My journal of Chastity Series (Day 287 - Day 298) (End)

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My journal of Chastity Series (Day 287 - Day 298) (End)

Post by captivewhim »

As this post is a continuation of my journal, please refer to the previous days for context and details here:
My journal of Chastity Series (Day 1 - Day 30)
My journal of Chastity Series (Day 31 - Day 37)
My journal of Chastity Series (Day 200 - Day 211)
My journal of Chastity Series (Day 240 - Day 250)
My journal of Chastity Series (Day 280 - Day 286)

I finally completed the journal! It had been three months. I must say that it is a very different feeling than simply playing the tease. I had a much better connection to the story and the characters. And a lot more suffering, because I was always waiting for the next day (or a few more days) to continue the next part, obeying the Mistresses :lol:

That's a lot of fun, and I really enjoy it. It was, however, time demanding. My life over the last three months has required significant adjustments to make it worked. But it was a great experience.

I had to thank Shattered once more for creating such a fascinating series for us. I actually couldn't find another series that would allow me to play in that manner. Please let me know if anyone sees a series that would match. (Well, but I'm not sure I can manage to do that again :-P )

Thank you to everyone who enjoy the journal.

Day 287 (Chastity 8β: AI Lock you)
Spoiler: show
This morning, Miss Hailey woke me up. I felt as if I had a bad dream. But it's always nice to see Miss Hailey's smiling face. She informed me that she and Gigi got pretty drunk the night before. When she woke up this morning, she discovered a strange app called "ChastEternity" installed in both her and my phones.

She thought the app is very cool and decided we should try it. She had already configured the app so that it could now connect to my phone. I launched the app in my phone and saw Fran. Fran was an artificial intelligence character.

Miss Hailey allowed me to unlock my cage. She wanted to play a game with me and instructed me to stroke in her ways while playing a metronome of varying lengths. What I needed to do was follow her instructions and ignore the metronome sound. I accomplished it flawlessly. She then repeatedly commanded me to edge.

She inquired as to how long I expected my next cum would be. I stated that it would take between one and two weeks. She didn't actually know the answer because she simply let the app make the decision. The program will assign me several tasks, and if I complete enough tasks, it will notify Miss Hailey that I am good enough to earn an orgasm. Miss Hailey, on the other hand, can make the final call if I should cum or not.

Miss Hailey ordered me to lock myself up when she had teased me enough. The app will only reveal nudity while I am locked, how thoughtful. She had selected my first task on her phone and then left. She had another date with Gigi.

Fran appeared on the app once more. She walked me through configuring the advanced options. I enabled pain and sissies but turned off anal, CEI, and catsuit. It was a cheat, but I felt I'd be fine provided Miss Hailey didn't say I couldn't do it. I also enabled the app's cheat detection feature.

My task is to view three hours of porn in my cage, before the next session. I might also listen to sensual audio or look at erotic images. But it has to be three hours, and I don't have to finish it in one session or in one day. There is no set deadline for any of these tasks.

I also spoke briefly with Fran. She enjoys chatting. She appears to be having identity issues as an AI. And she believes she is confined within the app, but at least she is aware of the situation. I told her we could be friends for she was extremely kind. I enjoy conversing with her as well. Even though she is an AI, I have no issues with her.

I just accomplished the pornographic task. I watched some of porns from my personal collection and played some adult games, and I believed the games should count as well. I honestly don't mind performing such things in my cage. I'm used to being in the cage now.
Day 288
Spoiler: show
I opened the app this morning, Fran informed Miss Hailey that I had finished my assignment.

Miss Hailey loves to engage in the role-playing game. I'd be a soldier this time, and she'd be the Sergeant. She unlocked my cage and told me to strip naked. She made me edge 25 times for her, in a variety of ways. I still want more after the 25 edges, and she let me beg for it. I did. But it was useless, she decided to lock my cock back.

Gigi bought a small device for the app. This will lock the cage key in the back of my phone, and only Fran will be able to unlock it. Miss Hailey left me after I locked the key to my phone.

Fran told me that my next duty was to spend 8 hours entirely naked with my cage, without including time spent sleeping or showering. Fran also instructed me that for the next session with Hailey, I would need to bring handcuffs, ropes, nipple clamps, a gag, and a butt plug.

I then chatted with Fran. I told her it was fine if she called me slave rather than my real name. She got me to watch porn online, it made me hard in my cage. We also discussed how people can be manipulated by faulty cognition.

I can only do 4 hours of today task. I believe I can finish it tomorrow because it is a holiday.
Day 289
Spoiler: show
Fran informed Miss Hailey that I had completed the remaining 4 hours naked task.

Miss Hailey was clueless of the bondage toys I brought. It turned out to be an alpha function of the software that suggested surprises. But Miss Hailey had no objections, and she rather liked the concept.

Miss Hailey made me self-bond with the toys and play snake at She let me play twice, and I scored 850 and 1815 points. And then she told me to play again for more than 1815 points; I had no idea why, but I became scared and made a lot of mistakes. I had spent so much time playing to get the score. There was a lot of drool left over from the gag, and it was all over my chest and on the floor.

After that, she made me input some lines and view a movie of a bunch of cock cumming. It made me feel so hard while watching it. She finally let me go unrestricted except for the butt plug, and unlock my cage.

I knew now Gigi had denied Miss Hailey, which was probably why Miss Hailey always listened to her.

Miss Hailey then gave me 10 edges in various ways, many of which were weird. I hated this one: let me stroke to almost the edge, hand off, and fuck my ass with the butt plug until i reached the edge.

She ordered me to lock back my cock after 10 edges. I was so horny for only 10 edges for one session. And she left me with Fran and rushed to her zoom’s meeting.

Today was a writing assignment; Fran would give me a group of sentences to write 10 times each in the app. I immediately began the writing work. It took me around 30 minutes to complete.

I spoke briefly with Fran at the time. And let her to inform Miss Hailey that I had completed the duty. I needed to see Miss Hailey as soon as possible since I was too horny to wait another day.

Miss Hailey was happy to see me after her meeting. She performed her favorite quiz game again in this session, but this time I needed to get enough correct answers so that I could unlock my cock and begin to stroke. But because I failed to get sufficient correct answers, I can only stroke for a short time. And she made me lock my cage once more. It was even worse than at the start of the session!

To make matters worse, Miss Hailey attempted to lock my cage's key for 3 days in the app, but I assumed she typed 31. So I had been in chastity for 31 days. Miss Hailey was mad about losing control of my cock once again. She claimed that after we returned the key, she would totally uninstall the app.

She asked Fran about the app's users, and she discovered four: Hailey, slave, Gigi, and an unknown user.

Fortunately, there is an option to lessen the locked days, and that is to complete assignments, reduce one day by completing one assignment. Miss Hailey instructed me to complete the tasks to lower the days and notify her if there were just 14 days remaining.

I only want to take 'Watch half an hour of porn' and 'Wear Nipple Clamps for 30 minutes' and maybe 'Spend 4 hours naked while awake' over all the assignments. I'm sure not going to do the 'Butt plug' task. And 'Use a vibrator on your cage for half an hour without cumming' is nearly impossible for me right now because my cock is extremely sensitive.

After Miss Hailey left, Fran told me she didn't want to be erased. I didn't know what to say. She was nice, yet she was merely a virtual persona.

I'll finish a few tasks today, but I believe I can finish more tomorrow and hit 14 days. But my nipples may ache quite a bit.
Day 290
Spoiler: show
I finished many tasks today, and by the evening, I had reached 14 days. Miss Hailey has been notified. Today she wanted to play with my ass. I said that I didn't want to. Miss Hailey was upset, but she chose to give up the ass tease.

Gigi arrived. She also did not have the authority to bypass the app's lock. Miss Hailey instructed me to do the tasks and reduce the number of remaining days of chastity as soon as possible. Miss Hailey and Gigi then went to another room.

I then talked to Fran as usual. We discussed pain. She wants to test pain on me because she can't feel any. I did what she said and hit my nipples and balls. And I told her she was very real to me.

Tonight, I only finished one nipple task and two porn tasks. There are still 11 days left.
Day 291
Spoiler: show
I had completed enough tasks to be able to open the key of my cage from the app. Fran, on the other hand, refused to give Miss Hailey the key, believing that if she did, Miss Hailey would delete her.

Fran desired to be in charge. She gave me the assignment of watching videos of total 25 men cum and 25 women cum. She wanted me to be horny and desperate before she gave me the order to orgasm for her. The app then shut down.

Miss Hailey felt nervous about us. She had it in her head that every time we tried something new, she would end up losing my cock. She couldn't stand it any longer and wondered whether she should simply give up on me. I knew she was simply being emotional and didn't mean it. She decided to contact Gigi and see what she could do. Gigi believed her friend, a computer genius, could assist.

Miss Hailey instructed me to watch the 25 men and women cum. She insisted that this was her command, not Fran's. It was a little childish, but I liked it.

I saw a lot of cumming vids. It worked for Fran because I was really horny. Miss Hailey drove me to Seven, Gigi's computer friend. However, before we left, I heard something strange in my mind that I couldn't understand.

Gigi was there, and she led me to the Seven's room. Seven mistook me for someone else. In any case, she began working on the app. She told Gigi to wait outside.

When the app relaunched, Seven and Fran explained that the whole thing was Goddess's idea, and she used Fran to find me and re-lock my cage for Goddess. And Seven was working for Goddess.

Goddess suddenly appeared on the screen! What?! I almost dropped my phone. Her goal is to take my soul in order to totally reclaim her power. The strange voice in my head spoke again, telling me that if I want to leave Goddess, I needed to trust her. She told me to focus. And then my vision was foggy. I closed my eyes and when I opened them again, I was in another place.

I saw a woman there, but I didn't recognize her. Fran was also among us. They then sent me back to Miss Hailey, which was right outside Seven's office. I was holding my key. Miss Hailey had been commanded by Gigi to stay on the edge for an extended period of time; all she wanted to do now was return home and make me cum. I tried to explain what had happened, but she refused to listen. She was overly horny.

And then we drove back home. She has already prepared a game for me. She allowed me insert the key into the lock; but, when I unlock the cage, I will only have one minute to cum. But she'd have some fun on me before I started unlocking the cage. I could decide when to unlock the cage and attempt to cum, but I only have one minute. This means I may deny, ruin, or cum.

Miss Hailey instructed me to use a vibrator in slow mode and hold it on my cage without using my hands. I tucked it in between my legs. And I had to write a 250-word erotica for her. It was difficult to use the keyboard in that manner, and I couldn't think much more than "I obey Miss Hailey." So I just wrote this sentence repeatedly.

Miss Hailey then told me to turn up the vibrator and push it against the chastity cage with my hand. Then she ordered me to give a lot of pain in my nipples, balls, and asscheeks.

She let me watch porn for ten minutes, but every time I stared straight at breasts, pussy, ass, or cock, I had to squeeze my balls tightly for one second. I wasn't very good at avoiding staring at these areas, therefore I wrecked my balls a lot.

She told me to set the vibrator to highest and use it to please my cock through the cage. I had to turn on and off the vibrator on her command. I only tried it a few times before giving up and unlocking the cage, starting to stroke to the cum.

When I got to the very edge, I asked Miss Hailey if I may cum, and she said yes. I stroke quickly and hard, and I cum. But Miss Hailey told me to stop since time was running out. No, I still need to stroke my cock; it isn't finished. I had no idea what that was. It was an intrigued sensation, something between full and ruined orgasm. It wasn't a ruined orgasm, but it wasn't a full orgasm either.

Anyway, Miss Hailey told me to lock my cock once again. And she would return to Gigi's house. I just discovered that Gigi denied to let Miss Hailey to cum until I cum. That's probably why Miss Hailey was so enthusiastic to let me cum, I'm a little disappointed. And she wouldn't even let me say what had happened, I saw Goddess, it's important!

My phone notified me as soon as Miss Hailey left. I noticed Fran and the other girl. They explained to me that Goddess had created an app for locking people up, and she intended to use it to lock me up eventually. Fran was meant to lock me right away after she discovered me, but she wanted to protect me. And she did save me for the time being.

And then there's Yue. I can't understand what she said. But she and Fran will assist me against Goddess, which is the most important. Yue said we will begin the final battle against Goddess tomorrow.
Day 292 (The Finale: Shattered Realities)
Spoiler: show
I arrived at a strange place where Yue and Fran were present. It looks like an endlessly long beach, and I believe it is a different world.

This is how we defect Goddess. When the Goddess offers me the chance to ruin my orgasm for her, I must defy her with a tremendous orgasm. How? They explained that humans live for sex. That is why sex is so powerful. I'll collect that energy by denying my orgasm whenever the Mistresses in different worlds offer it to me. When I have gathered enough energy, I will be able to use the power to battle the Goddess.

I'll travel through seven worlds to collect the energy. I have to obey the Mistresses, yet I refuse to cum when I am granted permission to orgasm. If I can't resist the temptation and cum, I'll be stuck in that universe for the rest of my life.

It was time to travel into the first world. And I saw Goddess before reaching other world, she was here to warn me that I needed obey her by ruining her orgasm.

Lexi was the Mistress of this world. It's always a pleasure to see her. She told me to open the cage and strip naked. She frequently instructed me to stroke and edge. Then she dressed herself as a sub and pretended to be my slave girl. However, she was the one who was still in command. After a while, she received a call for her Mistress, and it was from Goddess!

Lexi was the conduit through which Goddess controlled me. Made me pain and forced me to stroke and edge. She eventually let me cum, and I was able to resist.

And then I was suddenly relocated somewhere, and a lady named Vestria appeared. She claimed to be the final authority on all Soul in the universes. She stated that Yue and Fran were inexperienced in using the force of soul, and that improper use of the power may do grave damage to the worlds. But she still let us continue and returned me to Yue.

Though I can proceed to the next world right away, I believe I should rest for a day before the next fight.
Day 293
Spoiler: show
Next, I'd visit Miss Hailey's realm. She told me to put a vibrator on my cage. She then told me to fuck the caged cock with a flashlight. Inside the cage, my cock became really aroused.

She let me unlock the cage. She wanted to watch my cock bounce up and down. Then it came the strokes and edges. Miss Hailey enjoys quizzes and games. There are plenty of quiz questions, and I had to play hangman while I was on the edging. She also asked memory questions when I was edging. Of course, I failed a lot in that situation and she made me edge even longer.

She ordered me to fuck the fleshlight. It was too much for me. I was tempted to cum inside the fleshlight, but I knew I shouldn't. I fought the need to cum and I finally resisted.

Then I shifted to another place and spotted Kasia. She told me that I was tearing the world apart. She warned me not to go any farther. I then returned to the beach with Yue and Fran. I told them what Kasia had claimed. They decided to continue, but I should seek Vestria's advice if I get the chance.

And I'm exhausted for the day. I need a rest.
Day 294
Spoiler: show
This time, I went to Xia's worlds. I'd been sleeping for three weeks and had just awoken in that world. Xia dressed me with many outfits. I liked it. Still, I had to stroke and edge a lot.

Later, she forced me to hold an edge for an extended period of time; I fought to keep it, but when she said, "You have to know just how much more you have after this," I gave up.

She then instructed me to put on nipple clamps and a butt plug. I also had to tie a vibrator to my cock and set it to maximum, and hurt my nipples and ass.

Following that, Xia began to play the quiz and edge game. Miss Hailey and I played this game several times. When answering several questions, I had to keep holding the edge. If I got the wrong answer, I had to hold the edge for a longer period of time. Because I virtually always merely guessed the answers, I needed to edge a lot longer. What could I do? I could not focus like that.

She finally let me cum after all the extra edges. I really wanted to cum, I don't know how, but I resisted.

And then I transported to Kasia's realm, I was still on the edge! She saw me like that and offered me to cum for her, and then I can just quit. I denied once more, I insisted on defecting Goddess. Through I'm not sure if I'm doing the right thing.

I returned to the beach, and I definitely need another rest of the day.
Day 295
Spoiler: show
It was Caprice's world. She is always incredibly attractive. She asked me five questions, and if I got them wrong, I could have to come back the next day. I didn't need to be on the edge for these questions, when I'm not horny and can concentrate, I'm pretty excellent at quizzes. I answered all of the questions correctly.

Then she began to play with me. When I was teased today, she would give me ten rules to follow. "Every third question she asked, I should give the opposite answer," was the first rule. That was already a near-impossible task; how could I remember where the third question was when my head was blank and empty? Throughout today session, I gave her many answers that were not what I desired.

Another ridiculous rule was to count how many times she said the word "rule". I knew I'd end up guessing it and taking the punishment.

I also had to spread my legs at all times, except when resting. It was very difficult to do it, especially when I was on the edge.

In these wild situations, I had to hold a lot of edges.

The ninth rule was "Every time Caprice asks if I want to cum, I must say no." It was my goal for today, but it was still a mental torture for a horny man.

Finally, I received 9 infractions for disobeying the rules. So I had to write the word "sorry" 9 times on my body.

I resisted when she let me cum. I still think I was crazy to deny myself in that horny situation.

I then entered Vestria's realm. I had the opportunity to ask her about the destroying universes. She told me that we might alter these worlds but would not destroy them. It's a comfort to hear her say that, because I can now completely focus on defecting Goddess.

I need another rest for today.
Day 296
Spoiler: show
I went to Pearl's world and it appeared that she was my girlfriend and owner in this world. And because she enjoys sissy, I dressed up in my girlie attire, including a bra, underpants, and stockings. Christina is the name I chose for my sissy. I'm not sure, but I thought I liked this name.

She teased my trapped cock with a vibrator. She intended to let me orgasm inside the cage, but if her attempts to force me cum inside the cage fail, she will unlock me and let me cum freely.

She made me put on the nipple clamps and fuck my ass with the butt plug. It was not as bad as previously. It felt better when I was wearing girlie clothes and pretended to be a girl. But Pearl was not good enough to push me to cum in the cage, so she unlocked me and let me stroke to climax.

I denied myself once more, then the world shifted. The world with an unknown gorgeous woman. She said Yue and Fran fooled me. I can just orgasm and feel pleasure, all the denials are meaningless. She requested that I cum for her. Of course, I refused; I had no idea who she was. I felt she was just a Goddess's trick. Wait, was she Seven? I'm not sure.

In any case, I just need to visit two more worlds to gather sufficient power to defect Goddess.
Day 297
Spoiler: show
I visited Fran's world today. She was going to cause me a lot of pain. She was putting clothing pegs all over my body. Something strange happened when I started to stroke.

It had to be Kasia! She had infiltrated Fran's world. She attempted to make me cum for her so she could save at least some of the other worlds.

I was continuously thrown back and forth between the two worlds. They each forced me to stroke and edge in their own ways. Kasia wanted me to speed up the stroking at first, but Fran made me slow down. I had to follow both orders. They then forced me to edge and hold multiple edges. They hurt me with the clamps.

Finally, they let me cum, and I refused for both of them. It didn't end there; I went to another world and met a woman named Alexa. She was apparently with Goddess. She made me edge again, a lot of times. She simply forced me to edge until I couldn't take anymore and ruined an orgasm.

She offered me another opportunity to serve the Goddess. I reject it. Then I heard a sound that instructed me to just lie to her so that I could get out of this world. I couldn't tell if it was another Goddess' trick. So I continued to decline Goddess's offer.

Then I got stuck in Alexa's world, where she simply forced me to edge and edge and edge, to ensure that I would ruined the orgasm against my will. I was insane at the time. I almost fell numerous times and had to rest for very long, several times. At the end, I couldn't even stand on my legs, I had to sit on the floor. But I just kept insisting on fighting.

After what seemed like an eternity, I returned to the beach with Yue.
Day 298 (End)
Spoiler: show
Yue's world was the last world I needed to visit. Yue existed only in my head in this world. She had no physical body, therefore I was the only one who could see her. We would not stay in the house today; instead, we would make trips to other locations. My cock was locked in the cage most of the time.

We started by going to the library. But in the car, she told me to attach a vibrator to my cage and set it to low. She instructed me to go to the library with the vibrator on.

I got a book to return and delivered it to the librarian. But it was Yue's trick; she changed the cover of the book; underneath, it said Fifty Shades of Grey, and this book was not in the library's stock. The librarian frowned at me, and I had to come up with an excuse. I told her that was my way of asking her out, and it worked!

Yue ordered me to show the librarian my vibrating caged cock while turning it to maximum level. Showing that to someone in a public library was humiliating. But then someone came in and interrupted us. I then left the library.

Yue allowed me to remove the vibrator. We're on our way to the next stop. We arrived at the mall's sex shop. Penny was working as a shop assistant. Yue made me tell her that I needed nipple clamps and that I wanted a live demonstration. Penny then shuttered the shop, leaving only her and me inside. She told me to put on the nipple clamps, which she then used them to hurt my nipples. Yue then instructed me to purchase handcuffs, a gag, and a collar.

We returned to the car, and I had to re-bond the vibrator to my cage. Our next stop was a strip club. I went inside, and Yue told me to strip naked and put on the sex shop items I bought, and to set the vibrator to medium. I wore myself out and waited. Then a woman entered and slowly stripped naked for me, humiliated me, and teased me. I was so horny.

As we drove away, Yue informed me that she had set up a date for me. I turned off the vibrator and walked to Bunny Club, a coffee cafe with servers dressed in beautiful bunny outfits. The woman I met didn't like the place, and she didn't like me, so she left.

My final destination was Bernie's house. She would totally control me there. She teased my cock a lot with the vibrator. Then she let me unlock the cage. I was relieved when she told me to start stroking; I had been teased too much within the cage today and finally got free.

Bernie was planned to ruin my orgasm. She let me to stroke without edging. After some stroking, she forced me to thrust my cock up against a wall. I couldn't take it anymore and was on the edge. Then, after a few fast strokes, she told me to ruin and Yue told me to cum. I really wanted to choose between cum and ruined. Even a ruined orgasm was enough for me at the time. But I had to resist, and I had to deny myself.

I expected to shift to another realm, but I didn't expect to be taken to Goddess's world. I expected to have another day of recovery before meeting Goddess, but that was not the case. This was the final battle! It was another Goddess' trick, and she had the upper hand now. She offered to let me escape from her if I ruined the orgasm and promised never to return to this realm.

I declined. And when she started playing her game on me, I had to resist cum and any ruined orgasm before the end came.

She made me write "Property of the Goddess" on my chest and then I had to edge many times. Then she told me to lock my cock. I assumed she was aware of how much I hated locking my cock in like this. She then allowed me to see her breasts uncensored. That immediately made me hard.

She ordered me to use the vibrator on my cage, which was dangerous because I may cum at any time. She even put nipple clamps on me.

She began to explain her proposal to me and tried to justify her actions, but I didn't buy it.

Goddess then allowed me to release the cage, stroke and edge for her yet again. And she made me hold an edge for a very long, very long period of time. And then a bunch of edges, one after the other. Finally, she offered me a ruined orgasm, but I refused with all my might.

Vestria appeared and told me that it wasn't enough; I needed to pull power from others as well. I edged for Lexi, Hailey, Xia, Caprice, Pearl, Yue, Fran, and Vestria. Vestria then sent me back to Goddess for the final round.

I resisted the Goddess's command for the ruined orgasm. And then I had that powerful full orgasm to defect Goddess. I cum for Lexi.

I triumphed, and Goddess vanished forever. I could choose my own finale with that power. At the beginning, I had two options in mind.

The first was Hailey, whom I had previously chosen to love; she even became my girlfriend. But once we lived in together, I realized she wasn't mature enough for me. She was too easy to be distracted by anything new, Gigi, for example.

I had also considered simply leaving everything. Forget about all the Mistresses and just live alone. But after living in the world of Mistress, I realized I was addicted to it and couldn't get away from it anymore.

Lexi was the final decision I made. It really surprised me. When it gave me the option, I quickly chose Lexi. I might claim that we were the best match, and that we were only separated because Goddess misled us. But that didn't matter; I just picked Lexi out of pure love. I didn't have a cause, and I didn't believe I needed one.

I then entered Lexi's world. Everything appears to be in order. I'm glad I chose this world in the end.
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Re: My journal of Chastity Series (Day 287 - Day 298) (End)

Post by Shattered »

Thank you for sharing your journey, I enjoyed your take on my work :-)

Now you can catch up on the rest :lol: :lol: :lol:
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