Create a Snakes and Ladders Game for Me!

[Kaiyo]

74

Spoiler:

Go back 8 spaces, Insert your Hush, turn it to max Power until you pass this square again

[mafiaka]

75

Spoiler:

To celebrate this enormous milestone, finger your ass for 7,5 minutes with as many fingers as you can get in.

[SluttySarah]

Thank you everyone for adding to my game!!

I will be back from vacation in a little over a week from now and I hope to play through the game to square 75 whenever I have time then. Looking through the squares again, I should be able to complete nearly all of them even with my roommate home, and she might not even be home when I get back so I might have a day or two then. I do still have a bunch of PM dares accumulated over the break, but I think I'll get working through those after I play this game.

I was also able to work my 2.6'' plug in me a grand total of 2 times!! I spent a couple hours after my last exam trying really hard and managed to work the ridiculously huge plug inside me by putting it on a chair and slowly lowering myself onto it. It took hours of warmup though and even then was a bit painful so I don't think I want to try and push it in me like that again until I'm really ready and my "smaller" 2.25/2.36'' plugs feel comfortable.

I'm really excited to get back and start

Square 76:

Spoiler:

Catchup Dice: From now on, I will halve, rounding up, all dice rolls made while on or past square 76 and double all dice rolls made while on squares before square 76.

[mafiaka]

77

Spoiler:

Squeeze in the 2.36'' plug.

[StealthyKitten]

78

Spoiler:

Blindfold yourself and write good girl on some paper. If its legable move forward 3 spaces, if its not (or letters overlap) apply toothpaste and move back 3 spaces

[SluttySarah]

I will be playing the game on the 13th and 14th! Hopefully two full days (~30 hours) will be enough to complete it. It'll be tough for sure but after being on vacation for so long I don't mind some meaner training.

Square 79:

Spoiler:

From now on I will swap panty stuffing tasks with buttplug tasks and vice versa. 1 panty = 2'' plug, 2 panties = 2.25'' plug, 1 min stuffed with panties = 5 minutes wearing plug

[SluttySarah]

Almost back home! I ordered an inflatable enema plug thingy because I always have trouble holding my enemas...

Also I kinda want to add some extra rules to help me out

If I always turn on the vibrating feature of my 2.25'' hush whenever I wear it, I get to start on square 1d15 instead of square 1.

If I always use my 2.36'' glass plug instead of my 2.36'' silicone plug I get to skip a square for free whenever I want.

If I disallow myself from using my thongs for panty stuffings I get to skip 1 panty stuffing related square

From the so so many punishing tasks here I know you all want me to thoroughly train my butthole So in exchange for all these nice options for me, I offer to only take 3L enemas with my new plug nozzle for cleaning. Nothing solid other than buttplugs and my underwear allowed to come out of my back hole for 2 days! (3L is a LOTT for me! I'm small, and a girl, so this really is filling!! Will leave my usually very flat tummy bulging, but it looks kinda cute if I do say so myself )

What does getdare think? If something isn't fair just PM me, I don't want to be tryna get off easy!

Square 80:

Spoiler:

I will clamp my nipples and pull on them so that my boobs reach the same height away from my chest as the width of my last used buttplug (hey, they're small ok). If I can't I'll punish my nipples by leaving the clamps on until I get another nipple clamp task

[generaterox]

Hi little slut! I like all of your suggestions here but I feel that just taking a 3L enema is letting you off too easy for such great benefits. To make it just slightly more challenging for you, I want you to have your harsher nipple clamps on while performing your enema and I would say that you’re good to go! Enjoy your snake and ladders game little slut.

81.

Spoiler:

You’ll roll a 2d6 and sum the results up. That is the number of squares you’ll have to move backwards by. You may half the number of squares(rounded up) you’ll have to move back by inserting your large hush plug and enduring the vibrations at max setting for the sum of your 2d6 results.

[SluttySarah]

I'm writing in a blog draft to keep a running report of the next two days as I play through my game.

4:30 pm (EST):
I'm finally back!! Soo excited to be playing my game now. I'll be using all of my new rules:

1. Hush always on
2. Use 2.36'' Glass plug instead of silicone
3. No thongs for panty stuffings
4. No pooping normally, only 3L cleaning enemas wearing my meaner clamps.

In exchange, I will be starting on square 1d15, I can skip any square once this game, and I can skip a panty stuffing square once this game.

I think I'll put off the big enema and only do it if I really need to. Hopefully I'll only have to do it once tomorrow and not at all today!

Also kind of scared... my butt hasn't been trained at all for weeks now since I've been on vacation but I'm also so so horny from not being able to play with myself in any way at all, for soo long :/

The first big roll - to see which square I start on! It's a 9!

I have to work my 2.36'' plug in me as fast as I can after touching it, but since I hadn't even warmed up yet, I decided to first push my slightly smaller 2.25'' hush plug in and out a few times to warm myself up. Doing that with the plug vibrating the whole time was really stimulating! I left the vibrating plug in me and poured lube on the glass 2.36'' plug, starting the timer with my left hand as soon as my right picked up the plug and I did my best to smear the lube all over it. I then pulled out the vibrating hush plug (I knew if I pulled it out right before it would leave my asshole gaping a bit) and pushed in the glass plug, which thankfully went in without too much effort. Stopping the stopwatch, it reads 19.74. I'm quite happy that my butt is still able to take the plugs from before, and that the few weeks on vacation and before that, finals season, didn't change too much.

Getting the big plug in, in under 30 seconds lets me roll twice leaving this square. I rolled a 1 and a 6, so I'll be going to square 15.

Since one of the outcomes might send me backwards, I'll choose to wear my nipple clamps for 15 minutes for this square so that if I land on it again, I can skip it. I pushed my 1.75'' hush plug in and out of me 15 times and flipped heads, so back to square 10 for me! But first I need to wear these nipple clamps for 10 more minutes... thankfully I don't have to use my meaner clamps, and 15 minutes with my old clovers isn't too bad. At least for now, when my nipples still aren't too sore. But I'll have to keep them on for a while probably, since square 10 tells me to do 20 jumping jacks wearing them and keep them on for the next two turns.

As I'm waiting for 5:10 to come (it is now 5:05) I can't help but notice I'm on the square I would be on if I chose the 1 instead of the 6 lol, kinda ended up going nowhere.

Finally 5:10! I'm wearing my clover clamps horizontally so they fit under my bra a little easier, and aren't hanging (which hurts a little bit more) but now that means when I do jumping jacks my poor nipples are gonna be twisted 90 degrees the whoole time...

Just did my 20 jumping jacks. They hurt. Every time I bounced up and down my boobs although small bounced more and that made the horizontal clamps harshly twist on my poor nipples

And I'm writing wearing nipple clamps, since I need to keep them on for the next two tasks. I hope they'll be quick. I rolled a 5! Very lucky haha, since I already completed the square and chose to wear my clamps for 15 minutes when doing it, I can skip square 15 and roll again. I rolled a 3, putting me on square 18.

Ohh I know where this one leads... I'll fail at the very end because I can't handle jumping with weights attached to my nipples and then I'll be sent to square 16 which is a snake down to square 4. I remember this one! I really didn't want to use it this early, but I'm going to use the one unconditional skip I have to skip this square.

I rolled a 2, letting me go from 18 to 20. 20 is a free square the first time I pass it, but in the future it'll send me backwards! And I think there's some other squares which will send me back here. A four. So I'm on square 24 now, which tells me to pick a plug and push it in and out veryy slowly. I know there's a catch with the size of the plug, so I'll go with my big hush plug, even though it'll have to be vibrating the whole time. I'm pretty happy with the easy progress so far... I know most of it was bought with the conditions I gave myself though, and it'll get a lot tougher. I'm also still wearing my clover clamps (now 5:21) since I skipped 2 squares and had a free square (I will count the free square as a square completed for the sake of taking off my nipple clamps, but not the other two. I hope this is fair)

5:27 I veryy slowly work the vibrating plug in me, and then also took it out very slowly, letting it sit at its widest point stretching out my butt. The vibrations were almost numbing, and I pushed it slightly in and out then, feeling the plug push and pull on my sphincter. I'm happy to be rid of my nipple clamps, and using the plug like this is feeling very very pleasurable

I rolled a 6, and I get to add +1 since I used my big plug! 7 squares forward moves me to square 31.

Hmm this is an interesting square. I can move up to 10 squares forwards, but I have to push my 2.36'' glass plug in and out of me 3 times per square. I completely don't remember what the squares are, so I suppose I'll just try my best to work my glass plug in and out 30 times and stop if I get tired. ahhh ok that was a bit overconfidentt I worked it in me 6 times and I don't think I can take it much more - it'll be easier to just complete other squares I think. Every time the big plug slips into me it just feels soooo intense and I just can't takeee itt. The 2.36'' glass plug is harder than the 2.36'' silicone one because the silicone one kinda shifts or squishes a bit to be thinner than it is but the glass one doesn't.

At least square 33 isn't bad - Using my last roll, a 6, it is 30 insertions of my 2'' glass plug. Should be easy for me now!

It was easy, but still felt very good!! I can feel myself getting pretty wet - I won't be able to soothe that need but it definitely feels good to be able to play with my butt again.

I rolled a 3, putting me on square 36. I need to find someone to post in this thread, so I'll add this report and start asking around!! I really hope someone is willing to help me out, I've put on the clamps and plugs already (as of 5:48pm) and my nipples are hurting again!!!

82:

Spoiler:

If I can fit a complete set of underwear (panties+bra) into my little asshole, I get to move forwards 1d10 squares. If not, I will move back 1d10 squares.

[SluttySarah]

6:35: I couldn't take it anymore and had to take off my nipple clamps They were throbbing in so so much pain as I was talking to dao_of_penguin but he suddenly left after he agreed to help me out!! Maybe this was delibrately to punish me a little, and regardless I failed the task. I will ask my Sir for punishment later, and anyone in this thread seeing this report is free to discuss a little punishment with me.

I rolled a 5, putting me on square 41. This square, made by my master, instructs me to roll two dice and work the big 2.36'' glass plug in and out of me that many times. I rolled a 5 and a 2, for a total of 7. It took some effort working the big glass plug in me 7 times, but my asshole is getting more and more relaxed and it took only about 10 minutes total. I just rolled a 4, putting me on square 45. I can take the free square... or take an enema wearing clover clamps to get a chance to earn a reroll in the future. I'm really scared of getting some snake in the future so I'll gladly take this opportunity. I am thinking about if this needs to be a 3L cleaning enema wearing my harsher clamps like my master wants. Since if I took the 2L enema, it would help clean me out and I would not need to take my 3L cleaning one, and that feels like cheating.

83:

Spoiler:

If I can stuff my old (quite small) two-piece swimsuit all inside me, I may move forward 1d15 squares. If I cannot, I will flip a coin and that half of the swimsuit will stay inside me for an hour