0 comments/ 13403 views/ 0 favorites First Pain - The Pleasure Goes On By: LucyCanyon Two weeks had gone by and I had not contacted Fay until today. I knew she had enjoyed the impromptu session after her unexpected submission one afternoon. I wanted her to really need the next step, and to follow my instructions exactly. Building up the tension was key to getting her to play along with all my plans. Eventually I sent a brief text asking when it would be convenient to call and discuss her next session. The reply was swift, she would be at home alone between 2 and 3 that afternoon and the mobile would be on. I called towards the end of the hour Fay gave me, making sure she was ready and waiting. As I would expect, Fay answered quite quickly. "I hope you are ready for more of our enjoyable games, I was very pleased to receive your photo - a perfect response," I said, reminding Fay of the photo which had confirmed our next meeting would be at her home. "So, before we agree anything further, tell me what you are wearing today." "Oh, well, just normal things - a pair of black trousers and a white blouse," was her immediate reply. "Interesting, no underwear or shoes then?" I asked quietly. "Oh, I see, well, yes of course I am wearing other things," Fay replied rather too sharply for my liking. "Good, but not good enough. Now you know what happens when you don't answer me quite right? A little planned punishment, though perhaps that is what you were wanting to happen. So, I have noted this and will be making sure your nipples will suffer a little more than they would otherwise have done when we meet. And, I will ask again - what are you wearing today?" By now I was hoping Fay had worked out this was part of the process, the game we would play when we were organising our meetings. If not, she would be suffering even more each time! "Well, a fitted white cotton blouse, black trousers which are quite smart and tight and some low-heeled black court shoes. I have only a white bra and white cotton panties on underneath as its been quite warm today", was the more considered answer I got the second time of asking. "Thank you. Take everything off except your shoes and we will continue our planning once you are naked. Don't cut me off the phone, just leave it where I might hear the movements as you remove your clothes," I said. Fay breathed in, before a brief word of 'OK' and I heard the phone put down onto a surface. It wasn't long before the phone was picked up again, but I had heard movements and rustling that suggested Fay was complying with my orders, despite me not being there to see or punish. Fay came back on the line. "You are naked, with only your black court shoes on?" I asked. "Yes, I have taken everything off as you required", was the soft reply. We were back into the relationship we had developed through the first afternoon spent together, pain and pleasure being the purpose of our meetings. Knowing she was doing as I asked was getting me hard as I visualised the naked body stood talking to me on the phone. "Good, before you get dressed you will take a photograph and send it me as you did your last one. Now, when you know I am going to call as you knew today, you will make sure you are dressed appropriately. I do not like trousers, I expect shoes to have at least a 2 inch heel and I don't expect tights. After that it is at your discretion, but failing to please will lead to an increase in pain when we meet, is that clear?" Fay agreed quietly that this was clear and she would be able to meet this request next time we planned to speak. We went on to agree a date and time for my visit to her house. We both knew we had to be discreet, and it was to coincide with a work absence of her husband. For my own part I worked alone and could travel easily to see her. Finally I reminded her what I expected in dress etiquette. "Remember, you will be under my control then, as you have been now. You will have your usual safe word, but no other word will release you from what we will be doing. When I arrive I expect to see you dressed to please me, but this time I will not specify what you will wear, you may choose. That may bring extra rewards if I am very pleased, it may bring extra pain if I am not... and of course the two things may be the same for you.... Are you looking forward to our meeting?" "Very much so." "Good, now tell me, are you wet? Are you aroused by the planning, by your exposed situation?" I asked quietly. Fay's response this time was immediate, not risking further unknown punishment. "I am very aroused, just the talk and submitting to your instructions has made me wet, which has surprised me! I cannot quite believe that just doing this has caused me to be so horny." "Good, we will leave it there but do not forget the photo. I will see you in three days time. I am so looking forward to some more pain and pleasure, your body is always in my thoughts", and with that I ended the call. Fay did not forget the photo, and about thirty minutes after we had spoken I checked my home e-mail and found what I wanted. She had posed for her own camera rather than her mobile phone one, and had uploaded and sent it. A much better resolution than if taken on the phone, she was naked except for her low heeled shoes just as I had asked. She had also posed somewhat provocatively, almost as if she were daring me, or teasing me. She was stood face on to the camera, legs wide apart and hands held under her full breasts, fingers appearing to tweak each nipple. On her mound was the same neatly trimmed triangle I remembered, perhaps a little smaller and showing more bare flesh than before. A glimpse of her slightly puffy lips was just visible. Horny, and perfectly executed and her half smile showed just what she thought of this - she was enjoying herself! Three days later I found my way to the large house set back behind well established hedges in the corner of a quiet road. I parked, got out and rang the bell. My bag with a few extra things I had not had ready access to last time was by my side. The front door was barely visible from the road I had swung in from, but when it opened I noticed Fay was very careful about how much of her could be seen past me. I went inside the spacious hall and the door swung shut. Turning to look at Fay I was rewarded by a stunningly sexy sight. Fay had taken my instructions and was dressed to please - or at least to tease if you like tight, shiny fabrics and high heels. Fay smiled and then slowly, and without prompting, twirled around to show off her outfit. She then stood with her hands by her side waiting for me to speak. I was aroused, and she had started the afternoon by immediately signalling her acquiescence, even before we had agreed the game had started. I approached her, leant in and kissed her briefly on the lips before whispering, "Sexy, very sexy, well done, I will ask you later what you want me to do as a reward....." Fay was perched on very high black leather ankle boots. Her legs were showing smooth, solid, shiny black nylon that I felt sure would be stockings after our previous conversation. Her dress was deep red with swirly deep orange patterns, and was made of a clinging, figure hugging material that showed off her ample curves perfectly. It wrapped around her full cheeks, and I was sure I could see the outline of the straps of a suspender belt showing through the tight fabric. The dress showed a good proportion of Fay's fine cleavage, the tops of her firm breasts were straining the fabric where the neckline plunged. I was sure she was wearing a bra, and I knew I would be finding out just what sort it was. I couldn't let her start by feeling like she was entirely in control of what she did or wore. Whilst the vision offered to me was astonishingly sexy, and my cock was already hardening, I needed to catch her off balance a little so the doubt was always in her mind about what would happen next. "Very sexy, but I want to know more. Lift up your dress." Fay responded immediately, and lifted the front hem up to reveal her shapely thighs. The tops of the shiny, solid black nylon stockings contrasted nicely with the straps of the black suspender belt holding them up. Her mound was discreetly covered in a wisp of black lace, barely hiding the neatly trimmed mound beneath and seeming to disappear between the lips of an already aroused pussy. "Turn around, bend over that chair, spread your legs wide" Fay again responded quickly, learning already that speedy responses meant less pain, or at least less of the pain she may not want and more of the sort that got her going. The dress was not quite raised high enough at the back, so I reached forward and roughly lifted it above her round, firm buttocks. The thin black strap of the thong covered nothing, sliding neatly between her cheeks. These were perfectly presented again for my pleasure. I stroked the firm globes, lightly touching and teasing Fay, pleased to notice a shudder each time I slipped my fingers between her cheeks and along the fabric of her tiny panties covering the rosebud of her virgin anus. This I will be returning to, but for now I needed to keep her off guard. "You were not quick enough on the phone I seem to recall, you need to know this will not be tolerated. I will blindfold you, and your delightfully untouched cheeks will be my plaything until you can guess what instrument I am using to tease your flesh," and with that I reached down to get the velvet lined blindfold which fitted snugly over Fay's eyes. Taking out a long, thin chopstick I brought it down sharply on the exposed right cheek, saying, "After each set of five you can have a single guess. Only when you get it right will I allow you to take off the blindfold and sit down on your punished flesh to talk to me some more... I love hearing your voice describe your exploits..." I counted a further four swipes of the thin, wooden stick before asking Fay to guess. "Oh, erm... cane?" Swiftly, and without a word, I brought down the chopstick again on her uncovered cheek, the next five blows evening the red marks out across the flesh in front of me. Again I asked, and again Fay briefly thought about it before shaking her head and giving another wrong answer. I resumed my punishment, and I could see the thin strips of red flesh appearing where I had made good contact. I knew these were not unduly painful blows, and Fay was taking them relatively easily, but they served the purpose of warming the flesh. I put a little more effort in and despite the thin nature of the implements, I was rewarded with the first signs from Fay that I was making a mark. Her breathing was coming more rapidly, she eased back into each of the last few blows and I could see her gently chewing her lower lip as each one hit. Again she could not guess, but she asked permission to ask a question. I had not introduced such an explicit rule, but I was pleased she was learning and thinking in such a way. "This is difficult, please may I have a clue that might help?" "You may, but there will be ten blows between guesses, increasing each time you ask for another clue as well as an extra punishment... " "Thank you, that will be OK, I think.... " "So, a clue followed by 10 blows... well, its of eastern origins" And with that I started again. The number of small yet perfectly timed swipes on her glorious ass cheeks were really beginning to get me and Fay aroused. I could see a damp patch forming on the small section of her thong visible between her thigh tops. Her legs were wide spread, her heels adding to both height and the appearance of her firm, toned calves and thighs. As I brought the chopstick down for the tenth time I could hear that Fay was breathing just a little harder now. I paused, awaiting Fay's next guess, but she remained unable to work it out. A second clue was necessary... and I was already forming a plan to fill Fay just a little fuller than she might otherwise have been as one of the punishments. However, I wanted to move on, so I said, "Eastern origins... and used for dining". I felt sure this would be my last chance with these delicate instruments. I rained the swipes down, concentrating on moving lower on to the tops of her thighs, creating a warm, red glow across much of the exposed flesh on offer to me. When I finished Fay said, "I can't believe that much pain could come from chopsticks!" I allowed her to stand normally as I took off her blindfold and kissed her warmly on her full lips. I slipped my tongue into her welcoming mouth and slid my hands around her slinky waist to hold up the rear of her dress. Sliding hands down as we kissed I gently stroked her buttocks, lightly touching and rolling the warm flesh that would shortly be subject to further punishment. I roamed further as we kissed hungrily. Fay was responding now, insisting her tongue fought its way into my mouth and starting to move her hands down to my waist and further. I slid one hand between us and dipped down to search out the front of her tiny thong. Staying outside, my finger traced the damp fabric as far down as its disappearance between the tops of her delicious thighs. Fay moaned into my mouth as I teased the damp fabric on the outside of her pussy lips, but I could sense she was losing herself in the moment and forgetting what the afternoon was now about. I stepped back and broke off the embrace. Fay initially looked puzzled, but quickly stood silent waiting for me to decide what happened next. As I circled around her, admiring the erotic vision in front of me, I asked her what she would like me to do as a reward for her earlier efforts, for appearing so sexily for me. "I think..", Fay blushed a little as she hesitated, "I think I would like to have something in my... my pussy.. at the same time as something, well, er.. something in my bottom." I nodded, then reached out and took hold of her full, ripe breast and held it firm. The fabric of her dress barely concealed the lacy imprint of the cup's fabric beneath, and the hardness of her nipple was pushing through them both. I took hold of this through the fabrics and gently but firmly pulled it taut, whilst asking, "Have you had any sexual encounters since we last played?" Fay nodded, eyes slightly glazed as I continued to pull hard at her sensitive flesh. "Did you enjoy it?" Fay looked a little embarrassed as she shook her head. "Good, tell me about one of them.... and whilst you do it I want to watch you play with yourself. Take off your thong, and tell me all about it...." Fay looked at me and then slipped her hands into the sides of her thong and slid them down over her fantastic legs. The tiny covering gone, her neatly trimmed pubic mound was now visible and I was pleased to see her pussy lips already slightly engorged and aroused, the signs of that heavenly liquid on their outside. As she took the panties off she passed them to me and went to sit on an armchair. Before she could start her description I took each of her legs and spread them wide over the arms of the chair, forcing her to lie back and expose her increasingly wet lips to my view. The dark, solid nylon contrasted sexily with the pale flesh of her rounded thighs and she slipped her hands down to play with the straps of her black, silk suspender belt. Fay presented a most arousing sight, legs splayed, clinging dress hitched around her waist and ever more aroused pussy lips on view. "It was a week ago, he came home having completed a major piece of work and we went out to celebrate. He asked me to dress up as we were going to a smart restaurant so I wore stockings and a dark blue dress for him. The meal was good, the wine got us relaxed and we came home in a taxi almost like teenagers, with him pinging my suspender straps through the dress." As she was talking Fay dropped her right hand to her inner thigh and started to stroke it gently, working her fingers lightly but quickly towards the full, red lips of her waiting pussy. She circled around her sex, over and around, down each side and back, slowly and insistently teasing without touching her aroused flesh. I watched as her fingers slowly approached her open lips, running down the sides and across the top of her waiting pussy. She continued her tale. "We got back home and barely had we got in here when he pulled me upstairs. He only ever wants sex in the bedroom, and he tugged me there before he started kissing me again, whilst taking my dress off very quickly. I was enjoying the kissing, and I could feel him getting hard as he pressed against me. I was getting a little moist myself, and he stuck a finger quite harshly into me, pushing my knickers aside. I quite liked this, it was almost a little rough and forceful... something which I think you have discovered I like!" As she recounted this, her own middle finger sank between her flushed pussy lips, and was driven home. She groaned as she spoke, guiding another finger to join the first and beginning to force them in and out of her waiting sex lips. I could see she was getting flushed, the telling and the playing was getting her aroused, so I reminded her to continue. "It was going fine until he just withdrew his finger well before I was ready, and then tore my favourite panties right off in his haste to get at me. He dropped his trousers quickly, laid me flat on the bed and shoved his cock inside me as quickly as he could. We made love, and I did try to increase my feelings, my experience, by wrapping my legs around his back, but this seemed to impede his thrusting so he pushed them away. It wasn't long before he unloaded his cum into me... and I was so frustrated as he stopped almost immediately, rolled off and smiled as if he had done me some great favour." Again Fay paused as she worked another finger into her increasingly full pussy, and began to seriously pump them in and out. I could hear the sensuous sound as Fay's juices ran around her fingers. The soft squish of noise arousing, the sight of an exposed sexy body making me hard and ready to fill something up! Fay began to breathe harder as she approached her orgasm, her story telling forgotten as her body's sensations took over. I brought her back to reality by asking if she had anymore sex from him that night. "What,.. erm, sorry, no. He played a little ..... with my nipples after he finished, but..... he went soft quickly and lost interest.....oohhh, in sex. I was left frustrated ...aarghh.... again, full of his juices again but he had no.... ooohh..... idea that this was a problem he ought to be doing something about." Fay continued to plunder her sexy body as she spoke, her words quite erotic and forthright compared to how she had started the last time we met. Her fingers were thrusting into her pussy quite hard now, and her sentences were becoming quite stilted as she strove to keep her control. I had a choice now - leave her and punish the failure to ask permission if she came without asking me, or stop her now and watch the frustration build. I decided I might like to punish her further before I brought her to orgasm, so I just watched her fingers buried deep in her now dripping love tube as they pumped away ever faster. To keep her going I asked Fay what she would have wanted from him after he came, what could he have done to pleasure her. Thinking about this was obviously a perfect distraction, for even as she described this she got ever closer to cumming when she shouldn't. "Ooh, I would.... have asked him.... to use his fingers.... like I am, and perhaps in .... a ...aargh.. different position....... oh, god, so close.... to see if he could.... fill me... completely.... perhaps......Aarrgh, oohhhhh god , cummminnnng.....," and with that her body tensed and she let out a loud moan as her orgasm washed over her. I watched, aroused by the sight of Fay as she came. Her stocking covered legs with their heeled ankle boots were spread wide over the arms of the chair, and her slinky dress was hitched high on her waist. Her tiny thong was on the floor as her three fingers of her right hand were buried in her sopping wet pussy. Her left hand had been rubbing the top of her clit at the end, which seemed to be the final trigger to take her over. First Pain - The Pleasure Goes On When she came down from her high I walked over to Fay and told her, without smiling, to stand up. Fay did so, a little unsteady, and her dress dropped to cover her fantastic legs. I walked around her and undid the zip at the back of her dress, and quickly slid the sheath like fabric down her body until it settle around her heeled boots. Her basque was exquisite, and continued in the vein she had established when I first arrived, in that she had dressed to tease. It was shimmering black, clung to her waist and hips with six straps holding up the shiny, solid black stockings. The cups barely covered her full, ripe breasts, and her deep pink, round nipples were clearly visible through the lacy fabric that the cups were made of. Her nipples stood proud, pushing at the fabric, hard buds of flesh just waiting to be punished. "You didn't ask to be allowed to cum... and you came before me. Do you think you should be punished for this?" I asked of Fay as I motioned her to step away from the crumpled dress. As she did so she lowered her face slightly, and said yes. "I am sorry for my mistake, I got caught up in the excitement and forgot. I should be punished for this," was Fay's rather contrite response. "Bend over, now, this is only the start," I said firmly, and watched as Fay turned and bent to lean over the chair she had recently orgasmed in. Before she had time to settle I brought my hand sharply down on her exposed cheek. She gasped, but I continued very quickly, not giving her time to get any relief from the blows. I rained them down quite speedily, alternating between her glorious, round cheeks and covering all the bare flesh in front of me. I could feel the heat coming from the increasingly red flesh as I made sure all her buttocks received a sound spanking. After what must have been forty or more blows Fay was moaning and whimpering slightly, but I knew she was also getting some pleasure out of this. I stopped, slipped a finger between her cheeks and found the dripping pussy lips waiting to be played with. She groaned as I teased the opening, before covering my finger in some of her delightful juices and teasing her rear hole. She tensed slightly as I pushed the tip of my finger in. "You will be getting something a lot bigger than my finger in here before too long, but now you have a chance to balance things up. You practiced taking all my cock last time, and failed. You will take it this time, and take it until I cum. If you manage to give me what I want, a lovely deep-throated orgasm, I will use only the five inch plug. If you fail, it will be the seven inch one. So, you have only one choice to make - do you want to kneel in front of me and sink your luscious lips over my cock, or lie on your back and have its length slide into your sexy mouth." I waited for a few seconds as Fay considered how she would best be able to take my, still modest but absolutely raging, seven inches of stiff cock. She smiled a little and said she would lie back and have me slide in. I allowed Fay to stand and let her lead me to the low table with the cushions already covering it as requested. Fay lay down and leant her head back - what an erotic sight she was. I was firm and erect already as I took of my clothes. My cock was just at the right height, and I eased the tip in between Fay's waiting lips as she leant to take me. Her ripe body was exposed before me, the basque accentuating the curves of her glorious breasts and full hips. Her stocking covered thighs still visible, her feet on the floor as she took more and more of my stiff cock into her hungry mouth. I reached to tug at her nipples through the fabric of her basque, before pulling both tits free of their confines. Fay gasped around my cock as I tugged and nipped hard at the aroused flesh. I continued the pressure, and slowly more and more of my cock was disappearing between her red lips. The sensation of her warm, wet mouth and tongue was almost too much, but I wanted to give Fay the chance to take me all the way. She was breathing heavily now, and taking me around my sac to control the pace at which she felt she could take my hard cock. Finally I felt the head of my cock enter a warm tight throat for the first time. Fay gagged a little and I eased back but she was not letting me go, sucking and pulling me back in now she had got the technique right. I sank my whole length into her mouth and throat, watching in awe as it disappeared. Fay's eyes were closed in concentration as she stroked my balls and slid her nails along my sensitive perineum. I pulled hard at her nipples as I felt the familiar tingling in my sac. I eased a little out, gave Fay time to breathe in and get ready before forcing my cock in further, Fay's lips tight against my balls as I erupted. I tensed, and pulse after pulse of my hot cum shot into Fay's throat. After the first two streams of cum, I eased back and continued to cum into her mouth, onto her tongue as I was wracked by a huge orgasm. Fay sucked and swallowed, eyes now open as she struggled to take all the hot, white liquid that had streamed, then slid out of my cock. Finally I pulled slowly back and took my cock away, helping Fay to sit up and swallow the last of my first orgasm. "Well done, that was fantastic and I am pleased you managed to take all my cock. Now, turn round and bend over." Fay responded immediately, presenting her full round cheeks to me again. I slid some of her copious juices from her sopping cunt towards her rear rosebud. Easing a finger in at first I was delighted at how tight she was. Fay groaned and swayed a little as I roamed around, and then started to work another finger in. This was tighter, and it took plenty more pussy juice before a second digit was finding its way in to the first knuckle. Fay's response was to groan louder, but push her firm ass cheeks back, helping me push my fingers in further. At this, I took them out and reached for the five inch plug. Without warning I pushed it hard into her cunt, covering it with her flowing juices, before starting its journey into her anus. Twisting and turning it to help it find its way in, Fay groaned and moaned but said nothing. More and more of this small plug found its way into her virgin ass before the wide bit popped in and the flange settled in between her still red cheeks. Standing her up I turned her to face me. She was a little flushed and some of my cum still stained the corner of her mouth where it had leaked. I reached out and wiped it, giving her my finger to lick it clean. Fay did this without a murmur, sucking my finger into her mouth with a teasing glance towards me. The smile was immediately replaced by wide-eyed look of concern when she saw what else I had placed ready for use. The two nipple clamps were laid out and I picked up the first. Fay took a deep breath as I reached out to expose her right breast again. Rolling the nipple around between my fingers I slowly teased it erect, hard and prominent from her full, ripe breast. I opened the clamp, let it close gently and tightened the tension until it was firmly in place and I could see the look on Fay's face starting to turn to worry. Just as I stopped and Fay breathed a small sigh, I gave one more half turn, and watched as Fay gasped at the new sensations now coursing from her sensitive nipple. She quickly settled down to the pain, and I exposed her left nipple and played the same game. Arousing it, teasing it to become hard, erect and ready for the clamp which was tightened in the same way. Fay was moaning a little and closing her eyes to help deal with the new sensations. The final turn and they were both in place. "Now, these will stay on until we have been for a short ride and walk out. Leave your cups down and the clamps exposed. You can wear the dress if you think such a tight, slinky garment will not cause you too much pain... but you have 3 minutes to get something else if you wish to. A delay will only lead to a longer time away from relief." Fay pondered only for a few seconds, the sensations from the clamps and the plug causing her to move very carefully. She chose to leave the dress behind and went slowly upstairs to select something else. She was gone less than three minutes, re-appearing, flushed, and wearing a tight black skirt which ended above her knee and a looser fitting, shimmering pale blue blouse. Every step she took the blouse rubbed lightly but persistently on her tortured nipples, the clamps visible in outline to me, but probably not so obvious to others. I could see she walked carefully, her steps short and her ass cheeks taut as she strove to accommodate the smaller plug in her rear. Her face was a picture of concentration as she strove to fight off the rising sensations inside her. I knew the plug would be teasing her now, but the pain from the clamps would be settling into a dull ache and pleasurable feeling as well, working her towards another high. We got into my car, and drove out of the hidden garden into the quiet streets, Fay looking slightly worried until we had moved out of her very local area. We were not going far, a short drive to firmly fix that plug in her before a walk around a much more public place. I asked Fay how she was feeling about going out in such straitened circumstances? "Well, the sensations are painful, but pleasurable at the same time and I am pleased to be able to cope with them at the moment. I am aroused, god, I have never felt so aroused as each bump drives the plug into me, and makes the silk rub deliciously on my tortured nipples. I am a little nervous about walking around, I think it may get me close to another orgasm but I will ask this time." "How is your gorgeous ass feeling? I haven't finished with it yet..." I went on, as we came into a car park on a country park site with a small cafe adjacent. Fay blanched slightly as we pulled in, seeing how many people were around. "Mmm, its easing, warm and glowing and I still remember every blow - and I did enjoy them, thank you, but can I really take some more?", Fay replied. "You can and you will, but the reward will be good, I am sure. Now we should take a short stroll and grab a drink, I am sure it will spark something for you". I had parked as far away from the cafe as I could, and I got out and helped Fay out of her side. She seemed a little unsteady and her walk was very gentle, almost a perfect catwalk as she kept the little plug firmly in place. She was looking a little flushed and the air on her pussy and nipples was arousing her. Her silk blouse was now pushed against her taut nipples, their points emphasised by the clamps causing her exquisite sensations. They hurt, but they are aroused, though how long she can take them for I am not sure. We walked across the car park, passing many people who barely gave us a second look, though a number of men discreetly followed Fay with their eyes when their ladies were not looking. A short stroll, and Fay was beginning to breathe a little more heavily. She asked if she could ask a question. I nodded as we entered the cafe doors. "What would I need to do to be able to take the clamps off before you tell me I can? Could there be a safe word just for these, they are unusually painful and arousing, and I fear I may not be able to last until we return home." I thought about this, inwardly pleased that again Fay had settled into the situation well. We ordered at the counter, and the woman that served us tried hard not to stare when Fay's blouse occasionally was taut against her breast and showing the outline of an erect nipple and the clamp. As I led us to a table towards the corner away from the doors, I made sure Fay went in first and was sat facing the cafe. I could see Fay striving to stay still, the plug causing pleasure and the clamps causing pain... and possibly pleasure, though I had yet to ask how they felt. "How are the clamps feeling, are the teasing your senses in any pleasurable way at all?" "Yes.. sort of, but the pain is beginning to override the initial pleasure I got from them." "Its good you ask, and if you last until our return, I will reduce the number of blows to your already red ass and give you the orgasm you desire. If you don't, I will make sure I spank you properly again before we get anywhere near reaching our fulfilment. So, you have permission to take them off when you feel the need, but you will not leave my side until we get home." Fay squirmed as we drank, the sensations building her up nicely. I asked her if she felt she could accommodate something larger in her ass. She reddened a little, but said that now the small plug had been in for a while, she felt the tightness easing, the fullness was pleasurable and that she could take a larger plug if I were to ask this of her. I reached over and gently stroked the prominent right nipple pushing the fabric of her silk blouse out. Faye reacted quickly, groaning as the sensations shot from her nipples to her pussy. Settling back I asked Faye to slip off her right ankle boot and to place her foot onto my lap, massaging my cock with her stocking covered foot. She reached down, the movement forcing another gasp as her nipples brushed again at the fabric of her blouse. Her foot quickly found my crotch under the table, and as she tried to stroke my cock, hardening inside my chinos, I played with the firm, slim flesh of her calf and foot. The nylon felt soft, shiny and silky as I rubbed my hands up and down but her movements were just as teasing and my cock was becoming an obvious bulge which I would do well to cover on our way out. Sliding her foot away, she put her boot back on and we stood up. Faye was breathing harder as we walked back to the car and I knew the clamps were really beginning to take effect now, the circulation had been impeded for over 30 minutes and this was quite a first try out. As we got close to the car, I leant in and whispered to Fay that she may take the clamps off before we got into the car... or wait until we reach the safety of her home. She looked carefully over at me, then around at the car park to see how close others were. As she stood next to the car I saw her open a single button in the middle of her blouse and reach inside to her right breast. Once she had worked out the mechanism she undid it quickly and slipped the clamp off, but was not prepared for the sensation of the blood coursing back to the tortured flesh. She yelled a little, causing the nearest woman to look over and raise her eyebrows at the sight of Fay, hand inside her blouse next to the car. Fay leant on it as tremors shook her, before she repeated the move with the clamp on her left nipple. The woman had stayed watching, but Fay had to take this off and wobbled as the pain and pleasure of the freed up nipples almost brought her to an unexpected mini-climax. As we drove out I smiled at the woman who had watched Fay, realising she had served us in the cafe and had taken quite an interest then. Perhaps we had another challenge in the future I thought, but for now I told Fay she had done well and I was pleased with her. We would complete her session at home and as we pulled into her secluded drive Fay seemed to relax, as if a test had been passed. To keep her on the ball I said, quite sharply, that she should go inside and remove her skirt, blouse and boots. She should find her highest heeled shoes, and they must be higher than the boots she is to take off, and then go to the dining area and bend over, breasts firmly down onto the surface and ass presented for my attention. Fay nodded, got out of the car and opened the door for us. Once the door was closed she undressed as I asked, and I saw the red, engorged nipples for the first time since the clamps had been removed. Still aroused but less so, they were red around the aureola and their fullness was emphasised by this. Fay went quickly upstairs and returned promptly wearing a pair of very high, polished black stilettos, toes peeping out and a strap around her delicate ankle. Passing me by I could see her still retaining the plug, which I was about to take out and replace with something else. Fay lay down, gasping slightly as the hard table top made contact with her still painful nipples. Her ass was now spread in front of me, her full, ripe pussy lips clearly visible and awash with her juices. I walked over and reminded her she had some more blows to take for earlier transgressions, but that the number was reduced for her ability to take the clamps. She smiled and waited expectantly. Her sharp intake of breath was rewarding, her response to the swift, unexpected pain that the first swipe from the flogger brought. Fay quickly settled down again, and I resumed, the swishing of the soft leather strands through the air before they landed was all that could be heard. The slap as they hit was sensual, a softer sound than a spanking, but more tortuous to the receiver. I spread the blows across her still pink ass flesh then strayed down to her thigh tops, all the while landing perfect blows as the pain and pleasure continued. Fay spread her legs as I worked down to her thighs, and I responded by lightly flicking the flogger up towards her soaking pussy lips. The response was immediate and rewarding, a growl and moan and a slight convulsion as the ripples of her mini orgasm went through her. I could see her ass clench around the plug, and decided it was time to finish us both off. Leaning over her prostrate form, I massaged her cheeks lightly as I teased the plug out. Fay groaned as it left her ass and whispered to me that she was amazed she felt empty. I suggested it would not be for long, and asked her to turn over, so Fay was now lying on her back, erect red nipples standing proud. I lifted her sensual legs wide apart, resting her stocking covered ankles on my shoulders before thrusting my cock into her waiting pussy. Coating its solid length in her copious juices, I slid it out and moved it to the entrance to her ass without her realising what was going on. With one gentle but firm thrust I was half buried in the most exquisite, tight ass. Fay yelled, her orgasm catching her by surprise and forcing her muscles to clench hard around my cock. As she came down I slid further in, aided by the space the plug had made. Quickly I was buried to the hilt, my gorgeous, pliant Fay splayed beneath me, heels on, legs spread, tits red and engorged and her eyes shut as the sensations took her. Groaning as I got into my rhythm I knew I would fill her quickly, the feeling of her tight ass too much for my already sensitive cock. Increasing the power and regularity of my movement, my thrusting brought my whole length in and out of her well stretched ass. Fay was yelling, grabbing her own tits as I hammered into her ass. Grabbing her clit and flicking hard I remembered her request, grabbed the last of the day's toys, a seven inch vibrator, and sunk it into her dripping cunt. The feel of it slide past my hard cock in her as was too much and was soon tensing, pulsing my orgasm into her. Stream after stream of cum left my cock, filling her ass with my hot seed as the most powerful orgasm I had ever had swept over me, taking me by surprise as I filled the tight hole of Fay's rear. Finally we both finished, Fay slumping with me on top. I whispered that she had done well again, but our time was up again. We kissed, my softening cock slowly sliding out of her well used ass and my cum sliding gently down Fays spread thighs. She smiled as she stood up, making no effort to cover herself or clean herself of our juices. Had she enjoyed it? A smile, a nod and a thank you was all I needed. Did she want to continue with another session? Could she take any more? Fay thought, and slowly nodded. I smiled as I packed my things away, Fay still naked and covered in my cum. "Good, ring me as usual to arrange a date. Don't forget your standards though, I will expect you to remember everything." Fay nodded, grinned and reached for some cum on her thighs, swirling it on her finger before licking it off the outstretched digit. "Will I be in trouble if I forget....."