I put Slave J into chastity for two weeks where I hit him with several tasks whilst taking over his computer and slowly locking it down. Removing all of his control whilst keeping him locked tightly into his chastity belt. One of the tasks I made him do was to purchase some sexy lingerie in his size as I had a final trial for him when I released him from his chastity. He would have to wear the panties for a full 24 hours without blowing his load into them. After two weeks of chastity this was a real challenge. 

So here is his diary written in his own words for your entertainment.

Chastity Diary

Sunday 2nd October Day 1

Today was the day that Mistress Jo instructed me to go into chastity. My custom belt has been gathering dust for a while, and although I have worn it in the past, there is always a nervous expectation of being locked up again. I duly took the necessary steps to shave and prepare. The gleaming appliance waiting as I exited the shower. Desperately trying to tear my thoughts away from Mistress, and avoid an unwarranted erection, I applied some lube into the penis tube, and myself. I almost began apologising to my unsuspecting cock, knowing that shortly it would be placed in its dark prison, curved down and around between my legs – and unable to perform in anyway. Those blissful orgasmic eruptions denied. Somehow I managed to become flaccid enough, and wasting no time stepped into the belt – as one would do with underwear. Pulling the cold steel up around me, I introduced my semi erect member to his new home, and with assistance from the lubrication, it slid down and around the curve. Quickly I brought the waist band over the hasp, and with a bit of wriggling applied the lock, and new numbered tag. Whew! Secured. Nice and tight. I hope Mistress will approve …

Monday 3rd October Day 2

I got a very rude awakening this morning, when my hand met with hard unyielding steel. Usually I like to touch myself and I am always hard in the mornings. But not today. Memories of Mistress Jo came flooding in, and suddenly I was wide awake, and squirming. Unable to become erect, the pressure mounted in my metal prison, and I had no choice but to get up, make some coffee and try to calm down. A shower helped, and I was able to examine the belt in the mirror. This thing is quite tight, and although I can wash adequately in and around the waistbands, there is little give at all. It’s very rigid and holds me so tightly in its embrace. I desperately tried to avoid thinking of Mistress and any sexual thoughts, but it was impossible, and again the cock struggled and things became very uncomfortable indeed. I’m going to have to be careful when travelling in my car, since I have to sit to pee now. No more dashing behind a tree! Even my male bulge in front seems to have disappeared.

Tuesday 4th October Day 3

It’s as if someone has flicked a switch. It’s only the beginning of day 3, and I am overcome with frantic urges suddenly. Day one was the novelty of being wrapped in steel after so long. Day 2 was the realisation that I have lost the ability to see and touch my cock, and it is no longer able to function. But now, now I do want to see it. I want to hold it, and play with it! Mistress has been teasing me, and there have been visions in my mind of what panties she wears, and how she might be enjoying my slide into sexual desperation. It hasn’t helped. It’s just made it worse, and I have started producing little trickles of drool in my underwear, something that Mistress frowns upon, and has said she will punish. But I can’t stop it. I can’t stop thinking of her, as her grip tightens, and the days pass. I’m trying to be brave, but I am spiralling into helpless submission, where being obedient to her every wish is the only way to get in her good graces to allow me out.

Wednesday 5th October Day 4

Oh my goodness, my confinement in chastity is really starting to bite now. I’ve become used to the feelings of being held in steel, and even become used to remembering to sit down to pee, along with planning my toilet breaks if I have to drive somewhere. I am reminded of my submission to Mistress Jo all the time. This belt never lets up. It is always there, teasing me about how ineffectual I have become sexually. My poor cock in prison, clamouring for some attention, yet unable to perform at all. It’s crying little tears of drool in my underwear – something that Mistress has been quick to exploit and levy fines for. I have to report any such unauthorised emissions, but I just can’t stop it. Mistress has been teasing me mercilessly about this, and on each occasion the penalties mount. She is diabolical in the way She torments. Never letting up on how much She is enjoying my desperate predicament. I am trying to be brave, but she has placed me in a no-win situation. The desperation continues to mount, and so do my penalties and fines. I can’t stop any of them!

Thursday 6th October Day 5

I still haven’t got used to the idea that I can’t play with my cock in the mornings. That half- awake state in the mornings, and that gentle pressure that turns into a very strong pressure as my hands travel beneath the duvet to once again be met by hard steel. It’s so close, and I want to hold it and play with it so badly. But I can’t. Coffee and showers and trying to force myself to think of vanilla things, is the only way to get matters to subside. It gets very uncomfortable otherwise and I am so aware of whether I even walk slightly differently. Mistress Jo wants me to spend some time in a lingerie shop buying a pair of silky panties. I’m quite nervous about this, as I know how arousing it will be seeing all those sexy items. But I must do it, as She will levy a daily fine if I don’t. Yes I must do that, before my fines start mounting too much. **Edit: I wound up doing some work on a computer, and had a student and my time ran out, so I wasn’t able to panty shop today. I’ll have to try again tomorrow. In the meantime I know Mistress Jo will give me a fine for failing…

Friday 7th October Day 6

Almost a whole week locked in this horrible chastity belt. Needless to say I am trying to be a good compliant boy for Mistress Jo. Today I had to go and buy some panties – not something I would usually do, but there is some pressure to do this now, of face financial penalties each day that I delay. I finally plucked up the courage, and a pretty salesgirl assisted me. I went several shades of red, as this is not my usual thing, and I am not a sissy - but finally came away with a pair of black boyshorts with lace. I hope this will satisfy Mistress for a while. Needless to say, I was at times quite hard, and the whole experience was somewhat humiliating, and arousing at the same time. Mainly because I had no choice in the matter. I am keeping a close eye on my debts to Mistress Jo, and already have started going into the red, so I need to watch that ..

Saturday 8th October Day 7

It’s Saturday, and I am off out of town on a little road trip. I need to quickly complete my tasks for Mistress Jo, and these are things I am getting used to doing now – this diary entry and my proof photo. My chastity continues unabated, and I am caught up in a swirl of constantly feeling aroused each time I think of Mistress. The belt never lets me forget this, and it holds me all day long – a firm reminder of what I can’t do anymore. Not much in the way of Teamviewer access from Mistress, but I see She has been busy with others on TV instead. I wonder if She is becoming bored with me, that She spends times with the online TV sluts, but we only have a rare few minutes together. It will be nice heading out into the country to try and clear my head, without straining and wriggling in desperation all the time.

Sunday 9th October Day 8

Mistress Jo and I have had a little chat and I am very relieved to hear that She does enjoy my submission. I am not one of those rude online sluts, and She has indicated that it refreshing to see. We are all good again and I am very grateful. Of course I am still locked in chastity, and leaking desperate pre-cum has become a daily occurrence, especially when I think of Mistress. Her power is increasing daily, and She installed something on my computer to regulate my online activity. I have had to beg and provide reasons why I should be allowed online at all, and what hours I need to be for work. Fortunately She has graciously kept this open for me, but I’ll need to be on my best behaviour. In some ways it’s so exciting to think of Her power increasing. I’ve lost control of so much already. The ability to orgasm at will. Administrator rights where I need Mistress to authorise anything. My poor denied cock struggles in chastity, but it’s no use. It just can’t get proudly erect or produce anything except tears of frustration. Can’t wait until the 14 days are up and I can get free to hold it again!

Monday 10th October Day 9

I am getting so desperate ! My whole little world is shrinking under Mistress Jo, and it has really made me realise just how much I am at her mercy. From not having anymore Administrator rights on my computer and being unable to install or uninstall anything, I now face the prospect of being unable to reach websites, or have a curfew on when I can even get on the internet. Cock is desperately dribbling frustrated tears and cannot even get erect, and I can only sit by helpless watch Mistress Levy additional fees on a spreadsheet I cannot edit. It’s diabolical ! Thrilling but daunting was that Mistress actually took money in front of my eyes on Amazon, and I could only watch helplessly, keyboard and mouse locked as she paid herself. This was, I admit highly arousing, but I couldn’t stop her, and I am a puddle of drool again now.

Tuesday 11th October Day 10

It was lovely to connect with Mistress today on Teamviewer, and she has graciously allowed me back on Fetlife – my favourite site that K9 blocked as pornography. Of course this has levied an administration fee, and added to my online debt. I am so nervous about this. I thought I was ahead in my payments, but that lead has been whittled down to the point that I am going to have to pay in again. She has a way with extracting money and more, and I am constantly struggling trying to please her, but the debt keeps mounting, along with my sexual desperation. I can’t do anything about it either or face her wrath. She has even suggested that she has the ability to completely lock me out of my computer, and that would be terrifying. I really have no choice but to comply with Her wishes. I foolishly tried to see if I could stop K9 as a process, but not being an Administrator, I simply can’t. There is just no way past this …

Wednesday 12th October Day 11

It’s wonderful that Mistress Jo and I seem to be in a routine of connecting in the mornings. Her time zone is 12hrs exactly behind me, but it seems to be working out. I really look forward to seeing Her each day, and it is my highlight. Today She has removed more privileges from my computer and I now can no longer access the Task Manager or even the Control Panel. It’s made me realise how capable She is, and that She means business and enjoys the control. I am quite at Her mercy it seems, and I am powerless to do anything about it. She seems to enjoy knowing I am struggling in chastity, and today, in my desperation pleaded with Her to let me touch myself. Not the greatest thing to do, as she immediately fined me 5 pounds for asking and added it to the sheet, which I can only look at. I am anxious about my money being steadily milked, as exciting as it is for both of us, but I know at some point I probably won’t be able to pay, and then what ? I’m trying really hard to get more students to generate more money to be able to keep up with her demands, and I am also trying to smoke less, so that I can save a bit on buying cigarettes. Needless to say I am aching in this belt now, and I drool pre-cum almost constantly when I think of Mistress. A huge smile on Her face, as she squeezes tighter and tighter, knowing I cannot stop her. She is just too strong, and has so much power over me, I am putty….

Thursday 13th October Day 12

Mistress and I only connected briefly this morning, and she very graciously let me install some scenery packs for my sim. I have lost the ability to do that on my own now, and so any thing like this needs her permission. More and more Mistress refers to this as ‘Her’ computer, and how she is allowing me to use it – and it has sunk in just how quickly she could take it away from me. I am not too busy with students today and tomorrow, and in some ways I am holding my breath wondering if Mistress will crack down on my internet access over the weekend. But I am thrilled to be approaching my chastity target, and should be free of chastity over the weekend. Ohhh it’s going to feel so wonderful ! But I have a suspicion being free will cause some pain to my wallet …

Friday 14th October Day 13

I am so desperate in chastity now after 13 days, and willing to do just about anything to get out. Mistress and I didn’t chat much this morning, as I think She has been busy and experiencing some computer issues. Of course I still wrestle with this chastity belt, and it is very challenging not being able to touch myself. She seems to enjoy my suffering and control my orgasms, which is in my job description to provide her with this enjoyment. I am of course constantly drooling pre-cum now, and can’t seem to stop myself. But just little pathetic oozes and dribbles. My goodness, how things have reduced from joyous blasting eruptions ! But only one more day to go – if Mistress Jo will actually let me get out. I have to wear my panties for a whole day without coming, and I know this will be a huge challenge, as finally I will have access to my cock again, but can’t do anything with it.

Saturday 15th October Day 14

It’s finally arrived. My last day in chastity. I will struggle through today somehow, straining and dribbling as I usually do, and unable to stop thinking of my dear Mistress Jo. In a lot of ways I am so aroused, not just with the chastity belt, but also that she has such a tight grip on my computer. I have done a few ‘experiments’ to see if there is any chink, but there isn’t. Her control is so tight I am simply faced with warnings that I need administrator approval for everything. I can’t access the settings or control panel either along with the task manager, and this means I can’t even change my desktop background. Fortunately I am still allowed to access the internet. I actually put the panties on today for my proof photo. I’ve tried to avoid this because I do find panties so sexy to touch and see, and I worried that it would drive me mad in my denied state. But I did it anyway so Mistress could see what they looked like. I was also curious as to how they would look over my shiny belt. Hard, shiny steel, covered in soft black lace. She seemed to enjoy the photos. So tonight is my last in chastity, and tomorrow I can be freeeeeee!

Sunday 16th October Day 15

Today is my big day of freedom from this horrible chastity belt, that has held me tight for two weeks. It’s been unforgiving, and caused me to adjust my life in so many ways. But finally cutting the seal, and easing it off was quite a cathartic experience. I have a cock again ! Rushing into the shower, I had a long delicious, hot shower. The hot soapy water all over me, and being able to hold myself again, and, well, touch, naturally caused an erection – something I have been told to avoid for the next 24 hours. Oh it was bliss ! I shaved, I washed, and as if in a daze found my cock again, that had been out of sight, action and unable to erect for so long. I could have cried ! But feeling guilty, as if secretly touching myself, I quickly got out of the shower, dried, and then slipped the panties that Mistress had made me buy, up my legs and around myself. It looked so smooth, and so feminine on me – and I am not a sissy, but it all honestly, panties are made from such luxurious fabrics, that as men we are often envious of such luxuries. They were snug, and sexy – and without dwelling on them too much, lest I get another fine-able erection, I took a quick photo for Mistress, and got dressed completely, try to ignore them, and my freedom as much as I could…. I have to get through 24 hours like this, and report any erections.

Monday 17th October Day 16

I somehow managed to get through yesterday wear silky lacy panties the whole day. It wasn’t that I didn’t feel sexual after two weeks of orgasm denial, but that it was just a busy, social Sunday yesterday. Friends for lunch. A trip to the Mall. That sort of thing. I did think of Mistress though, and did get erect. A total of 4 times, for which I shall be fined. I couldn’t help it. My computer is tightly under Her control, and I find that hugely erotic. So it was thinking of these aspects that made me hard. But this morning was the most difficult waking up, with an urgent erection, and cock screaming fro attention. I couldn’t help it, and did loving hold it and play with it for a while, but as the cum started boiling, I tore myself away, and … made some coffee. An accident at this point would cost 50 pounds – and since I owe Mistress quite a bit, it was a major deterant. Online we spoke and Mistress seemed proud that I had managed to contain myself… but then it was onto Amazon with Teamviewer for a hard financial drain, and I lost control completely. Cock throbbing and dribbling urgently, as she expertly flicked into the payment page, adding in the money I owed, including the fines I had accrued. I pleaded and begged for relief, and Mistress was gracious to offer me relief. The timing was perfect – and as she hit ‘Send’ on the transaction, money orgasming directly from my account into hers, I could no longer deny my orgasm, and spurted powerfully into the panties that had teased and tormented me for 24 hours. Oh. Ohhh what bliss ! What relief !!! In that moment, I hope I had satisfied Mistress, and indirectly, two weeks of sexual frustration came spurting out. It rocked me to my core, and I believe that Mistress enjoyed the rush and orgasms as much. Lovely end to a period of intense control in so many ways. Thank You Mistress Jo …. I am very grateful indeed !

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Thank you for my latest punishment Mistress, it both taxed and pushed me to my limits. - Slave P
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I am very naughty as I get very wet whilst waiting for my next punishment and tasking Mistress. - Slave O
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I enjoy it when you TeamView me and I watch as you gather incriminating evidence to use against me Mistress. - Slave B