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 – therubeerooms.com – 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.