All standard disclaimers apply.
Introduction
The following diary entries are taken from actual entries that I had to
write for my online Master and contains actual activities that I had been
ordered to carry out for him.
Casey's Diary - 19/11/2006
(self, nipple-torture, cbt, toys)
by Casey
Dear diary,
Today I spent almost all the daylight hours inside and on my bed, naked and experimenting with my self-discipline and capacity to obey my Master at the expense of my own pleasures. Usually, for me the weekends would signal a time of free-flowing, orgiastic self-stimulation, but this time I had not been permitted to cum. I wondered if I could really do it, or if I would succumb to the temptation to relieve myself and also to lie to my Master - after all, he'd never know if I disobeyed him. I could always pretend not to have cummed.
I knew that there was no way I could actually make myself forget about the little bit of attention-demanding flesh dangling between my legs, and nor did I have any idea what to busy myself with to keep my mind preoccupied. In the end, I resolved that the day would proceed as 'normal'. I would laze around and do whatever I wanted with my body, but with one exception. I would try my damndest not to cum.
Last night I had caught sight of the container of about two dozen clothes pegs standing by the sink, so by the time I woke up this morning I already had a headful of ideas of what I could do with those. Walking around the house naked as usual, I took these to the bedroom along with my favourite tall movable mirror. I placed the mirror by the bed and as I knelt on the mattress admiring the boyish nubile body in the reflection I began to think of ways I could make the picture more attractive using the clothes pegs.
I quickly recalled that one email (in response to my earlier diary entries) asked me if I had played with my nipples the same way I had with my boypussy, to make them jut out more like a girl's or even stretched out to indecent proportions. I had doubts about the attractiveness of a set of flabby sagging nipples (that was the way the question made me picture them) but as usual the sheer depravity of the idea excited me and soon I was twisting and pulling my nipples out and away from my chest. I could pull each nub perhaps half an inch out and as one hand pulled, my other hand would fasten two of the clothes pegs onto the nipple, side by side, one on each half of the stretched out, dark-brown aureole (my nipples plus aureola are about the size of 20-cent coins). I used the pink-coloured pegs because I thought pink was a more girly colour. The pegs had viciously-toothed mouths and fairly stiff gripping power so each snapping of the jaws elicited a soft whimper from me.
The pain was considerable but I was also proud to see my nipples standing out between the clenching pegs. After a few moments I decided that the little bitch in the mirror deserved more punishment, so I took several more pegs and began arranging them in a horizontal line on either side of the two starting pegs on each nipple. The end result was that I had six pegs lining each of the undersides of my boy-pecs. The attachment of these additional pegs was even more painful than the first and I could not help moaning like a whipped dog as each peg bit into my chest-flesh. I could see my face screwing up in pain each time in the mirror and it only made me want to hurt myself more. I spent the next few minutes either kneeling or lying down on my back watching television (I have it in my room across fromt the bed), panting or moaning as small movements sent jolts of pain around my nipples and trying my best to ignore the constant throbbing otherwise. I found that in such a condition, the most painful movement would be if I stretched my arms up above my head. It was painful enough to make me cry out even if I did it slowly and for a while I revelled in the torture.
After about 10 minutes I started to remove the pegs one by one. It was true when they said removing them was just as painful as fastening them on in the first place. And if you accidentally let one snap back shut in the process of unfastening it - hell, I became very careful not to let *that* happen again. I left the first two pegs on each nipple last. The pegs left considerable depressions on my flesh, something that looked like bite marks made by 4 teeth - 2 above and 2 below, spaced apart between half-an-inch to three-quarter-inches depending on the area of flesh they mashed between their jaws. The worse were the depressions around and on my nipples - they left my nubs and the aureoles wrinkled and deformed. I played with my nipples for a bit to savour the feel of the deformations on my fingers, and then I pulled my them out again and methodically re-fastened the pegs.
The second time around I used more pegs, perhaps 10 or eleven on each breast. Apart from the original six, I fastened 3 more pegs on the outside, running vertically up the outer line of my pecs towards my armpits. I snapped two more randomly on the soft mounds of my chest. The pain was overpowering but I was proud to see my chest positively bursting with pink clothes pegs. As before I left the pegs alone for a while, this time longer than the last. Sometimes, I would gently nudge the lines of pegs downwards or upwards to see how they would pull on my snagged flesh.
Inevitably, my small cock had grown hard and the pain-pleasure was beginning to take over my body. Unable to help myself I began to jack off, using minimal hand-to-cock contact to reduce the possibility of a spontaneous orgasm. It was always a losing battle and I was starting to feel resigned to disappointing my Master when an idea crossed my mind.
I paused, took a spare peg (only the blue ones were left), snagged one half of the pincer underneath the flaring head of my (cut) cock (on the top-side), and let the jaws snap over almost half a centimeter of cockhead flesh. There wasn't any sharp pain like with the nipples, but what came through was a deep dull throbbing that kind of overshadowed the squirming in my loins. Fascinated, I fastend more pegs until I had a ring of five pegs flaring like a blue flower around the mushroom head of my hard cock. (I could not help thinking then how funny I looked, with my chest sprouting pegs and a flower of pegs on my cock to finish it off!). The dull throbbing combined and I found that, even though I continued rubbing my cock (carefully), I no longer had the same urgency to cum as before. Indeed, my cock even softened slightly until it drooped, although my fingers' attentions kept it hard for the most part.
I almost grinned with joy. It worked! I was now in no danger of disobeying my Master!
The fact that it wasn't as painful made me suspicious, though, and sure enough, I soon discovered that my fears were founded. There was no sharp pain when I attached them, but the excruciating (but thankfully short-lived) agony when I started to remove them more than made up for it. The first one made me gasp outloud. The peg-teeth that was positioned under the rim of my cockhead seemed to be stuck to the flesh somewhat, which was what made it so painful. I found that the two on the lower side of my cock, on either side of my pisshole, were the most painful to detach. Panting, I scrutinised the rim of my cockhead and found the flesh indented with the familiar bitemarks, only these ones looked deeper and redder.
Over the next hour or two, I tried all sorts of stuff with the pegs. I found that the most I could fit around my cockhead was seven (I tried to start putting one on my pisshole but wimped out when a mere half of the pressure almost made me scream outloud). I also tried different peg formations on my cock, one of which involved 10 pegs in a line between the skin just underneath my cockhead, along the underside of my cock and across the middle of my scrotum right down to the mound of flesh between my balls and my boyhole (the perineum?) with several other pegs attached randomly to my ballsack. I lied down on my back with my legs spread and my crotch sprouting pegs imagining I was being tortured by my Master. Any time I felt in danger of spurting boycum, a few pegs on the cockhead would always bring me down.
I also attached and detached the pegs on my nipples many times. Apart from that, I would attach a rope to the other end of the pegs and use it to pull my nipples up or down. It was so painful. I could also see that my aureoles were now indeed jutting out. I could not say for certain if this was solely due to the stimulation by the pegs or could have been the result of any other stimulations, but I was pleased that my nipples seemed to remain in that condition until long after (it was only the next morning that I found they had returned to their normal state). I debated whether to try going to sleep with the pegs on but I was worried of any possible long term effects so decided against it.
For the rest of that day I could not stop thinking about Master and what he would think of me once he knew all of the things I did. I hope he'd find me a very dirty and naughty slut and that he'd device even more humiliating punishments for me. But I also thought I had not done enough for Master. Then I remembered that he said he wanted me to look for another 'dildo', one that'd allow me to put the whole of it inside me. I had identified something that I could use as such, but it needed some modifications to make it work.
That night I took this plastic bottle of used roll-over deodorant - it was about 4 inches long and slightly thicker than my cock (when hard), just the right size to fit in me length-wise and push me further than normal thickness-wise - and emptied out the contents. I needed a way of ensuring that it would be possible to keep the bottle near my hole and to pull it out if needed, so using a small nail and hammer, I made two holes near the base and ran a thin metal wire through the holes. I twisted the two ends together and made a loop so that I could run another wire or rope through it. I envisioned that the loop at the end of the 'dildo' could be attached to maybe another device tied around the waist.
I was very pleased with my design and spent some time looking for a name for it. Finally I settled on 'boypussy harness', or maybe 'pussy harness' for short. I wanted to try it out that night but I was tired, so I decided to postpone it to the next day.
- Flabby-nippled slut, Casey -