Friday, December 9, 2016

9.12.2016

This time there has been a few days pause publishing in my reports. I have been active in my training, but I've felt there hasn't happened anything epic enough to make a report about. Therefore this report spans the events from several days.
I have tried very hard the past few days not to give my asshole a chance to clench up. Therefore it is my goal to be able to sleep with my steel plug inside me. I have noticed, however, it is almost impossible to actually get a good night's sleep wearing it. Sure, it's fun stretching your asshole all night long, but it usually means I either sleep the next day, or turn into a walking dead.
I was having one of these nights three days ago. I put the plug in before going to bed, but was awoken a few hours later to the discomfort it caused. I started my stretching exercises I described a few reports back. Finally I realized I was too awake, got up and went to the bathroom with my toys.
This time I decided to continue with my big vibrator, and proceed the inflatable monster only after it, in other words doing it in a different order now. For some reason this time I had some trouble getting the vibrator in even with a lot of lube, and it didn't go in quite as deep as would have wanted.
Then I proceeded to the black inflatable one. This too, proved to be more difficult I had anticipated, in fact it was harder now than the previous time. I didn't show no mercy, though and finally managed to push the monster in.
I looked myself from the bathroom mirror as I stood in front of the washbasin. My face looked so... normal, and respectable, a bit disoriented maybe, and with a hint of a smile on the lips. Despite the fact the turmoil of feelings inside me was the complete opposite.
The huge thing filled me so completely and I realized being extremely turned on. Perhaps not as turned as sitting on my computer the last time, but still. The plug inside me felt so good, so an idea occurred to me: what if I cummed? Right now, while staring myself in the eyes? After all, I had already cummed once by my free will, what would it matter if I did it again?
So, I did. All and all, however, the experience wasn't as hot as one could imagine it to be. It was all so physical, and determined somehow. After I had yanked the huge plug out, which hurt again like hell, I felt even a bit bad. I collapsed into the bed soon afterwards.
The next time I ended up cumming was in a way even more strange. This time there was a day in between, even though technically it took place during the next day. This time I was sitting in front of my computer. I felt a bit horny but I knew I should I should go and take care of number two sooner or later.
Being horny won this time, however, and I slipped in the red diamond plug, which is rapidly becoming my favourite one. A naughty virtual friend of mine was online and I soon realized I was horny. I mean, really, really horny.
I was a bit puzzled. It was almost as if I had the big plug in. Every time I fiddled a bit with my limp penis I felt a surge starting rise in my balls. Could it be that the... well, crap inside my colon was pushing my prostate just the right way?
With the encouragement of my virtual friend I decided to see what would happen if I continued fiddling with myself. So yes, I was going to cum, for the third time by my own free will. I started to give myself a series of fiddlings, pushing myself closer and closer to the edge and feeling the familiar strain in my testicles growing.
Then, as soon as I knew I was past the edge, I let go of my limp penis and let it drop on a plate I had put on the chair between my legs and balls. I felt a smallish wave of an orgasm flow through me, and something enter my penis, but nothing came out and the wave started to pass.
Part of me was surprised, part of me glad, part of me disappointed, because I knew I had just given myself a perfect ruined orgasm. I knew that if I didn't do anything I would still feel horny, as well as tense and irritated the whole next day.
Since this wasn't what I needed, I grabbed my limp penis, started masturbating again and experienced the actual orgasm. Sperm shot out of my little clit, and the waves of orgasm washed over me, this time much stronger.
I admit being a bit puzzled afterwards. I just had a decent orgasm, because of... well, a butt plug and shit in my colon?
All in I had now cummed three times in three days. It had been ages since the last one I had done it so frequently. Also, I was painfully aware, they were all orgasms I was solely responsible for. On the other hand, none of the orgasms had happened because of some sort of anal or prostate stimulation.
After the third orgasm, however it seems my libido run out of juice for a while. In fact for couple of days afterwards I felt very unsexy. All changed this morning, though. But that that will be a story for a later time...

Tuesday, December 6, 2016

6.12.2016

Okay, sixth part it is, then. This installment, or rather the events described in it are somewhat unusual or at least unexpected kind. The thing is, when I got up today I thought the day would be an uneventful one, since I had no great master plan in mind when it came to my anal training project.
As you know, the previous day and night I had been shall we say active, but this time I had basically fell asleep after pizza, beer and the latest episode of Westworld. As I woke up I didn't feel especially sexy.
As I was sitting at the computer having my morning edging and chatting with a virtual friend of mine, my boy pussy started to feel empty again. Therefore I slipped the red diamond plug in again, this time even using a bit of lube with it.
However, it didn't take long for me to feel the familiar feeling of number two wanting to get out, which meant I had to go to the bathroom and take the plug out. One thing led to another and I realised it would be nice to give myself a little enema again, to get myself properly empty.
This time I did it with more, caution though. Afterwards I probed my hole a bit with the red diamond plug and noticed it felt nice and loose. This gave me an inspiration and I took out my cock shaped vibrator I had managed to put in only once so far.
After all, we're talking about a male porn star size here, that's 3 to 4 cm wide and over 20 cm long. I put a lot of lube and started to insert the huge thing. First I couldn't get anything else than the tip in, but I continued, and slowly but firmly pushed the thing deeper and deeper.
At some point I turned the vibrator on. I could feel it, but for some reason the vibration doesn't seem to have a big effect on me. Finally it was inside me all the way, and before I took it out I even managed to sit down a bit with the huge thing vibrating in maximum setting.
This gave me courage and I took out the black inflatable butt plug I have been able to insert into my asshole only twice so far, and after a quite of discomfort. I admit I had been worried I wouldn't be able to do it again, thinking what took place couple of days earlier had been just good luck, or that my asshole had clenched shut during the last few days.
I put a good amount of lube on it and started to insert it. You might guess how overjoyed I was when the thing slid inside me almost effortlessly! A mere days earlier it had hurt and it been a huge effort to get it in. Now I was able to push it in my ass just like that without much obstruction.
Sure it felt big, but it wasn't nearly as uncomfortable or painful as it has been in the first or the second time. Perhaps it was thanks to the lube, or perhaps my nightly spreading exercises had  helped, as well.
I sat down in front of my computer. The plug filled me up nicely. Even though the sensation was very intense, it wasn't uncomfortable. One could even say it felt... natural somehow. I loved feeling so full.
Originally my idea had been to sit on my computer, perhaps trying to pump the plug a bit larger and even edge a bit. What followed was quite a surprise for me, and one could even say, end of an era.
At this point I have to make a small confession. Even though nothing I have told you in the past isn't untrue, there are two things I have not told you. This is because I have been unsure what  to think about them. The thing is, as a result of my experiments I have had two ejaculations this week.
They could be perhaps called ruined orgasms or edging accidents. Neither of them took place by my free will, and I wasn't even touching my limp penis when things started happening. What took place was in both cases purely anatomical. My body simply decided to go over the edge and I could do nothing to stop it, only to observe it from outside, and in horror.
The first instance took place on Thursday, when I had the nasty clothespins on my nipples for an half an hour. Sure, I had been playing myself for some time before it happened, but I had no intention to cum, and in my opinion I was miles away from an orgasm.
As you may guess, I was pretty broken up after the incident. I couldn't understand why my body had betrayed me like that. Not only it meant 2016 wouldn't be totally cum free for me the way I had hoped, it also meant the 497 days record would now remain unbroken. I had been 373 days without an ejaculation at that point.
The second incident took place two days later, after I had gotten the inflatable plug inside me the second time. I was sitting at my computer and after a relatively short amount of edging I noticed my body started to push itself over the edge, without me being able to do anything about it.
I wasn't even touching my penis at that point, but on both occasions I squeezed it hard, in the hopes of being able to stop the process. In the latter case I there was a spasm after spasm, and I felt my penis filling up with semen.
Afterwards I wasn't as broken up as I had been two days earlier. In fact I was amused and excited. Had I just found my prostate? All the stereotypical things I knew people said about men who liked to take it in the ass kept going round and round in my head. Now it seemed I was one of those men. The whole situation amused me.
Now, I was sitting at my computer again, with the plug filling me completely. I was fiddling with my penis almost absent-mindedly when I suddenly felt a surge starting up in my balls. I instantly took my hand off. What? I wasn't even masturbating myself this time!
I repeated what I had done, and the same thing happened again. This was fucking unreal. Did my body like this much the plug in my ass? I understood I could make myself cum in series of light fiddling if I wanted. I hadn't never, ever been in a situation like this.
Thoughts raced through my head. My attempt to break my record, as well as to make 2016 completely cum free for me were already in shambles. But I hadn't cummed by my own free will since November the first, 2013.
For over three years I had denied orgasms from myself. For 37 months, or 1130 days, I had kept myself denied of the thing normal men took for granted, and gotten a huge masochistic kick out of it.
During the last three years not cumming, or thinking I had no rights over my own orgasms, had become the center of my sexuality. Not cumming, or not even wanting to cum was what I did. It was what I was. Was it time to change that now? Was I actually considering that I had a right to make myself cum? Just like that?
Then again, what would I win if I just stepped back from the situation, removed the plug and continued my so-called chaste life? Considering the sad truth there was no one who was actually that interested about my chastity. Not even after I had desperately tried to find someone who would take 24/7 control over them. No one cared. No one, but me.

So I made my decision. I would do it. I would let myself cum. I would deliberately let my body to go over the edge,  and let the warm semen out. Something I hadn't done in three long years. I would fucking cum. I would cum. The thought kept going around in my head even though it was almost too big for me to comprehend.
I started to lightly fiddle my penis and immediately felt the orgasm starting to approach. I was able to take myself couple of times very close to a brink, only to stop at the last moment. Finally I decided it was time to give my testicles the relief they wanted, and continuing the light fiddling I let my body go over the edge.
As soon as I knew it couldn't be stopped, I let go and feeling the wave of orgasm wash over me I watched as my limp little penis started to ooze warm semen out, spurt after spurt, to the towel I had on the office chair I was sitting in. It looked so funny, and unreal. My little penis, cumming.
After a series of spurts I took the limp penis in my hand and started pulling it back and forth, and was able to create something I could almost call as an second orgasm. A part of me regrets now I didn't continue longer.
After I had yanked the plug out of my ass, which incidentally hurt much more than putting the thing in, I collapsed on the bed completely naked. I was disoriented but happy, even though a part of me had difficulties understanding what had just happened.
The inside of my ass hurt a bit, but not as nearly as much it had done in the previous time. Also, the sensation was more like a mere muscle ache than stinging. I knew that was a good thing. Ass throbbing, smile on my red and flushed face I let myself to drift to sleep.

Sunday, December 4, 2016

4.6.2016

This is the fifth installment of my little series. As you can see, this time there was little pause before writing the next part, since I thought it would be a good idea to let my asshole recuperate for a while.  
At the end of a previous part I asked you whether I should try putting the inflatable monster again. Well, as it turned out, I was too much of an anal slut not to try it.
This time I had a bit more determination and after much less time than previously I was able to push the monster all the way in. I must say I was very pleased with myself as I stood up, even proud, as I felt the thing filling me so completely. At the same time I did acknowledge it was simply huge. Really, really huge.  
Saturday was a rest day for my boy pussy. Or at least when it came to the inflatable monster. It seems I have become so accustomed of having something in my ass I felt something was missing when I was doing my morning edging in front of my computer.
Therefore I got my red diamond plug and slipped it in. It felt so good being able to put it in just like that, completely dry, without much of a fuss. It was, in a way, as big procedure as putting an earring on would be for a woman in a similar situation.

As I spread my ass cheeks and let my weight descend on it I could feel the steel plug going in all the way, so that the diamond part reached the mouth of my asshole. This had become the most natural thing to do for me. Almost as if it belonged there.
When I was going to bed that night (in other words, last night) I decided it was high time I tried whether I could sleep with the plug in. I wanted to give my asshole time to heal, but I didn't want it to clench shut, either. Me being extremely sleepy that night helped, as well.
The night was restless, that I have to admit. I did, however, manage to get several hours of sleep. This was also the first time I have slept with a object in my asshole. At five in the morning however I was awoken by a sensation of pressure at my asshole.
The plug was firmly in its place but the pressure was evident. As it turned out, it was merely number two wanting to get out. As soon as got that one taken care of I cleaned myself up, put more lube on the plug and slipped it in again, with the intention of continuing my interrupted sleep.
That proved to be more difficult than I had anticipated. I was way too awake now, and even though I was still tired, the sensation at my asshole was so intense it was hard for me to relax. Therefore I started to examine a bit how the fluffy plug in my ass felt.
At first I was very cautious, and merely tapped the end a bit, or tried to twist it a bit in my ass. Bit by bit, however, I became more courageous and bold. I lay on my side and started pulling the plug to the side a bit, gradually creating a sort of rotating motion I could feel deep inside my asshole. Pretty soon I was moaning and gasping in the darkness. It may be my imagination, but the more I twisted the steel plug, the more movement there seemed to be.

I did this numerous times on my either side, as I lay in the darkness and tried to fall back asleep. Finally I got on my back, spread my legs and started to do the same in that position. That felt... incredibly divine. Not only was it extremely slutty and feminine, it allowed the plug most movement.
I did this for a long time. First right, bending the plug forcefully while at the same time spreading the left ass cheek to the other side. Then I altered the direction, and spread myself the other way. Then up, then down.

Pretty soon I was moaning aloud like a woman, spread my legs as far apart as they would go, and twisted the red fluffy thing sticking out from my ass to every direction. I loved the feeling of being so wonderfully… open.
In a way it was handy that by this time most of the lube I had put in had been absorbed to my colon. This way the plug did not so much slide in and out than pulled and twisted the sphincter around it. My aim was, of course, to widen it with this technique.
Couple of times I reached with my fingers inside the anus and tried to figure out how deep the plug was. As I was doing this is really felt as if I had pussy I was fingering. That too made me feel very good. Not only I had a clit, but also a pussy now, something I had always wanted.
Finally my movements became so forceful I could feel the steel plug move a bit in relation to the skin around it. I let it move numerous times to the opening, and then pushed it back in as far as it would go, only to start doing it again, to another direction. I realized I loved the pushing in part. It felt so good and so natural.
When I couldn't take it anymore, I pushed the plug forcefully to the other side, while stretching the other cheek as well, and let the plug move out bit by bit. I let it slide to the bed sheet, and merely pant in the darkness.
After I got my breathing back I got up and decided I wanted to get all the details written down when they were still fresh in my memory. In other words, all the time afterwards I have been sitting here writing. And pulling my limp little penis, of course.

Oh my. Look at what I have managed to do today already, and it isn't even eight in the morning yet...

Friday, December 2, 2016

2.12.2016

Okay, part four it is. Like my faithful readers know, yesterday I experienced a setback when I discovered I had perhaps a bit too ambitious idea of the size of my asshole. So today, as soon as I had woken up (and edged a little, of course) I put clothes on and headed for the porn shop I had visited two days ago.
Also, it occurred to me it might be fun if I had a plug inside my ass during the trip. Therefore I slipped one of the steel plugs in before going out. It's so easy for me nowadays. This time I made my trip in broad daylight and somehow it added to the experience.
That last time it had been the middle of the night. Now it was broad daylight, people and cars passing me by on the snowy street. And here I was, feeling the butt plug moving inside me on every step I took. A faint smile rose to my sleep several times during the short trip.
Going in and out of the store couldn't take more than five minutes. I grabbed the package, made sure it was indeed smaller than the pink monster I had bought yesterday, as well as a new tube of lube, and walked to the counter.
There was the same guy behind it than during my previous trip, and no doubt he could put two and two together. First a guy buys a huge butt plug, before asking about the expendable and more expensive one, and then comes to buy the expandable one and a tube of lube.
On the way home something unfortunate happened. As I was just about to step into the grocery store, thinking I could take care of it while I'm at it, and find out what it would be like to do the shopping while plugged.
Suddenly I felt the plug starting to come out of my ass. I tried to keep it by leaning back towards a trash bin, but a few seconds afterwards I felt it plop out and slide into my briefs. I shrugged and headed back home, thinking whether all my anal training had something to do with it.
As soon as I had gotten inside my apartment I threw my clothes off and opened the package, hands shaking with excitement. As soon as I had figured the simple mechanism out I started applying lube on it and then guiding it in.
The result was... a disappointment. No matter how hard I tried I just couldn't get it all the way in. Finally I gave up and took it out. After comparing it to the handle of the screwdriver I saw it was indeed a bit bigger. Not much, but a bit.
Also the part between the rubber base and the actual plug was twice as thick compared to the steel plugs I had been using. No wonder I couldn't get it in all the way, I thought. As a consolation I took the screwdriver and fucked myself in the ass with it for a while.
After doing some home chores with the diamond plug inside me (which I now hardly felt) I decided to gave the new toy as well as my asshole one more chance. The plug had, after all, cost way much more than I could have afforded.
This time I used more lube then I had ever done before and finally, after much discomfort, I could feel it go all the way in. I was so overjoyed and I remember smiling like a fool. It's in! That huge thing is inside my tiny little asshole!
It tried to slide out couple of times, but I managed to keep it in as I hobbled and wobbled to my office chair. I knew I wanted to keep it in and to sit down. I wanted it in as deep as possible. When I finally did so and had stretched my ass cheeks to give the plug the best access to my anus, I was filled with emotions that were a mixture of horror, amazement and joy.
I knew that plug was the biggest thing I had ever had inside my ass. I was so happy, and almost thanking my asshole out loud, for taking it in. I had lube all over my hands and since I had nothing to wipe them with, I wiped them to my naked body. I didn't dare to get up, in the fear the plug would slide out after all.
After I had my racing heart in control I started to fumble with the mechanism. Despite the price there was some problems, and the rubber tube kept slipping off from the balloon type part at the end. It seems I have to go to the hardware store to get something to fix it.
As I started to pump the device I could feel it starting to expand inside me. In a way the sensation was a bit the need to fart, a sudden feeling of pressure at the mouth of your asshole. The pump part kept slipping off, however, and I finally decided this was enough for a test run.
At first I had the idea I could keep the plug part in and do some home chores, but I soon realized it was so big I couldn't concentrate into anything, not even edging. So I went back to the bathroom and pulled the thing out.
I felt my asshole gaping, and took the vibrating cock shaped dildo, the one I had said is way, way too big for both my girlfriend and me. I took some lube, applied it on the dildo and started pushing it in. It took some time, but bit by bit I got it in deeper, until I felt the end where the power setting is, reach my butt cheeks.
After sliding it in and out for a while I pulled it out, and looked at it. I was overjoyed! The thing was huge and it has been inside my ass. It was the size of a real man's erect cock, much bigger than my cock had been erect back in the day I got hard. Fuck, it had been much too big for my lesbian girlfriend's virgin pussy, and I had just been able to ram it in my little asshole!
I'm writing this with one of the steel plugs inside me. Part of me would want to take it a bit easy now, and perhaps to get some things done. However, there is another part of me that would like to go for another run. It went in once, why not try it again? Should I?

Thursday, December 1, 2016

1.12.2016

I think this report could be more truthfully called “part 2b” as well, since the day continued after I got the previous part written. The thing is, after I finally had the heart to yank the plug out of my ass I could feel my asshole gaping and not wanting to stop playing yet.

Well, as I was in front of the washbasin my eye caught the hand held shower head beside the toilet seat. I had often wished it was the kind you could screw the shower head off. and use it to give yourself enemas, the kind I had a few apartments back.

I took it in my hand, and lo and behold, I realized it came off, after all. At that point I was so horny from all the edging and playing with my asshole it didn't take me more than a minute to slid the hose to my anus and turn the water on.

I admit it this wasn't the smartest thing to do, and that I did get carried off. Some of the water came out occasionally, but a lot of it stayed in, especially after I realized that if I stood up and clench the ass cheeks shut, none of the water got out. I did that perhaps a bit too long, but it felt so good, and twisted.

When I finally started to let the water out and empty my colon I started to have regrets. The flow of liquid seemed endless, I was covered in cold sweat and I started to feel nauseous. Don't do this at home, kids.

After an half an hour or so, and a numerous trips to the toilet later, I started to feel a bit better and decided I could continue. Followed what must be familiar to a lot of people who have been adventurous enough to explore their another love hole. I rummaged through my toolbox and tried to look for anything I could put into my anus, and did so, as well.

The best result I got by using a nice monkey wrench set I had bought a couple of years back, but never used that much. Each of them has a nice, round plastic handle and it was such fun to go from the smallest to the biggest, and to to see whether I could get it in, and fuck myself into the asshole with each one.

I didn't quite get the biggest one in, but when I finally rammed in a handle of a screwdriver I thought was pretty heavy duty, and looked at it after I had took it out I was amazed. This was inside me? I was so proud of myself.

Pretty soon afterwards I had to get going, because I had places to be that night. However, as soon as I had gotten home I got rid of my clothes and started playing again.

A really nice, helpful and open minded virtual acquaintance of mine was online and I discussed with her in length about anal training and sexuality in general, while at the same time keeping a plug in,  and edging myself. She seemed to think it was very hot.

With her help I even fulfilled my fantasy I mentioned earlier, that is going to run some errands with a nasty butt plug inside my ass. The nearby grocery store was at that point closed already, but a gas station next to it wasn't. I needed to get some groceries, so what did it matter whether I had a steel butt plug in my ass or not?

It was very weird, even more weird than running errands downtown in a chastity cage. As I stepped out of the door, I felt as if I had done it naked. Almost like was taking something intimate outside. 

As I walked towards the gas station in the middle of the night I wondered why isn't my brain broadcasting a telepathic message everywhere: "PERVERT! PLUG IN ASS! WATCH EVERYBODY", since the sensation was so intense, almost violent. Every time took a step I felt something in a place of me that shouldn't have sensations.


After I came back I got rid of all of my clothes and started to edge with my friend again. I also told her about my wanking off mirror. I have a small apartment so I have mirrors here and there. One of them is on the bathroom door. If I put the door open just the right amount I can see myself on the computer.

I have the habit of occasionally watch myself in the mirror as I edge. I've always had body image issues and seeing myself nude or wanking off is very humiliating. Then again, I do like humiliation. However, I need to be very, very horny to use my mirror that way.

By the end of the night we had even progressed to clothespins. After my suggestion she made me put some of them on my testicles, and two nasty ones on my nipples. The rattling the pins made as I continued pulling my penis was quite something.

The pins were in place over an half an hour, and she said me being in pain turned her on. It turned me on, as well, and I don't remember when was the last time I was so horny. I hope to be able to do that with her many times in the future.  

Today I continued my anal project and visited a porn store around the corner. The previous day had proven I need new anal toys, and badly. It took me some time, but I finally purchased myself a rather big jello butt plug, since it looked to my eyes about the same size as the screwdriver handle.

However, it seems I was a bit too overconfident, since the pink monster was after all too big for my boy pussy. I can get it in almost all the way, but not quite. In other words my purchase turned out to be a disappointment.

With hindsight, I know now I should have gotten the inflatable model instead, despite the fact it cost twice as much. I do mean to get the pink monster rammed into my ass eventually, and start sleeping my nights with it inside my ass. Just not yet.    

Wednesday, November 30, 2016

30.11.2016

Welcome to "My Boy Pussy Project", part two. Today I've been playing with my third anal toy. It's similar with the fluffy tail plug, with the exception that in the place of a red fluffy part there is a red "diamond", sort of a red brake light.
I bought both earlier this year when we were experimenting with the girlfriend, but the first experiences with the toys weren't only positive. Both toys seemed so small, even though they required a lots of lube in order for me to get them in. I was afraid they would slip inside my anus all the way, resulting to a trip to ER.
So, I was a bit hesitant to use the red diamond one, but since the red fluffy plug was still wet (I washed it, big mistake there) and since I desperately needed something inside me I decided to risk it.
This time I didn't use lube of any kind, just bent over and started to guide the plug to my anus. This is the part I find to be the most humiliating one. After I had found the right place I started simply to push it in dry. I took some time, but finally I had gotten it in as deep as I thought it would go.
However, it was much easier than I thought it would be, or than it had been the day before. I can only hope my training yesterday had something to with it. Also, the whole procedure of bending down and starting to shove something inside your asshole seemed much more normal now.
When I stood up and felt my naked backside I could feel the red diamond part sticking out between my ass cheeks. It seems my asshole was so dry it was keeping the plug firmly in it place, with no fear of it going in or out.
This was good news indeed, since I knew now I could risk what I wanted to do, namely to sit down, and this way to make the plug go even deeper into my ass. Also, sitting down with the feeling of a steel plug in my ass was humiliating beyond belief.
As I am writing this the plug is firmly in my anus. At first it seemed "fucking myself" wouldn't be possible in the similar way with this toy, since there isn't similar "ball" part at the end of it.
However, the longer I sit here and rock myself back and forth while I edge myself, the more "life" and movement there seems to be between my ass cheeks. It seems my muscles are trying to thrust it out, but my weight prevents this. By gyrating my hips in round motions I can feel something wonderful happening inside me. It seems enjoying things inside your asshole is an acquired taste.
By making a slight "hopping" movement, in other words moving my hip and down using my leg muscles I have even managed to create a bit of the thing we've used of seeing in porn movies, in which the actress is riding a hard cock. Or, if I keep the two fingers around my my soft clit motionless, and hump my hip back and forth in sort of slow strokes I can fuck my hand and myself in the ass at the same time.
Also, I noticed that if I first stretch each buttock and then let my weight descend, the mixture of sensations is overwhelming, almost violent: the feeling of my stretched out asshole, the sensations the plug creates inside my dry anus, the constant fight my body and mind have against each other, whether to get the nasty hard thing out, or further in.
When I first tried this, after sitting on the plug almost an hour, a long, almost orgastic wail escaped my lips: "Aaaaaahhhhh!". It's impossible to know how much of it was pain, how much was pleasure. I had never felt anything like it. After an half an hour or so I also noticed this technique makes the plug go much deeper inside my dry ass, than it so far had.  

The thing is, before I tried that technique I suspect the plug was inside my anus only half-way. This is not only a bad thing either, of course, since this way the widest part was most likely at the "mouth", hopefully widening it.
Now the only problem that remains is that I this is way too much fun. I love the feeling the plug creates and I don't want to take it out anymore.
I would have so much I'd have to do today, but as long as the plug is inside me it's quite impossible for me to think of anything else than rocking myself back and forth in my chair, and edging...