Dram Jar Sessions

For whatever reason my Keyholder isn't allowing any activity with my penis - no games, no pain sessions, nothing. I haven't even seen my penis for days. I'm stuck in a loop - constantly thinking about my wee-wee. The unending urges are maddening.
 
Journal Entry - May 15th, 2025

It was decided that I should keep a journal - and I’m enthused about this. This solves a communication problem; I tend to not send repetitive updates to my Keyholder - such as being horny and frustrated. This is a given - especially now - being that I’ve been locked up for 42 days inside a cramped cage. Outside of hygiene openings and/or changing to a different chastity cage - my dick has been trapped in a cage 24/7 for 42 days. Not seeing your manhood for such a long time is a weird feeling.

I have two chastity devices (image below) - one is a full belt (Behind Barz) and the other is a “ball trap” cage (Viper). When I’m at home I’m locked in my Behind Barz chastity belt - and when I leave the house I use my smaller ball trap, Viper, cage.

So, getting back to my situation - and the state I’m in. I’ve been experiencing full deprivation for over a month - with 24 more arduous days to go. That is to say - I’m locked up all the time with zero interaction - no edging, no games, no painful sessions - nothing. Just time locked in a cage. This is my punishment. Effectively I’m in prison. Yes, at times I want to cry. Often I find myself yearning for pleasure. My Keyholder told me that when I get desperate I should think about why I am locked up.

I’ve had such difficulty all of my life with lust - masturbation - and looking at women as sex objects. This is why I’m in jail. I know this - but it’s still painful to be here - lack of touch - and the humiliation of being caged is overwhelming. There have been so many nights and days I’ wanted to send an email to my Keyholder begging for mercy - yet, I’m afraid to do so - and I haven’t. I have 24 more days to go - I want to be good - because I want a chance to masturbate and cum. Yes, I admit it, I want to cum - badly. I know it’s wrong - but, the urge is so deep in me.

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Journal Entry - May 20th, 2025

My Erotic Morning

It started with a dream at 5AM, then slowly waking up to the reality of being encased in a hard steel cup encasing my cock and balls. Not wanting to let go of that beautiful moment I reached down between my legs to caressed the lifeless metal entombing my throbbing cock. My cock was wet with excitement - with only a few millimeters of metal separating my cock from my busy fingers. I could feel the precum leaking. And to be honest, I love it when this happens. This is as intimate as I can get while aroused in jail. So close, but so desperately far.

Desiring to continue my beautiful, soft, erotic dream and not let anything get in the way - I decided to lay quietly, closing my eyes again - wishing for the dream to come back. I knew I had to get out of bed very soon and go to work. And work almost always takes my mind away from sexual thoughts. So, I stroked my full metal chastity belt hoping for any feeling that could be construed as orgasmic.

Next, I reached for my nipples and played with them. Stimulating my nipples made my cock respond by pushing harder against the unrelenting metal imprisoning my manhood. In that moment I could feel a spasm and imagined squirting hot, ropey, cum. It was as beautiful as could be. As realistic as possible given the situation. The truth is - I never came. I was a hot wet mess between my legs with my entire body craving an orgasm. At that moment my alarm clock sounded - alerting me that it’s time to get ready for work. The fun was over.

This is sex for me now.
 
Journal Entry - May 21th, 2025

I’m feeling distracted today. My eye continues to wander - then I think about my situation. The horniness comes in waves - today is one of the bigger ones. I’m so frustrated while serving time and won’t be out for at least another 17 days. Honestly, it would be better if I would be allowed to masturbate just to relieve the pressure. I’m sure there’s a way to ejaculate without pleasure or very minimal pleasure - then I won’t feel so worked up inside my chastity cage. Okay, I understand that whenever I get like this I’m supposed to think about what I did to put me in lockdown. I am so sorry for being selfish. Sometimes I feel my penis controls my life and there’s nothing I can do to stop it.
 
Journal Entry - May 22th, 2025

How did I get here?

I wake up every morning locked in one of the highest security chastity devices available on the market. At the time of this writing I’ve been stuck here for 49 days. I’m on a constant wild ride of drippy frustration as my emotions and hormones undulate with the passing days. For nearly two months my only sexual response is leaking precum beneath my belt. Other than that I feel no pleasure of any kind between my legs - no satisfaction, no erections, and no way to squirt hot cum - no matter how badly I want this.

I put myself here.

I didn’t want to admit that - but, all my actions placed me in this cock prison. First it was the 100 strokes game that I screwed up - then it was my low effort response after being allowed to orgasm on 3/31/2025.

Summary of Screwups

Incident 1 - 100 Strokes Failure

By the grace of my KeyHolder I was allowed a simple game referred to as “100 Strokes.” I was allowed to stroke myself 100 times to the beat of the metronome set to 60 beats per minute. This works out to hearing a click once per second. For every click I was allowed to stroke myself once. Instead of following the instructions I stroked myself too fast - eventually coming.

Incident 2 - Ghosting After Cuming

On 3/31/2025 I was allowed to cum as many times as I pleased over a 24 hour period. I was only able to masturbate once on 3/31/2025 due to my long working hours that month. How I wish I could have had that day off - to REALLY enjoy masturbating all day long. This itself wasn’t the problem. The egregious behavior I exhibited was ghosting my KeyHolder after I had cum and then using excuses as justification for my actions. She had asked me to tell her how many times I came that day and if I could make ice cubes from my cum. Truth be told: I didn’t want to make ice cumies because I thought that was gross. I felt I was too busy to communicate the details of my orgasm to my KeyHolder. Subsequently, I never told her how many times I came that day.

So, now I pay the price. I’ve lost access to my own genitals for a long period of time. But, at the same time my KeyHolder didn’t give up on me - even though she should have.

I strive to do better.

From this point forward, every time I feel like crying because I can’t touch my penis I need to read this journal entry to remind myself why this is happening. Next time I need to think about making my KeyHolder happy instead of thinking about my penis.
 
I kind of feel this is wrong to say. But, today I watched women’s wrestling. I really don’t know how I got here - but I found it so incredibly erotic - and continued watching throughout the day today. Seeing those women splayed out in their tight spandex got me so hot and bothered down there. As I continued watching I imagined myself penetrating - and fucking. I could feel my cock throbbing and leaking profusely under the hard metal shield imprisoning my cock. In that moment I imagined having a full, upright, erection - strong as can be, free, and pulsing. Even without cuming it would be a joy to feel a uninhibited erection.
 
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May 30th Quick Journal Update.

Last weekend was a three day weekend - Memorial Day. I was busy performing. I’ll be performing again this weekend. And of course, I’m working full time. I haven’t had time for my penis. But, isn’t this the way it should be? Aside, I plan to buy a spanking machine and tie that into my machinery. The basic idea is to use a vibrator on my dick. The catch is to hold off from cuming for one minute. If I can’t hold it I get spanked. Something like that. Thoughts?
 
Two days from now I will have my long awaited orgasm. I’ve been waiting for this. I’ve planned in advance by taking the day off from work so that I’ll be home. It will be a date with my penis. The first thing I’ll be doing is removing my chastity belt and cleaning up. This includes a full body shave so that I’m as smooth as possible. I may not orgasm immediately though. I would like to spend a few hours free from my cage and slowly work up to sex. I don’t want this event to be over in 30 seconds. I want it to last forever. Sexual pleasure, sexual waves, rippling from head to toe for hours. This is the sweet spot. Right?

I’ve already planned the explicit details of my orgasm, how it will occur, where I’ll cum, which room I’ll be in when I cum, physical aides, audio & visual aides, etc. I was going to include those details in my journal but at the last moment I decided to leave this out.

< sexual orgasm details omitted >

The most difficult part of a long, confined, chastity period is the first and last week.

The first two weeks of chastity are difficult because your post-orgasm happiness is immediately hampered by locking up. It’s the cold reality of having to cage your cock - surrendering sexual freedom by placing your manhood inside a metal enclosure designed to deny any and all pleasure. Knowing you cannot escape is the worst feeling. The next two weeks are the worst because you’re so incredibly horny while in prison. It’s because when you have that rare orgasm your body reacts by triggering hormones that feed the sex impulse - the deep craving for sex. And when your penis is caged during this heightened sexual state it becomes the most maddening feeling I could ever describe.

The middle part of chastity is different. The term is painfully long - and isolating. But at the same time, you’ve given up control - and there’s solace within the deterministic outcome of your new lifestyle. That is, in a way, always knowing that your life will be absent of sexual experiences serves to quell restless sexual energy. Impulses are relegated to the mind.

After some time has passed - maybe three weeks in - you transform by disassociating from your sexual thoughts. Psychologically, it becomes easier by keeping yourself busy. Yes, the physical horniness continues and there are countless trying moments nibbling at your sanity. But, it becomes manageable once you accept your fate. The only place you can’t hide is at night - when you’re dreaming. More than once I was awoken in the dead of night because of a raging boner trying to break loose from my chastity belt - interrupting an erotic dream about sex with a beautiful woman. Normally, I’d jack-off in an instant and go back to sleep - but not when caged. This is when frustration levels are the worst. In a way - even my dreams are regulated by wearing a chastity cage 24/7. Honestly - it really sucks.

Things begin to change when you’re a week or two away from release - especially for as long as I’ve been locked up (over 65 days). The anticipation swells up because you know you’ll be cuming relatively soon. And although this is a good thing - in a weird twist - frustration levels go up again. Throughout the day simple things such as visiting the grocery store can become unexpectedly erotic. Knowing I’ll have dick-in-hand soon triggers those hardwired neural nets in my brain - making the world around me vivid with sex.

The magical part of chastity isn’t the anguish, suffering, or continual dripping of precum. Although I do kind of like the latter. What makes chastity magical is the act of denying yourself for a higher purpose. Another human controlling your sexual outcome is a true gift and at times gets me through the night.
 
Today is the day! In three hours I will be touching myself. Well, actually, I’ll be taking a long shower followed by manscaping. After that I’ll put on my favorite underwear. Just the thought of feeling fabric over my cock has been dearly missed. No more metal cages. No more uncomfortable ball-trap cages. Just freedom. It’s so interesting how the simplest of actions have so much weight after a long period of deprivation. I just want to walk about the house in my underwear on only - cock unimpeded by anything. Au naturel. (except for my undies) I will be fondling myself throughout the day. I’ve been given permission to masturbate as much as I want for 48 hours. Isn't that wonderful? So, I might even wait and postpone my orgasm until tomorrow. Just being able to sleep 100% naked in bed turns me on. I’d like to go to bed with a strong erection, horny, drippy, and allowed to touch my long rod with soft, delicious, strokes. An immediate orgasm would kill the fun. I want these feelings to last forever. I love my penis! And I miss it so badly.
 
In one hour I’ll be removing my Behind Barz chastity belt.

I’m going to use a vibrator on myself. However, I do not plan to have an orgasm. I just want to take in the beautiful vibrations to the point of dripping precum profusely.

That got me thinking.

I should use a small, battery operated, vibrator and put that in my underwear so that I can feel the sweet vibrations even with my pants on. Oh what a joy that would be! Then I thought to myself - WHAT IF? What if a remote controlled vibrator could be used by somebody else? What if the remote control vibrator were BUILT INTO my chastity belt? Hmmm. The possibilities abound!

Now, this is sounding like a lot of fun! Doesn’t it?
 
I’ve recently developed a silly grin on my face that’s slightly permanent—like a souvenir from a weeklong carnival that overstayed its welcome. My wee-wee aches faintly, but I just can’t stop fiddling with it.

During the past 36 hours there wasn’t a moment untouched. Not a single second left blank. Every hour spilled into the next, brimming with neon sensations like music rattling my bones, my bone, my boner. I said yes to everything. I opened every door, even the ones clearly marked *Do Not Enter*. Possibility wasn’t just explored—it was devoured, licked clean, and chased with a grin and a wink.

Each indulgence felt justified. One more stroke. One more spurt. One more hour awake, Dancing with Myself. 🎵 Do you hear Billy Idol in the distance? 🎶 Time was elastic, soft, like taffy pulling apart in heat. hmmm…

And now, here I sit, at the edge of it all—silent dwelling, lights low, the buzz beginning to fade. My grin lingers, though. It knows. It’s been places. My reflection in the window looks a little wild, a little foolish, but unmistakably alive.

The world may have stopped spinning, but my head hasn’t quite caught on.
 
Whoops! I just caught myself! Earlier today I was thinking when I get home from work I could masturbate. Then, later in the day, while still at work I realized that I had already ‘re-locked.’ Well - sort of. I’m not caged right now. Yes, I’m not allowed to touch myself and I am serving a chastity sentence on Chaster.app - but, I’m not wearing my chastity belt or my Viper cage. During the last two days I masturbated multiple times - so I guess it just slipped my mind that I’m back in chastity again.
 
I’m feeling very horny this morning and I don’t want to go back in. I’m still uncaged while making minor adjustments to the Behind Barz belt. The cup area seems to be fine - it’s the belt around my hips that bugs a lot. Still though - the Behind Barz is far better for me than a ball trap device. Nothing beats a highly secure steel belt like this one. It’s too bad this belt is so huge and bulky. It’s heavy as well. I call it the crazy belt. But, I’ve got to be honest when I say I feel like crying at just the thought of getting locked up again. Yeah, it might sound erotic and fun at first - but all that changes when it’s your reality. It is a very real prison. The final word will be hers. If she wants me locked up then I lock up. Period.
 
I can’t help but admit I’m having a problem today. It’s just that I’m really horny. I can’t stop looking at things. I’m fidgety. I want to fuck this feeling out of my system. That would make me feel better right now. I’m frustrated on my first day. 😭
 
After some adjustments to my Behind Barz chastity belt - I relocked today. I was getting worried I'd do something I'd regret - so that's why I locked myself up. Punishment for bad behavior is extremely painful (Tabasco Sauce applied to my sensitive bits while tied to a gurney). I still remember that incredibly painful experience. My four limbs were stretched out and bound by leather straps. I was naked. My cock and balls fully exposed and doused with Tabasco sauce. This was one of the most helpless feelings ever. I just had to wait as the hot pepper chemicals dug their way into my soft penile flesh. The burning was very painful - making for an intense bondage session. Other than moaning and tugging on my restraints there was no place to hide, no thought or sexual image to save me from the pain. It was pure agony. I never want to re-live that again. So, I put my chastity belt on. No, I don't want to be locked up. I don't want to be sent to jail not knowning when I'll get out. However, the alternative (should I masturbate) is far, far, worse.

I'm safe now. Locked in a steel cage. I'm free to look at whatever excites me. I can't get an erection though - the metal cage points my dick down at all times. No fun for me. But, I am protected. I can drip. And I have been dripping all day today. My cock has been calling me - begging to be touched, stroked. caressed, teased, and played with. These are lovely thoughts. Memories of the past. At least I can experience sexual thoughts and drip as much as I want inside my lust prison.
 
I found myself calm this morning. I was going bonkers yesterday - obsessing over all things sexual. It got so bad I expedited the fitting process of my Behind Barz full metal belt and quickly locked myself in before anything bad would occur. The way I was behaving yesterday I was moments from an unauthorized action. Locking up saved me.

Although I had locked up around noon - the day wasn’t over just yet. Before I knew it I was grabbing and tugging the hard metal cup with both hands moaning in desperation. The horny monster was driving me utterly insane.

My fingers were blocked by the metal cup of my chastity belt. Just millimeters below the shield my hot throbbing cock was trapped and eagerly awaiting any attention - any stimulation. But I felt nothing - nothing but frustration as my cock continued dripping throughout the day - eventually staining my pants.

I was so desperate I began using a vibrator on my Behind Barz belt. It was never enough. My Behind Barz chastity belt is designed such that the penis tube sits beneath the metal cup. The metal cup is not directly connected to the penis tube. The result is that the penis tube floats inside the metal cup. Mechanically this decouples any vibrations from a vibrator placed directly on the cup or anywhere on the belt. As powerful as my Hitachi vibrator is - all the vibrations were deflected around my penis - leaving only the faintest of feeling - which just isn’t enough. There’s no ‘getting off’ while locked in my Behind Barz belt. This is an impressive design.

Well, hopefully today and coming days will not be like yesterday. I know it’s only because I immediately locked up after two days of non-stop cuming. Psychologically, I wasn’t prepared to get physically locked up again. I was dreading that. I continued to repeat that thought in my mind - I just didn’t want to be under lock and key again. It’s so humiliating.

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It’s been 24 hours locked inside my Behind Barz belt. I’m a lot better today although I did place my vibrator over my crotch area with my pants on - attempting to feel something. Yes, I feel the vibrations but they are so weak with my chastity belt on. I played with my nipples while the vibrations were going - that helps but, I couldn’t cum this way.

My Chaster.app lock states I’ve been locked for two days now and that is technically true - but I spent the first 24 hours without a cage. That was lovely - but dangerous. I’m caged now. I have the serialized metal seal. The metal seal is a good way to insure the belt hasn’t been removed. Although I don’t need to ‘check in’ and verify as is commonly done on Chaster.

My Keyholder would enjoy if I spent quality time in The Machine. There’s a possibility I’d get a reward if I make her happy with my videos. I’m focusing my pent-up sexual energy on this task now. What makes a good video?

There’s a lot that goes into one video. It isn’t as simple as pointing a camera and shooting. It takes a lot of effort to produce something of quality. But, the task at hand isn’t production - but the subject material.

Should I use electricity and give myself shocks using the motion sensor? Should I add dripping Icy Hot? Should I demonstrate the perfect ruined orgasm?

A ruined orgasm using electricity

The perfect ruined orgasm is cuming without moving. The perfect ruined orgasm occurs when you cum without your body or dick moving - and your cum doesn’t shoot. A ruined orgasm occurs when your cum pathetically oozes away from your body. This can be achieved under the right conditions using electricity. I have an old video demonstrating this.

Normally, when a dick ejaculates cum - the cum is shooting across the room or deep inside someone. That action is very satisfying for a man. However, if a man’s cum slowly dribbles away then the feeling is the opposite - very unsatisfying, frustrating, and possibly humiliating. Imagine being let out of your cage to experience a hands-free, ruined orgasm, using electricity, and then re-locking.

The quality of the ruined orgasm could be used for or against me. If I try to ejaculate - shoot my load then a swift punishment would follow - of course. And there's always that possibility that shooting cum is involuntary. But, if I just focus hard enough I can prevent unwanted twitching and shooting ejaculate. So, the game isn't easy for the man if he's instructed to ruin his orgasm. And the man cannot hide that fact - because either his cum shoots or it dribbles. The simplicity is elegant.

So, if I have the ‘perfect’ ruined orgasm - cum dribbles slowly out of me with no spurting and no movement (twitching) of my dick. If I achieve a true ruined orgasm then maybe a reward could follow. Perhaps the ‘reward’ would be nothing other than returning myself to my cage? Ejaculating, or spurting, and twitching of my cock while cuming should be rewarded with pain while in bondage.

Metrics to judge a ruined orgasm

  1. Amount the cock twitches as cum ooze out (ideally no movement)
  2. Amount the body reacts to the event (ideally zero movement)
  3. Amount of breathing during the even (ideally 100% ‘at rest’ breathing)

I think she might like this one.
 
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Shortly after waking this morning I felt my cock pushing surprisingly hard against my chastity belt. The feeling was harder than in previous days. I’m not sure why. It was as if my cock had become more powerful that morning while attempting to bust out of the confines trapping my sex.

I was still in bed on my side, so I rolled over such that my body lay flat. With the exception of my Behind Barz chastity belt I was naked. I began caressing my nibbles. I gasped as my dick pushed harder against the steel cage. I needed more - so I grabbed my Hitachi vibrator and gently placed it over my cage as I continued playing with my nipples. This continued for a good 15 minutes causing a small pool of precum to collect on my bedsheet. I was no where near an orgasm - but enjoyed the pleasurable feelings nonetheless.