I thought pushing a second pair of panties up my sore and abrased asshole was definitely going to be the most painful part of this report when I did it, but pulling them out hurt sooooo much more.
I rolled a 6 which put me on square 10, and after stuffing the second pair of panties in me, which hurtttt and was very uncomfortable to keep in, I put on my nipple clamps. I couldn't do jumping jacks because it's late and it'd be loud to jump up and down so I did 20 push-ups instead, which didn't take too long thankfully. It was kind of hot hearing the occasional clink of my nipple clamp chain. My very strong desire to take out the two dry scratchy panties completely filling my rectum definitely helped me complete them ASAP. I rolled the dice right away, and got a 4, putting me on square 14. Not a square divisible by 3, but because it requires I be plugged with my medium (glass) plug for up to 3 hours, it's a nice excuse to take out the two panties in me. And wow that hurt!! Pulling out the first one hurt especially badly, and all the stimulation of the rough scratchy fabric abrasing my already sensitive sphincter as it was dragged out thankfully made me push out the other pair right after without any pulling. My butt kept thinking it really needed to poop and so I pretty much involuntarily had my asshole gaped trying to push something out that wasn't there. I wonder if having panties stuffed in me feels so intense because the lack of a rigid shape lets it indirectly push against my G-spot(where I would normally finger myself) somehow? I did this in the shower and took a shower to be clean, and now I'm writing while plugged with the glass plug. It feels amazingly small now, despite it being a sizeable challenge at the start of the night. I thought it might hurt a bit going into my scratched up anus but I guess the fabric from the panties are only rough enough to *feel* like they're scraping my sensitive sphincter. I haven't quite decided if I should wear it for 1 hour and try to complete another task tonight or just go to sleep with it in which'll let me double my next roll. I'm leaning towards sleeping with it in and doubling my next roll because I assume I'd have to stuff 2 pairs of panties back in me when I take it out (still haven't landed on square divisible by 3 after all, I technically only took out the panties to complete this task) and my poor butthole can't take any more of that. With a lucky doubling of a 6 roll tomorrow, I could successfully complete the game with only 1 more task!!
IMPORTANT: I am wondering though, tomorrow when I start again, how does the "I must have 2 panties stuffed in me until I reach square divisible by 3" rule work? Most of the tasks do seem to include using my butt in some way, which means I'd have to take them out. Can I just understand the rule as "have 2 panties stuffed in you for any task not involving your butt until you reach a square divisible by 3"? Somehow that feels a bit cheap and not what was intended. Or should I start out by stuffing 2 pairs of panties up my butt and pulling them out right away if I roll into a task involving my butt, and doing that again after each task? I don't want anyone thinking I'm letting myself off easy, so please tell me!
40:
Spoiler:
I will roll a dice, and have that many minutes to work my 2.36'' plug in and out of my butt as many times as I can. For the next 5 dice rolls, including the one used to leave this square, I will roll dice with sides equal to the number of times I fit my 2.36'' plug in me. Timer starts with the 2.36'' plug inside me.
I think this'll be a very good square for me, but it'll depend on my luck and how comfortable I am with my plugs!