Author's Note: This story will not be for everyone. It is inspired by a real person and I have endured a number of the things that she goes through so I write from experience.


Chapter 1

"You seem nervous," I began. She nodded, biting her lip. I cocked an eyebrow and she said, "Yes." I tilted my head slightly to the side, an invitation to elaborate further and she replied, "Yes, Sir, I am nervous." I looked her up and down. I knew she was about 40 though she took care of herself well so looked much younger. About 5'4", athletic though softly curved body; she apparently swam, ran, and did yoga every day. Brown hair, light brown eyes, clear fair skin, not a wrinkle nor a grey hair to be seen. Quite remarkable for the mother of a 16 year old, a 13 year old, and-the surprise child-a 3 year old. That's where we met, pre-pre-school. I had not realized such a thing existed until I became a parent. Though it was a relief to know that it did. A morning or few a week away from the kids. Though my wife and I shared the parenting duties, it was the mothers of all of the other children who volunteered. Me and nine women, including my wife, on rotating shifts helping the teacher. That's how we got to know her. My wife and I discussed her right after we met her at the first parent social. My wife started the conversation, "Who is the one with the dark secrets?" I replied, "It's obvious to you, too? She has some skeletons in her closet for sure. I wonder if the 3 year old is even his," I added, referring to the father we briefly met before he disappeared into the corner for a business call. "If that is how he is all the time, I bet she feels a bit . . . neglected." My wife nodded and said, "Shall I suss her out?" I smiled and she replied, "I will take that as a yes."

I bet some people thought that she and the 16 year old were siblings or cousins. They had similar builds-we had all met at the familiar pot luck picnic a few months into the school year. The 16 year old was a bit taller and a bit skinnier though she was clearly her mother's daughter. That brought a question to mind. "Is that outfit yours or your daughters?" She blushed deeply, biting her lip again, looking down at my feet. Her voice cracked as she admitted, "Hers, mostly, Sir." The older siblings were in Catholic school and she had worn a uniform to meet me at her house. Saddle shoes, knee high socks, both in white. Plaid skirt in white and black with red trim, white blouse unbuttoned a few more buttons than the sisters would have liked, and red blazer with school crest. "Mostly?" She blushed more deeply, "the undergarments are mine, Sir." I smiled, saying, "Show me." Her eyes widened and she took off the jacket and it was clear that there was a black lace bra under the blouse. I nodded, "And?" She lifted the skirt, the black lace triangle standing out against her fair legs. I twirled my finger in a circle and she understood, turning around to show me her bottom, lifting the skirt so I could see the black line of the thong disappear between her legs. "No modesty pants for you?" She turned around, dropping the hem of a skirt and smoothing it, saying, "No, Sir." I laughed again, "I thought the daughter was supposed to steal the mother's clothes. Do you wonder if she borrows your thongs to wear under her modesty pants?" Her eyes widened and she swallowed hard, looking away. "I won't go there. Today is about you."

I continued, "You said you were nervous, why?" I knew the question would possibly put her on the defensive and I waited for her reply. "This is new to me, Sir," she said, after a long pause. "What? Dressing like a school girl, cheating on your husband, seeking out the punishment you need?" My answers were like slaps in the face to her and she began sobbing, "I can't help it, Sir, I just can't stop myself." I said nothing and let her sob some more, my silence worse than anything that I could have said. After some time, her sobbing lessened, and I continued, "So you need punishment for your . . . sins? You do understand that punishment, done correctly, is not something that you want, yes?" As I was speaking, I stood up from my chair to stand before her. She, still blubbering some, nodded. I waited a few seconds and when she said nothing more, I gave her a firm slap across the face with my open hand, saying, "you seem to be forgetting yourself." She seemed shocked and angry about the slap then my words sank in and she blubbered, "I am sorry, Sir, it won't happen again." I smiled, "Oh, it will happen again, at least a few times, before you learn your lessons. So, you understand that this will be unpleasant at times, yes?" This time, through her sobs, she replied, "y-y-yes, Sir." I smiled and said, "better. How much time do you have today?" She paused, saying, "I have until 5 pm-the girls have soccer practice and the little one has a play date." I hmmmmed, "8 hours? That is a lot of time, isn't it? I think we may be able to accomplish a lot in that time. I am not going to ask you about your experience with punishment and discipline because I honestly don't care. I will find your limits and push them. I will hurt you, but I will not harm you on purpose. You can use a safe word if you need, but you must understand that this will be unpleasant at times. The safe word is for when you believe that you are in genuine danger." She nodded and also said, "I understand, Sir."

I sat down again, beckoning her to lay across my lap, "We can start in a traditional manner." She draped herself across my legs. "Hands behind your back, please," I said as I saw her try to brace herself. I lifted the skirt and clasped her hands tightly with my left hand and caresses her bottom with my right hand, taking in the magnificent smoothness and pondering my good fortune. I said, simply, "count" and I laid the first hard slap on her bottom with no warning or warm up. She yelped in surprised, though managed to gasp out, "one, Sir." I continued for nineteen more open hand spanks, alternating sides and moving from her bottom to the tops of her thighs and back. She squirmed as she took the ever harder spanks though to her credit, she kept count though I heard her beginning to sob again when I paused. "Today, I am going to punish you for your naughty undergarments. Although you came to me for punishment, it is clear that you are also trying to tempt me. In the future, you are to dress in plain undergarments appropriate for your outfit. Do you have what I asked for?" She took this all in and said, "Yes, Sir, it is in my backpack," she replied. Again, to her credit, she took her role seriously. Backpack, notebook, school books-probably also borrowed from her daughter-and a stout wooded hairbrush that I took from the bag. "Excellent, good choice. The ones with the shiny finish tend to her more," I said.

Without a pause, I resumed spanking, equally hard as I did with my hand though with the brush. She cried out and missed counting the first five spanks and I stopped, listening to her sob, saying, "Now now, you missed a few. We will have to start from the beginning. How old are you?" She sobbed out, "thi-thirty n-nine, Sir." I hmmmm, saying, "OK, 40 spanks it is." I resumed and despite her crying, she was able to keep up, realizing that we were starting from one again. I continued the pattern of alternating sides though began to focus on her lower bottom and upper thighs which were starting to go from beyond pink toward bruising, "I want you to remember your punishment until I see you next. We agreed on Monday, Wednesday, and Friday, if I recall." I didn't need an answer, it was not really a question. Her sobbing and squirming grew as we neared forty and she squirmed on my lap in such a way that was quite stimulating. For the last five, I gave her slow, deliberate swats across both cheeks and held the brush for a few moments after each spank, giving it time to reverberate through her body. The last swat, the hardest by far, had her screaming "FORTY, SIR!" and they a curious thing happened-she began spasming in my lap and it became clear that she was in the throes of orgasm.

I waited as her spasming and crying subsided and I said, "Well, that was unexpected. I guess that you are more of a slut than I realized." She gasped but said nothing. "I suppose, since I did not expect this to be so arousing for you, that I will let this orgasm pass. In the future, you will ask permission before orgasm, do you understand?" She nodded, saying, "Y-y-yes Sir." I pinched her slowly bruising bottom several times which broke her post orgasm reverie and she cried and yelped and squirmed and I said, "OK, stand up and follow me." She stood and I also rose, leading her to the kitchen.

I inquired, "Do you have any rice?" She looked at me quizzically, shaking her head, saying, "No, Sir, I could make some." I shook my head, saying, "No, uncooked is fine." She took down a box of jasmine rice from the cupboard and handed it to me. I opened the box and scattered some rice on the floor and placed the box on the counter. "Take off your thong, shirt, and bra," I ordered. I could see that her hands were shaking as she slid the soaked panties down her legs and handed them to me. She fumbled opening the buttons of the shirt though managed to remove it as well as her bra. I admired her upper body-some stretch marks from her three pregnancies, though nothing unappealing. Her small breasts were full for their size and showed only a small amount of sagging. Her nipples were thin, pink, and long with small areolae. She saw me admiring her and she blushed from her face to her belly. I balled up the thong and said, "Open." She opened her mouth and I shoved the soaking panties into her mouth. I used the bra to secure the gag in her mouth. "Hands behind your back," I commanded and she complied. I took a ziptie from my pocket and secured her wrists by her lower back. "Now, kneel." I pointed to the floor in front of me, to the grains of uncooked rice. Her eyes widened and she swallowed. She gingerly lowered herself, making sure that there were grains under her knees, as she knew that is what I would want. Her breathing quickened as her weight bore into the rice, the pain excruciating. Tears began to stream down her cheeks as the full truth of how unpleasant her punishment could be sank into her. She looked up at me and sobbed but she did nothing that would indicate that she did not want to continue.

I smiled, "OK, forty swats and 15 minutes for you and that will conclude the first phase of your punishment." I rummaged through the kitchen drawers and found what I wanted-a rubber spatula. I also noticed a shelf with some cookbooks and I decided to up the ante somewhat. I took five of the thick tomes and placed them on the back of her calves. This was quite unexpected since I was out of sight and she squealed into her gag at the increase of pain and pressure. I moved to the front of her and smiled as she weeped, reaching down to caress my rather swollen erection through my pants. "See what you do to me, slut? Even when you are being punished, you turn me on." Without warning, I brought my hand down sharply onto her left breast and slapped it right above the nipple then swatted the right moments after. She squealed and squirmed and cried as the pain shot through her breasts and her knees as she squirmed further on the rice. "That is a taste of what you are going to get. Only 38 more to go. It's a pity you can't count them for me." I moved to the microwave and set the timer for 15 minutes and pressed start. Without a pause, I continue to slap her breasts-left, right, left left left, right right right-over and over as she screamed into the gag and cried piteously. After twenty I switched to the spatula, welts appearing almost immediately. Her squeals raised in pitch as I neared forth swats though I imagine she had no idea how many times she had been hit. At forty, I stopped and listened to her continue to sob and gasp and watched her shudder. "Good girl," I said, "i hope you now understand just what you have gotten yourself into." She nodded and I accepted this as a yes. We looked at the microwave and it read 7:25 to go. Her eyes widened and she began sobbing again. I rummaged around the kitchen and found some of those clips used to close chip bags. I chose the smallest two and showed them to her and then clipped one to each nipple which began another round of squeals and cries. As the timer ticked down, I watched she shudder uncontrollably with the overwhelming sensations.

I stood before her and loosed my erection from my pants and held it just out of the reach over her gagged mouth. She leaned forward, as though to suck it and I slapped her twice, quickly, and she leaned back. I removed the bra holding in her panties though left the panties there. I began to slowly stoke my cock inches from her face and she realized what was about to happen and tried to turn her head. Two more slaps corrected her and she faced forward, tears continuing to stream. I watched the clock and timed my release with the beeping of the microwave, spurt after spurt hitting her face, her hair, dripping down to her aching chest. Her sobs only served to turn me on further and I decided to continue to stroke until a second ejaculation burst forth, continuing to cover her face as she sobbed. I used her hair to clean off my cock and closed my pants again. "Stand up." She complied, though could barely stand on her own. I brushed the rice embedded into her skin off to the sound of her yelps. I snipped the zip tie and said, "Wait here." I returned with a bath towel and led her to the TV room. I laid the towel on the floor in front of the couch and pointed to it. She understood immediately. The look of defeat on her face was precious. Her bruised breasts and bottom ached, her knees throbbed. She knelt on all fours with her back straight. I went to the kitchen and returned with a glass of whisky, a bowl of chips, and a jar of salsa. I placed each on her back and she understood that she was to remain as still as possible. I flicked on the TV and fired up Netflix, saying "Oooooh, I have been wanting to see Interstellar again. If I recall, it's quite the long film." The last thing I did before sitting down was take the blindfold from my pocket and cover her eyes as she sobbed quietly. I sat on the couch and sipped my whisky then rested my feet on her back. I glanced at the clock and it read 10:14 and I said aloud, "6 hours and 46 minutes to go, slut. You may have bitten off more than you can chew for your first day of punishment." I put on the wireless headphones and settled in to enjoy the movie leaving her to sob in darkness and silence, my cum dripping from her face and body onto the towel.

Time passes. I watch the movie, have some lunch, she eventually stops sobbing and stoically plays the role of my footrest and table as the remaining cum dries on her. The movie finishes, I take the items still remaining on her back, and bring them to the kitchen. I take the chip clips off her nipples and she yelps twice like a puppy so that's what I say, "Good doggy." She whimpers.

Still in her skirt, shoes, and socks, I beckon her to the balcony at the back of their house. It has solid walls so as long as she is not standing no one will be the wiser. I motion for her to kneel beside one of the lounge chairs and I take a pack of Djarum Black cigarettes from my pocket. I close the door so no smoke gets into the house and I light one up with a lighter. I take a few puffs and admire the view-the city spread out before me and the slut in front of me. As the ash grows longer, she catches on to what may soon happen and her eyes widen. I smile. "Put your head back, open your mouth, and stick out your tongue." She hesitates and I just look at her. She swallows and she complies. I tap the ash on to her tongue and tell her to swallow. I continue you smoking, slowly, tapping my ash, her acting as my ashtray. I balance the cigarette on her tongue and slip into the house to get a fancy beer then retrieve it before it falls off of her tongue. Puff, tap. Puff puff, tap. Finally, it has burned close to the filter and I say, "tongue up and try to make some more saliva. It helps. I also spit several times into her mouth and under her tongue until there is a small pool of our mixed saliva. I stub the cigarette out under her tongue and leave the butt in her mouth. "Swallow it. Chewing it first is recommended. Show me when you are done." It takes her a while, eyes squeezed shut at times, but she eventually shows me her slightly grey tongue. "Lift your tongue." There is but a small spot underneath where I stubbed out the cigarette. I drink my beer and light another. I again use her as my ashtray though I also lightly caress her nipples, already quite sore, with the cherry red end of the cigarette and she flinches but does not cry out, lest the neighbors hear. I finish the same way and she consumes the second butt. I finish my beer and lead her into the house and back to the living room.

"It is almost junior prom time, isn't it?" She nods, unsure of my intentions. "Does your daughter have a dress yes?" She nods, stammering, "Y-yes Sir." I smile, "show it to me, please." She departs and returns with a typical dress in satin and bows and frills in a pale blue. "It will highlight her good looks, won't it?" She nods, clearly uncomfortable with this line of conversation. I caress the dress and then say, "Lay it down in the middle of the floor." She swallows and places the dress on the pristine white carpet. "Remove the rest of your clothes," I command. I go to the kitchen and return with Saran wrap. Without any explanation, I place her arms at her sides and begin wrapping her from the neck down, being careful to leave her long perky though rather sore nipples exposed and poking out of the plastic. I wrap over her hands and around her waist and then pull her to the place where the dress lies and have her lay down on it so that her head is at the waist with the bodice extending to one side and the skirt extending to the other. I continue to wrap her, working my way down her legs until she is a well wrapped specimen from neck to toes and laying with her head on the pretty dress.

I tweak her nipples a few times then take a TENS unit from my pocket. It's a small portable one that is labeled with different sensations-buzz, throb, spikes, sizzle. I've tried it on myself though not in so sensitive an area. Rather than ending in clamps, the wires running from it end in bare copper wire. Placing the exposed wire at the base of her nipple, I carefully wrap it with the supple wire poking the very end into the tip of her nipple. I watch her wince though there is nothing that she can do. I repeat this with the other nipple watching her reaction again and smiling. Next I part the cling wrap at her hips and poke one of those vibrators that looks like a tooth brush through the plastic and between her legs, wiggling it until I guesstimate the location of her clit. I turn it on to test it and she gasps and her hips begin to buck and writhe. "I guess that is the spot, eh?" I turn it off and get my roll of tape. "This tape is great. Very secure though it does not stick to or mar the skin. Close your mouth." She does and I place a long pieces of tape across her lips. The tape is thin and you can see the outline of her pouting lips. I then spend the next hour or so alternating among the different settings on the TENS unit and the different speeds of the vibrator on her clit. It's impossible to say if or how much she came in that time. By the end of it, her eyes were wild though she had not cried, lest she drip on the dress beneath her head. I gave her one last, intense jolt which lifted her off the ground then removed the copper wire and the vibrator.

"One more trial to endure, my pet. Perhaps this is a good time to talk, too. When we discussed this punishment, I think you were feeling particularly guilty so you suggested thirty sessions. Now, since this was a longer one and I know that will be the exception rather than the rule, I will count it as two. Your homework is to decide whether or not you want to continue. I am and will push at and in some cases past your soft limits though I won't go near your hard limits, even to threaten you with them, because that would be unethical." I pause, she nods through her haze of overstimulation. "So, think about it, and let me know if I should come on Wednesday morning. In the meantime, I have homework for you. You are to touch yourself five times every day with at least one hour between finishing one session and starting the next one. Each time, using whatever means you deem appropriate, you are to get as close to orgasm as possible without orgasming. If you do orgasm, I imagine that you will feel rather bad about it and you will have to start again from one. By the fifth time, you should be a hair's breadth away from orgasm and each day I want to push yourself closer and closer. For each session, think of that number-1, 2, 3, 4, and 5. Do you understand?" Again, a nod through the haze. "After I leave, you will send me an email from the special account you created reviewing all that I have just said so that I am sure that you understand." A third nod.

I take the tape from her mouth and she works her jaw a little to unstiffen it. "Now, your last trial. Lift your head." As she does, I slip an open mouth gag into her mouth and buckle it behind her head. This gag has a short rubber tube that extends a little way into the mouth and about an inch outside the gag. This tube happens to fit the mouth of a gallon water jug perfectly and that is what I then fetched and showed her. It had the bottom cut off so that it resembled a large funnel. I affixed it to the rubber tube and began to unzip my pants. Again, realization dawned on her as I freed my flaccid cock from my boxers and began to urinate into the jug and therefore into her mouth. I noticed the piss start to back up and stopped the flow. "Now, pet, here is your predicament. That piss is going one of two places-down your throat or onto this pretty dress. The choice is yours." She began to breathe quickly through her nose but the level of piss did not change. I resumed my pissing and the level rose and rose-I had saved this most of the day and I had had a few cups of coffee and a beer in that time so it was yellow and acrid. Eventually, the stream stopped and I again used some of her hair to dry myself.

Then I stood back and watched her struggle, all wrapped up in Saran wrap, my urial in her mouth, her tongue holding back the flow. She was remarkably good at keeping still while her mind seemed to work on the problem-could she clean the dress in time, what would drinking piss be like, how did I get myself into this situation? After a while, I produced a nose clip that swimmers and divers use to prevent water from going up their noses. It also does a good job of preventing air from entering and leaving. Her eyes showed her panic as I clipped it on to her nose and stood back. After about 30 seconds, the tipping point came. I saw the surface of the piss jug begin to bubble and sink as she swallowed every last acrid bitter drop down. She then gasped for air through the now empty jug. I carefully removed the dress and placed it back on its hanger, "You chose well, my pet." I carefully undid the gag. She swallowed and breathed deep and then burst out in the tears that she had held back so diligently to protect the dress, "That's right, pet, let it go. You did such a good job thinking of others instead of yourself. I am sure that your family would be proud." Only then did she notice the video camera I had set up while she was blindfolded during the movie, "Ah, yes. I only caught our last phase on digital tape, but now I have it to enjoy later. Perhaps I will have you watch it as well." Her sobbing lessened and I used medical shears to snip off the cling film. She was shuddering as I led her to the bathroom and told her to take a long hot shower.

When she emerged, hair done up in a towel though otherwise nude, she cocked her head. While she was showering, I had set up the portable massage table I had brought with me. "Face down, please." Trembling, not knowing what to expect, she lay face down on the table and I spread the warm lotion from may hands onto her back and gave a slow and thorough massage, back and front, working out all of the kinks, so to speak, that had built up during the course of the day. Her look was one of confusion, bliss, exhaustion, a mix of so many things. After we were done, I brought the table back to the car and returned to the house where she had put on the clothes that I had fetched from her room while she showered. She stammered, "I don't know what to say, Sir." She paused, then continued, "thank you. That was one of the most difficult days of my life and I would do it again in a heartbeat." I smiled, saying, "Think on it, you are still in the throes of your endorphins. Email me later when you email me about your five masturbations for today. That homework starts today." She blushed and nodded, "Yes, Sir. I'll do my best." I nodded, "Yes, you will. You did well today, as I said before. There are things that I had in mind to do though we did not get a chance to. I really wanted to fuck you in the ass." She smiled coyly, "There is always next time, Sir . . ."