A very long time ago, Master made the decision that I would train my ass cunt for his pleasure and so he happily purchased an anal dilator kit and sent it my way.  At first I was extremely nervous for although I always enjoyed anal sex and had participated in two weeks worth of training with a pyrex plug, the idea of actually training my hole to accept such a large object (5th dilator) was scary.  On top of my fear of trying to work the hard plastic into my already shy orifice, I had visions that once I was stretched to accept such a wide toy, I would no longer be tight enough for Master to enjoy.

Fortunately the human body is a rather amazing piece of machinery and after seven weeks of continual use, I was delighted to learn that my anus was not left gaping, that I did indeed still have control and could squeeze my anal sphincter tight or push it open to relax.  This knowledge along with the pleasure I received the very first time Master slid his cock into my ass cunt, is the reason why I fully believe in such training and why I have returned to those hard black devices.

My training will vary this time around as I no longer require such a lengthy period to relax my muscles. In fact I started a period of training yesterday and I was able to skip the first two dilators, starting with the third.  My goal this time is not so much to stretch but to teach me pleasure about using my ass cunt hole and I think my attempt yesterday definitely pushed me in the right direction.

One of my biggest concerns with regards to anal sex is I am afraid I will have an accident as in I will urinate either on myself on Master or on the floor and I believe because of this fear I often squeeze Master's cock too hard, pushing him out of my hole.  I also panic and once I panic all my muscles tighten beyond the point of pleasure and therefore cause Master to stop fucking me.  I no longer wish to allow my feelings of insecurity to dictate an activity which we both enjoy and so with embarrassment and humility I sat my naked bottom onto the toilet seat and slowly inserted the third plug.  I worked the plug in and out of my ass cunt and even though I felt that all too familiar pressure to pee, I did not worry because I was sitting on the toilet.  The third plug felt amazing and without hesitation I moved onto the fourth.  Once again I worked the plug into my slightly stretched hole, ensuring I felt no pain, not rushing the experience and eventually the fourth dilator slipped in and that wonderful sensation was recreated once again.  I pulled and pushed and pulled and pushed that fourth plug in and out of my ass cunt for over 40 minutes and although I felt the phantom need to pee often, only once did I actually secrete any amount of urine and the amount that leaked out was maybe 1/4 of a teaspoon.

Although I was exceptionally pleased with myself for being able to fuck my hole with the fourth plug I desperately wanted to be able to use the fifth and so with greedy lust I lubed the 5th and very slowly pushed the rather bulbous head into my ass cunt.  In all reality, the last dilator should be able to fit for its girth does not exceed Master's; however, I believe because it is hard and rather unforgiving it is not as easy to push inside.  I worked the last plug for over 20 minutes and even had Master help; however, the pressure was too intense and as Master tried to push the head past my tight ring I could feel that awful burning sensation begin and I definitely did not wish to tear for I had been craving Master's cock and if I was injured Master would not use me.

It was an exceptionally humbling experience to have Master walk into the bathroom while I was sitting, practically naked, on the toilet, inserting a toy into my ass cunt.  And I believe part of the arousal I felt was because I was embarrassed, because I felt so incredibly vulnerable. With that vulnerability though comes a sense of freedom, the same freedom that allowed me to ask Master earlier in the day if I could give myself an enema so that I was clean for Master's use.  That vulnerability always resides within me; however, there are moments such as the one of me sitting on the toilet that bring about a heightened awareness and although I am still learning to accept that part of me, it feels good to know I can go there, that I am open enough to explore.

And exploring is something I find myself doing more of these days, especially with regards to pain.  Now I have stated numerous times that I am not a masochist, not in the actual definition. Still, I have been noticing that my mind seems to respond to light swats Master lays upon my flesh and my pain threshold is no longer as weak as it once was.  In fact I am actually starting to receive pleasure when Master uses such tools as the cane, the paddle, the flogger and even his hands and I experienced some of that pleasure last night when Master smacked my flesh, starting with a cane and then a crop and last the flogger and although some smacks stung and although I know Master was not using any amount of force, had he done that two months ago I would have loathed every minute of it and now I liked it, I wanted more.

I wanted more of everything and luckily for me I received more; I received Master's cock.  My mind was ignited after feeling each implement strike my body and as I bent over, grabbing my ankles, I found myself moaning as Master slipped his cock into my ass cunt.  I can not begin to express how amazing it felt to be used in such a manner. I believe it was the very first time that I actually felt connected with Master, with the penetration of his cock, of my ass cunt accepting him.  In the past I was so focused on relaxing, on being pleasing that I would disassociate myself from the exchange and instead target my thoughts on the act.  I of course was not aware of my mind set until last night, until I experienced something entirely new and all I can say is, holy!

Our entire exchange was sexual and primal and aggressive and unbelievably pleasurable and I am confident that much of that stems from me opening myself to pleasure, to trying something new, to pushing aside my fears and doubts and insecurities and embracing who I am and what I want rather than running from it.  And much of it had to do with my training and my willingness to push through my moments of embarrassment and to get to know my own body, something I have not truly done before this year but something I am looking forward to exploring in the up coming months.

Let the exploration begin!

Related reading:

1. Training the anal sphincter. My anal train­ing adven­tures have been recor­ded both on Master’s...