27.12.2016

Welcome to "My Boy Pussy Project", part thirteen. In the two following installment I will cover the events that took place on my sissy Christmas. This one covers it since my last ejaculation and all through the following week, up until the night before the Christmas eve. Even though I wanted the blog to have a little break during the holidays, the project itself has continued and there's so much to tell you about.  

Christmas is stressful time for all of us, but I try to enjoy it as much as possible. Among other things my approach has been for several years to handle all the family responsibilities before the Christmas, so I can spend the eve just the way I want. There would be tons of stuff I could go into, but since this is a sexual blog I will try to focus only on the erotic side of my Christmas.

As you may remember I had cummed on Sunday, and the following Monday had been a rest day for me as far as my testicles were concerned. By Tuesday they were working on full steam again and I started to get increasingly horny. After all, it seems man's testicles are designed to shoot their load daily, and by the second day the constant throbbing in my balls begun again.

Originally I was supposed to be on the way to my parents on Tuesday, but ultimately I decided to postpone my trip for one day to get more stuff done. And being the anal freak I am, I couldn't resist turning some of the things into something fun.   

Among other things I managed to do the first and very hasty part of my Christmas grocery shopping with the metal plug in my ass. As you may remember, for a long time running errands while plugged has been a fantasy of mine. However, none of the attempts have been total successes since I've either been terrified the devices slip in, they have slipped out or been too painful to wear.

This time I chose my metal plug with a ball like furry end, which proved to be a good choise. Getting on a bike with it on seemed a bit extreme at first, but I didn't let it stop me. In fact I think the cycling part was what kept the plug in, even though it did bit a bit painfully the rim of my asshole.

In the local Lidl I realized the plug would stay in and not slip out and relaxed and just enjoyed the feeling. It was quite an experience to do your shopping with it in.As I have said, the sensation the metal plug creates is rather invasive, sharp and rough. It is quite impossible to forget it, as it moves left to right on every step you make.

After the second shop the sensation became increasingly painful as the metal bit deeper into the rim of my sweaty asshole. The plug itself stayed in though during my whole trio, and that was all that mattered. All I can say that was the most intense Christmas shopping I had ever done.

Afterwards as I was chatting with my virtual friend and the discussion took an interesting turn. The thing is, I had had an idea on Sunday to freeze my load, but I ditched it because the sperm I shoot out didn't look that healthy. However, for that reason I had emptied an ice tray and put the cubes to a bowl in the freezer. And every time I opened it I saw them and heard their siren song.

Why siren song, you ask? Well, as it happens. I have a long relationship with using them in ass play, all the way from childhood. Back then it had filled me with shame, as all things sexual things did. A couple of weeks earlier, as I had been giving myself that a bit too radical enema, I had slipped one in, and discovered I still liked the sensation, even more than before.

I mentioned all this to my friend, and was finally rewarded with an order to put an ice cube in my rectum. As I have told you, it is much easier for me to do things if I am ordered to, so I was very grateful to her for breaking the ice, so to speak. She likes ass play as well, even with ice cubes, so it was natural she was a very understanding.

My friend wasn't able to be online the whole time, so I had to manage on my own as well, and during the night I ended up rekindling my interest to my old hobby.  

The next day, as I was in a bus on the way to my parents I got to explain to her my fascination with the practice. First of all there is the humiliation aspect. Usually it's practical to be completely naked to do this. And let's face it, to do something as perverted as that, you will have to be a complete freak. No sane person would ever do it, right?

Then there are all the sensations. If you take a big, sharp edged ice cube straight from the freezer it's usually cold enough to make your fingers stick to it and the thought what you're about to do fills you with fear. As you bend over and put it to the lips of you asshole you can even hear the cube crackling, adding to the situation.

Then you start to push it in. First it hurts a bit, you feel the coldness and the edges pressing to the sphincter. At that point all you have to do is keep on pushing until you feel the cube start going in. You merely have to keep on pushing with your finger until you feel it going past the sphincter. Usually I keep pushing the cube even after that to make sure it goes in all the way.

And that, my faithful readers is my favourite part. The moment you feel your rectum gulping the cube up almost eagerly. That's the most intense, freaky and most wonderful part. You feel it disappear into you, as if it never existed. You know it's inside you and you're never going to get it back, nor do you wish that.

I must say I got hooked to the feeling that night. I liked it so much I ended up putting in, not one but three ice cubes in a row. I remember being almost like intoxicated as I did it. As soon as the previous one was in I started to get the next one out of the tray with shaking fingers. I just had to experience it again.

Then, there were the sensations cubes itself generated. Every time a new cube slipped inside me and I clenched my ass cheeks shut I could feel the cube starting emanating coldness. I could feel my balls shrink a bit, and I could feel my penis, even though still small as a tiny knob, desperately trying to say something to me.

I still have hard time defining what that something is. Is it "Please, wank me! Please!"? Or is it "Yes, put next one in after that one, please!"? Or perhaps "Oh, that's so cold, it hurts!"? It could be all three, even though I do admit the need to grab your clit and start pulling it back and forth is almost impossible to resist at that point. After the three cubes I felt I had to stop. Even though I knew I had wanted more.

I did remain extremely horny the next few days even though unable to continue any sort of anal training. On Wednesday morning, as I was getting rid of the morning hornyness by doing some very light fondling at my computer, I realized I was on the edge in less than a minute. That gave me quite a scare, and I decided not risk it from there on. In other words I haven't touched myself at all during the rest of the week.

The horniness continued all the time I was at my parents' place and there was times I literally had to go and curl as a ball on my bed, and try to get the constant, demanding ache in my balls to stop or even easy off a bit. The fact that there was very little to do there and that I have a pretty good imagination didn't help.

What I could do over there was to look online for new anal toys for myself, though. I have realized I am not only running out but also outgrowing my current ones. Due to my poor financial situation though I was unable to get myself anything for Christmas, but as soon as the new year comes I will get myself a new toy or two.

I may make at some point a separate post about all this later, but main question had to do with size. I wanted the toy to have room for growth, but on the other hand I didn't want to make same mistake I had done previously and get a toy that was way too big for me. However, being extremely horny didn't help in trying to be realistic.

The stay at my parents was far from an unstressful one, and after I got home on Friday I was a wreck, both mentally and physically. I did manage to finish my Christmas grocery shopping, though, and since it would have been just boring to do it any other way, I did it with my prostate toy in. Also, my asshole felt had been neglected for days.

This time I visited only the shop around the corner and made my trip on foot. All in all I was amazed how comfortable the prostate toy was to use now. Even though it was somewhat disappointing it didn't create same kind of the sensations the metal plug did.

On the other hand the sensation the prostate massager created was much less invasive. There was only a sort of presence there was something inside me. Truth to tell, it was comfortable in the degree that using it instead one of the plugs seemed almost like cheating.

Afterwards I practically collapsed on the bed, completely exhausted. However, I was happy I had now several days of to relax. All I wanted was some peace and quiet, to do things on my own, whatever it was. Little did I know what the next day had in store for me...

24.12.2016

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19.12.2016

Welcome to “My boy pussy project”, part twelve. Originally I wasn't going to make another post before Christmas, but things don’t always go the way we plan. Let it also be told that this installment contains, not only a lot of anal training, but also a description of me cumming. If you don’t like the idea, proceed with caution. If not, and you want to find out in how I got to spill my sissy seed, read on. Sunday was supposed to be the day I got stuff done. However, I was so excited by my earlier breakthroughs I ended up playing with my boy pussy most of the active hours of my day. It just sort of happened. I won’t bore you with as detailed description this time, and quite frankly I don’t even remember in what order everything happened. Originally my idea was merely to check whether I could get the pink monster straight in with a little lube. That didn't happen, but I did notice it wouldn't have needed that much help. It almost went in, just like that, to my totally unprepared boy pussy. So I dug out my cock shaped vibrator, lubed it up good and in no time had it deep inside my ass. It seemed so easy now, and it was amusing to think that it wasn't that long ago getting it in was such an accomplishment for me. After I had rammed the vibrator in and out of my boy pussy for quite a while it was child’s play to slip the pink monster in. Afterwards it was time for the inflatable plug and then… well, if you read my last report you know what happened next. As I was already wrapping things up my female virtual friend came on-line and I got to tell her about the breakthrough I had made. She was naturally very pleased to hear about it as well, and was eager to read the whole report from the previous day. I asked whether she would be amused if I put the pink one back in, and in no time I was sitting in front of the computer with the big jello plug inside me. It felt so good. It was so big it felt it was filling me completely. I couldn't understand how I could have lived without this sensation as long as I had. It also turned out I made a record of sorts. My friend had stuff to do while she was chatting with me and couldn't be on-line all the time, and so it happened that I had the huge thing inside me a whole hour. I tried my best to avoid my ass from shutting in around the plug, and therefore making taking out needlessly painful. Therefore I tried to work out with the plug as much as I could. For example I tried to pull it out a bit, enjoyed the pain as my asshole muscles were pulled forward, but stopped before to plug was actually out. I also noticed that if you turned the base part sideways, the ass cheeks pulled the plug out a bit, making all sorts of practices possible. For example doing walking movements turned out rather interesting, since every step I made shifted the plugs position inside my ass. If I leaned forward towards a kitchen counter using my arms, and then started to thrust my hips slowly forward the feeling inside my ass became extremely intense. As I finally took the plug out I knew it would hurt, but I was determined to enjoy that pain. The plug was in my ass so that I could have fun, not to torture myself. Therefore, as I was pulling it out and the part that hurt most came, I stopped the plug there, and savoured the pain. Then I pulled it back in, then back out, until I was fucking myself in the place it hurt the most. I wanted to love that pain. At some point my virtual friend came back on-line and said she had read my earlier report and liked it. So much in fact it had made her wet. As matter of fact, so wet she’d had to, to quote her, “take care of it” the same time I had been training my asshole. At first I was unable to believe what I had just heard. It seemed too fantastic to be true. She had masturbated and orgasmed, because something I had written had made her wet? That was not only the highest compliment I could have ever hope to get, but it was also extremely arousing. When my friend had originally gave me the cum ban she had set the limit till Sunday, which was now. However, the damage my clit had endured had made me doubt whether that was realistic. A bit by bit it had healed and was now more or less in masturbating condition. I realized now I was horny beyond belief. Maybe it had to do with all the things I had done that day, maybe it was the light fiddling I have given to my limp penis, maybe it was the six days worth of cum in my testicles, or maybe it was what I had just heard. I told my friend how horny I was, and was given an order to cum for her. Because that was what I needed, a command to cum, not a permission. I wanted my orgasm to be something that wasn't up to me do decide. I didn't want freedom to cum. I wanted my orgasms to be controlled. And now I had a command to fulfill. Heart racing I set my wanking mirror the right way and sat down in my office chair facing it. I was completely naked and shivering a bit, either from the fact I was horny, or that it was rather chilly in my apartment. I even put on my distant vision glasses so I wouldn't miss anything from what I was going to see. I spread my legs and looked for a moment at my naked, hairless body. Even though I know I'm not bad to look at, I have body image issues. For years it was hard for me to see my own reflection in the mirror, and watching myself naked has been even more hard for me. Seeing myself like this was humiliating beyond belief. Then again, feeling humiliated made me extremely horny.

With my hands shaking in excitement I started to fiddle my limp penis. I watched the reflection of my face as the edge become closer. I thought they looked funny. More than anything they looked the face of a boy who didn't know what was happening. There was such disorientation, puzzlement surprise, even a hint of panic. It would have been even more amusing, it I hadn't been going out of mind at the same time. Gradually I picked up the pace and fiddled my limp penis faster. I looked at myself starting to breath more rapidly. The look on my face became even more alarmed as the orgasm approached. Finally I felt myself going over the edge. Looking at my own astonished face, deep into the eyes, I let go of my limp penis.
I spasmed in my office chair as I felt the waves of a glorious orgasm wash over me, and kept my gaze in my eyes. I grimaced as I felt bits of clogged up sperm coming out of my penis, and finally I had to even help it a bit with my hand. This was familiar to me, and usually happened when I didn't cum in several days. Immediately after the orgasm I was concerned because I was now without a ban again. I didn't want to have freedom to cum whenever I wished. I wanted my orgasms to be rare, special and cherished. I wanted them to mean something, like this one had.

However, my friend was extremely nice and gave me a new ban. First she set the ban till Thursday, which would have been in four days. However, when I told her the exact numbers on my counter as I cummed, 6 days, 4 hours and 21 minutes, she moved the date till Sunday. Naturally I couldn't have been more grateful. In other words, the next time there will have to be a full week on the counter before I have any hope to cum, which will be way past Christmas eve. Naturally I hope it will be even a bit longer than that, but we will have to see. Like I said, it’s not up to me. My friend did hint that the next ban may be even longer. I’m so excited now. This is the best Christmas present I could hope for.

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.