First Pain Turns To First Pleasure

"That was excellent, very horny and you painted a better picture as you story went on. You are learning and suffering... but are you excited? Is your pussy wet?"

Fay nodded silently, then said, "Yes, it is wet. It was hard for me to do but also exciting".

She was learning, but I didn't think that her story was the absolute horniest or kinkiest of her thoughts, so I opted to test a little further. If I was right I could punish her further...

"I don't think its quite the kinkiest, or naughtiest thought you have ever had. Have you ever wondered what it would be like to have your rear hole toyed with, teased and entered?"

Fay stammered her negative reply too quickly, and her eyes and the heat in her face gave away the fact that she had, and she had not related this to me. After the flustered denials I asked the question again, a little more forcefully.

"Fay, I don't think you are being quite truthful, and its all I ask. Punishment will follow in a moment, but I will try again - have your ever imagined your ass being taken, a finger probing into your rear and most private hole... what it would feel like to be teased there.. or even filled there by something larger than a finger??"

Fay squirmed and tried to avoid eye contact but eventually started talking again, this time with a burning blush to her face.

"Erm, well, I guess it has crossed my mind.. not often.. oh, god, this is difficult... Yes, I have thought about it but I also think its so taboo I couldn't talk about it. I am ashamed of admitting it, but I do wonder what it would be like to .. to have.. a... well something in there... in my anus. There, I have said it now, and I am so embarrassed, but..." and there she tailed off and looked expectantly at me, squirming on the seat and still red in the face. Mental pain indeed.

"Thank you. You should have given me this at first, and now you will be punished for not being so forthright. Once our time has come to an end we can discuss whether or not you and I will engage in this pleasurable, for me at least, way of spending some time. If you choose to avail yourself of my services, I will be more prepared and I will consider fulfilling your darkest thought, and probably doing things you hadn't thought about. Now, stand up, turn around and bend over the back of that chair. reach down and grasp as far down as you can - I want to see you lovely red cheeks on display for me again before they get... redder."

Fay stood up and did as she was told. Bending over she reached behind the chair and presented her bare ass to me. Her pussy lips were nicely visible from this angle, and I could see the drops of her juices forming on the spreading folds. She bent further and her breasts, still inside their silky confines, hung down perfectly. Her red knickers remained stretched between her thighs, just above the knee and effectively preventing her from speedy walking anywhere. I asked her to spread her legs wider, to have her heels at the side of the chair legs, the knickers stretching ever further as she did so. Her balance was now delicate, so I had her in prime position.

I had had no time to select my toys from our selection kept for pleasure, so I was making do with what I could find downstairs. Her nipples would have to wait until next time, when I could clamp and tug them in exquisite torture. For now my hands and the occasional slap will have to do. I reached her fantastic globes, the straps of her suspender belt taught across them and the red marks from her earlier spanking still nicely visible. I stroked the firm flesh, roll the cheeks around under my hands and was rewarded with a groan from Fay, now my plaything. Without warning I brought my right hand smartly down on her right cheek, and Fay started and stifled a gasp. Moving to the side, I started to spank both cheeks alternately, but not too hard yet as I just wanted to warm Fay up for now. After about 20 blows, with Fay beginning to moan softly and her ass cheeks starting to glow, I stopped and collected a couple of items to use on her before I would let her go to contemplate her experience.

My first change to her punishment is a lovely, flexible 18 inch long, wide ruler. Fay cannot see what is coming, and after a little stroking of her gorgeous flesh, I bring it down sharply, but not yet too hard, onto her left cheek. Her response is immediate and loud, a cry out as the pain is markedly different to what she has received before. I walk around to her head and raise my eyes, questioning without speaking. She bites her lips a little, but is nodding firmly and I return to my task. Starting again I alternately swipe her right and left cheeks, selecting different areas with each targeted blow. Now she is ready for it there is only the sound of a sharp intake of breath with each one and a settling of her thighs and buttocks after the blow has been taken. I move my target areas slowly down until the tops of her thighs are being spanked with the flexible, whippy plastic, broad new bands of red appearing on the skin so tantalisingly exposed at the top of her stockings. She is breathing heavier and grips the chair tight but otherwise says nothing. Her red, sex lips are parting more and more almost with each blow, the pain and position Fay finds herself in is clearly arousing to her. I can see the juices of her excited pussy wetting the puffy, spread lips of her sex.

My cock is hard, watching Fay take such delicious punishment is an erotic and arousing sight. I take my jeans, socks and underwear off and move around to her head again. I press the tip of my cock gently against her lips and she opens her mouth and slides my cock inside. She is almost hungrily sucking it in, taking half its length in one go before stopping and looking up at me. I smile and say, "I am going to sink my cock as far as I can into your mouth. If you can take it all, your ass will receive no more punishment today. If you can't, I will be giving you a choice from three more objects with which I can spank your lovely flesh... you only have to choose one."

Fay tried to ease off my cock a little as she took deep breaths. This was something she said she had never done, so I was expecting to be punishing her lovely ass and thighs once more before we finished this session. From the way she had responded I was in no doubt that were I to offer her a chance to suffer more pain for pleasure, she would be taking it. I leant forward, my cock sliding further into her gloriously wet and warm mouth. I let her take it at her own pace, this was her first time at trying deep throat after all, and I wanted to distract her a little too. As she was sucking back and forward on my hard cock, I reached under to free both her breasts from the confines of her red silk bra. Their fullness was revealed as they hung pendulous below her, a little larger than my idea of a perfect pair but still firm and ready to be played with. As Fay tried gallantly to get more and more of my stiff flesh into her mouth she started to gag slightly, the tip of my member reaching the back of her mouth. This I knew would be the tricky bit for her at first, and I leaned in slightly even as I tugged hard on her left nipple.

I was rewarded with a growl around my flesh, the vibrations sending shivers through me and making me realise it wouldn't be long before I would need to cum. The effect was good though, for a while I had been accepted further into her mouth but now she gagged again and I had to ease back. I tugged harder, then held the full breast in my hand and rolled it around. Fay moaned around my cock again, as I eased it further in again and again she took a little more. This was almost too much - six of my 7 inches was now firmly inside this hot lady's mouth, she was bent over a chair with her knickers around her knees and her breasts on display and she had taken many strokes and slaps to the tortured, fleshy globes of her ass. I was not going to hold on much longer, she had one more chance to take the whole length, and I eased back a little and said as much. Fay just nodded, and went back to her task. Her eyes were glazed, fixed on the flesh in front of her and which was slowly but surely filling her mouth again. As she did so I tugged and played with both her fantastic breasts, moving the heavy, firm flesh around in both hands which had the added benefit of making me lean forward into Fay's waiting mouth.

Finally Fay stopped, gagged a little and eased back. Whilst a seriously sexy and erotic sight, she hadn't quite got the deep throat technique just yet and as she let the hole of my length slip out from between wet lips, she looked up and silently apologised. I smiled, and congratulated her on a very arousing performance, but which had just not quite got there. I suggested that if we were to continue this another time, we would return to practice this again. In the meantime, I asked her to make the choice of how she would receive her final punishment for the day, and to bear in mind it might include those delightfully aroused and arousing breasts so perfectly displayed. I showed her the three implements I had selected - the back of a wide, stiff hairbrush; a short length of garden cane and the belt around my discarded jeans. Fay looked apprehensive as she surveyed these items, still bent low and with her legs widespread. She looked up and asked if she could ask a question of me. I nodded.

"How many strokes do you think you will be giving me this time? I am nervous about the marks a cane may leave, but if the number were small enough I feel I could take this best. If I am deserving of more strokes, then I would select the ... belt..", the last bit said in a whisper.

"You did very well in trying to take my cock all the way into your hungry mouth... did you enjoy it?"

Fay smiled ruefully and nodded.

"But ultimately you did not achieve your task, for which your punishment is 20 strokes - I think this will be the belt." At which Fay gasped, bit her lip a little but just looked back at me in readiness. I was amazed just how far we had come today, her ass had already taken many blows but she was about to receive a further twenty. First though I took off her knickers, and spread her legs even wider. Her gaping pussy lips were now displayed, red and aroused. The soft inner flesh was clearly visible, glistening with pearly drops of her juices, which had also started to run onto the tops of her wide spread thighs. Her round cheeks and silky thigh tops were looking a little less red than before, her naked flesh highlighted by the contrast with the silky dark nylon of her stockings. My already hard cock twitched at the sight, and I warned Fay she was about to receive her final blows.

I stood to her left, and gripped my wide, brown leather belt about halfway along its length. Swinging it lazily through the air, it made contact with a sharp thwack on Fay's left cheek. This brought a very sharp intake of breath from Fay before she settled down quietly, the belt clearly being a different sort of pain on the already sensitive flesh of her virgin ass. I was not using the full length of the belt, nor my full strength, but the blows were steadily applied equally to each cheek, bringing stifled moans from Fay as she tried to take each one silently. I could hear her breathing hard between blows, and watched her try to settle and ease the heat on her tortured flesh, but with nowhere to go, and nothing to do but to receive, she became still quickly. With two to go she was panting, the cheeks of her rounded ass glowing with wide red marks as the blood rushed to the surface of her fantastic cheeks. The last two I placed a little lower, just above the stocking line on each leg, on flesh that had mostly escaped the torment. Fay was panting and quietly moaning under her breath, not realising this was over for today. Her sex lips had got more and more aroused as the blows had landed, and her juices running down he thighs gave away that the pain had indeed caused pleasure.

Without warning I moved up against those perfect cheeks and rammed my solid cock home into her sopping pussy. She yelled aloud for the first time that afternoon as I thrust in, sinking almost all the way in in one go. A second thrust and I was buried to the hilt, my cock filling her hot, wet cunt completely. Fay shouted in surprise, and I reached around to take a gorgeous, full breast in each hand. Lifting her head up by pulling hard on her glorious globes, I felt Fay's hands cover mine as I started to thrust hard into her willing body. Almost without warning she cried out and started to shudder, clamping her pussy walls around my cock.

"Oooohh, god, yes, harder, ggrnnmmm AAARGH, fuck.... ooohh mmyyy god...", she screamed as she came loudly and quite unexpectedly around my sill thrusting member. Her orgasm seemed to go on for ages, her body convulsing, her breasts held tight by our hands and her thighs spread wide. Try as I might I could hardly move my cock in and out far until Fay began to relax. I thrust harder and hard, rocking my body forward and backwards as she took my hot flesh. Each thrust in meant I came up hard against the red, tortured flesh of her perfect ass cheeks and thigh tops. As I reached my orgasm, I gripped harder on the round, firm flesh that is Fay's breasts and began to cum. I spasmed hard, shooting three or four pulses of cum into her tight cunt, with the last few thrusts getting the remaining juices out of my now spent cock. It was then noticed Fay crying, though whether or not it was joy or pain I did not know. I massaged her wonderfully pliant nipples tenderly, leaned forward and noticed the tears, but a smile on her face as she looked back at me.

"No more pain for today, I think you have taken more than enough and done it so well - are you OK?"

Fay smiled her reply, "Fine, absolutely, one hundred percent fine. Oh god, I don't know where that came from. I am sorry I started to cry, it was the relief, it was in happiness at the fantastic feeling rather than from the pain."

"Fay, that was just amazing. You played your part to perfection and took more than I thought you would on a first, and completely unplanned, foray into a different game. Whilst we are now back to our normal selves, I would like to ask one thing of you, not painful but potentially naughty and ultimately rewarding."

All the while I could feel my cock softening, though I continued with gentle thrusting into the bent over form of this sexy lady. She had let go of my hands and was now propping herself up again as I rolled her tender, erect nipples around between my fingers.

"Although the pain and the pleasure has finished, I wonder if I can suggest something, something which allows you to ponder what has happened and let me know in an appropriate way whether its is something you want to do again."

Fay moaned her agreement, my semi-hard cock and the toying of her now erect nipples still arousing some pleasurable feeling in us both. As I continued to tease those hard nubbins of puckered flesh I carried on with my suggestion. Fay started to smile as I explained what she should do, and she nodded her agreement. I reached for her silky red knickers before pulling my cock out of her well-filled pussy. Before our combined juices could come out I started to fill her love-hole with the knickers, feeding the silky material in piece by piece, soaking up the glorious liquids and keeping her full. Fay stood up and started to make herself decent again, easing her pained nipples into the cups of her bra before adding the sensuous blouse. She turned her back to me again, and I coated her tortured cheeks and thighs in cooling lotion, gently rubbing it in to soothe the heat and take some of the pain away until there was just a warm glow. The feelings of slowly rubbing my hands around her full, firm ass cheeks, down the tops of her thighs to the stockings and back again was erotic, my fingers lightly sliding across the flesh with a silky feeling of the lotion.

Finally she was able to put the skirt back on, leaving her pussy stuffed full of her knickers as we agreed. As we embraced before she left, Fay thanked me again and went over the request I made. She was to leave the knickers in place until she got home, then take them out and leave them to dry out. Overnight she was to think about the day, and whether or not she wanted another afternoon of pain and pleasure. If she did, she was to wear the same silky red knickers to work in the state they were in from today. Once at work, and in private, she was to photograph the knickers in place, covering her lovely, sexy mound, and send it to me. If she was wearing black stockings, our next meeting would be at my place, if they were any other colour, the meeting would be at hers. If I had no photograph by the end of the day, then we would speak no more of what had happened. Fay smiled as she finished, kissed me lightly on my cheeks and left the house, leaving me with an increasing erection yet again, knowing she was now driving home with her pussy full of my cum and her knickers. I wondered what the following day would bring.

I checked my home e-mail at work at regular times, but I didn't have to wait long. Attached to an e-mail from Fay was a picture, taken up her flowing navy blue silk skirt and showing the cum-stained silky red knickers from the previous day barely covering her mound. They were framed by the same suspender belt attached to barely there, nude stockings, shiny in their appearance and giving me my answer - more, and at her place. The text of the mail simply said, "Further, harder, longer, fuller... please. Fay. XX"