This was the tale of a beautiful, stern and sensuous Mistress and her tiny dicked, collared servant who, at his own request, is kept locked in chastity. And Mistress Alegria was more than happy to oblige.

We have since moved on to the next phase of training and we would love all of you who followed us here to follow along with our new adventures.

The Cock Size has not changed though. It is still tiny!!!!

Tuesday, March 23, 2010

Phoenix Sapphire Follow-up/Long-term Review

littlechasteguy says:

Now that I’ve been wearing the Sapphire for just over a month, it seems it is time for a follow-up to my initial review with some longer term observations. Mistress Alegria has had me wear it 24/7 except for a few brief removals for cleaning and play. The longest it has been off during this period was about 3 hours a few nights ago when Mistress wanted me completely nude for a play session with some friends. But that is another story in itself.

First and foremost, at least for me, the Sapphire is effective. Once properly locked on, using the correct spacers, escape is not possible, at least not without subjecting oneself to severe pain and possible. The repair of the split seam using superglue has held up so far. There have been no more occasions of waking up in the middle of the night with “Her” little penis free. I guess that is a good thing, lol.

During the time worn that has been no significant discomfort. The ring being larger than those I’m accustomed to has resulted in some minor discomfort to my inner thigh on occasion, requiring a little lotion. But as time has gone on that seems to be no longer an issue, as my body has adjusted to it being there. The larger ring does still feel a bit bulky to me, but that too has lessened as time has passed. I suspect that eventually it will seem perfectly normal. And for someone’s first experience with a chastity device, having not experienced other, less bulky devices, I’m sure this would be a non-issue.

For some reason the Sapphire often rotates on my scrotum to near the 90 degree position on my right. I surmise that this has something to do with one testicle hanging lower than the other. This is not a problem, and does not result in discomfort, although at one point I encountered some minor irritation of “Her” scrotum where a sharp point contacted it. However, a few brief minutes with a nail file resolved that completely.

The Sapphire does contain a number of moving parts, and parts subjected to considerable stress due to the design. Breakage remains a concern. Therefore I’d still like to see, as mentioned in my initial review, a distributor of parts a bit closer to me. However, so far none of these parts have broken.

So overall, with the exception of the quality problem that resulted in cage breakage, I would say that the Sapphire is a very effective and good chastity device. Of all the devices I’ve worn (CB-2000, CB-3000, CB-6000s, Mini-Birdlocked, Sapphire) it is the best combination of security, comfort, and concealable under clothing. I would recommend it to others, with the qualifiers already stated.

What’s next you ask? In three weeks Mistress Alegria is taking me to get a titanium Prince Albert piercing. Once it is healed I will likely be wearing the Mini-Birdlocked, at least for the summer. The flexibility of the silicone materials much better for bicycle riding and other such activities I enjoy. And the issue of ease of pullout regarding the Mini-Birdlocked will be resolved by securing the penis to the end of the cage through the piercing.

We will certainly post about that and other ongoing events and my continued training.

Sunday, March 14, 2010

The Luckiest Man on Earth

littlechasteguy says:

I am, without a doubt, the luckiest man on Earth. And the most grateful. My Mistress is just so wonderful. She continually pushes my boundaries, allowing me to experience new activities and live out my wildest fantasies. This weekend has been some of both.

Friday the beautiful and sensuous Mistress Alegria decided to allow me to experience Her sounds. While She was preparing them, ensuring proper sterilization, She also prepared me. She had me lay on her table and then removed my cage. And She warned me that while She was playing I was not allowed to cum, under penalty of extremely severe and brutal punishment. My pathetic pleading and reminding Mistress Alegria that I was so sensitive from not cumming in so long had just the opposite their intended effect. Mistress Alegria obviously took great pleasure from my distress. She loves the psychological aspects of domination.

While Mistress Alegria prepared my body, making sure “Her” tiny penis was fully erect my distress boiled over to the point that I was crying and telling Her that I was ready to accept my punishment. It took all the fortitude I could muster to refrain from cumming. And Mistress Alegria enjoyed herself, as she sternly reminded me of my fate should I give in to mere bodily urges.

At one point Mistress Alegria penetrated my ass with Her finger. I thrashed about and begged Her to stop, as I was on edge and going to cum. Thankfully she withdrew her finger and questioned me regarding this reaction. She remarked that my training to have “Her” ass become my pleasure center in lieu of “Her” tiny and useless penis seemed to be progressing nicely. I loved seeing the smile on Her face as She made this remark regarding Her handiwork. I so much love it when Mistress Alegria is happy. When She smiles I just cannot help but feel that She has the most beautiful smile in all the world. And when I am in any small way at least partly responsible for bringing forth that smile I am so happy.

Then came the sounds. Mistress Alegria has several sets of sounds, of various diameters. Thankfully with me She used the smaller ones. Using an antibiotic lubricant She held “Her” cock steady and slowly penetrated my urethra. I can honestly say I have never felt anything quite like that in my life. The pressure inside me, combined with the tickling sensation inside me, was quite extraordinary. Along with the visual stimulation, as I watched Her gently slide the sounds in and out , it was a tremendous experience.

I must say that prior to experiencing this I was somewhat afraid of being penetrated with sounds. I imagined that it would be painful. However, it was not painful at all, as Mistress Alegria did not use Her bigger sounds on me, at least not during my first time. Also, as the experience unfolded, I was much more fearful of cumming and facing the wrath of Mistress Alegria than I was of the actual penetration with the sounds. This, I am sure, was all part of Her plan. My crafty Mistress had managed to eliminate my fear of being penetrated with sounds, allowing me to relax and enjoy the sensations, rather than being tense with fear as I watched Her penetrate me.

I’m not really sure how long this experience lasted, as I was fairly frantic with lust, compounded by a determination to make Mistress proud and refrain from cumming. Soon enough though, it was over. When Mistress Alegria penetrated me fully with the sound for the final time she marked with Her fingers to indicate how deep She went. I vaguely remember her showing me that She really did use much of the length of the sound, as “Her” little penis is really short.   

After pulling out the sound for the last time Mistress Alegria smiled and patted me on the head, telling me that I had been a good boy. A couple of quick strokes and “Her” little penis exploded. I was physically and mentally drained. I can remember lying there, almost vibrating from the overwhelming sensations. Mistress Alegria covered me with a blanket and told me to rest, which I gratefully did.

After resting and recovering Mistress Alegria allowed me the pleasure of using some nice scented oil to give Her lovely and strong body a complete massage and rubdown. I could feel the tension in Her muscles and I worked hard to help her relax. Massaging deeply I moved from Her shoulders and arms down to her lovely feet. I’m not sure who enjoyed it more, Her or me. I absolutely love making my Mistress feel good. That, to me, is the essence of being a service oriented sub – making my Mistress happy. And I did my best.

Saturday was the Leather Flea Market and Play Party at the Crucible in DC. Shopping in the afternoon and playing in the evening. What a great combination.

The flea market was fun as we were both able to get some nice new toys. Mistress got a stun gun (to use on others I hope) and some nice stainless hand restraints (almost assuredly for me to experience). She was happy, although, like a kid in a candy store there was much She would have enjoyed having but could not get at this point. I so wish I could make all Her wishes come true. But alas some good things must be waited for. And Mistress Alegria is certainly much more patient than me. But at least I did get some great ideas for future gifts for my Mistress.

At the flea market I got a new, larger dildo for my butt plug harness, along with a vibrating insert that vibrates in time to ambient sounds, as my anal training continues. While it is a little large for me to accommodate comfortably at this time, Mistress  Alegria assures me that with a bit of effort and patience we will reach the point where I take it easily. I so want to make Mistress proud by being able to take Her big strapons. And I think that the vibrating aspect will really be a powerful tool in strengthening the transference of my pleasure center from “Her” little penis to “Her” ass. I fantasize about semen pouring out “Her” locked up little cock as the big vibrator is locked into me.

 Saturday evening at the play party was one of the happiest occasions I can remember. The Crucible was packed, with what must have been at least a couple hundred people. I had so much fun that as I write this the next day I am still tingling.

Mistress Alegria decided that it was time to take my feminization and slutification (if that is that a word?) to the next level. We were both diva’d out to the max. Those of you who know Mistress Alegria, or have looked at Her gallery here on our blog, or on her site – – know how beautiful She is. Let me just say that She was at Her most beautiful last night. I was decked out in my sexy pink and black striped fishnet cutout mini-dress (purchased here) with the matching thong fishnet panties. I also had on black heels and a matching black hat. A pretty black purse, my chastity cage, and my butt plug and harness completed my attire. It was definitely an attention grabbing outfit.

I wore my dress under normal male street clothes driving to DC. When arriving at the Crucible I then removed my male clothing and went into diva mode. I had such fun swaying to the music and making a complete display of myself. Smiling coyly and playfully posing as I knew I stood out in the crowd was so delightful. At one point in the evening I asked Mistress Alegria if I would be ok taking my male clothing out to the car so I did not have to worry about keeping track of them. Since she said it would be ok I went ahead. Strutting down the street outside, in front of the crowd from the Crucible as well as from the bar next door, I felt like a street-walker, and certainly looked like one. My heart pounded as I walked outside in public in female attire, exaggerating my strut and playing the part of street whore, for the first time. What an exhilarating experience.

However, I had to remember that my real job for the evening was to serve Mistress Alegria. She had play on her mind. I carried Her bag, kept Her toys organized, and cleaned up behind Her and Her playmates, as She played with friends. I also made sure that She and Her play partners had beverages to stay hydrated. A particularly brutal CBT session was certainly interesting to watch. I concluded that my eyes and stomach are definitely stronger than my balls, as watching was fun but I could not have endured the treatment She dished out.

As the evening went on I found out that I was not neglected regarding play for my Mistress. I was bent over a padded horse with my ass in the air. Mistress was fairly harsh with Her whip and pounding on my butt plug, driving it in and out. However I was so high on the excitement that what would have been uncomfortable if alone at home did not even faze me.

As the evening wound down Mistress Alegria told me She was proud of me for having come out in public dressed as I was, for taking a good whipping, and most of all for serving Her needs and desires so well. And I could see in her eyes that she meant it. And I was proud knowing that I was at least in part responsible for the smile on her face and the beautiful glow that enveloped her. Throughout the evening I received numerous compliments from so many attendees there regarding my outfit and my service. The most complimentary thing I heard, from several of Mistress Alegria’s long time friends, was that they could not remember seeing my Mistress so happy, and that they knew I was a large part of that happiness. It was nice to know that my Mistress is happy and that my efforts are appreciated. That, again, to me is the essence of being a good service sub.

I know that I still need additional training. I am still somewhat new at this. I also know that Mistress Alegria has additional plans for me, some of which she has hinted at, and others yet to be revealed. But at this point I can say without fear of contradiction that I could not be happier.

And I am the luckiest man on earth.

Monday, March 8, 2010

My Feminization

littlechasteguy says:

I, as I imagine is the case with most men, certainly most men with submissive tendencies, often fantasized about forced feminization.  However, I never went very far with it because I thought that to be really feminized required being passable as a female. With my hairy body and the need to maintain my general appearance due to constraints resulting from my “vanilla” life I always figured feminization was not for me. But I did enjoy wearing female panties, of which I have a nice collection. Then, in casual conversation I mentioned this belief to Mistress Alegria. 

Mistress Alegria, I am coming to understand more deeply, is very perceptive and listens to all I say, often filing away little tidbits of information for later use. This belief of mine was no exception.

Several weeks ago I was over at Mistress Alegria’s when she just happened to be going through some the feminine attire she uses for those who want to be feminized. As part of my service to her I was helping her sort through her items. As usual I was naked except for my chastity cage. At one point she had me try on a skirt just to see how it looked. I enjoyed the feel and thought it looked good, although I again made the point that with all my hair I could never pass as female so feminization probably wasn’t for me.

That was when Mistress Alegria sprung her latest surprise upon me. She told me point blank that being able to pass as female was not at all important. The next thing I knew we were going through her items with me trying them on to see which items fit me. We soon had a collection of skirts and blouses that fit, although not everything matched. There was also a red and white French Maid’s outfit. Most items were rather skimpy and slutty looking. I was told that we would need to fill out the wardrobe. As we tried on the outfits Mistress Alegria told me that she would be taking me to various events dressed in these outfits and that I had no choice so there was no point resisting. While my mind still harbored a vestige of resistance my body quickly gave in as her little cock swelled with excitement in its cage.

The next day we went to a friend’s house to have some pictures taken. Mistress Alegria had me dress in an orange skirt and white top, wearing high heeled boots, for a number of photos. Some of these are now posted. That was the first time I dressed in the presence of someone other than Mistress Alegria, and I found myself to be perfectly comfortable.

On the way home that afternoon Mistress Alegria told me to pull over into a little shopping center. The next thing I knew we were in a shoe store, buying high heeled shoes in my size and a pair of casual sandals. The next thing I knew I had four new pairs of female shoes.

Leaving the shoe store she directed me two doors down to a little clothing boutique. We left there with several feminine tops and a little black and white striped miniskirt.

Since I knew I had no choice in this matter I decided to go ahead and embrace it. When I arrived home I looked online and found several more items that I thought might look good. With Mistress’s permission I purchased them. Soon I found myself with a complete wardrobe, including accessories.

Last weekend on Saturday night was my true coming out. Mistress Alegria had invited over for dinner several friends, including a Mistress friend of hers and her collared boy, along with another young lady in the lifestyle. I prepared a lasagna meal, including salad, garlic bread and dessert and served it in my new French Maid’s outfit. That was a tremendous experience. It took every bit of fortitude I had to maintain my composure as my excitement was boiling over. The combination of humiliation and what I perceived to be genuine compliments really was a lot for me to experience.

After cleaning up the dinner mess, with help thankfully, Mistress Alegria had me dress for the evening out. We were going out to the local play house for a social gathering. Again the excitement and trepidation nearly overwhelmed me as I dressed in my new black and white miniskirt and a black top. Black lacy panties, a pair of heels, an anklet, Mistress’s collar, my butt plug harness and a hat completed my outfit. I looked so slutty. However, all those present assured me I looked very good and would be fine. Again I decided to truly embrace my newfound circumstances and try to enjoy myself.

At the playhouse I did have a good time. I confidently pranced and strutted around in my slutty attire, amusing my Mistress and making her proud. I was again gratified when one of the young ladies that I did not even know complimented me on my outfit, noting that she really liked my top. I graciously thanked her for the compliment.

As the evening went on at one point Mistress had me remove my panties and bend over a bench so she could give me a little flogging. While not a pain slut at all I am very much an exhibitionist. This public flogging while dressed in this manner was highly erotic to me. However, later came the moment I somewhat dreaded.

Mistress Alegria and her friend Mistress M were discussing what a slut I looked and acted like. (They assure me that being a slut is a good thing.) Then Mistress Alegria asked Mistress M if she wanted to see just how slutty I really was. Of course Mistress M was interested in seeing. So Mistress Alegria had me remove my butt plug harness. She took me to a good spot and proceeded to finger fuck my ass. I squirmed and begged for more while Mistress Alegria explained that this was how I now received pleasure since “Her” little penis was locked up, deservedly so. In between my grunts and heavy breathing I agreed with my Mistress and thanked Her for fucking my ass.

Later that night Mistress whispered in my ear that she was very proud of me. I had endured a lot and grown a lot in my submission to her that evening. I was so happy to know I had made Her proud, and at that moment I too was proud of myself.

I must say the physical feelings and the humiliation of begging for more fucking in a public setting like that was truly cathartic for me. A completely new window has opened up for me, one that I think I can embrace and enjoy. I will say for sure that I am looking forward to more opportunities to dress in a public setting. I have an entire wardrobe to show off.

Those vestiges of resistance regarding feminization I had several weeks ago are now completely gone. If Mistress Alegria wants me to be her chastised little feminized toy I am more than happy to fulfill her wishes.


Saturday, March 6, 2010


Mistress Alegria says:

Let me start by acknowledging all those readers out there who've taken an interest in the chastity journey of My littlechasteguy, and in his transformation based upon My guidance. We started and maintain this blog not only to document our activities and feelings, but also to hopefully help others that may be in a similar journey. I would particularly like to thank all our new readers who've learned of us from The Kristen Archives. And I would like to thank Kristen for providing the link to here.

Feminization of My littlechasteguy began a couple of weeks ago. It was the next step in not only owning him physically, but also to enhance and enforce even further My complete dominance of his mind as well as his body. By progressing beyond simply wearing panties to a full blown wardrobe this is being accomplished.

When we first embarked on this journey My littlechasteguy was a bit reluctant regarding female attire. However, this reluctance disappeared once he found out:

1. He has no choice!
2. He doesn't have to pass as a female when dressed.

Littlechasteguy was fortunate that amongst My collection of very pretty clothing were several items that fit him well. A trip to a shoe store and one of my favorite clothing boutiques was also a lot of fun (at least for me) and helpful. My littlechasteguy was also allowed to go online to order a few items. He now has a nice collection of skirts, blouses, dresses, shoes and accessories to go along with his already nice pantie collection.

Littlechasteguy takes great care regarding how he dresses and grooms himself in the "vanilla" world. I am pleased that he shows the same zeal when it comes to choosing his female wardrobe. He is a pretty little boy when all dolled up.

The Phoenix Sapphire chastity device My little penis is locked into, because of it's small size, doesn't compete with the appearance of the clothing I choose to dress him in. When dressed in a pretty miniskirt and panites, and wearing his sexy high heels the cage is not even noticeable. But we both know it is there and that it is  nice a full as My little cock gets so excited and swells to fill the cage when My littlechasteguy is adorned in his pretty female attire.

Feminization for me does not involve the typical type of clothing I've seen most wear. No frilly "sissy" outfits will do for My littlechasteguy. I saw littlechasteguy's petite size as a chance to really "slut" him out and draw even more attention to him, helping the humiliation factor further along! This reinforces my dominance and keeps his submission under check. This is also a reward for him since, as females are superior to males in his mind, dressing as a female is a good thing.

Last weekend was the first time I took him out in public in full female attire, as we attended a social event at the local play house. He was dressed in a black and white miniskirt with black lacy panties, a black halter type blouse, 3 inch heels, a nice hat and anklet as accessories, and My collar of course. He painted his toe nails pink (which still remains on as a reminder). And of course he was wearing his chastity cage and new butt plug harness. I loved watching him happily prance around in his outfit, with me knowing that the butt plug deep in his ass was doing it's job regarding training him to have his ass be his pleasure center. So much fun for Me! And My littlechasteguy seems to have taken this next step in his transformation quite well, as he knows that his mission is My pleasure, and I take great pleasure in using him as My little play thing.

As this journey continues, to places yet to be revealed to My littlechasteguy, we will continue to post our activities and thoughts. As always, questions are welcome. We will respond to all, either directly or in future postings.

As this is posted several new pictures of littlechasteguy dressed have also been posted on his feminization picture page. More will follow.


Mistress Alegria