Wednesday, December 28, 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?     

Tuesday, December 27, 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...

Saturday, December 24, 2016


Like the faithful readers of my blog know, there is an adult page on Facebook that regularly posts sexually related questions for its followers. I usually answer them if I have anything to say on the matter. I also have a habit of periodically publish my answers on my blog, usually around some major annual celebration. After Halloween Question and Answer special and The May Day Question and Answer special, Chaste Diary is proud to present the third installment. Since it's Christmas, this one is called "The Blue Balls Question and Answer special".

What is the first body part on a woman you are attracted to?

My apologies if I sound all deep and intellectual, but it's the eyes. No two questions about it, always have. After that, maybe hair. I notice things like breasts and backside usually as the last thing.

Do you wear cologne?

I don't. No aftershave lotion either. The musky scent they all have has always seemed too manly for me. In my opinion it's just one of those things that are meant for real men, not me.

Could you lick a penis lollipop in public?

Sure, why wouldn't I? In fact I like to amuse make my friends with things like that. They already say there is something obscene in the way I lick salt off a Pringles, so I think a penis lollipop would be an instant hit as well.

Have you ever told a kinky secret to someone and then worry after if they would tell others?

I have told them to people and then secretly hoping they would tell others. Who in turn would tell about me to a few others and... well, you get the picture. I have a fetish of getting caught, I just don't have to guts to come out of the closet as the complete freak I am.

Have you ever been reluctant or intimidated to try a something kinky only to find out once you tried it you absolutely loved it?

Being dressed up as a female and wearing makeup, or using ruby red nail polish on your fingers and toes count? Or anal training for that matter?

If you could be magically transported to your number one sexual fantasy, it woud be...

Being a nude blindfolded cunnilingus slave of a sorority party lasting for hours. That's been my fantasy for such a long time.

Worst sexual idea you ever had?

Intercourse. Every time I've tried it, the result has been a disaster. In each case for a different reason, believe it or not. I still don't get what the big deal about it is supposed to be.

If you could fuck as much as you wanted and anyone you wanted for a year, but to get there you would have to be locked in chastity for a year first,  would you do it?

For someone who has been almost 500 days without cumming and who feels he has no business of sticking his little boy clit anywhere, that is a somewhat difficult question to answer, don't you think?

If there was a reality television show made about your masturbation habits what would the title of it be?

I don't think there would be any sense to name it, because it would be a very, very, very short series.

If you were told your dick would never be inside a vagina again, what would you say?

I would look the person straight into the eyes silently for a while, and then say: "...and?"

If you could fuck anyone you wanted, but it only lasted for one minute, or you could fuck only one person for as long as you wanted, which would you choose?

Well, quite frankly, I would want anyone to be able fuck me as long as they wanted

If the woman of my dreams said she would fuck you, but only if you are in stockings, panties and heels, what would you say?

I would like her to clarify it really is she who will be fucking me, not the other way around.

If you could take a pill to make your dick ten inches long, or a pill to be rich but with a two inch dick, which would you choose?

Quite frankly, with a penis like mine, the latter is a win-win scenario. Especially if it got hard, unlike my little wiener.

If you could have any size penis you wanted how many inches would you want?

About the size of a clitoris, I think. That would reflect me the best.

If you could see any woman in the world fully naked who would she be?

An honest answer? Me. Myself, as a fully naked woman.

Whats the first thing that comes to your mind when you hear the phrase pussy whipped?


If the woman of your dreams said she will let you fuck her for thirty minutes if you eat four loads of your own cum in front of her, would you do it?

I am not made for fucking anyone, but if the woman of my dreams agreed to fuck with another woman in front of me instead, I would be immediately interested. Cumming is okay, as long as it pleases the other person. If in this case both of them wanted to see me eat four loads of my cum, naturally I would.

Have you ever been with a women older than you by lets say ten years? Was it hot?

I have to say no to this one. But I have been with a woman that was 24 years younger than me. I was 41, and she was 17. And yes, it was hot.

I know how it sounds, but over here it is perfectly legal. Also, to tell the truth, she was the more experienced, more sophisticated and more confident one of us two. I felt like a teenage boy next to her. It lasted only three months, but they were quite a three months. I still see her occasionally, and I feel my knees giving in every time.

If a past lover showed up at your door and told you they had never forgotten you and wanted one more roll in the hay before going away would you do it regardless of your relationship status at the time?

Considering my sexual history I find that kind of situation extremely unlikely. However, since I'm nice and all I would contact my current one and ask for her opinion or consent. If I had one, that is. She'd be more than welcome to join or observe if she liked, as well. Or to bring a friend. The more the merrier.

Have you ever been busted with a boner?

Numerous times. Back in my teenage years when my cock still worked I remember several longer car trips with my family during which I dozed off in the back seat. Dozing off has always caused erections for me, and it was somewhat difficult to sneak back in to the house trying to cover a raging hard-on I had under my light blue jeans and that just wouldn't go down... It's been ages I've had that problem. Unfortunately.

What advice do you have or would you give to your younger self about masturbating?

Try finding someone to do it in front of. It's much more fun that way. Don't wait too long, because that thing of yours won't work forever. I know girls seem distant, unreachable and scary to you now, but they can be a lot of fun too. So give it a try and make a little effort. Girls don't bite. Well, some of them do, but that can be fun as well.

Have you ever felt guilt after masturbating?

Almost every time. It hits me, as I think it does to most men like a ton of bricks a mere moments after the feeling of glorious ejaculation has passed. Everything feels erotic before the orgasm, but afterwards the realization of the disgusting thing or things you have once again done hits you. 

If I've been alone at the time I've just wanted to clean things up, pull up my trousers and pretend it never happened. That it wasn't me who did it. If there's been someone involved, on a chat for example it's even worse. After the ecstasy fades away you understand what you have done and you're overcome with such shame. It's even worse if it's someone you know in real life. 

If I masturbate in front of a woman it's a bit easier. Before the ejaculation happens the more dirty the situation feels the better. Afterwards you feel so hollow, as well as ashamed of what you have done. But if the other person has ordered me to cum and assures the she is pleased, or that what I did looked at least amusing, the guilt is easier to bear. 

What is your experience with so called ruined orgasms?

I love ruined orgasms. I seldom get hard, but due to my long periods of chastity it has been possible to bring me to the edge and over it by light teasing. I love the feeling I get when I come closer and closer to the edge, my heart racing like mad.
Back in the day when my girlfriend made them to me, I usually liked to give her an advance warning when I got too close, so she could stop, watch me cool down and then start again. When I got to experience a good, unsatisfying and frustrating ruined orgasm it felt simply divine.

Usually I let my girlfriend to tease me and bring me closer and closer, and then, just after the point I knew my body was beyond the point of no return, I would grab her wrist and make her stop. 
I would then have no option but to experience the wave of orgasm starting to approach, only to wither away in a very unsatisfying manner even before it had a chance to begin.

Some occasions only a drop or two of clear liquid escaped my penis, making my girlfriend giggle. 
Afterwards I usually felt uneasy and nervous. My brain had had an orgasmic reaction, and so had my testicles, in a way, but my mind felt even more frustrated it had been before my so called cum. 

Quite recently, as I've had to start experimenting on my own again I have noticed that possible due to my past experiences and long periods of total chastity, even ruined orgasms feel extremely good. Despite the fact I remember it would have been impossible idea for me not to continue masturbating to the end. 

Lately I have been able to give myself excellent ruined orgasms that have been mind-blowing. There have been times I've been able to watch, almost like an outsider, as my limp penis spurts it's load on my lap, weak and lifeless. Those instances have been both physically and emotionally very rewarding, much more so than so called normal masturbation.

Why do you think some submissive males like the idea of having their balls damaged or destroyed?

Well, they are the symbol of manhood, aren't they? There is a saying "to have balls" which means to have courage, or strength, or guts to do something. And since many submissive males get a kick out of, or they think they are failures as men, in a traditional sense at least, naturally the idea of their testicles damaged or destroyed feels very good, natural, fitting even. 

Also, it's the place where the nasty male seed is being produced and stored. The male are prisoners of constantly wanting to get rid of it, and wanting to get laid. Much of the problems men have in their lives is caused by that need. After years, sometimes decades of such slavery, the idea of getting them properly damaged must be a very tempting one for a submissive male.

Finish this thought. The last kinky thought I had was _____ about ____

The last kinky thought I had was this morning about anal training and erotic teasing. I imagined what it would be like to have a woman in my life doing all the things I have done to myself lately. Finally I would have a huge butt plug in my ass, and she's told me to sit in my office chair, well knowing that will make me so horny I could ejaculate from a slightest touch. To prevent any "accidents" though she would shackle my hands behind my back, gag me, then get naked and start masturbating herself in a chair in front of me. Occasionally she would take a glimpse of my small, flaccid penis and smile wickedly at me, knowing very well how horny and frustrated I am, and taking great pleasure of my torment.

How's that for a fantasy to wake up to?

Monday, December 19, 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.

Saturday, December 17, 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...

Friday, December 16, 2016


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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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