Slave Chastity Story Part 2

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!


Chapter 3

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.


Chapter 4

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.


Chapter 5

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…”




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My Chastity Slave’s Story

As you may know from a previous post, I had a new slave in chastity. This was a long time fantasy of his and we had originally negotiated a 3 day scene. At the end of the 3 days I knew he hadn’t really gotten even close to a full taste of his predicament and decided not to release him.  We truly had amazing chemistry together and he responded to me very well.  I informed him that it was in his own best interests to continue with the scene and after explaining the details behind my thought process, he too agreed.

So 3 days became a full week.  I told him the he would have to do something for me in exchange for his freedom and if it pleased me then I would release him.  I decided  that since I enjoyed his writing so much that he had to write me a story about his experience over the past week.  This assignment was not only for my amusement but also a time for him to reflect and process the scene.  I did allow him some “creative freedom”  while writing but I wanted him to keep as much real detail in a s possible.  Needless to say he did and amazing job and it’s 90% true to life.  It’s quite long so I will be posting it in a couple parts.


Mistress Mona’s Chastity Therapy


Chapter 1

“Are you sure this is a good idea?”

“Of course it is Jay,” Dr. Mona said as she finished securing my legs to the chair.  “You’ve been fantasizing about being locked in chastity by a dominant woman for how long now?”

“Years.  Maybe even a decade.”

“Exactly my point.  Don’t you think it’s about time you explored one of your greatest fantasies?  You might be surprised by what you could learn about yourself.”  My latex clad therapist finished her last knot.  After having only met with her for 2 sessions, I had somehow allowed her to convince me that playing out one of my most intimate sexual fantasies would be the most productive way to better understand myself.  Now I sat, naked from the waist down, bound in a straight jacket and tied tightly to a leather bondage chair, with a chastity device that I had originally purchased solely as a masturbatory play-toy locked securely onto my cock.

In front of my vulnerably spread legs stood my new therapist.  Dressed in leather boots & latex, as though she had stepped right out of one of my sexual fantasies, she playfully dangled the keys to my chastity device, knowing full well that this was the first time they had ever been out of my possession.  Something about her had just made it feel so right to agree…

“Dr. Mona, I’m having second thoug…”

“That’s MISTRESS Mona!” She snapped, cutting me off.  “Rule #1, you will always address me as Mistress.”

“Yes, Mistress.”

“Much better,” she smiled.  “Now here is how this is going to work: you will be kept in that chastity device for an indeterminate amount of time.  How long of a time will depend on how well you follow my instructions, obey my rules and remain open to learning about yourself.  I will periodically call you in to meet at times that are convenient for me and there will be regular homework assignments between our sessions to give you a chance to fully embrace your chastity experience.”

She waited a beat to allow the reality of the situation to sink in.

“Now how does that sound Jay?”

“Um, great I guess,” I said nervously.

“Great I guess, what?“

“Um, great I guess Mistress,” I added.

“That’s a little better…at this rate, you may be in that device for a very long time.”  The way she smiled as she ended that sentence made me a little uncomfortable, but more than a little excited.  I couldn’t believe I was actually doing this.  Handing over the keys to my cock, my ability to have sex & masturbate, to a woman I barely knew, but who knew how to push every one of my sexual buttons.

“Now that we have the ground rules out of the way,” my seductress announced as she untied me from the chair, “I want you to kneel down and worship my boots while you creatively thank me for locking you in chastity.”

Any reluctance on my part had flown right out the window. Her commanding tone, her leveraging of my boot fetish and the humiliating task of thanking her for taking away my ability to orgasm was too much for me.  I immediately dropped to my knees and began kissing her boots as best I could in the straight jacket.

“Thank you Mistress!  Thank you for helping me to explore my fantasies!  And for showing me what it feels like to actually be locked in chastity.  And for creating assignments to help me fully embrace the experience.  And…”

“Stop Jay,” Mona interrupted.  “Everything I’m hearing you say is about you.  Your fantasies.  Your wants.  This fantasy of yours is my time to have fun.  You get to say locked in chastity and I get to have you do whatever I want.  So try it again, but this time be less selfish.”

She was surprisingly right – although my chastity fantasy put me in the control of another person, as a fantasy it was always self serving – my imaginary key holders always “made” me do things that I really wanted to do anyway. But that’s not how a relationship with a real person works at all; BDSM or not, its about giving more than receiving.

I resumed my boot kissing.

“Thank you for the lesson Mistress.  You are absolutely right.  This is about your pleasure, not mine. I will do whatever you desire for me to do.  I will engage in whatever acts you find entertaining and I will do whatever it takes to please you and any other Mistresses you desire.”

“Much better!” My unconventional therapist stood up from her chair.  “I think that’s some good progress for our first session! I will text you tonight with instructions for your first assignment.  Stay close to your phone!”

“Yes Mistress.”

“Now you have one minute from when I release you from this straight jacket to put on your clothes and be out this door or I’m adding a day to your chastity sentence.”

I was gone 59 seconds later.


Chapter 2


My first “assignment” arrived at 10:12 that night, just as I was leaving the bar with some friends.

“Send me a picture of your cock in chastity within the next half hour.”  Her control over me was evident as I rushed home and found myself, 20 minutes later, standing with my pants around my ankles trying to get enough light on my chastity encased cock to get a good shot of it with my iphone.

“I can’t believe I’m really doing this,” I thought to myself.  Yes, it is my sexual fantasy, but here I am, in real life, rushing home from hanging out with my friends to send an incriminating photograph to a woman who only entered my life a week ago.  And yet, the fact that she was as excited as I was when I had first mentioned my chastity fantasy made me somehow feel more comfortable sending this photo to her than even mentioning the idea of my fetish to any of my friends.

Later that night I was assigned to write a summary of the lessons I learned from our first chastity session together. Mona was pleased that I remembered both the details of her behavioral protocol as well as that I had internalized the idea that my own fantasies were selfish wants and that my primary focus should be on pleasing her.

The next few days contained a wide variety of humiliating assignments & in person sessions, all managing to both play into my fetishes while entertaining my cock’s new owner.  I found myself bending over to learn what prostate stimulation feels like and questioning my sanity as I left my friends at the bar again to go enter a strip club alone at 1am and solicit a lap dance while in chastity.  I was forced to watch & report on an hour’s worth of porn before one session, only to leave with a butt plug still inserted into my ass.

Perhaps the most difficult assignment was to flip through one of my Victoria’s Secret catalogues (Mistress Mona stated it matter-of-factly, as though she knew I had 3 catalogues stashed at the bottom of one of my dresser drawers) and write out what I fantasized as I looked at 3 of the pictures.  I have always prided myself on my creativity and vivid imagination, but allowing my mind to wander while still locked in chastity proved to be nothing short of pure torture.  Mistress Mona was delighted by my end product, but I had barely slept that night as my cock struggled to get hard in its cage.


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Chastity Assignment

I recently put a new slave in chastity and have been giving him little homework assignments to torment him with.

Knowing that he has a weakness for the beauties of the Victoria Secrets catalog, I instructed him to pick three pictures and to write a brief summary of what he was fantasizing about while he was looking at the them.  I was so pleased with the outcome that I decided to share them.  I truly love a slave with a great imagination and they were so well written!

Victoria’s Secret Fantasies

Page 7 – Adriana:

Adriana seduced me into chastity a long time ago, after she got tired of me staring at her.  It was extremely easy for her. Immediately after clicking the lock shut, she dropped her feigned interest in me and has been nothing but a cold-hearted bitch since.  I kneel before her, staring up at her perfect breasts and glimmering lips and beg her for release.  She rolls her eyes and denies me once again.


She has no intention of ever releasing me.  She put me in chastity so I would stop bothering her and releasing me would seem counter-beneficial.  The fact that it causes me to suffer is an added bonus and the only reason Adriana lets me beg at her feet for release each week is so she can witness it.  It’s been 5 months without any freedom, not that Adriana’s been counting.  She really couldn’t care less about my predicament.  It’s too bad that I do.


Page 45 – Alessandra:

Alessandra is a high-class escort who, for a fee, will seduce any man her client requests and get him locked in chastity. I am her next target.  She arranged a “chance” encounter with me at a bar, seduced me and got me to invite her back to my hotel room. Now, having handcuffed me spread-eagle to the bed with a promise of kinky sex, her job is simple to complete. She looks at herself in the mirror reflecting on her latest work with pride. “Poor loser. I’m about to have him locked up and I didn’t even need to kiss him.”


She never asks why her client wants the target locked in chastity or what they plan to do with him once she hands over the keys.  All she says when I beg her to let me out is “Sorry babe. I just get you secured.  You’ll have to take up the rest with your new keyholder.”  And with that she blows a kiss and walks out, leaving me locked up and still handcuffed to the bed.


Page 99 – Woman in Leather Boots & Skirt on cell phone:

On her lunch break from the office, she calls to check in on me.  The answering machine picks up and she speaks, knowing I can hear it: “Hi there sweetie. Just calling to see how you’re doing.  Not surprised you didn’t pick up, the straps holding you to that chair were pretty thick and the locking penis gag would have made it hard to talk anyway.  Well, assuming you haven’t been able to escape yet, I just wanted to let you know that I set the electrodes on your cock to increase in voltage every 15 minutes starting at 1pm.  Oh, and also I just got called into an end-of-day meeting so I’ll probably be home and hour or 2 late.  Hopefully the lube on the fuck-machine pounding your ass will last long enough.  Ok! Gotta Go!  Bye sweetie!”

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