Gables Academy

Chapter 2-  Michelle begins orientation.

There was a knock at the door to my office. I had been anticipating it. I opened the door and she stood there between the two Matrons. She was beautiful and extremely elegantly dressed. She wore a black business suit with slacks and a white blouse. Her 2” pumps brought her height to 5’4”. She appeared to weigh the 105 lbs. that her report had said she weighed. Her dirty blonde hair flowed past her shoulders. Her hands were cuffed behind her back and the Matrons held her arms, which was completely unnecessary. She clearly knew the consequences for disobedience. She was clearly terrified.

I loved moments like this.

I had the Matrons remove her handcuffs and asked them to remain outside as I brought her into my office and shut the door. I walked with her for the few steps to the front of my desk and held her arm as she looked at the desktop, upon which were some typical items you might expect to find on my desk: a writing pad, a phone, some papers, and a wooden paddle. I had been in this situation a number of times before, and every single time- without fail- the new girl involved stares at the paddle and begins to tremble. It is in that moment of truth in which she realizes that she is probably going to have her bottom paddled before she leaves the room. The abstract fear becomes tangible.

She doesn’t look at me. She continues to stare at the paddle. She stammers to me that she wants to be a good girl. She calls me Sir. I turn her by the shoulders to face me, and look into her eyes and smile. I take her in my arms and hold her. I inhale deeply as her hair is next to my face. Her body presses lightly against mine and I feel her small breasts against my chest. Her loins press against mine and I am sure that she can feel me beginning to become aroused. I inhale her soul and taste it. It is delicious. Her name is Michelle and I call her by that as I whisper into her ear, and tell her that I know she is going to be a very good girl. She is 25 years old and she is going to be a good girl for a very long time.

Only a week before she had been engaged and had been planning her marriage. In the New Republic it was unusual for a girl to be this old before she was married. Her father had died a number of years earlier and her mother had been able to manage their family without remarrying. As a result, there was no father figure in her family to mandate and oversee her marriage in her teens. Her fiancé was a very nice young man that had dated her for a couple of years. I had been acquainted with his family. Michelle had recently made it clear to him that she had no intention of being as submissive to him as social protocols required. He came to me in the hope that I would be able to nullify his engagement with no negative consequences to him. He did not have an appetite to force her compliance.

After seeing Michelle’s pictures I was more than happy to help. It only took one phone call. She was pulled over in a routine traffic stop. The police officer searched her car and found a briefcase in the trunk containing an ounce of methamphetamine. She was arrested. A subsequent search of her home turned up an additional kilogram of the same substance. Her mother and younger sister were also arrested. The news reports all lamented the results of what happens when the family structure breaks down, and there is no father to maintain discipline.

All three women were tried separately, convicted, and sentenced to death. Their executions were held in abeyance. The mother- who was still quite attractive- was remanded to the custody of one of the arresting officers. The younger sister was remanded to the Custody of Gables Academy, a women’s re-education facility that is adjacent to the Governor’s mansion, which is my home. Michelle was remanded to my custody. I would take charge of her re-education. As I held her in my arms for the first time in my office, I was very much looking forward to beginning the process of turning her into a very good girl.

I continue whispering into her ear and ask her if she will do something for me. She tells me that she will. I ask her to please take off her shoes and put them on the desk. She says “Yes Sir”, and quickly steps out of her shoes and puts them on the desk. I take her back into my arms, and as I hold her I slowly begin to kiss her. Her lips part as I kiss her and her mouth opens to accept my tongue. I kiss her deeply enjoying the feel of her tongue on mine. I hold her close to me and again whisper into her ear, “Now if you don’t mind Michelle, would you please take your pants off for me?”

She takes a deep breath and whimpers, “Y-Y-yes, Sir”. Slowly, she steps back from me and unfastens her belt, almost as though she has to think about every movement in order to force herself to do it. She unbuttons the top of her pants and she unzips them. Then putting her thumbs into the top of her open pants, she takes them down to her knees, being careful to leave her panties still on. Bending down she pulls her pants down to her ankles and steps out of them. Carefully she folds her pants and puts them on top of her shoes on the desk.

She turns back to face me, but she can’t look me in the eyes. She is blushing with embarrassment. With her pants off she suddenly feels much more vulnerable and available. I take her again in my arms and kiss her deeply. She is even more responsive. She may be hoping that by being more passionate and loving, that she can avoid the discipline aspect of our first love session together. She may hope that it can just be a love session, and that perhaps she can avoid having her bottom paddled. That hope is quite misplaced.

As I hold her in my arms and kiss her, I begin to explore her more exposed areas. I put my hands down into the back of her panties, and cup her bottom in my hands. I separate her ass cheeks and she whimpers a little bit as I put my finger up into her rectum a little bit. She continues to kiss me and does not resist in any way. I put it in a little further. She continues to kiss me.

She has been preparing for this time since her arrest and conviction a few days earlier. She has watched the tutorial videos and been talked to for a couple of hours each day by a Matron- House Mother. She understands what will be expected of her and that she will be doing things that she never thought she would do- depraved things.  She understands the demerit-punishment system of my house and our school. In theory she understands consequences.

I stop kissing her for a moment and again whisper in her ear. “Now please take off your jacket.” I take my finger out of her backside as she takes her jacket off, and folds it and puts it on top of her pants on my desk. I sit down in one of the guest chairs facing my desk and have her stand in front of me. I draw her to me and hold her ass in my hands as I rest my head on her chest and I put my face into her blouse between her breasts. Slowly I inhale her again. Holding this girl like this, feeling her soul and her fear, and knowing what I am going to be doing with her is like a form of meditation for me. I can taste life at this moment.

The moment passes and slowly I lift my head and begin unfastening the buttons of her white, short sleeve blouse.  Moving up from the bottom, there are six buttons. When the last one is open, I put my hands into her blouse and around her back, drawing her to me again as I bury my face into her cleavage. I kiss the top of her breasts. I remove her blouse and put it on top of her other clothes. I say nothing, but I look her in the eyes. I point to her bra and motion with my finger. She unfastens it at the clasp in the front and exposes her breasts as she takes off her bra and puts it on top of her other clothes. Her breasts are a B cup, perhaps a bit small for my taste. But they are firm, perfectly formed, and very beautiful. 

I draw her to me again, and immediately one of her breasts is in my mouth. I bite her nipple just a little bit and she jumps and squeals, but does not resist. I repeat the process with the other nipple and she accepts it. I suckle on her breast a little bit more, continuing to intermittently bite it. She accepts this completely now and holds my head in her arms as I taste her. I move her back a step and look into her face as I pull her panties down and she steps out of them. I hand them to her and she puts them on top of her other clothes. She turns back to face me.

As I again begin to taste her breasts, she again holds my head in her arms. She doesn’t resist as I then put my hand into her crotch. It is hairless. She has been showered, shaved, and perfumed that morning. She has been given a 2 quart enema, just in case I should wish to fully access her rectum in our first love session together. My fingers separate her vaginal lips, and as I hold her and taste her breasts, I also begin to gently explore her internally. She moans slightly.

I allow myself 2 minutes to enjoy this beginning of our passion. It would be extremely easy for me at this point to continue this line of pleasure. It would be very easy for me to put her onto her knees; and bring her hands to my belt and have her open my pants and have her begin caressing my swollen cock. It would be very easy to then bring her head to my cock and have her begin suckling on it fervently, until it explodes into her mouth with my sperm, which she obediently would swallow. But my plans today include other aspects of a transformation for her that is additional and incremental to those things. Pain is required. So is fear.

I stand and hold her with my arms around her, and again smell her essence in her hair. Again I whisper into her ear. “Now please, if you don’t mind, please open the door to my office.” I sit back on the front edge of my desk and watch her as she walks fully nude to the door of my office. Her body was a work of art- a perfectly rounded bottom, an hourglass waist, slender legs and arms. She stands in front of the door for a moment and takes a breath as she holds the handle and summons the will to open the door. She opens it.

The Matrons who delivered her to me are still waiting outside my office door. There is a lot of activity outside of my office beyond the Matrons. My office is in my home, but my home is the Governor’s mansion. By its very nature, it involves many, many people. The people in the public room outside of my office all stop for a moment to look at the beautiful, fully nude girl that has just opened the door of my office.

This moment is humiliation at its finest. She is naked in the Governor’s office. She has a very good idea of what she is going to be doing very shortly. So do all of the people outside. They look at each other and she knows what they are all thinking. For that moment everything has stopped. They all look at her and she looks at the floor. I ask her to come back to me, and when she does, I again take her in my arms. I again inhale her and whisper into her ear. “Please give your clothes to the Matron and ask her to have them burned.”

Her clothes were neatly folded in a very tidy stack on my desk. They are one of the few vestiges of her previous life. She picks them up and hands them to the nearest Matron, saying- “Please Maam. Please have these clothes burned.” I told her to close the door and her first moment of humiliation was over. It was time to begin.

I called her back to me and held her again in my arms, breathing her in and tasting her fear. I again whispered to her. “Bend over my desk. I want your face to be flat down on the desk. We’re going to begin your first lesson now. If you’re a very good girl it won’t have to be too long or have too many phases.” Hope is no longer in the room, but fear is very much present.

She was trembling and whimpering, but she assumed her position. Fine tuning her position just a little bit, I had her stand up on her toes as she pressed her face into the desk with her arms in front of her. The view was spectacular. I had a clear view into her rectum and vagina. Her ass framed perfectly almost inviting me to take hold of that hourglass waist and begin using her on the spot. Instead I picked up the paddle that was next to her on the desk. I took my position as the Punisher and lined the paddle up on her ass, lightly rubbing it as she trembled. I told her that the first phase was going to be 20 whacks, and that she was to count them out loud, and say “Thank you Sir” after each whack.

She waited in terror for the first whack. Before delivering it, I decided to speak to her again. “Understand this clearly Michelle. If you move out of your position I will call the Matrons in and they will secure you to the desk. If you try to block even one whack with your hands, I will call the Matrons in. If you lose count, we will start over again. If you forget to say thank you, we will start over again. You can beg me to stop, but you are getting 20 whacks with the paddle. You can offer me the use of your mouth, your cunt, or your rectum. I will use you in all of those places whether you offer them or not, and in any sequence that I choose. Other men will have exactly the same access of use with you. Those things are not yours to give. They are mine to take for myself, and give to others if I choose. But feel free to beg me to use you. I hope for your sake that I have made myself clear. If I haven’t, 20 whacks will very quickly become 100.”

And so it began. I gave her the first whack and she shrieked. I’m quite sure that all of the people outside of my office could hear both sounds very clearly. I delivered it hard and evenly on both cheeks of her ass. The first whack when it is delivered with force is like a wave of agony. My girls tell me that it’s almost like a bolt of electricity that travels up their spines to explode in a flash of white light in their brains, followed by agonizing pain in their asses. As the initial pain subsides, they remember to count and say thank you. Usually they have dropped down from their toes and collapsed on the desk, having momentarily lost all of the strength in their legs. They have to be reminded to resume their position and get back up on their toes. I don’t hold this against them as a loss of position. I rather enjoy it when they whimper and cry, and get back up onto their toes. Because then their fear really begins to take over.

They have two major fears. First, they really fear the next whack- and they don’t know when it’s coming; and they intermittently blubber when they think it’s about to happen. I will usually space my whacks out by at least a minute. I like to give my girls a chance to gather themselves between each whack. I like to rub their bare bottoms and thigh backs with my hand or the paddle. I love the way their asses feel when they quiver after a whack. I love to watch the bruise or the welt forming after the whack so that I can build on it. All of this gives them time to anticipate the next whack and become progressively more terrified of it.

Second, they really fear having to go through the whole paddling- or worse -start over if they lose count, forget to say thank you, or really leave their position. I love getting to whack 10 or 15, and saying to the girl “Excuse me, but did you just leave your position?” Terror strikes the girl so quickly then. The girl snaps into position very quickly as she wails, “NO SIR, NO SIR, I DIDN’T. I DIDN’T I DIDN’T!!!!!.” After a few whacks their asses hurt so much that they beg to rub it, just for a little while. The begging is always enjoyable, and they always beg profusely.

Michelle was no exception. She almost left her position after the first whack. As I rubbed her milky white ass with my hand, two black and blue bruises began to form on each of her ass cheeks. They were each about an inch in diameter. I decided to build on those, and to put one additional, nice round bruise on each of her thighs. I took the time to kiss those bruises and tell her how beautiful they were, and how beautifully I thought she was going to continue bruising. She was sobbing and completely consumed by terror of the next whack. Even though she had seen a video on getting paddled and understood the theory of it, she had no real idea how much it was actually going to hurt until that first whack.  I therefore took an extra couple of minutes to let her appreciate it and anticipate the next one. I talked to her and rubbed her ass, first with my hand and then with the paddle. I told her that there could be as many as 5 phases to her paddling, and how incredibly black and blue she might be by the end. And I hit her again.

By whack 10, all four bruises were blooming beautifully. Michelle collapsed onto the desk after each whack, but she held her position, got back up onto her toes quickly, and counted and said thank you. She sobbed and begged so loudly that everyone outside of my office could hear her quite clearly. She had a high pitched voice of a soprano that really carried when she screamed. She was sobbing pitifully and imploring me through her tears to stop or at least to take a break. I told her to hold her position.

I put the paddle down next to her and walked around to the front of my desk, enjoying the slightly different perspective of this beautiful girl. As I looked into her face filled with pain and fear, and streaked with tears, I opened a desk drawer and removed a couple of latex gloves and a jar of lubricant. I remained standing at the front of my desk in order to allow Michelle to see what I was doing. I put on one of the latex gloves, and after opening the jar of lubricant I generously applied some onto the first two of my gloved fingers. Walking back around the desk so that I was again facing Michelle’s ass, I put the jar down next to her. With one hand I opened her ass cheeks, and pushed- none too gently- two fingers up all the way into her rectum. I didn’t put them in slowly and I had to use more strength than one might anticipate. She was a virgin in her ass and was very tight.

I spent a number of minutes reaming her tight little asshole with my fingers, listening to her repeat “Ow… ow…. ow!” as she vocalized her pain. I kept turning my fingers inside of her as I reamed her, and every minute or so I would withdraw both fingers to see if her asshole would gape open. She was too tight for that to happen- yet. The moment my fingers came out it would pucker closed. After 10 minutes, I was becoming progressively more aroused. I wanted her right there- bent over the desk. But first there were another 10 whacks that I had promised to her.

I withdrew my fingers and removed the latex glove. I picked up the paddle and rubbed her ass with it, and began to line up whack number 11. Michelle began to whimper and cry again, and said, “Please Sir. Please….no more. Please don’t paddle me anymore. …. I’ll do anything you want me to.” I told her that I knew that- and I hit her hard.

I took even more time between each whack on the last ten. I used most of my strength on each whack, and her shrieks reflected that. The bruises on her ass and the backs of her thighs grew significantly. I must have been making slightly harder contact with her closest ass cheek, because she began to bleed slightly from the center of her bruise there. The shrieking and sobbing grew louder. She counted each whack and said thank you- actually she screamed thank you. She begged me to stop after each whack. I repeatedly said no. The last 10 whacks took 15 exquisite minutes. She asked me repeatedly to use her, offering her every hole by name. I told her I would use her after phase one of her lesson. She held her position on my desk.

And then it was over. She was sobbing and trying to catch her breath, and telling me that she would be a very good girl for anything I wanted to do. I put the paddle down next to her on the desk. Standing behind her, I rubbed her bare, bruised bottom with my hand for a couple of minutes, and told her to calm down.

Slowly she did calm down, and standing directly behind her I opened my pants and got my cock out. It was fully engorged, nine inches long and two inches thick. I rubbed it between her ass cheeks as I held them in my hands. I positioned the head of my cock at the center of her well lubricated asshole and spent a minute or two enjoying the sight and anticipating the moment. I pushed the head in firmly. Her rectum resisted, but with a firmer push the head popped in past her sphincter. She let out sort of a moan-grunt. I had her use her hands to hold her ass open.

I then began her in depth introduction to the joys of anal sex.

First year medical students are often surprised to learn that there are actually two sets of muscles in the sphincter. There are actually two distinct doorways involved, almost like a storm door and an inner door. It facilitates much greater control in our defecation process. It also makes opening an anal virgin much harder work. Even though I had relatively easily popped the head of my cock into her rectum, there was still a great deal of resistance from her inner sphincter muscle. This was expected and I pressed in harder.

Her moans of pain became more obvious. She did not resist. In point of fact she had gone almost limp as she was bent over the desk. She did not complain, but she did moan- loudly. It heightened my excitement.

As a teenager, long before I had developed any real sexual experience with girls, I had asked my father about anal sex. His answer to me was one of many defining moments of my adolescence. He dismissed the idea of trying it even as an alternative, saying that anal sex hurt girls so much that only a sadist would be interested in it. He said it to me definitively- as in “Case closed”.

It seemed prudent to me not to mention to him that I was a sadist, something I already knew, and had known for a very long time. Rather than thinking about it in terms of “Case closed”, I knew at that moment that I was going to love anal sex. Over a period of years I developed that love into finely refined moments with virgins who are unable to conceal their pain while I am opening their asses. I think they hope that if they show me how much it hurts them, that I will not force it in all the way and instead will be satisfied with only a partial penetration of their rectums. I don’t think it usually dawns on them how much I enjoy hearing and feeling them moan and grunt with pain, while my cock inexorably continues to impale and plow them.

I plowed Michelle inexorably. The first full deep stroke met with great resistance, but did not stop at any point. She told me later that she was frightened that something inside of her was tearing. She moaned loudly and I continued to plow inside of her. The sight of her bent over my desk in front of me holding her ass open, with her fingers partially covering the bruises on her ass was incredibly exciting to me! I took my time stroking in and out of her. I felt like her ass was gripping my cock. After the first 5 minutes I took my cock out of her and she sighed with relief. Her asshole gaped open with an invitation to re-enter her. She gasped with pain when I plunged back in.

For the next 20 minutes I continued to take her this way. Michelle moaned and grunted her pain the entire time. Every couple of minutes I would withdraw my cock from her asshole, look deeply into it while it was gaping wide, wide open; and plunge back into her. I felt myself beginning to approach a climax and withdrew from her. I stood her up and tried to walk with her over to the sofa on the other side of my office. I almost had to carry her. Between the paddling and the ass fucking that she had just been through while she was bent over my desk for the better part of the last hour, she appeared to have lost most of the strength in her legs- and was unable to walk without assistance. I held her up as I walked her there.

I sat on the couch and had her kneel between my legs on the floor. Her face was thoroughly streaked by her tears, and through her tears she was incredibly beautiful. I kissed her on the mouth deeply. I told her that it was time for her mouth, and that I wanted her mouth to clean my cock thoroughly and finish our love session. Her eyes went wide as she really looked at my cock. Although it had been up her very well lubricated ass for the last 20 minutes, she just then noticed that it was covered with a translucent, thin brown film- a combination emulsion of all of the elements that had recently been in her asshole.

She was afraid. She was afraid of getting sick from tasting her own feces and she was afraid of getting paddled again if she didn’t perform well. The fear of getting paddled again was the greater of the two, driven by the throbbing, burning pain she still felt on her backside. She opened her mouth and closed her eyes as she took my cock into her mouth and began to suck me.

She had watched a very explicit tutorial video on how girls properly perform oral sex at Gables academy. She had watched it twice. Between the two viewings, she had spent a couple of hours with a House Mother who had in detail explained all of the finer points she might have missed, as well as the consequences of not being a “good girl”. Because of this very thorough preparation she understood most of the finer points of making love to a cock with her mouth. She understood using her tongue on the cock- swirling it around- as though she were French kissing it. She understood taking it into her throat and how to overcome the gag reflex as it was swallowed into her throat. She understood the importance of having the cock deeply in her mouth while it was ejaculating. She understood that some men might want her to show them her open mouth after an orgasm while it was still full of sperm, but that unless otherwise directed, she was expected to swallow the sperm as it was flowing into her mouth- every drop. And she was expected to say thank you afterwards- and mean it. Her paddling had left her with a bruised and burning bottom to remind her of the consequences of anything less than a perfect performance.

The tutorials had done their job. She was able to ignore the slightly bitter and slimy taste in her mouth as she slurped on my cock. The first few strokes went to the back of her mouth. She used her tongue beautifully. I put a little bit of pressure on the back of her head with my hand as it was stroking down. My cock reached the opening of her throat and I pushed a little bit more on the back of her head, and it pushed into her throat with a pop. Every stroke after that one went in the full 9 inches, and I spent the next 5 minutes thoroughly fucking her throat. I had closed my eyes and just enjoyed the sensation and the sound as I ejaculated in 6 or 7 long spurts. I felt her struggling to swallow each flow and could hear, as well as feel her gulps as she took her medicine down into her stomach.

I left my cock in her mouth for another minute after I had finished my climax, and she continued using her tongue to finish her task of cleaning it. I took it out of her mouth and kissed her on the forehead. She looked up at me and thanked me. She looked as though she were struggling with something that she was trying to hide. I had been through this moment a number of times before and knew exactly what it was. Her stomach was starting to betray her now that she had a moment to think about everything that had just happened. She was feeling herself getting sick and trying to fight it off. The taste in her mouth was reminding her of everything she had just swallowed, and she was fighting a losing battle to overcome it.

I innocently asked her if something was wrong, and she in reply asked me if she could please go to the bathroom. There was a full large bathroom attached to my office, and I told her that she could use it.  She went into it and about 30 seconds after shutting the door I could hear her begin to throw up. I took the liberty of opening the bathroom door to watch, and for the next 5 minutes she knelt in front of the toilet retching violently into it. Between long moments of violently vomiting her guts out, she would get her breath and sob an apology out to me. I watched in silence. When she finally stopped I helped her up and let her rinse her mouth out, and wash her face.

She started to cry again and she begged me not to paddle her again as punishment for getting sick. She promised sobbing that she would do better the next time. I took her head in my hands and kissed her on the forehead as I said, “Almost every girl throws up the first time they do that. I’ll give you more chances. If you still have trouble after that, we have a more intensive anal/oral training regiment available. One way or another you’ll get through it. We can forego any more punishment this time.”

Her response could have been hysterical sorrow or revulsion at what I had just told her she was going to be doing in the immediate future. It wasn’t either of those. Her response was gratitude, first in her eyes when she understood that she wasn’t going to immediately be beaten again. This was followed by the gratitude she expressed verbally as I took her in my arms and held her like the vulnerable little girl she was. She buried her face in my chest and repeatedly thanked me, and for the first time called me Master. It was spoken as a term of both endearment and fear.

I kissed her again on the forehead and opened the door to my office. I asked the 2 Matrons waiting there to escort Michelle up to my apartment, and to help her get ready for dinner in a few hours. I watched her as she walked out of my office fully nude between them; and again I enjoyed the view of her perfect body, as she walked through the public room with that hourglass figure, with four good sized black and red bruises. With or without the bruises, her ass was a work of art. So was the rest of her. After her personality was fully re-shaped, she was going to be truly amazing.