GrrlSpanky’s Anal Heaven dare

[squirter]

Hey guys
I am a male and i have never done anal and i need some anal stretching because i see my hole is too tight..Can you please tell me if i can try this dare for the first time?And how will it feel? how many days my ass will be sore?
Please answer me as soon as possible because i want to know if i can try ...
Thanks

[GrrlSpanky]

If you dare . . .

Spoiler:

If you read this dare thinking you might try it and read this spoiler you must perform this roll within the next 24 hours:

Roll to determine how to insert your toy:
1. Slowly insert the toy, allowing yourself to relax around it as you go. You can only slide in and are not allowed to slide out.

Let’s get you warmed up . . .
2. 100 slow shallow strokes, no touching!

I bet you are craving more aren’t you? Try this round on for size:
4. 300 medium shallow strokes, rubbing your clit/stroking your cock.

Mmmm I wonder if you are wanting more after all that. Let’s find out . . .
1 - 2. Do the last round over again, applying lube as needed. Move on to the next round when done.

I bet you are just dying to cum aren’t you? Hmm your luck may not be with you. I like orgasm denial.
6. 6’s are Bad Luck – Fuck your ass hard for 5 more minutes and then stop. No cumming for you.

[squirter]

What about me? Will u answer me?

[MaleSlave04]

need a master/mistress to force me to play this game on skype, i will go on cam...


Skype - BallbustingSlavee

[slaveboy32]

A little background to how I am doing this first. Since I am terrible at not cumming while I complete these dares, I have opted to wear my chastity cage. So I am opting out of the option to cum at the end, regardless of my final roll. Also it will be hard to have the you that stimulates my penis with my cage on so I will add an extra 50 pumps to any step that requires it.

Roll 1: 1. Slowly insert the toy, allowing yourself to relax around it as you go. You can only slide in and are not allowed to slide out.


Ah, an easy start. I lubed up nice and good and just ever so slowly and gently I inserted the tip of my dildo in. I took it nice and slow, as I hadn't done any anal dares in a while and got it all the way in after about 4 or 5 minutes.

Roll 2: 4. 200 medium shallow strokes rubbing your clit/stroking your cock. Apply toothpaste/icy hot to your genitals before you start.

So right off the bat, I need to add an extra 50 stokes, given I can't stroke. I added toothpaste to my balls before I started the 250 pumps.
I did the pumps in groups of 50 and it was not so bad, the shallow and short pumps were actually quite enjoyable!

Roll 3: 6. 6’s are Bad Luck – 500 Hard, Fast, Deep strokes with your toy on and set to high

Ouch! Since again I can't really use my toy I am adding an extra 50 strokes to this. Also my dildo can vibrate so I will turn that on high too!
I am especially glad I had my cage on for this one. Between the hard and rapidly fast pumps and my vibrations on high, this was so much fun! I did this step in groups of a hundred. After 300 pumps I had to answer a surprise phone call, so I decided to cleanup a bit(it was getting kinda messy) then finish my last 250 strong! I did another 100 finished up with 150.

Roll 4: 5 – 6. 6’s are still bad luck – start the dare at the beginning. Move on to the next round when done.

oh no! So much more fucking, at least I'm all loosened up!

Start over!

Roll 1: 3. Slowly slide in the toy in and out inch by inch, with each stroke only going slightly deeper than the last until it’s as deep as it will go.

Not so bad, 9 pumps in and out is what it took for me to go as deep as possible

Roll 2: 1. 50 slow, deep strokes while rubbing your clit/stroking your cock.

since I can't stroke my cock I will again add another 50, making it 100 total.
This wasn't too bad. Hardest part of this was trying to keep all 100 slow. I did it slowly and almost all the way out and back in all the way.

Roll 3: 1. 150 slow strokes – all the way in and all the way out, savoring every one while rubbing your clit/stroking your cock.

Damn my stupid rule... This time I will change it up. This time instead of adding extra strokes I am going to make it more savory and turn on the dildo vibrations to medium.
So again, the hardest part of this was keeping it slow, but it sure did feel amazing!


Final Roll!: 1. Take out the toy. Pleasure yourself for another 30 minutes however you please, and cum hard at the very end.

Well this is super easy. I just took my toy out, and can't pleasure myself so this is, finally the end!

[lisabigboobs]

Roll to determine how to insert your toy:
6. 6’s are Bad Luck – slam the toy in hard and deep all in one go.

Mmm Now that feels so good doesn’t it, being nice and filled by your toy? Let’s get you warmed up . . .
4. 200 medium shallow strokes rubbing your clit/stroking your cock. Apply toothpaste/icy hot to your genitals before you start.

I bet that ass feels nice and warm now. Reapply lube now if necessary. I bet you are craving more aren’t you? Try this round on for size:
3. 250 medium speed, all the way in and all the way out with your pussy/penis toy on set to medium.


Mmmm I wonder if you are wanting more after all that. Let’s find out . . . .
3 – 4. Move on.

I bet you are just dying to cum aren’t you? Hmm your luck may not be with you. I like orgasm denial.
6. 6’s are Bad Luck – Fuck your ass hard for 5 more minutes and then stop. No cumming for you.

[lakana]

I really loved this dare...

6. 6’s are Bad Luck – slam the toy in hard and deep all in one go.
I haven't played in a while so I was good and tight. This was like jumping into a cold pool... Yikes!

2. 100 slow shallow strokes, no touching!
This was nice... much easier... I was concerned this dare was going to get difficult really fast, but this step was easy.

3. 250 medium speed, all the way in and all the way out with your pussy/penis toy on set to medium.
Yep, it's getting harder... much harder.... Still enjoying, but I was fighting the urge to climax about halfway through this step

6. 6’s are still bad luck – start the dare at the beginning. Move on to the next round when done.
OH NO!!

5. Apply a toy to your clit/penis set to high. Slide the toy in veeeeeeeeery slowly until it’s as deep as it can go. You are not allowed to cum. Turn off or take the toy off when fully inserted.
I foresee failure in my future.... The added toy alone just about pushed me over.

6. 6’s are Bad Luck – 300 Hard, Fast, Deep strokes with your toy on and set to high.
Yep, that's it. I lost it at about 98... **FAIL**
I made myself continue though, with the exception that regardless of my last “roll”, it will be a 6.

5. 400 deep strokes. Start slow and build the speed to the very end. Wear your pussy/penis toy set to high. Apply toothpaste/icy hot to your genitals before you start.
I used icy hot on my pussy, and between that and the toy and having gone over already, my pussy was on FIRE. It was massively sensitive and burning. I made it through though... Oww...

6. 6’s are Bad Luck – Fuck your ass hard for 5 more minutes and then stop. No cumming for you.
Hah, I rolled a 6 anyway... I was already prepared for this one though so it wasn't really a letdown.

I will have to try this one again... and try NOT to fail next time.

Thank you for the dare!!

[Fantage]

want to try this but don't have a butting or dildo any alternatives?

[DaDaTzz]

3. Slowly slide in the toy in and out inch by inch, with each stroke only going slightly deeper than the last until it’s as deep as it will go.
4. 200 medium shallow strokes rubbing your clit/stroking your cock. Apply toothpaste/icy hot to your genitals before you start.
3. 250 medium speed, all the way in and all the way out with your pussy/penis toy on set to medium.
2. Do the last round over again, applying lube as needed. Move on to the next round when done.
2. Leave the toy in. Cum twice and then you may remove the toy and cum a third time.

I did this dare as part of the "butt slave for a week slave". My ass wasn't really trained to take my medium size dildo right away, so it was a bit painful to put it in. The second part I had to stroke with toothpaste, doesn't really do much on me, except getting messy. I actually don't understand that whole maze with toothpaste, but well, it's probably only me.
Part 3 was rather tough as I had to do 250 pumps; the last hundreds were quite intense !
On part 4, as I got a 2, I had to redo the part 3 again, which meant another 250 pumps in my ass. It was surprisingly a lot easier to take, as my ass gaped and got used to the dildo, so it was actually nice and pleasurable, though far from the intensity of the last round.
For the last part, I had to cum twice with the toy inside me, before being allowed to remove it and cum a third time. This was really tough for me as it's hard for me to cum several times in a day. I had to keep the dildo for about an hour in my ass, before feeling my self ready for the second round. As I am writing, I am strocking for my third cum and my balls are hurting like hell !

[Dice7]

Originally Posted by GrrlSpanky

This dare is a takeoff from the ever so popular SexDemon’s Anal Hell. I find this dare quite enticing and always thought it would be a very satisfying and fulfilling anal dare if only you could use copious amounts of Lube. Soooo Here is my shot at an anal dare that is challenging, but enjoyable.



For this dare, you should be naked UNLESS: If you have cross dressing in your likes – Then you must do this dare in panties and a bra. The panties can be pulled down below your butt or move them to get access.

You will need – Your favorite ass fucking object, one die, lube, toothpaste or icy hot, and a toy that stimulates your pussy/penis, preferably without penetration (for you females).


First – Lube your Dildo! Apply lube as needed throughout this dare. No need to get permission!!

Roll to determine how to insert your toy:

Spoiler:

1. Slowly insert the toy, allowing yourself to relax around it as you go. You can only slide in and are not allowed to slide out.
2. Coat your clit/head in a thin layer of toothpaste or icy hot. Slowly insert the toy.
3. Slowly slide in the toy in and out inch by inch, with each stroke only going slightly deeper than the last until it’s as deep as it will go.
4. Slide the toy in and out going slightly deeper with each stroke. Rotating it as you slide it in and out until it’s as deep as it can go.
5. Apply a toy to your clit/penis set to high. Slide the toy in veeeeeeeeery slowly until it’s as deep as it can go. You are not allowed to cum. Turn off or take the toy off when fully inserted.
6. 6’s are Bad Luck – slam the toy in hard and deep all in one go.

Mmm Now that feels so good doesn’t it, being nice and filled by your toy? Let’s get you warmed up . . .

Spoiler:

1. 50 slow, deep strokes while rubbing your clit/stroking your cock.
2. 100 slow shallow strokes, no touching!
3. 150 medium speed deep strokes with your pussy/penis toy on set to medium.
4. 200 medium shallow strokes rubbing your clit/stroking your cock. Apply toothpaste/icy hot to your genitals before you start.
5. 250 deep strokes. Start slow and build the speed to the very end. Wear your pussy/penis toy set to high. Apply toothpaste/icy hot to your genitals before you start.
6. 6’s are Bad Luck – 300 Hard, Fast, Deep strokes with your toy on and set to high.

I bet that ass feels nice and warm now. Reapply lube now if necessary. I bet you are craving more aren’t you? Try this round on for size:

Spoiler:

1. 150 slow strokes – all the way in and all the way out, savoring every one while rubbing your clit/stroking your cock.
2. 200 slow shallow strokes, no touching! Apply toothpaste/icy hot to your genitals before you start.
3. 250 medium speed, all the way in and all the way out with your pussy/penis toy on set to medium.
4. 300 medium shallow strokes, rubbing your clit/stroking your cock.
5. 400 deep strokes. Start slow and build the speed to the very end. Wear your pussy/penis toy set to high. Apply toothpaste/icy hot to your genitals before you start.
6. 6’s are Bad Luck – 500 Hard, Fast, Deep strokes with your toy on and set to high.

Mmmm I wonder if you are wanting more after all that. Let’s find out . . .

Spoiler:

1 - 2. Do the last round over again, applying lube as needed. Move on to the next round when done.
3 – 4. Move on.
5 – 6. 6’s are still bad luck – start the dare at the beginning. Move on to the next round when done.

I bet you are just dying to cum aren’t you? Hmm your luck may not be with you. I like orgasm denial.

Spoiler:

1. Take out the toy. Pleasure yourself for another 30 minutes however you please, and cum hard at the very end.
2. Leave the toy in. Cum twice and then you may remove the toy and cum a third time.
3. Leave the toy in and wear the clit/penis toy on high, humping and rubbing for 20 minutes. You may not cum. Take off the toys.
4. Leave the toy in and wear the clit/penis toy on high, humping and rubbing until you cum. Leave the toy in your ass for another 30 minutes and then you may remove.
5. Hoew many times did you fuck your ass? If more than 500, you may cum any way you please. If less, edge 3 times and then the dare is over – no cumming.
6. 6’s are Bad Luck – Fuck your ass hard for 5 more minutes and then stop. No cumming for you.

A dare partner of me and my wife is giving this a try as part of an agreement we had. She doesn't really enjoy anal normally. Using an 8 inch dildo with a condom on it

She slowly inserted it roaring it until it was all the way in she gasped and groaned the whole time and took almost 2 minutes


She had to cover her pussy in toothpaste she moaned she thought this was meant to be heaven! We counted for her as she did 200 medium shallow strokes while playing with her pretty clit. She was very quiet Apart from heavy breathing


With her vibe on her clit she tried 400 deep strokes starting slowly she moaned she couldn't do it but we encouraged her and I guess her clit took over as she started to get a bit faster. The last 20 or so she was grunting and her ass was slapping hard against her little ass as she rapidly fucked her hole.

She had to go again 200 slow shallow strokes with no touching but more toothpaste on her minty fresh snatch, she enjoyed it a lot less without the stimulation on her puss

Now she has to leave the toy in (she's sitting on it!) and she is rubbing the vibe on her clit as she humps one of our sofa cushions! She needs to cum then leave it in 30 mins, which she isnt looking forward to

[slaveboy32]

So for training for a dare I'm doing tomorrow (watch my blog) I'm doing some anal threads for practice, do I figured I would start easy.

Heads up in in chastity so any pleasure to the cock was not done and instead went to my ass.


Roll 1: 3. Slowly slide in the toy in and out inch by inch, with each stroke only going slightly deeper than the last until it’s as deep as it will go.

So not a bad start to this one, I crouched down and started the insertions. I got in about an inch, and all the way back out, in about two inches, out one, in three, out 4; I repeated that until I had the dildo as deep as I could fit it in my ass


Roll 2: 6. 6’s are Bad Luck – 300 Hard, Fast, Deep strokes with your toy on and set to high.

So as I'm in chastity, I can't really set a toy to high on my dick, plus the only vibrating toy I have is currently being used balls deep in my ass, I just set that one to high and went to town with the 300 pumps; fast and deep.
So I got in a position where I could get easy access but still have a nice view to the show (on my dice with my leg up) and went to town. I did them all non stop but counted in groups of 50. Around 200-250, I was feeling so much pleasure, I messed up the count, so I ended up doing an extra 50. After they were finished, I had to pause and clean up a bit, so after cleaning, I reinserted the dildo using 6 from the first round and just roughly shoving it in.

Roll 3: 4. 300 medium shallow strokes, rubbing your clit/stroking your cock.

Again chastity, so I just set the dildo to low and went to work, in the same position as above.
The feeling I got from this round was intense! The first hundred or so seemed like it would suck compared to last round, but then as I kept going, it kept feeling like I had to poop and my body in voluntary kept pushing but I kept that dildo firmly in there and the feeling was amazing!

Roll 4: 3 – 4. Move on. (3)

i was actually kinda nervous here... I didn't want to start over or go back, but I got lucky!

Roll 5: N/A

i don't get to cum so this roll was not applicable to me, I just left to toy in my in high while I wrote this report.

[ryan1010]

I'll try this later, sounds interesting...

[DaisyFae]

I need to do this! I'll try this weekend

[DaisyFae]

So, I got a chance to this dare and I sent proof to Slaveboy32 so he could keep me accountable. So here’s my report.

3…slowly slide the toy in and out inch by inch. God this felt so good. I had been edging all day and had already came twice, but I had been thinking about this dare all day and was more than ready to begin. The “slowly” part about killed me because I just wanted to feel my ass fill up. Finally I thrust it deep as it would go. Relief!

4…200 medium shallow strokes rubbing clit and applying toothpaste before. I love toothpaste on my clit, so I was very excited about this. It was hard to focus with the cold burning sensation on my clit and the feeling of being full and then not. I wanted to go deeper, but I tried to stick to the shallow strokes. I lost count once, so I went back to the lowest number I could remember and kept going. I was getting so wet and I had to stop for a few seconds or else I would have finished way too early. I tried to focus on counting, but I kept moaning and panting as I worked.

5…400 deep strokes with toy on high and toothpaste. I reapplied lube here, but I’m not sure it was entirely necessary. I taped my vibrating egg to my clit and started going to work. As I messaged Slaveboy32, I almost lost it five strokes in. It felt so good, but so intense. There were so many sensations to focus on. I was panting like crazy at this point as I tried to keep count. It was so hard to focus on the counting when all I wanted to do was cum. I was humping my bed while I finished the strokes and biting my pillow to keep from calling out.

3…Thank god. I don’t think I could have redone everything without finishing. I think between all the strokes I had gotten myself to an edge close to a dozen times. I was begging to cum at this point.

1…Damn! I took the toy out and started playing with myself humping the floor and grinding on the bed. I came quickly and as a punishment I decided I should have to continue. My ass was gaping, my pussy dripping, and my clit calling out for me to stop, but I continued playing with myself, even leaving the vibrating egg on my clit. I came again at the very end and honestly just laid flat out on my bed for a long while.

Amazing dare! I'll probably revisit this again when I have another free night.

[DLdapper]

1 6 3 4 6

Was fun, will come back for more. c: it helps me a lot with my anal training and milking.