Summary: After meeting and talking several times, Sir Dante introduces Kim to the submissive desires she's been curious about.

Part 1

Chapter 1 - The Meeting

Kim's profile intrigued me. Although inexperienced she had a clear sense of what she wanted and there were many activities on her list of favourites which matched mine. Her reply to my initial message had more than just a hint of curiosity and our emails progressed into online messages and then chat conversations, to eventually us meeting in person for the first time at a local munch.

She was nervous while we talked face to face, often glancing up to make eye contact then quickly casting her gaze back down to the table where we sat. She was new to this, so I reassured her that it was perfectly normal to feel a little awkward and intimidated at her first munch. I knew the majority of the people there and introduced her to a few which made her feel more comfortable and helped her to relax and just be herself.

Over the next few days we had several more conversations and discussions about D/s, what we liked/disliked, the things we were interested in, and the use of safewords. Once she had developed a comfortable level of trust in me, we proceeded to the next stage, which was making her curiosities of submission a reality. By the time we worked our way up and had done several scenes together, Kim was no longer a stranger to finding herself at my place, stripped naked just after entering the front door, and having her submissive desires fulfilled through the many ordeals and torments that I made her submit to.

Chapter 2 - Her Inspection

After she had removed every stitch of clothing from her body, I instructed her to lie face down and spread-eagled in the middle of the living room floor. I did an 'inspection' by lightly and slowly running my fingers all over her body, starting at her shoulders, moving down the small of her back, over her ass, stopping to squeeze and pull her cheeks apart to get a good view of behind her, and then all the way down her legs. She was very sensitive to this and just a little on the ticklish side, which made it a difficult task to stay in position as I continued to use my hands all over her. I then told her to turn over and continued the 'inspection' on her front side, pausing around her breasts to squeeze, pinch and lightly twist her hardening nipples.

From our previous scenes together she had learned the exact positions that I expected her to be in. When I commanded her to stand up, she would stand with her legs spread apart and her hands clasped behind her neck, facing forward with her eyes closed. I would also command her to get on all fours and she would get on her knees and elbows with her legs spread apart and head facing down. Every time she assumed these positions quickly and without hesitation I would express my approval by telling her that she was being a good girl. While she was in these various stances, I would continue to use my hands all over her body, forcing her to accept my unhindered indulgence of squeezing and caressing. I also teasingly passed my fingers lightly over her pussy and ass, whetting her appetite for pleasures yet to come. Of course, she would not be rewarded with pleasure before having to submit to some pain first.

Chpter 3 - Kim's Spanking

Through our prior discussions I learned about Kim's fascination with long drawn out spankings. She confessed that thinking about being forced to endure one often excited and scared her at the same time. To get her in that frame of mind I had 4 different implements of choice laid out on the coffee table for her to see: a light paddle, a wooden ruler, a leather strap, and another harder paddle. I sat in the middle of the couch and instructed her to lie over my lap. I made sure she was comfortable which was important since, all told, she would be in that position for the better part of an hour.

I informed her that she would be receiving a spanking with each of the toys that were on the table, and in between each of those she would also get a sound hand spanking. This would always elicit whimpering and pleading about how she wouldn't be able to take it all. Since we had gradually worked up her tolerance from previous scenes we both knew that she could and indeed would be taking it all. While she waited for me to begin, I ran my hands up and down along her back, ass and thighs, savouring her nervous anticipation.

Starting slowly but with a firm hand I administered the first hand spanking, gradually covering each of her ass cheeks entirely. I always enjoy seeing skin transform from pale to darkening shades of pink as a spanking progresses. Kim was a delightfully vocal submissive, and I enjoyed hearing the sudden outcries that she was simply unable to suppress. It also enabled me to gauge the intensity of the spanking I was giving her. I didn't want to take her too far too soon since she had a lot more to endure before it was all over. After several agonizingly long minutes of her warm up hand spanking, she got a very brief reprieve as I ran my hands up and down along her body again, squeezing her freshly spanked ass and asking her how she was doing, just to make sure everything was ok. Then the first of the 4 spanking implements was used.

The light paddle was chosen first. It was in the shape of a ping pong paddle and made a nice loud smacking sound as I brought it forcefully down on her warmed up ass. Alternating from cheek to cheek, up and down, slowly then rapidly, I doled out a very effective paddling which had Kim writhing over my lap in a futile attempt to avoid the inevitable. After a proper engagement with the paddle I reverted back to a hand spanking, feeling the newly added warmth radiate off her behind. When I thought she had received enough, as before she got a brief reprieve. While using my hands over her I again asked her how she was doing, and commented on what a good girl she was being so far. Then, before the burning from the previous thrashing subsided, the second implement was used.

So it went, with Kim over my lap on the couch, submitting to the wooden ruler, as a school girl would have been subjected to, then another hand spanking, then the strap, and then another scathing hand spanking, followed by the brutally hard paddle. By this time Kim was sobbing relentlessly with incessant tears flowing down her face. Having checked with her along the way I knew the torment she going through was not more than she could handle. Kim knew very well the safewords that we had established, I made sure of that. If she wanted things to slow down she could have said "mercy", or if she wanted things to stop entirely the generic "safeword" would have sufficed. Neither of these words were used so I progressed as I had informed her, and by the time we were at the last hand spanking, it didn't take much to make her flinch and cry out loudly with each excruciating slap upon her well reddened and blistered ass. When it was all done I let her rest a bit over my lap and gently caressed her back, ass, and thighs allowing my hand to dip down between her legs to feel her sopping wet pussy. I then grabbed a handful of her hair, leaned towards her face and whispered into her ear that she had been such well behaved sub while taking her spanking like a good girl. In between sobs, she stuttered her appreciative thanks. Having endured such a long and drawn out spanking, it was now time to mix some pleasure in with the pain.

Chapter 4 - Using Kim's Pussy

I instructed her to stand up which she eagerly did without hesitation. After all, spending the better part of an hour over my lap getting her ass suitably spanked with a variety of toys was more than enough to motivate her. I spent a few moments admiring her lovely body standing before me with her legs spread and hands clasped behind her neck, and then I moved towards her.

From behind I reached around and unceremoniously grabbed her breasts in my hands and squeezed them, pulling her hardened nipples between my fingers. My hands then wandered down to her drenched pussy and found their way between her nether lips to her swollen clit. I teased Kim by using my fingers in small rapid circles around her sensitive area, and just as her legs were beginning to tremble and weaken with the overwhelming sensation, I commanded her to lie down on her back and spread her legs open.

I knelt between her thighs and then moved over her to take one of her nipples in my mouth, flicking my tongue over it. I then gave attention to the next one, alternating between her two breasts until I could feel her starting to arch her back and gyrate her hips. I slowly moved downward tracing my tongue along her stomach until I was down between her legs. She gasped when I took her clit in my mouth and started moving my tongue on it in the way I knew she enjoyed the most. While going down on her my hands would reach around her thighs to grab onto her nipples which I would pinch and twist.

One thing I enjoyed about playing with Kim was that she came easily and it wasn't long before this combination of pleasure and pain brought her to an explosive climax. One of the rules Kim was required to follow was announcing whenever she was cumming - this she often did with great enthusiasm. There were times when I would be in a bit of an evil mood and would continue to use my tongue on her pussy while it was extra sensitive just after she came. A few minutes later, between shortening breaths, she would announce the arrival of her second orgasm. Completely exhausted from such an ordeal, she was allowed to rest for a few moments and completely soak in the sensations she was experiencing. Then she received the command which was to get on all fours, and Kim knew what she was going to receive next.

Dispensing with my own clothing, and ensuring that protection was in place, I went to her beautifully upturned behind and rubbed the head of my stiff cock up and down her pussy lips making sure it made contact with her sensitized clit. I did this while savouring her anticipation, and then without warning plunged deep into her wet pussy. She gasped as I continued to pull back and then descend all the way back in. I started slowly, sometimes pausing to allow myself to take in the sensations, and then gradually increased the tempo and momentum until Kim was again crying out, but this time in complete ecstasy. While I used her pussy she would sometimes announce yet another orgasm and soon enough my own climax would arrive.

After I was totally spent, I stood up and got dressed, then sat on the couch and called her over to kneel at my feet with her head on my lap. I stroked her hair as she came back down from the high she was on, and when she was back to normal I commented on what a good sub she was. I also told her she had taken her spanking very well and her pussy had been well used, but I was not done with her yet. There was also an aft opening on her that would soon be cleaned out for me to fully use and there were many more toys in the basement room, anxiously waiting to be used all over her lovely body. I made her well aware that she had a lot more to endure before the night was over.

Part 2

After having been striped, inspected, thoroughly spanked, and having her pussy well used, I granted Kim a momentary respite and offered her something to eat and drink. Being a bachelor I didn't have much in the kitchen, but then again, Kim was not there as a social guest so she made do with whatever was available. When I thought she had an adequate rest, I informed her that it was now time to clean her out. She knew exactly what this entailed and a disheartened look washed over her face.

Chapter 5 - Enema cleaning

Kim had a love/hate relationship with enemas. She had listed them as a favourite activity but while receiving one would have done anything to escape from it. She definitely did not relish the thought, or the feeling, of having her bowels filled to capacity and cleaned out with warm water. Her preference in this matter was irrelevant as I marched her down the hall and made her kneel with her nose touching the wall just outside the bathroom door. While she was in this position, I gathered and put the enema equipment together so she could clearly hear the preparations being done. Kim would be filled up with a flustered sense of apprehension even before a drop of water entered her.

I let the taps run until I found the desired temperature and then filled the bag to the brim with comfortably hot water. Sometimes, if Kim was spending the night at my place, I would administer multiple enemas using a mild saline solution, cleaning her out so thoroughly that I could use her ass several times the following day. For tonight's play, one complete enema would be sufficient. When the bag was full, the tube and tip attached, and it was all hanging ready to dispense its payload, I summoned Kim into the bathroom and instructed her to get on all fours. Taking my time I applied a small amount of lubricant to her tiny puckered opening and then slowly inserted the enema tip into her ass. If I thought it wasn't in properly I would slowly take it all the way out and then re-insert it, prolonging the suspense. I rubbed my hands over her back down to her behind, still warm and red from the earlier spanking, then asked her whether she was ready to start. Resigning herself to this dreadful ordeal, she indicated that she was ready to take her enema.

I opened the valve letting the warm water flow freely into her, enjoying the distressed moans that began as she was being filled up. Kim knew that if the cramps became too severe she could ask for "mercy" which was the safeword we used to slow things down. I kept my hand on the valve since she often did ask for mercy a couple times before the bag had dispensed all the water into her. Each time this happened I would stop the flow and then use my fingers to play with her pussy until the discomfort had subsided. When she was ready, the water flow would be opened again. Although it may have seemed like an eternity for Kim, the enema bag did empty its entire contents, after which I slowly removed the tip from her ass. She would start to whimper and fidget about as the water insider gave her the intense desire to quickly use the toilet. I instructed her to stand up which she did, albeit gingerly since moving was now a bit more challenging for her. I admired and ran my hands over her distended belly, and asked her how she felt. Of course she whined about the urgency with which she needed to use the toilet and I mentioned to her that soon enough that would be granted. I told her to sit down on the toilet but not let anything out yet. This was no doubt the hardest thing for Kim to do, and as she cried out over the cramping and increasing pressure I passed the time by grabing hold of her wonderful breasts and playing with them, warning her in a very serious tone not to let a drop out until I gave her permission. In reality I never made her wait very long, although any amount of time would have been agonizingly too long from Kim's perspective. When I thought she had suffered enough I allowed her to expel the water that was anxiously waiting to burst out of her.

I left her to perform this intimate act by herself, but I also left the bathroom door completely wide open - privacy was a luxury that Kim was not allowed to have. She was very self conscious and I purposely walked nonchalantly past the bathroom, doing other things, to make her painfully aware of her embarrassing predicament. I also did this so that if she needed anything I would be able to hear what she was saying. When she was all done expelling the water I made her take a quick rinse in the shower, dry herself, apply some moisturizing cream (after all, I enjoy tormenting tender flesh), and then wait in a standing position for my next instruction. We were now ready to continue our scene in the basement room, where there were many toys waiting to be used all over Kim's lovely body.

Chapter 6 - Kim's Flogging

To the average observer, the basement room was simply a large and sparsely furnished bedroom with an unfinished ceiling - there was a bed, couch, area rug, and a armoire in the corner. What was not visible to the average observer were the tethers at the four corners of the bed, and the discretely placed hooks in the ceiling, the spreader bars tucked away in the corner behind the armoire, which incidentally was filled with floggers, crops, paddles, ropes and various insertable toys.

I instructed Kim to lie face down in the middle of the area rug and spread her legs while I went to the armoire to gather a pair of wrist and ankle cuffs, along with a blindfold. I again went through the same inspection as I had done earlier in the evening paying special attention to her sensitive ass, which was still sore from the long hard spanking she had received. Then I put the blindfold on her and, one by one, slowly clasped each of her extended limbs with a leather cuff.

The next instructions were for Kim to lie with her hips over a round cushion in the middle of the bed. I then went around and attached the wrist and ankle cuffs to the tethers at the four corners of the bed effectively forcing her into an inescapable spread-eagled state. With Kim in this most alluring position I couldn't help but pause to admire her luscious form, spread widely open, unable to hide her delicate looking pussy and ass from my ravenous view. It wouldn't be long before she was writhing in vain to close those legs and escape the torments that would soon enthrall her.

I started with a soft lamb skin flogger. The tails on this flogger are light and velvety, ideal for caressing and providing an excellent warm up. I could use this at full strength without worrying about causing too much pain. I first let them gently fall across her upper back and then slowly dragged them down and over her up-turned ass. I repeated this several times, teasing her, knowing that even though she enjoyed this soft caress, what she really yearned for was something harsher. Without warning I pulled back and swung the flogger down on her ass with decent force. This produced a satisfying loud smack against her flesh which made Kim cry out in surprise. With a rhythmic succession I continued to warm her up using this light flogger, working my way up to the point where I was applying it at full force. However, producing more sound than substance, it was soon time to move on to a more compelling instrument.

I checked to make sure everything was ok with her and then picked up the heavy red and black leather flogger to be used next. This is my favourite for delivering a nice well-formed thud with just the right amount of sting. Again I started by allowing the tails to gently fall across her upper back, and immediately Kim discerned from the heavier feel that this would be far more intense than the previous flogger. After a few moments of building her anticipation I let her receive the first lash. I continued with this flogger, sometimes slower or faster, softer or harder, until her anguished cries indicated that she was approaching her threshold. I then slowed down and decreased the intensity. Being such a wonderfully vocal submissive, her feedback allowed me to continue this cycle several times, raising her close to the cusp of her tolerance and then bringing her back down. Occasionally, in between using the leather flogger, I added some variety by switching to a riding crop and applying smaller areas of sharp pain over the dull soreness of her nicely punished ass. There was however a certain sensitive area right in the middle which wasn't getting the proper attention. That was soon to be fixed.

I selected another flogger which had fewer and thinner tails that allowed me to precisely place a lash containing all sting and no thud. I went to the foot of the bed and instructed her to stick her ass up. Even though she was only able to further elevate her behind by a small amount, it had the wonderful effect of causing her ass cheeks to spread apart, revealing the enticingly delicate target that I was seeking. I aimed and then struck with medium force, landing exactly in the middle of her aft crevice. She recoiled from the pain and I could hear her breath in sharply through clenched teeth as she squeezed her hands into fists. When she had finished writhing in her bonds, I told her in a firm voice to raise her ass again. A dozen strokes later, her crevice had taken on a beautiful shade of bright pink to match her ass cheeks. Having given her a very thorough and complete flogging it was time to make use of the posterior passage which was cleaned out earlier and now waiting to be filled.

Chapter 7 - Using Kim's Ass

Kim started whining as soon as she felt the cold drop of lubricant fall on her tight little opening. I used my finger to rub it around and then slowly worked the lube past her opening and all the way in. I continued to slowly move in and out with my finger until she got used to the intrusion. Then I retrieved an anal probe, just over an inch in diameter with added ridges for sensation, and slowly inserted that into her. She moaned at this violation to her rear passage as I rhythmically moved the probe in and out sometimes twisting it around for added effect. Not wanting to let any other openings feel unattended, I plugged in a small hand held massage unit and placed the head against her extremely aroused pussy lips.

She gasped loudly when I switched on the massage unit letting the vibrations stimulate and send euphoric tingles into her. With the probe ravishing her ass and the vibrator pressed firmly against her pussy, Kim squirmed in ecstasy and it wasn't long before she cried out that she was cumming. After her orgasm I paused only to get a dildo with which to fill her twice as much and then continue. She was now simultaneously getting fucked with a probe in her ass and a dildo in her pussy while the vibrator did its magic. Even though I tried to prolong this wonderful torment, Kim was able to achieve her next orgasm in very little time. She then went limp, completely drained and exhausted, but in a state of gratifying contentment. I stroked her hair as I commended her for being a good submissive, enduring her severe flogging and also making her pussy cum while having her ass tormented, and not forgetting to announce her climaxes as she was required to do. There was however one task remaining for her to endure.

I untied her and removed the restraints leaving only the blindfold on, then guided and instructed her to kneel in the middle of the area rug. She looked extremely beautiful and submissive in this position, kneeling with thighs opened and hands behind her back. I removed my clothing and stood in front of her. As I grabbed a handful of her hair, she didn't need to be told, and instinctively opened her mouth. I placed my hardening cock between her lips and let her use her talented tongue and mouth to bring me to an exquisitely aroused state. I complimented her on how good she felt and reminded her that the only reason she was making me hard was so that I could fuck her up that wonderful ass. When she had brought me to a nice hard state, I told her to get on all fours, while I put some protection in place. I then went to her well spanked, flogged, and probed ass, and rubbed the head of my cock over her puckered entrance. I slowly pushed it past the opening and into her tight passage all the way to the hilt. Kim began to whimper about how sore her ass was as I began to move forcefully back and forth. Her cries only served to fuel my growing climax with the knowledge that I was forcing her to submit to my assault on her poor abused behind. When it did erupt, my climax was overwhelming, bringing me to the same gratifying and content state that Kim had attained.

Chapter 8 - Conclusion

I removed her blindfold. Kim and I lay on the area rug, both of us now completely exhausted and in a sublime state of satisfaction. I pulled her close so her head was on my shoulder and as she ran her hand over my chest I asked her what she enjoyed and whether there was anything she would have changed. Our discussion would be put to good use for the next time Kim was over to have her luscious body tormented and her submissive desires fulfilled.