Our Next Journey

Mistress Alegria says:

littlechasteguy approached Me last year at the end of 2009. Here We are in May of 2010 and much has happened to him in such a short time. You all.......Well........most of you (lol) have read from the beginning what I thought about chastity submissives/slaves. And you also know what has transpired over these many months, if you have read our blog.

I now enjoy keeping some, if not all, male submissives/slaves in chastity. The training of littlechasteguy and his ongoing training only strengthens My resolve to help many who seek this way of life; to totally understand and weigh in on it's benefits, whether they be short or long term. I understood that it also would open up many aspects of his mind and give him the freedom to explore the next rung on his submissive ladder.

Hence the birth of "koko", full name "koko demure". I am now in the process of training koko demure still in the realm of chastity, which she/he chose for her/him self. But the main focus of her/his training will be based upon the total feminization of her physical being/persona. To reflect this change her new blog now exists to chronicle this new journey. I, from time to time, will comment on the goings on of the infamous koko demure in her blog.

I will also be writing in My own new blog "Life in The Rubee Rooms", where you will find out what is happening in My busy life. It will also contain updates on the training of My koko as well as photos of Our adventures and everyday lives, together as Mistress and submissive; but also separately.

This blog will remain up for those who wish to gather information pertaining to chastity.

Safe Journey,

Mistress Alegria

A New Me!!!!!!

koko says:

I am excited and pleased to announce that it is time to end this blog. for under the wise and expert tutelage of Mistress Alegria littlechasteguy has evolved.

Back in December of 2009 I approached Mistress Alegria petitioning Her to be my Mistress and Keyholder. After several discussions and after agreeing to a contract defining expectations and responsibilities of both, She agreed. Over the following months both Mistress Alegria and me became aware that there was another completely different person lurking beneath my surface.

From some early experimentation with feminization, as documented in earlier posts, we found a natural female persona just waiting to be brought out. And Mistress Alegria is just the type of person to delve beneath the surface and bring out the underlying personality. We became acutely aware that I had much more going on besides enforced chastity, and that I should not be defined in such a manner.

And so koko demure was born. I invite you to check out my new blog at kokodemure.blogspot.com to learn more about my explorations and continuing evolution under the firm and wise direction and guidance of Mistress Alegria.

And of course to learn more about Mistress Alegria I invite you to peruse her Rubee Rooms website and her new blog Life in The Rubee Rooms.

I want to thank al the readers of this blog, especially those that signed up as followers and those tha commented and provided suggestions. I hope you will continue to follow us on our journey. I don't know exactly where we will end up, but I am pretty sure it will be adventurous and entertaining.

Ready?

littlechasteguy says:

Mistress Alegria has told me of her desire to see me suck cock, as a demonstration of Her power and control over me. As a heretofore completely heterosexual man there is naturally a little fear. Will I be able to bring myself to do it? Will I gag and be no good? Will I enjoy it so much that I become a cock loving slut? All are to some extent fears of mine.

But, as usual, Mistress Alegria has been bringing me along slowly, probing my mental state and pushing me into new experiences slowly.

First were several discussions, where I said that yes I would suck cock to make Her happy. She also noted with interest that on my FetLife account I listed myself as heteroflexible, indicating a willingness to try. And in our contract one of the provisions is that I will perform any sexual tasks (as long as safe) She directs. So there is no way for me to avoid sucking cock if She so desires.

And recent events lead me to believe the time is near. Mistress Alegria has mentioned to me several possible scenarios where I, while still locked in chastity myself, would be sucking off bigger and better cocks than the one attached to me. And Her probing has recently gone to a new level.

Last weekend, at a public venue, Mistress Alegria was engaged in some rough play with a bottom friend. My job was to help Her; organizing and handing Her toys, cleaning up, providing refreshments, and otherwise serving. As the session progressed, prior to entering his ass with Her strapon, Mistress Alegria had me get on my knees and suck on it. It did feel good and natural to do exactly as She ordered, without hesitation. I loved the smile on Her face as I knelt before Her and sucked on Her tool. I'm sure I was as swollen in my cage with desire and lust, wanting only to please my Mistress, as I am now while replaying this scene in my mind and writing about it.

After giving her bottom a good pounding and beating Mistress Alegria opted for a special treat for him (and me). She had me don a latex glove, apply some lube, and stroke his hot, hard cock. For the first time in my life I was engaged in a sexual act with another man, and in a public setting! All the while I was transfixed  the glow emanating from my beautiful Mistress. Obviously she was enjoying the scene as much as I was, probably more. Again I swelled in my cage, breathing rapidly with excitement. Unfortunately our friends balls were so battered at the hands and feet of Mistress Alegria that he was unable to cum, eventually asking for me to stop. So I did not get to experience the feeling of hot cum spraying on my chest and belly. Maybe next time.

After I stopped stroking Mistress Alegria had me give the tip of his hard cock a kiss, which I again did without reservation.

So for the first time, and at a public venue no less, Mistress Alegria had me stroke and kiss another man's cock. Later that evening She told me that She was testing me to see how I'd respond, making sure I did not freak out. And I made her proud by passing the test.

So I am sure that in very short order She will have me sucking cock. My fear that I'd be unable has been somewhat alleviated. I may end up not being a good cocksucker, but I look forward to the opportunity to please my Mistress in this manner. Who knows - I might get so excited I cum in my cage, something sure to amuse Mistress Alegria. Or maybe I will become a cock loving slut, begging Mistress Alegria for more cocks to suck.

Anyway, it is sure to be an adventure. And I am certainly helplessly swollen in my cage as I ponder the future.

Progress?

Mistress Alegria says:

It has been several weeks since My cock, which is of course attached to the body of littlechasteguy, got it's Prince Albert piercing. The healing process has not been as bad as expected. He has taken very good care in maintaining the upkeep and cleaning.

Of course prior to unlocking My cock for the piercing and healing, the idea of My cock finding itself free, and the temptation of getting his hands around it, quickly came to mind. But this thought instantly retreated as littlechasteguy promised Me that he would be a good boy and not touch My property in any unauthorized manner.

To those I know sitting there reading this and thinking, "Sure!", "It's out and free!", "He has a history of masturbating!", "There's no way he won't touch that cock!", "She'll never know!" - Again, he gave his word to Me. And to littlechasteguy his word carries a lot of weight. I know that no matter how tough it was to wake up in the morning with an erection, and to clean it while in the shower with a nice batch of warm, soapy suds....he would never jerk off.

His training continues, both in private and at various public BDSM events. It is ongoing 24/7. So while My cock was free from it's chastity device I took every opportunity to make sure he was always aware of lovely women with wet pussies. LOL. It is part of the rewiring of his thought processes - A mental tease and denial.

Whether sitting at a red light, strolling through a mall, or anywhere else, I comment on the lovely ladies in their short skirts and spring dresses, and how it would be wonderful to see him on his knees with their legs wrapped around his head. His reaction never gets old. I thoroughly enjoy his rapid breathing and fixed stares, like a beagle on a hunt! And the slow rise of My cock. You can clearly watch on his face as the struggle takes place. The body responds at one with the mind. And the mind wins, with the cock becoming it's itty bitty self again.

Yes, the progress is evident in his reactions to the situations I place him in. However, his training continues, as there is still much to be accomplished.

And I am enjoying every minute of it.

Prince Albert Update

littlechasteguy says

I would like to thank all those who've wished me well and congratulated me regarding my new Prince Albert piercing. It is healing very well. At this point this very little discomfort (only when pushed or pulled in certain directions). And I can report that "Her" little cock is sufficiently healed to once again be locked in chastity.

We opted to return to the CB-6000S while the healing continues, as the opening at the tip is large enough and placed in such a location as to allow the ring to protrude comfortable out when "Her" little cock swells inside the cage. As "Her" little cock is still a little tender we felt that the anti-pullout mechanism of the Phoenix Sapphire would be problematic regarding insertion and withdrawal for inspection and cleaning. The stiffness of the CB-6000S's cage provides more protection than that of the Mini-birdlocked, which will be the chastity device of choice when fully healed in a couple of weeks, when the Prince Albert can be used to provide the level of security Mistress Alegria and I desire.

This has been a very good experience for me.While healing and free from physically enforced chastity it has become apparent that my training to date has shown benefits. Progress has been made.

Prior to being locked in chastity I was a compulsive masturbator - at least once a day, and frequently more than once. This bad habit definitely negatively affected my relationships, sometimes leaving me unable to perform as my partner desired. The desire to break this habit, along with the knowledge that "Her" little cock is too small to generate pleasure, was the reason for my acquiescence into enforced chastity.

Prior to my piercing, knowing that "Her" little penis would be free for and extended period for the first time in many months, I was worried that the temptation to masturbate would be overwhelming. However, I am pleased to report that this has not been the case. I've been a very good boy, not playing with myself at all.

Initially fear of pain and bleeding contributed to my behaving. I was worried that such activity would be painful, irritating the piercing and causing it to bleed. But I quickly discovered through observing involuntary erections and when Mistress Alegria examined Her possessions, causing involuntary erections, that erections actually made the piercing more comfortable as the skin expanded causing the piercing to open up further, allowing more clearance for the jewelry.

So why have I not been frantically jerking off while free? It is because I truly do want to be a good boy for Mistress Alegria. As I have given Her complete ownership of my former penis my only responsibility is to keep it clean, healthy, and ready to be used for Her amusement when She desires. I understand to my core that I am not authorized to play with Her belongings without permission. Being good for so long (a total of 11 days free before being caged back up) makes me proud. It shows that the wonderful training bestowed upon me by Mistress Alegria has been effective regarding reducing my selfish need for orgasmic pleasure.

Despite the progress to date I know I remain week and that much remains to be done in regards to my training. As with an alcoholic or drug addict, who cannot control themselves after that first drink or drug, I suspect that should I  give in to my deep-seated desires and just have one masturbation I would be off to the races. I do not want to return to those days. Nor do I want to face the wrath of Mistress Alegria when She catches me. Or have Her be disappointed in me. I love it when She is proud of me.

So while progress is evident, much remains. My anal training continues, preparing me to derive all pleasure by being penetrated of the joy of others. I also know that lurking just below the surface is that same selfish, little man that petitioned Mistress Alegria for help. I do not want him to re-emerge.

Therefore I am happy to back in my chastity cage. Life is so much simpler and pleasurable for me. I do not have to fear  a weakening of my resolve to be a good boy regarding my sexual behavior. I can relax knowing that Mistress Alegria is in control.

Prince Albert Piercing

littlechasteguy says:


Over the past several years I’ve tried many different chastity devices. They include the CB-2000, CB-3000, CB-6000S, Mini-Birdlocked and the Phoenix Sapphire. Of these the Mini-Birdlocked is by far the most comfortable to wear when engaged in an active spring and summer lifestyle, activities such as riding my bicycle. However, the Mini-Birdlocked, at least for me, is far too insecure. It is simply too easy to pull out of, and I was unable to locate any devices or modifications to make it more secure. So it got put away. (Actually it is on display as part of Mistress Alegria’s chastity device display.)

However, with spring having arrived and summer rapidly approaching, I began to think about being comfortably active, and my thoughts of the Mini-Birdlocked returned. Then, several weeks ago, Mistress Alegria and I attended the semi-annual sale at a local event. Looking at the list of vendors prior to going I saw that a tattoo artist and piercer was one of the listed vendors. The thought of a Prince Albert piercing popped into my head. I mentioned it to Mistress Alegria, and unsurprisingly She was quite enthusiastically supportive of the idea. So we made a point of visiting the booth and discussing possibilities while at the sale.

Deus of Exposed Temptations Tattoo and Body Piercing seemed quite knowledgeable and professional. One of my concerns when initially considering a piercing was that I pass through metal detectors regularly at work. I would like to remain discreet. Deus suggested titanium jewelry, as it is not magnetic, thus not readily detectable by magnetic metal detectors. We were also quoted a reasonable price. Mistress Alegria and I told him we would be back in touch.

Over the next couple of days Mistress Alegria and I discussed the advantages of a Prince Albert piercing, along with possible difficulties. We agreed that the increased security would allow me to be more comfortable in my chastity device, particularly since I enjoy being very active when the weather is nice. The possible difficulties include the risk of infection, and the pain (I am not a pain slut by any means). We agreed that the risk of infection was minimal, as I am quite fastidious and attentive to detail. And the actual piercing would be quick, so the pain relatively minimal, and since I generally heal pretty quickly any pain afterwards would not last long. On balance it seemed the benefits outweighed the down side. So I made an appointment.

I’ve never been pierced, tattooed, nor had any other marking intentionally placed on my body. I do have a few scars, but none intentional. Thus as the appointment approached I began getting a little nervous. (Have I mentioned that I am not a pain slut at all?) But I knew that Mistress Alegria would be with me to provide strength and support, so the fear never became overwhelming and I never considered backing out.

Then came the fateful day. We left Baltimore MD around mid-morning and drove to Manassas VA. We had my last meal as a whole man at Wendy’s, and Mistress Alegria again asked if I was ready, not that there was any choice at that point. We arrived at the parlor and after taking care of some paperwork (there’s always paperwork, eh?) we were taken back to the operating room. Mistress Alegria had the camera of course hoping to be able to take pictures as I thrashed about, blood everywhere.

But alas, that was not to be. It was actually pretty quick and anticlimactic. After I lowered my pants and underwear Mistress Alegria cut off the plastic lock securing my chastity cage (Phoenix Sapphire) and the cage was removed. Up on the table I went looking at Mistress Alegria so I would not have to observe as I was mutilated. Deus cleaned me up a bit and placed a tube down my urethra, which did sting just a little bit. Then there was a quick, sharp sting, and the deed was done. I’ve had bee stings that hurt more (although I’ve never been stung on my penis). There was barely any blood and I did not thrash about in extreme pain. I tensed up for a second or two, and then relaxed, as it was over. Mistress Alegria did get a few nice photo’s though.

After it was done we all chatted a bit and we were soon on our way back home. While driving home Mistress Alegria told me she was proud of how well I handled it all (I think She is aware that I am not a pain slut), making me very happy. Then came the next big hurdle, when it was time to pee the first time at a pit stop on the way home. I expected it to be quite painful, but again it was anticlimactic. The buildup and anticipation of pair was totally unfounded. There was absolutely no pain at all. It was actually kind of unbelievable.

Arriving home we removed the bandages and cleaned things up a bit. There was a little dried blood, but not nearly what I expected. Again a few pictures were taken, which are posted along with those taken during the piercing. Not long after arriving home I experienced my first erection as Mistress was examining Her property for any damage. Again no pain and no blood.

So overall, at least for me, the installation and the first few hours afterward were no big deal. I think every man should be so pierced. We will allow it to heal for the next week or so, cleaning it as suggested ensuring against infection. Then back in chastity I guess. It should take about 4 weeks to heal completely, at which point the Prince Albert can be used to securely lock me in chastity and allow Mistress Alegria to use it for other nefarious reasons. And for some unexplainable reason that makes me happy.

His Training Continues

I was approached while out at an event with My littlechasteguy by a couple, He Dom, her His submissive. I have known them for some time as friends in and out of the BDSM community. He wanted Me to help with a special scene that He had in mind for her. We exchanged ideas several times via phone and emails before the final scene was to take place.

As We discussed the scene I instantly thought that this might be an opportunity for yet another agonizing and learning experience for My littlechasteguy, as his training is ongoing. Even though held steadfastly in his chastity device, his mind still holds fast to his ever present sexual desires. I know that at times his service is still MOTIVATED by his desire for release. His pathetic face while I tease his tiny cock held within the Phoenix Sapphire speaks for itself.

The night finally arrived for the Dom and His submissive to visit. She was blindfolded and led naked under a raincoat to My Rubee Rooms. The night consisted of her Dom and Myself taking turns leading her up and down the emotional and physical ladder between pleasure and pain.

Littlechasteguy sat nearby watching, his body poised to take direction from Me at any moment. The female submissive was a lovely pale vision across My specially modified bondage horse. Her soft moans and replies to the questions she was asked by her Dom were a mixture of tears and erotic, deeply seated sighs.

For that night littlechasteguy was allowed to be out of his chastity. His only purpose was to be an object for the female submissive’s desire. His unworthy penis, due to its small size, was of no use to her. He wore a large strapon device to allow her to enjoy the pleasure she was rewarded with by her Dom.

Even before the strapon harness was placed on him littlechasteguy’s little dick started to rise, only to be slapped down hard by Me. This was followed by some necessarily strict language on my part in order to discipline him. He was instructed to orally prepare her for the strapon.

Satisfied that she was ready I stood behind him and instructed his every move at first by guiding his hips and whispering in his ear. With Myself and her Dom both happy with littlechasteguy’s movements and rhythm, I stepped back. The sounds of both littlechasteguy’s and her moans filled the room.

Littlechasteguy several times moaned loudly and pitifully that he was about to cum. Each time I reminded him of the consequences if he did. Her Dom and I watched and enjoyed what was taking place in front of Us, as soon she and littlechasteguy forgot that we were in the room. Soon nothing was heard but the loud slapping of her wet pussy hungrily being fucked by a small man with a large strapon. The sight was exciting, yet very sad to watch. POOR LITTLECHASTEGUY AND HIS TINY COCK. She was allowed to cum several times with the permission of her Dom as a reward for her excellent and unselfish service to Him. And My littlechasteguy was up to the challenge of bringing her to several orgasms, making Me proud. My littlechasteguy was, of course, not allowed to cum.  His service was that of an object to be used, like one uses and discards a sex toy into a drawer when done. His miserable face and shivering body wracked with desire will be ever a great point of laughter for Me, one I get to recall over and over in My mind when I need a quick smile.

Littlechasteguy’s training continues……………