Ninety Days Ch. 02

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Mistress and slaves chastity-based relationship evolves.
3.4k words
4.47
33.8k
9

Part 2 of the 4 part series

Updated 10/30/2022
Created 04/25/2007
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chasteguy
chasteguy
47 Followers

Sometimes life gets in the way and busy schedules don't allow for other pursuits. Mistress and I hadn't played in nearly a month and although we shared intimacy, I was growing anxious for more. Compounding matters was the fact that although Mistress had told me I'd remain in the punishment cage for only two weeks until we could find a suitable cock for me to pleasure, it was coming up on a month and I was growing more desperate for release. One evening over dinner at my place I got up the nerve to ask.

"Mistress, I know we've both been incredibly busy lately but thought I was supposed to stay locked in the punishment cage for only two weeks until we found the right boy, and so I was wondering if perhaps we could make an exception as I really need release. Because Mistress, it has been almost four months since the last time I had an orgasm and I'm not sure I can take it much longer."

She set her fork down and dabbed the side of her mouth with her napkin. "Marc," she began, "you've been very strong and very good, and I'm proud of you. But perhaps it's time we had a conversation about us and where we're going."

I swallowed hard, my stomach suddenly knotted because I didn't want to be released. And I think in that moment I realized that I had fallen in love with her and couldn't bear not having her in my life.

She continued. "I think I know what's best for you and for us, don't you?" With my heart pounding and my eyes cast down, I offered a whisper-quiet "yes, Mistress." She reached out and took my hand before speaking again. "In this relationship, I expect total control when it suits me. I don't know where that will lead in the future and I know that things will change and evolve over time, but for now I have a few rules that you must accept, beginning with chastity. You will be kept in chastity and denied release for as long as I choose. And that includes breaks from the cage. I do not want limits placed on this. There will be no more ninety days or two more weeks or anything of the sort. You should expect the cage to be a permanent fixture and it will be removed by me when I choose and only when I choose. You must trust that I know what's best for you in this regard and know how best you can please me, is that understood?"

I swallowed hard again and glanced up at her quickly before looking down again and whispered, "Yes, Mistress, thank you." My cock grew hard in the cage as I began to fully grasp what I had just agreed to. A slight tremor pulsed through my body but I somehow managed to retain my composure.

"Now," Mistress continued, "I have been busy as you know and finding a suitable boy has been more difficult than I expected. I am not simply looking for a random cock to dangle in front of your face. I am looking for a boy who will become a part of us and be a part of our relationship. He will be someone we share as I determine. And this brings me to my second rule even though it should really go without saying, I just want to be clear. From this day forward, you may not give any sexual pleasure nor receive any sexual pleasure unless I decide it to be so. Is that understood?"

She was right, it didn't need saying but I appreciated her stating the rule nonetheless. I nodded my head in agreement and was about to add a comment when she continued. "My third rule, and you can assume there will be more in due time, I'm making to help you fulfill a fantasy. Because I'm kind that way," she added with a playful smirk. "From this day forward, although this could change, you will only orgasm from being fucked in the ass. Not from masturbation; not from receiving oral. And of course you'll never have intercourse again, so only from being fucked in the ass. Let's hope whoever is fucking you has staying power," she concluded with a laugh.

I sat there dumbfounded. She had said early on in our courtship that she expected me to share all my thoughts with her, no matter how bizarre or how I thought her reaction might be. I had expressed the desire to orgasm only that way in an offhanded, half-joking way one evening on the phone. I made a mental note to be more careful what I wish for because I feared those desires too could come true.

Although I couldn't bring my eyes to look at her and instead focused on the halibut on my plate I'd made for dinner, I knew she was looking at me and I knew she waited for a response. I took a deep a breath and looked up. "Mistress, I only want to please you and serve you and obey you and I promise to do my best in that. But I'm wondering if these rules are up for any form of negotiation," I added timidly. She looked at me and smiled. "You know I'm perfectly reasonable and I care about you tremendously, so of course I'll listen to and consider any reasonable argument you have as to why these simple rules shouldn't be implemented immediately."

I looked at her, searched all the corners of my mind and somehow came to the conclusion that "because this will be so hard" wasn't an acceptable argument. I opted instead for the typical buying time method. "Thank you, Mistress. May I please have some time to think about it?" And that's when she got angry, something she had never done before.

"No, Marc, you may not have 'time to think about it'. What do you think we're doing here? Is this some game to you? We've been seeing each other for nearly four months and I've made my expectations clear all along! I expect you to obey my desires and that's final!" she fumed. I suspect the blank expression on my face conveyed the wrong message. To be sure, I was shocked that she raised her voice and displayed such a demanding demeanor. But at the same time, as was evident by my extreme arousal, she had touched a chord that I didn't know existed within me and never would have suspected she could play in a manner that made me want to throw myself at her feet and beg for forgiveness that I'd ever doubt her.

I stammered out an answer. "Of course we're not playing a game Mistress and of course I'll do as you please. This is going to be incredibly difficult for me and I only hope I don't disappoint you," I added to make sure she knew I meant what I was saying. She smiled and said, "Very well. I knew you would see things my way."

We finished our dinner in near silence but the air did not hang heavy with animosity. Rather it was charged with a certainty that the path we were headed down was correct and right and that perhaps we were only beginning to understand the reality we would create. As we finished our meal and I began clearing the table Mistress moved over to the couch and picked up her book, calling to me to join her when I finished with the dishes.

Having finished my chores, I came and sat next to her on the couch. She placed her feet in my lap without looking up from her book and I, without needing to be told, began massaging them and rubbing them, kneading out the stress from her day. This had become something of a ritual between us and one I wasn't sure who enjoyed more. She continued reading while I rubbed and pressed her feet, relieving her stress, desperately wanting to kiss and suck on her toes but I had learned long before not to initiate such desires. We stayed like this for perhaps thirty minutes, Mistress reading and me becoming increasingly frustrated while I rubbed her feet, all the while my mind replaying our earlier conversation and her rules as well as my unvoiced fantasies and desires regarding pleasing and serving her.

Mistress set her book down and looked at me. "I think it's time for bed and tonight I'd like a massage." With that she got up from the couch and moved toward the bedroom. I went about turning down lights, getting us each glasses of water for the bedside and my other typical nightly duties before joining her in the bedroom. She was already naked, sprawled across the bed on her stomach with her arms and legs splayed to either side. I removed my clothes, considered putting on a nightgown for bed, but decided to sleep naked unless instructed otherwise. Taking the bottle of Jasmine-scented oil from the bedside table I poured a goodly amount in my hands and warmed it slightly.

Mistress sighed immediately when my hands ran down her back, coating it with oil, stopping just above her ass before returning back up to her shoulders. It can sometimes be difficult not to bump Mistress with my caged cock but as my hands worked her shoulders and my erection grew inside the cage causing it to extend forward, it would tap her every once in a while. The pain on my cock from the dual points of intrigue was intense, growing more so as my erection fought for a place to go, seemingly not accepting the confinement she has chosen. I tried to focus instead on kneading the knots from her shoulders and neck, working down her back, across and along her waist and then up again to her shoulders.

"Massage my ass, too," Mistress purred and I didn't need to be told twice. I poured more oil onto my hands and began massaging her ass, rubbing it from top to bottom and around the sides, careful not to get too close to her hole unless she requested it. "And my thighs," she added. I worked those gently, using my fingers as if I were playing the piano. As I moved my hands up and down her inner thighs, my desire to touch her sex was almost uncontrollable. The cage began pressing against Mistress's leg and I was quickly losing my ability to control myself.

"I do so adore having that cage locked on you," Mistress cooed as I continued rubbing down her thighs. "Thank you, Mistress," I replied honestly. She continued, "I adore it so much that I can easily envision never taking it off." My cock pulsed and my hands began to tremble and almost unconsciously I brushed against her labia while I continued kneading her inner thighs. She was hot and damp and I whimpered quietly as I moved my fingers back down toward her knees. "You would like that, wouldn't you Marc? Being permanently locked in chastity, constantly frustrated, having to exist solely for my pleasure?" I let out a slow, deep breath, choosing my words carefully before responding. "I have fantasized about it, yes. But I don't know if I could do it Mistress or how practical it would be," I replied, "and, well, I'm just not sure. But I have thought about it, Mistress." My hand inched back up toward her pussy and my arousal and frustration got the better of me and I let my fingers glide for several moments up and down her labia. By now she was very hot and growing wetter and I wondered if it was the massage, our conversation or private thoughts of her own that was arousing her.

"Tell me more," she prodded as my fingers returned to her pussy, perhaps more boldly than they should, although her sigh of pleasure seemed to invite me in. "Well, Mistress," I began bashfully, fighting to keep from trembling as I gave life to one of my deepest held fantasies, "I have always dreamt that maybe when I found the Mistress I thought I could spend the rest of my life with that together we'd create a permanent, keyless lock so that once it went on it was forever." Involuntarily, I worked my fingers into Mistress's pussy a little harder, finding that spot deep within her where her body responded most to touch. "Mmm. Nice," Mistress said through her sighs of pleasure. I pressed harder inside her, rubbing her the way she had taught me, my fingers deep within her while every once in a while my thumb would trace over her swollen clit.

I continued. "But Mistress, just these past few weeks have been so incredibly difficult for me that I'm not sure I could handle permanent chastity. Maybe it's something that could be worked up to, over time, but I don't know," I said. Her breathing was becoming more labored and now her body was pressing into my hand, meeting my motion with practiced proficiency. "Work up to it, yes," she said as my hand continued fucking her. "Maybe that's what we'll do, as an initial goal," she added. I was slightly confused by the caveat of 'initial goal' and curiosity got the better of me and so I asked what she meant. She started fucking my hand even harder and I sensed that it was her private thoughts that now compelled her. I struggled to keep my fingers on her G-spot while simultaneously rubbing her clit with greater urgency and before she could answer my question her body began to tremble as waves of pleasure pulsed through her body. Her hips bucked as she ground her pussy into my hand before her body suddenly collapsed and she sighed contently.

I removed my finger slowly, licked her juices from my fingers and then went into the bathroom to wash up. When I returned, Mistress had rolled onto her side facing me and softly patted the spot on the bed next to her. "Lie on your back," she whispered and I did as I was told. My cock, still hard and nearly bulging out of the bars of the cage, throbbed with frustration and I was still slightly trembling as I took my place next to her. She reached out with her right hand and gripped my cage-encased cock, played with the skin through the bars of its confinement, and then stroked the entire length, causing the points of intrigue to bite even more ferociously into the head. I whimpered, my breath tumbling out of me like a sob. Without removing her hand from the cage, she leaned over, kissed my neck and said, "Yes, initial goal. Now, goodnight." I knew better than to ask her again and so with questions swirling through my head and frustration greater than anything I had experienced before, I closed my eyes and begged for dreams to come swiftly.

A few days later Mistress surprised me, dropping by unexpectedly. It was early evening and I had gotten out of the bath maybe fifteen minutes earlier and after moisturizing my smooth skin, was sitting on the edge of the bed, still naked, painting my toenails. I hadn't heard her come in, in part because I was concentrating on the task at hand but also because I was lost deep in thought, daydreaming about her.

I jumped when I saw her there, leaning against the door jam, arms folded across her chest, watching me. "Honey," I nearly screamed, "You scared me half to death! How long have you been there?" She smiled at me. "Just a moment or two. I was in the neighborhood and thought I'd drop in for a little bit. You don't mind do you?" she asked rhetorically. "Of course not, my Goddess," I replied, "you know I wish you were here all the time." I finished my last nail, closed the bottle of polish and turned my gaze to her. "You look especially beautiful this evening. May I get you anything?" I asked as I wondered over to the closet to get a robe, walking on my heels so as not to ruin the drying polish.

"I'd like some tea please," she called to me as she made her way into the living room. After pulling the silky blue robe over me I wandered into the kitchen, walking carefully, and started boiling water. When I returned to the living she was sitting on the sofa thumbing through a copy of Gourmet Magazine. I seated myself next to her carefully, not wanting to wreck my freshly polished and still damp nails. She leaned forward and kissed me hard on the lips, placing her hand on the back of my neck and pulling me tighter into her. As our lips pressed together I became immediately aroused, although it didn't take much these days to accomplish that feat as Mistress kept me in a constant state of frustration, even when she wasn't there. As we kissed I realized that she was becoming rougher lately in a more masculine sort of way and I wondered if it was a phase she was going through or something else. The kettle started hissing on the stove and she reluctantly broke our embrace, pushing me away with a simple "Organic Green Tea, please."

I prepared her tea and brought it to her on a saucer with a spoon. I was slowly learning her simple pleasures and attempted to anticipate her needs whenever I could. Like so many things, as they became patterns they simply took on a routine-like mindlessness and in this manner my service to her became second nature. And we both seemed to like it that way. We chatted about our day while her tea steeped and it was only with great difficulty that I could keep my hands off her. Either her growing dominance or hints of masculinity, or my submission, increasing femininity and resignation to chastity, or more likely a combination of everything about us, sexual or otherwise because all the lines seemed to have become blurred in the heavenly fog that shrouded us, I was by now completely in love with her although I hadn't yet voiced the words.

She brought the steaming mug to her mouth, gently blew on it and took a sip, before setting it back down again. "Marc," she began, "I have a date with a boy this evening." My heart started pounding immediately, an odd mixture of excitement, fear and insecurity. "I see," was all I was able to spit out of my mouth, my mixed emotions most likely evident on my face. Mistress laughed. "Silly! I think he might be our boy," she said, emphasizing the word 'our' and beaming at me. My eyes lit up, something like relief washed over me although the rapid beating of my heart never slowed. She seemed nervous and excited, almost giddy, as she described him to me. He did seem like all the things we wanted but there was still so much to learn.

As we had discussed before, she would establish the beginning of a relationship with him first and then introduce him into ours. My mind wandered a bit while she talked as I imagined this long-held fantasy for both of us possibly coming to fruition. There was nervousness to be sure, but that was to be expected.

Mistress finished her tea and excused herself to freshen up before her date. I watched from the bed as she touched up her make up and straightened her blouse. I was impossibly aroused watching her and knowing she was primping for a date with another man; someone who could potentially become a lover to both of us. I took a sip of wine while she was finishing up and then rose to walk her out. As we walked toward the door she told me she wanted me to wait up for her and I promised that I would. As I opened the door, she turned to me, kissed my lips quickly then whispered in my ear, "I love you" before she bit my ear lobe and stepped out the door. I called to her back as she was walking away, "I love you too. Have fun tonight!" and with that she was down the steps and out of sight.

I leaned against the door frame, the door still open, the cool breeze brought on by the San Francisco summer evening fog swirling through the street below like dreams searching for sleeping minds to inhabit.

chasteguy
chasteguy
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chasteguychasteguyalmost 17 years agoAuthor
chasteguy's comment to 5/5/07 "Feedback"

Thank you for your feedback and you've brought up some really good points. I've struggled a bit with melding the various major themes into the storyline and I agree that it may be veering off BDSM in a manner I don't intend. It will get back there.

Truth be told, I am writing this story for someone I am getting to know and our conversations in part dictate where I'm going with it. As I get to know her better, and she me, we're finding our interests are drifting in several directions; perhaps too many to capture in a single piece of erotic writing.

Your point about chastity losing its eroticism over time is absolutely correct. That has been my experience as well (usually at around 5 weeks). However, because I didn't talk about the first ninety days and I hoped it was implied that we had been seeing each other, playing and so on, hence the stimulation was there. Still, I do see your point and maybe I'll rework it.

Your point that because my promised orgasm didn't come at 90 days and I am being coerced into this, it therefore isn't consent I'm going to disagree with. This part was actually not entirely a fantasy as I experienced this same thing in a prior relationship. It's erotic manipulation and I absolutely respond to it. For me, one of the paradoxes of enforced chastity is the incredible desire to cum but at the same time hoping it is denied. So while I am being coerced into denial, it is more manipulation of my own desires that perhaps need to be brought out of me. Lastly, because I do want to please her, I will do what she asks assuming we have established trust and a true connection and therein lies my consent.

I really appreciated your feedback, so thank you.

AnonymousAnonymousalmost 17 years ago
Very erotic, well-written chastity fantasy but

reality is different. When chastity is overly-prolonged, it loses its frustration or stimulation effect. The chastised person's psyche turns off in order to avoid erotic after-effects; it's a conditioned response. Sexual release, every once in a while, would reinforce the effects of the chastity by reminding the person what he is missing. There is also the non-consensual aspect of this relationship; BDSM implies consent. While the sub states he is consenting, it is totally coerced so-as not to displease mistress or contradict her. He was promised release at 90 days and never got it; why should he trust his dom since she does not keep her promises? She talks about castration in the first chapter; maybe that is just playing with his mind and his fears but clearly this would destroy any benefit of chastity as he would then lack any sexual desire (without his gonads). Now he is painting nails and wearing high-heels and it seems is cross-dressing. He wants to be feminized. The story is in the BDSM section and does have elements of this, but there are also elements of non-consent, transexual/crossdressing, and forced gay male appearing in the story and these seem to now be major themes. I'm wondering if BDSM is really the correct category?

AnonymousAnonymousalmost 17 years ago
Such a Cruel Mistress

I really dig her!

AnonymousAnonymousalmost 17 years ago
good development

Very erotic. Very nasty. You showed a lot of restraint by not jumping directly into the next step of the relationship. . . I'm looking forward to reading the next part!

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Ninety Days Series Info

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