17.12.2016

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...

16.12.2016

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...  

13.12.2016

At the end of the last update I said it seems at the moment the time limit before I get insatiably horny is about two days. I had ejaculated on Friday after a thorough asshole ramming and it took all through Sunday afternoon for me to realize I was again too horny to think anything but edging.

It was a good thing it did, since I spent the night at my lesbian girlfriend’s place, and she wouldn't like it at all if I had become too amorous or made a reference to my little clit she doesn't like to think about. After I had come home though I realized the hornyness started to rise its head, and in no time I was edging again.

However, I knew I had an assignment of sorts to finish that day, and that couldn't just edge or masturbate all day. Therefore I decided to try something else. After keeping the small diamond plug in my ass and having fun with it for awhile I decided to do a hair removal.

Like the faithful readers of this blog know, I have done more or less complete hair removal a few times now, first with the help of my girlfriend, and after that alone. I do it to feel a bit more girly, or at least less manly, when my body hair had become too long. And considering all the anal training I had done recently it was high time for it.

So I got rid of my clothes, went in the bathroom and started to apply the cream on my body, from head to toe. Soon I was covered in it, and felt it to sting a bit, especially around the groin area where I had put it the most. This time I also I creamed the area around my asshole thoroughly, since I wanted my boy pussy to be smooth and hairless.

I gave the cream plenty of time to work, and stood in the middle of my apartment enjoying the warm air blower. After all, it is winter over here. After it had been over twenty minutes since I covered the last areas I started to shower myself.

Showering off is my favorite part. I love the way warm water washes away the cream, and with it comes off not only the cream, but also the yucky hair, and all that remains is the smooth, girly skin. I washed myself all over: the chest, the armpits, the belly, the legs and finally the crack between my legs, my boy clitty and testicles.

I loved the way my body now felt as I caressed myself with warm water running over it, especially my clit and testicles, but above all, my boy pussy. It hadn't felt like this, ever. It was so smooth and inviting now, not hairy and yucky like a real man’s dirty asshole.

The end result wasn't a complete success however. Sure, as I looked myself from the full length mirror I thought I looked so pretty and feminine. I couldn't believe it was my body. All the nasty hair gone. Even the legs had turned out okay this time and I had managed to get most of the hair off them, which is usually tricky. I caressed them ages after I finally sat down.

However, once again it was my clit and testicles that took the worst damage. I was prepared for it, but I was still shocked how sore and red they got. This time there was damage even around the area between my belly and my clit, that’s not supposed to be the most tender part. The way I looked made me feel very unsexy, which was unfortunate since I had wanted to feel quite the opposite.

I did manage to have a bit of fun, though. Among other things I put the red diamond plug inside my asshole, which now felt slightly different I have to admit, and tried to take an ass selfie. The latter turned out to be way more difficult than I had anticipated. Also, due to different sensations I was constantly afraid the plug would slip completely in.

My groin area was now red and sore, but on the same time the sensation did make me horny as well. Also, by that time I had been playing with myself most of the day and by the end of night I realized I was horny as hell. I had also found some nice teasing porn which seemed perfect for me. In fact, it was driving me out of my mind.

However, I was so sore down there I didn't dare to actually masturbate, but I knew that by simply fiddling the head I could make myself cum, or to give myself a nice ruined orgasm. After an encouragement from a virtual friend of mine I decided to do just that. I felt I had earned it, somehow.

So I started fiddling the head, kept doing it until I knew I was over the edge, and let the limp thing drop to my bathrobe. I gasped out loud as I felt the waves of orgasm wash over me. I felt a spurt after spurt of sperm shoot out of my clit to my bathrobe. It felt so, so good.

Afterwards I had to grab my limp clit and pull it just a few times, but that was already after all the cum had gotten out and the sensation begun to fade. I did manage to experience a few nice after waves, though.

I was amazed. That had been a ruined orgasm? It had felt incredible! A part of me didn’t anything but sissy orgasms like that, as long as I lived. Also, I realized, it had been the first orgasm after my first accident almost over a week ago I hadn't had something inside my asshole at the time of ejaculation.

The next day I wasn't feeling much better. Every time I checked the situation in my briefs I was reminded I wasn't a girl, or even a real sissy, only a guy after all. I was even reluctant to play with my boy pussy. There was some other things I felt bad about as well, some of them having to do with some things my girlfriend had said, and with my life in general. So yes, my mood was pretty lousy,

To get my mind off things I wanted to experience something nice. So I set my waning mirror the right way and got rid off my trousers and briefs. The masturbating still hurt, but I disregarded the feeling and continued. Soon I realized I was on the edge again.

If I ejaculated now, I knew, it wouldn't be an orgasm born from need. It would be merely me being selfish wanker wanting to feel good. Nothing more. But I knew I wanted it, wanted to feel good, even for a second. And this was what I was, I thought. A sorry, little selfish wanker, doomed to wank alone.

I got up, walked to my wanking mirror and dropped to my knees in front of it. I looked so pathetic. I hadn't even bothered to get rid of my t-shirt and fleece home jacket I still wore. The limp, red penis and my red balls hung between my legs.

Looking myself in the face I started fiddling it. In a matter of less than ten seconds I had brought myself to the edge. I let go of it and let my hand drop to my edge. I felt a little amount of cum dribble out as I kept watching myself in the eyes. I don’t even remember whether I felt an actual orgasm.

I looked down and saw a small puddle, almost too small for me to see, on the floor. Then I looked up to the mirror, at my penis that looked, if possible, even more small I had used to seeing it. I felt almost nauseated. I was once again the slave to that disgusting piece of flesh.

So no, it wasn’t the most glorious orgasm imaginable. But that’s the life of a compulsive masturbator I have now once again become, it seems.

11.12.2016

Welcome to "My Boy Pussy Project", part eight. Like I said at the end of the previous part, after my three ejaculations long cum spree it seems my libido had ran out of juice. For a couple of days I felt very unsexy and didn't even train my anus that much.

This morning however, I woke up with a big, nice erection and was immediately horny beyond belief. I must have spent an hour in the bed teasing and edging myself, half asleep, half in my fantasies.

Among other things imagined what it would be like to have a woman in my life doing all the things I have done to myself lately. She would start by making me put the tiny metal plug, since I had bragged I could get in dry. After I had gotten it in she would giggle as she would see how only a tiny bit was visible through the cheeks.

She would then order me to bend for her, and putting on rubber gloves she would start training my asshole with the plug the way I had told her I use to do. As soon as she thought my hole was relaxed enough she would tell me to go on all fours and arch my back. She would then lube up my eager asshole, and then the big vibrator, and proceed to put in inside me.

She would put it on and slowly but firmly she would fuck me with it. All the while I’d have to keep thanking her, and telling her how good it felt. Finally she would take it out and without even saying a word lube the inflatable rubber one. Firmly and slowly, and showing my asshole no mercy she would push the huge thing in. At this point I would most likely have my eyes shut, since it would feel so good.

I would hear her taking the rubber glove off and telling me to wipe myself clean, take a towel and follow her. In my study she would order me to lay out the towel on my office chair, and then sit on it. I would do as he tells me to, and gasp out loud. At this point I could ejaculate from a slightest touch.

However, to prevent any “accidents" she would shackle my hands behind my back, gag me, and even tie my feet to the legs of the chair so I would be unable to close my legs. For a moment she would disappear from the room, only to return some time later totally naked and carrying a chair. She would put it in front of me, sit on it, and with a broad smile on her face, start masturbating herself.

I couldn’t help but to whimper as I see her, only a meter from me, but totally unable to nothing but watch and suffer. Occasionally she would take a glimpse of my small, flaccid penis and smile wickedly at me, knowing very well how horny and frustrated I am, and taking great pleasure of my torment.

At this point I realized I needed to get out of the bed, and fast.

However, even though I did just that, I realized soon this would be a day I would mostly spend in front of my computer edging, which is exactly what I did end up doing, more or less. I had, however, errands to run in downtown. So, what a better way to combine my horniness to it than to do it plugged?

I took my red diamond plug, and inserted it into my asshole. I was very pleased it went in very effortlessly and even without any lube. I just put it in the opening, started pushing, disregarded the slight inconvenience and kept pushing until I felt it slide in.

I got dressed quickly, and was a bit surprised how natural this all suddenly felt. Here I was, a plug inside my asshole, dressing up to go to the centre of the city. As I was out I knew the biggest question was whether I have the nerve to get on my bike?

The thing was, I was a bit scared the saddle would somehow push the plug all the way inside my asshole, resulting to a trip to a local ER. I got on, and only after I had rode a while I gingerly let my weight descend on the saddle.

I was surprised how much it hurt. As long as there was only the plug, there was only presence, but as soon as the weight descended upon it, it became painful. I didn't mind the sensations, or the discomfort, or even pain, of course, but I was worried I would return home with the plug completely inside me.

I ran my errands with the pain in my asshole getting all the time stronger. But it was a pain I could deal with. It meant the object was at my anus, not inside of it. I could neither make up which one I liked best, walking or driving, since they both had their fascination.

When I walked the bike beside me I could feel the plug move a bit with every step between my sweaty butt cheeks and asshole. It was a very comfortable feeling, a presence that was with you constantly.

When I was on the bike, on the other hand, there wasn't anything similar. However, all my weight was on now my asshole with the steel plug in it, making the metal bite into the tender skin around the anus. Every time there was a bump on the road I could feel it in my ass.

I discussed this a bit with a virtual friend of mine, and she suggested I should get myself a silicone one for riding a bike and night time wear. In fact I could have gotten myself one today, since one of the stops on my trip was a porn shop, but I was there on another business.

The thing is, I have been for some days now considered buying myself a prostate stimulator. Considering how my libido reacts to objects or pressure inside my colon, that would be the next logical step. I compared models and their prices in the shop and almost bought myself a cheap model.

Finally, however, I decided not to give into the haste and my own horniness, and came home to order a bit better model online. Due to weekend it won't arrive until the beginning of the next week, though.

As soon as I got home and started edging again, well as to write the report you have just been reading, as well the part before it. I usually edge while writing them, which I hope shows in them. By the time I got them written I was on the verge of cumming, and my asshole was aching to get something in, as well.

Since inserting the metal plug had been so easy I decided to experiment and have a bit fun this time. I took out the big inflatable one first and begin to insert it with any prior warm-up, although with lots of lube. I was astonished to notice how far it went, even though not quite all the way.

I continued with the big cock shaped vibrator, lubed it up good and started to insert it. This time I think taking it in was easier than it had ever been. In no time the huge, twenty centimeter long thing was deep inside my ass.

This time there even wasn't much of discomfort, and neither did I have difficulties thinking straight. I turned it on and started to fuck myself with it. After a while this begun to bore me and I hobbled to my bed, put a towel on it and laid down.

I spread my legs and checked whether the vibrator was still in place. For part of me it was still hard to believe how well my asshole had become adapted to it. However, when my fingers slick from the lube met the end, only the end of it was sticking out between my butt cheeks. There it was, with no intention of coming out.

Followed a similar procedure than the one had took place during couple of nights, the only difference being there wasn't a tiny steel plug in my ass this time. I twisted it into all imaginable directions and finally started rotating it, while keeping the power on maximum.

After a while I closed my legs, wiped my hand a bit and just lay there. It was a curious feeling. There I was, laying on the bed, with the huge virbrator buried deep in me, with the power still turned on to the maximum setting.

I lay there for quite a while, examining the sensation the vibrator caused. I admit I wouldn't have minded if the vibrator had made me cum, but nothing like the sort happened. I could feel the faint buzz inside me, but I couldn't find in my the slightest arousal caused by the vibration.

Finally I decided it was time for the main attraction. I got up, removed the vibrator, lubed the inflatable plug again and started inserting it. I was simply overjoyed as it went in effortlessly. I hadn't caused any pain or discomfort, nor did it so now as I stood up.

I smiled at my reflection, feeling very pleased at myself. Sure, my heart was racing like crazy, the way it did when I had something as big inside me, and there was lube dripping from my ass, but the huge thing in me didn't feel as if it was something that didn't belong there. I felt only good, and natural.

I hobbled to my bed again and laid down. I admit at this point I had the intention of having the same kind of practice session than with the big dildo. It seems the more my asshole becomes adjusted to foreign objects, the more rational my mind becomes, so I thought this would be a good opportunity to finally test the inflating feature.

However, after a mere three or four squeezes the thing felt so huge inside me it was hard for me to think straight. Also, I knew if I planned to get anything done the next day I needed to ejaculate tonight. Therefore I grabbed my limp clit and while at the same time expanding the plug in my ass even more masturbated myself to a sissy orgasm in a matter if fifteen seconds.

Afterwards, I admit, I felt a bit disappointed at myself. I had wanted to fight the urge to cum a bit more, and the orgasm to have a bit more grace. I yanked the plug out of my ass, which didn't hurt as much as it had the previous time, which is a good thing, of course.

I had just given myself the most thorough ass ramming of my entire life, though. Therefore it was understandable the sensations I felt inside me the rest of the night were interesting to say the least. There wasn't pain, or even actual discomfort, merely... well, things happening.

At the moment it seems the time span before I become insatiably horny is about 48 hours. The thing is, this time as well, the next day went smoothly, but today I have been horny again, and it's practically impossible to keep myself from edging continuously. Then again, there are worse ways to spend your Sunday, I suppose?

9.12.2016

This time there has been a few days pause publishing in my reports. I have been active in my training, but I've felt there hasn't happened anything epic enough to make a report about. Therefore this report spans the events from several days.

I have tried very hard the past few days not to give my asshole a chance to clench up. Therefore it is my goal to be able to sleep with my steel plug inside me. I have noticed, however, it is almost impossible to actually get a good night's sleep wearing it. Sure, it's fun stretching your asshole all night long, but it usually means I either sleep the next day, or turn into a walking dead.

I was having one of these nights three days ago. I put the plug in before going to bed, but was awoken a few hours later to the discomfort it caused. I started my stretching exercises I described a few reports back. Finally I realized I was too awake, got up and went to the bathroom with my toys.

This time I decided to continue with my big vibrator, and proceed the inflatable monster only after it, in other words doing it in a different order now. For some reason this time I had some trouble getting the vibrator in even with a lot of lube, and it didn't go in quite as deep as would have wanted.

Then I proceeded to the black inflatable one. This too, proved to be more difficult I had anticipated, in fact it was harder now than the previous time. I didn't show no mercy, though and finally managed to push the monster in.

I looked myself from the bathroom mirror as I stood in front of the washbasin. My face looked so... normal, and respectable, a bit disoriented maybe, and with a hint of a smile on the lips. Despite the fact the turmoil of feelings inside me was the complete opposite.

The huge thing filled me so completely and I realized being extremely turned on. Perhaps not as turned as sitting on my computer the last time, but still. The plug inside me felt so good, so an idea occurred to me: what if I cummed? Right now, while staring myself in the eyes? After all, I had already cummed once by my free will, what would it matter if I did it again?

So, I did. All and all, however, the experience wasn't as hot as one could imagine it to be. It was all so physical, and determined somehow. After I had yanked the huge plug out, which hurt again like hell, I felt even a bit bad. I collapsed into the bed soon afterwards.

The next time I ended up cumming was in a way even more strange. This time there was a day in between, even though technically it took place during the next day. This time I was sitting in front of my computer. I felt a bit horny but I knew I should I should go and take care of number two sooner or later.

Being horny won this time, however, and I slipped in the red diamond plug, which is rapidly becoming my favourite one. A naughty virtual friend of mine was online and I soon realized I was horny. I mean, really, really horny.

I was a bit puzzled. It was almost as if I had the big plug in. Every time I fiddled a bit with my limp penis I felt a surge starting rise in my balls. Could it be that the... well, crap inside my colon was pushing my prostate just the right way?

With the encouragement of my virtual friend I decided to see what would happen if I continued fiddling with myself. So yes, I was going to cum, for the third time by my own free will. I started to give myself a series of fiddlings, pushing myself closer and closer to the edge and feeling the familiar strain in my testicles growing.

Then, as soon as I knew I was past the edge, I let go of my limp penis and let it drop on a plate I had put on the chair between my legs and balls. I felt a smallish wave of an orgasm flow through me, and something enter my penis, but nothing came out and the wave started to pass.

Part of me was surprised, part of me glad, part of me disappointed, because I knew I had just given myself a perfect ruined orgasm. I knew that if I didn't do anything I would still feel horny, as well as tense and irritated the whole next day.

Since this wasn't what I needed, I grabbed my limp penis, started masturbating again and experienced the actual orgasm. Sperm shot out of my little clit, and the waves of orgasm washed over me, this time much stronger.

I admit being a bit puzzled afterwards. I just had a decent orgasm, because of... well, a butt plug and shit in my colon?

All in I had now cummed three times in three days. It had been ages since the last one I had done it so frequently. Also, I was painfully aware, they were all orgasms I was solely responsible for. On the other hand, none of the orgasms had happened because of some sort of anal or prostate stimulation.

After the third orgasm, however it seems my libido run out of juice for a while. In fact for couple of days afterwards I felt very unsexy. All changed this morning, though. But that that will be a story for a later time...

6.12.2016

Okay, sixth part it is, then. This installment, or rather the events described in it are somewhat unusual or at least unexpected kind. The thing is, when I got up today I thought the day would be an uneventful one, since I had no great master plan in mind when it came to my anal training project.

As you know, the previous day and night I had been shall we say active, but this time I had basically fell asleep after pizza, beer and the latest episode of Westworld. As I woke up I didn't feel especially sexy.

As I was sitting at the computer having my morning edging and chatting with a virtual friend of mine, my boy pussy started to feel empty again. Therefore I slipped the red diamond plug in again, this time even using a bit of lube with it.

However, it didn't take long for me to feel the familiar feeling of number two wanting to get out, which meant I had to go to the bathroom and take the plug out. One thing led to another and I realised it would be nice to give myself a little enema again, to get myself properly empty.

This time I did it with more, caution though. Afterwards I probed my hole a bit with the red diamond plug and noticed it felt nice and loose. This gave me an inspiration and I took out my cock shaped vibrator I had managed to put in only once so far.

After all, we're talking about a male porn star size here, that's 3 to 4 cm wide and over 20 cm long. I put a lot of lube and started to insert the huge thing. First I couldn't get anything else than the tip in, but I continued, and slowly but firmly pushed the thing deeper and deeper.

At some point I turned the vibrator on. I could feel it, but for some reason the vibration doesn't seem to have a big effect on me. Finally it was inside me all the way, and before I took it out I even managed to sit down a bit with the huge thing vibrating in maximum setting.

This gave me courage and I took out the black inflatable butt plug I have been able to insert into my asshole only twice so far, and after a quite of discomfort. I admit I had been worried I wouldn't be able to do it again, thinking what took place couple of days earlier had been just good luck, or that my asshole had clenched shut during the last few days.

I put a good amount of lube on it and started to insert it. You might guess how overjoyed I was when the thing slid inside me almost effortlessly! A mere days earlier it had hurt and it been a huge effort to get it in. Now I was able to push it in my ass just like that without much obstruction.

Sure it felt big, but it wasn't nearly as uncomfortable or painful as it has been in the first or the second time. Perhaps it was thanks to the lube, or perhaps my nightly spreading exercises had  helped, as well.

I sat down in front of my computer. The plug filled me up nicely. Even though the sensation was very intense, it wasn't uncomfortable. One could even say it felt... natural somehow. I loved feeling so full.

Originally my idea had been to sit on my computer, perhaps trying to pump the plug a bit larger and even edge a bit. What followed was quite a surprise for me, and one could even say, end of an era.

At this point I have to make a small confession. Even though nothing I have told you in the past isn't untrue, there are two things I have not told you. This is because I have been unsure what  to think about them. The thing is, as a result of my experiments I have had two ejaculations this week.

They could be perhaps called ruined orgasms or edging accidents. Neither of them took place by my free will, and I wasn't even touching my limp penis when things started happening. What took place was in both cases purely anatomical. My body simply decided to go over the edge and I could do nothing to stop it, only to observe it from outside, and in horror.

The first instance took place on Thursday, when I had the nasty clothespins on my nipples for an half an hour. Sure, I had been playing myself for some time before it happened, but I had no intention to cum, and in my opinion I was miles away from an orgasm.

As you may guess, I was pretty broken up after the incident. I couldn't understand why my body had betrayed me like that. Not only it meant 2016 wouldn't be totally cum free for me the way I had hoped, it also meant the 497 days record would now remain unbroken. I had been 373 days without an ejaculation at that point.

The second incident took place two days later, after I had gotten the inflatable plug inside me the second time. I was sitting at my computer and after a relatively short amount of edging I noticed my body started to push itself over the edge, without me being able to do anything about it.

I wasn't even touching my penis at that point, but on both occasions I squeezed it hard, in the hopes of being able to stop the process. In the latter case I there was a spasm after spasm, and I felt my penis filling up with semen.

Afterwards I wasn't as broken up as I had been two days earlier. In fact I was amused and excited. Had I just found my prostate? All the stereotypical things I knew people said about men who liked to take it in the ass kept going round and round in my head. Now it seemed I was one of those men. The whole situation amused me.

Now, I was sitting at my computer again, with the plug filling me completely. I was fiddling with my penis almost absent-mindedly when I suddenly felt a surge starting up in my balls. I instantly took my hand off. What? I wasn't even masturbating myself this time!

I repeated what I had done, and the same thing happened again. This was fucking unreal. Did my body like this much the plug in my ass? I understood I could make myself cum in series of light fiddling if I wanted. I hadn't never, ever been in a situation like this.

Thoughts raced through my head. My attempt to break my record, as well as to make 2016 completely cum free for me were already in shambles. But I hadn't cummed by my own free will since November the first, 2013.

For over three years I had denied orgasms from myself. For 37 months, or 1130 days, I had kept myself denied of the thing normal men took for granted, and gotten a huge masochistic kick out of it.

During the last three years not cumming, or thinking I had no rights over my own orgasms, had become the center of my sexuality. Not cumming, or not even wanting to cum was what I did. It was what I was. Was it time to change that now? Was I actually considering that I had a right to make myself cum? Just like that?

Then again, what would I win if I just stepped back from the situation, removed the plug and continued my so-called chaste life? Considering the sad truth there was no one who was actually that interested about my chastity. Not even after I had desperately tried to find someone who would take 24/7 control over them. No one cared. No one, but me.

So I made my decision. I would do it. I would let myself cum. I would deliberately let my body to go over the edge,  and let the warm semen out. Something I hadn't done in three long years. I would fucking cum. I would cum. The thought kept going around in my head even though it was almost too big for me to comprehend.

I started to lightly fiddle my penis and immediately felt the orgasm starting to approach. I was able to take myself couple of times very close to a brink, only to stop at the last moment. Finally I decided it was time to give my testicles the relief they wanted, and continuing the light fiddling I let my body go over the edge.

As soon as I knew it couldn't be stopped, I let go and feeling the wave of orgasm wash over me I watched as my limp little penis started to ooze warm semen out, spurt after spurt, to the towel I had on the office chair I was sitting in. It looked so funny, and unreal. My little penis, cumming.

After a series of spurts I took the limp penis in my hand and started pulling it back and forth, and was able to create something I could almost call as an second orgasm. A part of me regrets now I didn't continue longer.

After I had yanked the plug out of my ass, which incidentally hurt much more than putting the thing in, I collapsed on the bed completely naked. I was disoriented but happy, even though a part of me had difficulties understanding what had just happened.

The inside of my ass hurt a bit, but not as nearly as much it had done in the previous time. Also, the sensation was more like a mere muscle ache than stinging. I knew that was a good thing. Ass throbbing, smile on my red and flushed face I let myself to drift to sleep.