44.

45

Double trouble
 

46

Snake it back to 23 OR 4. If you choose 4 you can roll twice and move that combined number without stopping on the individual number.

If you go to 23 your next role moves you back instead of forwards

47. Bounce and Shake


Azyliux

I will be playing the game to square 50 starting November 1st! I'll finally finally be done all my midterm exams by then :) My roommate will also be gone for a while so I'll have the place all to myself. It'll be quite a bit longer of a game this time, so might take a few days to complete!

48:
I feel like this square is actually quite nice since at worst this is just a single enema, but I'll always have the option of avoiding one or two really bad squares in the future.

I'm also thinking of adding some modifiers to the start of the game, so that I can either make it easier or more difficult - for when I need to be punished, or when I'm just looking for some fun.

49

My master generaterox has decided the special 50th square task for me, which I am posting on his behalf.

50.

Square 51

I am starting to play the game through to square 50 now! I am writing in a draft blog post as I play, and will post that as a report after. It might be a bit long and rambly because I'll be writing it as I play, sorry! I won't be wearing my nipple clamps while writing because I think that'd just be too much... I think I'll be needing the breaks. If you see me online but not replying to PM's, that might be why. Conversely, I might have to spend quite some time plugged or otherwise encumbered by panties up my butt or wearing nipple clamps, and be bored and looking for someone to chat with to distract myself. I am running out of ideas for squares to add whenever I post, after all.

52:

Snakes to 50, Report 1
 

This is my running report of tonight, which I am writing in a draft blog entry and will upload to the thread after, maybe with a bit of editing!

I rolled a 1, and since my first 3 rolls put are decreased by 1, this puts me back on square one again. So my next two rolls will be lowered by 2, and the 3rd by 1.

Oh, I rolled a 1 again. Which lands me on square 1 again (since I can't really go backwards). So my next roll will be lowered by 3, then 2, then 1. I'm a little worried I'll keep rolling numbers less than 1, maybe I should just wear my clover clamps for 15 minutes so I can skip square 1 in the future? I guess landing on square 1 isn't that terrible though, so I'll roll again. It's a coin flip's chance I get to move on anyways. I rolled a 2, which brings me back to square 1. I'm also realizing that the worst it can get for me is -3, then -2, then -1 so there really wasn't any reason for me to wear my nipple clamps. I'll just keep rolling until I get something more than 3. 2, 1, 1, 4. Wow, that's a lot of low numbers. I wish the gamblers fallacy were true!

So I will move 1 square forward to square 2, and decrease my next roll by 2, and the one after by 1.

Square 2: 10 insertions of my 2.25'' plug followed by 30 minutes stuffed with a pair of panties. I chose to wear my nipple clamps for 15 minutes (6:07-6:23pm), so I may avoid this square should I have to return to it in the future of this playthrough at any point (I forget if there is something which takes me back to square 1, but I think there might be). It takes so long and is quite draining so I think it will be worth it. At first I was worried my butthole would be as unready as last time, and it would take forever to warm up, but this time it went much better. Within a few minutes I was comfortably pushing and pulling my 2'' glass plug in and out of my asshole, and I played with trying to hold it at the widest point without my hands and avoiding pushing it out or sucking it in. The 2.25'' plug went in after. It was difficult like always, but didn't hurt at all. It still felt plenty huge inside me, and pushing it in and out of me 10 times was still quite a challenge and an incredibly intense feeling. I had to take a bit of a break after each time I thrust the plug in me. I would have preferred to rest with the plug outside of me, but I would gape a little each time I pulled out the huge plug and I wanted to thrust the plug back in me before that gape closed. I had to take a break on the toilet a few times even though I had taken an enema before, because such a big object going in and out of my butt made me feel like I needed to poop! I finished at 6:45 (I left the plug in me when I pushed it in the 10th time, resting a bit and dreading having to stuff my panties in me hence the nice interval), and pulled out the plug and immediately stuffed the panties I wore today (which I had already taken off and set on my knees) into my slightly gaping hole before it had a chance to fully close. They went in deeper than usual, and my sphincter can fully close around them. This is actually making them muchhh more bearable compared to usual where the rough fabric rubs against my sensitive opening every time I involuntarily clench around them. It still kind of feels like this inside, but much less overstimulating. It is now 7:05, so I have 10 minutes remaining before I can pull out my panties. Now that I think about it, since my next roll will be lowered by 2, if I roll a 2 then I will be very very happy that I chose to wear those nipple clamps for 15 minutes! And I really hope I don't roll a 1, since then I'd be going back 1 square back to square 1 again. It's 7:10! I'll pull out my panties, and post this on the thread. I'll edit it later with some task for square 53, I can't think of one right now.

53:

Snakes to 50, Report 2
 

I rolled a 4, which lowered by 2, brings me from square 2 to square 4. I really don't want this to happen again :( it's the same start as last time and I really can't stand having 2 pairs of panties in me for very long... I do wonder though, since I technically landed on square 1 a total of 6 times, I should have 6 rerolls! This might actually be the luckiest start to a game I could hope for lol. I know this might seem a little unfair, but it was also incredibly unlikely and just as terrible things can happen to me if I get incredibly unlucky.
My reroll was a 2, which lowered by 2, puts me back on square 2. Since I wore my nipple clamps for 15 minutes, I am allowed to skip this square. I rolled again and got a 6. Lowered by 1, this moves me from square 2 to square 7.

Square 7: Move forward 10 spaces and perform 10 panty stuffings.

I'd really like to not have to stuff panties in and rip them out of my butt any more, but 10 squares is a lot of squares forward and I don't want to use any more rerolls when I can, even if 5 rerolls sounds like a lot to have.

OH MY GOD that was terrible. It was sooooo overstimulating I was leaking wet from both my pussy and somehow, my asshole. I was wearing my nipple clamps and I swear I couldn't even tell, the feeling of rough fabric being pushed and pulled out of my poor abused asshole was all I could focus on. Pulling it out was especially bad, it felt like my panties had become impossibly long and I would be pulling forever. And again I couldn't even afford to take a break because the easiest time to stuff the panties I pulled out was right afterwards when my asshole was slightly gaping open. I don't even know how my asshole was left gaping, it's not like the panties are stretching me! I'm still panting a little as I write this, it was sooo intense. I even stuffed my 2.36'' plug in me afterwards because I was so turned on and have it in me as I write, but it's starting to feel a little, well, big, so I might go to take it out. I really hope square 17 isn't anything too bad, and I get a few free squares to move forwards. 10 squares forwards is not bad, I must say. But I think I should've rerolled and hoped for something easier!

54:

Square 17 tells me to do my next 5 tasks blindfolded. I don't have a blindfold, but I complete most tasks with the lights off anyways, so I'll just make sure to keep my eyes closed at all times. I also have to guess a dice roll to decide if I move forward 2 or backwards 4. I guessed 3. It was a 6. Didn't really expect to win this game haha, I'll be going back to 13.

Square 13: From now on I will keep my last inserted plug in, in between tasks, and for half an hour before taking a break from the game. I can drop the rule if I find a way back to this square, so here's to hoping I get to square 17 again somehow!

Oh lol, I rolled a 4, putting me back on square 17. I guessed a 3, and rolled a 2, putting me back at square 13, which cancels the rule. Well that was convenient! This time I rolled a 5, putting me on square 18.

At first I thought I had to do 3 sets of 20 jumping jacks all with my nipple clamps and weights on, which would be farrr too painful!! Thankfully it is just one set, but I'm still dreading it :( Just wearing clamps with weights hanging off of them hurts so much I'm so so scared of how it'll feel jumping up and down.

Doing 40 jumping jacks with just my nipple clamps on was ok. The chain rattled every time I jumped and was a slight tug on my nipples, but the moment I added those weights I just couldn't do it. They tugged on my nipples so badly and they hurt so much I couldn't bring myself to do anything more than a pitiful little jump. Which left the weights in free fall and reallyyy yanked on my clamps and it just hurt so so bad. I'm really sorry I couldn't complete it, or even jump until the clamps fell off it just hurts so so so bad.

It brings me 2 squares back to 16, and 16 is a snake down to 4!! Oh, what terrible luck... I should've just rerolled when I saw I was going to land of square 18...
And I need to have 2 pairs of panties stuffed in me for the next 3 rounds, although square 4 already says I need to have 2 panties stuffed in me until I land on a square with number divisible by 3... I guess I will just go by whichever rule lasts longer. I've been dreading square 4 - I ran into it last time and I just absolutely hate having 2 pairs of panties stuffed up in my little asshole...

I will wear my clover clamps for 15 minutes, so that if I land on square 16 again I will get a free pass. From the wording, I assume this must be after I get two pairs of panties stuffed inside of me.

Even though I used two thongs which had much less fabric my already sore and roughed up asshole reallyyy chafed against them filling me up. Waiting for 15 minutes with clamps on my nipples which already hurt from earlier was pretty punishing, but thankfully I got a little luckier after. I somehow rolled 4 3's in a row, which first took me to square 7, which thankfully I had worn nipple clamps while completing last time so I got a free pass. I rolled another 3, bringing me to 10, and so I had to put on the clamps I had just taken off (youch!) and do 20 jumping jacks bra-less. That made it hurt quite a bit more, since before I had sort of sneakily been wearing my nipple clamps under a bra so when I jumped up and down the clamps wouldn't move much. Without my bra, the clamps and chain in between jumped up and down more which gave some little tugs of pain when I landed. I was also still aching to take out the panties in my asshole, and I couldn't help but involuntarily squeeze down on them inside me while doing my jumping jacks. The next 3 took me to 13 again, so I regained the rule that I will keep my last used plug in me in between tasks. Then the final 3 took me to 16, which THANKFULLY I had worn nipple clamps for 15 minutes on, so I could move on instead of being sent back to square 4 again. I rolled a 4 and got to square 20, which was a free pass, and then finally rolled a 1, landing me on 21 and I just removed both my nipple clamps and the panties from my asshole as it was a square divisible by 3 and it had been more than 3 rounds. Thankfully I didn't actually have them in for too long, since I was just jumping between tasks and desperately reading and rolling as quickly as I could.

54 (I couldn't edit previous one, sorry!):

55:

55
 

This is mislabeled. It should be square 56.

I won the coin flip for square 21, and rolled a 4 bringing me to square 25. Originally I didn't want to soak my panties in oil because I want to be able to dry them in the dryer, so mafiaka has allowed me to instead do the dare with a bar of chocolate, melted in my butt. So 25 jumping jacks and 25 crunches without leaking any chocolate on the floor and I can move on, but if I leak I'll be going back to square 12. Honestly I don't even know how I'm going to get a whole Lindt bar inside me... but I've been told it will melt slower than I think.

I tried breaking up the chocolate bar to insert the pieces in me, but they were way too sharp and hard for me to feel comfortable putting so many pieces in me, so I decided to do the original option with the oil. I used two thongs so they wouldn't be so filling, and while I didn't really have a good way of measuring out exactly 50mL of oil, I did absolutely drench them in oil before stuffing them in deep in me. I made extra sure I could fully close my butthole around the panties so that I would avoid spilling any oil. Pushing them in me kind of made a mess and a lot of oil got all over my butt, but I don't see how I could have avoided that. But with the panties deep inside me, I just had to try my hardest to not accidentally try to push them out and to keep my asshole closed while I did the 25 jumping jacks and 25 crunches (I had a towel beneath me just in case). I wanted to push out the panties soooo badly but I resisted. Afterwards there was a little bit of oil (?) on my thighs, but I don't even know if that was sweat, oil from when the panties went in me, or my wetness. That doesn't counts as spilling, I hope.

I rolled a 6, putting me at square 31. I knew square 32 would be punishing, so I made myself shove my hugeee 2.36'' plug in me 6 times. My ass is still throbbing around the huge plug as I write this :( I had to keep it in as by the rule I gained on square 13.
The plug is thankfully rather short, so once the widest point made it past my sphincter it popped in. Otherwise, I don't think I could have taken it... It's nice and filling once inside me, and actually not so bad which is why I am writing this now instead of moving onto square 33 right away.

Square 33 says to thrust my medium glass plug in and out 5 times the number I rolled to get here. I didn't roll a dice to get here, but I think it's fair to use 2, since I came from 2 squares away. I get to take out my big plug at least!

The glass plug went in and out very easily after using that huge 2.36'' plug. I even left it in at it's widest point for a little bit, challenging myself to hold it there without pushing it out or sucking it in. Keeping it in me now feels good actually!

I just rolled a 2, which would land me on square 35 which has a snake down to 11! But thankfully I still have 5 rerolls left from my lucky start. I rerolled a 3, and I think square 36 is not so bad. I'm going to plug myself with my 2.36'' plug and put on my nipple clamps, then post this report. I'm really really counting on someone being online to help me out here!!

57:

58.