spending money for a more physically secure device. In the extreme, no chastity device is even needed – the keyless keyholder just needs to set the rules (e.g. no orgasms without permission). “Faith-based” chastity, anyone? 🙂

For me, like most men interested in chastity, this level of sexual trust isn’t feasible. That’s a primary reason we get interested in chastity devices in the first place — we fail at self-control.

That’s why I am now locked into an inescapable chastity device. Neither of us wanted to have any worries once it was locked on and the keys were secured. And we’ve achieved that for much less than the cost of a full belt device (which Mistress doesn’t prefer anyway).

Like essentially all men in chastity, there is no way I would damage my chastity device or my cock in order to escape. Either type of action would be obvious to a keyholder and entail consequences much more severe than remaining in chastity. And this is a curious point to explore further.

One common consequence that a keyholder will build into a chastity agreement is the permanent termination of chastity in the relationship for breach of security. While this allows for a “safeword” style exit strategy, such a clause is likely never exercised. Being in chastity is a big deal, and ruining it forever is a huge deterrent. This aspect also eliminates lock picking as a viable approach.

A keyholder can thus leverage a strong interest in chastity into a very serious real-life chastity experience. Neither damage to the relationship nor ending chastity forever are ever seen as worth that risk. He ends up trapped, figuratively and literally.

Access to the keys can also be a trust issue. Are the keys hidden? Does she wear them (and is that really inaccessible)? Does he have a copy? How secure are the emergency keys? Again, relying on trust here defeats a goal of being in inescapable chastity. Fortunately one need not rely on trust to inexpensively attain key security.

Our Security System

The device I wear has two sets of keys. One pair of keys is for the PA-lock (which prevents pull-out). The other pair of “keys” are the only way to remove the high-security screw holding the cage to the base ring. That leaves us with two full sets of keys: her set, and an emergency set.

The emergency set of keys is encased in an inexpensive plastic key box specifically made for this purpose. Once closed, it cannot be opened without breaking it. So any access to the keys will be obvious to the keyholder. I keep this box in my car in case of a true emergency. Our agreement is that Mistress reserves the right to inspect it at any time. She has also custom-decorated the box itself, so replacing it with a new one isn’t an option.

Her set of keys is locked in a safe in our master bedroom. It’s a low-end but very secure biometric safe that opens using her fingerprint. She had me securely cable it into our closet, far away from our bed, to ensure that her fingers cannot come in contact with it while she sleeps. The safe can also be opened by a backup key, which she has hidden. Once she is confident about the safe working reliably with her fingerprint, it sounds like she will keep the backup keys with a relative (locked in their safe). Another option would be to use another emergency key box for the backup keys.

PA lock and JailBird

PA lock and JailBird

A penis piercing is a vital component of my inescapable chastity. Since a belt-style device is not for us, and since I can pull out of other devices, that only left one option. My Prince Albert piercing allows the the tip of my glans to be locked to the end of the JailBird cage. This completely prevents any possibility of pulling out.

Many other chastity devices can utilize a PA piercing to prevent pull-out. One concern I had about units with a PA “pin” was that a truly flaccid penis might stretch enough to pull off the pin. Since we wanted as short a cage as possible, this would have potentially left more shaft for “unhooking”. A longer cage might mitigate this, but at the risk of pulling on (and possibly migrating or damaging) the piercing hole.


One of our goals for chastity was to eliminate the need for trust-based chastity enforcement. A PA piercing was necessary to achieve our security goals. We also took some simple and relatively inexpensive steps to implement serious key security.

The device we selected allows for stimulation and well as easy cleaning and long-term use. The cage length restricts me to a humiliating length of less than 3 inches, and forces me to sit to pee.

The result is a device which I now wear continuously. I know I can’t escape it, and that helps. I don’t spend any effort trying to defeat it, leaving me more energy to focus on pleasing my keyholder. Your mileage may vary, but this is what we have found that works for us.

I’d love to hear your comments.


I blew my change to be released from chastity for an orgasm yesterday. Dumb, dumb, dumb.

Saturday morning we woke up and were laying in bed chatting. My wife/Mistress/keyholder told me she’d like to unlock me to ensure that tiny (her name for my cock) “gets a good bath”. By this she means a good (usually harsh) scrubbing.

The prior evening we had watched Margaret Cho’s “Beautiful” comedy stand-up performance (excerpt here).  Margaret is awesome, we love her (but Cho newbies may want to check out her previous tours first). Anyway, part of her act was going off about stinky dick. So I jumped to the conclusion that my wife was concerned about that with me. Certainly that was true with the CB-3000, but I can keep the JailBird nice and clean. In addition, putting the PA lock back on is a bit of a hassle.

So, keeping my defensiveness in check, I commented back to my wife that I am very able to keep it clean, and that “a bath for tiny” really isn’t necessary. She dropped it for a short while, then brought it up again. And again I said we didn’t need to do that. You can probably guess what she said next. I didn’t see it coming – go ahead, call me an idiot.

“Well, I was going to release you today and let you have an orgasm. My plan was to get into the shower with you and let you soap up my naked body. Then I was going to wash tiny until he squirted. But twice now you argued with me about unlocking you, so you can just forget about it now.”

Fuck!  Fuck, fuck, fuck. I didn’t say that, but I thought it really loud. What a dunce.

And that was that. It’s Sunday afternoon now, and she’s not said another word about it. But that wasn’t my only screwup that day. Oh no.

In my last post I mentioned that I wanted to offer my newly hairless body to Mistress this weekend in a special way. She approved a “surprise” scene for Saturday afternoon. When the time came, I gave her a note and asked her to give me 1/2 hour to get set up, then she could come up to the bedroom.

The note outlined that I would be tied to the bed and gagged, naked (but in chastity of course). My cage would be covered to hide my useless genitals, but in a way she could rub herself on it for her pleasure if she wanted to. The rest of my body was slick with massage oil, and the note suggested she could feel free to arouse herself by rubbing her body on mine. I thought she’d enjoy a bondage/lesbian/sensually erotic scene.


She came into the bedroom as I was finishing up with the wrist cuffs. She said “Here, let me help” and she tightened them both and locked them to the corner bed restraints. Her enthusiasm at securing me surprised me. My ankles were already tied out. I had a ball gag in and she tightened the blindfold. “Comfy?” she asked rhetorically. I nodded. Then she left, going downstairs to her office for what I estimated was about 1/2 hour.

At this point I had no idea what was going on. I laid there bound, gagged and naked, unable to do anything but await her return. Part of me wondered if this was a way for her to reinforce the objectification – leaving me as a toy to be used if and when she wanted. Another part of me was worried that I had messed up.

When she eventually returned, I got my answer. “So, according to your note, you had a particular scene in mind, right?” I nodded weakly, concerned about where this was headed. “Well, what if I’m not interested in that? And by the way: I’m not. So let’s review your note.” She read the note to me, word for word. “It’s good you put the part in about me doing whatever I want to you, because that’s exactly what I’m going to do.”

With that she sat on the bed next to me. The next 10 minutes were torture, consisting of her flicking my nipples painfully and tickling me relentlessly. I was yelling and begging for her to stop, thrashing around in my 4-point restraint. After that she took our leather paddle and reddened the inside of my thighs. Then some more tickling and belly-button stimulation which I also greatly dislike.

She tortured me as I yelled and thrashed, and I heard her laughing. Yes, she was really, truly enjoying the hell out of this. I was in tears from the torment. She said “You know I’m a sadist, right?” I nodded, as we both know that’s one of the reasons I wanted to marry her. She continued this torture for a little while longer.

But I wasn’t prepared for the next part. Behind the blindfold my eyes went wide as she asked “Where are my needles?” OMG. Just after New Years I gave her a present: scores of new hypodermic and acupuncture needles, along with alcohol wipes (this post). Through the ball gag I directed her to a dresser drawer. I could tell from her voice that she was serious.

I felt her rub a wipe on some skin on my leg, and then heard her opening one of the needle packages. “I haven’t had a chance to use these yet. And you said I can do what I want, didn’t you?” All I could do was whimper, torn between not wanting to be her pin cushion and wanting so much to sincerely please her.

“Stay still, don’t move,” she said. I felt her pinch the skin on my leg. I braced myself. I really hate needles, and she knows this. I felt the needle enter my skin as she pushed it through, and I bit hard into the rubber gag as I screamed. “That’s one,” she said, “I think we’ll start with five.” My whimpering protests were unintelligible through the gag.

I bit down hard as she swabbed, pinched and poked me four more times. Then she sat back and caressed around the areas. “Don’t thrash around now, we don’t want one of those needles poking into your testicles now, do we?” In my mind I saw a needle dangerously close to my tight scrotum poking through my chastity cage. Must … be …. still.

Seeing my blindfold had slipped, she adjusted it back into position and said “Keep this in place. If it moves again, that will be five more needles.” Ok, I think I can do that.

“Now I’m horny,” she said, and she climbed on top of me, still fully clothed. “Do not move around, I don’t want any of those needles poking me. Understand?” I nodded, truly scared for me and for her. She ground her crotch against my chest and worked herself up to an orgasm. In doing so, her chest was in my face and it moved the blindfold.

As she carefully got off of me, she noticed the blindfold was out of place again. “What did I tell you?! That means five more needles.” I whimpered and whined and begged. “Do you want more than five?” That shut me up, briefly anyway.

I felt more alcohol swabbing, followed by more skin pinching and poking. My teeth dug into the gag each time as I screamed during and cried afterwards. After the last one she laid down next to me and caressed my face, feeling my tears. I panted and calmed down, feeling very loved by her attention and grateful that the torture seemed over.

“Would you like to see?” she asked? “I’ll release one hand and you can get the rest.” She did so, and soon I sat up and removed the blindfold. I expected to see ten needles still in me. But there were none. There was just one place where two little blood spots indicated where one needle had been. Nine of the “needles” were mindfucks. I cried.

I unfastened my ankles and she covered me with a soft throw. We cuddled together, and I sobbed with my head on her chest and in her arms. I really am needlephobic, and this was an intense scene for me. Her aftercare was perfect, and eventually I settled down. We talked and processed things, we both learned some things about the other, and our intimacy deepened once again.

Overall it was an incredible scene. But she made clear that she wants to be in charge of them. Me defining the scene was not a good move on my part. I thought I was offering something new to her, but I see her point now and my error. In my quest to make her happy, I can do better.

Twice yesterday she sent me out crossdressed for errands. One to pick up dinner, and later to pick up a DVD. Today she send me out grocery shopping for ingredients for a new recipe she wanted to try. And yesterday as usual I was in my housekeeping dress for several hours cleaning floors, vacuuming, doing dishes, and other chores at home.

We have a local kink/BDSM party coming up in 2 weeks. Last time she put me and my newly received Prince Albert piercing on display (prior post here). I’m wondering if she will keep me chaste until then. That would be a full month. I’ve daydreamed about being milked at the party. I fully expect to be displayed again so people can see my cage and PA-lock.

But after this weekend I’ve learned my lesson about suggesting scenes or activities. The moral of this story? Mistress is in charge.


Mistress is completely ignoring tiny (her name for my cock). She’s more interested lately in punishing me and letting me pamper her.

Yesterday she found another reason for a serious ass-paddling session. It was a financial mixup on my part, actually a potentially major issue. Everything was fine, but it might have been a disaster. She was not happy that I had slipped up on this vital detail.

When I got home from work she told me to set out her spanking implements in our bedroom and wait for her. I arranged the paddles, canes, crops, and other items for her convenience. She arrived and simply pointed me towards our bed. I lowered my pants, laid on the bed, and waited for her to get to business.

She asked me to explain why I needed to be punished. I told her, and she repeated some things back to me, reinforcing her points with hard swats to my bare bottom. I thought ahead enough this time to position a pillow so I could yell, scream and cry into it and not bother her so much with my wussy noises. It was a good thing, because this session was a little more intense than the last one.

This was my second ass beating this week, and she made it clear that she expects better from me. This session included ten hard swats with her favorite cane, which burned terribly. I think she used each implement for at least ten impacts. Afterwards she applied the icy/hot cream to my red ass herself. This increased the residual pain, and also left me smelling rather minty for hours.

Then she put a medium butt-plug in me. That might not have been so bad, but we had a meeting to attend. Between the meeting and driving, I spent over 2 hours sitting, pushing the plug uncomfortably deep, and squirming to find a comfortable sitting position. She was please to be able to torture me so effortlessly, and in public. The lube left my ass squishing as I walked, which felt humiliating.  After 4 hours she allowed me to remove it.

At bedtime she had me rub lotion into her beautiful legs. I wasn’t allowed above her calf, as this was service, not sexual. Most every night I provide her a back rub to help her get to sleep. She loves foot rubs too. I hope someday soon she allows me to give her some sexual pleasure, but I know that she will tell me when she wants it, and I am not to beg.

Apparently I didn’t tighten the security screw enough when I put the JailBird together a few days ago. Today I noticed the screw had loosened. It’s not a major problem, as the cage stays together just fine even if the screw is loose. I just don’t want to lose it. It came with one spare security screw, but I don’t want to end up having to buy more screws. So tonight I’ll ask her to open the safe so I can use the keys to tighten it well.

Even if the screw came out, all that would happen is that the cage would separate from the base ring. I still can’t escape from the cage. The lock through my PA piercing keeps the end of my cock secured to the far end of the cage. So I can’t pull out, and I would still have no meaningful access to tiny.

I had some concerns that the larger base ring might change the wearability of the JailBird somehow. It certainly is looser at the base, but it’s not a problem at all. It’s still snug enough to support the weight of the cage. And as mentioned above, I can’t pull out anyway. Heck, the whole thing could slide down and the end of my cock would still be locked to the far end of the cage. The resizing was all about increasing the comfort for 24/7 use. That aspect appears to have been a complete success.

I had some suspicions that a guy at work might also be in chastity. I’d noticed him use a stall to urinate once or twice when urinals were available. But this week I observed him using a urinal, so probably not. I guess I used to stand once in a while when I was wearing my CB-3000. So I suppose anyone could possibly be locked up, and I’d be hard pressed to know.

Ok, I have a challenge for my readers. I’ve been thinking about ball-trap chastity devices, and I know that when I’m flaccid I could pull out the back of any of them. And it’s my theory and assertion that anyone could escape that way. Cocks can shrink up quite a bit, and I just don’t see how the geometry of these ball-trap units could maintain security.

So my challenge is this: has anyone seen a video demonstrating how a seriously flaccid cock could not escape from a ball-trap chastity device? If so, please post the link as a comment. I’ve read reports of some people claiming they can’t pull out of a CB-X000 device. But honestly, I don’t believe it. It’s my assertion that such devices, by themselves, cannot be considered secure. A guy can claim it, but a guy can lie.

Even my own JailBird, by itself, wouldn’t even come close to keeping me secure. Without the PA lock, my flaccid dick could easily slip out the back. Can anyone provide some video evidence that some men find these ball-trap devices to offer reasonable security? I suspect not.

I understand very well that not everyone wants or needs 100% secure chastity. It can be difficult and expensive to get to that point. Some people are really good with the honor system. But relying on that doesn’t really require a chastity device then, does it? My point here isn’t to make anyone feel bad – your kink is ok. My point is more for keyholders, to clarify the reality (as I see it).

I could easily have been cheating daily when I was wearing my CB-2000 and CB-3000. I didn’t, but my point is that I could have, and some men might very well do so and insist that it’s so secure they can’t.

I can also see the value in having a less severe way to transition from no chastity into some chastity. Maybe some folks aren’t ready for the real thing. I’ve never been there, if I could have gone straight into 100% secure lockup from the beginning, I’m sure I would have. The problem then was the cost. Today I’m pretty happy to have full security for under $500 (cage + PA lock).

I’d love to hear your comments about my rambling on chastity security. And please post video links if you know of any demonstrating ball-trap device security. Thanks.


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.


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.


Lockdown Pending

My resized JailBird is on it’s way back. I expect to be locked back into chastity in just a few days. These will be my last few days of genital freedom, probably for many weeks. It’s up to her, of course.

I’m really looking forward to being locked back up. I miss it. I feel like I’m not contributing my sexual submission to our relationship. And I will appreciate not having to struggle against the temptation to masturbate.

One thing I realized lately is that the cock cage actually stabilizes my Prince Albert piercing quite nicely. The way my PA-lock is situated between the cage bars keeps things in place quite consistently. Lately, being unlocked, tiny (her name for my cock) is loose in my panties, and he often seems to find an uncomfortable position for the captive bead ring.

The PA-lock easily takes the place of the ring. The photo in this prior posting show how the ring (and lock) is used with the cage to prevent pull-out.

Not much else to report. I’ve been battling an infection for most of the last week. Nothing sex or kink related, as far as we can tell. Just one of those things. It sucks, it hurts (in a bad way), and hopefully these antibiotics will clear it up in a few days.

Our schedule this weekend is busy enough to prevent us from attending a kinky party tonight. I think Mistress’ plan was to show of my caged cock to everyone. If I had to guess, she’d likely handcuff me to a basement post again for all to see (as she did previously). But the JailBird is in the mail, rather than locked around my cock. So it wouldn’t have worked anyway. Plus I’m not feeling well.

Next month, though, watch for her to do something to parade my chastity in front of our kinky friends.

Permission to Enter

“Make your tiny cock hard, and rub it against my clit. I want an orgasm,” my wife and Mistress said.

This would be as close as I’ve been to being inside her for over two months. The prospect of feeling her warm, soft pussy lips against my unlocked cock was going to be quite a treat for me. Just imagining how the moistness of her labia would feel against the head of my cock made me quickly get hard for her.

I guess being out of my chastity cage for a week (while it gets resized) has more benefits than I realized.

She pulled the bed covers down, revealing her unclothed bottom half. Slowly she bent her knees and separated them, revealing her genitals to me so seductively. As I moved into position, she pulled her glistening pussy lips apart, revealing her sensitive nub that apparently needed some attention.

I lowered myself and gently put my cock head against her opening. She startled – apparently my PA ring was cold. Damn. “I don’t want that ring there; slide up further,” she directed. I did so, and my cock head approached her belly button. My shaft pressed against her clit now, and she started enjoying the pressure.

She began to grind herself against me, and I realized that this position gave me basically no glans stimulation at all. So I redirected my attention to ensuring that her pleasure was uninterrupted. It didn’t take her long to climax, after which I snuggled in and just hugged her as she floated in that post-orgasmic state.

Eventually she opened her eyes, smiled, and asked “I suppose you’d like to go inside me?”. I responded “Of course,” fully expecting her to decline as part of her ongoing teasing. She said “Well, it’s probably going to be a hassle to remove that ring, you probably need some tool from downstairs…” She likes to leverage any excuse to deny me.

“Actually, Mistress, the tool happens to be right here on the dresser,” I said. I could tell by her smirk that she was amused that I had anticipated this possibility. Even so, I expected only to be taunted further. Just because I’m unlocked from chastity for a few days doesn’t mean she would allow me to have intercourse with her. I briefly fantasized about being allowed to just rub my cock head against her now very wet pussy lips for a minute or two, and then she’d roll over and go to sleep.

Which is why I was shocked when she said “Ok, take it [the ring] out.” I quickly removed the 8 gauge ring from my pierced cock and rejoined her on the bed. Just to be sure, I asked: “Mistress, please may I cum inside you?” I couldn’t believe it when she agreed. Despite his lack of use, tiny (her name for my cock) remained hard enough for me to slip inside her wonderful, warm, wet, snug, delicious pussy.

It had been well over two months since she had last permitted this. As a result, the intensity of the sensation was very high, and it didn’t take me long at all to orgasm. It’s good that she had hers first, because I I don’t think I could have lasted long enough to bring her over the edge. It was so incredible to feel her vagina hugging tiny again. I felt extremely grateful to have been allowed that pleasure.

As we chatted afterwards, I got the impression that she was going to want more intercourse going forward. She wanted that pleasure for herself. I’m not sure how that’s going to work when, probably early next week, I’ll be locked back into chastity. Taking my captive bead PA ring out is super easy. Removing the PA lock and the JailBird is nowhere near as quick. But I guess that’s my problem, not hers, right?

Of course I’m also assuming that she meant more intercourse with me. Although she teases me a lot and talks about sex with other men often, I don’t think she’s serious about actually doing it. Sometimes I think I must be crazy to want that and to be locked up for months myself, instead of having sex with her myself.

Having experienced a little serious chastity and denial, I find myself drawn deeper into it. During these days of being unlocked, I find myself a bit uncomfortable about having free access to my cock. I’ve even urinated standing up a few times, and it feels like I’m getting away with something. It’s as if something in me has switched over to chastity as the norm for me now.

In related news, I completed a modification to the PA lock. There was a part of the brass locking cylinder that stuck out. The corners of that little metal piece would poke into my scrotum providing wincing-level bad pain on occasion. It turned out to be quite easy to file down that piece and round the remaining edges. It doesn’t diminish the lock security in any way, and it should be much more comfortable.

I actually am really looking forward to getting locked back into my resized JailBird. I sent it back to have the base ring enlarged. The problem was that when Mistress would get me seriously aroused, that base ring would get so tight I could barely stand it. Because the PA-lock prevents pull-out, a larger base ring isn’t a security concern.

I expect that the new base ring and increased lock comfort will allow me to wear the JailBird continuously for weeks or months. Whatever Mistress wants.

Temporary Freedom

My wife, Mistress and keyholder has approved a modification to my chastity cage. It is being mailed back to Mature Metal today. They offer base ring resizing for only $10, another great thing about them and their products.

At the moment, tiny (her name for my cock) is wearing only the PA-lock through my Prince Albert piercing (mine looks a lot like this photo). I’ll probably be switching back to the captive bead ring that came with my piercing, as I need to modify the PA-lock slightly. There’s a piece on it that has pointy corners that can poke into my scrotum at times. It’s caused wincing bad pain a few times just sitting at work, so it’s time to file those edges down.

Although I had only worn the JailBird for a week, I had gotten very used to it. It feels so strange to have it off. My genitals hang down loosely, all floppy and flaccid. I feel surprisingly vulnerable between my legs now. This makes me realize that the cage gave me a sense of safety, being locked into the constrictive cage.

I’m also struggling with temptation. I could masturbate. I know that would greatly displease my wife, so I shouldn’t. But there is a physical and psychological urge that is compelling and a challenge to keep contained. I’m not willing to lie to her, as that destroys the mutual trust that is core to who we are today. And for myself, I don’t want to be a liar, especially to her.

I told her about feeling tempted. She asked me straight out if I had masturbated, and I told her the truth (no). I said “I’m quite aware of how bad the consequences would be if I did.” Her response: “No, you really have no idea how bad it would be for you.” Ok, it’s pretty damn clear that I won’t be cheating just because I am sans-cage for a few days.

Last night we watched the South Park episode featuring the Shake Weight (season 14, disk 3). It was hilarious how they overlaid masturbation onto that exercise device. Afterwards my wife wanted to masturbate me. I wasn’t going to say no, since it had been a week since my last orgasm. We had to take the cage off anyway to ship it back for resizing.

In bed she jerked me off with her hand, the PA-lock still dangling off the end of tiny. I was so aroused by her touch that I came very quickly. I wasn’t even fully hard, and I lasted only a minute or so. It was a very intense and enjoyable orgasm. My wife commented quite a lot about how it didn’t take me very long.

She also mentioned that she was thinking about letting me fuck her, as long as I was out of the cage already. That didn’t happen last night, and she might just be teasing me. I’m a bit worried that I won’t be able to last very long, like last night. Pleasing her is important to both of us.

This makes me wonder: might chastity be turning me into a premature ejaculator? If so, that could be one more reason for my wife to seek out other men for sex. And another thing to use to humiliate me. I can’t help that I’m so sensitive after a period of denial. My wife probably won’t mind it, though, as she seems fine with forgetting about intercourse with me anyway.

She continues to notice and comment about black men. At dinner tonight a man with very dark skin was at a nearby table, and she spent quite a bit of time looking at him and talking about him. It’s such a mind-fuck for me, because I don’t know if she’s sincerely interested for herself (which is what she acts like), or if it’s just to make me feel inferior (which it does, probably also her goal). It may also just be a tease because she wants to watch a black man overpower me and fuck my ass (or so she says).

In other news, the tea aprons for my housekeeping dress finally arrived. Mistress wants me to do some work for her tomorrow morning, and then I’ll be her maid for the rest of the day. I expect to be cleaning floors, vacuuming, cleaning bathrooms, etc. At least I’ll be able to tuck tiny down under, and avoid the embarrassing bulge under my dress.

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