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Review This Story || Author: Jack Harlequin


Part 1

I opened the door to her cell and let myself in, closing the privacy curtain behind me. She was sitting on the single bed against the wall. With the exception of the handcuffs on her wrists in front of her, she was completely nude. I always prefer the girl to be nude and handcuffed on our first meeting. It makes her feel vulnerable and completely available. It makes her very afraid and very easy to connect with on a very deep basis. I think they feel that if they connect with me, I will have more feelings for them, and therefore I will be perhaps a little more gentle with them. They are wrong about this, but I want them to make that assumption. It makes the energy delicious to my taste when we meet.

At our first meeting, every girl sits in exactly the same way. This girl is named Melissa, and she is no exception. Her cuffed hands and forearms are together in front of her breasts, trying to cover them up. She is leaning forward with her legs tightly together in an effort to conceal her pubic area, and keep some vestige of modesty. I am excited every time I see them in this position. Taking them out of this position, fully exposing their nakedness, and making them fully vulnerable and available, is the very first step of breaking them down. If you are a sadist like I am, it is very enjoyable.

She looks in my direction as I close the privacy curtain. Her eyes however, are not drawn to my face. Her eyes only look at my face for a moment. Rather, they are drawn to the wooden paddle I am holding in my hand. Its not a large paddle. Its only 18 inches long and 3 inches wide. But shes seen the videos during her orientation with a Matron the day before, and she knows that it will do a wonderful job, creating horrible black and blue bruises on her ass, and that she will blubber like a baby and beg me to stop, while she receives the loving attention it can provide. Her eyes are glued to it, while I lay it on the table in the cell. The table is three feet long, and has straps on the top and on the legs. When she bends over it to be paddled or fucked, I or anyone else in my position, will have the option to strap her legs and, as she bends over, her back to it, securing her completely to the table, in order to punish or, since her rectum and vagina will be completely exposed and vulnerable, fuck her as enthusiastically as we choose to in either of those 2 holes, without her interference. Already waiting for me on the table is a box of latex gloves and a jar of flavored, water based lubricant, both of which are self-explanatory.

I casually sit down on the bed next to her. I put my arm partially around her back and gently rub the center of her back, between her shoulder blades. Because she is leaning forward to protect her modesty, it is only natural for me to touch her open back and caress it affectionately. I feel her tense slightly as I touch her. I would have remarked at this, but I am overwhelmed by the beauty and softness of her skin as I sit next to her. Her skin is that milky white, almost porcelain expression of perfection, and incredibly soft to my touch. Her auburn blonde hair, washed and blown out earlier in the morning, hangs down to nearly the same spot between her shoulder blades, and I gently pull on that with great affection also.

She had only been arrested 5 days earlier. Just before her arrest she had made the rather obvious mistake of spurning the advances of the 2 Texas billionaire twin brothers that owned her company. Apparently they had the particular fetish of fucking a girl together, after softening her up with a spanking session that would make her cry and agree to do anything they wanted. She was rather new in their company, and as a very beautiful 25 year old girl, was a wonderful addition to their workforce; so they asked her to lunch with them. After a glass of wine they approached her with the idea of spending the evening them, during which time they would “be able to have an intimate discussion about her future in the company”.

She understood the request for what it was, and told them to go to Hell. She resigned on the spot, and filed a complaint with the Federal government. The New Republic being what it was, dismissed the charge immediately, but the two brothers were furious. They came to me, and I went to her husband and made him an offer he could not refuse, which included money, a divorce in which he got everything, and most important, access to the beautiful girls in our school. Had he refused me, he would have been arrested also. I also promised him that he would still get to fuck his wife, and in many new and kinky ways. He would just have to wait for his turn, which would always be after me, and two particular billionaire brothers whom his wife seemed to have offended. He agreed to everything and gave me an extra key to his wife Melissas car.

As fate would have it, the next day Melissa was pulled over in a routine traffic stop, and the Police Officer asked Melissa to open her trunk, for a routine search. There was a pound of cocaine in the trunk. She was arrested, and since drugs were the destroyer of our culture, Melissa was convicted and sentenced to death, all within a day. In an act of Mercy, rather than execute her, the State placed her into the custody of the School, where she would have no rights, but would be rehabilitated into a new person, until such time as some wealthy man purchased her to be his obedient wife or concubine, with the emphasis on Obedient.

That brought her to this incredibly delicious moment, sitting next to me nude, in her cell, with my hand caressing her back. I had not yet said a word. I was simply enjoying the moment, caressing her back, and feeling her fear. I kissed her on the shoulder, enjoying the feel of her bare skin on my lips, and finally, I said to her in a whisper, “Is there anything you would like to tell me?”

She let out the slightest whimper and said, “Please Sir, I want to be a good girl.”

I brought the hand that had been on her back up to gently grip her shoulder, and brought my other hand to the top of her cuffed hands in front her, that she had been using to attempt to conceal her nakedness, and said, “If you really want to be a good girl Melissa, you should never, ever try to hide your charms from me.” As I said that, I lifted her back by her shoulder, so that she was sitting straight up, and in the same motion brought her hands and arms down away from her chest, completely exposing her tits. I put her cuffed hands in front of her at her waist, and then slowly brought my hand to her knees, separating them until I had an unobstructed view of her tits, her inner thighs, and the lips of her cunt, and said “Always give me a clear view of all of your charms.”

There was no resistance from her at all as I exposed her. I brought my hand up her leg from her knee, lingering on her inner thigh, feeling its exquisite softness, up further, lingering this time at her pussy, gently touching and slightly separating their lips with my finger. My hand continued its casual journey up to her belly, which was completely and perfectly flat, and continued up to her breasts, cupping each of them, one at a time, fondling the nipples, and weighing each breast slowly in my hand. “Dont ever, ever hide any of these charms from me. These belong to me, along with every other part of you.” She whimpered and said, “Im sorry Sir. I didnt realize it. Please dont punish me for it. I wont do it again.”

“Thats not the way you apologize to me when were alone Melissa. Get down on your knees on the floor and kiss my feet, and apologize. Keep apologizing until I tell you its enough.” She dropped to her knees. I was dressed in a Brown robe with a hood and sandals with no socks. She put her face to one of my feet, and began to kiss it, and said repeatedly, “Im sorry Sir.” I told her to use her tongue as she kissed my feet, and slowly her tongue began its life of service, as she introduced it to the top and bottom of my bare feet.

At length I lifted her head up and kept her on her knees. I drew her to me, and she knelt between my legs, as my robe opened, exposing my fully engorged cock. She would soon be sucking it. It would soon be up her ass. It would soon be plowing every hole in her body, to its maximum depth. She stared at it like they all do the first time they see it fully erect. Its 10” long and 2” thick. They always stare at it the first time in fear, asking themselves how that thing will fit all the way up their asses and all the way down their throats, and then they think about how it will hurt when those things are happening. I never tell them that should be the least of their worries, but it always makes me smile.

I take her head in my hands as she kneels before me, and I kiss her on the mouth. I start slowly, as though we are on our first date, which in some respects, we are. With my lips I open her lips, and put my tongue just inside her lips. Her mouth opens more, like an eager girlfriend, and my tongue goes further into her mouth, to be met by her tongue. I realize her tongue is still in a little bit of shock from the foot licking apology she has just given me, and it makes me more aroused as I kiss her. We kiss passionately for perhaps 60 seconds, and I then take her by the arms and have her stand in front of me.

I draw her to me again with her breasts in my face. She is 54” tall and weighs 105 lbs. She has a very slim waist, which I have my hands around, and B- cup breasts, that are perfectly firm, and untouched at this point in her life, by gravity. They are also in my face, as I inhale her lifes essence through them, and kiss them, and taste her nipples in my teeth, as I lightly bight them. As I do this I put my arms around her waist and cup her ass cheeks in my hands. Her ass is perfectly rounded. It is also perfectly white and smooth right now. That is about to change, but for this moment I simply enjoy its feel and softness, while I open her ass cheeks with my hands and put my middle finger deeply, up into her rectum. I can feel her entire body freeze for a moment as my dry finger enters her rectum, and continues up into her.

I have noticed that every girl is different when she begins to have her ass opened. I know that Melissa never took it up the ass from her husband because he told me so. It was a form of sex that he wanted that she refused to consider. I know that Melissa was told the day before by the Matron that even though she has never taken it up the ass before, those days are gone, and she will need to very quickly adjust to having her ass used anytime it is demanded of her, and that it will be frequently demanded. She has seen the instructional videos, and knows that when I am sodomizing her, she will often be lying on her stomach, with a pillow under her hips and her ass up in the air. I will be lying on top of her from behind, with my rather large cock all the way up her ass, as I plow in and out of her. My arms will be around her from behind, in front of her face. She already knows that she will be expected to kiss my arms, and tell me how much it hurts, and that she loves me, repeatedly and continuously until I am finished using her ass.

What she does not know, is that I do not usually finish quickly, especially when its my last sex of the day, and she is in my bed for the night. I am usually already fairly sated, having already had sex 5 or 6 times before that, during the day. At the end of the day I often enjoy plowing a young girls ass for hours. I find that as I plow her ass for a protracted period of time, that as the time goes on, the girls level of surrender gets progressively deeper and more profound. She never resists me. They all know much better than to do that. But for the first 10 or 15 minutes she tries to be brave, and tells me that it hurts and that she loves me, as she kisses my arms. After 15 minutes her sphincter muscles have begun to spasm into the open position. This hurts her even more and she usually runs out of bravery and succumbs to the pain and the stretching of her rectum and the impaling sensation in her lower bowel. She begins to cry, and will continue to cry for the next hour or two, as she overwhelmingly feels both hopeless and helpless. Still she kisses my arms and continues to tell me that it hurts, and that she loves me. She is telling the truth about it hurting.

At some wonderful point during this extended period of crying, she runs out of tears. The pain becomes more bearable and less frightening. By this time she is also exhausted. I can feel her pain and exhaustion. At this point she somehow reaches into herself and surrenders to the moment. She attaches the essence of her soul to me, and when she kisses my arms, and tells me that she loves me, for the first time, she really means it. This complete surrender, and giving of her love, in fear and in pain, raises my level of excitement, and then I am ready to climax in this psychic union inside of her. At this moment I am connected and united with her.

Even though I enjoy the whole process thoroughly, I sometimes wish that I did not have to go through this entire process, to achieve that level of connection with another human being.

Her soon to be ex-husband is very much looking forward to having her this way. He will have to wait until it is his turn. The two billionaire twins that she offended are very much looking forward to having her in this way- together- during which time they will switch positions repeatedly. One of them will always be in her ass, with the other in her mouth or her cunt. They will also have to wait until I have enjoyed her in this way repeatedly. By that time she will be accustomed to the taste of her ass, and having a man withdraw his cock from her ass, to immediately plunge it into her mouth and throat. For now I continue to hold her ass, finger her rectum, and enjoy the taste and smell of her breasts as she meekly stands in front of me, and she has her first real experience of her new life to be, as my property. I spend 5 minutes enjoying this embrace, and then I take my finger out of her ass, and my face out of her tits, and stand up and walk her to the table.

The paddle is waiting.

It is only three steps from her bed to the table, not exactly a long journey. But her legs seem to be failing her as she stands in front of it. They start to tremble and almost buckle. As she stands at the foot of the table, with the edge just touching her upper thighs, I say the six simple words that she is dreading. “Please bend over the table now.”

She stands there for 4 or 5 seconds, blinking her eyes and holding back tears. It almost seems as though she is trying to translate what I had just said to her, and understand that it really means something other than what she thought it means. I stand there next to her, still holding one of her arms, enjoying her anguish. After 5 seconds she seems to realize that delaying any longer could mean an additional penalty for disobedience, and that I could call a Matron into the cell in a second, who would force her over the table, and so she bends over the table with her arms in front of her. I take a moment to enjoy the drama of her first presentation of her very beautiful ass.

Slowly and very gently, I lay the straps on the table across the small of her back, and secure her torso tightly to the table top. As I do this, she begins to cry, knowing the paddling that is coming for the form of torture that it is. She knows that it will break her. In point of fact she is already starting to break. There are three legs at each end of the table, one in the center, and one at both corners.  Every leg has straps available. I secure her knees and ankles to the center leg, thereby keeping her legs together.

For the next three minutes I do nothing but lovingly stroke her perfectly rounded, milky white ass, and admire how beautiful and unmarked it is. I know that there is very little chance that I will see it in this perfect condition again for some time, maybe never again; and I want to savor it, as I anticipate what is about to happen. Melissa continues to cry pitifully throughout these moments, which of course, only adds to my pleasure.

At length I stop admiring and caressing her ass. I give it a kiss, and then move up her back to her face, turned to one side, resting flat on the table. I kiss her on the cheek, and because she is still crying, wipe the tears from one of her eyes. I kiss her again and say, “Im going to give you twenty whacks now, for your first lesson. They will be two sets of ten, and I will expect you to count them. If you dont count them properly, Ill add another set of ten. Well take a 5 minute break in between the sets of whacks, to allow you to gather your composure. The whacks hurt quite a bit, and youll lose your composure during each set. During the break, Im going to put some of the lubrication on two of my fingers in order to lubricate your rectum. Youll need the lubrication, because afterwards, Im going to expect you to thank me for the lesson Im about to give you, first with your ass and then with your mouth.”

I pick the paddle up from where it is lying next to her on the table. I stroke her naked ass with my free hand, and then line the paddle up across it, much in the same way a golfer would line the club up with the ball. I give her the first whack of her life with the paddle. There is perhaps one second of separation between the impact of the whack and her reaction. She shrieks in pain, shock, and terror. Even though she was terrified of the paddle, and had seen the videos of other girls screaming and blubbering when they were receiving punishment from the paddle, she still had no idea that it would hurt this much.

Her scream echoes down the hallway of the cells. No words are needed to convey the idea that this girl is experiencing the most painful moment of her life thus far. There are at least 19 even more painful moments to come, each one cumulative, and more painful yet, than the one directly preceding it. I let her get a breath after the first whack, and with my free hand I stroke her ass. It is quivering slightly, because her body is trembling, and a red mark is already forming on each of her ass cheeks. Both marks are circular indicating a symmetrical even hit on both of her ass cheeks at the same time. She is whimpering and continuing to cry. I remind her that she had best count each whack, and she whimpers out “Number One Sir.” I respond by saying, “Much louder than Melissa. I want everyone down the hall to hear you counting.” She repeats it, this time shouting at the top of her lungs. She is clearly terrified. One minute has passed since her first whack, and I line the paddle up against her ass again.

I deliver each whack evenly, striking both cheeks in the center with each whack. During this paddling, I do not hit her thighs. There will be 2 large bruises on her ass, one on each cheek. They will both be purple when they are finished. Her ass cheek that is nearest to me will have the larger of the two bruises because more of the paddle strikes that cheek. I deliver each whack very hard. Melissa screams more shrilly with each whack, because the effect of the pain is compounded from the cumulative effect. Up until this moment, she really had no idea that anything could hurt this much. She follows each shriek with a cry of agony, blubbering really. After each whack, while she is blubbering and begging me to stop, I hesitate for at least a minute, which lets each whack fully burn in to her ass.

During that time I rub and caress her ass with my free hand, and observe how the two purple bruises are growing. Thankfully she does not seem to bleed easily, and after 5 whacks it appears to me that she will be able to take all 20 in the same 2 spots. While Im rubbing her ass, I do occasionally, playfully touch my finger to her rectum, just slightly putting the smallest part of my fingertip in and moving it around, as if to say, “This is next, after your paddling is over.” She doesnt object. She continues blubbering and begging, and counting the whacks. Occasionally, while resting between whacks, I kiss her ass, or shoulder, or face.

After 10 whacks, I tell her, “Good news! Were going to take a 5 or 10 minute break!” I immediately put on a latex glove. I cover my index and middle finger in lubrication and open her quivering ass cheeks with my other hand. Both lubricated fingers slide up into her rectum smoothly. She tries to compose herself and catch her breath, while she continues to sniffle and grunt slightly as I twist my fingers inside of her ass. This begins to slightly stretch her rectum a little bit more in preparation for our imminent union, 15 minutes from this moment, when she begins to understand how deep anal sex feels. I re-lubricate my fingers three times during our break, and she doesnt complain at all about this part of the process.

And then the paddle is back in my hand. She immediately starts to cry again, and with the eleventh whack, the screaming agony begins anew. This is followed by more begging and blubbering as each whack burns into her ass. It lasts 10 more minutes, and I am so sexually excited, that I have to begin having her. I put the paddle down, and kiss her face again. I open my robe in front of her, in order to allow her to see my swollen, throbbing cock through her tears. I wiped her tears from hers eyes gently with my thumb, and told her that her first lesson was over.

I walked around the table to stand behind her.  There was a large bruise on the middle of each of her ass cheeks. The smaller bruise was 2 inches wide. The larger of the two was perhaps 3 inches wide. I gently rubbed them both with my hands, and opened her ass cheeks, as I introduced the head of my cock to her rectum. I speak to her as I begin to put a cock into her ass for the first time of her life. “OK, Im going to put it in now. There it is. The head is in now. Now for the rest of it. Here we go all the way in. Dont clench, or Ill have to punish you. Let it all the way inside of your ass.”

At first it is resisted, and I have to push harder than I want to. But slowly, over about 15 seconds, all 10 inches slides into her, completely impaling her. She squeals a little bit and begins to cry again, as it overfills her lower bowel, and overstretches her rectum. But she doesnt complain. It hurts, quite a lot. But it doesnt hurt anywhere nearly as much as even 1 whack from a wooden paddle. She begins to tell me that it hurts, and that she loves me. I enjoy filling her. I enjoyed the reflexive, protesting grip of her asshole as I plow in and out of her, partially rotating my cock inside of ass, in order to give this tight little asshole the maximum stretching. On every inward thrust, she begins to moan in a high pitched squeal.

After 10 minutes, her sphincter muscles begin to spasm and gape open. Her squeals become louder, and higher pitched. She continues to tell me that it hurts and that she loves me. Her crying grows more intense, and contains a note of hopelessness. In spite of this, it is very clear to me that being fucked in the ass like this, even for the first time, is vastly preferable to being paddled again. For a moment, I completely withdraw my cock from her ass, and of course, it gapes wide, wide open. Melissa takes a deep breath of relief, with the hope that maybe this ordeal is over. I impale her ass again, plunging back in quickly. She squeals like a little girl. I smile down at her ass, holding it by the bruises, and say, “Weve only just begun my love. Try to get comfortable. You need to get to the point where you truly open up for me, so that I can touch you. I know you think that youve opened already, but you havent. You have further to go. You have to try harder to open yourself more.”

For the next hour and a half, I make love to her, standing behind her, sawing in and out of her rectum, as she is helplessly secured in her position to the table. I become familiar with the texture of every centimeter of the inside of her rectum, and it continues to reflexively gape open for my continued invasion. For the first hour, Melissas sobs grow louder and her moans grow more plaintiff. Finally, she calms down a bit, and stops telling me that it hurts so often, and begins to tell me more truthfully that she loves me, and that she wants to be owned by me. It was as though I had broken through the hard shell of a walnut, and had found the meaty inside part. I can taste her soul, wanting to be loved and cherished, and I connect with it. I sodomize her for another 20 minutes, as she speaks of her love, feeling our connection continue to grow. I feel myself to be fairly close to a climax, and finally take my cock out of her ass.

I release the straps that have secured her to the table, and help her up. She is covered with sweat and has lost all of her strength in her legs, and can barely walk, so I have to half carry her over to the bed, and have her kneel in front of it. I sit on the bed in front of her, with my robe open and my legs on either side of her. My cock is inches from her face, and it is glistening with the evidence of lubricated anal sex. I take her face in my hands and kiss her deeply on the mouth. “I want you to continue thanking me for your lesson with your lips, and your mouth, and your throat. I am warning you in advance that if you throw up in the process, Im going to have to put you back on the table for another paddling.”

She doesnt flinch. She looks more certain than I had thought she would be capable of. She looks me in the face, and says, “Im not going to throw up Master.” I bring her face forward slowly, and without hesitation, she takes my cock into her mouth, not as though her life depends on it, more as though she is hopelessly in love, and she needs to prove it to me. She uses her tongue beautifully as my cock slides first into mouth, stopping for a moment at the soft entrance to her throat. I press down slightly on the back of her head, and she responds to the direction like a well-trained pony, forcing her head down the rest of the way as my cock passes into her throat with a pop, and is fully enclosed in her mouth and throat. Her tongue continues to massage it, and she slurps on it, cleaning off the juices of her ass. It saws in and out of her mouth and throat, as she sucks it clean. Still driving into her throat I begin to orgasm uncontrollably directly down her throat. Somewhere in my brain I register that when I explode this far into her throat, it is actually easier for her to swallow my cum, because it is already past the part of her esophagus which controls her swallowing mechanics. This barely registers in my brain, because of yet one more peculiarity in my personality. I can take a very long time to reach the point of orgasm, however I seem to build up such a large release of energy in getting there, that when it occurs, I lose all conscious thought. There is no other thing going in the world. There is only the awareness of connecting to another persons consciousness; a female that has surrendered complete control of her being to me in the act of allowing me to connect with her. All of my consciousness is in my orgasm as I explode into her, and I almost black out in the process.

As my awareness returns, I realize that her mouth is still obediently wrapped around my cock, continuing to suck on it and drain it of any residual sperm. Her tongue continues to massage my cock, as it begins to ever so slowly go flaccid in her mouth. I can no longer feel her throat. I lift her head and take my cock out of her mouth. She has cleaned it completely, and swallowed everything- the cum and her ass juices together, without her stomach revolting. She looks me in the face and tells me that she loves me. I kiss her on the lips and tell her that I believe her, and that I intend to give her many more chances to prove her love for me in the coming week.

In many respects I am already in love with her. I am able to connect with her on a very intimate plane, something I am not able to do with many people. To make this connection, I unfortunately require everything she has, her entire personhood. It costs her everything she has. I will cherish it, but I will take…… everything.

Review This Story || Author: Jack Harlequin
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