My journal of Chastity Series (Day 1 - Day 30)

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captivewhim
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My journal of Chastity Series (Day 1 - Day 30)

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I played the web tease called "Chastity 1: A day with Lexi" by Shattered. I had planned to go through the entire series and experience what it had to offer. As I finished the first tease, a sudden idea struck me. What if I wrote down my thoughts, experiences, and fantasies while playing the tease?

Excited by the notion, I started documenting my journey over the next few days. But then, another idea emerged, what if Mistress Lexi commanded me to write a daily journal about her dominance and instructed me to share it with the world.

The moment I received this assignment, a wave of arousal washed over me. The prospect of sharing my submissive experiences with others thrilled me to the core. And so, here we are, embarking on this journaling adventure together.

Please keep in mind that this journal may reveal significant aspects and surprises. If you haven't had the chance to experience the teases yet, I would recommend playing them first to fully immerse yourself in the innocent and submissive journey they offer.

Day 1 (Chastity 1: A day with Lexi)
Spoiler: show
Today, something really surprising happened to me. I was walking down the street when a woman, who seemed quite friendly, approached me. She told me something that left me completely taken aback. She claimed that she had seen me from outside my window while I was masturbating. I felt so embarrassed when she mentioned that she had recorded me on a tape. She even gave me an address and said I should go there tomorrow at 6 pm, or else she would share the video online.

I must admit, there have been times when I forgot to close the window while masturbating, but I never thought someone would actually see and record it. It's hard for me to believe that this has happened.

I'm not sure what to do now. It's not a life or death situation, but the thought of my friends coming across that video is just too embarrassing. It's really troubling me.

I think, for now, I should at least go tomorrow and see what she wants. Maybe there's a way to resolve this situation without anything bad happening.
Day 2
Spoiler: show
Today, I went to the address at exactly 6 pm as the woman had instructed. When I arrived, I saw Mistress Lexi waiting for me. (She made it clear that I must address her as Mistress from now on.) She used the video she had as a means to blackmail me into following her orders, or else she threatened to release it.

It's really hard for me to believe that I actually went along with her demands. She forced me to undress and stroke my cock in front of her. I felt so uncomfortable and shocked by the situation, but I felt like I had no other choice.

At first, I tried to resist and protect myself, but Mistress Lexi punished me by making me hit my own balls. It was incredibly painful! So, in the end, I realised I had no option but to comply with her orders.

She also made me edge myself and hold the edges multiple times, but I wasn't allowed to climax. It was excruciating to hold back the urge to release.

I have to admit, it felt strange and humiliating to engage in these actions in front of a woman. However, I don't understand why, but part of me felt some strange sense of satisfaction. It's confusing and I don't know why I would feel that way. But no matter what, I feel completely under Mistress Lexi's control now.

She outlined the rules I must follow:
1. Obey everything she says without hesitation.
2. Address her only as Mistress.
3. Only speak when replying to her.
4. No climaxing without her permission.
5. She owns me.

I'm really troubled by this situation, and I'm not sure what to do next.
Day 3 (Chastity 2: Days in Chastity with Lexi)
Spoiler: show
Today, when I arrived at Mistress Lexi's house, she asked me to repeat the rules again. But this time, she added a few more rules that I must follow:

1. I must not cum without her permission.
2. If I accidentally edge before she tells me to, I have to pinch my nipples until I feel I can stroke again, even if I'm wearing clamps!
3. I must obey everything she says without hesitation.
4. I can only address her as Mistress or Mistress Lexi.
5. I should only speak when replying to her.
6. She owns me, and I should never forget that.
7. I have to watch at least half an hour of porn every day, which she wants to ensure is a source of suffering for me.
8. If I accidentally start to cum, I have to let go and ruin it. Then, I have to lick up all the cum without hesitation. Afterward, I must lock up my cock and roll a six-sided dice. The number it lands on determines how many days I have to wait before seeing her again to continue where I left off, while she tries to forget my "incompetence."

Mistress Lexi was dressed only in a shirt with nothing at the bottom, and her amazing body made me feel aroused just by looking at her.

She instructed me to stroke and edge while repeating certain phrases for her. One of them was something like, "I want to put on a chastity device for Mistress." It felt strange to say it, but while I was edging, it was difficult to think clearly, and I could only follow her orders.

Then, Mistress Lexi made me hold an edge and explicitly asked if I wanted to wear a chastity device. I tried to gather my thoughts and realised that deep down, I didn't want to wear it. So, I mustered the courage to say No to Mistress Lexi. However, she forced me to continue holding the edge for a longer time. Eventually, she asked again if I wanted to wear the chastity device. I could see that if I said No again, she would make me hold the edge for an even longer duration. In that moment, I realised that I couldn't resist her, and reluctantly, I said Yes to the chastity device.

Mistress Lexi seemed pleased when she heard the 'Yes' come out of my mouth. She even gave me a choice to stroke a little longer or stop then and there.

She handed me the chastity device, and I obediently put it on my cock. As I locked it, Mistress Lexi reached orgasm at the same time. It's unfortunate that she can experience pleasure whenever she wants, while I can only do so with her permission.

Seeing the chastity device on my cock made me realise that I've lost control over it. Just as Mistress Lexi said, she now owns my cock and, in a way, she owns me.

Mistress Lexi instructed me to meet her tomorrow and asked me to bring a vibrator and a pair of nipple clamps with me. I'm not sure how I feel right now, is it fear or excitement? It's a mix of emotions that I'm finding hard to decipher.

After watching porn for half an hour as instructed by Mistress Lexi, I finally understood why it was considered a form of suffering. It was all because of the chastity device she made me wear.

While wearing the chastity device, my cock couldn't grow freely, but when I watched porn, it tried to get bigger against my will. It caused a lot of discomfort and pain inside the device. I didn't know why, but it would shrink back quickly, only to grow again and hurt even more.

The worst part was that my penis had become incredibly sensitive, but I could not touch it. It felt like a never-ending nightmare. I couldn't help but wonder if I would go crazy having to go through that every day.

I'm feeling excited about seeing Mistress Lexi tomorrow. I hope that she will unlock me and give me instructions to touch myself. I really need that right now. Please, Mistress.
Day 4
Spoiler: show
Today, Mistress Lexi called me her slave. I wanted to tell her that I'm not really her slave, but rather I feel like I have no choice but to do what she says because she has a video of me. She's using it to make me do things. It's like she's blackmailing me. But the truth is, I've been doing everything she tells me to do since the day we met. Does that mean I'm actually her slave now? I don't know.

Unfortunately, Mistress Lexi didn't allow me to unlock my chastity device today. I've been incredibly horny since yesterday, and it only intensified.

Mistress Lexi instructed me to undress and then insert a vibrator into my anus. I didn't enjoy that sensation, but it caused my cock to grow inside its cage, resulting in pain. Furthermore, Mistress Lexi ordered me to put nipple clamps on, which caused a great deal of discomfort. But it seemed that Mistress Lexi derived pleasure from my suffering.

After some time, Mistress Lexi forced me to whip off the nipple clamps. It was extremely painful, but it led to her experiencing an orgasm. It was clear that she enjoyed witnessing my anguish.

Today's session ended quickly, and I yearned to touch my cock, but I couldn't. Instead, I was left feeling very sore. I don't feel good for this session, but I have no control over the situation.

Towards the end of the session, Mistress Lexi instructed me to gather several items: nipple clamps, a vibrating butt plug, a collar, another vibrator, a ring gag, a blindfold, some ropes, and lube.

Mistress Lexi mentioned that I would only need the nipple clamps for our next session, but she also hinted at having a big plan for me. Yesterday, I thought it would simply involve extended stroking and edging without release, and I believed I could handle the frustration if it wasn't too long. However, now I'm starting to worry. The array of tools and the mention of more suffering have left me unsure of what I've gotten myself into.

Mistress Lexi told me that she will be busy tomorrow, so we agreed to have our next session the day after tomorrow. She called it a "date" at first, but then quickly realised that it wasn't an appropriate word to use. She ordered me to hit each of my balls ten times as a reminder that she is completely in control. Even though she corrected herself, I couldn't help but feel a little happy when she mentioned us "dating." Mistress Lexi is such a beautiful woman, and maybe, just maybe, we could go on a real date once all of this is over, if it ever ends.
Day 5
Spoiler: show
I didn't go to Mistress Lexi's place today because she told me she wasn't available. It means I didn't have a chance to unlock the cage and touch my cock again. It's only been the second day without touching myself, but I'm starting to feel like I'm going crazy. Usually, I can handle not touching myself for a week, but this time it's different. I find it really hard to bear just two days without any relief. To ease the horniness, I've been rubbing my inner thighs a lot. Maybe it's because I know I can't touch my cock that's making me feel this way.

Today was the first time I went out with a friend while wearing the chastity device. It was actually okay, except I had to be careful about when I needed to use the toilet. I had to use the restroom stall so I could sit down to pee. (Yes, I have to sit down to pee now, or it could get messy.) And, of course, I had to constantly remind myself to be cautious and protect that area. If my friend found out I was wearing the chastity device, it would be just as embarrassing as if they saw the video Mistress Lexi has. Both situations would be equally embarrassing for me.
Day 6
Spoiler: show
When I arrived at Mistress Lexi's home today, she mentioned that she was expecting someone else. Does that mean I'm not her only slave? Wait, why did I even think that? I'm not her slave, just someone who follows her instructions!

Anyway, I felt a little upset when I heard her say that. I thought I was the only one. And she seemed to have forgotten about our "date." She also mentioned having a crazy day yesterday, and I'm really curious about what happened. The truth is, I want to know everything about Mistress Lexi.

But does it also mean that Mistress Lexi has a lot of experience with domination? Did she already have a whole plan for me from the beginning?

Mistress Lexi allowed me to unlock the cage today. Finally, I was able to free my cock. She ordered me to get naked, stroke and edge while repeating the 8 rules. It felt so good to finally be able to touch myself.

Mistress Lexi also insisted on putting the nipple clamps on me, and it hurt a lot at first. But after a while, I started to forget about the pain.

Later on, Mistress Lexi surprised me by asking me to write down the 8 rules on a piece of paper while I was on the edge. I didn't expect that, and it was really hard for me to think clearly when I was so aroused. I could only remember 3 of the rules. It's a shame that I couldn't make a good impression on Mistress Lexi. I should have paid more attention to what she said instead of just focusing on her incredible body.

Since I failed to remember all the rules, Mistress Lexi gave me another chance. She allowed me to repeat the rules while stroking and edging, and she asked me to write them down again. But once again, I couldn't believe it, I failed. This time, I could only remember 7 rules. I forgot the one about only speaking when answering Mistress.

Mistress Lexi let me repeat the rules and write them down again. But there were too many edging and stroking for my horny cock. I accidentally orgasmed, which meant I had to ruin the orgasm. It was completely unsatisfying. There was a lot of salty cum, and I had to lick it all up. It felt embarrassing to do it in front of Mistress Lexi.

Mistress Lexi then had me throw a dice, and it landed on 4. That means I have to wait for 4 days before I can see her again. I have to lock myself up once more.

I have to make sure I remember all the rules before I see Mistress Lexi again. I don't want to disappoint her once more.
Day 7
Spoiler: show
I started watching some of my favourite videos from my old hard drive. They were the ones that always made me feel excited and happy. But this time, something strange happened. My penis only got a little bit bigger for a moment, and then it stayed small the whole time. But there was a lot of pre-cum coming out, even though my penis wasn't fully erect. I don't understand why this is happening. Is it normal? This is the first time I've ever worn a chastity cage, so I'm not sure what to expect.
Day 8
Spoiler: show
In the previous session, I accidentally ruined my orgasm and had to lick up my own cum in front of Mistress Lexi. Every time I recall her laughing face, it fills me with a deep sense of humiliation. It's as if her laughter reinforces her superiority over me. It's a conflicting feeling because deep down, I still believe I'm not her slave.

So, I've made a promise to myself. From now on, I’ll do my utmost to resist the temptation to orgasm without Mistress Lexi's permission.
Day 9
Spoiler: show
I am so proud of myself! I can recite all eight rules for Mistress Lexi by heart now. I repeat them like a mantra throughout the day, ensuring they stay deeply ingrained in my mind. There's no chance of me forgetting these rules; they have become an integral part of my thoughts and actions. I hope my dedication and effort will bring pleasure to Mistress Lexi.
Day 10
Spoiler: show
I felt a bit disappointed when I rolled a 4 on the dice after my ruined orgasm last time. But maybe it's actually a good thing because it gives me time to reflect on the situation before seeing Mistress Lexi tomorrow.

I'm not really the type of person who hangs out with girls. Most of my friends are guys, and I've never had a girlfriend before. I usually masturbate by myself at least once a week. For years, I've been visiting milovana.com and following the jerk off instructions of the beautiful girls on the computer. It's like my little secret.

Of course, I've always had fantasies about obeying a real-life Mistress, but it's always just been in my imagination. I'm not a brave person, and I'm scared to actually pursue any of it. I'm afraid of how it might change my life. I've always been more comfortable following others rather than taking the lead myself. That's just who I am.

So here I am, being blackmailed by Mistress Lexi. According to her rules, she owns me, and I have to obey her without question. And I have been obeying her. Can I do anything else? I've tried to resist, but her punishments have forced me to comply. Can I just walk away from all of this? I'm too terrified to even think about what would happen if my family and friends saw the video.

I can't think of any way to escape this situation on my own. It's too embarrassing to talk to anyone else about it. No one should know!

For now, all I can do is what I've always done best my whole life: just follow along. Follow Mistress Lexi's rules, her commands. I'm scared of what she might force me to do next because I have no idea what it could be. But I'll take whatever the world throws at me. Maybe something good will eventually come out of it. That's how I've lived my life up until now.
Day 11
Spoiler: show
I finally had the opportunity to see Mistress Lexi today. Just like last time, I repeated the rules while gently stroking and edging myself. I also managed to write down the rules while holding the edge. I succeeded this time, although I did get a bit nervous in the middle and almost forgot one of the rules.

Mistress Lexi then instructed me to speak the rules aloud to her. She even added a new rule, making it rule zero, stating that I have to read her rules out loud every day.

During our session, Mistress Lexi asked me if I would still be obedient if she told me I couldn't cum today. I responded with a sincere "Yes." Truthfully, I didn't expect to be able to cum today anyway.

Mistress Lexi proposed a game for us to play. She ordered me to get soft and edge myself, while she had a specific time in her mind. If I could guess the exact time and edge at that moment, I would win and receive a reward. However, I couldn't guess it correctly. Mistress Lexi revealed that she was thinking of a time between 120 and 140 seconds, but I guessed around 60 seconds instead.

As a result of my incorrect guess, Mistress Lexi decided to end our session. I'm quite curious about what would have happened if I had guessed correctly.

Then, Mistress Lexi asked me whether the chastity device is perfect for me or not. I hesitated for a moment before answering. She explained to me that having the chastity device on is necessary to prove that I belong to her.

To express my gratitude to Mistress Lexi, she ordered me to get on my knees and repeat some mantras. Afterward, she decided to schedule our next "date" by rolling a dice. The dice landed on 2, which means I will see her again in 2 days.
Day 12
Spoiler: show
I had a thought today after reading Mistress Lexi's rules as she instructed. I wondered why I should continue reading them or following her orders when she's not around. I mean, she probably wouldn't even know if I didn't read them, right? It feels strange that I didn't question it earlier and simply did as she said.

Does this mean that it's just my nature to follow orders without thinking? It's making me doubt myself now, as if I'm truly that kind of person who always follows others without questioning whether it's right or wrong.

Sure, the blackmail video is the reason why I'm doing all of this, but if it's as simple as that, then I shouldn't have to follow Mistress's instructions when she's not present. Did Mistress Lexi just reveal my true nature? Am I really a submissive slave? No, no, no. I can't accept that. I'm not a slave, maybe I am just someone with a slight tendency towards submission.

After pondering over these questions, I've come to realize that I will continue to follow Mistress Lexi's orders. I can't explain why exactly, but something inside me tells me that I have to obey her. It doesn't make much sense logically, but I feel compelled to do it.
Day 13
Spoiler: show
I brought everything Mistress Lexi told me to last time. She mentioned that I wouldn't be allowed to unlock the chastity device today, which made me a little nervous.

The session began with me being blindfolded, bound, and adorned with various devices like vibrators and clamps. I could sense Mistress Lexi's presence as she watched over me, and I couldn't help but feel a mix of arousal and humiliation. The ring gag was uncomfortable, and it made me slobber uncontrollably, creating a mess all over my body. It was a new experience for me, and I couldn't help but feel submissive and exposed.

After some time, Mistress Lexi gave me a signal to untie myself. When I removed the blindfold, to my surprise, there was another woman in the room. Mistress Lexi was nowhere to be found. This woman introduced herself as Mistress Brooke, and she instructed me to address her as Goddess. It turns out she is Mistress Lexi's Mistress, which means Mistress Lexi is also a submissive.

Goddess commented on how pathetic I was for engaging in such acts and even made remarks about the size of my genitals. It made me feel small and embarrassed, but I couldn't deny the truth of her words. Goddess kept the key to my chastity device and led me to witness the punishment scene of Mistress Lexi.

Mistress Lexi faced punishment because she hadn't informed Goddess about me. I couldn't help but wonder why Mistress Lexi had chosen not to disclose this information. Did she purposely keep it a secret? Was it because of me? The thought crossed my mind, raising questions and uncertainties about our dynamic.

It was a distressing sight, seeing her in chains and being subjected to humiliation. She seemed surprised to see me, and I could sense her embarrassment. The other woman announced that Mistress Lexi's punishment was for me to watch her being punished. As I looked into Mistress Lexi's eyes, I could see a profound sadness that tugged at my heart. I couldn't bear the thought of Mistress Lexi being treated as a plaything. It was a challenging moment for me emotionally, and I wanted to support Mistress Lexi but felt helpless.

The woman mentioned that I would never view Mistress Lexi in the same way again, and perhaps she's right. However, I don't want that to be true. All I wish for is to erase these memories from my mind. But the image of what I witnessed is so deeply etched in my thoughts, and it's difficult to forget.

The woman informed me that it was time for me to meet Goddess. When I met Goddess, she commanded me to kneel before her. I knew I had to obey her as she held control over Mistress Lexi. She mentioned that she would take my first orgasm as a means to further punish Mistress Lexi. It made me conflicted because I didn't want my pleasure to be used in such a way, but I couldn't refuse.

Goddess mocked my size once again and made me stroke and edge while she watched. I couldn't help but feel a mix of excitement and discomfort. Goddess is undeniably attractive, but her focus was on punishing Mistress Lexi through me.

When I finally reached the point of orgasm, Goddess commanded me to ruin it, which left me feeling a mix of disappointment and surprise. It was another unexpected twist in my journey today.

Goddess forced me to rub the cum on my face, and I was instructed not to wash it off before sleep. It was embarrassing and made me feel completely submissive to Goddess's control. I was afraid of anyone noticing the residue on my face, but I couldn't disobey.

To make matters even more challenging, Goddess imposed a rule that if Mistress Lexi were to cum, I wouldn't be allowed to orgasm for a week. It felt like a harsh punishment for both Mistress Lexi and me. I had to deliver this news to Mistress Lexi myself, which was difficult.

Goddess informed me that my next session with Mistress Lexi would be in three days, and she would be filming all the sessions from now on. The thought of being recorded made me uneasy, and I couldn't escape the grip of Goddess's control. It felt like I was trapped in a cycle of submission.
Day 14
Spoiler: show
Every time thoughts of Mistress Lexi surfaced in my mind, I couldn't help but visualize her in bondage and experiencing suffering. It felt as if I had lost control, constantly seeing Mistress Lexi in a state of sadness and powerlessness.

These images made me question whether I could continue to obey Mistress Lexi as I had before. The image of her being a dominant and powerful Mistress was overshadowed by witnessing her submissive side. It became evident that she too was just a slave to Goddess.

I found myself disliking Goddess for her cruelty. She used me as a tool to punish Mistress Lexi, causing pain to both of us. I couldn't comprehend why Mistress Lexi had become her slave.

Now, I need some time to reflect on how to approach Mistress Lexi after everything that has transpired.
Day 15
Spoiler: show
I still haven't figured out how to face Mistress Lexi, but I know I have to see her tomorrow. I'm unsure about what to do or how to act around her.

I hope that she will pretend as if nothing happened and continue to dominate me like before. If she does, I will do my best to also pretend that nothing happened and be her loyal slave. I believe I want to be her slave now, even though I'm not entirely sure what it truly means.

It's not easy for me, as I still have vivid images in my mind of Mistress Lexi being used by others. Whenever I close my eyes, those images resurface. But I will make an effort to act as if everything is fine because I think it will put her at ease.
Day 16
Spoiler: show
I finally had the chance to meet Mistress Lexi again. She looked incredibly beautiful today. However, thoughts of Mistress Lexi bound by chains still lingered in my mind.

She seemed embarrassed about what happened last time, but I could still feel her power over me, and it brought me a strange sense of release. Mistress Lexi remains my Mistress in my heart, and she believes that our relationship hasn't changed.

Although it was Goddess's order that made me ruin my orgasm last time, it still broke the first rule, and Mistress Lexi decided that I needed to be punished for it.

We agreed to modify the rules so that if Goddess orders me to do something, I must obey. I made the choice to stay with Mistress Lexi, which means accepting Goddess as my Mistress as well.

Mistress Lexi's initial idea was to punish me while I was in chastity, but she couldn't bear the thought of another woman being the last one to command my cock. So she allowed me to unlock the cage.

Mistress Lexi commented that my cock looked smaller than she remembered. I don't necessarily agree, but perhaps she sees something I don't.

The punishment she devised involved repeatedly edging and getting my cock soft, all while wearing nipple clamps.

After the punishment, Mistress Lexi added a new rule to our list:
9. Lick up all the precum I produce. If I am gagged, as soon as I am ungagged, lick it all up.

Mistress Lexi climaxed once more when I locked myself back into the chastity device.

I informed Mistress Lexi about the new orgasm rule imposed by Goddess. Mistress Lexi believes that Goddess is trying to create conflict between us. She mentioned the possibility of going a week without cumming, and hearing that gave me a glimmer of hope.

Once I left Mistress Lexi, I received a call from Goddess. Surprisingly, she had prepared a punishment for me in case I hadn't informed Mistress Lexi about the new orgasm rule. But I had already told her, and yet Goddess still wished to punish me for no apparent reason.

In two days, I am scheduled to go to another location, where a slave of Goddess will be waiting to administer the punishment. Goddess presented me with a choice to go or not. I can't believe I agreed to go willingly for my own punishment. Am I starting to develop a liking for BDSM? My mind feels confused, as if something within me is changing.

To make matters worse, when I agreed to go, Goddess instructed me to bring a butt plug, 20 nipple clamps, lube, a gag, a ruler for whipping, and a thin string to connect those clamps together. As soon as I learned what these items were for, I regretted my decision. I already know it will be too much for me to handle.
Day 17
Spoiler: show
I was extremely worried about the state of my relationship with Mistress Lexi after that intense session. However, to my surprise, everything turned out to be okay. In fact, it's even better than before.

Mistress Lexi made it clear that she doesn't need any external factors to dominate me. She is right! She doesn't require a key to my cage or the blackmail video. I must obey everything she says without hesitation. I am truly her devoted slave now.

Why did my mindset change? I can't quite explain it. Perhaps witnessing the vulnerable side of a powerful Mistress made me realize how endearing she is. It's as if I've come to understand that she is my beloved, even though it doesn't quite fit the traditional definition of love. She is my Mistress, and these feelings are beyond rational explanation, they simply exist within me.
Day 18
Spoiler: show
I made a mistake by agreeing to my punishment. Miss Hailey derived pleasure from my pain, and it troubled me greatly. Firstly, I had to use a dildo on myself, which made me feel uncomfortable and vulnerable. Then, I had to instantly remove the pegs attached to my body, causing me pain and discomfort. Lastly, I had to spank various parts of my body, including my cheeks, balls, face, and even the locked belt. Throughout this ordeal, Miss Hailey experienced three orgasms, while I endured three painful experiences.

I must confess, I am not fond of pain, and this punishment was overwhelming for me. Furthermore, it was quite embarrassing to perform such acts for someone I had just met. I particularly disliked the gag, as it made me feel self-conscious about my uncontrollable saliva spilling all over my body and the floor. The entire experience left me feeling exposed and unsure of myself.
Day 19
Spoiler: show
I am Mistress Lexi's dedicated and obedient little slave. She holds complete control over me, and it fills me with delight to fulfill her every desire. I eagerly await our next encounter, where I can serve her with utmost devotion. But it doesn't stop there, for I am also bound to obey Goddess and any other Mistresses that Mistress Lexi or Goddess decree I must obey.

While I find comfort in following Mistress Lexi's orders, I must admit that I do not feel the same fondness for obeying Goddess and other Mistresses. Goddess can be excessively harsh, and I struggle to connect with her methods. It feels strange to be compelled to obey Mistresses I know nothing about, especially when it's our first meeting. It's puzzling how I'm required to submit to someone I have no familiarity with.

Nevertheless, despite my reservations, I am obligated to obey them. It's ironic how, in the past, I resisted Mistress Lexi's commands, but now I am compelled to follow them. It's a similar sensation. Could it be that, with time, I may come to genuinely enjoy following these Mistresses? If that were to happen, would it signify that I am fully immersed in the world of domination and submission? I confess, I am uncertain, and perhaps I don't entirely despise the idea.
Day 20
Spoiler: show
Mistress Lexi looked very beautiful today, especially when she emerged from the bath. Her wet hair and damp clothes ignited a passionate desire within me.

I've learned that Miss Hailey is also a slave of Mistress Lexi, but they share a deep friendship as well. Does this mean that I could become a friend or perhaps even a lover to Mistress Lexi? The thought fills me with hope and longing.

Mistress Lexi revealed that she would withhold her orgasm for me, a reward for my good behavior towards her and Goddess. This act of kindness brought tears to my eyes. I can't believe Mistress Lexi would do such a selfless act for me. She is different from Goddess; she possesses a gentle and caring nature. It's one of the reasons why I yearn to be her devoted slave.

Mistress Lexi has additional motives for allowing me to experience pleasure. She wants my latest orgasm to be dedicated to her, not Goddess. Furthermore, once I climax, she can deny me for weeks without feeling guilty when she requires her own release. This demonstrates her concern for my well-being as her slave.

Mistress Lexi asked me what was missing while I was stroking myself. I couldn't discern the answer, but it was the nipple clamps. As punishment for my incorrect response, she instructed me to slap my balls. The pain served as a reminder that I should always pay attention to Mistress Lexi.

She also inquired about the number of nights I have spent locked in the chastity belt. I miscalculated; it should be 12 nights, not accounting for the nights I broke rule number 8.

Mistress Lexi couldn't contain her own orgasm as she watched me edge for her, wearing the clamps on my nipples. To ensure she wouldn't climax, she compelled me to become soft when she was too hot. In truth, she was doing it all for me.

While I continued to stroke and edge, Mistress Lexi shared details of her initial session with Miss Hailey. She experienced a pang of jealousy over Miss Hailey's breasts, and to assert her dominance, Mistress Lexi subjected her to a tormenting ordeal. For 20 minutes, she played with Miss Hailey's nipples while using a vibrator set to very low power on her pussy. Miss Hailey couldn't withstand the intensity, yet she was powerless to resist.

Miss Hailey has only experienced about six orgasms in the two years under Goddess's control. My heart aches for her, and I hope to avoid a similar fate. I also discovered that Mistress Lexi's greatest fetish revolves around nipples. She instructed me to keep what she shared about the first session with Miss Hailey a secret.

Our next meeting is scheduled in three days, and Mistress Lexi announced that I will be granted permission to orgasm on that occasion. To prepare, she requested that I bring a shoelace, nipple clamps, and some lubrication. The mere thought of finally reaching climax under Mistress Lexi's command has left me longing and aroused.
Day 21
Spoiler: show
I'm still filled with excitement knowing that Mistress Lexi resisted her own orgasm for my sake. Yesterday, she had numerous opportunities to find release, but she chose not to, all because of me. When Goddess introduced that new rule, I felt disheartened, thinking I may never cum again. However, Mistress Lexi granted me a chance. She reassured me that I would be allowed to climax in our upcoming session. It solidified my belief that I am truly Mistress Lexi's slave now.
Day 22
Spoiler: show
Whenever I find myself with idle thoughts today, my mind drifts towards the orgasm that Mistress Lexi has graciously permitted me to have tomorrow. It's a special occasion because she selflessly sacrificed her own pleasure for my sake. This will be the first time she has given me explicit instructions to reach climax. I have been waiting for over 22 days without release, which is longer than my usual routine of one or two orgasms per week. The anticipation has built up over these three weeks, and I long for that long-awaited moment.
Day 23
Spoiler: show
Today's session was like a wild roller coaster ride, filled with mixed emotions that have left me feeling both happy and sad. I'm still trying to make sense of it all.

When I arrived, Mistress Lexi shared with me that she had orgasmed yesterday. It wasn't her choice, though. Goddess had called her and, along with her own slaves, attempted to make Mistress Lexi climax. They tied her up, teased her, and played with her, but she managed to resist their efforts because of me.

However, Goddess issued an order for Mistress Lexi to orgasm. Despite her objections, Goddess threatened to use a sybian on her until she cum if she didn't comply. Feeling trapped, Mistress Lexi reluctantly orgasmed against her will, and it made her feel guilty on my behalf. I sensed that Goddess took pleasure in seeing Mistress Lexi compelled to climax against her wishes.

It became clear to me that Goddess had deceived us regarding my own orgasm. It seems she planned for Mistress Lexi to reach orgasm every time she held herself back for nearly a week. Even though Goddess wasn't my true Mistress, she seemed to have control over my own pleasure, which Mistress Lexi had previously held.

Despite everything, Mistress Lexi still managed to tease and have fun during our session. I am willing to do whatever she desires and even bring her to orgasm again. Mistress Lexi expressed how fortunate she feels to have me, but the truth is, I consider myself incredibly lucky to have her as my Mistress.

During the session, Mistress Lexi asked me five questions. For each incorrect answer, I would have had to insert a finger into my ass while my cock remained locked. I dislike that sort of stimulation, but luckily I answered all the questions correctly and avoided that discomfort.

Mistress Lexi allowed me to unlock the cage, and I knelt patiently as she changed. While waiting, my mind wandered, and I imagined how Mistress Lexi was bound, teased, and played with by others while she resisted orgasming because of me. These thoughts kept me aroused and eager for what was to come.

As I began stroking, Mistress Lexi instructed me to attach the nipple clamps as usual. This time, she also had me tie up my balls with a shoelace. I wasn't sure if I enjoyed it or not—it felt peculiar. It was a form of torment, but it wasn't as terrible as I expected. She then commanded me to rip off the clamps and slap my balls, leading me to edge for an extended period. These actions were intended to arouse Mistress Lexi and possibly make her climax. Unfortunately, she was unable to orgasm this time.

After Mistress Lexi realized she couldn't reach orgasm, she asked if I wanted to cum. I expressed my reluctance for her to disobey Goddess. She explained that her original plan was to let me orgasm after enduring two long weeks of denial, and then she would experience an intense orgasm herself by watching me. However, since I couldn't climax, neither could she.

Mistress Lexi shared that she recognized my submissive nature from the moment she saw me, and that's why she chose me as her slave.

Mistress Lexi is both a Mistress to me and a slave to Goddess. She made the courageous decision to be a Mistress rather than a slave. She chose to allow me to cum now, following her own desires rather than solely obeying Goddess. I admire her bravery and strong willpower in defying her own Mistress. I love her even more for what she has done for me.

She ordered me to stroke until I reached orgasm. She wanted to give me my first proper release since becoming her slave. I felt conflicted about her decision because I knew it would anger Goddess. I didn't want Goddess to punish Mistress Lexi. However, Mistress Lexi remained steadfast in her resolve. As a slave, my only option was to obediently follow her instructions without hesitation. And so, I continued stroking until I climaxed.

In that moment, Mistress Lexi hesitated before giving the final order for me to cum, but she eventually did, and we experienced our orgasms together. It was the most incredible release I've ever felt, accompanied by a whirlwind of emotions.

Following our orgasms, Mistress Lexi instructed me to take a shower to clean up and then lock my cage again. However, when I returned from the shower, Mistress Lexi was nowhere to be found. She had disappeared from the house. I ventured outside and came face to face with Goddess. A sense of dread washed over me.

Mistress Lexi had been taken to Goddess's darkest dungeon, where she would undoubtedly face severe punishment for her actions. Goddess declared that the relationship between Mistress Lexi and me was over. Mistress Lexi was no longer my Mistress.

Goddess explained that she had planned to deny me for months through Mistress Lexi, but she never expected Mistress Lexi to disobey her because of me. Goddess taunted me with the key to my chastity device, claiming ownership over me. She wanted me to become her slave willingly. But after witnessing what she had done to Mistress Lexi, how could I ever willingly submit to her?

In response to my defiance, Goddess revealed a wicked smile. She informed me that if I refused to become her slave, there would be no possibility of me ever climaxing again. She held considerable power and influence, and she made it clear that there was no one in the country who could help me with the chastity device. Additionally, she warned that I couldn't leave the country without her permission, as she had connections in the immigration office.

She said that I could forget my cock and get orgasm by fucking my own ass. Alternatively, I could teach myself how to pick the lock, a process that she claimed would take around five years. However, if I chose that path, she promised to mistreat Mistress Lexi as a form of retaliation.

Given the circumstances, it seems that agreeing to become Goddess's slave is the only real option I have. It's the only way I can experience release again. And, perhaps more importantly, if I choose otherwise, Goddess will subject Mistress Lexi to further mistreatment. One positive aspect of becoming Goddess's slave is the opportunity to interact with her other slaves, including Mistress Lexi.

In the end, there was no choice for me. Goddess emerged victorious, and I was compelled to agree to become her slave. She made me say out loud: "I am Goddess Brookes’ property. The Goddess is to do with me as The Goddess likes. I will not forsake The Goddess. I will not cum without The Goddess permission. I will always refer to The Goddess as The Goddess. I will forsake my pleasure for The Goddess. I am The Goddess’s forever."

I had to bow down before her and say, "Hail the Goddess." Then, to seal my submission, I kissed the ground. From this point forward, Goddess has complete ownership over me.
Day 24 (Chastity 3.5: Quizmiss Hailey)
Spoiler: show
I still can't fully understand everything that happened yesterday, and I need more time to process it all. However, Goddess didn't give me that time. She called me this morning and ordered me to go to Miss Hailey's place.

When I arrived and saw Miss Hailey, she informed me that Goddess had given her the authority to tease me and decide my fate for the day, whether it would be orgasm, ruined orgasm, or denial.

Miss Hailey proceeded to ask me 30 questions. For each correct answer, I earned some points, and for each wrong answer, I lost some points. The points I accumulated determined the number of seconds I could stroke my cock as fast as possible before I had to stop. I had to stroke as quickly as I could and stop when the time was up. If I reached orgasm within the allotted time, I would be allowed to cum. If I couldn't cum, I would be denied. The most challenging scenario was if I was on the verge of orgasm when the time was up—I would have to stop and ruin the orgasm.

I managed to earn 24 points, but before I even started, my cock was completely soft. There was no way I could reach orgasm within 24 seconds. So, sadly, I was denied today.

I'm really amazed that Goddess actually kept her promise and gave me a chance to have an orgasm that soon.
Day 25 (Chastity 3: Chastity for the Goddess)
Spoiler: show
Goddess Brooke really doesn't give me any breathing space. She called and told me to see her today. I didn't really want to see her, so I arrived at her place just in time. Goddess said I was late by twenty seconds, but I'm sure I pressed the bell at the door exactly when she told me. I know it would only hurt me if I argue with her, so I just let it go. She also mentioned that I should be prepared for our sessions early and kneel, waiting for 5 minutes before they start. I think it's best to follow that rule, as I don't know what the punishment would be if I didn't.

I have to admit, Goddess is very beautiful. Her face, her body, her legs, everything is perfect. Sometimes, I wonder why such a beautiful woman can be so evil.

She made me repeat her new rules out loud:
1. I will NEVER cum without the Goddess’s permission.
2. I will always refer to the Goddess as the Goddess, or Goddess Brooke.
3. I will always wear a collar while subbing for the Goddess or any of her slaves.
4. I will always be in chastity when not performing for my Mistress.
5. I will never hesitate to obey the Goddess. I will never disobey the Goddess.
6. Never edge without the Goddess' or my Mistress for the days permission. If I do, stop stroking, spank my balls 20 times, then continue.
7. If I accidentally start to cum, ruin myself. I should never have to do this, but it needs to be said. Then wait 2 days and try the section again.
8a. If it is warm at night, I am to sleep naked.
8b. If it is cold at night, I am to sleep in at least a girly panties and bra.
9. Before every session, write "The Goddess' property" above my chastity belt in pen.
10. Every night, before I go to bed, and every day as soon as I wake up, I am to squeeze my balls through my little chastity device and repeat "I am the Goddess' property" 5 times.

There was a footnote about cum permission. Some of her slaves may try to make me cum without the Goddess's permission, and if I do cum, I will be punished because only the Goddess can give permission for me to orgasm.

After I read the rules to Goddess again, she unlocked me and commanded me to stroke. She told me more about herself. Goddess's full name is AshyInn Brooke. She has at least 20 slaves and she has made her slaves dominate others.

When Goddess forced me to stroke and say "I am Goddess Brooke's slut" in front of her, I felt so humiliated and I truly felt like her slut. I don’t like it, but it is who I am now.

At one point, Goddess suddenly ordered me to spank my balls hard. I knew it was a trick, so I didn't hesitate to hit my balls. I was quite sure she would punish me if I didn't do it immediately.

Goddess will send four of her slaves to dominate me: Miss Hailey loves edging, Xiu enjoys sissy play, Riley is into chastity, and Penny is a sadist. Both the four Mistresses and I have no choice but to do what Goddess orders. However, I do have the choice to decide the order in which I'll see them.

It has always been my fantasy to dress up like a girl, but I was too scared to do it on my own. So, I chose Xiu. I need to bring nipple clamps, panties, a bra, stockings, and a butt plug to the next session with Xiu. I will see her in two days.

Today, Goddess only allowed me to stroke, not even an edge. I really need more teasing than that whenever my cock has a chance to escape from the cage. Goddess probably knows that will make me suffer. She has so much experience in domination, I don't know if I can resist her like Mistress Lexi did. But that rebellious thought still lingers in my mind. It reminds me of Mistress Lexi.
Day 26
Spoiler: show
According to Goddess's rules, I had to sleep naked last night. I've slept naked before, but not often. Sleeping naked with a chastity cage felt even more humiliating and vulnerable. At first, I even tried to cover the cage with my hands. To make it worse, when I closed my eyes, I felt like Goddess was watching me, laughing at me, and humiliating me.

Saying the mantra "I am the Goddess' property" before sleeping was something I didn't want to do. I opened my mouth, but I couldn't bring myself to speak the words. Eventually, I did it along with the ball squeezing. Following these two rules made me feel a little bit controlled by Goddess, just after the first night.

That feeling is similar to when I first met Mistress Lexi. She forced me to do things I didn't want to do, but I did them because I believed there was no other way. I've experienced this before. Why did I have to sleep naked or say the mantra if Goddess has no way of knowing if I've done it or not? I think I'm in the same situation—I did it because it's who I am. I always follow others but rarely make my own decisions. This has already been proven in my relationship with Mistress Lexi.

When I was with Mistress Lexi, I chose to follow her commands and hoped for the best. And it worked! Mistress Lexi and I finally had a wonderful relationship, even if Goddess played a part in it. But I still cherish the moments I had as Mistress Lexi's slave. And I will do the same this time, hoping for the best.

Interestingly, I felt good when I prepared the panties, bra, and stockings for the next session. I used to be too scared to own any of them, but this time, I have no choice but to get them. That mindset compelled me to acquire them all. It's a bit exciting. And when I tried them on for testing, it felt really good and my cock grew inside the cage. I can't believe I'm saying this, but I think I love it.

I'm eagerly looking forward to seeing Xiu tomorrow.
Day 27
Spoiler: show
I must say Xiu is exactly my type. She's Asian, with black hair and a nice body shape. And she dressed exactly the way I like, wearing a purple corset and black stockings. Maybe that's one of the reasons I chose Xiu first when I saw her picture.

When I arrived at Xiu's room, she didn't know who I was. I tried to explain that Goddess sent me to her for teasing. Finally, she understood and laughed, telling me that she's a lesbian and doesn't enjoy playing with men.

Then, Xiu received a text from Goddess with just one word: "Surprise." She realized it was a punishment for her because she messed up in her last session. She doesn't like playing with men, so Goddess letting her tease me is actually a punishment for her. When Goddess punishes her slaves, it's not just physical punishment like hitting or tying them up. She knows her slaves and forces them to do things they hate. She truly knows how to punish her slaves mentally. I'm now worried about Mistress Lexi even more. I hope Goddess doesn't break her down mentally, as that would be the worst for both of us.

Xiu instructed me to put on the panties, bra, and stockings. I still enjoyed dressing up like this. However, Xiu wasn't interested in it. She just wanted to finish her task of teasing me as quickly as possible.

Before we started, she suddenly kicked my balls, causing me to fall to the floor in pain. She did it just for releasing some frustration from this unwanted situation.

Since Xiu didn't have the key to my chastity cage, there was no luck in unlocking it. She just used clamps to hurt me and forced me to fuck myself with the butt plug. I really disliked the butt plug and never thought I would come to like it.

Xiu truly despised playing with men. She simply recorded an audio of the teasing and told me to play it to tease myself again. Then, she left me alone and went to another room.

I played the audio and repeated the nipple clamp torture and butt plug insertion again. The entire process was completely unenjoyable.

When I finished, I found her in the other room, and that was the end of the session. It felt really bad at that point. Just like yesterday, I had imagined how fun this session would be and expected many interesting things to happen. But there was nothing, just me forcing the butt plug into my ass, which I absolutely hated. Maybe Goddess already knew that Xiu would treat me this way, and it could be another one of her tricks, making me frustrated once again.

Now I had to choose the next slave of Goddess. I had already made up my mind yesterday, and I chose Riley, who enjoys chastity. In the next session, I probably won't unlock my cage. But if I already know that, I can manage it. It's Goddess's tricks that I'm afraid of. But I cannot do anything about it.

The next session is in two days, and Riley wants me to bring the following items: a vibrating butt plug, lube, a gag, a blindfold, two pieces of rope to tie my legs, handcuffs, my collar, four clothespins, and a pair of clover clamps connected by a chain.
Day 28
Spoiler: show
I have to say "I am the Goddess's property" five times every day. Yes, I must do whatever Goddess tells me to do, she has control over me now, I cannot deny it. But I am not an object owned by the Goddess, I am not. I am still a man, maybe a slave now, but I am not an object.

However, when I look down at my caged thing, the Goddess holds the key to that special lock. I will never cum without the Goddess’s permission. I cannot touch it, even though I am really needy after the previous sessions with the Goddess and her slaves. Yesterday, before Xiu's session, I had to write "The Goddess's property" above my chastity belt. After I finished writing, I knelt on the floor and took a moment to look at my writing and my caged cock. In that moment, I realized that my cock truly belongs to the Goddess. I have no control over it anymore, I don't own it anymore. And even now, when I look down, I still feel the same way—it is the Goddess's property now.
Day 29
Spoiler: show
Mistress Riley surprised me with her black fishnet lingerie, it was different from what I expected based on the picture shown by Goddess. She seemed more conservative there. It was like she transformed into a whole new person.

I already knew I would be tied up today, as I guessed from the items she asked me to bring. My legs were securely bound to a chair, a gag was placed in my mouth, and I listened to an erotic audio. Meanwhile, a vibrating butt plug was inserted in my ass, clothespins pinched my lips and ears, nipple clamps tightened, a blindfold covered my eyes, and my hands were handcuffed to my collar.

The twist came when Mistress Riley instructed me to count to 12 minutes in that challenging situation, with only a one-minute window for accuracy. I began counting, saying "one thousand and one, one thousand and two..."

But I failed. I stopped at 15 minutes. The distractions were too many to handle. The erotic audio made me incredibly aroused, and I could feel precum forming. I lost count several times, my thoughts wandering to my cock. The vibrating butt plug caused discomfort, and the pain from the clothespins added to the challenge.

I have to return to Mistress Riley tomorrow for the same session. She informed me that it will only come to an end when I can count to 12 minutes correctly. I will try to practice today, hoping it will improve my chances. But deep down, I know I also need some luck to pass this test.
Day 30
Spoiler: show
I did it! I honestly don't know how, but I managed to succeed. Even though I practiced a bit yesterday, I could never count the time correctly. I always went over 12 minutes, so I tried stopping around 11 minutes. I didn't have much confidence that I could do it today, so I thought I would have to attempt it 3 or 4 times.

It just dawned on me that Mistress Riley might have been watching me the whole time. Of course she would, but I hadn't really thought about it until now. It feels so embarrassing to think that Mistress Riley saw me tied up, completely helpless and vulnerable, struggling throughout the ordeal. What I disliked the most was the feeling of my own warm saliva dripping onto my chest. It made me feel like a slut, craving any sort of sexual encounter. I really don't like it when people see me in that way.

When I was bound there, my sole focus was on counting the time. But now, as I reflect, I realize the feeling of helplessness and surrendering my entire body to Mistress's mercy. I actually enjoy that sensation.

After I released my restraints, Mistress Riley made me finish listening to the erotic audio and instructed me to make myself aroused by playing with my nipples, balls, or finding any way I could pleasure my caged cock. There were about 10 minutes left, and during that time, I was in a frenzy. I tried so hard to make myself as horny as possible while listening. It was the first opportunity I had since my last orgasm with Mistress Lexi to indulge in such intense self-teasing. I couldn't control my hands; my body just craved more touch.

My chastity cage was already filled with my saliva and precum before that, and during those 10 minutes, the precum dripped uncontrollably down my thigh to the floor. It felt pleasurable in that moment. Of course, it became even more horny and desperate when I had to stop. Then Mistress Riley shared more of her dominant stories, which only intensified my longing.

Lastly, I chose Penny for the next session in 2 days. I need to bring 20 clothes pegs, toothpaste, a ruler, and a shoelace. Yes, it's going to be painful. I really don't like experiencing pain. But I am Goddess’s slave now, I don’t have a choice.
Continue: My journal of Chastity Series (Day 31 - Day 37)

Continue: My journal of Chastity Series (Day 200 - Day 211)

Continue: My journal of Chastity Series (Day 240 - Say 250)

Continue: My journal of Chastity Series (Day 280 - Day 286)

Continue: My journal of Chastity Series (Day 287 - Day 298) (End)
Last edited by captivewhim on Mon Sep 11, 2023 6:54 am, edited 23 times in total.
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Shattered
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Re: My journal of Chastity Series (Day 24)

Post by Shattered »

This is a very entertaining way to see my tease be experienced, I enjoyed catching up on your progress :-) I'll be sure to check in from time to time.

Is this your first time with the series?
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Re: My journal of Chastity Series (Day 25)

Post by captivewhim »

Hi Shattered,

It is great you like it. And thank you for your teases. Playing along has been an immensely enjoyable experience.

Yes. It is my first time with the series. It always bring joy to speculate on the possibilities of what lies ahead :-D
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