Create a Snakes and Ladders Game for Me!

[brat_tamer]

30

Spoiler:

Insert one pair of panties, followed by 2.25'' anal plug to hold them in. If you cannot hold a plug and the panties in your ass at the same time, PM me.

[generaterox]

31.

Spoiler:

You may move up to 10 step forward(Up to post 41). For each step you choose to take, you’ll thrust your 2.36” butt plug in and out of your ass 3 times.

[SluttySarah]

Sorry for being gone for a while, I think I mentioned that with school starting and me moving to a new place my life would be rather hectic but I didn't realize it'd be sooo busy. I've been dying (metaphorically) from all my midterms and my classes are so much harder this year. My new place also doesn't have nearly as much privacy as before and I'm living with a close friend now so sometimes they'll come talk to me. The only time I can really play with my butt is late at night, preferably on weekends. But after my midterms I definitely do want to attempt the first 25 squares of the Snakes and Ladders game!! I don't have room for a nice mat like before so I might have to change a few of the dares, but most of them are pretty discreet and don't make a mess which is nice

I realize I was gone for some time and so the thread kind of died down - I'd be okay with making new squares by myself, but it isn't nearly as fun. I hope I can get some people involved again, I really do love the ideas and I'm very excited to try them, even if it'll leave my butt prettyyy sore. Still hoping to be able to take that 2.6'' plug someday!

And here's the square, since this is technically a post:
32:

Spoiler:

From now on, for every square forwards or backwards I move as the result of a dice roll, I must work my 2.36'' plug in and out of me once. If this thread does not reach 50 tasks before the end of October, move I will move 3d6 squares backwards

It's quite punishing because I feel bad about being gone, even if it was for a hectic period of school.

I'll likely start with the game to square 25 this weekend (I had started before but I got too busy so I'll start again from square 1). Expect to see some long reports then!

[SluttySarah]

Posting on part of cutehamster

33:

Spoiler:

I will thrust my 2'' glass plug in me 5 times the dice roll used to reach this square

[Leland]

34

Spoiler:

PUT THE COOL IN THE SCHOOL
Busy and tired because of school? Not anymore! Lube your 2.25" or 2.36" plug with very COOL minty toothpaste and then stick it into your happy place. Now sit at your desk and do some homework or take a school book and study it. Or read any book if you have nothing to do for school. Do it without breaks for at least 10 minutes. Then read the next spoiler. Learning is exciting again!

Spoiler:

10-15 minutes: the bare minimum. Disappointing! Roll the dice and advance that many squares if you roll 1, 2 or 3. Go back that many squares if you roll 4, 5 or 6.
16-20 minutes: good enough. Add +1 to your roll and good luck.
21+ minutes: what a bookworm, stop it, nerd! Take this Magic Bookmark and go away. Single use. If you roll after completing a square and you don't like your next destination, discard that roll and go back in time: repeat the square you just completed.

[brat_tamer]

Originally Posted by brat_tamer

30

Spoiler:

Insert one pair of panties, followed by 2.25'' anal plug to hold them in. If you cannot hold a plug and the panties in your ass at the same time, PM me.

As you could not fit both at once as per your PM, you must keep the panties inside your ass for an hour, then remain plugged for an hour.

[Azyliux]

35

Spoiler:

Bad luck. Snake to 11.

Azyliux

[SluttySarah]

Now that it's the weekend, I'll be playing the game until I reach at least square 25! In November, I will play the game till 50 squares, and in December I will hopefully be able to play until 75, and in January around my birthday I hope to be able to play the complete game with 100 squares!

I will be using my rolls from https://www.random.org/integers/?num...nd=id.buttplug, going down the list for every time I have to make a dice roll. This is more convenient, and so you know I'm being honest about my rolls in case I get really lucky! I'll run the generator with different random words when I play the game again in the future.

Expect some long reports, and I might write a short summary at the end of the weekend or when I finish the game (unsure rn if I can finish in one weekend!) about if it was too easy or too hard, and I hope people who add to the game going forward can keep that in mind a little

Edit: Forgot to add a task with my post:
36:

Spoiler:

I will wear my nipple clamps and be plugged with my 2.36'' plug until someone posts in this thread.

[Azyliux]

37

Spoiler:

Roll 1d6 and multiply it by the roll that brought you to this square. Insert and remove your 2.25" plug into your ass this many times in a row without pause. If you need to stop for a break, restart your count at the beginning. If you fail after three attempts, a snake takes you back to square 1!

Azyliux

[StealthyKitten]

38

Spoiler:

Bad Luck: Either apply toothpaste to your clit, ass and nipples OR snake back to 13

[SluttySarah]

I started playing tonight and WOW it took me a long long time to warm up after going a month without stretching my butthole! The first dice roll was a 2, which sent me from square 1 to square 2 as I was to subtract 1 from my next 3 rolls.

I struggled to take my 2'' glass plug, which before I had always been able to take without any warm-up, and even my 1.75'' plug was difficult. I played with the 1.75'' plug, pushing it in and out, for about half an hour before I felt comfortable enough to take my glass plug, and even then it hurt a bit stretching my butt to work it in. I then moved onto pushing the glass plug in and pulling it out of me, which I did 10 or so times after which it was going in fairly easily. The 2.25'' plug was still monstrously huge, and I always considered it about as difficult to work in me as my 2.36'' plug, just because of the length (there should be a picture of it somewhere). It's so wide, and for quite a long stretch so I can't just "pop" it in me. I found myself actually panting a little after pushing it in me, partly because of the effort and because of how it felt. I also found myself pushing very hard against the plug, as it made it easier for me to push it in - it's just so so big! After doing so 4 times I had to take a break in the bathroom, and then completed the final 6 in one go afterwards. I was worried after the first 2 times I worked the plug in me if I could really handle it 10 times, but it seems once I was properly warmed up and my butthole was stretched out it wasn't so bad. The last 3 I did without any breaks at all, since I found that it was easier to push it back in me before my butt stopped gaping (which it definitely was a bit each time after the huge thing came out!). It felt soo intense, mostly in a good way, and I could really feel myself getting rather wet. Shoving the pair of panties I wore today in my gaping butthole after the 10th time was unsurprisingly very easy, although the texture is still a bit rough and it still feels weird. They're in me as I write, and will be for another 10 minutes (as I write this right now, I'm not sure when I will be done writing).

Another thing I realized was that my plan for the dice rolls has a big problem (haha oops!). I'll know what my next rolls are, and I shouldn't be able to plan around that, especially since the first square lets me reroll once. So I think I'll go with telling google to roll a 6 sided die instead. Didn't think that one through!

Speaking of which... I'll let google roll now.
Oh. I got a 1. I rerolled and got a 3. Which puts me at square 2+(3-1)=4. I guess instead of taking out a pair of panties in 5 minutes, I'll be stuffing another one in me . (no coating in oil b/c I don't want a mess) Since square 4 is just a rule, I'll roll again to see where I move to. If it's a square divisible by 3, I think it's ok if I just stuff a second pair in me and take both out right after.

It's a 1. Which puts me back at the same square. Since it's the same rule again, I guess that means I just roll again. It's a 6, putting me at square 10. Oh, I really don't want to spend too long with 2 pairs of panties in me I also hope it's ok if I write these reports without wearing my nipple clamps, I think it'd just be much too mean...

edit: Forgot to add a square again!
39:

Spoiler:

Free Pass. I think I deserve it with how hard the game is :). However, if anyone replies or PM's me saying this is too nice, I will change this to "move backwards instead of forwards from this square"

[SluttySarah]

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!

[generaterox]

41.

Spoiler:

Roll 2 dice, you’ll thrust your 2.36” butt plug in and out of your butt equal to the number rolled at the start of this task.

[SluttySarah]

I was instructed to stuff 2 pairs of panties in me before each roll and taking them out if the task was one that required my butt. I suppose this is the much more reasonable interpretation, I was probably just hoping to get off a little easier. My asshole is definitely still sore today, and stuffing two pairs of panties up my butt was certainly not pleasant. I did get to stuff them in me together this, rather 1 by 1 like last time (since I had to keep 1 pair in me for half an hour before rolling into square 4) which made it a little easier I think. Regardless, I hurriedly rolled the dice and got a 3, which landed me on square 14+3*2 = 20 (doubled since I was plugged for 3 hours on square 14). A free pass! I then rolled a 4 (so so close to square 25), landing me on square 24. I pulled out the panties in me, and it hurt!! Not as much as last time because I hadn't needed to stretch out my butthole with my really big plugs beforehand, but was definitely still a very intense feeling.

I remembeedr square 24 had something to do with me using a bigger plug (I read all of them beforehand to make sure it's something I can do!), so I decided to use my 2.25'' plug. Since I had to go slow, and as a challenge to myself, I didn't warm up with my smaller glass plug, and instead decided I would have the 2.25'' plug be the first plug I work inside me. And very slow it most definitely was, and I left it in at it's very widest part for about a minute to really really appreciate just how ridiculously stretched it leaves my poor little anus. Unfortunately, I wasn't able to pull it out very slowly... I have to push sooo hard for my asshole to stretch open around the widest part and after that part came out, I was even trying to push it back in with my hand but I just couldn't, and the plug popped out. I'm really really sorry, I know I was supposed to take it out even slower than I put it in but I just couldn't do it

I just rolled a 1, meaning with the +1 to my roll, I end the game on square 26, which tells me to rest for 15 minutes with a small plug in me. I'm wearing my 1.75'' plug now.

Overall, I think playing to 25 squares was difficult (yesterday especially!!) but that I also got off somewhat easily. Square 20 was a free pass (courtesy of me haha), and I never got sent backwards, which I think would be especially bad. Square 4 was quite awful though, I'm reminded again of how incredibly intense it is to have so much fabric stuffed in me. In retrospect I definitely should not have spent my reroll to avoid landing on square 2 again.There are far worse squares to land on. And as the game gets longer, and I think snakes downwards will become much much scarier! I'm hoping there are more tasks with my plugs or nipple clamps in the future, and maybe some more ways to earn a chance to reroll? Pretty please?

Sorry these reports are a bit rambly - I'm not exactly in the calmest mental state while writing these lol.

42:

Spoiler:

I will gain one oppurtunity to reroll the dice whenever I wish. For the next 3 squares I land on, any time I would have to plug myself a certain number of times, I must do so twice as many times, and any amount of time I must stay plugged is doubled as well.

I'm hoping this will be deceptively nice for me, since if the 3 squares I land on afterwards are just rules or snakes/ladders or don't involve plugging I might get a free pass and a free reroll

[Leland]

43: THE BIG BAD BOSS

Spoiler:

Take your giant impossible 2.6'' plug. Yes, that. Don't worry: you win even if it doesn't break in!
TASK: relax, lube it generously, relax more, repeat to yourself that you deserve it, take a deep relaxing breath, push it in for 4 continuous seconds, relax.
- You can repeat the ordeal above up to 4 total times if you want, but every time you must try to push it in just a teeny tiny bit harder than the previous attempt.
- You can also try a 5th time for an additional prize, but this time you must push it in for 6 continuous seconds and with SERIOUS and slightly increasing strength.

Spoiler:

Well done! Your honest attempts deserve a prize: for every attempt you gain +1 to your next roll.

If you tried all 5 times, you also gain an object: the BACKDOOR TICKET (One use only): after you complete a square, instead of rolling you can use it to be teleported back here. You must fight again the BOSS and you can't gain another TICKET.

In the IMPOSSIBLE case that you DEFEAT the BOSS by sticking it all in: congratulations! You trascended your human limits! You gain both prizes above and also the FORESIGHT SUPERPOWER: from now on after you complete a square you can roll your dice two times and choose the roll you like more. But in order to use this power, you must have your divine 2.5" plug inside you while rolling.