Dram Jar Sessions

I haven't had an update on further punishments from my Keyholder. She did ask me for a a few ideas - I provided this and also reached out to the community seeking additional ideas. Some of these just aren't my cup of tea - at all. I'm definitely not being theatrical when I say some of these punishment methods gross me out. I guess a better way to say it is that some of these punishment ideas are way past my limit. But, to be transparent - here is what the community offered:

1. 100 lashes with a cane
2. Shock collar
3. Ball kicking.
4. Double my time I’ve served when the accident occurred and add that to my sentence
5. Pee control (penile emission training) - method a) or method b):
   a) limit number of times in a day your can pee in a toilet - otherwise hold it or pee in a bottle and drink it
   b) “Docking” - fold the penis so that peeing is not possible during no-emission periods.
6. Place an elastrator ring around your ball sack. Take the number of days you were short of hitting your target (release date) - use this value as the number of minutes the elastrator rings stay on.
7. 300 hard strokes with the cane - spaced over three days (100 per day)
8. Return the fluid (cum) orally

 

Short update

Punishment for my little accident last Friday will be:

• 15 minutes of Icy Hot to my cock while my body is restrained.

As is normal for this chastity lock - video documentation will be sent to my Keyholder.

I actually, don't like the pain from Icy Hot - although it isn't nearly as bad as capsaicin (which brings tears to my eyes). At least with Icy Hot the pain is somewhat temporary - eventually giving way to that cool feeling. The first time I tried it was in 2006 as requested by Rachel. Back then I didn't know this was a thing - a type of punishment. Oh, I was in for an abrupt surprise! It wasn't fun and games anymore. That was painful.

So, at the moment I have this trembling feeling - anxiety - knowing I will be punished in this way - but not knowing exactly when. But, I know how it'll go. I'll get an email or an update to my lock. Before opening I'll already know that it is time to start the punishment. From that point forward it will be formality - to read the instructions, sign out of my lock, prepare the restraining equipment, setup up of the video recording equipment - and finally - submit to pain.

But, the upshot is that It'll be over soon - once the pain subsides and I can go on guilt free (mostly anyway). I can't take back the cum I ejected - even though it wasn't a 'full load.'

I'm sure others feel the same - but when you invest beyond two weeks of pure chastity - you don't want to spill anything - not even a drop.

All for now

 

I'm not looking forward to punishment - Icy Hot on my cock and balls. I find it rather painful - like my bits are on fire painful. I found myself probing my Keyholder to get out of this punishment. I was extremely subtle though - so, she doesn't know I want out. But, I really do want out. It is very unpleasant.

 

12 Hours Added

I'm reasonably sure I got the added 12 hours tacked on because of an improper hygiene cleaning. Recently, my time to clean has been restricted to 9 minutes. My normally scheduled cleanings are every 3 days. Well, yesterday, during my scheduled hygiene cleaning, I pointed the removable shower head toward my erect cock and held it there for about one minute. Yes, it felt good. But, it wasn't for long - since I only had 9 minutes to do everything - take the old lock off, clean, shave, wash the cage, put the cage back on and finally sign into the Chaster app. I did this in 8 minutes - leaving me one minute to spare. However, since my hygiene cage openings are documented with a security video my Keyholder can see everything I do. She caught me and added a half day to my sentence.

I've got to be honest though. I want to do this again - but for longer. If I go past the 9 minute allotted time for hygiene cleaning then the Chaster app will automatically ad 12 hours. So, that kind of means - technically anyway - if I full on edge for 30 minutes - that'll only cost me 12 hours of time in a cage.

For now my release date is October 2, 2023 at 10:18 PM

 

12 Hours Added - Update

Actually, the 12 hours I got is part of the game (not for a wrong doing on my part) - if someone joins the Chaster lock after me and serves one day - then I get half that time - 12 hours. That's all it was.

Aside - I'm kind of breaking down right now. I've never been locked for so long. The cage is uncomfortable - especially at night. I wake up a lot during the night - then I get horny in bed with no way to stroke myself. I'm kind of at a point of begging.

Maybe it's time to exit out of this lock once my time is served. I've definitely pushed myself - a record for wearing a cage this long - for sure.

 

There are scads of keyholders on FetLife offering 'services' and many of these women are on OnlyFans. I'm not against the idea of a transactional relationship - but, geez - OnlyFans is a spam machine.

 

Problem is - you don't really know who you're talking to for all that money. It's easier to meet people the normal way.

 

I haven't paid any amount of money for key holding.

 

Now I'm feeling sorry for myself. I was horny through the night. Erections beneath a cage makes me want to hump my pillows. It's so lonely in this prison. =(

 

My Keyholder hasn't mentioned anything about my Icy Hot torture session - fingers crossed that'll be forgotten. I'm sure I'm dreaming about that though. Believe it or not - after all that has occurred - I kind of asked for another edging session. I'm referring to my accident the last time I was allowed to edge. I know, I shouldn't have asked. It's just hard to keep my thoughts straight when I don't sleep well - caged and perpetually horny.

I'm still learning her social cues - a little hard through text - not impossible though. But, during my caged time with her I've picked up on little things here and there. I'm doing my best to read her - so she doesn't need to explicitly say something to me. Ideally, I'd just know what she wanted without the dialogue.

On that topic - I just don't know if she wants me to sit through 15 minutes of Icy Hot pain or if she picked that punishment over adding more time to my lock. She expressed that she'd rather not have a huge amount of time on my clock/timer. I don't want a massive amount of time either. I haven't done this before - and, I think you're supposed to start out in smaller steps. I kind of took a big ass step - for me anyway.

But, it all boils down to what I want. I'm trying not to be selfish - but this is physical - like going through withdrawals. I have an Inner Urge that's eating me up day and night.

 

12 hours were added to my chastity confinement today. So, currently, I'm free on October 3rd, 2023 at 10:18 AM

 

Quick update

So, my Keyholder held me accountable - and made me follow through with the Icy Hot punishment for my little 'accident' I had while edging myself on September 22, 2023. That wasn't the only punishment - because after my accident my hygiene time was restricted to 9 minutes (from 15 minutes) every three days. It feels like prison. Anyway, the painful ordeal is over with - and I submitted my security videos to her. So, we should be all squared up and good now. Oh, yeah, I've mentioned this before - but I was really hoping we'd just forget about this little punishment thing. Icy Hot on you dick and balls isn't pleasant. My release date is still October 3rd, 2023 at 10:18 AM. That's about a day and half.

 

Otherwise known as funishment.

 

My Keyholder added 4 days to my chastity confinement. The added time was because I kept my Keyholder waiting 8 days to initiate punishment for my accident on Sep. 22. For each day she waited I paid with half a day. My new release date is now October 7, 2023 at 10:18 AM

 

My Keyholder added another 4 days on top of the previously added 4 days. My release date is pushed out to October 11, 2023 at 10:18 AM

I'll explain more tomorrow.

 

Another 12 hours were added today - I didn't get myself back into my cage quick enough during my regularly scheduled hygiene opening. I've got to say - this cage life is getting to me. It might seem erotic at first - to be locked up. But, I'm going bonkers. I feel that I'm at a breaking point now. Don't know how long I can stand it.

 

Oh, that - it was nothing. Negotiation not going my way.

 

Chastity update.

Okay, so, on October 4th, I was allowed 30 minutes of cage free time. I wanted to wear my favorite underwear without a cage. It was lovely. But, I was docked for fondling myself too much during that period. I wasn’t edging though - not even close to edging. But, according to my Keyholder it didn’t look that way from the security video. So, I got punished. My hygiene opening is every 3 days for 6 minutes. When I saw the change this morning I began trembling inside - while at the same time getting aroused and feeling my cage grip me tighter. I started begging with her too - even though I know that’s the wrong thing to do. I couldn’t help it - I was really caught off guard. I thought I was in the green here - as in everything was okay with my cage free time. But, I think I wasn’t supposed to lay a finger on my cock. So, next time if I’m awarded cage free time I’ll be a lot more careful about this. At this point I seriously doubt I’ll be allowed to edge again - at least until my confinement time is up.

 

Oh, yeah, I forgot to say this. When my Keyholder emailed me she wrote, "Anything you would like to tell me?" Suddenly, I felt as if I had been called to the principal's office, asked to take a seat, and then given the opportunity to confess my crimes.

By this point - when she sent me the text message - I had already seen that my hygiene opening was set to the shortest period ever - 6 minutes. And, it was then, I knew something was not right - and that I was in trouble for something - likely involving my penis.

So, I place the blame on my penis. It wasn't me. My penis made me do it.