A sub in virtual chastity, and oh-so-desperate to cum!

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Nice, and nice addition of the collar connected to the top of the spreader bar. And just how long did you last in that one, and how did you end up getting out of it? Was it an interrogation or similar type of challenge, or more of just a safe word and you were let out...that kind of thing?

Posted by Admin 06/19/2022 - 18:19
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Again, boy cannot realize how lucky he is. Thanks for sharing
Posted by Bondagebuddy2 06/19/2022 - 16:59
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Lucky, lucky slave

Posted by Bondagebuddy2 06/19/2022 - 16:56
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Have been in that last position. It looks quite simple but is as tough as hell after just a short time. Collar connected to the top of the spreader too, just for extra sport....

Posted by cbr998 06/19/2022 - 14:58
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To please the coach is all that matters. To be in chastity ans edged would be ecstacy.

Posted by footsoldier 06/19/2022 - 12:39
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Click on the pics below to enlarge them, and to animate any GIFs

This one is from a few years back with my very special boy down under, so he couldn't have possibly been located further away. That meant most methods of play were off the table at the time. But he wanted to play so badly, to feel Sir's control and creative, devious mind. But was he about to bite off more than he could chew?

So one day I decided to put him in "virtual chastity", something I'd typically never do because let's face it...most subs would get too horny and whether or not they want to obey their Sir, their horniness may get the best of them. But we had known each other for quite a while, I knew he was a very good boy, and I knew I could trust him, so I gave it a go. However, just because he was a very good boy doesn't mean he couldn't get a little whiney about his desperation to cum.

So he just miiight have gotten a bit whiney one day, and he just miiight have complained about wanting to cum one too many times. He might have even made the mistake of telling me that he "needed" to cum...big mistake! You don't "need" to cum boy, you're just more desperate to cum than you've ever been in your life! Maybe that's partially because of the things I've been doing to make you horny, and keep you horny? *evil grin!*

So I decided to give him an opportunity to cum...at a price! But what did I make him do to earn that privilege? After all, we all know that being allowed to cum is a privilege for any sub in chastity, virtual or not. I could allow it, or I could punish him for whining by not allowing him to cum for another 2 weeks before he was given another opportunity. But, I gave him a way to earn the privilege. How did I do that?

Take a look at the pics and see if you can figure out what I made him do to earn the privilege of jerking off. For those of you who know me fairly well, you already KNOW I didn't make it as easy as it may appear at first look. Let us know in the comments below what you think he had to do.

Tags: Chastity, Interactive

Comments36

MotoMike on April 29, 2020 17:20

i would bet that the note was written with his hard cock on all those pieces of paper, using alternating paints. It doesn't look like a work of art, but maybe if you made him write many many notes he'd get better? <evil grin>

Admin on April 29, 2020 19:49

Excellent first guest! And also, a correct first guess. That's exactly what I made him do. Although it may sound a lot easier than it was. He took a video of the entire thing for me. I'm sure he wanted to show me what a good boy he was, and that he didn't try to cheat in any way. Or maybe it was because I told him I wanted to see it on video, just to make sure. Never know how hard that might make his cock, and a sneaky boy might try to sneak in a few strokes before he's earned it. ;-) By the end of the video, or even quite a bit before the end, I could see the sweat dripping off of his naked body...showing what an exhausting task it was for him. On the plus side though, it was a great workout! The boy probably could have skipped the gym for a few days after that one, haha.

MotoMike on April 30, 2020 10:20

I like the alternating colors as well, it shows he was still able to think, which, let's face it, is always a challenge when denied and constantly using it as a human Sharpie.

PuppyKaiden on May 01, 2020 00:12

Yip, I was told to use two alternating colours but what they were was up to me. I chose red and blue because they're Sirs two favourites.

Admin on May 01, 2020 17:50

I said it before and I'll say it again...he's such a good boy! He even chose to use my favorite colors, instead of his favorites or whatever he was able to most easily find. He's almost like a loyal puppy. (Oh wait...he IS a loyal puppy! Loyal PuppyKaiden!) ;-)

fingrfethr on April 29, 2020 17:22

I can't get much from the first 2 pics, but I'll guess that the "ransom note" had to be written in multicolors with the boy's dick, possibly with other conditions as well.

Admin on April 29, 2020 20:16

Exactly! Hmm, what "other conditions" would you suggest for this one...or if it were your sub, what other conditions would you add? ;-)

fingrfethr on April 30, 2020 01:36

This is way out of my wheelhouse. I am curious to see the rest of those first 2 pics and how they fit in to the story. You got a video, you say? Did he do all of the reds, then all of the blues? Or did he have to wash off his dick after each letter? (And what kind of paint was it?)

Admin on April 30, 2020 09:16

Yes, he recorded the entire thing on a video for me. Need to keep a good (and super horny) boy honest, right? He actually did all of one color first, then all of the other color after...which some Doms just might consider to be cheating. However, he still had to coordinate things to ensure he did all of the right letters in each color, at the risk of having to redo it all if not. So it was a bit easier/less time consuming for him, at the risk of being A LOT harder and more time consuming if he calculated things wrong. And as for seeing the rest of the first 2 pics...you'll see those in Part 2, as well as some animated GIFs of him actually painting the letters. When you see that, I think you'll get a pretty good idea of just how exhausting this task was for him...much more exhausting than even he thought it would be. It takes a very good, responsible, and obedient boy to finish such an exhausting task and not quit part way through. ;-)

cbr998 on April 29, 2020 17:24

I think you made him into the new Da Vinci, using the only "brush" he had to hand, And of course all the time he was "painting" he got hornier and hornier. If I'm right then he would have been screaming inside for release by the time he got to the Question mark. But as he got the Y round the wrong way I doubt if you gave in that easily..

Admin on April 29, 2020 23:17

Haha, I love your reference! ;-) And yes, I typically like to let the punishment fit the crime...and similarly, when I'm making a sub earn something that he so desperately wants, especially if it's as a result of him whining for it too much. So in order to earn the right to cum, I made him do something that I knew would only make him even hornier, with his dick dragging across the pages, the sensitive head that could hardly take anymore stimulation without being authorized to finish himself off. But he knew if he didn't do it, he would have absolutely no chance of getting my permission to cum. So regardless of whether or not it would make him 10 times hornier, he did it anyway. Regarding the Y sloping in the wrong direction, what do you think an appropriate punishment would be for that? Or, just not let him cum for another (?) hours/days/or?

CharlesWbtm on April 29, 2020 20:04

He really wanted to please you! Looks like a lot of hard work was he doing it hands free like push ups and moving his dick over the paper?

Admin on April 29, 2020 22:48

Yeah, kind of like that. I think sometimes using just one arm to hold his body up though. Otherwise his dick would have been dragged too low across the paper and made a mess. And he knew that I expected quality work from him. He actually told me he ended up redoing a few of the pages because he felt it wasn't good enough to submit to me as it was. He's such a good boy! ;-)

CharlesWbtm on April 30, 2020 14:12

Yes he is definitely a VERY good boy! And sexy too! :-)

Admin on April 30, 2020 18:16

Yes, he indeed is a very good boy. Maybe you'll see more of him in the future here. He did visit me for a few days a while back, so he even got to have some in person fun in my playroom, not just remote with video proof. More like the kind involving real cuffs, real heavy wooden ungiving stocks that there's no escape from, a real DEEP adjustable dick gag, etc. *evil grin*

cbr998 on April 30, 2020 04:15

Maybe correcting the Y 5 times on more paper by writing the whole word each time? This time no hands ( if indeed he had hold of his cock to aim it in the first place). Should make it easier to support his body - both arms - but harder to actually see what he as doing at waist level.

Admin on April 30, 2020 10:20

Oh wow, you'd make him write the whole word all over again 5 times eh? Harsh, but probably appropriate. I'll bet he would never submit a Y like that again after that experience! (Or any other letter that wasn't properly cock-painted either.) ;-) And if I recall correctly, I don't think he used his hands to hold his dick the entire time. I'm pretty sure that was a rule of mine, no hands allowed anywhere near his dick while painting I mean if you think about it, if he was working hard to earn the right to touch his dick, he shouldn't be able to touch it in the process of earning that right, agreed? But I'll have to find that video and check it to be sure. If he did touch his dick at any point, maybe I should still punish him now, even though it's years later? I wonder what the statute of limitations is for improper cock painting punishments? Is anyone out there a kinky lawyer? *grin*

cbr998 on April 30, 2020 12:33

Ah. I didn't get that he couldn't use his hand to hold his dick while painting. In the pics that you have released it looks as if his arm goes down to do some "directing". But I slightly disagree with you about earning the right to touching his dick. His aim was to be able to cum, so having it in his hand whilst painting and still not allowed to get anywhere near an orgasm would have been even more torture. BTW the statute of limitations for improper cock painting is 1350 years, you'll be fine :)

Admin on April 30, 2020 15:29

I see your point, and agree that I could've tortured him more by allowing him to touch his dick while doing this task (but still not allowed to cum). Or, maybe I should have even REQUIRED that he touch his dick? Or maybe a more specific rule, like each time he went to touch it, he must wrap just two fingers around the base and slowly slide them toward the head, then hold his dick at that spot and direct his dick to paint the letter? Oh and thanks for confirming the statute of limitations on punishment for improper cock painting. ;-)

Master46307 on April 30, 2020 10:37

Next time you want to make it hard on the sub, make him paint it on real COURSE sandpaper (he, he). And make each letter the whole 8 1/2 x 11" sheet!

Admin on April 30, 2020 13:10

Oh WOW! That would definitely add a lot more challenge to it for sure. Have you ever made a sub do something like that? I'm assuming in that case, the best, and safest method would be a lot of up and down motions, sort of dropping the head of his dick on the sandpaper to blot the paint down, then lift up, move slightly up or down, then drop it down again to blot another circle of paint, and repeat to very slooooowly form the letters. Trying to make it go faster by dragging his dick on the sandpaper I'm sure would prove to be a major regret later. Using this method would be safer, but it would probably also feel like he was doing literally hundreds of mini pushups in the process.

jimmycontour on April 30, 2020 17:39

Also worth noting: Isn't paint generally kind of cold? I wonder how that factored in. haha

Admin on April 30, 2020 19:14

Hmm, are you thinking kind of a blue balls torture type of situation? Dick gets hard, dick gets dipped in cold paint, dick goes down a bit, dick drags along paper and starts getting hard again, dick has to be redipped in cold paint and gets a bit softer, rinse and repeat? Seemingly endless cycles of that? ;-) Or did you have something else in mind?

jimmycontour on April 30, 2020 19:33

It just seems like that's the likely scenario. :-)

PuppyKaiden on April 30, 2020 23:56

I can assure y'all, that I did not touch my dicklet during the entire process haha. As you note @cbr998, my hand drops down to hold the page. Imagine doing a push up, one handed, the other holding a page in place and then trying to shift around to paint.... I was a sweating, panting wrek by the end of the 25min it took - haha I can't believe we never saw the "Y" hey Sir! I do quite like the sandpaper idea but then again, I'm kinda a maso sooooooo *don't try this at home kids*

cbr998 on May 01, 2020 04:23

If Puppy Kaiden was such a panting sweaty mess at the end of the art lesson perhaps to finish off and to recompense for the Y maybe allow him to jerk off with rules. 1 Once he grabs his cock he's not allowed to let go. 2 He can wank as slowly or quickly as he likes but is not allowed to actually stop moving his hand. 3 He must not cum inside of 15 minutes. If he does then one week is added to his chastity for every minute left of the 15. He could video this for you for insurance purposes.

Admin on May 01, 2020 10:11

Excellent idea, I like your rules! I was just talking to him about this last night and he was hinting at wanting to do something soon, even during quarantine in a safe, remote way. So if we do, maaaybe I'll put some of these ideas to good use (potentially along with another idea I came up with a while back, which he was very eager to try, and did try at the time)...Hint: It involves chastity and has a similar sensation to the sandpaper idea mentioned here, but without him having to move his entire body to feel it. But he won't know which ideas or just how I will implement them until it happens. So I have one question for PuppyKaiden...Are you panting in suspense boy? ;-)

PuppyKaiden on May 01, 2020 20:00

Panting..... Throbbing..... Dripping.....

PuppyKaiden on May 01, 2020 19:59

D-e-vi-ous!

MotoMike on May 04, 2020 12:14

Good rules - would be an agonizing 15 minutes for the sub after waiting so long and thinking about the consequences of failure.

cbr998 on May 02, 2020 05:15

Velcro? I loved the pictures of that a few weeks back.

Admin on May 02, 2020 13:02

Velcro? In a chastity cage?? Wow, what an evil, sadistic guy you are! (Um, I mean, yup...you got it, that's exactly what I did with him. I guess I can be a sadistic guy too?) ;-) It was pretty entertaining too...he thought he could cum that way, so he tried to...then got super hard, but every time before he could get far enough he would feel his dick pressing into the spikes at the end of the chastity cage again, and go down a bit. Rinse and repeat, a vicious cycle!

baltsubboy on May 25, 2020 19:18

You should consider chastikey and emlalock for keeping subs in chastity long distance - you put your keys in a lockbox with no access to them until the time is up. Lots of fun!

Admin on May 25, 2020 22:54

Thanks for the suggestions. I know of those sites, but I typically prefer to lock guys in chastity myself. I have ways of doing this remotely while still keeping things super secure, and without relying on a third party website. ;-)

gogglestars on May 26, 2020 04:54

Let's see... have victim... er fun-loving submissive... film themselves locking the cage on, and put the keys in between to strips of tape. Then write a word of your choice across the tape. Ask for a picture of the tape and/or cage every once in a while for "proof"?

Admin on May 26, 2020 10:01

Good idea, and nice and simple too. I've done something similar, but with the keys in a plastic bag, then clear tape wrapped around the bag with something written on it. Works great!