31.5.2017

There is a Facebook page I follow that has a habit of posting questions on its wall. I try to answer them whenever I feel I have something to contribute to the matter. A few days ago there was a question: "Does it turn you on if you're being watched while masturbating?" 

Since that is a question I think I could write a book on, I gave a detailed and truthful answer. I knew, as I sat down to write, the answer would be a long one, but it surprised even me how lengthy it ultimately became. I'm posting my answer here, as well. I hope you like it.

Does the idea of being watched while I masturbate turn me on? The answer is yes, immensely so. I have spent hours and hours of looking for erotica with a scenario like that, or CFNM porn, with male protagonist having to masturbate for female audience. Unfortunately there isn't a lot of it around.

As far as reality goes, I have always masturbated a lot and I have been lucky enough to perform it in front of a woman a few times in my life. Unfortunately however, it seems many women find that very distasteful and have said that to me. I suspect that has something to do with gender roles. However, lately I have started to regret I don't have anyone in my life to masturbate in front of, or have had so little chances to do it observed during my life.

Masturbating while being watched is a big turn-on for me. I think it's because masturbating is the most pathetic, sad and disgusting thing a male can do sexually, and having to do it with other person watching is humiliating beyond belief, which is a huge fetish for me.

What adds to the situation in my case is also the fact I have a very small penis, which thanks to medical reasons doesn't get hard even when I masturbate. In other words, if I pulled it while being observed, it would look very funny indeed, and it would be very humiliating for me.

I have had for many years a fantasy of living with a woman, who I would have a special arrangement with. I could masturbate as much I wanted, but only while being observed by her. I would have to ask permission for it, and had to do it so that she would be in the same room and could see me at all times if she wanted.

Naturally I would have to ask permission for an orgasm as I got closer, and she would have all the right in the world to deny it for me. She wouldn't have to give me any reason for denying me, if she didn't feel like it, but it would be a good motivation for me to be the best possible boyfriend I can. "I just don't feel like it" would be a perfectly reasonable answer.

In a ultimate fantasy setting I would have to do it with several women present, and with their permission. I would be naked, of course, while all of them were clothed. There could be men present as well, and I suppose it would be interesting for them to observe me. At least it would be humiliating for me having to wank my limp dick in front of real men.

The women or men wouldn't have to find what I do erotic or arousing. In fact it would be hard for me to imagine anything I could do to be erotic or arousing to anyone. The most I can hope for is it to be at least amusing for the audience.

The people present could watch me, ask me questions and generally be total control of me, but I wouldn't mind if they ignored me completely, had conversations between each other or go on about their normal business as I go about my disgusting one.

I think there's an element of humiliation there, as well, in my masturbation meaning so little to anyone but me. Naturally I would have to have a permission from someone present before I was allowed to ejaculate, of course. It wouldn't be at all certain I would get one, however.

The same applies to the girlfriend arrangement I described earlier, as well. She would by no means to be obliged to actually watch me if she didn't feel like it. She could give me a permission to masturbate, but she could tell me to stand or kneel somewhere she wouldn't have to see me.

If she wasn't into watching her boyfriend beat his tiny thing, she could continue whatever she was doing as I approached her with my request: read, watch tv, work on her computer and so on. Only as I approached an ejaculation I would have a permission to speak and ask permission for it.

Afterwards I'd have to thank her for the permission, as well as for the chance to masturbate, of course.

But, as most of you know, all that is pure fantasy for me, and I have no one in my life to for all the things I just described. Therefore, I think, the fact that I sometimes like to masturbate in front of a full length mirror is my way of trying to substitute for it.

After all, since I don't have no one to humiliate myself in front of, the only thing there is for me to do is to humiliate myself. Watching myself as I masturbate my limp dick, and trying to imagine what someone would think looking at it.

People have often asked me why don't I look for on-line partners then? Truth to tell, I'm too cautious to do that. What would I do if, after five minutes of ecstasy, the girl's pimp appeared on screen and demanded money for not putting on-line the video they just filmed? When it comes to sex industry, webcam business is a way too hazardous place for gullible wankers like me.

And quite frankly, I'm too much of a romantic for not wanting the person in question to be someone I have a connection with. That me being naked and humiliating myself in front of her would mean something. But's it's a small niche, fetish wise, to to watch and be amused by a man pulling his small limp penis. As well as very challenging one to have, if the idea is to approach a woman romantically.

In other words, yes. I do find the idea very arousing, but at the same time it is something I have very little chances of getting to experience. 

16.5.2017

Morning horniness is a curious thing. No amount of erotic stimulation can compete with the erotic arousal you have when you wake up, hard or semi hard. When you're in that sweet semi-conscious state unsure what's true and what's not.

As you all know, I try very hard not to lose my libido even though I'm in cum ban. Therefore I try to masturbate as much as I can during the daytime. I take great pride doing it, since it is, after all what I do best, and the times I pull my limp dick are the ones I truly feel being alive.

I have lately noticed that weather seems to have an effect on my masturbation. At the moment we're having a chilly spring, and it has even snowed several times during this April. Some weeks ago there were warm spring days, and my edging immediately doubled. As soon as the cloudy and chilly weather returned, it diminished drastically.

But like I said, I have done it as much as humanly possible, and it seems I have indeed been succesful keeping my libido alive. Several nights in a row I have had erotic dreams, and I have woken up extremely horny.

I would gladly tell you about my dreams, if I had any idea what takes place in them. My dreams are generally very hazy jumble of things, and unfortunately that applies to the erotic ones as well. As I wake up all I can remember is flash images, without any kind of idea who I had been, and what I had been doing with whom in the dream.

In any case, couple of mornings now I have been turned on enough to hump my cover in my semi-conscious state. I know that doesn't sound much, but they have been the most erotic experiences I've had in ages. Usually at that point I don't have an erection anymore, only this... puffed feeling on my penis. I sleep nude to encourage my morning erection and erotic dreams, so usually there's nothing between my penis and the quilt I am grabbing on.

What took place this morning a mere moments ago, must be the most arousing series of events so far. During the past couple of mornings I haven't dared to hump the quilt very long, since I seem to have this alarm in my head, that makes me stop what I am doing before it starts to feel too good, often way in advance. Preventing myself from cumming, no matter the circumstances, seems to have become a second nature for me.

This morning, however, I took a more decisive approach, and continued humping longer than previously. With due fairness, I have to say my movements, or "thrusts", weren't that big, and I think someone looking at me wouldn't necessarily have even noticed them. To me, however, it felt almost as if I had been fucking something.

First I made a series of fives, then ten, and finally twenty-five. At that point I had to stop because I felt I was getting too close to orgasm. I just stayed there, horny as hell, listened the sound of my heart that was beating like hell, and enjoyed the aching, desperate throbbing in my testicles. They wanted so bad to get all that sperm out. I didn't remember when they had been that alive.

As soon as I dared, I continued and did another twenty-five, then fifty. At that point, having done a full hundred, I had stop for a while. I was so turned on, my aching balls were begging for a release and it all seemed... so wonderfully humiliating.

I considered my options. I started to become more and more awake, and I was able to think more coherently now. I even considered the possibility of letting myself to cum, or at least trying to. To feel the approaching orgasm, and letting it engulf and wash over me. I would actually feel sperm ooze out of my flaccid penis. Most likely there wouldn't be more than a few drops, and by anyone else's standards it would be called a ruined orgasm, but it would feel so, so good for. me.

After all, I had already been...what, over seventy days since my last orgasm. Wouldn't there be time for another one, at some point? And I would be doing it by humping a quilt, with my flaccid penis, for crying out loud. What a humiliating story that would make to tell on my blog. Since I knew I would have to describe this experience there, with every little humiliating detail.

But on the other hand, I knew how much better story it would make, if I could describe all this, and not having to end it by telling how I let myself to cum. To be able to tell you I didn't cum, even though I wanted it desperately. Also, I knew, if I let myself cum it would mean I would have to start counting from zero again, without even having to reach triple digits. Did I really want that? Was I ready for it?

At some point, as I was thinking all of this I had continued humping the quilt in series of twenty-fives and fifties. I even considered how humiliating story it would make if I actually decided I would let myself cum, but ultimately were unable to do so, after all? Somewhere around 300 I lost count, but continued humping the quilt. All in all I think I got somewhere between 500 and 600, before the waking world finally dragged me from my sweet slumber.

As soon as I had gotten up I turned my computer on, sat down still naked and started writing. I wanted to get it all down, when I was still fresh in my memory. Naturally I have been pulling my limp penis the whole time, and I feel drops of sweat rolling down on my naked body. All I can think of what somebody would think if he or she saw me now.

However, even though this is highly enjoyable, and I seem unable to stop, it's not even close to what I experienced earlier...

8.5.2017

This blog update contains very little description of sexual activities or anything very graphic. It does, however, contain a lot of material about how I see male chastity and how it relates to my situation. It is, in fact the longest piece I've written about the practice, ideology and philosophy behind denying yourself orgasms.

This is also the first update on my blog for quite a while. There hasn't been any posts here since January, and some of you may have been wondering why the sudden silence.

I think I never made a conscious decision to put the blog on hold. Due to several reasons there was a pause, and the longer it became, the more difficult it was to start blogging again. You know how it goes. After all, I knew I would have to somehow recap or explain why my once very active blog fell silent all of a sudden.

I guess I could have continued reporting on this blog my sexual life, or rather lack of it, on daily basis. How often I masturbated, what did I put in my rectum and how it felt, or whether I had managed not to cum. But it seemed to me I didn't have anything new to tell you.

I have also been a bit depressed the past few months. Very often in these kind of situations one doesn't notice it at first. This happened to me, as well, and it took a while for me to realize how stuck my life has been for several months now.

The main reason for me feeling blue, I think, has been my loneliness. That too, took a while for me to understand, to admit how lonely I truly am. Being now single there is no one I can share my sexuality with, and if that sexuality has to do with chastity, it can be very lonely indeed.

I have tried to relieve my loneliness, and looked for like minded company on-line. During the past half a year or so I have had several virtual acquaintances I have been able to share my erotic side, but for some reason or the other, none of those relationships have lasted very long.

My boy pussy project, at least when it comes to active anal training and stretching my asshole, has been on hold for a while now. There is one practical reason why that is, namely the lack of new toys. I realized already way back in Christmas I'm in dire need of bigger butt plugs. However, my financial situation hasn't allowed any purchases.

I am happy to say, however, that there's hasn't been setbacks in the project either. I have regularly tested my boy pussy, and made sure I can still fit even my biggest toy there. However, even though there hasn't been setbacks, there hasn't been progress either. And therefore, nothing to report.

What about the chastity part then, you may ask? Let's get some statistics.

As you may or may not remember, I started cumming again in the beginning of last December, after 370 days of denial. It happened again more or less by accident. This time however, I decided to stop chastity altogether. What the heck, I thought. What do I lose if I start cumming again? Three years is enough time to be in cum denial, right?

One could say at that point I took myself a project of teaching my body to cum again, and more importantly, trying to make my brain understand it is quite okay to cum. To ejaculate like a normal man. Well, almost like a normal man.

I ejaculated all in all 11 times during the last month of 2016, a year that had been completely cumless for me at that point. I had planned to make it completely cumless, period, just like 2014 had been. That, however, didn't happen.

I continued my selfish orgasming in 2017, and ejaculated 20 times in January and February. The longest time between ejaculations was 10 days, but there was times I ejaculated on three consecutive days, sometimes even twice a day.

That's 31 times just in three months. So, one could say my cumming was rather "reckless" at that point, at least in the light of my recent past. In comparison, there had been only 8 orgasms in the previous three years. Or, more accurately, in 37 months between November the first 2013 and December the first 2016.

None of these 8 orgasms hadn't even happened by my own choice. Either they were ruined orgasms, very unpleasant edging accidents or done under the supervision and permission by my girlfriend. Sometimes all three at the same time. In other words, in December 2016 I had my first voluntary, totally unsupervised, full orgasm in three years.

So yes, there was a lot of adjusting to do. In my defense I can say that thanks to my virtual acquaintances only a handful of those 31 ejaculations took place without a permission to do it. That's right. No matter how hard I tried, I felt I still needed a permission to cum.

The longer it went on, the more I realized it was hard for me to shake the feeling that as I ejaculated I was doing something I shouldn't do. That cumming on my own and unsupervised was just wrong, immoral and unnatural. I wanted so bad for someone to be in charge of my orgasms.

Still, all through the January and February I lived a life that could almost be called that of a "normal cummer". The orgasms I had felt great, of course. But the fact remained that I still felt, deed inside me, that what I was doing wasn't right. That all that pleasure felt wrong. That whether I cum or not, when, how, where and how often, was something that shouldn't be left for me to decide. Because I wasn't trustworthy enough for that kind of responsibility.

And not only that. I felt my orgasms were losing meaning. I still kept record of them, just as I had done when they were few and far between. This meant writing down up the exact time of each and every ejaculation by the minute, what had I been doing before it, sometimes even the amount of time I had managed to get on the counter.

However, the more frequent my orgasms became, the less meaning they seemed to have. And the less interest I had writing down the details of my ejaculation. Every time someone said there should be less orgasms for me I could hear and feel the siren song of chastity calling out to me. How right it would be to limit my orgasms drastically.

Things led to another, and I am happy to announce I'm back in chastity again. At the moment it's been 69 days since my last ejaculation, and counting. And quite frankly, I couldn't be happier. I understand now how right this is, and how wrong it was for me to start ejaculating again. The one I had on 28th of February, 10:45 AM (EEST) is at the moment the last ejaculation I've had.

I know this is nothing compared to 374 or 497 days, but after a my cum spree I'm extremely glad I have managed to keep my testicles denied this long, once again. In fact, after I had been without an orgasms for a couple of weeks and I realized I wouldn't be cumming for quite a while, I felt this... well, feeling of tranquillity setting in. Like I said, it's just feels right for me not to cum.

Sounds weird? Well, I guess it does. However, I've had to think a lot about my own sexuality in the past couple of months. After all, I had managed to get rid of a sexual practice many people would consider abnormal, twisted and unhealthy. 69 days? That's crazy. Why do I want to start denying myself again like this? Where's the fun in not having any pleasure? Don't I miss orgasming?

My own guess is it may very well be that all the time I have been in chastity in the course of last three years have made me chastisexual for good. Yes, that is a word I have made up, chastisexual: someone who gets sexual enjoyment from being forbidden to cum.

I still do edge regularly, partly to keep my libido alive and testosterone levels high, but also to torment myself. Even though I don't get to experience orgasms, I want to be near one, so close the fight not to cum is a real one. I don't want to forget how easy it would be.

What is interesting is also the fact how much more I like masturbating than actual cumming.
I've always loved masturbating, and I was a regular cummer for the most of my life. A day without an orgasm was a day missed, I used to think.

However, only after I discovered long term denial I realized how good it actually feels to be able to pull your penis without having to "worry" about cumming. It feels completely different when you know you have no intention of letting yourself cum.

It is somewhat ironical, but I'm pretty sure I have masturbated more after I found chastity play, not less.

Because when you're not denying yourself, you masturbate to cum. When you are, you masturbate to masturbate. If you're not denying yourself, ultimately you reach a point when the lure of an orgasm becomes greater than the pleasure you get from masturbating. If you're in chastity, all you have is the act of pulling your penis. There is no set ending point. Therefore, when it comes to how long an edging session can take, only sky is the limit.

For me the thing I seek when I masturbate is the desperation. It's like a flame I want kindle. The longer I am without an orgasm the bigger danger there is for that flame to die out. On the other hand not letting oneself cum is the reason the flame of desperation exists in the first place. Edging is what keeps it alive, and the more I edge, the stronger the flame becomes.

In a way, knowing it is me who keeps my testicles denied of something most people take for granted, feeling the ache within them, and understanding I do it merely for the pleasure of seeing the day count going higher, is exactly the thing that helps me not to cum.

Because I know, that if I did let myself cum, it would feel great for 10 to 15 seconds, after which I would feel empty and hollow and meaningless again. All those weeks and months would have been for nothing, and for what? Those few short moments of ecstasy?

Empty, hollow and meaningless are also the words I have used when I've had to explain the way I live my so-called sexual life for someone not into it. More precisely, I have used it to describe the orgasms I had in those three months. I could still cum whenever I want, several times a day if I liked. But like I say, they wouldn't mean anything.

Every time I start to edge, however, it does. Every pull on my little penis has a meaning. It means I will soon be in great discomfort, and desperate to cum. But I know I won't, and that gives it meaning. One could argument the same could also be said about normal cumming. However, to me it there's much more meaning in torment than there is in pleasure, somehow.

It may seem odd to a person who isn't into this lifestyle, but cumming and being in control of your own orgasms is so... well, troublesome and stressful, as well. There's all these things you have to consider. Especially if you've once experienced the denied life, you cannot help but feel all the responsibility on your shoulders as you masturbate.

Should I cum or not? How many has there been this week already? Is it too much? How should I do it? Should there be toys involved or not? Where should I do it? What should I be thinking or watching when I let myself go over the edge? Should I ruin it or not? At some point you just don't care anymore, and cumming becomes a routine. Sad, predictable routine. And that happened to me earlier this year.

When you're a chastisexual, there's none of that. You can masturbate freely without having to worry about cumming, because you won't. You just won't cum, period. No matter how long you pull your penis, you won't cum. Knowing that gives you such a piece of mind.

Also, by denying yourself orgasms you avoid the post-orgasm blues, as well. There's no feeling of regret, or that you've lost something. You merely continue your life, carrying your horniness and desperation to cum with you, like a dear friend who is always beside you, or on your mind.

The way I feel it, a deliberate orgasm is simply not an option for me anymore. At least if I'm not given permission to, or ordered to cum. I tried the life of a normal cummer, but I understand now that isn't for me anymore. There are people who would most likely disagree with me, but denying myself a normal ejaculation cycle for several years now, has given me so much more than taken away from me.

Still, I have doubts, sometimes. Like I said, I have done a lot of soul searching when it comes to my sexuality in the past few months.

As you all know, I’m impotent. It's something that's a part of me, and a fact I have accepted long ago. The only time my penis gets hard is at mornings, almost as if to remind me it could do it, if it wanted to. So, not only is my penis really small, it really is completely useless when it comes to the fairer sex.

Now, if I was a real man with a normal sexual history I suppose this would have been a nightmare for me. I would have sought medical aid for it long ago, and continued my sex life by having sex with women. But as we all know, I am not.

Instead of feeling ashamed, however, I don’t only refrain from sexual encounters, I actually feel good for being impotent. Not only have I accepted it, I actually take perverse pleasure for my penis and my sex life being this sad and pathetic. Or, more precisely, because I'm this sad and pathetic, I don't deserve a sex life, or even orgasms, that are, after all, for real men, not wimps like me.

Now, I do know there are other ways to please a woman, ways I am pretty good at, in fact. However, my recent relationship history makes it very hard, if not impossible for me to seek out another one. I have been very fortunate in the past, when it comes to my partners being so understanding about my limp dick. But I understand that cannot continue indefinitely. So I jerk off and edge, alone.

What this had led me to think is this. Could this recluse masturbator life of mine be seen, not only sad, but also… well, selfish somehow? I have a tongue and fingers I could please a woman with, but I choose not to, just because I’m such a gutless wimp.

Does that fact, that even though I edge myself sore but don't cum, make the whole situation more “acceptable”, or does it merely make it worse? Is it a good thing I keep myself experiencing something as normal and wonderful as orgasms, does it serve me right not to cum, or is what I do simply idiotic and selfish?

Someone also recently pointed out that these kind of thoughts may very well stem from my need to serve. After all, that is what every submissive wants to do. So, in that respect what I do could be seen as selfish. I don't pleasure anyone with my edging.

One could say that is the one thing I do miss. To have someone I would be allowed to please and give pleasure to. To be allowed to share my denial with someone. To have someone teasing me and enjoying my discomfort.

I do believe, that if a woman into chastity play walked into my life now and gave me a chance of pleasuring her I would have no objection to giving away my right to cum as long as I live.

6.1.2017

Welcome to "My Boy Pussy Project", part sixteen. This installment of the series is a bit unusual one, since it contains very little anal play and even less denial, even though the events described in it are somewhat interesting from the chastity point of view. In fact one could say I have just had the four most bizarre days of my life. 

I will try to tell everything in order. The events in this part start more or less where the previous one left off. I had cummed after twelve full days of chastity, albeit after some rather extreme teasing. I had collapsed on my bed and fell asleep totally exhausted and drained.  One would imagine it would be a while before I get horny again.

Well, as it happens this was not the case. This is, in fact where the bizarre part starts. I woke up around eight in the morning, mere three hours I had collapsed on my bed. I immediately noticed I felt oddly nervous and jittery. I realized I felt extremely horny, almost as if had been working on full steam. The feeling was very strong and quite frankly, very unpleasant.

I felt I had to do something about it, and fortunately I had a chance for it, as well. The thing is, at one point during our recent session my friend had mentioned that just to get my pipes cleaned up properly I would have to cum the next day as well. And technically speaking, this was the next day.

So, for the second time in mere few hours I walked naked to my wanking mirror, which had now become an integral part of my masturbation process. I dropped to my knees, took hold of my limp penis and in less than thirty seconds had managed to shoot my load. Maybe now I could have a few days of peace and quiet down there, I thought.

I would have liked to be able to inform my friend what had taken place, but since the day in question was the new year's eve there was no chance for it. In fact it wasn't until late afternoon the next day we were both on-line at the same time. My friend seemed merely pleased to hear about my horny morning.

However, even before we begun our conversation I realized I had been way too optimistic hoping I would have at least couple of days of not being constantly horny. It didn't take long for me to be as aroused I had been the previous morning. I had to admit this to my friend, even though I was ashamed to do so.

My friend seemed amused and said in that case I should take care of it. She even suggested I put a plug  in to help me get started, but I assured her I was horny enough as it was. My friend ordered me to masturbate, and I must say doing it in the "old fashioned" way did feel very good. After all, it had been almost couple of weeks since the last time.

As we talked I got the impression my friend was in a bit of hurry and I did know she had a full day ahead of her. Part of me would have wanted to prolong it, while at the same time the idea of my wanting to get rid of me to be able to concentrate on something actually important turned me on as well. I shot my load in a few minutes while watching myself in the mirror. 

Now, I thought, my testicles had to be empty enough, surely? Well, as it happens, they weren't. You may imagine my disappointment and shock when just a mere hours later, around nine or ten the same evening, I felt again the uneasy feeling within my testicles. 

What was happening to me? There had been a time not that long ago I had been able to go months without an orgasm. The least I had expected was to have one "peaceful" day after an orgasm. Now, it seemed even an orgasm a day wasn't enough to my greedy testicles. I felt like being a slave to them, and being punished if I didn't instantly give them the release they wanted.

This time, however, I had no way of doing anything to it. I had no one to give me the permission now, so I had simply to fight it. If it hadn't been my silly moral code I think would have cummed at least thee times in one 24 hour cycle that day.

All in all I must say it's been a while I have experienced anything that insane. That evening and the following night were pure hell for me. The smallest erotic thought or a visual image made my testicles practically throb and it was hard to think nothing but cumming.

I even tried edging just a bit after seeing one extremely erotic clip, just to check whether the feeling was real. However, it took less than ten or fifteen seconds for me to reach the edge, and I had to stop. In other words, it wasn't only in my head. I was on the verge of cumming into my pants.

During the next day the feeling became gradually less intense and was finally something I could call the "normal" level of desperate horniness, usual for the second day of chastity. I was constantly moderately aroused, yes, but it was something I could handle.

I didn't contact my friend that day until late in the evening since I didn't want it to look as if I was begging a permission for yet another orgasm. My friend seemed to be sorry for me, almost as if had been her fault my testicles were about to burst. 

After hearing about my situation my friend suggested could try putting something in. According to my friend it sometimes helped her in a similar situation, to get one's mind off the hornyness. I did as she had suggested, since I knew I wouldn't have anything to lose. Also, it had been several days now I hadn't had anything inside me.

I chose my metal plug and put it in. I did it completely dry, since I wanted to check whether the several days of inactivity had had any effect, and fortunately it hadn't. As I was sitting in my chair and gently rocking myself back and forth I realized my friend had been right. Both the sensations being created in my anus and the ones in the testicles were intense, but very different from each other.

However, the longer I chatted with my friend with the plug in my ass, the more these feelings combined and soon I realized I was horny again. My testicles, it seemed, had decided they wanted to shoot their load and I was their mindless puppet. 

My friend seemed to feel pity towards me and said she would grant me another orgasm, but it would have a price. I would have to do it the way I had done it three nights ago, with clothespins on my nipples and testicles. This was a small price to pay, in my opinion. 

As I was putting the six pins on I knew I could be only making my situation worse this way. What guarantee did I have whether the ejaculation had any lasting effect? What if the horniness returned, this time as intense it had been during the previous night? What if I was now doomed to ejaculate once in a few hours, or to suffer the consequences?

This time I had put the ones on testicles first, since I knew how much the bigger ones on the nipples would hurt. As I put the bigger ones on I felt my heart starting to race again, and almost uncontrollable urge to start masturbating came over me. I restrained myself, though, since I knew it wasn't time for it just yet.

After I asked my friend for the next instructions I was rewarded with a simple request, to upsize the plug in my ass. The request took my by complete surprise. I already had the pins on my nipples, which hurt now like hell, and the next step I thought would have been my orgasm. I didn't hesitate though, and in a less than a minute I was in my bathroom lubing the pink plug.

I understood perfectly well my friend's intention. Going straight from the small metal plug to the pink one meant she wanted it to hurt. Knowing this, I started to insert it into my rectum. My asshole felt tight as I tried the plug in and out a few times. 

However, knowing my friend intended this to hurt I didn't want to show my asshole mercy. With few determined pushes I managed to ram the huge thing in. This time I almost howled out loud, and breathed heavily, taking hold of the wash basin in front of me. It had been ages my pink plug had hurt that much.

I hobbled back to my computer and informed my friend about all of this. which seemed to amuse her. At this point I also noticed thinking straight started to become more and more difficult. I wanted to cum, but the sensations coming from all over my body were fighting for my attention.

At some point I suggested my friend it would be interesting if I were made to cum not by fiddling, but in the "old fashioned" way, by actually masturbating. The reason being it would be much more difficult for me like that. After all, I knew how to make myself cum by fiddling, and become almost too good in it.

By normal masturbation cumming would be, in not impossible, but at least much more difficult with the pins on my testicles. Naturally, my friend liked the idea. She also ordered me to add four pins to my testicles to make it even more hard. I complied eagerly and soon had ten pink and light green clothespins attached to my balls.  

Since my friend seemed to like the idea of me cumming in front of the mirror I suggested her I could take this time, not my office chair but a dinner table style chair with a straight back in front of the mirror. The reason being that this would make it easier to spread my legs wider as I masturbated.

My friend liked the idea and gave me an order to cum. In matter of less than minute I was sitting again in front of my wanking mirror. Even though I knew masturbating would be more difficult with the pins on, I must admit I was surprised to discover just how difficult it turned out to be. 

Not only was my limp penis so tiny it was hard for me to get a good hold of it because of all the pins on my balls, pulling it also hurt quite a lot as the pins danced and pulled painfully on my testicles as I masturbated. In order to cum I had pull my penis fast, and the faster I pulled it, the more the pins hurt.

All in all I think it must have taken me a full minute to be able to make myself cum, which is a lot longer than any of the previous occasions. This gave me good time to examine my face during the rather painful masturbation, and how the approaching orgasm affected it.

Taking everything off after the orgasm was once again rather humiliating experience, but this time I knew to prepare for it. Still, as I did it, I found it hard to understand what made me do things like this to myself.

That was my fourth orgasm in a matter of as many days, and so far also the last one. A mere few hours afterwards I felt becoming horny again, and even though I ended up edging a little bit and thinking how great it would feel to cum again, I managed to resist the temptation. There has been couple of times I've been tempted after that one, as well. 

As I marked the first complete cum free day in my calendar I felt incredibly proud of myself. At the time I am writing this it's already almost two full days since my last orgasm. It is somewhat odd to see that as an accomplishment after staying hundreds of days in chastity.

Because even though cumming is fun, enough is enough. Just like some people need to drop meat out of their regimen, of fat or alcohol, or go on a low-carb diet for a while to feel better, I need to wean myself for orgasms again for the same reason.

So far it seems to be working, even though I am still constantly horny and I feel my balls are ready explode any minute. The slightest erotic stimulus makes my testicles throb, including writing the last two reports.

Also, during the first night my newfound chastity caused me to have a rather steamy dream. In the dream I wasn't doing more than masturbating nude on all fours on my apartment floor, until at the last moment I realized what I was doing and stopped.

It seems my body and my mind would like me to orgasm once a day, just like it once did, perhaps even more than that. Unfortunately at the moment it is something it will not get.

4.1.2016

Happy new year, and welcome to "My Boy Pussy Project", part fifteen. The next two installments of my series will cover events in my naughty life since Christmas eve. This one in particular includes not only a fair amount of chastity and denial, but also a lot of anal training. Hold on to your privates, it's going to be quite a ride.  

As you may or may not remember, the last time I cummed, was a few days before Christmas, after six days of chastity. Like I told in the part twelve, my kind friend had not only allowed, but also graciously commanded me to do it, in front of my wanking mirror.

The next time, however, she said I would have to do a full week denied before I had any hope to cum again. Naturally I was more than eager to fulfill her wish. In fact I felt it was the best present I could have, having to spend my Christmas spent insatiably horny.

As usual, the first day of chastity was easy, and I got once again to experience what was it like not being horny. By the second day however, the old feeling returned and by the third day I was constantly aroused. 

As the end of the week approached I admit becoming even a bit greedy. I liked my horniness, and didn't want it to stop. Therefore I didn't contact my friend when the time came, and neither did she. After all, it was the time of the holidays and undoubtedly she had more important things in her mind than my orgasms.

In those few days I had a lot of time to think how my mind works when it comes to chastity. I realized I had a need for my orgasms to "mean" something, to be special, a culmination for something. Not just a thing I do on my own, after I have passed certain time limit.

I understood how much I enjoy thinking about my orgasms are not in my control, something I can have any say to. And most definitely I don't want them to be something I can so on my own. They can take place even several times a day, once a day or a month apart, but I don't want it to be my decision.

On the same time I did understand I wouldn't be right for me to start another incredibly long chastity period. I knew I could slip into one so easily, but that would be just selfish, in my opinion. I did need to be made to cum now and then, but I wanted my orgasm to be controlled.

When I finally spoke with my friend she was at first about to make me cum immediately, but I persuaded her to give me a few chaste days more. Last time I had cummed there was six days on the counter. Wouldn't it be wonderfully symmetric if there was twelve days this time?

My friend agreed to it and seemed to like the idea as well, doubling seemed logical after all. Besides, by that time it even wasn't that far in the future. At the time of our conversation there was already over 9 days, 1 hour and 28 minutes on the counter, which meant there would be only two full cumless days for me to enjoy anymore.

Also, I knew the day my counter would hit twelve days would be Friday the 30th of December, which was completely empty in my calendar.

On the way to the big day I managed to have one nice training session, as well. In retrospect it was good thing I did. After all, it took place in Wednesday and by that time I hadn't done anything with my boy pussy since Christmas eve. By Friday there would have been almost a week it had been totally neglected.

I hadn't planned it though, and I have my friend to thank for getting me started. Knowing my fondness to ice cubes she suggested one night I stuffed six ice cubes into my ass. Since it was several days since the last time, this proved to be a rather demanding task. Besides, all previous times my boy pussy had been properly stretched, lubed and relaxed by the time we got to ice cubes.

I had to make several attempts even to get one in and the sharp edges hurt much more this time. In fact it was very close I asked my friend a permission to warm the ass up first a bit. However, I thought, what point is there for me to have a sweet friend who gives me cruel, unexpected and humiliating commands, if I start begging for mercy as soon as it becomes tough? 

Also, I found it amazing how much more humiliating it all felt again, almost as if my mind had forgotten this was normal for me now. As I started stuffing the cubes into my rectum, my brains were yelling: "Stop! What are you doing? Things are supposed to come OUT of there! STOP!" However, I continued since I had an order to carry out, no matter what my brains or asshole had to say about it.

After my friend had to go off-line I continued on my own and ended up having quite a thorough training session. All in all I was surprised how much closed up, so to speak, my boy pussy had become since the Christmas eve, in a matter of mere few days. 

As I was putting the pink butt plug in, I noticed it was somewhat hard to get it in, but once I managed, it merely felt extremely good. As I was sitting down in front of computer with it inside me I felt more full I had in ages, not to mention extremely horny. But like I said, there wasn't pain, just the feeling of being wonderfully full.

During my several hours long session I was again amazed how adaptable one's sphincter can be. After I had fucked myself with the pink plug for a while I moved on to inflatable one. When I finally put the pink one in again I hardly felt it and even took a small nap wearing it. Most likely I broke my previous two hour record, but unfortunately I didn't look at the watch this time.

By Friday I started to feel very giddy. My friend had agreed to be on-line to supervise my orgasm, and all during the day I was excited like a kid on a Christmas eve. There would be a lot of details to go through but I will try to spare you most of them. After all, this instalment will be long enough as it is.

An interesting little detail I do want to mention though is that before we started, I made a short trip to the 24/7 service station near me to get some groceries. However, my ass seems to be so well adjusted to wearing the plug, it all went so well it felt like cheating. It wasn't about to slip out at any point and in fact on my way home I even ended making little experiments. 

I noticed if I "tighten up" my ass cheeks while I walk, almost as if I tried "suck" the plug in, it created a nice and tight sensation. However, as soon as I relaxed my ass muscles it become even more fun, as I felt the plug starting to move left and right again. 

I even considered how it would feel to jog while wearing one, and started to consider again buying those pink running shoes I never managed to get last summer.

After I had gotten home I realized it was almost the time, and my friend was on-line, as well. Before we started properly, however, I wanted to be totally clean, so I showered myself and gave myself a nice enema. I also wanted to make sure I was completely clean and therefore reamed my asshole a bit with my vibrator. 

I also managed to do what I had fantasized about a long time now, that is setting the vibrator up so that I could "fuck" it by moving my hips up and down. The towel I had put on the toilet seat helped it to stay upright this time, and even though the procedure was a bit tricky, it was the closest I had ever got taking something up my ass, so to speak. It felt very slutty, and extremely gay.

My friend wanted to start our little session with the vibrator as well, so in a little while I had it inside my rectum again. Combining it with sitting on your chair and trying to have a conversation on chat proved to be somewhat challenging though. The whole procedure became rather technical and most of my concentration went to the keeping the thing in.

My friend's wish was that I would be horny, but since this wasn't the case,  we had to think of something else. I tried different kind of techniques, among other things I lifting my other foot on the chair and then rotating the vibrator in large round motions inside my rectum while at the same time watching myself from the wanking mirror.

The one that became my favorite though included me bending a bit forward while standing up. I would then take a good hold of the end of the vibrator with my left hand, and as good hold of the other cheek with my right one holding a small towel in it to provide better grip.

I would then start to stretch my ass cheeks as far as they would go, holding them like that a minute or so, and then switching hands. As I did this I walked around in my apartment, feeling the air on the rim of my anus, and the vibrator on full power inside me. Needless to say that felt amazing. I wanted my ass to be as open and as stretched as possible.

After a while my ass started to become a bit sore, and I was ordered to put the pink one in. This time I decided to try something new. I took the vibrator out, but instead of lubing the pink pulg first, I wanted to try whether I could put it in dry, only with the old lube that already was inside my anus.

This turned out surprisingly easy, even though it did require a little more work. It seems my stretching exercises had been effective. I felt wonderfully full again and as I sat down in my computer chair I realized I was becoming very horny very rapidly. In other words, something my friend wanted.

The plug felt incredibly good inside me and this time I didn't even need to thrust my hips back and forth to make myself to feel the plug moving inside me. Merely the plug inside me made me incredibly horny. As I was browsing my Tumblr I realized if I played with my clit I could most likely make myself cum under 30 seconds, despite the fact I hadn't touched it the whole time.

Even though my friend didn't want me to cum just yet either, she wanted to see what would happen I if did touch myself. Finally she had to order me to wank myself a bit, just for few strokes. I did as I was told and was surprised how odd it felt. Almost as if my body had forgotten in a mere week what it felt like being masturbated.

To postpone my orgasm even more I suggested my friend whether I should take the clothespins out, even though I knew I would regret it a few minutes later. My friend was glad I reminded her, since she had totally forgotten the best part, like she put it. I got an order to put the two nasty ones on my nipples and the lighter ones on my testicles. 

With my heart racing and hands shaking I prepared my nipples first a bit by pinching them and making them stand up. I was nervous, since knew in a few short moments it would hurt beyond belief. Then, hands shaking almost uncontrollably I put the pins on.

I closed my eyes, leaned back in my chair hear beating like crazy and breathed deeply. They hurt so much it was almost impossible not to start masturbating that instant. As you may have already understood I am a total pain slut, and the pain in the nipples is one of the most intense ones I know. I felt almost as if I was losing my mind. 

I resisted the urge to masturbate, though, and my friend had no intention of letting me cum just yet, either. She wanted to make me squirm for her first a while. Also, I still had to put clothespins on my testicles, as well.

My wanted me to put six of them on. Unlike the nasty ones, that hurt the most the moment they're put on, the lighter ones hardly feel at first when they're on your testicles, but as time goes by the pain increases very gradually. Therefore it was important I wasn't let to cum too soon.

At this point my recollections on what happened start to become rather hazy. Among other things I remember asking whether I could adjust the position of the nasty pins to make them hurt even more. Naturally my friend agreed. 

I also remember begging after a while for a permission to add some pins, and was rewarded with a request to put another six on my testicles. This time it was more tricky finding room for them and I realized masturbating in the regular way would be now impossible or at least very difficult.

As I fumbled with the pins and made my limp penis move from side to side, I also remember feeling the familiar stirring in my testicles. I was afraid I would make myself cum accidentally, but fortunately that did not happen.

The time of making me to cum was approaching, though. After a little bit of negotiation we agreed it would be best if I moved my office chair in front of the wanking chair, since this way I could concentrate on my orgasm, and be able watch myself closely at the same time.

Hands shaking and heart racing I moved the chair and sat down. It's hard to describe what I went through my head as I watched my reflection. I had even positioned my desk light so that it was above me in a way I had no option but to see every inch on myself in its hard light.

There I was, totally naked, sitting in my chair legs spread wide, testicles hanging heavy and full of pink clothespins, two larger pins on my nipples, face red and disoriented, eyes glazed. My little clit, surrounded by the brightly colored clothespins, was still totally limp, however, even though I knew my testicles were ready to shoot their load any minute.

Finally I couldn't resist anymore and started to fiddle my limp penis, the way my friend had told me to. The pins on my testicles rattled, fasted and faster as my orgasm approached. I looked myself in the face, that reflected confusion and anxiety, more that anything else. My mouth was open and the expression on my face become even more intense as my orgasm grew closer. 

I started to fiddle my penis faster and lifted my other hand first to my chest, and then to the other pin. Wanting to feel make the experience even more intense I pinched it and felt the sweet pain surge through me. Then I did it with other, and then the first one. I breathed in and out faster and faster. Needless to say I was beyond all rational thought at that point.  

Finally,  feeling myself going over the edge I let go and felt cum starting to come out of my limp penis. My testicles released their load, spurt after spurt as I watched my reflection in the eyes. It was hard to understand how such an incredible feeling could create such a silly expression on my face.

It didn't take more than half a minute or so, however, for the post-orgasm blues to hit me. Everything that had been incredibly hot before the orgasm, suddenly filled me with shame. I removed everything and felt myself such a freak.

My friend assured me I wasn't one, however, and after a few minutes I was able to put myself together. I thanked my friend, and collapsed into my bed, feeling completely drained, totally exhausted and sore all over.

28.12.2016

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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