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 - 20/11/2006
(self, anal, toys)

by Casey



Dear Diary,

I woke up today at half-past-seven thinking immediately of the contraption I had deviced the night before. I was so anxious to try it. I had slept naked and uncovered as usual, with the 'pussy harness' beside the bed. I didn't waste any time before lubing up the thick white plastic bottle and then my boyhole with vaseline. I made sure to reach inside my boypussy with two fingers to prepare the way for the much thicker bottle.

Then I stood the bottle under me, squatted, and began to press myself down on it. The top of the home-made dildo was blunt instead of narrowed, so it was like trying to push a log into my ass. It was very difficult and I had to push the bottle from side to side as well as pry apart my boyhole to force the device in. As it started to go in, I felt as if my ass was on fire, a similar feeling to the one you get when you are constipated with a very big, very hard piece of shit. I grimaced and relaxed my sphincters even more, acting as if I was relieving myself to help the device get in. Even once the 'dildo' penetrated me, it took a while before the full length could be pushed up my boychute.

I could feel the head pushing deep inside me, beginning to encounter resistance. By this time the dildo was almost fully inside, leaving its base right flush to my anal opening. I turned to face the mirror by the bed and spread my legs before it. There before me I could see the bottom of the bottle-dildo, a big white circle with my ass-ring straining around it. I let it hang there for a few moments, savouring the sight as my boypussy was split wide open by the unholy object, and then pushed it the last half-inch or so into me. I could see the white circle disappearing slowly under the bunching muscles of my stretched anus, and even when my asshole closed I could still catch glimpses of the white cylinder through my wrinkled opening. From the pressure inside my guts, I could tell that I had picked the right object. It had gone as far as it would inside me and my ass only barely closed behind it. It was a little disappointing to finally get confirmation that I could take only so much in my hungry pussy, but I had read stories where the bottom's insides were forcefully made to adjust to the intruding invader, so I did not lose all hope.

The thin metal wire that ran through the bottle's base and was twisted together into one piece with the loop on one end was now protruding from my bursting asshole. The wire extended for about four inches before the loop, and I took it and pulled it up firmly between my asscheeks. It covered almost the exact length of my asscrack (not surprising since I took some rough measurements last night). With the wire pulled up firmly and the bottle lodged inside me I could feel a mixture of numbing pressure inside my guts, a snug tightness up my crack and some discomfort on my ass-ring where the metal pressed into the muscle on its way up my backside. At that moment, all I could think of was fulfillment. With the loop just above my crack. I ran another piece of metal wire through it and pulled as high as I could before looping the two ends of the second wire around my waist like a belt. The length of the wire enabled me to loop it twice around my waist, with the middle pulling up at the loop forming a V up my waist if you looked at me from behind.

Pussy Harness
Wire 'tail' pulled tight up my crack

I did not try to be gentle to myself so when I pulled I really made the dildo tail bite deep into my crack. The fact that the wire was thin metal meant I could shape it anyway I wished, so after two tight loops around my waist (I made sure the metal bit considerably into my flesh) I took the remainder and ran them under my balls before fastening them tightly just under my belly button. So in effect I had a contraption that pushed a thick gut-filling dildo inside me, held the cylinder from going further in by applying constant pulling pressure on my lovehole and along my asscrack, gripped my waist snugly and at the same time pulled up at my balls at every movement. I was quite proud of myself for coming up with the name 'pussy harness'. It was a little difficult to get up to my feet, but after enjoying the feelings for a few moments I went to take my bath.

All the normal things I did during a bath become a sweet torture for me. The simple act of bending down to scoop water, of brushing my teeth and of soaping up my body became a punishment on my hole, my asslips and crack and my balls. I loved the feeling of suffering as I went through my normal morning routines, as if I was not in charge of my life but was a helpless slave kept harnessed to make sure my lovehole was properly trained for submission. I finished up, dried myself with difficulty and got dressed in formal attire, a maroon shirt with black slacks. Getting dressed was a chore but little did I suspect that putting on my socks was to be the hardest thing I ever had to do! By this time the pressure and friction of the metal wire across the rear part of my ass-ring and along my asscrack was beginning to tell, but I steeled my resolve and decided to proceed to, in such a state, drive to work.

The next 30 minutes of my life (the heavy traffic meant double the normally 15-minute drive) turned out to be the worst torture I've ever went through. I didn't expect my position in the car would apply additional pressure on the bottle and cause the wire to be pulled even more tautly against my asscrack. It felt like someone was trying to cut my ass into two parts using a blunt knife. Every bump on the road, every braking movement or changing of the gear was hellish torture, even when made in the gentlest manner possible. Any sudden braking would send jolts of fiery pain up my backside and spine, causing me to stiffen and cry out. And the heavy traffic ensured there were plenty of those moments. By the second kilometre (the full journey was about eight kilometres), my left hand was gripping the handbrake with a shaking death-grip, my right hand was trembling on the wheel and my head thrashing from side to side in agony. No matter how I tried to shift my body, the pressure never eased one jot.

I remember thinking how it was such a big mistake that I swore never to be that stupid again.

And so the journey continued, ever so slowly, while I beat my fist on the car door and writhed and whimpered within the hellish embrace of the harness.

It seemed to take forever, but finally I was parking the car (wincing and fidgeting) and preparing to leave it. Knowing I could not avoid the impending agony, I closed my eyes and made a dash of swinging my feet over and rising to a standing position. It took a few seconds to recover from the blinding flash of pain, which slowly receded into a dull throbbing around my boyhole and along my boycrack. Walking to the office, which involved crossing a street, was a downright chore, a usually simple act I that day performed with all the finesse of a swaying toddler. I had to pretend to be preoccupied with texting on my cellphone to avoid inviting suspicious looks. At least the walk was not as bad as the drive.

Greeting my office-mates with smiles and casual conversation was hard; I think at least one noticed the look of constipation on my face as he proceeded to ask me if I was ok. Despite all this, the masochist in me told me to persist, to take my seat at my cubicle and start working as normal (by this time I had lost all appetite for breakfast). As I had suspected, sitting was hard and I ended up leaning back uncomfortably with one hand braced on the seat to support my suffering bottom. I managed to keep this up for more than an hour, going even so far as to talk to a few colleagues who came over to discuss work-related issues. But the pain was getting too much and I had do to something. But before that, I had to make sure it was all worth it.

Pussy Harness
Front view of the Pussy Harness

I went to the toilet with my digital camera in my pocket. It was deserted so the flash would not be a problem. I put the camera on the flush and lowered my pants and lifted up my shirt until the harness could be displayed nicely to the camera. Using the camera's timer, I took pictures of my front and back with my pants lowered and my shirt gathered up over my belly. I could not wait to show these to my Master and tell him all about how I took my own initiatives to act on his idea (that I look for something that I could keep up my boychute all day long to train it as a proper pussy). Stripping off after taking the pictures was as difficult as putting the clothes on, but eventually I was standing there in the stall with the harness unlatched from around my balls and waist, leaving the dildo tail jutting down between my legs with the waist-piece trailing from the loop all across the floor. It felt really dirty to stand there like that. I fingered my crack and asslips to see if I was bleeding. Luckily, I wasn't, but my hole was very sore and seemed a little swollen.

Pussy Harness
Rear view of the Pussy Harness

I sat then on the toilet and proceeded to take a shit. It was as painful and as time-consuming as if I was really constipated, but after about 5 minutes the bottle broke through my tortured opening and plunked noisily down into the bowl - but it was stopped short of falling all the way by the wire I held in my hand. There was shit on it. I spent another 5 minutes trying to void my insides (it felt like I had to shit bad, but not much actually came out) before I cleaned up.

But I was not content. I had wanted to keep the dildo inside me all day and the 2 hours or so I managed so far was disappointing. So I made the decision to try it again, to re-insert the dildo into my anus. I had no lube and both my assring and the bottle was wet, so it was an almighty struggle to get it back in. The head was bad enough, but the last inch seemed to take forever to make the journey up my chute. Even then, I realised that it wasn't going to go in as far as before - something in me might have shifted a bit. The part near my perineum went in past my sphincter, but the part to my rear seemed to have jammed without entering completely. I basically had a quarter circle of bottle-base showing to the outside world. No matter how much I tensed my guts I could not get the bottle further up, so I was still in a fair amount of distress when I decided that it would have to do.

I had been taught a lesson that pulling the tail between my buttcheeks was a bad idea so this time I pulled the loop to the front, so that it ended right against my balls. With the other piece I pulled the tail tightly against my balls and then brought the waist-piece up either side of my cock and around my waist, this time forming the wide V on the front. I looped the extra length tight around my waist and tied off the end. It didn't feel as discomforting as the last method. I got dressed and returned with the camera to my cubicle.

This time I lasted only an hour. The pressure on my sphincter due to the fact that the bottle could not go in completely was immense. So was the pressure on my balls as they were squashed against my crotch (another bad decision). I returned to the toilet and stripped to take the dildo out. My previous exertions and suffering had left me weak and I was trembling all over as I tried to dislodge the thick intruder. I had to put my feet up and press them against the door-sill and wall to help maintain my focus and efforts on expelling the cylinder. As I struggled, I could not help from occasionally tugging at the wire to feel how the bottle would pull on my asshole. It would be fitting if my Master were to use this method to keep me leashed. I could imagine myself getting dragged this way and that by the dildo stuffed in my pussy like the worthless slave that I was.

I was panting hard by the time the bottle clattered into the bowl, fairly clean this time. As the bottle was pushing out, I had kept my fingers circling and feeling my asslips to see if I had injured it. My asslips were swollen and very sore but luckily I was not bleeding, not even from the part of the muscle where the metal wire pressed, either to the front or back. It was awesome to feel the lips stretching and expanding as the bottle gradually emerged from my widening boypussy, but the pain as the full cylinder emerged and exploded through my strained opening was sharp.

I cleaned up, dressed again and wrapped the wires around the bottle before depositing my 'pussy harness' in my pocket.

My boyhole lips didn't shrink down and close down completely for a while, as they remained swollen and smarting. It was almost midnight as I wrote this and there was still a fair amount of soreness on my pussy. It was a feeling I welcomed and wished would never fade away forever (even though I think it would be a couple of days at least before I put on the harness again!).

That evening, I stayed back in the office almost another hour waiting for Master to come online. But I was to be disappointed. Before I left, I sent an email to Master telling him how desperately I needed to talk to him and tell him of all that I had done.

In fact, I was so horny that when I arrived home, I lubed up the deodorant tube and my aching ass again and pushed it up my chute. It went in more easily but my ass was hurting more after all the abuse. My fingers followed the cylinder's movement as it slowly sank into me. My asslips felt sore and puffy as they closed over the thick base, just barely covering it completely. I secured the loop with the other wire to both my knees to give myself more stimulation, but it became uncomfortable so in the end I just let the loop and wire dangle from between my legs. I lied down and tried to go to sleep, but my bottom felt so full with the tube inside me and when I shifted to my sides the tube would start to push against my bladder and the pit of my stomach. I really wanted to sleep with my pussy filled like that but the discomfort was making it hard to drift off. In the end, I had to go and void my stomach. Walking to the toilet was funny with the wires dragging along behind me and tugging slightly at my boy pussy at each step, but any such humiliation are fitting for me.

The tube jetted into the toilet bowl with a loud clunk, and as before, the feeling of constipation made me screw up my face in pain. I waited a little for the urge to void my bowels to subside. I could see that not much was coming out, except for some big drops of thick yellowish-white liquid dripping into the bowl and floating in the water. After a while, still with my asshole fully relaxed and gaping open, I decided to feel up my hole and see how it was, since it felt really sore and burning. My fingers found my thick gaping lips and lightly traced their way around the mounds of soft pouting muscles, and I found that it felt really good, soothing in a way. After a few circuits around the lips I brought my fingers to my face and saw that they had strands of clear jellyish liquid on them. Hesitantly, I brought my fingers to my mouth. The liquid tasted familiar to me.

As my horny mind went into overdrive, I brought my fingers back to my pussyhole and began to really swipe around and inside it, drilling them deep into the soft folds of yielding flesh for more of my flower's nectar. I brought the thick jelly strands to my mouth and sucked greedily on my fingers, again and again. Once or twice I managed to gather so much of it that it covered my two fingers completely. It seemed to my lust-filled mind that the juice was the most tasty, most nutritional food I've ever had (although it didn't really have much taste except for a certain tanginess) and I could not get enough of it.

Finally, I waddled slowly over to the bedroom and spread my legs before the mirror. I let my ass relax again and it unclenched and flowered open easily before my eyes. Then I took two or three pictures of my gaping boycunt. With the mirror's help, I was also able to dig around for more of the juice, which I continued to suck from my fingers with relish. After maybe four or five more swipes I had finally exhausted the precious supply, but I made sure to scrape off any leftovers from around my pussy lips for a last mouthful. I felt very dirty with all the disgusting things I did, and since I was already in the bed I thought that it would be so hot to simply go to sleep without cleaning up. I could feel the stickiness on my fingers as the juices began to dry up and I was sure my swollen boycunt was going through the same. With a final lick on my fingers, I hugged my naked self contentedly and drifted off to sleep.

- Swollen pussy and abused slut, Casey -



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Diary - Part 4