Ninety Days

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New Mistress requires ninety days of chastity from slave.
6.2k words
4.46
64.7k
18

Part 1 of the 4 part series

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

It started innocently enough, a playful comment made over dinner while we got to know each other. Maybe it was the wine; maybe it was her playful grin that at once delighted me and gave me a sense of longing, something that told me that I like this smile and I'd like to see it more. Regardless, the result is evident and I guess the beginning circumstances no longer matter because here I find myself, a little more than three months later, held captive by her charms and near the point of begging for more. But as I sit here, nervously checking the street below through the crack in my blinds as she searches for a parking space on my street, I know I would make the same comment again and wish for the same answer and result.

When I see her walking up the street toward my flat, a pang of desire and excitement shoots straight to my caged cock. I've been confined in this cage for the past ninety days because she had the power to hold me to that comment made over dinner. Over the past three months we've seen each other often and each time I've asked for even a few minutes break from the cage she's reminded me that I had agreed as an initial condition of my submission to remain locked up for ninety days while we established a connection. The firmness and resoluteness with which she has managed her end of the bargain has surprised me and now, with the deal concluded, the thought of freedom and the volcanic orgasms that await me have me near trembling. In fact, the promise of release this evening has been at the forefront of my thoughts for the past six weeks.

I greet her at the door and she looks more beautiful than before, something that seems true each time I see her. Inviting her in, I take her bag and set it aside excusing myself while she strides into my flat with a confidence suggesting complete ownership. As has become our ritual, she seats herself comfortably in the high-backed chair in my parlor, crosses her legs and waits for me. I return, now naked, hand her a glass of white wine and kneel at her feet. We exchange pleasant conversation and laugh easily, each comfortable and content to be together again. Our arrangement has worked exceedingly well but now that our agreed upon three months has passed the future is uncertain and I wonder how or if I should broach the subject of the beyond. She speaks of it first.

"So, our three month agreement concludes this evening. Where does it go from here?"

"Yes, Ma'am, it does conclude this evening and I've thought of little else for quite some time now," I offer with a soft smile.

She reaches down with her right hand and takes my left nipple between her thumb and index finger, pinching it with medium strength but strong enough to cause me to buckle slightly. "I suppose," she begins, her fingers still locked on my nipple, "we'll see where it goes from here." She increases the pressure on my nipple and begins twisting it slightly clockwise. I whimper slightly which seems to encourage her as her grip tightens. With her left hand she reaches forward, grabbing a handful of hair on the back of my head and pulls me closer to her. She whispers, "I am going to hurt you tonight and I'm going to make you cry. And then, when I feel you've suffered enough for me, you shall have the reward I know you desperately need and want."

She gives a final vice-like pinch and twist to my nipple before releasing me. "Retrieve your collar, cuffs, the rope, nipple clamps and my favorite cane from the closet and set them here," she says while pointing toward the table. I rise, trembling slightly and move to the bedroom where the toy closet holds the tools of her desire. Carefully selecting all the items she requires, I return to the parlor and place them on the table before kneeling respectfully again at her feet.

She glances over, checking to be sure that all the things she requires are properly assembled, then points to the cuffs. I select the wrist cuffs first, present each in order, my hand open, and palm up as she had instructed me in our first meeting. After she secures the wrist cuffs, a similar process occurs with the ankle cuffs, each leg presented to her, held erect and never touching her. Next she points to my collar and I present that with two hands while lowering my head and offering my neck, though we both know more than that is being shackled. Once my collar is locked firmly on, she instructs me to assume my position over the bondage chair.

I make myself as comfortable as possible with my legs spread wide on either side of the rear legs of the chair and then lean forward over the chair back with my hands resting on the seat. She works with practiced proficiency securing my wrists and ankles to the O-bolts screwed tightly into the chair. She moves around in front of me, flicks my right nipple to harden it then quickly attaches the clover clamp, repeating the same on my left nipple and then pulling down sharply on the chain connecting the two. I gasp immediately as the pain shoots through my chest. She laughs, takes my chin in her hand and raises my face to look at her. "We're only getting started," she says with a sadistic smirk before slapping me across the face with what seems like all her strength. Despite my best efforts, another whimper escapes me but I am immediately in my most submissive mindset.

I catch my breath and attempt to gain my composure as she walks from the parlor to the bedroom. When she returns she immediately slips a blindfold over my eyes then whispers, "I'm going to remove your cage now but even after I free your hands, you will not touch your cock unless I instruct you to, is that understood?" I nod my head in agreement, adding, "Yes, Ma'am" for good measure.

She works quickly, snipping the plastic lock attached to my frenum before retrieving her key and unlocking the main lock. The cage slips off first and then she forces the ring from under my balls and pulls it off. The freedom, after ninety days of confinement, is like nothing I have experienced before and it's was difficult to keep my wits about me. The urge to stroke my cock is unbelievably strong, but I know better than to be disobedient and I'm thankful that my hands are bound.

"Thank you, Mistress, thank you so much," I say in barely a whisper.

She pauses, asking me, "What are you thanking me for, marc?"

"Thank you for keeping me locked up Mistress and thank you for letting me out and, well, just thank you," is all I can manage.

She simply laughs and takes my cock in her hand, adding, "I'm sure you'll thank me again later, too, my boy." Her hand on my neglected cock causes it to begin growing instantly. She grips me tighter and in almost no time it has reached its full length and hardness. She strokes it slowly and methodically and soon my body is alive with intense pleasure. Through clenched teeth an almost inaudible "Oh Goddess" escapes me and then she stops, leaving my hard cock twitching just moments from exploding.

I hear her walking to the table and back and can sense her standing next to me upon her return. Her hand slowly moves up and down my exposed ass before that warmth is replaced by the thin, cool line of a cane. The first stripe of the cane stings me unexpectedly despite my knowing it is coming. She follows it with twenty-nine more in quick succession before thankfully pausing.

She comes to stand beside me again, taking my cock in her hand and begins stroking it anew. She bends slightly forward and whispers in my ear, "We're just getting going." Through labored breath I stammer an almost non-committal "Thank you Mistress, I only want to please you." She tugs slightly on the nipple clamps and then strokes my cock for another few seconds, sensing somehow that much more attention and I wouldn't be able to hold back.

She steps back again, measuring the distance with her cane and then places it against my ass. The first swat finds the place she had hit the most in the first round and I can feel the skin burning in precise lines. She works more slowly and methodically with this set, calculating the strength and placement with precision. Somewhere around the tenth stripe I begin tightening my ass cheeks in hopes of lessening the pain. By the fifteenth my face is burning and my breathing labored while I hope only that I can make it to the end without losing it. At thirty she stops again and returns to the chain on the nipple clamps, pulling them in an up and down fashion which sends starbursts of pain through my upper chest. And then her hand finds my cock again. She stokes it slowly, the pre-cum leaking from the tip providing ample lubricant for her attentions.

I begin mumbling, "Oh Mistress, oh Mistress, thank you, Mistress" until my voice trails off. She leans forward toward my ear, "Thank you for what, marc?" Through gasps of breath I manage to stammer, "Thank you for caning me Mistress, thank you so much. And thank you for stroking me." She laughs and then tells me sadistically, "I'm going to cane you more now, marc." I nearly scream, "Yes! Yes, please cane me more Mistress, please" as I try fucking her hand, completely aroused by her desire to inflict more pain. She releases my cock, backs up and without preamble begins a new set with greater strength. Although I try counting, I am delirious from the intoxicating combination of pain and pleasure and lose track of her strokes somewhere around eight. She continues through my cries and I can only assume she stopped again at thirty.

When she finally stops I feel like I am going to collapse and she senses it. She comes to me, places her hand on my shoulder and whispers, "You did very well, marc. But the night is only starting. I'm going to untie you and when I do you may relax, get a sip of wine and then come kneel at my feet." As she works to untie me I catch my breath, still trembling, completely aroused. I think of how amazing my orgasm is going to feel, how badly I need release and that maybe she is going to grant it now while I kneel before her.

Once free from the bondage, I crawl to her as she makes herself comfortable in her chair. I kneel before her, my cock at rigid attention but my head cast down. "Touch your cock," she commands and I immediately take myself in my hand, stroking it slowly because I know too much friction too fast will lead to an orgasm I haven't yet been granted. Though still blindfolded, I imagine she is watching intently as I stroke my cock slowly and patiently.

I hear movement and her right leg comes to rest on my left shoulder. Quietly, almost imperceptibly, I hear her fingering herself. I calm myself, fighting the urge to cum despite the overwhelming tingling and the building pressure in my balls. Tiny gasps and moans of pleasure pass from her lips and I can hear her working herself faster. Suddenly her finger is pressed to my lips and she gives an urgent command, "Taste my sex, marc." I greedily take her finger in my mouth, licking it and sucking it and wishing so badly she'd let me bury my face between her legs. "I know you want to lick me, marc. In fact, I know you'd do almost anything to lick me right now, wouldn't you?" she adds playfully. I stop stroking my cock for fear of cumming before responding. "Yes, Mistress, I only want to please you. I only want to give you pleasure" I whine while fighting the pulsating muscles of my own sex. She laughs, "Of course you will" and her moans begin again.

Her pleasure grows louder and the sounds of her fingers on her drenched pussy drive me closer to the point of no return. With a high-pitched moan she cums and I can feel her leg trembling on my shoulder. Her moans, interspersed with various curse words, trail off until she gives a final sigh. My cock, more swollen, hot and red than ever is only two or three deep strokes away from exploding, when I moan, "Oh, Mistress, please, I'm so close to cumming! I can't hold back any longer! Please, Mistress, may I cum?"

As if brought back to earth, she responds with a more serious tone than I've ever heard from her before, "No, marc, you may not cum. Stop touching yourself now."

As soon as she told me to stop touching myself, I do. I learned from our first encounter that her instructions are not to be second guessed or questioned, and they are to be implemented immediately. My hard cock twitched of its own accord and it took all my strength and training not to orgasm. Behind the blindfold I press my eyes closed tightly and my face contorts in concentration, staving off the orgasm building deep within me.

I sit panting, afraid to speak, while the preliminary spasms subside and she catches her breath in the chair in front of me. Her leg moves from my left shoulder and she takes a deep breath before speaking. "Crawl to the bedroom and kneel on the rug at the foot of the bed; I'll join you in a moment," and then she touches my cheek softly, reminding me of the intoxicating tenderness she can mix with her cruelty and establishing, with the simplest of touch, that she can have me any way she wants.

I feel my way carefully toward the bedroom, using my right hand as a blind man's cane, thankful that we're in my space and I know where the obstacles, hidden from my view by the blindfold, wait to interrupt my progress. Once stationed at what I presume to be the center of the rug, I wait. The urge to touch myself grows stronger as the minutes pass although I dare not satiate that desire for fear of the consequences.

Soon, I hear her heels clicking across the hardwood floors toward the bedroom and with each step my heart quickens with nervousness and excitement. She passes by me, her hand stroking my back and hair on the way as she makes her way to the closet. Returning, her steps come toward me.

"I am going to remove your blindfold, but only for a moment, and I want you to climb onto the bed and lie on your stomach," she says in a measured tone. As she lifts the blindfold I keep my head down and rise carefully on to the bed, positioning myself in the center, my back up and still burning ass exposed. "Keeping your hands forward, bring your knees under you so your ass in the air," she quietly directs.

I quickly place myself in her desired position and once there the blindfold is returned to my eyes. Next she secures the wrist cuffs to the bed frame using rope, pulling my arms forward and tight. The distinctive sound of the spreader comes next and soon it is wedged behind my bent knees and it too secured with rope to the top of the bed frame. My ankles come last, spreading my legs wide and exposing my ass for her pleasure.

I hear her lift something from its hang in my closet and soon feel the harness gag being slipped over my head. Instinctively, I open my mouth for the ball as she expertly works the buckles and secures the gag. Immediately, I begin to lose myself in my helplessness but she isn't done. The leather hood comes next and as she laces the back and tightens it one eyelet at a time my mind reels with the thought of another caning. Once she finishes lacing the hood she buckles the back and the sound of the cold metal lock clicking into place sends the slightest of spasms through my body. My head encased in leather, the affects of the sensory deprivation take hold immediately. My cock grows hard again and she takes it in her hand. I try fucking it but my position makes mobility difficult.

"I know how badly you want to cum, marc, but we both know my pleasure comes first. So you must wait." She grips my cock tighter causing me to moan and she adds, "I'm going to remove the nipple clamps now so take a deep breath." I fill my lungs with air and hold it while the first clamp comes off and with it the excruciating pain of blood rushing to the previously pinched nerves. She strokes my cock vigorously for a few seconds and without warning removes the second clamp, causing me to scream through the gag, knowing the full strength of my suffering is muted by it and the hood. She releases my cock but I continue thrusting forward at the air, fucking nothing. She bends forward, speaking directly into my ear, "That's right, fuck the air. Fuck nothing at all, something you should come to accept as your fate." I moan loudly and I can hear her chuckle as she moves away from me.

After a few moments I stop, realizing the pointlessness of the exercise and catch my breath. I listen carefully to her movements behind me, hoping to recognize a sound that will give me some hint of what's to come. I don't have to wait long but instead of a sound it's the feeling of her finger, encased in a latex glove and covered with lube, gently massaging my rectum. Her finger slips in easily, is removed quickly and then inserted again with more lube followed by a second finger. The urge to fuck the air returns, my body rocks slightly forward and she reaches around with her free hand and takes my cock in her hand while her fingers work my ass. She finds my prostate and begins the slow, deep circular motions of milking. Releasing my cock, presumably because she knows I am close to cumming, she presses harder on my prostate and the familiar burning-like feeling begins in my cock. My body is alive and deep, guttural moans of intense pleasure mixed with extreme frustration fill the room.

Leaving me trembling, she removes her fingers momentarily, applies more lube then slips three fingers into my ass. She works them back and forth, in and out, fucking my ass with her fingers and with each inward thrust I push back to meet her. She removes her fingers for only a second and quickly replaces the three with four fingers, brought together to form a probe-like wedge and pushes in carefully but deeply. My ass greets them by stretching further as she pushes in and out for a minute, sending shockwaves of pleasure through my torso. She removes her hand again and I know what was coming.

She wiggles her fingers into me slowly, stopping once all five fingers are inside me but before the fullness of her hand can be squeezed through. With extreme delicacy, she pushes in deeper, twisting her hand from side to side as if playing with the dial on a radio. My ass is being stretched to nearly the ripping point but the desire to take all of her in somehow relaxes me and I open up a little more. She presses forward and soon the ball of her hand slips in with almost suction-like ease and once inside she carefully pulls her fingers into her palm, making a fist. She holds it there completely still for a few minutes while I tremble in place.

Her movements start slowly, an in-and-out rhythm coupled with side-to-side rocking. I moan through my gag, the sensation overwhelming and as her pace quickens, I begin shaking my head in a circular fashion, lost and oblivious to everything but the intensity of her fist buried deep in my ass. She continues rhythmically fist fucking me, seeming to care not that I am floating off to another place where she can hold me captive for as long as she chooses. In between my moans of ecstasy and desire, I catch the faint humming of a vibrator I assume she is using to give herself pleasure. The sound invites me into her world and I imagine she is fucking herself to the same rhythm and beat she's fist fucking me. When the thrusting of her fist intensifies and the delicious violence being inflicted upon me grows, so too does her moans of pleasure, mixing with mine in a din of desire.

Through my hood and gag, I speak to her in tongues, begging and pleading to fuck me harder and deeper and never stop. The unbelievable sensations in my ass trace down the nerves through my body, ending at the tip of my cock. My desire to orgasm is uncontrollable and even without direct stimulation I feel it growing deep within me. But despite that familiar feeling, I am left just on the edge, unable to orgasm and happily drunk with frustration.

Something close to a scream pierces the room and she presses her fist deeper and harder and more violently into me. After another few moments all movement and our shared moans stop, the only sounds in the room are the quiet humming of her vibrator and the labor of our breathing. With an angelic sigh, the humming soon ends too, leaving only the deep, subsiding sound of two people returning to earth.

chasteguy
chasteguy
47 Followers
12