Anal stretching dice dare... Are you buttslut enough?

[Simi]

Hi my fellow anal sluts! I wanted to write this task for those nights when you know you want to be fucked/stretched… but you don’t want to make the choices. If this sounds good to you then you are in the right place!

There will be some optional bonus orders in spoilers. If you open them you must do it if it's within your likes/limits and is realistically possible at that stage. There will be some rewards, and some more evil tasks amongst them. If you have any feedback on having these optional tasks I would like to hear, especially if you have ideas for more.

What you will need:
Some time (There is some RNG involved if you let a dice pick, you may choose however which means you can get through in just 3 rounds of fucking, you could also wind up fucking for hours)
A six sided dice/random.org
A lot of lube
3 or more dildos/other phallic objects which are progressively bigger in size(You can use plugs/everyday objects if needed)
Some body awareness (listen to your body, if its getting too much and you need a breather/to rest around the toy it's ok)

I want you to make sure you stay safe during this, a little tender is ok but please avoid damaging yourselves/tearing anything. Before any rapid/rougher fucking I recommend you insert as fully as comfortable and let your body stretch around it for a few minutes. Do everything at your own pace

The aim of this dare is to give you a framework for feeling nicely stretched, without hurting yourself. If a task isn’t possible at that point gently fuck with whichever toy it is you are wanting to fuck/rest with it in for a few minutes, let your body get used to it. Before either attempting that task again or going down a round.

I have aimed this to be realistic, based on my personal experiences but if you are very new to anal it could still be too much. (Or if rng is not in your favour) Please be careful, listen to your body. There is no point training a fuck toy whose holes are out of action afterall

Round 1

Time to start out with the small toy. Ideally this should be a toy that you can easily take without a warm up, but it is enough that it will loosen you for the next one. Then, pick or roll 1 of the following:

1. Fuck yourself gently on this smallest toy, while pleasuring the other two for 10 minutes (stroking them/sucking them etc)… This dare is going to have you embracing your anal slut side so why not start it off right
2. Do 10 slow strokes, followed by 10 fast ones and repeat until you hit 100 strokes
3. Do 50 fully in and out strokes, any pace

Spoiler:

You seem to be a curious slut? After this fucking be curious and check how stretched you are with your hand, test how many fingers fit and how deep you can get. Pull your arse open (gently) and enjoy the feel of being loosened. Do this after every round

4. Spend 10 minutes fucking the toy however you'd like
5. Do 30 very slow very deep thrusts

Spoiler:

Curiousity killed the cat… girls before each round of fucking you must slap your cunt 10 times

6. Spend 5 minutes fucking that toy as frantically as you can, before rolling for this round again. You must also complete that roll before progressing

If you struggled with this first round: remove the toy. Give your hole a few minutes rest before reapplying lube generously and doing another task from this round.

Spoiler:

Bonus penalty, spend the rest time sucking/licking the toy or spanking your arse an appropriate amount

If you took your warm up fucking like a good anal toy:
Congratulations, you may take a few minutes break (either with the toy in or out, your choice) before progressing.

Round 2

Time to insert the next toy size up, lube generously and insert it as deep as you can (gently) Once you are as deep as you can get stay there on it, to get your hole ready for a fucking. You may if not denied pleasure yourself for 5 minutes while the toy inside you before rolling.

1. Pick any anal fucking video, spend 10 minutes attempting to replicate it as best as you can
2. Spend 5 minutes fucking yourself in any position whilst moaning aloud that you need someone to use your arse roughly.

Spoiler:

Slap yourself (anywhere is a valid target, face, balls, cunt, arse cheeks, thighs etc, you can change targets) each time a cock leaves your arse for the rest of this dare. Let's hope you don't roll too many of the full in and out fucks.

3. Do 100 fully in and out strokes, any pace
4. Do 20 fully in and out strokes with the medium toy, then remove it and suck on that cock while you do 60 thrusts with the small toy (If atm is again your limits thats ok, gag yourself with something else if possible for the smaller toy fucking)
5. Do 40 very slow very deep thrusts. I want every thrust in to be at the max depth
6. Spend 5 minutes fucking that toy as frantically as you can, before rerolling for this round

Spoiler:

Getting fucked is thirsty work! Go fetch a small glass of water and drink it before you can move on. You can moan better hydrated ;)

If you struggled with this second round:
Remove the toy. Give yourself a few minutes rest before inserting the small dildo. Lube well before giving yourself 30 fully in and out thrusts. I want you to take your time, but I want the head of the cock out of your arse between each thrust. If you can be rough go for it. Once you have completed this you will reroll for round 2.

Spoiler:

Bonus penalty, keep the small toy in your mouth after those fucks while you repeat round 2

If you were a good fucktoy:
Congratulations, you may take a few minutes break before moving on. You may choose to repeat this level if your arse needs more warming up before the large toy

Spoiler:

Spend up to 5 minutes filled with your toy and teasing yourself. Edging is encourage, cumming is not

Round 3

You are hopefully feeling a little looser by now, Insert your large toy and slowly work it in deeper/gently fuck it to get your arse a bit more used to it. Once it feels like you are ready for a fucking. Before rolling I want you to bounce a little on the toy, only maybe sliding it in and out an inch or so

1. Find an anal fucking video between 5 and 20 minutes long and attempt to match the pace set.
2. Insert and remove without using your hands 25 times

Spoiler:

Slowly stroke/tease your clit for the duration of this task

3. Do 50 fully in and out strokes, any pace
4. Fuck yourself for 5 minutes in doggy style while calling yourself a horny bitch

Spoiler:

After your fucking stay on all fours while keeping the toy in and hump something for a couple of minutes.

5. Do 30 very slow very deep thrusts
6. Spend 5 minutes fucking that toy as frantically as you can, before rerolling for this round

Aww is someone not yet stretched enough.
Its ok, give yourself 10 spanks to the arse saying I need to learn to be a better fuck toy. Once you have given yourself that spanking, take the medium dildo and do 50 fully in and out strokes with it to help loosen you up to repeat this round.

Did you finish your stretching like a good anal toy? Well done.
You may either progress on to round 4 for some bonus rough fucking or finish the dare here… If you opt to continue you may have to repeat everything again…

Round 4+
So you wanted to keep getting stretched huh? Roll 1d6 and do that many tasks from this list.
(Please do listen to your body if it gets too much. You also are welcome to come back to the fucking later in the day/rewarm up if needed to complete the dare)

This time if you are rolling 2 d6 to determine which bonus rounds you have to do before you are released from the task.

2. Well… in basically every dice game rolling 2 1s is unfortunate so to match the frustration and disappointment that roll normally gets you are going all the way back down to the smallest size in round 1, you are not allowed to touch yourself anywhere even if a task allows it until you are back to this round. I am curious how frustrating that small dildo feels right now…
3. Do 50 fully in and out strokes, any pace
4. Complete 50 fucks with each toy, your choice of order and speed
5. Do 30 very slow very deep thrusts

Spoiler:

Are you feeling nicely stretched by now? I hope so. Let's treat you like a dirty slut. Pick a porn type which turns you on but humiliates you, fuck yourself while watching a video (5mins+)

6. Spend 5 minutes fucking the large toy as frantically as you can,before adding an extra roll to your required count
7. Spend 3 minutes holding the toy in at its widest point
8. Fuck yourself for 5 minutes at any pace, whilst moaning like the anal slut you clearly are.
9. Do 10 fucks with the large toy before swapping to the medium. Give yourself 30 fast fucks before swapping back to the large toy and repeat (2 rounds)
10. Force yourself to take the toy as deep as you can, for 5 minutes. You may move/gently fuck with it to loosen but I want it stretching you as much as you can. Feel nice and full for me

Spoiler:

On the topic of feeling nice and full, I would like you to have a drink of at least 300mls and you are not allowed to piss for at least an hour/completion of this fucking session
If you come back to it a few days later thats allowed if you have many more rounds to do, but you must hold whenever you are fucking from now until the end of the dare.

11. Unfortunately sometimes us size queens get let down. Go down to the size(back to round 1), you are not allowed to touch yourself until you are back to this size toy. Yes this is mean… I was frustrated when writing it. lol

Spoiler:

Bonus penalty for the boys, if your cock is smaller than that dildo slap it every time you stop fucking until you are back to this size

12. Let's test how well your stretching is going. Spend 10 minutes seeing how much you can finger/fist yourself… I hope you are ready.

Did you complete all of those rolls? Well done you should be feeling pretty nicely stretched. Any reports/feedback will be very welcome. If any tasks had you under any restrictions they are all lifted (was that vague enough?)

Have you given up before the end but you made it to round 4? Good job, consider this fucking a warm up session. Attempt the dare again within the next week.

If you drop out of the task (other than for health reasons) before reaching round 4:
Clearly you aren't ready to serve as a fuck toy. You are going to spend 7 days - 1 for each roll successfully completed being cucked and frustrated.
Add that time to your denial if you can and are denied, if you werent denied you now are for that time.
When I say you are going to be cucked you are going to spend at least 30 minutes daily watching anal while not being permitted to touch at all (If you are already on porn restrictions, this is now censored anal) take notes on the positions, how people are getting fucked… embrace craving it. Do your best to mimic the reciever and focus on how good it would feel to be used. Report your failure to us.


Any reports are always appreciated, or suggestions for extra bonus tasks/alternate options in categories. Even simply feedback on the dare would be good to hear.

Happy buttsluttery and stretching!

[YourDarePartner]

I used my candle as small toy, my toothpaste tube as medium, and my deodorant can as large.

Round 1
4. Spend 10 minutes fucking the toy however you'd like
That was an easy start

Spoiler:

You seem to be a curious slut? After this fucking be curious and check how stretched you are with your hand, test how many fingers fit and how deep you can get. Pull your arse open (gently) and enjoy the feel of being loosened. Do this after every round

I was curious inserting two fingers was easy, a third stretched me a little.

If you took your warm up fucking like a good anal toy:
Congratulations, you may take a few minutes break (either with the toy in or out, your choice) before progressing.

Round 2

Time to insert the next toy size up, lube generously and insert it as deep as you can (gently) Once you are as deep as you can get stay there on it, to get your hole ready for a fucking. You may if not denied pleasure yourself for 5 minutes while the toy inside you before rolling.

It was not too thick, but I felt the last inch really deep during the first minutes.

2. Spend 5 minutes fucking yourself in any position whilst moaning aloud that you need someone to use your arse roughly.
Moaning and begging to be rougly assfuck turned me so on!

If you were a good fucktoy:
Congratulations, you may take a few minutes break before moving on. You may choose to repeat this level if your arse needs more warming up before the large toy

Spoiler:

Spend up to 5 minutes filled with your toy and teasing yourself. Edging is encourage, cumming is not

Arousing and frustrating!

Round 3

You are hopefully feeling a little looser by now, Insert your large toy and slowly work it in deeper/gently fuck it to get your arse a bit more used to it. Once it feels like you are ready for a fucking. Before rolling I want you to bounce a little on the toy, only maybe sliding it in and out an inch or so

The deodorant is thick, around 2.2", and really longer than the toothpaste tube.
It tooks time, but I inserted it almost 9" in my ass, boucing on it for going deeper.
I felt deeply filled.

5. Do 30 very slow very deep thrusts

I felt it so deep, a mix between pain and rough pleasure.


Did you finish your stretching like a good anal toy? Well done.
You may either progress on to round 4 for some bonus rough fucking or finish the dare here… If you opt to continue you may have to repeat everything again…

Round 4+
So you wanted to keep getting stretched huh? Roll 1d6 and do that many tasks from this list.

2

This time if you are rolling 2 d6 to determine which bonus rounds you have to do before you are released from the task.

9. Do 10 fucks with the large toy before swapping to the medium. Give yourself 30 fast fucks before swapping back to the large toy and repeat (2 rounds)

That was fucking good!

6. Spend 5 minutes fucking the large toy as frantically as you can,before adding an extra roll to your required count

My cock was milking during all this task!

6. Spend 5 minutes fucking the large toy as frantically as you can,before adding an extra roll to your required count

I was so aroused. If I had touched my penis, I would have cummed instantly.

7. Spend 3 minutes holding the toy in at its widest point

Not moving was frustrating as hell!


Thanks for the dare!