Resecured

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.

Gendermania

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.

 

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.

For Her Amusement

Mistress got upset at me yesterday. I had shared with her that I was just thinking about how nice it would be to be inside her, but made clear that I knew I wasn’t suppose to ask to have intercourse with her. You may recall that about a week ago she made clear that I am not allowed to ask to make love to her.

She felt that even bringing up having sex with her was not ok, even if it wasn’t a request. So she clarified that I am not allowed to even talk about penetrating her with tiny (her name for my cock), in any way whatsoever. She emphatically stated that it is entirely up to her “when, or perhaps more appropriately, if” I will ever be allowed inside her again. She said “At this rate, it’s looking like it will be about three years.”

I think that was an off-the-cuff remark. I hope it was. She hasn’t talked specifically about release times at all. We used to have sex several times a month, on average. But it’s been almost two months now that she’s denied me.

She has also talked recently about having me tattooed, although she’s still pondering what it would be. Her most recent suggestion is the word “Sissy” in large letters just above my ass.

I gave her a present after New Years that I haven’t written about here. Included was a card that let her know that, despite my aversion to needles, I was turning myself over fully to her, including needle play. She was looking at tiny in his cage recently, and remarked how she could just push some needles through my penis skin right between the bars of the cage.

Then she asked me if I would do that for her. I said “Of course, Mistress,” but my mind was reeling at the thought of putting needles through my own cock. It really is a tough limit for me to deal with. But I trust her so much now.

Last night she let me lick her clit until she had an orgasm. Tiny tried so hard to have an erection, with the smell and taste of her pussy right there in front of me.  I feel so fulfilled when she cums, her achievement of pleasure gives me the sense of being whole and complete. I crave for her to use me for her enjoyment. It’s nice to fall asleep with the smell of her on my face.

Yesterday she spanked my ass with a wooden spoon, just for fun. She made clear that I hadn’t done anything wrong. It’s just that she wanted to paddle my ass and see it get red. It arouses her to use me for her amusement like that. So to me it’s just another way I can please her.

Tonight she asked me to install something in our bedroom someday soon. She wants a chain hung from the ceiling that she can use for some purpose. Apparently she saw a video online today that gave her some ideas. I don’t know what she has in mind, but being naked and helpless before her sounds wonderful.

She’s waiting for me now in the bedroom, so I must not delay further tonight.

Piercing #12

I got quite a surprise on Saturday. My wife/Mistress/keyholder asked me to make an appointment to get my nipples pierced – that evening.

We did talk about it together, and I was fine with it. A bit surprised, but happy to let her make a decision like that about my body. I think it’s wonderful that she’s accepting my submission so fully. I want her to own me, and to make the decisions. This made it clear that she is quite happy to do so.

I’ve had my nipples pierced before. She loved the look of metal through my nipples, and I really liked them too. But they migrated and I had to remove them to minimize problems. That was about 6 years ago. Things healed well, although I have a little scar tissue.

Back then we wanted rings, so we got curved barbells when pierced. The piercing community has learned a bit since then, and for male nipples especially, straight barbells heal much better. So I now have 12 gauge metal through each nipple.

When they are healed in 6 months, Mistress wants to change them to stirrups. Like rings, they work well as bondage attachment points. She can’t wait for that.

You might be wondering about my other piercings, as 12 might seem like a lot. Here’s a run-down:

My first two were ears, which I still have and use (and love). Crossdressing just wouldn’t be the same without pierced earrings.

My next two were nipples, which didn’t last as mentioned above.

I then had a series of genital piercings: one dydoe, two hafadas, and two frenums which were the start of a ladder. The dydoe hurt the worst. And unfortunately they all grew out too. My best guess is that they had too much pressure and movement to stay healed.

The dydoe was particularly interesting because of our jewelry choice. On the back side was a captive bead, a short straight barbell through, then a bead with a ring on the other end. Like this but with a ring on only one end. The result was a handy attachment point for the head of my cock (e.g: leash). We thought it was really cool and fun.

That’s a total of 9. My recent Prince Albert was 10, and the nipples for a second time make 12.

We also have matching tattoos. She enjoyed getting hers. I nearly screamed and cried through mine.

And she’s talking more seriously about getting me tattooed again. I’m not sure what it will be yet. Stay tuned.

First 24

My first full day of true chastity has gone pretty well. Being locked up like this isn’t too physically different, but mentally it is.

I never had any intention of defeating my chastity devices. With both the plain JailBird and the CB-3000, pull-out was always an option. I guess I did pull out once of the plastic unit, but I didn’t masturbate, I just put myself back in. Now I cannot pull out due to the lock that goes through my PA piercing and the end of the JailBird cage. True chastity.

Physically the cage feels about the same. But mentally I know that I am truly trapped in it now. No escape. She has hidden her set of keys. And she said today she’ll be checking the emergency key box weekly to ensure that it isn’t tempered with. Without access to the keys, my cock is trapped in this cage for real, 24 hours a day. No erections, no masturbating, sitting to pee, and my cock is always less than 3 inches long at all times. And the craziest part? I helped make it happen.

The PA lock is very secure, but it offers a little more discomfort than the simple captive-bead ring that I got when I had the Prince Albert piercing installed. I’ll go into more detail about all the pieces and parts in a few weeks. I’m pondering a product review posting for Altarboy’s chastity site.

My wife seems serious about having this chastity experience be real. By that I mean under her control. I was a little surprised when last night she told me we’d have to get good at this “milking thing”. I didn’t even know she knew what prostate milking was, so that indicates she’s been doing some reading about chastity on her own. That’s a good thing, but it was a surprise to me.

She said she didn’t know much about milking. I reminded her that we have an Aneros unit that should make it easy (we haven’t used it). She said that’s fine, but she didn’t know how, so maybe she’d just have me do it. That sounds pretty humiliating. To not be permitted orgasms, and then to have to penetrate myself anally to force my built-up cum to dribble out. Well, she gets to decide that.

I also realized that milking isn’t usually necessary unless the time between orgasms is long – typically over a month. So that suggests that she’s planning for some long-term lockup. She did ask me what my longest time being locked up was, but I honestly didn’t remember.

After she locked me up yesterday I expressed a little disappointment that I hadn’t gotten to be inside her first. I had held out just a little hope that she might let me fuck her one last time. She was pretty annoyed at me even bringing it up. And she said I was not to mention it again unless I wanted my lockup time seriously extended. Her reaction both surprised and aroused me. She is serious about being in control.

I sincerely was kind of bummed, though. The last time she permitted intercourse was Thanksgiving, about two months ago. Fortunately I can remember it vividly. She’s allowed me some orgasms since then, by either her hand or mine. But I’ve been begging and longing so much to feel my cock inside her again. However, I understand now that sex with me is clearly not on her to-do list.

She continues to talk about her fantasies of black men and their nice big cocks. She teases me about how nice it would be to have one inside her, and how she’d like to make me watch as she fucks men with real cocks. I’m still not sure how serious she is. I do wonder if it’s more likely now that she intends for my cock to be locked up for a long time.

There was a black man she found on-line who lives nearby. She contacted him, but he hasn’t responded. It could be that he’s abandoned that profile. Or who knows, my wife could be talking to him by phone tomorrow. Or maybe she’s looking elsewhere.

Last night she allowed me to lick her pussy until she orgasmed. I find that so fulfilling lately. Her smell and taste really arouse me, so it’s a bit painful to try to get hard with the chastity cage. But that doesn’t matter, she’s using me to pleasure herself, and that means a lot to me. I feel very gratified, it’s a meaningful experience for me. I find her pussy beautiful and fascinating, and I will worship it whenever she asks.

I’m suspecting that my chastity experience will transition into a more long-term journey now. I may post less frequently, depending on what events occur. I’m aware of wanting to keep the interesting-to-mundane ratio high in this blog.

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