This installment of my series will concentrate solely on the subject it is supposed to do, namely my little anus. In fact as I am starting to write this part I am still pretty disoriented and amazed. But I will try to tell everything in order so it will make some sense. Let’s just say I had no idea in the morning where today’s events would lead me to.
I admit I realized shortly after waking up this wasn't going to be a productive day for me. I was extremely horny immediately after getting up and since my clit had begun to show small signs of healing, I even dared to wank a bit. It had been several days since the last time and it’s amazing how one is capable of forgetting in that short amount of time how great it feels.
The problem, however, was that since it I had now been almost five days of chastity behind me, I noticed the safe amount of time to pull my limp clit was much, much shorter now. I had to be really careful since the last thing I wanted was another edging accident. So, I had to think of something else.
It all started innocently enough, with the intent to give my new prostate toy another chance. By the late afternoon I was feeling a bit sleepy and thought it would be interesting to see whether I could take a nap wearing not only the prostate massager but also my chastity device I hadn't worn in quite a while.
I put the both on, even though the latter created a bit of difficulty. The cheap device is equipped with four different sizes of rings to put around your balls, and at the time I got it I hardly got my huge testicles in the largest. However, body seems to adapt to strange things I do remember that by last summer I was already on the third one.
As I put my sack through the ring now, however, I noticed the largest one I was able to use was number two, and even that seemed a bit tight. After I had both on, I had a strangely comforting feeling. Almost as I was fully clothed, and wearing some sort of inner harness, even though I was totally naked at that point.
I lay down and managed to fall asleep very quickly. The sleep wasn't the most sound though. I kept waking up and every time it took a while for me to understand why I felt the way I did. Finally I started to play with the massager in my ass and couldn't continue my nap anymore.
So I got up, sat on my computer, took off chastity device that by now hurt way too much, and started to explore my new anal toy’s possibilities. I still found that the thing I liked the most was a wide rotating movement, which made me feel the device turn at the mouth of my asshole.
I do believe I got closer to the effect that was the devices idea. After doing several things with it I started feeling… let’s just say something within me. I noticed my heartbeat rose and almost as if something had been moving in my limp clit.
I admit, I was trying to make myself cum. Even though I wasn't supposed to, it would have been so wonderful to have my first sissy orgasm, or at least to get to feel what “being milked” felt like, a thing I had so much about. Finally my hands as well as ass started to tire so I had to stop it.
Since my asshole was no nice and loose now, I decided it would be a good idea to have a real anal training session and moved on to the cock shaped dildo. I went to the bathroom, lubed the thing and started to insert it to my anus. The whole thing went the way I described in the last part and soon the vibrator was inside me all the way.
I started to move it out, and back in. I realized I had progressed in my training to the phase in which I enjoyed the actual movement, the feeling of the hard plastic thing to go in and out of your asshole, not just whether you got in or not. I even tried for a while how it felt if I was on all fours on the bathroom floor.
I rotated the thing in my ass for quite a while, since I knew I would have proceed soon to the nastiest toy I have, the inflatable plug I still found a bit intimidating. Finally I got up, started to lube the plug and after taking the vibrator out I started putting the black one in.
This time I decided to fuck myself with the plug first a bit. This seemed to help, because as I finally pushed the plug all the way in I was surprised. There was less discomfort now than on any of the previous occasions.
As I stood up I realized my heart wasn't racing and I could think much clearer. I even managed to wash the toys I had used after I had wiped myself clean from the lube that’s usually everywhere. I felt surprisingly coherent and normal, mentally as well as physically.
I walked around in my apartment holding the balloon like end in my hand and after a while started pumping it. This time I didn't go straight to eleven, so to speak. I pumped it a bit and when I felt my insides couldn't take it anymore I stayed there a few moments and then I let the air out.
The sensation was a curious one. Every time I let the air out I had to check whether the plug was still in, because I felt as if the plug had just disappeared somewhere, and that there wasn't anything in my anus. And then, after a few seconds I felt my ass somehow… contracting. It was an interesting sensation.
I must have done this almost ten times, until I finally got bored and removed the plug. When I looked at it in my hand I was amused. I hadn't even removed all the air from it! Still, I didn't even notice the fact as I took it out.
This gave me an idea. I removed the air, put the plug in, which was now easier than I could have ever imagined, pumped some air into it and then started to pull it out before deflating it first. I did this a few times, and put more and more air in every time. Every time it plopped out nicely.
On couple of occasions I even stopped the plug half way, so the inflating part was at my sphincter, not inside my colon, and then started pump more air to it. I was surprised to notice this was way less uncomfortable than the device expanding inside the colon.
As I finally watched the still inflated, balloon shaped dildo I had just yanked out of my asshole I couldn't believe my eyes. It was wider than my arm was! It was almost as big as my fist. In fact I do believe the size was about a fist of a woman. I do understand it was basically a balloon, and that my anus wasn't big enough to take in a fist or a hand, but still, it was a great feeling.
This got me thinking, however. As you may or may not remember, I had bought myself couple of weeks ago a pink jello butt plug, but had quickly understood I had had a bit too unrealistic idea about what my asshole could take in at that point.
I had instead bought the inflatable one that was slightly smaller, but was the one I still considered to be the nastiest of my toys. The pink jello one had stayed buried deep in my toy box, waiting for a better day. Was the day now? The idea filled me with with dread and excitement.
I went to my toy box, and with hands shaking took the jello plug out of it’s plastic package. I lubed the plug well and then started to insert it slowly. You may guess how overjoyed, relieved and thrilled I was as the thing went inside me! Everything during the past few weeks had paid off! I was so, so happy!
It felt funny to stand up now and feel the plug inside, and remember how horrible it had been trying to get it in. There it was now, not only like it belonged there, but it feeling pretty amazing, in fact. I played with the plug quite a while and walked nude around my apartment.
It was especially fun to realize I could rotate the end part and to feel the dildo swirl inside my well lubricated anus. I also noticed, as I pulled it out and back in again, that even though it was bigger than the inflatable one it didn't feel nearly as nasty. I think this was thanks to the slimmer shape.
From here on my recollections on what happen become less coherent. As you may remember, during my previous training sessions I usually progressed from one toy to the next, and finally ejaculated while wearing the biggest one.
This time, however, I realized I didn't want to stop, but I didn't want to cum either. In fact I didn't touch my limp little clit the whole time even once. I had almost uncontrollable urge to do it of course, especially when I pumped the inflatable plug inside my colon, but I kept my had off, since I didn't want to spoil all by cumming.
Therefore I started going back form one toy to another and alternating between them. I didn't want to stop since I realized I liked too much the way my boy pussy was now, slick, loose and relaxed, being able to take in almost everything. I even checked how many fingers I could get in, and was pleasantly surprised to discover my boy pussy was now a three finger pussy.
After a while I didn't need any kind of warm up period or easing the toy in. I could just grab a toy and push it in hard, keep it there for a while, then take it out, take another and do the same with it, over and over again. I completely lost count how many which toy was inside me.
I also examined how each toy felt and realized the jello one was becoming my favorite. It felt so smooth and slick moving inside me. I also realized I actually liked now the part where the widest part passes the sphincter, which had to this point been the part I dreaded the most. I fucked myself with the jello one for quite a while and concentrated solely on the widest part. I wanted that conquer my fears and making it my favorite.
Finally I had to more or less force myself to stop, since I knew I could continue ramming my ass the whole night. I washed my toys and the them to dry, walked to my computer with legs shaking but happy, and started to write this report. By now you may understand why I felt a bit disoriented in the beginning.
Five days, four hours and eight minutes...
