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.
