Friday, December 16, 2016


This is the tenth part of “My boy pussy project”. Who would have thought. In this installment I am bringing this series closer to its core subject, as well as the one of the blog itself. In the previous part there was very little anal training and even more less chastity, after all.

For everyone who read the last installment it was clear I wasn't doing very well spirit wise at the time I was writing it. Therefore I decided with a virtual friend of mine it would be a good idea to put a stop to my cumming for a few days at least.

It seems that even though I left the chastity behind me, at least in a sense the idea was to reach longer and longer periods of being denied, I still yearn for it. Immediately I was told I cannot cum until Sunday I felt inner peace fill me, as well as extreme horniness.

I wouldn’t have to worry anymore whether I should cum or not, and if yes how and when, because that possibility had been taken away from me. I wouldn't have to to cum, anymore, simply because I wasn’t allowed. I need to be kept in control, it seems.

In fact I have added the chastity counter to my blog again, after it had been away well over a week. At the moment the counter reads three days and ten hours, which itself is a pitifully low figure, I know. But it’s the longest period of chastity for me since the beginning of December.   
This little pause will be a good idea when it comes to the well being of my clit, as well. The damage caused by she hair removal cream in the head of my clit heals much slower than I would wish. It very well may be that the rate my little clit is healing up will determine when I get to cum next time.

My new found chastity has also created a problem of sorts when it comes to my anal training project. If I don’t masturbate anymore, what point is there to stretching my anus? In matter or a very short time cumming had become a natural result of putting something in my boy pussy.

Therefore there was a few days pause in my anal stretching as well. Also, for various reasons, I really didn't feel like doing it. Yesterday I finally managed to rekindle my interest again. One of the reasons behind it was the fear my boy pussy would lose it flexibility if I neglected it totally.  

The main reason, however, was the fact that the prostate massager I had ordered last week had arrived a few days earlier. And quite frankly, it felt silly to let the device I would have afforded to remain in its package, unopened and unused.

The fact I that first attracted my attention was the one most people seeing their new toy notice, namely the size. The thing was really, really small. It had looked so much bigger in the picture, but in reality the tiny t-shaped plastic thing fit in the palm of my hand.

It looked very stylish, however, and no doubt a lot of effort had been put to to its desig. Also the material was nice, the handle part was very sleek, whereas the inserted end which resembled some sort of strange fish had almost velvety feel.

Not wanting to spoil the experience I relaxed my boy pussy first with the small plug and then gave myself a little enema. Then I lubed the new toy and started to insert it. 

First there was some difficulty, most likely due to the shape, but after I had gotten it past a certain point it almost felt as if my asshole suddenly just sucked it in eagerly and I remember smiling broadly as it happened and a surprised “Oh… Oh!” escaped my lips. I am sure this is exactly what the design was made for, but it felt nice nevertheless.

When it was in the first impression I had was a surprise. I hardly felt it. Not the part that was inside me, nor the bending part that pressed the area between my testicles and anus, and that was supposed to feel so good.

I walked back to my computer and sat on the chair I had first put a towel on, and noticed I could do it without any difficulty. The sensation was having the thing inside was nice, not as nearly as invasive and violent than with the butt plugs.

As I moved my hips back and forth I could feel the thing slide inside and under me, It felt nice, as well, but no, there wasn't an immediate male anal orgasm. After a while I went to lie down on my side, tried to relax and see whether anything nice would happen.

I tried all sorts of things, and noticed the most fun I got when I rotated the handle and felt the end doing the same inside me. However, as I pressed the massager in a way it should be in contact with the prostate the feeling wasn't ecstatic, more than anything it was unpleasant.

All in all I have to admit the first impression of my toy was a disappointment. I hadn't expected a mind shattering orgasm but it was somewhat of a let down to feel absolutely nothing. But as far as I know, there are those who have had the same experiences I have, and prostate massaging is an acquired skill.

If anything, the toy was almost too comfortable and I commented to my virtual friend who was on-line and seemed a bit surprised by the lack of effects the toy caused in me, that it was something I could see myself riding a bike with very easily, as well as sleeping with it in. I may have to test this at some point.

However, at the time the test run was such a disappointed for me I decided to continue my session with some of my older toys. I went to the bathroom, took out my big cock shaped vibrator and after lubing it a bit started to insert it gingerly. After all, it had been some while since the last time.

I was pleasantly surprised as I felt the vibrator starting to go into my asshole. This time I gave it a plenty of time. I wouldn't have to cum this time, so it was only me, my asshole and the divine thing that was going inside me. I leaned forwards to the washbasin, kept my eyes closed and pushed the thing in, then out a bit, then in so it went in deeper every time. I turned the power up bit by bit so that soon the thing was vibrating with full force deep inside me.

As I finally stood up I could feel with my fingers only the end of the huge thing stick out between my smooth ass cheeks. The whole procedure had been so gradual and done without the haste this time I had no lube on my fingers which usually made this part or turning the power up or down very messy.

I went back to my computer and was able to sit down. I didn't sit down with all my weight, but I did notice I could “fuck” myself in the ass by lifting my hips up and down, and feel the huge thing going deeper into my asshole, and then a bit out again. 

I did this quite for quite a while and finally I had to admit to my friend I didn't want to take the thing out anymore. This seemed to amuse her somewhat. Sure, there was some discomfort, but in a way it was a good discomfort. It wasn't direct pain, only slight ache around the anus.

But the last toy was yet to do, namely the black inflatable plug. Part of the reason I didn't want to stop playing with the vibrator was the fact the inflatable toy is somewhat intimidating for me. It is no doubt the nastiest and the most vicious of my toys.

However, as they say, sissy’s gotta do what sissy’s gotta do. I went back to the bathroom, and with still keeping the huge vibrator in by clenching my ass cheeks shut I lubed the black rubber plug. Only after that I took the vibrator out, which by the way felt divinely as well.

Inserting the black plug wasn't very hard, but the nastiest part was still the one when the widest part goes in. Also, my asshole still tried to push the plug out as I started walking and I had to make sure I stayed in the way it was supposed to.

As I sat down in front of my computer and informed my friend the last phase was now completed. I felt my heart racing and hands trembling, the way they always do with this plug. As I told this to my friend who apparently has a lot of experience on the similar toys she has experienced the same thing.

In a way it’s pity this plug is still a bit too much for my boy pussy, since after I had it for a while I realized I couldn't take it anymore. I would have like to keep it in longer, and perhaps set myself a time limit, which I could try to rise in the future. Neither did I even consider using the pump option this time.

However, as took the thing out, which is usually much more painful than putting it in, I let out a yell which I always do due, but realized it didn't hurt as much it had done on some previous times. My friend said this was a good sign, since it meant my ass was getting more and more used to it.

The last me I had given myself this sort of ass ramming I had felt it several hours. It is hard to describe it. It wasn't pain as such, not even discomfort. Only that something was happening inside you. This time around I noticed something similar, but not as nearly as intense. Truth to tell after an half an hour I felt completely normal again. Even the next morning it took me a while to remember the whole thing, since there was no sensations to remind me of it.

It seems my virgin little boy pussy is gradually becoming quite a pro. I couldn't be more happy about it. 

Three days, twelve hours, ten minutes and counting...  

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