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?     

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...