Being that I’m in the holiday spirt, I decided to be kind and not to make my readers wait anymore. Here is the rest of my slave’s chastity story. I especially like the ending!
By my 4th day without orgasm, I was more than a little frustrated, but was surprised to find that my most prevalent emotions were anxiety and what I can only describe as feeling of submission.
The anxiety came from my fear of getting caught. All of my fetishes had always been a secret that I shared with none of my friends and yet here I was, trying to live my life with a large, solid plastic cage locked on my cock and forcing my balls to jut out from my body. I had begun wearing exclusively baggy jeans & button down shirts that extended below my waistline. And everywhere I went, I was hyper conscious of whether there was a noticeable bulge in my pants that anyone might notice. In reality, I’m sure if anyone was looking at my crotch, it was to figure out why I was looking at it so often, but the risk certainly didn’t feel frivolous to me.
At the same time I found myself experiencing a genuine longing for Mona. And not a sexual longing, but more of an emotional need to be near her and a craving for her attention. Over the past few days she had done nothing but tease me and put me in emasculating positions, while holding me in a device that denied me orgasms, and yet I found myself feeling more loyal, devoted and wanting to please her than ever.
As I arrived at our session that day, I assumed this would be the end of our little experiment. Mona was aware my insurance only covered up to this session, plus she had been very happy with my last few assignments, so it made sense that now would be a good time to wrap things up. Even if a part of me kinda wished it would continue…
I sat naked and bound to a chair, explaining my feelings to Mistress Moan and reading her & 2 of her female co-workers my Victoria’s Secret vignettes.
Before long she had me strapped down on my back to a bondage table as she gently penetrated my ass with her strap-on.
“I’ve really been enjoying keeping you in chastity,” Mona confessed as she rocked the strap-on deeper into me.
“I’m glad that you have Mistress,” I moaned. “As you taught me, this experience should be more about your pleasure than my selfish desires…”
“I’m very happy to hear you think so,” she grinned.
30 minutes of chastity-bound penetration later, Mona pulled out her cock, undid my bonds and told me matter-of-factly to get dressed and prepared to receive my next assignment as she walked out of the room to clean up.
My mind did a double take.
There was no mention of my release from chastity or even of the logistics of continuing to session beyond the limits of my insurance. Just a simple declaration that things would be continuing as they have been, as though it were nothing special.
Suddenly I was overwhelmed with all of the anxiety & confusion that I had read about in chastity fiction on the internet. How would this work? How long would we continue? When would I see her again?
Mistress Mona provided no answers when she returned, just simple instructions to go home and await my next assignment before she showed me to the door. The confusion on my face must have been obvious as she guided me out of her office.
I stood waiting for the elevator, trying to make sense of what just happened, when the door to her office opened one more time to reveal Mona holding out my keys.
“You forgot something,” she said, extending the keys to me. “Do you want them?”
“No, I don’t.” The words came out of my mouth before I even realized I had said them. Mona smiled and closed the door to her office once again.
“What did I just do?!” I asked myself as I walked out through the lobby. It felt so right but it didn’t make any practical sense. I spent most of that evening awkwardly maneuvering through social situations while praying that no one accidentally brushed up against my front.
I awoke the next morning to find a lengthy voicemail of Mona masturbating herself to orgasm. My cock immediately strained to get hard in its cage. She clearly seemed to be genuinely enjoying the dilemma she had placed me in.
The hours dragged on that Saturday afternoon as I waited for some contact from my chastity Mistress, some sense of what my next instruction would be. I had stayed home all day, anxious to go out and risk my chastity somehow being discovered.
Finally, at 6pm that evening, an email from her appeared in my inbox:
“I’m really happy with how our session ended yesterday. I think you are making a lot of progress in understanding your own kinks and inner desires. I love keeping you in chastity and am excited to continue. I give you permission to request appointments to see me and to suggest if and when you would like to negotiate for your release. In the meantime, please keep me apprised of your feelings & thoughts. Your guide and therapist – Mistress Mona”
“What does that mean?” I thought as I re-read her email. Request appointments? Plural?! If and when I would like to negotiate for my release? How long does she intend to keep this going on for?! I thought when we started that this “fantasy exploration experience” would be for just a few days, tops! Now it was starting to sound like I might never get out.
I had suddenly gone from participating in a realistic simulation of one of my greatest fantasies to actually being the main character in one of the chastity stories I had read on the web. Problem was, while in those stories it was always hot when the female keyholder decided to keep the poor guy locked in chastity for much longer than he wanted, in real life it felt both scary and impractical.
How long could I go through life with a hard plastic cage on my cock? Eventually someone was bound to notice. And how long could I afford to pay Mona to meet with her? The cage had been making it hard to sleep, as it would often wake me up as a nocturnal hard-on caused it to yank at my balls. And it required me to lubricate it several times per day to prevent chafing. Plus I hadn’t been able to concentrate on anything but Mona and the cage all day! How would I ever get anything done if I lived like this for any length of time? Of course, at the same time I felt excited and comforted by the fact that Mona was in control of my situation and that made me want to be all the more close to her. Ahh!!! This situation was driving me insane!
I quickly drafted a reply to Mona’s email as my mind swirled with thoughts of losing my job because I could no longer focus on my work – or worse yet, the humiliation of having one of my female subordinates notice the bulge in my tighter fitting work pants:
“Mistress, thank you for your willingness to continue this experience with me and I am very glad that it makes you so happy. Over the past day and a half I have been feeling increasingly anxious & distracted as I consider my situation. Would it be possible for us to meet tomorrow afternoon? I have a strong desire to confess my feelings of desperation to you and be physically humiliated by your strap-on.”
I hadn’t planned the last request until I wrote it, but it did articulate what I was feeling. Much to my surprise, more than an orgasm, what I really desired was to feel a physical manifestation of her intimate control over me.
“I can see you,” she at long last replied, “but I’m busy most of that day, so it will have to be late.”
“Yes! No problem Mistress! That would be great!” I was too happy not to have to spend another day without her to care about the time.
Sunday afternoon she texted me that she’d be later than she had thought and I would have to be patient. I spent the entire afternoon alone in my apartment attempting to distract myself from thinking about my predicament. Working out, watching videos on YouTube or anything else mindless seemed to work a little. The impossible thing seemed to be focusing my mind on anything productive.
By the time we finally got to meet it was late enough that we were the only ones in Mona’s therapy office.
I sat before her, hands cuffed tightly behind my back, wearing nothing but my chastity device and confessed all of my feelings to the woman who, in just a few short days, had become the center of my world.
She listened carefully to my plight of anxiety & need for release from the device for practical reasons and then asked a carefully considered question:
“Do you think, as with anything new, that there is a bit of an adjustment curve here? That, like the stages of grief, while your first reaction might be anger or denial, with enough time you might come to reach acceptance and adjustment to your situation?”
I understood where she was headed, but I didn’t want to let her mind go there.
“I think that makes sense Mistress, but I’m not sure it’s worth getting there if it means disrupting my life to do it.”
“Interesting…” she mused. “Let’s discuss more while we give you that stimulation you were craving…”
Before long, I was bent over a bench, hands still cuffed behind my back, while Mistress Mona stood behind me, thrusting her strap-on into my rear. She had for the first time since my experience began, freed my cock from its cage (not that the handcuffs would allow me anywhere near it), only to attach stimulating electrodes to it while she fucked me.
“Do you realize how lucky you are to have found someone you could explore your greatest fantasy with?” She dialed up the intensity of the electrodes as she asked the question.
“Absolutely Mistress! I am incredibly lucky & grateful to have been able to share this experience with you.”
“Then are you sure you want it to end so soon?”
Her question was sweetly worded but torturously maddening. My mind knew it needed to end so I could get back to my life, but at the same time, it has been my greatest fantasy for a reason, and as a result of it I felt close to Mona in a way I had never felt with anyone before.
“I’ll give you two options,” Mona said, pulling me back from my own thoughts. “Either you can, A – spend another day in chastity & take on your fear of going work locked up before earning release or B – I’ll give you an orgasm now but then you have to spend another full week locked up.”
I thought long and hard before answering.
“I’m sorry Mistress, I know choosing B would make you most happy, but…I just can’t do it. I have to go with A.”
“Interesting. You can’t do it, or you don’t want to do it?” Mona challenged. “I think you’re underestimating your own abilities Jay, and that it’s more of a question of what you want in your life.”
Her point, as with most everything she had observed of me in the past few days, was frighteningly accurate. I’m sure I could last longer in chastity if I really tried, and part of me really did want to be Mona’s chastity slave for life. I just wasn’t sure how to reconcile it with the rest of the life I had worked so hard to build for myself.
“Either way though, I am happy with you. Your assignment for tomorrow will be to text me 3 times throughout your work day with updates on how you are feeling.”
The chastity device went back on before my handcuffs were released and I left feeling deeply cared for, educated and amazed that I although I had just been fucked in the ass, had my shortcomings analyzed and been denied orgasm yet again, I could leave feeling so good.
To my amazement, I had no issues sleeping that night and found it easy to focus when I got to work. No one seemed to even slightly notice the minor bulge in my pants and I almost forgot about it at times while I was working.
Even more surprising was when I found myself texting Mistress Mona at lunch that I was doing fine and could probably hold out another day or two if it pleased her. My genuine desire to make her happy had become so strong that I was eager to offer up 2 days instead of just 1 more. She eagerly accepted my offer to extend.
Although it appeared that Mona’s theory of acceptance & adjustment to one’s circumstances was accurate, my balls still felt abnormally full over the next two days as the chastity device’s cock ring continued its uninterrupted weeklong mission to pull them away from my body. For the past 7 days my life routine had been altered to include things like regularly lubricating my balls, always remembering to bring q-tips into the bathroom to clean the device after I pee and giving myself an enema before every session in case Mistress Mona felt like penetrating my ass. I had adjusted myself in humiliating ways for this woman and yet now it all felt strangely normal.
Her final assignment was for me to document my entire experience and all of my feelings along the way. If she liked what I wrote, she emailed, she would give me back my keys. I arrived at our final session proud of what I had written and eager to share it with her.
Soon I was once again in a straight jacket, bound to a bondage bed as Mona lay next to me, paging through my write up. I was in heaven, feeling closer to her than ever before.
“This is very good work,” she at last announced with a smile. “I’m very proud of how much you have learned about yourself.”
I was beaming.
For the next hour she teased me relentlessly, having fun with how easy my cock was to manipulate after having been imprisoned and denied for a full week, before finally allowing me the orgasm I had for so long desired.
“Oh goooodddd! Thank you Mistress!!!” I moaned in ecstasy as the cum erupted from my body.
However before I had even recovered, Mona had stepped out of the room. I waited for her to return, eager to share my gratitude for all she had shared with me.
“Mistress, I can not thank y…” I started to speak as she reentered only to be cut off as she strapped a ball gag into my mouth.
“Listen Jay,” Mona said calmly as she sat next to my still bound body. “I’m really proud of how much you’ve learned about yourself from this experience, but as your therapist, its clear to me what you really want for yourself, even if you haven’t fully come to accept it yet, and it would be irresponsible of me not to help you achieve those wants when there is something that I can do about it.”
“Don’t worry,” she added, noticing the concern in my eyes, “I’m still giving you back your keys as promised.” She placed the lock to my chastity device along with its keys on the table next to me. “It’s just that I’m also giving you something else…a new lock…”
And with that she resecured the device on to me with her new lock.
“I think we’re going to have a very productive next few months…”