Any Time Is A Good Time To Punish A Slave!

I'm back. There were many work issues that came up and some summer fun issues and I was starting to wonder if anyone would notice not much was going on here. I have a decent number of readers, and that goes up when I post, but I was hoping to help some people, entertain some people, open a dialogue and meet some new friends. It was starting to feel like I was not accomplishing much. But Mel and Anonymous let me know there were people out there that were waiting for something more...so....


Why do you punish? For real or contrived misdeeds. As routine maintenance. Because you (both) enjoy it?
Choosing when to punish has been a source of endless enjoyment for me, and my slaves, over the years. The biggest problem has been that most of the slaves I have been fortunate enough to have been involved with; M, S, and K were of such quality and reliability that they rarely gave me an excuse to punish unless they chose to do so. Kayla was much more flawed, the problem was her flaws were so aggravating that it was hard to get in the mood to punish her. This was actually a source of tension between Kayla and me as she thought I should find a way to punish away every transgression and not be affected by them emotionally, but I found it easier said than done because of the nature of her actions. Anyway, though, I will try to relate some of my more memorable experiences. K did have the habit of occasional lateness. Lateness is better if it is occasional because if it is a regular idiosyncrasy of the girl I have noticed they do not appreciate being punished for it! Anyway, once K was meeting me in Manhattan though I would almost always pick her up, this time she was going to be with some friends and said she would meet me and she was almost 3 hours late! It was early in our relationship and though she had already submitted to me we hadn’t gotten much past clothespins, spankings and whips and just started touching on humiliation and servitude. We had been discussing expanding our repertoire and intensifying her slavery and I had been meaning to pick up some new items, but this was back at a time just before everything was so accessible on the internet. Anyway, when K finally arrived I was bored and starving but was worried because I had not heard from her. Once I heard she had just lost track of time and had not planned out her transportation from her friends to our meeting efficiently I grew annoyed. However, when we went to eat and she informed me she was not hungry because she had snacked with her friends I grew angry. After I ate, on our way downtown to a club, I told her we needed to make a stop. When we arrived and she saw it was an adult novelty store she seemed excited at first, but then remembered how angry I was. We went to the counter and a very young and attractive bleached blonde goth girl came over. “Can I help you guys with anything?” She asked.
“Yes.” I answered. I have been thinking about picking up a few items suitable for punishment and realized tonight would be perfect.” I said. The girl laughed a little and said, “Why’s tonight special?”
I looked at K and said,” “Tell her K.”
K looked excited and embarrassed as stared at the girl and said very softly; “I kept him waiting 3 hours tonight for no good reason.”
“Oh.” The girl said. “You’ve been a bad girl. Lucky you! I was sure he was going to get punished, because, like 90% of the couples or men that come in, the men are the one’s getting punished. I started to wonder how sub girls find tough love anymore!” She smiled and I saw K smile, relieved.
“So have you already decided what she is in for?” The goth girl asked.
“I think so.” I answered, but I am open to your suggestions. Just know that she not only kept me waiting for hours but while I was worried and hungry she was snacking with her friends losing track of the time.”
“Oh! Well, I don’t know what you like or what you do so if you give me an idea what you are thinking I can then recommend some products.” She said.
“Okay. You should know that K here can take harsh punishment, in fact so far I have only been fortunate enough to use a leather bullwhip on her back and butt and clothespins on her nipples and it is clear I have barely scratched the surface.” I said.
“I see.” She said, “You know, a bullwhip can be pretty fierce and can damage the skin as much as anything.”
“I know.” I responded, “But neither one of us has a room big and empty enough to swing unfettered. These are New York City apartments after all. Truthfully I’m not skilled enough even if we did. I just fold it over and use it as a short two strand whip. As hard as I can it raises some lovely welts, but it is clear she feels I should be doing much better---or is that worse.” I smiled. The store clerk glanced at K who stood there not saying anything, but then K slighted nodded her head in agreement. At this point I was reminded of the great lingerie store scene in L’Image (The Punishment of Anne) where the clerk accompanies Anne and the guy into the dressing room and she sees the red welts across Anne’s ass. The guy explains that Anne was a bad girl and was punished and the girl reaches out and touches one of the welts. The guy then tells Anne to thank the sales girl for her help and Anne kisses her, and when the girl does not protest, Anne gets to her knees and goes down on the girl. This was a hot scene, and since you may remember that K was more than a willing slave, but was actually bisexual and eventually lived with the girl who would become her young lesbian Mistress, you may be expecting me to write about how we got together with the goth girl, but sadly in real life things do not often go like the best (or fortunately---the worst) that the cinema has to offer! Over all I consider myself so incredibly lucky with the experiences I have had with submissive women that I am not complaining. I am just letting you know K would not be serving the goth sales girl in case you were waiting for that particular scene! Still, what went on was quite interesting….
The goth girl suggested, “Since you use clothespins on her nipples I would suggest you move to nipple clamps. I suggest these adjustable clamps because you can decide exactly how much punishment to dish out.” She held up a pair of screw clamp black tipped adjustable clamps held together by a chain. “The chain allows you to tug on them, or to make her tug on them, and can handle a small amount of weight. If you plan to really tug on them I have to ell you they will only stay in place if they are adjusted really tight.” I was about to say something but she continued, “Also, if you pull off these thick black tips,” which she paused and did to demonstrate, “you expose these,” she continued and showed “alligator clamps---at least that is what many people call them.” She said. “Horribly painful with any pressure and with the ability to make someone scream and to draw blood if adjusted tight enough, these light to moderate clamps become the most terrible!” She finished.
“Have you felt them?” I asked intrigued.
“Only on my finger. We are all encouraged to get to know the different products and I am one of the few who have learned all about the things that for punishment. Some of the salespeople won’t even show customers that you can take the black tips off! You guys seem like you can decide for yourselves.” She said.
“What do you think, K?” I asked.
“I think whatever you choose and however you choose to use it…is fine.”
“We’ll take those. You really seem to know what you are doing. What else do you suggest?”
“Thank you. Since you use a whip, I would suggest something stiffer. Canes and paddles can be very painful.” She said.
“I have seen both in movies. I have to admit I am interested in paddles.” I said.
“We have 3 and none are that heavy or large. I think the owner is worried about liability because the salesman said these can be vicious. He said a lot of dominant people will use them as hard as they can because that is their fantasy, without regard to what the sub might be able to handle, or was hoping for or expecting.”
“I am sure that can happen. Most of us can only go by instinct. There aren’t many ‘how-to’s’ and videos either fake the action, or use people who can obviously handle a brutal exchange for the money.” I said.
“She pointed to 3 paddles in a glass case, ”Least painful, most painful and the one in the middle would, I guess, be in the middle pain wise as well.”
I looked at the three, the first was a thin short board with a handle, the middle was a longer version and the supposedly most painful was a wider version of the middle one with holes in it. They all seemed a little thinner than I expected. “Which do you think?” I asked, turning to K. She did not even pause, but pointed to the most severe and said, “The holes make that one look interesting.”
“You can see I am a lucky guy,” I said. “We’ll take that one.” She pulled it from the case and I took it. It was a little heavier than it looked but only about a quarter inch thick. “I am not sure this will really do what it is supposed to.” I said, then pushed K forward leaning over the glass counter, raised the paddle with one hand and brought it down firmly onto her jean clad ass. She breathed out heavily and said, “I think you will enjoy that one.” As she nervously scanned the area for anyone familiar who might have witnessed that.
“Well, if you think that without a full swing and over your jeans, I suspect you’re right!” I smiled.
The salesgirl looked at me, “I am not sure what you are looking to spend or what you are thinking.” I said, “This is good, but I am looking for one other area.” I considered taking the salesgirl over to the side and keeping my discussion and items private from K to make her anxious and suspenseful, but decided it would be more embarrassing for her to discuss it in front of her. “K is not overly sensitive anally and enjoys anal sex,” As I began I turned to K and she looked down at the floor, her shyness was obviously due to inexperience given how impossible it would be to embarrass her later in our relationship! “I would like a butt plug big enough to remind her she is being punished, and a rubber phallus larger than me to use as well.” The girl walked us over to these items. She pointed to a display of butt plugs and I chose a large one! She brought out a skin colored rubber cock that was fairly large, but clearly not larger than me. “You’ll have to go bigger than that.” K blurted out.
The goth sales girl smiled and said, “I guess he’s not the only lucky one then!” And went into the back and brought out one significantly larger. K took a deep breath when she saw that one and looked down at the floor and nodded her head as I said, “Great. We’ll take it.” As I paid I asked the girl, “Are these clean for use?”
“I wouldn’t trust the dildo or plug without washing them.” She said.
“Is there a place I could do that?” I asked.
The girl looked at me a moment, then pointed to the back. “There’s a bathroom there.”
“Thank you.” I said as I started walking back there. I glanced back at K who was standing next to the counter and as soon as I did she walked over to me and followed me back. Luckily, it was just a single use unisex bathroom so I would not have to sneak K into the Mens Room! I walked into it and held the door open and K immediately followed me inside. “Lower your pants.” I commanded.
She lowered her tight jeans somehow managing to keep her panties in place. I gave a quick hard tug to her blonde hair and moved my face an inch from hers “Do you really think I want your panties up?” I asked.
“Sorry Master.” She lowered them as well and I thrust two fingers between her legs. “Your pussy is soaked!” I said as I spread the fingers and stuck one in her mouth as I brought my face to hers again and licked her juices from my other finger. Then I pulled out the large butt plug, squirted soap from the dispenser on it and began to wash it at the sink. After it was clean and dry I told K to spread her legs and then I worked the plug into her pussy. Soon enough it was slick from her juice and I pulled it out and told her to turn around, bend over and spread her cheeks. K did as she was told and K had an asshole every bit as tight as M’s, but anal sex and punishment did not seem to hurt K as it did M. Also, because of K’s complete submission she did not even hesitate though I knew she had never had anything as big as this plug---at its widest point---inserted into her before. It took a lot of effort and manipulation to work that big fat plug all the way into K’s asshole, and her grunts and deep breaths, which was often the only outward signs she was suffering from her punishments, told me the big plug was doing its job and punishing my thoughtless slave. Once it was all the way in, I said, “Pull your panties up and get your skirt over your ass bitch, unless you want me to parade you out there half naked so everyone can see what a punished whore you are!” I barked.
She quickly rearranged her clothes. Then I pulled out the clamps, and pulled the black tips off exposing the shiny metal teeth of those vicious clamps. “The torture these jagged teeth will bring your nipples, like the agony you will feel from your new paddle, are all for when we go home later.” I put the black caps over the teeth again. K looked relieved but it was short lived when I told her to raise her shirt and to take off her bra as she would not need it or want it for the remainder of the evening. I clamped a clamp on each nipple and then began tightening them not stopping the adjustment to each nipple until the contortions of K’s face told me she was appreciating just how severe nipple torture could be. I told her to lower her shirt. As soon as she did, she looked down at her chest and began to protest, “Everyone will see what I have going on under my shirt Master. The outline is clearly visible.”
“No slave, they will simply know something s going on under you shirt but they won’t know what it is. However, in order to punish you further, and protect your nipples from damage due to prolonged clamping, we will take the clamps off every 15 minutes, leave them off for 5 minutes, and then replace them. If you are unfortunate, this might need to be done when we happen to be outside somewhere, or perhaps right on the dance floor of the club.” K looked at me, and I could tell she was wondering if I would really do it. “Now raise your shirt again and get on your knees on the floor.” K did as she was told, and I reached down and grabbed the chain of the clamps and pulled hard. She cried out, surprised by the level of pain and then I looked down at her and told her to open my pants. She did so, and then she lowered them and freed my cock. “Suck me off slave!” K was a fairly good cocksucker and I was very excited and motivated to cum quickly and move on with our night. The way she sucked while using her hands to massage my balls, at the same time knowing the punishment I was inflicting pulling so hard on her clamps, I nearly fell over when my cock exploded in her mouth but she suckled me deeply into her throat and barely paused as she swallowed every drop.
I never actually made her lift her shirt in public, and the repeated acts of removing then replacing the nipple clamps was an fine a punishment as I’d hoped. From the first time the clamps were removed K’s nipples were so sore and sensitive that by the end just touching her nipples with the clamps caused them agony, and the exquisitely anguished reaction I got when they snapped back on to her swollen nipples was lovely. It was an exciting couple of hours of dancing, though strangely, K was moving in a much more restricted manner than usual. Several times I would pull her tight against me by grabbing her ass and pulling her into me hard. I would get a grimace or moan that was barely audible above the music though she was so close.
“Anything wrong slave?” I asked.
“No Master.” She replied.
“You dance and act like a bitch whose tits and ass hurt.” I smiled.
“No Master. I dance and act like a slave bitch who kept her Master waiting, though I know I should be punished more and suffer much more than this. I hope you will take care of that when we go home.”
“You saw the paddle, whore, and you saw what those clamps are like with those terrible teeth exposed! In fact, I cannot imagine how it will feel to have those little biting teeth on nipples that have been so tortured for hours already!”
“I deserve to find out Master.” K responded. K had the highest pain tolerance of any slave I have personally known. M could take almost as much but it was clearly a strain for M and K always seemed like she could, if I really desired, be pushed a little bit further. After this conversation I was really in the mood to punish K and fuck her too, so I led her off the dance floor and we left the club and went to my car.
On the way home I decided it was time to up the ante as we had discussed. Usually, though she took a harsh punishment, and would handle humiliating tasks such as playing with her asshole or licking my cum out of a dog bowl, we were still starting off as boyfriend-girlfriend, making out, undressing each other, and then moving into D/s if the point came up organically. Now, since she was already being punished, already sucked me off, and was expecting more when we got home, I decided we would proceed a bit differently. In the back seat was a black overnight bag I carried around filled with assorted S&M gear for when our dates moved in that direction. I told her to reach into the back seat and retrieve the bag and put it on her lap. After she did so I told her to open it and find her slave collar. It was a thick black leather collar, about 2 ½ inches wide with some studs on it and a big O-ring in the front. She found the collar and a black leather and steel chained leash was still attached from our last go round. She unhooked it and then looked over at me driving. I reached out my hand, “You can give that to me, and put on your collar.” She did not protest that she might be seen, just put it on. Though she worried about the nipple clamps being visible, K was not overly concerned about public displays, maybe more about being displayed in front of a disapproving or inappropriate public. In fact, a little later in our relationship she would bring me down to a famous S&M club in the city, the first time to celebrate an occasion, where she arranged 2 female dominant club patrons to punish and humiliate her for my entertainment. This turned out to be a prelude to her introducing the fact that her on again-- off again young apartment mate was also her occasional (soon to be more permanent) lesbian Mistress. (That, as you know, are many other stories!)
Anyway, I told her that as soon as we entered her apartment she should strip until she only wore the collar, the nipple clamps and the butt plug up her ass and then kneel and await my next instructions.
“Can I pee first, sir?” K asked.
“Sure, but make sure you don’t let the butt plug drop into the toilet or you’ll end up playing bobbing for butt plugs with your face in that bowl, understand?”
“Yes Master, I understand.”
We went in and just a couple of minutes later she was ready and waiting, kneeling naked on the floor. The nipples clamps, removed and replaced about 13 times were hanging from her nipples, the plug was deep up her ass, protruding a little bit from between her cheeks. She was looking down at the floor and had her hands clasped behind her back. I reached down and grabbed her chin and raised her face so she was looking into my eyes.
“Beautiful K,” I began and leaned in to give her a light kiss on those luscious lips, “You’ve been very naughty tonight, and I am afraid your ass and tits have only just begun paying for it.” Then I reached out and pulled the clamps from her nipples. She cried out as she had done during the last six or so removals. I slowly rem0oved the black caps from the end of the clamps and exposed the vicious little teeth of each. “How do you think these will feel, bitch?”
“Master, it has been agony each time you put the clamps back on and I know those clamps will teach me a new lesson in pain. Surely I will barely be able to contain myself, so please, ignore my pain and my pleas and punish me for as long as you see fit.”
“You do have a good attitude slave. Stand up!”
She stood up and I motioned for her to turn around.”
“Bend over whore, and let’s see what we will do to your ass before I get back to your nipples.” I slowly pulled the large butt plug from her asshole. It seemed clean as I brought ti around to her face and demanded; “Lick it clean, bitch!” After a little licking I shoved it into her mouth and told her; “Keep it in there and stay bent over while I paddle you 25 strokes. If it drops out of your mouth or you move out of position you get another 25 strokes!” The plug barely fit halfway into her mouth so it was very possible it would fall out and usually I tie K down for severe punishment so it was anybody’s guess whether she could remain in this position for a paddling--- but then, after keeping me waiting for 3 hours, those were risks that I, and my slave’s ass, were prepared to take!
I got the new paddle and swung it in the air a couple of times. “You know, slave, I think if I swing this hard enough it is really going to hurt your naked ass!”
I was sure she would want to say something to that but only moaned with her mouth filled, so I pulled the plug out of her mouth and she said: “I know we are both counting on that Master.”
“Yes,.” I agreed as I thrust the plug back in K’s mouth.
I stood behind K and raised the paddle. Though I did not plan to use as much force as I could, I had also decided not to start by going easy. My first stroke was a pretty forceful blow. She shook a little and moaned but did not break position or drop the plug. I rubbed the paddle across her ass and then raised it again. When I lifted it from her skin I saw she immediately tensed up awaiting the next blow. I waited several seconds then brought the paddle down much harder this time. She squealed a bit from behind the plug but again did not drop the plug or break her position. Now I kind of wanted to see her drop that plug, or break her position, anything to earn the extra punishment! I knew K could take a lot of severe punishment, but it did not mean she could do it without moving or crying out if it.
“Slave, I think I am being entirely too easy on you after the way you disregarded your Master.” I looked at her and she drew in a deep breath and then nodded her head in agreement. I raised the paddle, and then brought it down as hard as I could, then raised the paddle and immediately brought it down as hard as I could again, then raised it again, and repeated this sequence for 17 more fierce strokes before she finally cried out, dropped the plug and fell forward out of position. She quickly tried to pick the plug up with her mouth, but could not, then took it with her hand, turned, crawled over to me and started to kiss my feet while saying, “I’m sorry Master, I’m sorry, this slave bitch deserves to be punished terribly for her behavior and for her performance during her punishment.”
“You will be slave, you have earned another 25 strokes after I complete the last 6 strokes, though I have to say you broke position and dropped the plug and I should really give you another 50 strokes for that!” I smiled to myself as that was not really my intention when I gave her the rules but I wanted to scare her a bit.
“I know Master, I know I have earned another full 50 strokes, and you should deliver them all hard and fast like those last strokes, giving me no respite and showing me no mercy for the disappointment and aggravation I have given you tonight.”
We were just beginning to see glimpses of the incredible limits of this slave!
“Slave, if I do that you won’t be able to sit for a week!” I said looking down at her.
“I can always sit Master, it is just how much it will hurt when I do. Each sting I feel everyday will help to remind me of what a bad slave I was today, and what a wonderful Master I have to teach me to be more obedient.”
“I am sure you are correct slave. You have earned a severe paddling.” I know there are dominants out there thinking that my slaves often ‘top’ from the ‘bottom’ and I will not argue the point that I do indeed let slaves lead me to how much punishment they will receive. Slaves are human and their limits are fluid and I have no problem allowing me to understand what they can and cannot take in that moment.
“Master, I know you are too compassionate to point out that it has been more than 5 minutes. I know you would wait until one punishment is finished before subjecting your slave to the other severe pain, but this bitch understands she has earned this treatment and you should not wait until after my ass is beaten to put those terrible biting clamps on this slave bitch’s nipples for the rest of the punishment, this cunt whore will take her punishment the way she should.”
I had not planned on doing that both because I felt it would be too much pain at once and also because I like my slave’s to be able to focus on whatever sensations I choose at that moment, but the reality was both these punishments were so severe that I was not afraid one would “detract” from the other. My concern here was that it would be too much for her, but K clearly wanted to try to endure both at once so I decided to let her, and I would be the judge if it was too much and needed to be adjusted.
“You’re right bitch, you have earned this and you shall get it. Stand up. As she did so I brought over a chair. “Sit down.” I did not think her legs would hold her up if she were standing when the clamps were applied, and I wanted to be able to more easily reach her breasts to apply the clamps then I could have if she was kneeling. I tied her hands behind her back and brought over the clamps. I had them in front of her face and opened and closed them. “The last adjustment to them had made them very tight slave, and I have not loosened them since. With their teeth bared now, I expect the pain will be terrible, and each second will drag on giving you ample opportunity to think about how you will never treat your Master this way again, as well as how hard you are going to try to make it up to your Master when he uses his whore after the punishment is finished.”
“Master, I will use this slave’s mouth, asshole, pussy and hands to please you once you have finished torturing this slave for her terrible behavior.”
I nodded as I reached between her legs and rubbed her pussy. I knew she would be wet but she was much more soaking wet than I expected. At this point I already knew K loved to talk about being tortured and used but combining that with some of the most severe treatment we had experienced together was really very successful! I squeezed her right breast in my hands jutting out her small, pink abused and swollen nipple. I squeeze the other clamp open with my other hand and put it over that nipple. I looked into her eyes as I released the clamp and let it snap shut, biting into her nipple. Immediately her eyes screwed tightly shut and she gritted her teeth and squealed out as tears began to work their way out. I was about to reconsider using these clamps when she said: “Thank you Master. This slave deserves her punishment. You were right to put these clamps on before my paddling was finished!” So instead of reconsidering I took the other clamp and snapped it onto her other nipple. The squeal was louder and tears rolled down her cheeks, but all she said was; “Thank you Master for hurting my nipples and punishing your slave bitch so severely. “
“You’re welcome slave. Bend back over so I can finish your paddling. My cock is throbbing and it’s getting to be time to use you for other things than punishment.” When she bent over I looked at the thin silver chain hanging from her nipple clamps and could not resist giving it a tug. She cried out from the quick jolt of pain.
“Those seem very effective slave, maybe I should leave them on and use them for a leash for the evening?”
“Whatever you desire Master. I am sure that would teach me things about pain I don’t know!”
“Possibly slave. As good an idea as it is though, I don’t want to leave the clamps on that long. In fact, we need to finish up your paddling so I can remove the clamps and use your mouth for something besides screaming.”
I took the paddle and moved behind slave K. 56 strokes to go slave, fast and hard as I can. You will know what it is like to get punished after this!” As I was getting ready I was debating in my head whether to not make the strokes as hard as I could, or to not plan on doing all 56, because I did not believe K, even with her prodigious pain tolerance, could necessarily handle this punishment as much as she seemed to desire it. And even so it was not clear to me the skin of her ass could take it, and I was not looking to severely damage her. I knew I would be looking at a very bruised ass for days if not weeks if I even came close to finishing this punishment the way it began. Each step of the way it was clear K was looking for this level of punishment but I was very interested to see what she would think of it over the next few days as she saw how sore her nipples and ass would be, and I was not done using the plug and large dildo we bought for her asshole yet either! I decided if I tried to cut the number of strokes K’s pride would force her to request the entire punishment. I could not be sure at that time, but things I had seen later on from her and M made me believe that assessment was correct. I decided I would just not give it the amount of force I had started with. Her ass was already so sore I did not think she would notice. I raised the paddle and started giving her the strokes, one after the other , after the first six I realized I did not want to have to worry about counting.
“Slave, you will count out the next 50 strokes.”
“Yes Master.”
I started the paddling again and she counted out the 50 strokes. I did not realize she was crying, but the tears were running down her cheeks and I decided I should have done an easier paddling and less strokes!“Slave, if it was that bad you should have asked for mercy.”
“I did not want mercy Master. I wanted to experience the full punishment.”
“I understand slave, but it was obviously very painful and sometimes it is exciting to hear my slave beg for mercy.”
“I am sure you will have plenty of opportunity to hear me beg for mercy when you torture my asshole Master, but please remember that just because a slave begs for mercy does not mean her Master has to grant it.”
“I am well aware of that slave. Your behavior tonight has not put me in the mood to be merciful, but you have been very accepting of your punishment so I can see you want to make up for that earlier crap you put me through. Now, before we move on to your anal punishment and then my fucking you for the rest of the night, I need to remove those clamps. After all this time and how sore and swollen your nipples already were, I can imagine the pain would be incredible removing any set of clamps, but I cannot fathom how much agony it will be to have those terrible teeth let loose their grip as these clamps are released. Now stand in front of me and put your hands behind your back and get ready….”
I grabbed both clamps and squeezed their release points at the same time. Immediately K gave a half scram and fell down to her knees, her eyes closed and tears again streaming from them.
“Thank you Master for punishing this slave bitch the way she really deserved.” K said still kneeling on the floor.
“I’m not done yet slave.” I said looking at her so lovely, kneeling there naked.
“I know Master,” K said as she stood up and pressed her naked body against me and grabbed my hand and brought it between her legs. She pushed my fingers against her pussy and as my fingertips slipped between her lips I found she was soaking wet, “I’m counting on the rest of my punishment.” K whispered into my ear. I pulled my fingers from her pussy and licked them.
“Your pussy tastes delicious slave.”
“Thank you Master, and I also know that because you have me lick my pussy off so many things!” She smiled.
“I do seem to like watching a slave taste their pussy and ass, don’t I?”
“Yes Master, we both like it very much!”
I had K bend over the end of her bed; as soon as she leaned on her nipples she moaned and mentioned how much they hurt. I pulled her hands behind her back and tied them that way which put even more pressure on her breasts. I kneeled down behind her and said, “We need that asshole nice and wet.” and then buried my face between those firm, smooth cheeks! I tongued her asshole and worked my tongue in deep until it was nice and slippery and then I stood up, rubbing my cock through my pants. I leaned in against her rubbing myself through my pants against her naked ass, pushing the bulge of my cock between her cheeks.
“Master, if you need to fuck me to relieve yourself maybe you should. I would not want you to rush my punishment because you are too anxious to cum!”
“Thank you for your concern slave, but I will try not to rush. I prefer to keep letting it build as long as I can and if I suddenly just fuck you it will be because I could not wait to fuck you any longer not because I rushed your punishment.”
“Yes sir.”
I took the large rubber cock and started to rub its big head between her cheeks against her asshole. K moaned and wiggled her ass. “I need some lubrication whore!” I barked as I quickly thrust the cock into her pussy from behind. She moaned as her pussy took in inch after inch. I harshly fucker with the rubber cock until it slid easily in and out and glistened with her juices, then I pulled it out and began to push the head insistently into her asshole. She leaned forward grinding her sore nipples harder into her mattress and relaxed her cheeks and ass as best she could as I began to push the cock head up her asshole. She groaned and sighed heavily into the blanket as I drove the huge cock deeper. I did not realize how big the cock was until I watched her asshole tightly stretched around it. I was using both hands to guide it in but let it go with my right hand to reach underneath and massage her clitoris, occasionally working my fingers into her pussy which was managing to stay pretty wet throughout her entire punishment that evening! I used both hands on the dildo again and finally worked the whole huge phallus up her ass and she was moaning, groaning, and gasping when I started to pull it out most of the length, then drove it back in hard and fast, then pulled it out and drove it back in harshly as I roughly fucked her tight asshole with that humongous rubber cock!
“Oh lord Master, that cock is so hard and big, it hurts so much to be anally abused like this Master, please have mercy on your slave bitch’s tortured asshole Master, please !”
“Do you think a slave who keeps her Master waiting for hours deserves mercy, slut?”
“Master, that cock is so big---Master---ow---oh Master, I know your right, but it’s so big and hard, but no, no Master, of course not, show this bitch no mercy, rape my asshole, make me scream and finish my punishment please Master!” K was very good at improvising what to say during these times! She loved to talk submissively, talk about her terrible tortures and beg for mercy more easily and uninhibited than just about any other submissive I have known.
Finally, after another 10 minutes of abusing K’s asshole, I pushed it in as deep up her ass as the dildo would go, then I got undressed and started fucking her hot, wet pussy from behind. I untied her hands and told her she could touch her pussy if she liked, but to make sure she came when I came. It did not take long and the simultaneous orgasm was explosive and draining. After it subsided I told her to remove the dildo from her asshole and she did so slowly and gingerly. She told me she could not remember her asshole ever so sore and I told her she had until I was hard again to rest it up because next I would be fucking her ass and cumming in her mouth. I thought she would take this as a threat and beg for me to just use her mouth, but instead she smiled at me when I said this, then she said, “Master, I don’t need to rest my well punished asshole. I wish you could fuck it right now. While it is sore it will remind me of why I deserved to be punished. I’m sure if you put me over your knee and spank my well beaten ass and then I give you a tongue bath that ends with my tongue deep up your ass we can get your cock rock hard in no time!”
Another time I remember punishing a girl right at the moment of an infraction included slave M and a walk in a secluded area of a park. Although it did not really happen at the time of the infraction, it happened as soon as we discussed the event and M acknowledged her poor behavior. The event actually happened on a Friday night where M and I were meeting at a club. In this case M was arriving with some friends and one of them lived near her so was going to take her home, and I was coming with a new business associate and his girlfriend. I wanted them to meet M so we were going to hang out at the club a while, then go to dinner, then I would bring M back to the club and she would go home with her friends and then I would meet up with her Saturday afternoon and we would spend the rest of the weekend together. In fact M had already planned that we would go to a park Saturday afternoon, but we’ll get to that. Back that night at the club, when I got there with my colleague the place was jammed! Wall to wall with people! His girlfriend, like M, was supposed to meet us at 7PM. His girlfriend was on time but M was late, which was very unusual for her. Time dragged on and I started to get worried but could not reach her. The club was very loud so I kept checking my phone in case she called because I was afraid I would not hear the ring, and maybe not even feel the vibration. By a bit after 8PM I had to go to the bathroom, and it was murder making my way all the way to the back of this place to get to the bathroom. When I finally work my way to the back who do you think I find talking with friends? M. I walk over to her and she hugs me and kisses me and introduces me. I was very nice but told her I need to speak with her. We go to the side and I ask her what she was thinking? She said we were to meet at the club but we never discussed where to meet and she got there about 6:30m with her friends. I told her I did not want to discuss this now, and dragged her up front to meet my friends. We went back to her friends and said we would leave for dinner and I would get her back in a couple of hours, which I did. That was the end of it for the night
M often took me to large parks that had a lot of secluded trails that she liked to explore during weekdays and off hours because M also liked to try to get an opportunity to have sex outside. We have had sex under busy boardwalk restaurants, in many parks and in our cars parked in various quiet areas. When the event I just discussed occurred, much like the event described above with K, it was earlier in our relationship, but after we acknowledged D/s would be a big part of our relationship. So that Saturday later in the afternoon I found myself on the way to one of these parks. M was all over me as soon as I got to her apartment and I knew she was horny because we did not spend Friday night together as we often would at that time. M had a very high sex drive, perfectly mated to my own, and sex was never one of the issues that came between us when we had a relationship. Anyway, M greeted me wearing a medium length skirt and a thin tee shirt. As our hands roamed over each other I found she was not wearing any panties, but she stopped short of having sex and instead she said we should get going as it was getting late to go to the park. I knew this meant the park was probably one where she expected we could do what she wanted. On the drive there I brought up the night before. I pointed out that while it was true that we did not discuss a spot to meet, when the club was so crowded was it reasonable to assume I would know to go to the back, or even necessarily find her back there? Also, if it was too loud to hear her phone shouldn’t she have checked it occasionally? And why did she not try to reach or find me as it got later and later? She admitted she did not handle it well and was so involved with her friends she was not thinking and apologized for treating me that way. (It must seem like K and M treated me pretty shabbily when it is related like this, but this was over years and the fact is they were both excellent girlfriends who were very attentive and giving---it was not easy to recall such events because of the high quality women they were!) Then she said; “I’ve been a very bad girlfriend. I’m sorry…sir…I deserve to be punished for that.”
“I agree.” I said.
“When we get home tonight you should be very hard on me. Do whatever you feel you need to and whatever you feel I deserve. I will take everything and then do my best to make it up to you.” She smiled then leaned over in the car and rubbed between my legs.
“I see. Sounds good, I will definitely punish you tonight and I have no doubt you’ll make it up to me since you do such an amazing job in bed even when you have nothing to make up for!” I smiled too. When we arrived at the park I let M lead the way. We enjoyed the sights for a while; the plants, flowers and trees and then we played a little Frisbee. Then M said we should walk along a trail. We did so, and it was a steep trail that wound up hill for over a mile. When we went up more than half way we had not seen another person on the trail, and then we stepped off the trail down a dirt road into the woods. Through the woods we came to a clearing with a great big boulder with a smaller rock to its side. I sat down on the smaller rock and M sat on my lap and started to kiss me. I gave her a nudge and she climbed off my lap and stood in front of me.
“Raise your skirt.” I commanded. She lifted it, showing her beautiful trimmed pussy. “Turn around.” I demanded and she turned showing me her beautiful, firm, round ass. “Turn back.” I aid and she faced me again. I reached out and rubbed my hand between her legs. She moaned and spread her legs a little and I found her pussy was soaking wet. “I see you want to get fucked even though we plan to fuck all night. “ I said. She looked at me with a hungry look and then nodded her head in agreement.
“I assume you expect to be punished now also even though you expect to be punished severely tonight?” As soon as I finished M looked apprehensive and nervously started to turn her head and scan the environment. She was obviously much more embarrassed with the idea of getting caught being punished then she was being caught getting fucked! Finally she nodded her head in agreement once again.
“Over my lap.” I commanded. She continued to hold her skirt and lay over my lap and I began to spank her, not very hard at first, but soon it was hard and fast. A couple of times she started to reach back as if to protect her ass from the blows but immediately stopped herself and brought her arms back in front of her. Finally, when her ass was very pink, I nudged her off my lap. She stood in front of me again, and then immediately turned so I could see her pink ass.
“I am not looking to be too severe now as I plan on being very severe tonight tonight, but your ass does not seem red enough. Do you have any ideas?”
“You could wait until tonight and make it so red I can’t sit down!” She offered smiling.
“Oh, I will do that tonight, but I do not plan on waiting!”
“I thought not.” She said. “You are wearing a belt, or you could look for a stick to use as a switch I suppose.”
“I think a switch would be too severe for now. Kneel in front of me and take off my belt.” She knelt in front of me and then opened my belt and slipped it out of the loops. I opened my pants as she finished this and said, “While you are down there….” And pulled my cock out and she leaned forward and kissed the head of my cock then started to suck it. Too soon I felt like I could explode in her mouth so I pulled out and told her to lean forward over the big boulder. She leaned forward, her skirt pulled up and I doubled the belt into a big loop and started whipping her ass with it. I gave her about 20 strokes and then got right behind her and started to work my cock into her pussy from behind. As I expected her pussy was still soaked from all our action. It did not take her long to cum, and then I started to cum before her orgasm had subsided. We got our clothes straightened out and decided to walk back down the path to get to our car and finish our planned punishment and fucking as soon as possible. When we talked later apparently M planned on a long leisurely dinner before we went back home, but our time at the park only made us both want more, and it wasn’t until very late that night, when it seemed unfair to expect her ass to take much more punishment, that we finally decided to go out and get a bite to eat!
Anyone have any thoughts or comments about when and where and why and how they punish?