My Hands Free Journal

Monday I had a lesson in the importance of planning ahead. I had an appoint to have blood drawn in preparation of a doctor's appt. next week. All good so far. I signed in and was handed a cup to pee in. Shit. I forgot about that. I was locked in my belt and couldn't possibly avoid making a mess, with very little going into the cup. I moved away from the desk for privacy and called Mistress. I explained my situation and heard Mistress laugh in response. When she had caught her breath, she told me that she would come over and let me out. I told the woman behind the desk that I couldn't go right now. Not exactly a lie. I sat down trying not to notice the annoyed looks from the technician. Mistress arrived 2 hours later. She grabbed me by the wrist and led me into the toilet. With the door locked behind us, she told me to stand still. Mistress then took down my jeans, and panties, and unlocked my belt. While doing this she hummed The Stripper. She then told me to take the cup and fill it. I had a little trouble starting, with her standing in front of me, looking intently at my dick, hands on hips, obviously impatient. Finally, with mission accomplished, Mistress locked me back in the belt. She then told me to finish dressing. This I did as quickly as possible. Next she put on a nitrile glove. She led me by the wrist back to the desk. As I put the cup on the table behind the desk, Mistress told the tech that I couldn't pee unless she held my little dick for me. She then made a show of removing the glove and dropping it in a waste basket. When it was my turn for blood to be drawn, Mistress stood next to me, holding my hand. She told the tech that needles scare me and she had to hold my hand or I would start crying. Once outside she told me she should be angry with me for interrupting her morning, but she had had too much fun.

 

In spite of what she said the other day, I could tell that Mistress was annoyed that I had to call her to come to my rescue. She was in a snappish mood that afternoon and evening. I felt like a storm was coming and I had no shelter. She had made a decision this morning, ordering me to stand in front of her. She unlocked my belt and set it down next to me. Then she lubed a stainless steel segment ring and told me to put it in my P.A. hole. I did this. On the ring she slipped on one end of a chain made of 2 more identical rings, at the end of which was a stainless steel disk. The disk had (my nickname), In Chastity. 01-01-09, Slave, Owned by (Mistress' name). The other side had a quote in Latin, which translated as " Someday this pain will be useful." This disk was also inspired by Story of O. The character had a similar chain and disk attached to her pussy lips (inner and outer. Mistress used the reverse pliers to set the segment into the open area of the ring, completing the ring, and sealing the ring to my penis. Now a simple key would not free me. She said this would keep me from bothering her with dumb things which could have been avoided, like remembering I needed to give a urine sample. When I asked how long I would be wearing the disk, Mistress said I would have plenty of time to get used to it. She reminded me that in the book, the chain was permanently installed. So, when I go out I'm wearing boxers (need the loose fit so the chain doesn't snag and pull. She told me to call Robert and tell him why I am no longer wearing the belt. This keeps getting better.

 

I have now been wearing the chain with ownership disk for most of the day. Whenever I walk the chain moves , causing me to get semi aroused, or at the very least aware of the chain. Having gotten permission from Mistress, I tried to masturbate. I know better than not to ask. So, under her amused expression, between the weight and rattling of the chain as I stroked, the tension of trying to cum, and the result of long term denial, there was no danger of my having an unsanctio
ned orgasm. I had been through this before, so I wasn't surprised. Robert's reaction to my emergency call to Mistress was to call me a dumbass. A dumbass for not calling him instead of Mistress.
Attached are 3 drawings I found that seem to sum up my life lately.

 

This morning Mistress told me she was going to give me a choice about my chastity. This struck me as not good. She said I could either carry on as usual, give all key holding power to Robert for a trial month, or, she said, I could take what's behind Door number 3. This was a minefield. The third choice was very dangerous, It could involve just about anything. So no, not that one. My mind was racing, looking for the more subtle trap. I knew Mistress was annoyed with me right now, and might very well enjoy having me choose her, and therefore punishment. Choosing Robert might be safest, but Mistress could take it as my being disloyal. What to do? I finally settled on Robert. When asked why, I told Mistress it was to give her a kh vacation. I asked her what was behind Door number 3. She held up a card "Pegging by Callie." Mistress said it was a good thing I didn't pick that. Then, in a game show host voice, Mistress said, "Come on down!" Robert came out of the kitchen. Mistress courtseied and made a show of handing him the reverse pliers. She said if I have any chastity problems, I have to call Robert. Next I was told to dress and go with Robert. Here at his house, Robert put the pliers in a box, which he locked with a combination padlock. He took out his tablet and showed me that he had opened an account on an automatic kh site. He told me the pliers would be unavailable until the program allowed it. He said he had a friend set the combination according to the program and not share it with him, so he couldn't open the box if he wanted to. He said the friend had no doubt forgotten the combination by now, which was double security. An emergency unlocking, which can be purchased for a small sum from the site, would also cost me a penaly of his choosing. First chance to unlock, and he emphasized that it was only a chance, was 12 hours away, that is, midnight tonight. He stressed that I should not assume that I could expect an orgasm to accompany an unlocking. Mistress might change her mind about lock up on a whim, but Robert was taking no chances on taking pity on me. He put the box on his bedside table. He said it would give me something to think about. He said that had I chosen to stay with Mistress, I would have had PIV in my immediate future. Maybe. There was that twist of the knife that was no doubt Mistress' idea. Robert said I should show a little gratitude to him. I got on my knees but he stopped me and said I should undress first. That was only the preliminary. During the "main event", with every thrust my chain would swing, adding to my feeling of being used. It was also very erotic. Later we sat next to each other on the couch, listening to music, with Robert absently playing with my chain. He told me in an offhanded way that I would be staying with him through the weekend. Mistress had already packed some clothes, which he had put away. It seems I am easy to read. Robert asked me if I wanted to stay up to midnight so he could open his present. Yes, Daddy. I'd like that.

 

Well, the program worked, providing the combination to the lock. As it was just a trial run, Robert tested the combination on the box, and once satisfied, told me to face the wall while he reset the combination from the computer screen. He told me that now we'd get serious, as he had set the timer for ten days, with the chance to unlock once every 24 hours. He said that the program had the option of choosing a key holder bot to add realistic randomness. He could also set the lock for a specific amount of time, without any chance of early unlocking. That will be next. Now I knew that barring luck in getting an early unlocking, my P.A. and property disk was fastened to me for at least another ten days. I would have to get used to this method of chastity. Mistress is caprecious, while this automated key holding lacks the human touch. It is a sort of chastity prison with a robot warden, with no possibility of reprieve, except the scheduled "pick a card, find the early release." At least Mistress brought a degree of the unexpected. I will have to adjust to my new status quo.
This morning Robert handed me a honey do list, cleaning, washing, shopping. It is obvious that my time with my unofficial husband is not going to be a vacation. A wife's work is never done.
My chores are mostly finished. I mentioned to Robert that the PA ring was pinching occasionally inside my penis. Being sympathetic, he said that if I lucked into an early release he would replace it with my 2 1/2" Jailbird. Since Mistress had come up with the idea of locking it on with a ring with the reverse pliers, that's how he would lock me in. He went on to observe that the cage was small enough to restrict erections, and prevented masturbation. In addition, he noted that the design meant that I could clean it while showering, so there was no good reason, under normal circumstances, to ever remove it. Whoops! That took a sharp, unfortunate turn. We then went back to my house and gathered the cage and ring that we had discussed as well as the leather support belt. Robert arranged ahead of time for Mistress not to be there while we performed our errand, to keep her out of the chastity loop.
I lucked out last night, picking out the "unlock" card, and had my dick locked in the Jailbird before 1 a.m. Robert replaced the pliers in the lockbox and reset the lock. He told me that from now on it was going to be more difficult to get an early unlock.
It is a relief not to have the sharp pinches from the chain. Robert said, "I have to take care of my little girl." I replied, "Thank you, Daddy." I am amazed sometimes at how natural being submissive has become for me.
So far, I've been locked for about 16 hours in the Jailbird. The only thing is that I'm so aware of it, after having been locked away in the belt, that my hand keeps going to it, holding it. Initally, Robert said "Go ahead, all you'll feel is steel." After a while he said that if I keep touching the cage, he'll put 2 tube socks on each hand and duct tape them to my wrists. He definitely has a different style of managing my chastity. I will try to keep hands off.

 

Robert reset the program so I won't unlock early. So I'm getting into being locked in the Jailbird.
Robert told me it was agreed that I will stay with him for the rest of the month. I just said, "yes sir", knowing the situation was out of my control. There is a block of time set aside where Mistress will make a point of being absent, so that I can wash her dishes unobserved, what Robert calls Invisible maid service. The rest of the workday I am his maid, which keeps me occupied. My chores include washing his car as well as housework.
Robert said he wanted me to feel more feminine, the way Mistress wants, so he gave me a pair of thong slippers with a 2 1/2 " wedge heel. He said it would give me a feel for wearing heels, sort of a starter set. He showed me a video on how to walk in heels, so I wouldn't injure myself. I find myself walking slower and more conscious of how I walk. Suddenly I am very careful on stairs. Robert teasingly urges me to sway my hips when I walk.

 

When it isn't pouring rain, Robert and I walk around his neighborhood, with me wearing the thong slippers, walking slower than I normally do to compensate for the raised heels. Robert has told me what else I wear is my choice, with the exception of my cage. Today, to please him, I chose gym shorts and a polo shirt. And, of course, panties. Robert vetoed my wearing the fanny pack, or any other way for me to carry my wallet, keys, etc. He said he would carry my i.d. and would pay for anything on our walk. In short, I was totally dependent on him. My outfit was hardly manly, which earned me a few looks, not exactly hostile, not exactly friendly. Obeying Robert, we held hands. He bought a feminine straw hat for me to wear. We had lunch in a diner, where Robert positioned me to "show off" my legs and footwear. I was instructed to sit with my legs crossed, "like a lady." Robert seemed to be enjoying our outing, while I was self conscious, feeling everyone who passed by was judging me.

 

Earlier today I made the unlock time and Robert took off my chastity. He had me take a shower, dress, and come back to him. Something was up, but I couldn't figure out what. When I returned, Robert took me home. Mistress then told me she had spoken to Robert and they agreed to make some changes in my life. She said that my becoming a softer, more feminine version of myself should be something not just for play but something serious that I will live with. They don't want me to try to live as a woman, but to have a balance of the masculine and feminine within me. They want me to embrace a certain androgeny in how I dress, act, and most importantly, think. Mistress said that as I am already using the name Carly as a sign of my "softening", she had decided that from now on I will answer to "Miss Carly", to put me in a permanent femininizing head space, to counteract a lifetime of male propaganda. She had said that she wants me to embrace my being sexually fluid, and not to think of myself as "man", "manly", hetrosexual, homosexual, or bisexual, as these were too restrictive for who I am becoming. Robert told me that my pronouns are now: "she/her", as a constant reminder of my feminine aspect. Then Mistress showed me that yesterday she had registered me as, "Miss Carly" her slave, as a further reenforcement. She is listed as my owner, Mistress Lilith, on the registration. It is a name she has never used outside of our little circle, or let me use in my journal, which showed me she is serious. I understand that as her slave, I had no say in any of this. To celebrate my new status, my new name, Robert, with Mistress' help, put me in the Cherry Keeper Micro, to remove my dick from sight. Mistress said she prefers me with my "little dick" tucked away. Mistress then told me that to make things simpler for me, she is my owner as well as my wife. Robert is my husband, to be obeyed, but it is Mistress who owns me. I am their wife. Robert then took me into our bedroom for us to make love. When we were finished I discovered that Mistress had moved my clothes into the room as well as a good assortment of Robert's. There is no mistaking that this is now our room. Robert is no longer a guest with benefits, but my husband, who does not have to be invited to stay overnight. We have exchanged keys. It is my job to serve them, to obey without question. Mistress informed me that I will only sleep with her when told to. I sit here, back at Robert's, absorbing this day's events. I will stay here with Robert until the end of the month, as I have been told to. Wearing the CK Micro, I can touch my balls but my penis is pushed inside me, making me feel that I am no longer a man, just as Mistress Lilith and Robert want. I take comfort that my sexual denial serves them. I must embrace the fact that I am Miss Carly now, and must begin to think as her, to automatically answer to my new name. In short, to find out who she is and become her. I have attached the Slave Registry document as well as photos of me in one of the skirts I now wear when I am home, showing some leg, as Robert said, and my cock, freshly shaved, peeking shyly out from the Micro, and a gloved hand reminding me who my balls belong to. I have been told I have to memorize that I am also 21-434-672-571.

 

Thanks for the encouragement. My life has taken a quite a few twists and turns I could never have imagined. It helps to write down my thoughts on what is happening with me, and knowing that someone gets something out of reading this is a comfort. I try not to worry if I come off as foolish or naive. I'm just trying to make sense of my life.

 

I suppose it was inevitable, I've come down with a sudden case of sexual frustration. I have no idea what brought it on. Robert has been very attentive to my bottom, and he is always up for receiving oral from me. And yet I am so horny that I keep reaching down to grab my dicklet only to get nothing but air. It might be locked away in solitary confinement, with parole not looking too good, but that desperate urge came back as though I had the remotest chance of piv with anyone. If I were given the opportunity, thanks to my micro cage, I have no doubt the first thing the woman (or man) who held my attention would say is, "Where is it? Damn Miss Carly, you have no cock, just a worm who's staring at me from behind a round white fence at your ballsack." That would kill the mood. I understand that eunuchs have virtually no sex drive. Right now that doesn't sound like a bad tradeoff. I wonder what it would be like to have no balls, just smooth skin beneath my clitty, and no interest in sex. On second thought, I'd rather keep my balls. Testosterone can make a guy crazy. Maybe this is part of what Mistress calls male hormonal poisoning. I think I have to interrupt Robert from his computer game to perform his husbandly duties. I'm certainly ready to perform my wifely ones.

 

Thanks. I feel like I've fìnally found the real me, now the discovery begins.

 

Today, that is, Tuesday, Robert and I went to a coffee place, and when the girl behind the counter asked for our names for the order, Robert gave his and then pointedly told me to give mine. I have to admit that I was embarrassed when I said, "Miss Carly". Robert smiled and said that wasn't so bad. No, but when the cashier called out my name nice and loud, I did cringe a bit as I walked to the counter. I felt all eyes on me, like being back in school and being called to the blackboard in front of the class, with a boner you can't conceal.. When I returned to the table, Robert kissed me on the lips, possibly as encouragement, possibly to make me uncomfortable. With Robert it could have been both. This is not as easy as I thought it would be.

 

Back home with Mistress Lilith, after a month as Robert's live in wife and maid. I have certainly brushed up on my cleaning skills, and worked on others. Mistress welcomed me back with a slow, loving pegging followed by my going down on her. We then spent the evening cuddling. I also gave her a massage. We then showered (seperately) and Mistress told me I'd be sleeping in my room, as Silver was due soon and staying overnight. When he arrived Mistress told me to show him my clitty. I raised my skirt and showed him my lack of a penis. He bent down and casuallly pulled aside my sack skin with his thumbs, exposing my cage and behind that, the lips of my penis.
"Here's her little clitty", he said, not acknowledging me, as though I was just an object. Humiliating. At Mistress' suggestion he pulled out his penis, which was already huge without being fully hard. More humiliating. Mistress looked back and forth between us and said, "Now i see a cock. Now I don't. Now I see a cock. Now I don't." Even more humiliating. She laughed and waved me away, dismissing the peasant. Alone in my bed, my thoughts were that I am determined to make Mistress proud of me, to surprise her with something that will show I am fully committed to improving myself, transforming into Miss Carly, like a butterfly coming out of it's chrysalis as something new and pleasing, in short, less male. I have to be careful to be subdued in my femininity. I will have to go shopping and hope for inspiration. Having worn the heeled thong slippers almost constantly for the past 12 days, I feel frustrated that I'm not yet fully confident walking in them. Perhaps part of the problem is the heel does not immediately lift up as they would if held in place by a strap. I wonder if the change Mistress wants constitutes my becoming a sissy. Not sure how that is defined. Funny how now that my clitty (Mistress' term) is hidden away inside me, I have become very conscious of my balls, careful not to squeeze them when I sit down or bend over. Later, Mistress walked naked into my bedroom to tell me it was time for my shower, and ordered me to wear nitrile gloves, so I couldn't directly touch even the tip of my clitty (The only part of it now semi-exposed behind the cage. She then showed me where she put a full box of the gloves, implying I might never touch it again without permission. Mistress saw the look on my face and said I had no reason to touch it. She said that it was her property, to use if and when she pleases, and now that she has Silver, she has one less reason to let me out. I guess she wants me to stop thinking of myself as having a penis, to stop thinking of myself as male. I have only as much free will as Mistress allows.
Attached are pictures of my softer wardrobe thus far, all woman's tops.

 

Here's something I came across which surprised me. It's a comic about gender transformation, and the principal character has my name. Could this be a warning from the fates?

 

Was just told I did such a good I'm going to be doing more housekeeping for Robert and her sister too. Oh joy

 

This afternoon, Mistress took me out of the micro cage and had me shower. She then inspected my clitty and, satisfied that the compression marks on the head were starting to fade, locked me back up. This was unexpected. Mistress handed me a heavy duty plastic orange box and two luggage combination locks, a gift from Robert. She handed me my cage key, and the emergency key. Knowing where this was going, I put the keys in the box, and snapped the locks shut, sealing it. Mistress spun the dials. She told me that she had used the same program that Robert had used last month. I am now locked without parole for 2 weeks, and then unlocked only for a full cleaning, then locked for another 2 weeks until the program gives Mistress the combination, which she has assured me she has forgotten. She could buy the combination to unlock me, but there would be a nominal fee for that, as well as a punishment for me. She would let her sister Callie determine what that would be. Whatever Callie decided, Mistress emphasized, I would "suffer." As a safety measure she has given the combination to the locks to her sister, in case of emergency. She knows that her sister will not give me the combination unless it is an emergency. If it wasn't for hygene concerns, I would not be let out short of armegeddon. Mistress handed me the box and told me to put it on my bedside table in my room, to make sure I saw it first thing in the morning and last thing before going to sleep. She had definitely been coached in computer keyholding by Robert. For some reason, I felt my heart drop when the shackles snapped shut. It was a new level of being locked because even Mistress didn't have immediate access to the key.

 

Mistress told me that Miss Carly needs a black dress like a real woman.. Then she presented me with one. As soon as I put it on I immediately felt more feminine. I love it.

 

Just a quick post to show a couple of photos of the Mary Janes that Mistress gave to me, paired with the black dress. The little socks haven't arrived yet. It can't really be seen, but the dress is raised in the back so my bare ass is on the chair. This is how Mistress wants me to sit, taken from Story of O. I hope it is not a signal of the direction we are headed.

 

Mistress sent me this photo, with a note "This reminds me of you in your micro cage: all balls and a dick that could get lost in a thimble.
Well I certainly feel less masculine after that.

 

My kh bot gave me a chance to unlock early. Mistress took the opportunity to inspect my clitty. She said she didn't like the compression marks and the white patches looked like it didn't have full circulation. So I am now wearing just my p.a. ring, "to let it breathe", which I find frustrating. Mistress said I shouldn't worry, my clitty is far from masculine. I miss, almost need, having my clitty locked up. I think it's become like a security blanket. My not being locked up is almost a punishment. Odd what we can get used to.
Wardrobe update:
Monday I received a softball shirt in the mail, white with pink sleeves and a skirt with slit sides, as sleepwear. The shirt was a woman's item, while the skirt was a man's. Both were ordered by Mistress. It seems she is working towards my having an equally feminine wardrobe.
Tuesday I received a pink smock/apron, and a pair of boots with a 2 1/2" heel. Cute and surprisingly comfortable.
I look forward to whatever comes next.
At Robert's request, Mistress took my picture posed the way he said he always thinks of me, to be posted. I think he's enjoying making me squirm.0

 

Wednesday afternoon, Mistress took out my p.a. ring and put me in the small House of Denial pink cage. She told me to go into her bedroom and get dressed. On her bed I found the outfit you see below, neatly laid out for me. I took off my skirt and slowly dressed, enjoying the erotic strangeness of it. When I rejoined Mistress, she said I needed something to complete my ensemble. That's when she put around my neck the leather choker with "SLUT" on it. Pictures were taken, and then I was set to work dusting, washing dishes, and mopping the floor. Mistress also gave me instructions for later. After a while the doorbell rang. I opened the door, feeling nervous because of how I was dressed. As expected, it was Silver, Mistress' lover. I curtseyed, and greeted him. Once inside, I offered him a drink. I poured him his scotch and asked him to make himself at home in the living room while I went into Mistress' bedroom and announced his arrival. Mistress led the way to the living room, where I fixed her a drink and retreated to the kitchen to dry the dishes. When I was finished, Mistress called me over to where they were seated and in a commanding voice, ordered me to lift my skirt. She pulled down my tights and pointed out my new cage. I felt myself trying to grow, while the cage did it's job. Mistress then instructed me to turn around and bend over. I felt my skirt lifted and then a wet finger inserted in my anus. I took a deep breath and made an effort to relax as the finger slid inside me, paused, and slowly began moving. Soon, it was removed and my ass was patted. Mistress told me I wouldn't be needed for the rest of the evening. I pulled up my tights, curtseyed, thanked Mistress and went to my room. So I sat on my bed, thinking about how easily I fell into the role of sexually available servant. Perhaps that's why Mistress had me wear the "SLUT" choker. She seems to know me better than I know myself. While wearing the maid's costume in front of Silver and being treated that way was humiliating, in a way wearing it also made my total submission, without ego, easier.
P.S. When I first put the uniform on, Mistress remarked that it was a tight fit, and would have to be replaced soon.

 

Mistress gifted me with a new maid's uniform, (black dress instead of the previous pink) which is a much better fit. Photos were promptly taken. She told me I have to wear it, along with my boots when Silver, Robert, or Callie come over, greet them with a curtsey, and wait on them like the perfect maid. Evenings at home, on alternate days, I wear a skirt and a blouse, and the mary janes. Mistress is definitely stepping things up. Mistress told me the same dress code applies when I stay at Robert's. When going outside I am allowed to choose what I wear. If we're expecting guests other than Robert, Callie, or Silver, I have permission to dress in boy clothes so as not to impose how we live on others. When I casually mentioned that I need a haircut, Mistress said "Not without my permission." Another reminder of how complete her control of my life is.

 

Just checked my journal. Last O was July 4. Mistress told me not to bother checking the calender, she has no plan to grant me another release anytime soon. No real surprise there. This evening, Silver and Callie came over for dinner, so I was serving in full uniform for the evening, feeling submissive, humbled and foolish. When not serving, I stood behind Mistress' chair, at the ready. When dinner was over, I cleaned away the dishes, and served drinks, then went to the kitchen to eat. Later, Mistress, being the gracious hostess, had me get on hands and knees for Callie to peg while Silver watched with a slight smile. When Callie was finished Mistress instructed me to pull up my panties and satisfy Silver orally, remarking that I could not take him in my ass. Yet. When Silver finished, I thanked Mistress as I curtseyed, and went to the kitchen to wash the dishes. After a while Callie said her good byes and left. Not too long after that Mistress took Silver to her bedroom for the night. I am in my bedroom, wearing only my pink cage, unable to sleep, picturing Mistress having sex with Silver.