Extreme Chastity and Humiliation

Hello, my Sexy Perverts! As you may know, our site of the month is Chastity Hell. Not surprisingly, I’ve been thinking a lot about extreme chastity and specifically how humiliation and torment can be a part of it. There are a lot of things that can give your chastity routine a nice level-up to extreme chastity. Much longer lock-up times and regular tease and denial sessions are two of them. But, my own brand of humiliation and anguish can increase the intensity of your chastity to a much higher level.

When I guide you through chastity, I will of course own your cock and I will own your orgasms. That is a given.  Now, to make it even better, I’ve put my devious, kinky mind to good use to come up with some fun (for me, anyway) ways to add humiliation and torment to your chastity. I’ll take you to the level of extreme chastity and beyond!

Extreme Chastity and Strict Rules

Naturally, we’ll have a rule that you never get to put your sad, denied cock inside of me. Ever. But, I am sure that you will come up with plenty of sexy and creative alternative ways to keep me satisfied. If you’ve done a good job and given me all of the orgasms I want, every once in a while I just may allow you a few glorious minutes inside of my sweet, wet pussy. But don’t get too excited! Did you really think I would actually allow that worthless excuse of a penis inside me? Don’t be ridiculous. You won’t even need to be unlocked for this. Instead, I’ll hand you a strap-on dildo or a penis extension sleeve and tell you to put it on and get to work. You will give me as much pleasure as I can handle but you will feel none of it.

Extreme Chastity Leads to Extreme Frustration

Another way I could make chastity even more extreme is to frustrate you as much as possible. After being in strict 24/7 chastity, once a month or so we’ll have a session where I will allow you to try to have an orgasm – but I will make it very difficult for you. First, I will direct you to strip completely naked while I stay dressed in my sexiest outfit. And then I will unlock your chastity cage.

After you’ve gotten nice and hard (which I’m sure will take you about two seconds or less), I will roll two condoms onto your eager cock so you won’t be able to feel as much as you normally would. If I’m feeling particularly evil, I might add a bit of numbing cream under the condoms. Then I’ll restrain your hands behind your back and have you get on your knees in front of me where I will be holding a fleshlight in front of your impatient, dripping cock.

You’ll already know the rules. First, you will not start thrusting until I give my permission. Second, you will only penetrate the fleshlight as far as I specify. Will you get to slide in all the way up to your aching balls? Or only halfway in? Maybe I’ll be extra cruel and allow just the tip inside. Penetrating deeper than I allow will result in an immediate end to the session, so pay attention! This might sound difficult, but don’t worry – I’ll be sure to draw a little line around your shaft to serve as a guide.

Don’t Waste Any Time

Third, you will not have very long to attempt to cum. Only about a minute. Maybe a bit more or a bit less depending on what I decide. Both the depth and length of time I allow you for penetration depends on your chastity compliance, your attitude during the month, and probably just my whims and amusement as well.

Then, I’ll guide your needy, hard cock into the fleshlight that I’m holding for you. Be careful, though! If you manage to slip out, I won’t help you get back in and you’ll waste a lot of your precious fake pussy time desperately trying to get back inside without the use of your hands. Finally, I’ll start a timer and give my permission for you to begin. You will have until the timer goes off to thrust into the fleshlight while I enjoy witnessing your sheer desperation. When you are out of time, you will immediately stop.

All in all, I think your chances of cumming this way are pretty low. At the end of the session, you will of course immediately go back into chastity.

To be continued in part two…

What Did You Think?

So, my sexy perverts – What do you think about my extreme chastity ideas so far?  Does all of this sound as fun to you as it does to me? Let me know what you think in the comments below!

Before you go – do you want to read a different story – one about the domination and feminization of a sissy slave?  You do?  Great!  Head over to  A Sissy Slave Boss and read from the beginning.