29f help me torment my ex in chastity

[f_keyhoder]

Hello getdare people,

I have my ex boyfriend in chastity for a few weeks now. He doesn't know I am on here. He definitly is a member of this forum. I will not tell who it is, because I am now telling you:
I do not intent to release him except for medical reasons or he finds another girl that actually wants his cock!

Though I want him to believe that by doing tasks for me, he can earn his freedom.

We do not live together. He is now almost an hour away by car as well. So I need tasks he can do on his own and prove them to me. I mainly want to see him squirm and hope for release that will never come by my hands.

Now and again I see him in person, but very seldom in private.

What is he willing to do for me? Well let's take a look at his list:
anal, yes he can be fisted
urine, he doesn't like to drink it, and I would want to keep it as a punishment only, but he can get his clothes soiled or interact with it in any other way
bondage, sure, let's tie him up some more
bladder control, hmm that sounds interesting, we never tried that when we were together
hypnosis, well we talked about it, but also never gave it a shot

now that was from his list, there is one thing he hasn't on his list, that is whoring him out to other guys. I want to try that, get him fucked regularly.

I will not reveal who he is, but feel free to ask questions and give tasks I can make him do.

I want him to do at least 3 to 4 tasks per week. They should keep him horny though, that's the idea with me having all the keys.

Any ideas on how to accomplish this are extremely welcome!
I will report back here on how he did and wether he was good or not. By the way, he thinks there is a release date, so I can arbitrarily threaten to add or remove day or even weeks.

Also, feel free to ask questions needed to help me with my chastity slut.

[Slave_Zuzanna]

You do realise he can cut the lock any time he decides he is not turned on by the whole situation? This spoils the whole "aura" I guess...

[f_keyhoder]

I know, but since he was the one giving me the keys the day we broke up.. haha.. he wants this to happen. I already send him nudes of me now and again, but that is mainly it.
I don't want to invest too much time into him, but I still want him to be entertained. That's why I am asking here. There may be a ruined orgasm now and again, but it is not planned yet. He wanted this and reminds me to be merciless, so yeah, I want to be.

[CandyCox]

What a lucky boy. I wonder if he knows how lucky he is. Let's make him prove it. Every week have him make you a tribute. It can be anything really, a necklace, a poem, a video of him being humiliated. The key is to not tell him what to make, just tell him to make something you'll like. Also, he has to make it, no buying gifts.

Not sure if you want him to be a sissy or not, but one fun way to get him ready to be a whore is through hypnosis videos. Almost all of these have some sissy messages or aspects, so up to you if you want to use this idea. Have him watch an hour of hypno every day or other day. For the first 10 minutes have him give a realistic dildo a blowjob. The next 10 minutes have him fuck his ass with a similar dildo. For the last 20 minutes have him do both.

If you don't know where to start for hypno videos I'd check out Deep Slut Puppy and Emperor Hypnos. The site Anna Malice does a great job finding new videos as well.

[andyinny]

If you could arrange semi regular private meetings....force him to dress en femme. Inspect. Criticize everything that makes him not pass for a girl. every time you can pick out that he is male add another meeting where you dont give him a ruined orgasm.

[f_keyhoder]

I actuallly do not want him to become female. haha, you guys yre funny. but there are some interesting suggestions already.

[f_keyhoder]

hmm.. nothing yet? man this is harder than I thought. haha, I thought you people would be all over his ass. haha.

Well for now I make him take a video of him fisting his ass for me once a week. That should keep him stretched and entertained.

I also told him that only completing a task will get his cage open on my scheduled release day. Which of course up until now isn't even set, if ever. I want to get him excited to think he gets a release around christmas though. Which of course, when the day comes I will deny him.

So, please let me know some suggestions. My dear people of this awesome place!

[paulil71]

tell him you want a regular photo of him (naked, only his cock cage) and a girl naked.

[Nwbie]

Make him go commando certain days of the week but to add to the humilation make him wear a (pink) ribbon around his cock.

Now here's the thing you really want to keep him as horny as possible because the hornier he is the more willing he will be to accept your ideas.

Now to achieve this you should tell him he's to watch certain videos everyday and since you guys wanted to try out hypnosis look for some files that can be played on loop and are non-intrusive. There are some generic files that should make people constantly aroused if looped. This can be put on as background music underneath regular music, just make him listen to these for several hours a day.
http://www.warpmymind.com/ is the place to go to to find free files if he uses a playlist when he's working he can edit them underneath his playlist.

Also other tasks that might help him and you
Is that you make him find you the best porn he can.
If you want to humiliate him you can say something.
"I want you to find me proper porn, the more I like it the sooner your release might come. The only reason I need this porn is because you were never sufficient and not able to statisfy my needs being the pathetic loser you are".
Some guys like that kind of stuff, I myself wouldn't but I can't judge for him so up for you to judge.

Now you said you wanted him to start doing stuff with guys.
Well since he's already into anal this should be a bit easier.
I think there are two approaches one is where you set up a party and basically prep it in such a way that he's going to be fucked some guys. Of course you'll have to invite some guys that you know would want to fuck him in the ass and it might be easier if you let them in on the plan.
One of the things you can actually do is tell him that you want to fuck him with a strap-on. when you guys meet you tie him up and start by fucking him in the ass however half way through you swap with a guy that was in on the plan all along. Of course you can also get him tied up in a party were you guys play TorD, strip poker, etc with some additional rules. It's quite easy to rig the game against a single individual in most instances especially if they don't expect it.
On top of that if the guys want to fuck him you can even have them own you a favour.


Or the other option is that you play a game with him where he can earn points or letters. By example you pick a word and once he guesses it he will be one step closer to release or get release.
Now the point here is that you give him letters (or points) every time he gives a guy a blowjob or gets fucked in the ass, the more extreme the bigger the reward. (the better the proof the better the reward, also if you don't like the proof don't reward him)

What he however is not going to know is that you pick an extremely long and hard word, especially if you know a different language you can use a word from that language (all in all you never said which language it was) also I recommend using a dictionary or google to help you look for good words.


Now good luck with everything and have him keep a diary or have him write some reports of which I would love to receive a copy.
Tell him you want to for educational purposes or as erotic reading material, etc.

[cbtslave999]

Set a date for release (or so he may think) by using cards.

When you are together, take a deck of cards and explain the game to him before you start so you can watch his face as he gets more and more time added on.

Example game

Draw 5 cards slowly one at a time mocking him and laughing in between cards.

The number on each card will determine the days locked up.
(maybe even throw the jokers in for a crazy amount of time)

Then, any time he doesn't preform to your liking, or you just feel like tormenting him more draw another card for him to add on. Or even be nice and draw cards to remove time if he is good.
(these cards you draw when he is not around, so you could lie to torment him more)

This game could keep him denied indefinitely if played right, but still leave him with a glimmer of hope for reductions.

Have fun

[Oyaji Uke]

I love new users posting things like this that just sound so unreal and no picture proof. Everything ambiguous....

I hope your real and circumstances are real and you have fun.

[f_keyhoder]

These are some great ideas! Thank you! Still alot of work for me, but once setup things might get interesting.

to Nwbie: I don't want to humiliate him. Because he was a good lover. Finding guys who want to fuck him is a great idea. Though I don't know any. I'll keep that in mind though. I can always ask around with my friends, some of them are gay.
I do like the thing with earning points or letters to a word for interacting with guys. I will think of something like that.

to cbtslave999: that is an awesome idea! so I can finally set a release date and torment him with it. Thank you!

to Oyaji Uke: if you want any pictures, let me know. I don't know how to put them in here, but sure. If you want me to have him hold up a sign as proof. I will just tell him that. But please make it something not letting on, that I will send these pictures to other people. I will of course not show his face. But his selfies will get sent to those who wish. Though I should think of something to explain this away, if you have any ideas, let me know! He has to prove anything he does for me anyways. You can ask for proof. Just tell me how to get it to you.
Thinking about it, I would rather not have his proof pictures on this forum, since he is a member (as I said in the beginning), but sending them will be ok.

What else can I make him do? So far I have a method I might use to let him go look for men to fuck him. And a way to set a (never happening) release date. Oh, and a webpage to look for hypnosis. That will be interesting.

Thank you again!!! Any more suggestions are very welcome!

[Nwbie]

Originally Posted by f_keyhoder

These are some great ideas! Thank you! Still alot of work for me, but once setup things might get interesting.

to Nwbie: I don't want to humiliate him. Because he was a good lover. Finding guys who want to fuck him is a great idea. Though I don't know any. I'll keep that in mind though. I can always ask around with my friends, some of them are gay.
I do like the thing with earning points or letters to a word for interacting with guys. I will think of something like that.

What else can I make him do? So far I have a method I might use to let him go look for men to fuck him. And a way to set a (never happening) release date. Oh, and a webpage to look for hypnosis. That will be interesting.

Thank you again!!! Any more suggestions are very welcome!

Well yeah that's why I said that would be something you had to judge ;P
I completely understand that since I wouldn't want that myself either but look around the forums and you'll see there's a bunch of people who actually like it :P

I'm glad to be able to help you and your ex.

I was also actually thinking along the lines of some gay friends
I know it's actually not that uncommon for girls to have a few gays friends and especially those could owe you a small favor you know if you ever need help with something simple ;P

You would make me really happy with reports, I would love his reports much more than pictures of him.

[f_keyhoder]

right, I forgot about the reports you said. the thing is that they won't be in english. I can imagine this very good to make him write a report along side the pictures or videos he has to do. But as I said, they won't be in english. Although, I might get him to agree to do them in english if "we" want to set up a blog or something, for others to learn about the pros of chastity. Hmm.. I will think about that. But then again, putting a link of this in here could reveal me. If I make him do that I will let you know. I most probably will.
And then you can just ask me personally in a message for the blog. That might work acutally.