Wednesday, December 28, 2016


This installment of my series continues the events during my anal training and blue ball filled Christmas, but unlike the previous part in tells only about the events of the Christmas eve. However, it was quite a Christmas eve.

Just like normal people, my intention was to spend the eve doing Christmassy things, but the evening turned out quite an eventful one. Since I don't have anyone to give or get presents from, the main event was my one person Christmas meal. However, since I wanted to be nice and clean I wanted to take a nice shower first, as an option to Christmas sauna.

As I was in the shower my mind started to wonder though and wanting to be completely clean, I ended up giving myself a nice rectal rinsing, This time I used the actual shower hose, not the one beside the toilet, after I noticed you can screw the head off of that as well.

I was surprised how much more normal and less humiliating it felt when you were in a shower yourself. The shame you felt when you dropped your trousers and started to stuff the hose to your asshole was more or less gone when you were already nude and standing in the shower.

And, since my asshole was now nice and clean I simply had to test it, first with the prostate toy, and afterwards with the cock shaped vibrator and the inflatable plug, whether being neglected had affected it at all. As it turned out, it hadn't. As I finally got out of shower I felt more clean than I had done in a long while.

I was also somewhat curious to know how big I was supposed to be now. After measuring the inflatable one I could say for certain I was at least 3,5 centimetres wide. As I was doing this my virtual friend came online and I could tell her the good news and we discussed the matter of anal toys for a while.

Things led to another and soon I was suggesting I could check whether it would be easier to slip in, not a cube shaped but a heart shaped ice cube. As I may or may have told you, I have several silicone trays, the heart shaped one being my favourite.

It was a surprise to find out the round shape wasn't easier to put in than the cube, quite the opposite. Then again, being just out of the shower I think my asshole was more dry than a desert. Also, with heart shaped one it was much harder to determine whether the cube is in or not. With the cube shaped one there was no such problems.

To check whether there would be any difference now I suggested could try with the cube shaped one next, and my friend complied. Thinking back, it was hard to say whether this was any easier now, but it did feel so much better after I had gotten it in. So good in fact a little while later I suggested whether I could put in twice in a row, and again I got a permission.

I decided it would be fun to do this using my wanking mirror. I set it to the right angle, removed my bathrobe which was the only piece of clothing I had on anymore, and got to work. I got the first ice gube, lifted my other leg on the tiny piece of desk that's between my computer and the mirror.

I faced the mirror, and as I started I was amazed how revealing this position was.. I could see... well, everything. I could see my bent long leg, my ass, my penis and testicles hanging, my naked upper body, my boyish face, and my hand, starting to push the cube in. As narcissistic as it sounds, I was amazed how hot, pervy and fuckable I suddenly looked like in my own eyes. For a while I couldn't but to admire my nude for.

I admit that at this point I had gotten very horny. I even mentioned this to my friend and said I had gotten to the point I had an insatiable need to cause myself pain. My thoughts were in clothespins, but my friend, being more into anal things and pleasure than pain, told me to but my biggest toy, the pink jello plug in without any warm up.

Naturally I did as I was told, first lubed it a bit and then started to push it in. I must say I was not only relieved but also disappointed as it went in quite easily. There was no feeling of being broken in half, only deep satisfaction and feeling of extreme comfort and I pushed the base to my buttocks, and felt some lube dribble out.

The biggest problem, in fact, was caused by water, not my sphincter. I put the plug in using a 'big push, small pull, big push' technique I had noticed to be effective, and every time I did the small pull a little amount of water got out, taking the lube with it.

Even though putting the plug in hadn't hurt much my friend was understanding and merely said that sometimes pleasure is more important than pain. However, being the state I was in, was almost begging to be ordered to put some on. My friend complied, and told me to put six of the easiest ones on testicles. In a matter of less than a minute I had them on.

Clothespins are, if I haven't had a chance to tell you, one of my favourite means to cause pain on myself. The easy ones I had just put on hardly feel as you put them on, but the longer they're on the more intense the feeling becomes. It does that very gradually though and if you're horny enough it's sometimes hard for you to realize how much in pain you actually are.

The big ones, however, that were on my nipples and caused my accident in the beginning of December, are really nasty and I do have to be pretty horny to use them. Same goes with a couple of wooden ones I use only with great caution.

This time, however I realized very quickly the gradually increasing pain on my testicles and the mere feeling of them being there started to make me even more horny I wished. Not only there was the pins, but also the huge plug in my ass. In fact I started be afraid my body would take over and make me cum involuntarily, which was something I did not want to do.

I put my bathrobe back on, tied it and told everything my friend. She said she understood and that she didn't want me to cum either. Therefore she said I could take the pins off... in five minutes. With hands shaking I asked her whether she understood how hard that would be for me, and she answered she understood it perfectly. So I have the best friend or what?

I managed not to cum, though and as I finally removed the pink clothespins from my testicles I nearly hollowed out loud. I was happy, though since this was not the kind of pain that would make me cum.

All the while this took place we continued our conversation. At some point I looked at the timestamps on our chat log and almost didn't believe my eyes. According to them it already had been in my ass for an hour and a half? Not that long a time ago keeping it in an hour had been an achievement.

I told this as well as my disbelief to my friend and she didn't seem surprised at all.  However, I didn't want to take it out and instead begged it could be in full two hours. After a slight hesitation my friend agreed to it.

Around this time my friend had other matters to attend to, and started to answer more slowly and I continued my experiments with the big plug in my ass. I bit earlier I had noticed my the technique in which I put the base part sideways and then do walking movements didn't have as big effect than earlier. My friend offered ice as explanation, the idea being it has numbed my ass.

However, as I now did the hip thrusting exercise that earlier made me feel almost as if my asshole was ripped open, I didn't feel a thing now. This got me curious. I reached under the plug's base and started to feel the rim of my ass. The sensation was incredibly good and it almost felt I did have a boy pussy. Then I started slowly easing my finger between the plug and the sphincter. I tried it form couple of direction, and after a while managed to do it.

Was this even possible? But there it was, I thought as I moved my finger inside my colon, lodged between the rim and the plug. Wanting to make sure, I got a old toothbrush I have big stash of, applied some lube to the tip of the handle and then started easing it in. In no time I had slid the handle inside and was moving it back and fort. As I finally took it out and looked at it I was pleased but still in a bit of disbelief. The handle was round and ergonomically designed, but it was easily one centimetre thick.

I finally managed to keep the plug in way past two hours. When I finally did take it out, I didn't do it at once, but gradually. I tried several positions and finally decided a deep squatting one would be the best. I took it a bit out, then put it back in, then a bit more, and finally so that it passed the sphincter, and then back. Then out again, then back.

Again I tried several places and positions and finally had my leg on the toilet seat's water tank, hand reaching back. It felt amazing. The toy that had been mere weeks ago way too big for me. One that is at the moment biggest toy I have. And here I was, fucking myself with it into my ass like it was nothing.

It felt so good I finally had to force myself to stop, since I could have continue for hours.
As I felt my asshole now I think I have never been more proud of having one. As I said, it felt I really had a pussy now. A pussy than was now loose, slick and open. But I nothing to put inside it to test it looseness. Or had I?

Well, under an half a minute or so I had gotten the ice cube tray from the fridge and held the first crackling ice cube it in my shaking hands. The first one went in as easily as you might guess. After the first five ones I had to take a short break since the sensation was just too intense.

At first I had no clear plan when it came to the amount. However, I quickly realized I wanted it to be an even number. Ten? Ten sounded nice, but could I do it? After a minute's pause or so I continued. My heart still raced, as it had been doing after the first cube.

The next four caused a bit more difficulty, since I could feel the previous cubes inside my rectum as I pushed the new ones in. In couple of instances it felt almost as if the "lips" of my asshole were still gaping as I put the next one in. I had to gather my courage a bit after the tenth one, but I knew I wanted it in. After I had managed to push it in and stood up tightening my buttocks I felt the last ones to move like icebergs as they searched for their place inside my rectum. It felt funny, but very nice.

When I had played with the ice cubes the last time I had spent considerable time on the toilet seat getting the cold water out. This time however, as I checked the situation half an hour later I was surprised since nothing came out. Also, it took this time way over 12 hours before there was need for anything that can be called a regular number two. What can I say, body is a curious contraption.

After I had washed the pink plug I went to measure it. It was four centimetres wide, and I had just fucked myself with it. Plus I had managed to insert a centimetre wide toothbrush handle in my rectum in the same time.

This not only meant buying any kind of plug under four centimetres wide would be a total waste of money, but also that the five centimetres wide, nice and round plug I had earlier got interested in, but then discarded it for being way too big for me, wouldn't be such a bad purchase after all?

All in all, I must say I have just had the most freaky, unconventional and fun Christmas eve of my whole life. Wouldn't you agree?     

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