30m predicament bondage - each comment I'll sit on dildo 10x - Page 3

Messyone · 07-07-2023, 03:07 PM

Well that was an educating experience. First things first is that I failed. The thickness of the 9 inch dildo was too much to handle. It took a lot of warm-up to get myself mounted but I was not able to complete all the bounces. I got to about 100 before I just sat balls deep for the remainder of the time and released myself. I just finished the 240 spankings I deserve but have not the heart to put myself back on the dildo. I also was too excited and didn't get my legs over head for a facial. I'm at everyone's mercy.

Subnoctis · 07-07-2023, 04:30 PM

My punishment is as follows:
Put on nipple clamps. Edge yourself 10 times but DONT orgasm. Then give yourself 10 ball slaps. Put on chastity, leave on for 48 hours.

You can take the clamps off 10 min after you put on your chastity.

Bear21 · 07-07-2023, 05:04 PM

Honestly, I live how this has ended up.

Instead of punishment, I will offer encouragement. Count up the number of thrusts I have added, and each day you are to be locked and perform these thrusts (the one I added) I would also like a picture of that dildo in you and you locked, and also one of that destroyed ass with some sort of identifier.

As I don't see a list of limits, this is all negotiable.

Messyone · 07-07-2023, 05:34 PM

Quote:

Originally Posted by Subnoctis

My punishment is as follows:
Put on nipple clamps. Edge yourself 10 times but DONT orgasm. Then give yourself 10 ball slaps. Put on chastity, leave on for 48 hours.

You can take the clamps off 10 min after you put on your chastity.

Edges, slaps and chastity on. Timer for 10 minutes has started and I will yank them off when done. Can I take it off to clean and put back on before the 48 hours is up?

Subnoctis · 07-07-2023, 05:40 PM

You may clean up one time.

Messyone · 07-07-2023, 05:41 PM

Quote:

Originally Posted by Bear21

Honestly, I live how this has ended up.

Instead of punishment, I will offer encouragement. Count up the number of thrusts I have added, and each day you are to be locked and perform these thrusts (the one I added) I would also like a picture of that dildo in you and you locked, and also one of that destroyed ass with some sort of identifier.

As I don't see a list of limits, this is all negotiable.

Looks like you gave me 100 total before I closed the post Is that then 100 each day of chastity that subnoctis put me in? Or is more chastity coming my way? Also, is there any way I can perform on a smaller dildo? I'm not sure I can handle more of that monstrosity.

Unfortunately, I don't try to do pictures...

Messyone · 07-08-2023, 07:18 AM

Quote:

Originally Posted by Bear21

Honestly, I live how this has ended up.

Instead of punishment, I will offer encouragement. Count up the number of thrusts I have added, and each day you are to be locked and perform these thrusts (the one I added) I would also like a picture of that dildo in you and you locked, and also one of that destroyed ass with some sort of identifier.

As I don't see a list of limits, this is all negotiable.

Well since I didn't receive a response from you, i didn't want to disobey. It once again took some coaxing from my asshole but I got the monster dildo in and completed the 100 thrusts while in chastity on my bed. The difference between this and my original dare was that by using my hand to control it, I actually started to rub up against my prostate which felt so good I eventually went from slow to fast in hopes of an orgasm Unfortunately 100 wasn't enough and I stopped like the good boy I am which has left me quite horny and a decent amount of precum in my chastity cage.

So now my question is, did I complete the punishment or do I owe 100 for each day I'm in chastity?

Messyone · 07-08-2023, 07:45 AM

Quote:

Originally Posted by DimpleDump

I hope they are on the way now.

Since you also posted multiple times, you can choose to punish me for failing the bounces and not giving myself a facial.

DimpleDump · 07-08-2023, 10:40 AM

Punishment
I think you will do fine...

Uhmm.....

First of all... Congrats for your attempt! You did well!

But we still need you hump better. I actually wondered if you had done any enemas before humping it. So before you proceed, please flush your system!

Now, since you are able to do 100 times, I suppose we can do that again to learn how wide and deep it is. This time though, go slow. REALLY slowly and I mean it.

I want you to lean back as you do the following at every thrust in sequence:
//After you slide it in....//

Rock your bum forward then swing it slowly clockwise twice.
Pull out just a little bit.
Push in deeper than before.
Rock your bum forward and backward three times.
Pull it out to mid length.
Rock your bum forward then swing it slowly anti clockwise twice
Push back in.
Swing your bum clockwise and anti clockwise twice
Pull it back out just near the tip. Try to feel it! Don't you drop it out!

And this is 1 thrust cycle. Each thrust should take at least 6 seconds. Figure which part you like most! It's better than just sitting on it!

I don't know about your facial.... Just put it in your mouth the next time, then spit it out and rub them all over your face?????! But eww. And not really ewww actually.

Ewwwww.......

Messyone · 07-08-2023, 10:49 AM

Quote:

Originally Posted by DimpleDump

Punishment
I think you will do fine...

Uhmm.....

First of all... Congrats for your attempt! You did well!

But we still need you hump better. I actually wondered if you had done any enemas before humping it. So before you proceed, please flush your system!

Now, since you are able to do 100 times, I suppose we can do that again to learn how wide and deep it is. This time though, go slow. REALLY slowly and I mean it.

I want you to lean back as you do the following at every thrust in sequence:
//After you slide it in....//

Rock your bum forward then swing it slowly clockwise twice.
Pull out just a little bit.
Push in deeper than before.
Rock your bum forward and backward three times.
Pull it out to mid length.
Rock your bum forward then swing it slowly anti clockwise twice
Push back in.
Swing your bum clockwise and anti clockwise twice
Pull it back out just near the tip. Try to feel it! Don't you drop it out!

And this is 1 thrust cycle. Each thrust should take at least 6 seconds. Figure which part you like most! It's better than just sitting on it!

I don't know about your facial.... Just put it in your mouth the next time, then spit it out and rub them all over your face?????! But eww. And not really ewww actually.

Ewwwww.......

100 more?!?!

my poor hole is so sore already... I will try to complete another 100 tomorrow. I can't believe my ass is getting this much attention in just a few days.

Unfortunately I can't reach my mouth. I wish I was that flexible for self BJs... Would you like me to do something different with the facial idea?

DimpleDump · 07-08-2023, 10:56 AM

I mean... Just in your hands and go into your mouth! Not the flexible kind! **Faints**

You need not do it today. Just when you are feeling better...

Messyone · 07-08-2023, 11:00 AM

Quote:

Originally Posted by DimpleDump

I mean... Just in your hands and go into your mouth! Not the flexible kind! **Faints**

You need not do it today. Just when you are feeling better...

You're so kind!

I'll make sure to ruin it so as to not give myself any pleasure in this punishment.

07-07-2023, 03:07 PM	#31
Messyone Member Join Date: Jun 2019 Posts: 76 Blog Entries: 1	Well that was an educating experience. First things first is that I failed. The thickness of the 9 inch dildo was too much to handle. It took a lot of warm-up to get myself mounted but I was not able to complete all the bounces. I got to about 100 before I just sat balls deep for the remainder of the time and released myself. I just finished the 240 spankings I deserve but have not the heart to put myself back on the dildo. I also was too excited and didn't get my legs over head for a facial. I'm at everyone's mercy. __________________ Likes: WAM, sploshing, gunge, wedgies, anal, spankings, cum eating, enemas, diapers, private humiliation, light BDSM Dislikes: public, heavy pain, edging, CBT Toys: nipple clamps, clothespins, suction dildo, belt, butt plug, ball gag, handcuffs, chastity cage, sissy underwear

07-07-2023, 04:30 PM	#32
Subnoctis Junior Member Join Date: Jul 2023 Posts: 15 Blog Entries: 1	My punishment is as follows: Put on nipple clamps. Edge yourself 10 times but DONT orgasm. Then give yourself 10 ball slaps. Put on chastity, leave on for 48 hours. You can take the clamps off 10 min after you put on your chastity. __________________ 34 / M / Bi/ Switch Likes, Dislikes, Limits, and Toys

07-07-2023, 05:40 PM	#35
Subnoctis Junior Member Join Date: Jul 2023 Posts: 15 Blog Entries: 1	You may clean up one time. __________________ 34 / M / Bi/ Switch Likes, Dislikes, Limits, and Toys

07-07-2023, 05:04 PM	#33
Bear21 Distinguished Member Join Date: Aug 2021 Posts: 812	Honestly, I live how this has ended up. Instead of punishment, I will offer encouragement. Count up the number of thrusts I have added, and each day you are to be locked and perform these thrusts (the one I added) I would also like a picture of that dildo in you and you locked, and also one of that destroyed ass with some sort of identifier. As I don't see a list of limits, this is all negotiable.

07-08-2023, 10:40 AM	#39
DimpleDump Junior Member Join Date: Jul 2023 Posts: 29 Blog Entries: 1	Punishment I think you will do fine... Uhmm..... First of all... Congrats for your attempt! You did well! But we still need you hump better. I actually wondered if you had done any enemas before humping it. So before you proceed, please flush your system! Now, since you are able to do *100 times, I suppose we can do that again to learn* how wide and deep it is. This time though, go slow. REALLY slowly and I mean it. I want you to lean back as you do the following at every thrust in sequence: //After you slide it in....// Rock your bum forward then swing it slowly clockwise twice. Pull out just a little bit. Push in deeper than before. Rock your bum forward and backward three times. Pull it out to mid length. Rock your bum forward then swing it slowly anti clockwise twice Push back in. Swing your bum clockwise and anti clockwise twice Pull it back out just near the tip. Try to *feel* it! Don't you drop it out! And this is 1 thrust cycle. Each thrust should take at least 6 seconds. Figure which part you like most! It's better than just sitting on it! I don't know about your facial.... Just put it in your mouth the next time, then spit it out and rub them all over your face?????! But eww. And not really ewww actually. Ewwwww.......

07-08-2023, 10:56 AM	#41
DimpleDump Junior Member Join Date: Jul 2023 Posts: 29 Blog Entries: 1	I mean... Just in your hands and go into your mouth! Not the flexible kind! Faints You need not do it today. Just when you are feeling better...