My journal of Chastity Series (Day 240 - Day 250)

Great writing can be the sexiest thing in the world. Give it a shot and describe the most erotic experiences - real or imaginary - right here.
Post Reply
captivewhim
Explorer
Explorer
Posts: 17
Joined: Sat May 27, 2023 2:59 am

My journal of Chastity Series (Day 240 - Day 250)

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)

Episode 5 of the Chastity series concludes on Day 250.

Day 240 (Chastity 5: A webtease for Hailey)
Spoiler: show
We had conquered the Goddess a month ago. I am now Miss Hailey's full-time slave. It's working fine. Miss Hailey and I are now friends; we have dated on occasion, watching movies or going out to dinner. Of course, Miss Hailey makes all of my decisions, but she usually chooses the activity that I enjoy. She is always pleasant to me, as she was previously.

I no longer needed to wear the chastity cage all the time. Without the cage, life is a lot easier.

We have a lot of rules and a lot of fun sessions. Miss Hailey loves to edge me, and I'm sure she's commanded me to edge hundreds of times. But I enjoy obeying her commands.

Miss Hailey told me to take a week off from work, beginning tomorrow. And I know she had something planned for a while. She instructed me to come to her place tomorrow. I believe she will have something to surprise me with.
Day 241
Spoiler: show
When I got at Miss Hailey's apartment today, she informed me that she intended to let me cum. But first, I had to lock my cage, it appeared like I would be wearing the chastity cage for a week.

She discovered Milovana's website in my browser history, and she adores the concept of desperate sluts begging for the attention of sexy Mistresses. She did make a tease there, and I will be a beta tester. She will watch me play the tease to assess if it is suitable for public distribution.

Miss Hailey let me roll a 20-sided die, and I rolled a 17. And when she said I may go, I was curious what would happen if I rolled a 1 or a 20.

I began playing the "Teased by Sin" web tease. Miss Hailey was constantly observing me. When I played a web tease in Milovana, it was the first time someone was watching. It felt odd, and I was humiliated. And Miss Hailey would occasionally force me to make a decision she proposed. In the same way as a mistress exerting control over her slave.

The teaser mentioned a Sin Mansion. A magic forced me to become naked and caged as soon as I entered the mansion. Miss Hailey was the one who took off my clothes and locked my cage. Miss Hailey casted the spell. Lol.

Yexahil, a woman, appeared. She was my guardian angel, guiding me. She said there are seven deadly Sins. Lust. Gluttony. Greed. Sloth. Wrath. Envy. Pride. Only by conquering all Sins will I be able to be free.

Before I accepted the challenge, Yexahil inquired what was my class: warrior, wizard, rogue, or pervert. I chose pervert for fun, and it is actually the best suit for me.

And she gave me some ground rules:
1. Do not cum.
2. Do not hesitate to obey any commands that are given to me.
3. If I am unable to overcome a Sin, I can try again later.

Yexahil also warned me that this is a house of illusions, and that perception is everything. And I must demonstrate my virtue in order to overcome each Sin.

Normal tease players may not need to fight all of the Sins, and they may simply conclude the tease by casting the spell, risking to have a ruined orgasm. But Miss Hailey said I couldn't; I had to defect all the Sins. As a beta tester, it just made sense for me to go through all of the Sins.

I may choose which Sin to eliminate first. But I had no preference for any of them; I simply chose from the order listed. So, the first challenge, Lust.

The Lust Sin informed me that there are two ways for me to demonstrate my worth. The lengthy and easy route, or the short and difficult route.

Miss Hailey compelled me to take the long route of chastity for 24 hours. It's not that easy for me, because my precum was already dropped on the floor, and my cock was expected to receive some care. But I had to wait another day in chastity.
Day 242
Spoiler: show
I could finally let my cock out of the cage after another long day of chastity. Luxuria was the name of the Sin. She gave me the instruction to stroke and edge.

She mentioned a lot about Lust. It feels amazing to cum, but holding onto my Lust feels even better. The edge was too strong to bear, yet as soon as I let go, that horniness begged for more. My Lust tears me between two kind of torture, and I want both.

She then ordered me to edge as many as I could, to my highest limits, and then we'd call it a day. I couldn't count it, but I'm quite sure I edged more than ten times before stopping, when I knew I was almost to cum. It was my breaking point.

But I was duped. It was only the start of the tease. Luxuria simply deceived me into pushing myself to my limit and then forcing me to breach it. She told me to hold an edge right away. What a shock. What a torment. She claimed that was on the verge of oblivion. I believe that was true; I couldn't think of anything at that moment. She pushed my Lust even further away from me by many more edges.

Finally, the edging came to an end, and Luxuria affirmed that I am in control of my Lust. And she said the word "Vestra" to me.

When I finished the tease, I realized Miss Hailey had been watching me the entire time. There are so many agonizing edges that I was completely absorbed in the teasing and forgot about Miss Hailey.

Miss Hailey stated the regular players might keep teasing, but she told me to perform the next Sin tomorrow. I'm sure the Lust will torment me for an entire day.
Day 243
Spoiler: show
For the tease, I played the Sin of Gluttony. Gluttony is defined as excessive intake of food or drink, and today I would be excessively consumed by edging.

I came across a succubus. She made me stroke once every 10 seconds, but I didn't allow to edge. It didn't feel like much at first, but after some time, I find myself wanting to disobey her and stroke more. Then I had to stroke twice every ten seconds. And she began to allow me to stroke third times every 10 seconds. When I got to 10 strokes every 10 seconds, I got horny and wanted to edge. I couldn't believe I was so close while only stroking once every second. That buildup was insane.

I encountered two lovely women in the next room after I passed the succubus. They were known as Gula. This exercise was straightforward; all I had to do was hold an edge for an extended period of time. I'm not sure how long, but my tears were streaming down my cheeks, and I begged them to let me stop again and again. And seeing the two beautiful women making out drove me insane; I had to stop looking at them. It was simply too much for me.

When I was finally able to stop, a Gula said that if I was her slave, she would ruin my orgasm at that time and force him to stroke for 10 more minutes of post-orgasm torment, or she would keep me stroking till I ruined again and do it all over again. I can see Goddess would try that to me; I only hope Miss Hailey never becomes so cruel.

They simply said "Ligat" and let me go.
Day 244
Spoiler: show
Miss Hailey informed me that Qingfu Xue wishes to meet with us tomorrow. Miss Hailey enticed her to fight Goddess by promising to be her slave for one day. Qingfu Xue enjoys control; I had a 12-hour session with her to completely control me. I know Miss Hailey doesn't like it, but it's the price we had to pay for the lovely life we now have.

We'd still be playing the online tease today. Greed was my choice. It was an odd one. I had to go to freerice.com and play their game to contribute 200 grains of rice. It was not bad to help others even it was just a very little.

I then met another woman who introduced herself as Avaritia. She instructed me to erase some of my pornographic videos. No, I couldn't do that, but Miss Hailey was watching me, so I had to act. So I threw them in the recycle bin and will retrieve them later.

But Avaritia had already thought of it; she made me empty the recycle bin as well. I really didn't want to do it, but I decided to defraud her. Miss Hailey, however, intervened and forced me to remove them all. It could show that I am really a greedy man.

I had the word "Ego" after the session ended. There was not even a touch today, which makes me even more aroused. But we'll meet Qingfu Xue tomorrow, and I'm sure she'll take charge of my horniness.
Day 245
Spoiler: show
Miss Hailey was not ready to leave when I arrived at her house. She preferred that I go first and make an excuse for her.

When I arrived to Qingfu Xue's residence, a gorgeous woman was waiting for me outside. After staring at me for a bit, she let me in. And when I got to Qingfu Xue's room, she was just as charming as she had been the previous time. I informed her that Miss Hailey's heel was broken and that she will be there shortly. She didn't seem to believe it and inquired if I was lying to her. Of course, I insisted on the truth in order to protect Miss Hailey.

Miss Hailey soon arrived. Miss Hailey addressed her as Xue but not Qingfu Xue, and Qingfu Xue had punished her for this. Qingfu Xue told Miss Hailey to open my cage and handed her the key. She called Miss Hailey a slave and me a nuli, which I believe also means slave in Chinese.

She commanded Miss Hailey to pinch her nipples and ordered me to get hard. She knew Miss Hailey didn't like today's session, but she ordered her to smile for the whole session.

She then told me to stroke quickly for her, not Miss Hailey. She pointed to Miss Hailey and stated she was her slave, her plaything. And I wouldn't see her the same way after the session was over. That happened to Lexi, so it was a little familiar.

She instructed me to stroke slowly and to keep an eye on Miss Hailey as she stripped. Miss Hailey felt anxious but she was compelled to smile over it. Miss Hailey said something impolite, and Qingfu Xue retaliated by instructing me to spank my balls. Because of me, Miss Hailey was obliged to apologize to her.

Once Miss Hailey was naked, I had to edge and hold it. Qingfu Xue said Miss Hailey claimed to be my Miss at the time, but now Qingfu Xue was the one controlling my cock, and Miss Hailey was completely naked, vulnerable, and powerless. She claimed Miss Hailey was born to be a slave and that she will beg to be hers soon.

She knew Miss Hailey didn't want me to cum, so she threatened to make me cum if Miss Hailey disobeyed her. Miss Hailey was powerless to speak up. She was going to use me to punish Miss Hailey, and she was also going to use Miss Hailey to punish me, so I had to obey her.

Qingfu Xue wanted to play only with Miss Hailey, so she locked my cock again and sent me to another room. I noticed the lovely lady at the entrance gate was in the room. Xia is her name. Qingfu Xue had sent me there to proofread her writing. But I'm not a professional, so I just guessed it. It seemed I really found some errors in her article.

Before we continued, we heard a tremendous noise, which appeared to be Qingfu Xue's orgasm. Xia was ashamed and sent me out of her room.

When I returned to Qingfu Xue's room, she was fatigued; it seemed she spent a lot of her fantasies with Miss Hailey. And her next fantasy was about me dominating Miss Hailey, in another room. But she would keep an eye on us through webcam. I couldn't touch Miss Hailey, but I could stroke my cock, so she unlocked me.

When I entered Miss Hailey's room, she greeted me as Master. This was a situation similar to what happened with Lexi. But Miss Hailey wasn't Lexi; they're so dissimilar that I assumed everything would be fine this time.

Miss Hailey was completely immersed in her act. I didn't know if Qingfu Xue pushed her or if she wanted to be a slave. I told her to kneel, and she did so. I then told her to strip for me, and she did. But right in the middle, we heard Qingfu Xue's voice telling us to switch roles. I'd be Miss Hailey's slave once more. This order confused both of us.

Miss Hailey retaliated for what I did to her by ordering me to edge for her and spanking my balls till my cock went soft.

We heard Qingfu Xue order another swap. Miss Hailey appeared concerned, as she should. It was my time now. I repeatedly told her to spank her pussy. It liked a game for Miss Hailey and me. It fascinated to me.

But Qingfu Xue ordered us to switch roles again. Miss Hailey instructed me to stroke. And Qingfu Xue told me to stop and she would take control of both of us. She'd ordered us to edge as quickly as possible, with the first one to edge might ask for permission to cum. Miss Hailey didn't want me to orgasm, so I just slowed down a little to let her win, and she did. Miss Hailey, on the other hand, surprised Qingfu Xue and me by claiming she didn't want to cum.

Qingfu Xue was perplexed by Miss Hailey's decision. Qingfu Xue told Miss Hailey to go to her room and leave me alone. My cage was unlocked, and no one was there. I generally can resist the urge to stroke, but for some reason, I decided to stroke a little to relieve some pressure.

Xia was standing near the entrance when she noticed me stroking. She walked in and began talking to me. She said she was vanilla, but Miss Hailey, me, and Qingfu Xue did things that caught her attention. She wanted to try it on me, so she requested me to stroke my cock, which I did. Then she requested me to stop, and I obeyed. She seemed joyful as well as worried about my obedience. She didn't know what to do and just left.

Miss Hailey came in after a while and told me to go to Qingfu Xue's room. Miss Hailey was fatigued; it seems like Qingfu Xue had put her through quite the ordeal.

Qingfu Xue ordered that I strip naked and put on the clover clamps. And I had to cup the clover clamp chain beneath my balls, which stung and drove me to arc forward. Then she told me to stroke, and every stroke hurt my nipples in that position.

She forced me to edge and get soft repeatedly, I remember that torture game. After I did it for a few times, she urged me to get soft and lock up my cock. This was challenging since I had to wait a long time for my cock to become soft enough to lock in the cage.

She explained that her objective was to break Miss Hailey and make her her slave. Anyway, she let me out of the cage and made me hold an edge once more. She asked if I wanted to cum today, right in front of Miss Hailey. I still can't believe I said yes to her. I knew I was betraying Miss Hailey by saying that, but it was too much today, and there had been a lot of tease in the previous several days. And after the excruciating edge and soft game, I was crazy for orgasm, I became weak again, and I truly want to cum whatever it takes.

Qingfu Xue appeared to have already planned to compel me cum in front of Miss Hailey's face as she was ruining an orgasm. It could really break Miss Hailey like that.

She finally made me stop and told me to re-lock my cock. My cock takes a very long time to soften and lock, and I almost come when I put my cock inside the cage, my cock was too sensitive at the moment. She sent me on my way, saying she needed to see Miss Hailey again.

As I was about to leave the room, Xia stopped me and asked me to see her outside. I spotted her outdoors, and she appeared nervous. She stated she wanted to understand more about the strange things she heard today and hoped I could assist her. She showed me a key, the key to my chastity cage. She believed that if she kept the key to my chastity cage, my penis would be hers. She told me I had to stay and wait for her. She quickly ran away.

Miss Hailey eventually found me. I informed her of the key. But she didn't seem concerned, and she was planning on utilizing it to get us out of there. She informed me that she had a spare key. She intended to let Xia dominate me for a while, she could use that to negotiate with Qingfu Xue to let us leave. After they talked. Qingfu Xue agreed to let us go; she claimed we'd have to return later, but our deal was only one day, so we'll see about that.

We went shopping together because we had some free time. We appeared to be an ordinary couple's outing, but Miss Hailey usually takes advantage of the occasion to tease me in public. And we both enjoy it.
Day 246
Spoiler: show
I stayed at Miss Hailey's house last night, and when I awoke, Miss Hailey was playing with my phone. Of course, she has the right to use my phone whenever she wants; she is now my dominant.

Xia texted me, telling me to come to her place today. I wanted to see her because I believed I could assist her in discovering herself. But Miss Hailey was upset because I wanted to sub for another Mistress, and Xia tried to steal me. However, she felt sorry for Xia and wanted to assist her in entering the world of dominance.

Miss Hailey is a wonderful person in my opinion. She eventually consented to let me visit her. I had to make sure Xia know that Miss Hailey is always in charge of me. And under no circumstances could I orgasm.

When I got at Xia's house, I caught sight of her. Her clothing was rather revealing, yet she was not naked. I mentioned Miss Hailey's web tease to her. She was intrigued by the concept. As a total newcomer, she had no idea what a ruined orgasm was. I told her, and she wanted to try it on me today. I had worries about that.

She asked to see me play the web tease, so I obliged. I couldn't believe I had to play the tease in front of another woman.

This time, I went with Sloth. The first segment consisted of a memory game. I'm always lousy with memory, so I have to go back to the beginning a lot when I can't remember stuff. Fortunately, there is no penalty for starting over.

I met Tristitia after the memory game. She made me rotate slowly for her examination. That bothered me, especially when I was wearing the cage. She told me to stand on one leg, do sit-ups, star jumps, and push-ups. Then she made me do it all over again while I was stroking. She then gave me the word "Conteram" after some additional physical workouts and stroking.

Xia decided to leave me without the ruined orgasm today since she believed that doing whatever she wanted was true control.

She told me to get soft and put my cock inside the cage, but just as I was about to use my lock, she pulled out a new lock and used it to lock my cock. She moved so fast that I didn't even have time for a response. She commanded me to call her Mistress from now on and to leave for now.

I returned to Miss Hailey and informed her what had happened. She was enraged. But after a little thought, she decided she wanted the tease to end within a week. So she asked me to keep the web tease going with Mistress Xia. She forbade me from having any orgasm, whether ruined or full. And she gave me permission to obey the tease to the letter. Does it have any significance? Is there another surprise in the tease?

Anyway, I texted Mistress Xia about it, and she liked it. So, I'll see her tomorrow.
Day 247
Spoiler: show
I went to Miss Hailey's apartment first. I liked Miss Hailey in her everyday outfits. It gave me the impression that we were more like a couple. She wondered if she could still refer to me as a slave now that she had lost control of my cock. She reminded me not to let Mistress Xia ruin my orgasm.

I arrived at Mistress Xia's house. She intended to take me away from Miss Hailey and eventually become her slave. I told her about the first time I met Lexi, what occurred with Brooke, and how I ended up with Miss Hailey. Right, Miss Hailey and I are going to refer to Goddess as Brooke now, although we sometimes forgot and still referred to her as Goddess.

We started the web tease, and I chose Wrath. A woman commanded me to kneel, I kept quiet and kneeled in front of her for quite long. I was well-trained to do it correctly. And she ordered me to tie myself up in the chair with a vibrating butt blug, a gag, a blindfold, and clover clamps. I was held captive for ten minutes while listening to erotic audio. It was only the beginning of today's teasing.

Mistress Xia informed me that she has orgasm just watching my bondage and will most likely tie me up again later.

After then, I met Ira. She told me to kneel, and she expected me to obey to her every command in a short amount of time. She needed me to unlock my cage in 30 seconds. In 20 seconds, I had to get hard. Squeeze and strike me in the balls. Stroking and edging in a short time. I'll get a Strike if I do them for too long. At the end of the session, I had to report to her how many Strikes I had.

If I didn't finish her requests in the allotted time, I had to restart some strokes and edges. She even ordered me to get soft in such a short time. It was quite challenging, and I had to repeat it several times to get through it.

At the end of the tease, She told me to stroke 100 times in 10 seconds. I failed and had to restart from beginning. I knew it was impossible the second time, so I cheated by simply clicking on the button. Oh crap, Ira caught me cheating and made me do it all over again! Finally, Ira let me go, putting an end to the tease. It was lucky for me, I actually could not hold it anymore. It seemed odd that she didn't inquire how many Strikes I had. I received 15 Strikes. She said the word "Ipse" to me.

But Mistress Xia was not finished with me. She forced me to edge and stroke for her. She asked if I wanted to be her slave and told me to hold an edge. I replied, "No." But she said nothing and just let me grasp the edge. And then she asked me again. No, I said from the bottom of my heart. And she simply ignored me, leaving me to keep the edge. She asked me again after awhile if I wanted to be her slave. What could I possibly do? It was Miss Hailey's instructions that I could not cum, and I was unable to hold that edge any longer. So I answered, "Yes."

Mistress Xia appeared pleased after compelling me to agree to be her slave. She then told me to go and waited for her message.

I returned to Miss Hailey's house. She was relieved that I did not have any ruined orgasm. Mistress Xia sent a message to her. When she read Mistress Xia's text message, she became enraged.

Anyway, Miss Hailey called Caprice to come to assist us. Caprice is actually a skilled locksmith; she might be able to open my cage. She examined it and attempted to open it, but she couldn't because she needed a specific tool. She can obtain the tool, but it may take some time. But, before she did anything, she wanted to know if I truly wanted to be Miss Hailey's slave. And the answer is unequivocally yes; I adored being Miss Hailey's slave.

Caprice left after a brief conversation with Miss Hailey. Miss Hailey informed me that we didn't need to contact Mistress Xia for the time being because we could free the cage soon. If Mistress Xia calls, I will keep playing the web tease; otherwise, we shall leave her alone.

Miss Hailey revealed that the trapped damsel is her. And I can have the first sex with Miss Hailey once I free the damsel in the web tease. Miss Hailey had planned for it from the beginning. I can't believe Miss Hailey has done so much for that. I'm simply overjoyed.

We might not doing the web tease, but Miss Hailey still wants to see me tomorrow.
Day 248
Spoiler: show
When I arrived at Miss Hailey's house, she was dressed for work. With her attractive clothes, I didn't think her coworkers could concentrate on their work. Miss Hailey didn't sleep last night because she was concerned about my situation; what if Caprice is unable to unlock my cage? And she denies herself for the time being, and she will not cum until I do. Lexi had done that to me before, but that's another story. And Miss Hailey and I had a closer relationship than Lexi. I can only say that I was really fortunate to meet these two women.

Miss Hailey needs to go to her office, so we'll take today off.

I was still thinking that day with Qingfu Xue. She broke me and had me beg to cum in front of Miss Hailey. She had already planned to let me cum in front of Miss Hailey while she was ruining her orgasm. If it hadn't been Mistress Xia, she might have already broken Miss Hailey's soul with that. Especially if Miss Hailey is aware of my request for cum. I'm ashamed to tell Miss Hailey about my pleading. I don't want to upset her, but I don't want to lie to her. Maybe I will tell her when everything passed.
Day 249
Spoiler: show
Last night, I was with Miss Hailey. I awoke in the morning to a text message from Mistress Xia. She wants me to meet with her today.

I first contacted Caprice to see what she got. She said she could break the lock if I wanted Miss Hailey, or she could pretend she couldn't if I preferred Mistress Xia. I'm not sure why she was so persistent about it, Miss Hailey will always be my answer. But she wants me to think about it and get back to her tonight.

Then I arrived to Mistress Xia's residence. She dressed up like D.va. And she requested that I call D.va in today's session. Today we were playing Sin of Envy.

I saw a woman who was bound and gagged. She felt compelled to say something. And a voice in my head instructed me to relax and do nothing. And I just stood there admiring her. I just laughed at her, as the voice instructed. And then I noticed another woman, who was gorgeous. Invidia was her name.

First, she mentioned her exquisite, perfect body. I wish I could be her.

Then she claimed to know every little thing about Miss Hailey. I was envious. I wanted to know everything about Miss Hailey.

She can cum anytime she wants, but my cock will never be free. I was envious.

She then showed me a video of Lexi doing blowjobs with several men, all of whom orgasmed in her month or to her face. I wanted my cock in her month as well; I envied those men.

She finally let me go and give the word "Probavi" to me.

Because Mistress Xia had a meeting today, she just told me to leave.

Caprice contacted me when I was returning to Miss Hailey's house. She asked me to select between Miss Hailey and Mistress Xia once more. I told her one more that I adored Miss Hailey.

Caprice had already come when I returned to Miss Hailey. Caprice utilized the new gadget to open my cage, and she was successful. Miss Hailey instantly replaced the lock on my cage. She claimed to have felt love, lost it, and found it again. She expressed it in such a cute way. I love her.

Miss Hailey was overjoyed and asked me to perform the final Sin of her tease. So I chose Pride.

When a woman inquired if I was doing this tease for myself or for someone else, I said that I was doing it for Miss Hailey. She then instructed me to unlock the cage and slowly stroke my cock. She told me to stare at my cock and imagined the damsel in trouble, Miss Hailey's face in my head. She said that the strokes were not for my pleasure, but to free the damsel.

She let me stroke in many different ways, and she emphasised that they were all for the damsel.

I then met Superbia. She was the one who attempted to take away my Pride. She made me stroke for every word she spoke so I would pay attention to every word she said. Then she made me say certain words aloud for each stroke till I edge, "useless", "pathetic", and "miserable". With those statements, she attempted to belittle me.

She made me put on panties, a bra, stockings, and high heels. I also had to put the nipple clamps on. She told me to keep saying "sissy" till I edged.

She instructed me to spit on my cock, stomach, nipples, and face. Then I had to take a small sip of water and slowly dribble it all over my body. Another load of water, this time more of it, and let it dribble all the way down my body. I had to put on a ball gag after another load of water. My saliva and water just poured out of my month uncontrollably after that. I had to edge to the word "drool" and then hold that edge with the word "sissy" for each stroke.

She then forced me to write words that degraded me on my body using a pen.

Finally, I had to slowly pull the water from the top of my head, allowing the water to wash away any remaining Pride. And I continue to say the word "pathetic" over and over again while holding an edge. She let me see myself at the time, a sissy with pen marks all over my body, wet, gagged, and drooling, shouting how pathetic I was while edging. This is my actual self.

Superbia seemed satisfactory with who I am now and let me go. She gave the word "Libera" to me and said I was now ready for Miss Hailey. And I suddenly realized Miss Hailey had been watching me the entire time, and I was still ashamed to be looking like that in front of her. It revealed how weak and pitiful I am.

Miss Hailey advised me to phone Xia and tell her I was no longer her slave. I informed her that we had brought in a locksmith to crack the chastity cage. Xia was upset, but I assumed she would be alright.

The final portion of the tease will be done tomorrow.
Day 250
Spoiler: show
I was looking forward to the Miss Hailey tease finale. I began to cast the magic using the words I had gathered from all the Sins, and I saved the damsel! She promised to let me cum shortly, but first I put on nipple clamps, which Miss Hailey adores.

After some strokes and edges, the damsel informed me that she would not let me cum, but would instead grant me endless edges for the rest of my life. She said that denying my orgasm would give me a greater orgasm. If she had me ruined my orgasm for every 100 edges, and did it all over again and again. I'd eventually feel that ruined orgasm become divine.

I was worried she wouldn't let me cum, but she let me have a full orgasm at the end of the tease. It fascinated to me.

Miss Hailey instructed me to clean up after I finished the tease and locked my cock again. She told me that she is afraid of unlocking me once more that if she does, she would lose me again. Miss Hailey's planning to train my ass with a strap-on shortly. That is now my new world.

I don't like having stuff put inside my ass, but I'm Miss Hailey's slave now. Her happiness is the most important thing to me, thus I shall obey her command. And it is just one aspect of our lives; there are so many things we will experience together.
Continue: My journal of Chastity Series (Day 280 - Day 286)
Last edited by captivewhim on Tue Aug 29, 2023 2:22 am, edited 2 times in total.
User avatar
Shattered
Experimentor
Experimentor
Posts: 1242
Joined: Fri Jan 11, 2013 6:41 pm
I am a: Switch
Location: United Kingdom

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

Post by Shattered »

Still enjoying keeping up with these, it's such a lovely piece of work you're making.

That said, if you keep going I'm very curious how you'll handle it :lol:
captivewhim
Explorer
Explorer
Posts: 17
Joined: Sat May 27, 2023 2:59 am

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

Post by captivewhim »

Shattered wrote: Mon Aug 21, 2023 9:39 am Still enjoying keeping up with these, it's such a lovely piece of work you're making.

That said, if you keep going I'm very curious how you'll handle it :lol:
What does it imply? :-O Wait, don't tell me; I'm sure I'll figure it out on my own shortly. Man, you've made me both nervous and excited. :w00t: :-D
User avatar
Shattered
Experimentor
Experimentor
Posts: 1242
Joined: Fri Jan 11, 2013 6:41 pm
I am a: Switch
Location: United Kingdom

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

Post by Shattered »

captivewhim wrote: Tue Aug 22, 2023 10:31 am
Shattered wrote: Mon Aug 21, 2023 9:39 am Still enjoying keeping up with these, it's such a lovely piece of work you're making.

That said, if you keep going I'm very curious how you'll handle it :lol:
What does it imply? :-O Wait, don't tell me; I'm sure I'll figure it out on my own shortly. Man, you've made me both nervous and excited. :w00t: :-D
Minor spoilers, but worth reading because you wouldn't figure it out
Spoiler: show
From C6 onwards, characters from my tease outside the main chastity series make an appearance and are relevant. So you won't recognise them playing them in order, but I suppose that's also fine. It's written in a way so you don't need to know them anyway (If I recall correctly...lol)
Major spoilers
Spoiler: show
Well, like you say, you'll see!
captivewhim
Explorer
Explorer
Posts: 17
Joined: Sat May 27, 2023 2:59 am

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

Post by captivewhim »

Hahaha. You know what, I like surprises. I've read the minor spoilers. However, I will hold back the major spoilers until I have finished everything. :-D
Post Reply

Who is online

Users browsing this forum: No registered users and 9 guests