The Most Exquisite Pain

It had been awhile. Since he last touched me. Circumstances dictated we behave with decorum the few times we had met recently; public displays of casual acquaintance only. A handshake here, a brief smile there; knowing we each would use the meeting as a starting off point for vivid fantasy sessions later. Tonight though, tonight was going to be all ours. He left a message at the front desk for me: "Your clothing is ready to pick up at the usual place. Thank you for your business". This message always makes me immediately blush, knowing the clothing he makes ready for me. It makes me wet and my nipples stiffen in anticipation of the torment they will soon experience.

The next two hours are long and impossibly distracted. It's good that my work for the day was completed. Nothing was going to be done now. I leave enough time to get to our spot before you. I want to be ready, as always. I let myself in and find the "clothing" he has picked for tonight's play. A smart black leather skirt that hugs my hips and is barely long enough to cover my ass cheeks. And his favorite black heels. I smile when I realize that is all he has left; we will be staying in tonight.

I go into the shower and dreamily scrub myself to prepare for any touch or taste he may take tonight. A very light scent in discrete warm places to remind him he is mine, and back to the bedroom to dress. As I am slipping the shoes on, I hear him enter the apartment. I smile and settle myself, then walk in to greet him. As I enter the room, I sink to my knees in proper supplication; hands out, palms up; head down slightly. I admit to wanting nothing more than to gaze on his face, his hands, his cock; but I remain still. He walks to where I am and touches my cheek, then moves into the play room without a word.

As I wait, I hear him moving around the room. I know he is looking at and moving items he will use tonight, but cannot be sure what he is choosing. Until, that is, he moves the leg spreader. It has a jangle of metals that is singular to it and the sound makes my already wet pussy begin to pulse. How does he always understand exactly what I need at any given moment? His sense of me is uncanny. It is why I love him so intensely. Lost in my thoughts, I miss his movement and he brings me to the present with a sharp, stinging slap of a thin crop across my breasts. I have obviously missed hearing a soft command from him and his punishment is swift and immediate. I keep my head down and work to keep the gasp of pain from escaping my lips. The wait is not long; "where are you, my pet?" he asks. "I am with you, Sir, body and soul. I am with you"

He instructs me to get up and move to the play room ahead of him. I feel his eyes on my ass as I move in front and the knowledge that the heels have lengthened my legs for him makes me want the walk to last. I know not to dawdle, but I do slow down just a bit and am rewarded with a slash of the crop on the back of the right thigh. I suck in my breath and move into the room, which is quietly lit and set up with my favorite table. I wait for his instruction; it wouldn't do for me to choose my own position. As I wait, he moves behind me and slides his fingers into my dripping pussy. He takes them out and puts them into my mouth. Before the night is through, he will have used all of me, this is how we begin.

Next, he pushes me onto the table on my stomach. He has set it so that I am not prone, I am bent at the waist and only partway. He had removed the breast sections so that my tits fit through. Once they are in place, he attaches nipple clips to each nipple and playfully flicks them a few times. The pain is immediate and exquisite! I tremble at the sensations, careful to never pull away from his hands. He continues to flick and adjust the clips until I am able to recover and settle again, then moves to a space behind me. I feel him caress my left ankle and then the right. Then I feel the ankle wraps of the leg spreader being carefully fitted to me. He nudges my legs apart wider and wider, causing the skirt to ride up my ass and completely exposing my sex to him.

My pussy lips part as he spreads my legs and I feel the cool air touch my exposed clit. I realize I am drifting again when I feel a sudden thud of his thick strop on my right ass cheek. I jump and cry out, only to be punished with a crop strike on my nipples causing my eyes to tear up and a tiny whimper to escape my lips. The strop comes down again, on the left cheek...he is very good about spreading the heat of his punishment. Once more on the right, then the left thigh. I have gathered my emotions and accept and welcome the pain as it comes now. Then he removes the nipple clips in a sudden movement that sends pain cascading through my breasts and into my pussy. I do gasp then, and immediately the crop lands on my ass cheeks several times in quick succession. Eventually he slows the tempo and delivery and begins to run a hand across my ass to feel the heat and small welts he has created. I shiver with each touch, hoping he will find and fill my sex, knowing I must never ask.

His hands are warm and soft against my skin. He spreads my pussy farther than it has been and I feel him insert something hard. It begins to open inside me and I realize he is using a speculum to open me up fully to him. This is a new toy for us and the feeling is amazing. I feel his hot breath right up into my core. My clit is throbbing, aching to be touched, but he knows if he touches me now I will not be able to stop myself cumming. He avoids that and moves to my ass. I feel him spread my cheeks to gain access. Having my pussy gaping open has tightened my asshole a bit, so he works a bit longer to slide a finger inside. No matter how many times my ass is fingered or fucked, I always have the initial pain pleasure and this is no different. I feel his other hand stroking my breasts and tugging at my nipples. The pleasure is immense, now that the pain is gone. My nipples have always been a direct line to my clit and pussy, so the desire to cum is growing faster and faster and much more intense.

I must have pushed back into his hand because the hand at my tits left and I felt a strike across my thighs from the crop. His finger pulled out of my ass and he began to remove the speculum. I waited, as still as could be, to see what he was going to give me next. He moved away from the table for a moment, and then suddenly I heard the whistle of the cat as it was headed down. He struck directly between my legs, hitting my pussy, ass and clit with the tails. I cried out then, pleading with him to please, please fuck me. I felt I would explode and disappear if I couldn't feel him inside me immediately. As I pleaded with him, I felt the head of his cock slip into my pussy. It must have felt like the pussy of someone who had been gang banged for hours; stretched out and sloppy wet, but I knew I was still tight enough to make him feel completely enveloped in heat. He fucked deep and hard, knowing all I wanted was to come. As I bucked against him, he flicked my clit and then rubbed it and I came as hard as I can ever remember.

I tightened around his cock and he gave me time to enjoy the journey out of my mind. As I was coming back to myself, I felt him pull out and move to my ass. His cock is large and he knows the best time to fuck me is as I am still in the orgasm. He stroked my clit and slid the head inside me. With his other hand he slapped my ass cheeks, one and then the other, bringing the heat back up to enjoy. Then, with one quick shove he drove his cock deep into me. He fucked me deep and hard, sometimes stroking my clit or fingering my pussy and sometimes slapping my ass cheeks. I heard him give permission to cum three or four times and I obediently did each time. Finally, I could feel him ready to enjoy his own orgasm. I waited for him to empty himself into me, holding absolutely still while he pumped and pumped into me. I felt him wrap his body against mine while we waited for his erection to end. When he pulled out, he took a moment to remove the spreader and grab a blanket. He led me to the bedroom and pulled me close to him on the bed. He covered us both with the blanket and told me how well I had done tonight and how happy he was with me. I fell asleep hearing the love and safety of his voice.