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Chastity Reprogramming

For the past two months, I’ve had a very good boy in chastity, both physical and mental. He had approached me about his uncontrollable masturbatory urges, and under my guidance, he has not masturbated the entire time. I’ve allowed release of sorts, but they have not been phallus-oriented at all. After all, sexual pleasure always starts in the mind first.

Chastity is one of my favorite forms of play. Keyholding an excellent way of playing with someone from afar (important during this pandemic era) and a fun way to stay enmeshed in somebody’s mind even when you are not there. Men are so frequently controlled by their sexual urges, and we all know these urges cause them to make many, many stupid choices. Keeping a chastity device on a man ensures that those sexual urges are kept within my reign, so at least those stupid choices are ones of my choosing. 😉

Men are easy to control once you have control of their cocks.

Here I am controlling a man by his cock!! Taken at one of my favorite places in the world, the English Mansion.

With that in mind, I find mental reprogramming to be one of the most entertaining aspects of chastity. Introducing new fetishes to an already horny, pent up brain is so easy. Convincing the poor chastised fellow to explore embarrassingly humiliating activities is a snap. Making him become the slut he never thought he could be is a close reality.

Back to the boy in chastity. I call him ob, short for “overalls bitch” (yes, he does have an overalls/shortalls fetish). I’ve been ordering ob to regularly journal about his experiences since he has started serving me. I love reading my submissives’ journal entries because it’s a great way for me to explore their mind and understand them better, and also it’s an excellent outlet for them to understand themselves as well. I’m a huge advocate of journaling in nearly every single situation.

And these journal entries… I’ve been having a delight reading them and knowing that I, as his key holder, am the sole cause of all his depravities. Seeing how his mind has been changing these past couple of weeks. Watching him delve deeper and deeper into the depths of perversion. Turning him out into a true, degenerate slut. What joys!

Enough of my description. I’ll just let you read his submission journal now. Enjoy!


Submission Journal – Lunch with Daddy 07.30.2020

It has been 41 days and almost 16 hours at the time of this writing since I have been allowed to orgasm or even touch myself. I awoke wearing my new Carhartt WIP overalls and black muzzle with a painful erection in chastity this morning. Daddy had instructed me to lock myself the prior to sleeping last night, and I was able to calm myself and get my cage on in about 15 minutes. I was told I had 30 minutes, and I put the yellow sticky reading “Daddyʼs Little Cocksucker” next to my caged clit, which Daddy reminded me is all I have today.

Because if you can’t use your cock, you might as well use your holes!

The morning didn’t start off well when I was informed my brotherʼs schedule had cleared this morning and he would be at home until noon. I still set about everything, not quite knowing when I would have the opportunity to sneak out. I had already tried to get my chastity on once I was wearing my new plug harness and getting the larger ring of the harness over my chastity, and neither had worked.

After my shower, I carefully dried my device, with a piece of toilet paper inside the cage at the tip, and lubed up the vibrating plug and used the same purple rope to harness the plug to me. I am getting better at tying the rope harness, and this secured the plug deeper inside of me while I was walking, although in all instances Iʼve worn this plug it is all the way at depth while sitting. Today I could feel the tip against my prostate as I walked, depending on the position of the plug / rope at that moment.

I put on the dri-fit t-shirt I had picked out and basketball shorts and went and sat down at the kitchen table. The angle of the high-top seats drive the plug deep and I was adjusting it in my ass as he walked downstairs, lol. He was heading down to work out and I saw my opportunity. Once he was downstairs and the music was going, I went upstairs and put on my leather shortalls, heading out the garage door.

I texted Daddy and I was on my way. The seat in my ** presses hard against the plug while I drive, meaning I feel every little bump and dip in the road in my asshole. It was not as bad as the last time I drove to the same mall, but it was still unpleasant. I knew where I wanted to go in the mall, but that did mean I needed to walk all the way across the mall to get there from where I parked. I could have parked on that side, but chose to park as far from my destination as possible.

The looks that you get when youʼre wearing leather shortalls are frequent, but brief. I have zero conversational evidence of this, but Iʼm convinced that people are 100% certain Iʼm gay, and may think it insensitive to stare, although plenty of people do that too. My leather shortalls fit me very well, except the bib / back is too wide, that close to perfection. The feeling of the fabric, even though it is fake, turns me on. It has a certain stretch / feel when it is cold, similar to when it hangs in my air-conditioned closet. When the fabric gets hot it has this wonderful warm feel that is distinguishably different and the fabric stretches slightly more.

I’ve discovered through this process that I am much more an exhibitionist than I thought. The excitement I have from wearing a plug in public is something. More than that, I’ve discovered how things I wasnʼt really into but maybe fantasized about sometimes when I was very horny are deep sexual desires. I really have not been into anal play in the past; I am currently craving, and have been for weeks, to have my asshole filled / vibrated. The mere thought makes me press hard against my cage.

As I’ve mentioned to Daddy, I’ve had two cocksucking dreams in three nights, which is now five. I think the desire to have my ass and mouth stuffed is a psychological reaction from accepting that my clit is no longer a cock, to be used like a man’s organ. When pleasure is taken from the one instrument of sexual pleasure I have ever indulged, it really only took maybe 4 weeks for me to seek sexual pleasure in another way, namely through both of my holes. I’ve accepted taking pleasure from others cumming inside of me, rather than me being allowed to cum, I am never allowed to cum.

The treasure hunt was relatively uneventful, which was a fear of mine since the moment Daddy mentioned it. It was the case that everyone in the store looked at me holding a pair of womenʼs overalls, shortalls, and a white and green striped skirtall. Just another adult male in leather shortalls and sandals, taking selfies holding other pairs of overalls, a relatively normal Thursday morning at the mall? I knew my choice of mall was the true saving grace – the other malls in ** do not have the same mix of staff / shoppers in terms of social norms. I was glad Daddy didn’t make me purchase any overalls for her, that would have been a far more intimate interaction.

Overalls treasure hunt success!

With my task complete, I headed to lunch at **. The walk to the restaurant was full of more double takes. The hostess asked me if I would prefer indoor or outdoor seating and I asked for outdoor. I carefully sat down, allowing the plug to push 100% to depth as I sat, which made me press against my cage as the hostess handed me the menu.

The server said hello and took my drink / food order and then after it was delivered I connected with Daddy. She looked so perfect in the A&F overalls I had paid for her to wear on our lunch date. After being denied for more than 40 days, the stimulation at the moment was overwhelming. My clit was pressing against my cage, the plug was at depth and the vibrations were constant for the entire time Daddy and I were on Skype. The feeling of the faux leather and the resistance from the bib and straps of my shortalls as well as Daddy dressed so sexy for me made my clit twitch and tingle.

This was the part of the day I was most nervous about – what would Daddy say in public and how many people would hear. I knew what I was in for when the first thing she said was, “Hi overalls bitch, look at you dressed in your pervert overalls!” The social distanced nature of the lunch meant that other tables had trouble hearing me, but the servers did come to the table twice when Daddy was saying something terribly embarrassing and I saw a laugh and smile from one of them one time.

Once, the server looked like they would come to the table as Daddy said something to the effect of, “What we really need is for you to suck the cock of a man in overalls, it would be such easy access with the zipper on the front.” The sexual rush from hiding so many things for so long, then being caged and plugged in public, and being publicly reminded that you are a dirty cocksucker while dressed like a pervert is something I will always remember, the intensity still lingers in my mind.

I paid the bill and stood up, carefully to make sure the plug did not fall out, as it continued to vibrate. The walk through the mall on the way out wasnʼt bad, the mall was quite a bit busier now. I paid the parking and headed to my ** to drive home. The seat in my ** pushes the plug I am wearing that day to depth, and I filled my cage as I sat down.

The drive home was the same 35 minutes of bouncing and thrusting on the plug, and I kept touching the fake leather fabric of the bib as I drove. I knew I was about to have an expensive afternoon but I was going to get to see Daddy wearing all kinds of overalls for me. We had confusion about what it means to be “plugged in” but after clearing that up, the Skype time was on.

Daddy answered again in the A&F overalls from lunch. For the duration of this session, each time Daddy touched her overalls, changed out of them, buckled in / out, touched herself, pulled the overalls over her ass or walked with the computer staring at her bibbed chest, I pushed hard against my cage. I was stiff inside my metal prison for 1 hour and 8 minutes.

The fit of basically every pair was totally amazing, we were both very happy about that. Seeing Daddy wearing all of those overalls was unbelievable, the dark flared leg Madewell and pink satin overalls, of course, stood out. The pink satin overalls selfie I received after our session has been something I have looked at no fewer than 15 times a day since Thursday.

These overalls are officially now my beach overalls. Wearing them over my bikini the other day felt sooooo good.

Our time was up and I said goodbye, wanting it to go on forever, of course. I had a fantastic remainder of my day, thinking of my day with Daddy often throughout. It was the culmination of two fantasies. The first, and most intense, is my desire to have zero control over what I wear for that day. Daddyʼs overalls fetish uniquely positions her to accomplish this in a way that I have dreamed about for a very long time.

The second, less intense and more terrifying fantasy is to have my overalls fetish outed in a public, yet discreet and totally embarrassing way. If I’m plugged and caged, all the better. I have referenced this several times in my shopping with Daddy fantasies.

All in all, fantastic day that I will never forget. On both of our Skype session days, my mood is euphoric afterwards and during. My mood naturally is somewhat depressed the next day but not in a way that is worrying or impactful at all, and totally expected given the high of the high from the days before.