Caroline's Rocking Horse (2 page)

What I wasn't
avoiding, however, was masturbating while fantasizing about the many erotic acts and situations I was so sure I would never get to realize in my own life. It had gotten to the point where I would spend an hour in the evening before George got home with my stash of special reading material (which I'll describe in a little while), giving myself orgasm after orgasm, and then literally feigning a headache when George showed the slightest interest in making love, so afraid was I of how sad I would be in feeling the distance between what was happening in our queen-sized sleigh-bed and what I was reading about.

What was I reading about? The nice word for it is
ageplay, so we'll go with that. Little girls and their daddies (or uncles, or headmasters, or clergymen). Their daddies spanking them and making them do shameful things.

This, for example, was what I was
reading the night it all began. If you want the genuine article, you can find it on several websites these days; it's from the Victorian period, and it's named after a beautiful, spherical object produced by oysters, used in jewelry, and for various reasons one of the sexiest things in the universe. As I said, I can't give you an accurate rendering of what's in that authentic Victoriana, so we'll pretend that it went like this:

* * * * *

When I was a girl of eighteen I was sent to school. The headmaster of my school was an older gentleman named Mr. Hastings. From the moment I saw my new headmaster, I began to feel new emotions, and new excitements, which I had never before known. He seemed to me the kindest, most wonderful person in the world. I truly believed that there was nothing Mr. Hastings did not know and that there was nothing he would not do to help his girls become well-educated young women, ready for marriage to the wealthy husbands for whom we all longed.

Whenever Mr. Hastings, as he wandered through the school-room, checking our work and giving us little compliments and words of encouragement
, bent over my desk and rested his hand on my shoulder, I yearned for something of which I did not really yet know the nature. I lay in bed at night in the dormitory with the other new girls sleeping around me (there was one room for the newer girls, and another for the more advanced girls, across the hallway), and tried to discover what these new feelings were. Sometimes I thought I could hear the other girls sighing the same as I, perhaps thinking of the same things I was as I explored with my wicked idle hands the changes through which my body was going. Sometimes I even thought I could hear below, in the area of the schoolroom and Mr. Hastings' study, strange cries of other girls, as if they were being punished—or as if they were somehow being pleasured to an extent I could not truly conceive. The strange sounds always made my idle hands even more wanton around my young charms, until I thought perhaps I understood about how one could be made to cry out in one's pleasure.

These new feelings so distracted me that my schoolwork—never a topic of concern before I was sent to that school—began to suffer. Rather than copy my lesson, I would be thinking of what might happen if I should be called to Mr. Hastings' study. I blushed furiously, thinking (for reasons I could not fathom) that he migh
t tell me to remove my clothing and inspect me—and touch me—and tell me that I needed to feel his firm hand guiding me.

After I did terribly on my first examination, Mr. Hastings did
, indeed, send for me to come to his study.

"Miss Lewis," he said to me sternly, as he sat behind his desk. "I am afraid that your results are by no means those we were expecting of you."

"No, Sir," I replied, with my head bowed.

"Something will have to be done about this," said Mr. Hastings.

I knew from whispered discussions with the other girls that when Mr. Hastings said that something had to be done, the something was always the cane. I knew also that the young ladies of Mr. Hastings' establishment were always caned upon their bare bottoms, to ensure that they understood the importance of stern correction in the guidance towards proper behavior. It was indeed for that reason that my parents had sent me to his school, because he was so renowned for producing well-behaved young ladies.

Thus, when Mr. Hastings said to me that something must be done, I was terribly afraid, for I knew exactly what it m
eant and the terrible thrashing that I must soon receive. At the same time, however, a strange thrill went through me at the shameful thought of Mr. Hastings looking at my bare bottom—and even at the idea of him striking it over and over with his cane. There seemed to be a fire in my loins, the same kind of which I'd had inklings in my bed but which I had never felt so strongly as I felt it when I pictured Mr. Hastings holding the cane poised to strike my exposed backside. All of a sudden, to my astonishment, I felt that I wanted to be over Mr. Hastings' desk with my drawers down.

"Yes,
Sir," I whispered.

"What's that, Miss Lewis?" asked Mr. Hastings.

"Yes, Sir," I said, a little louder.

"Do you know, then, what must now befall you, Miss Lewis?" he asked.

"Yes, Sir,"

"What is that, Miss Lewis?"

"The cane," I said, returning to my whisper.

"I am afraid that I must require you to speak a little louder, Miss Lewis. In my establishment, girls are grateful for the discipline I provide, and thus if you wish to remain here, you will request
of me respectfully to cane your bare bottom."

I felt my face flush crimson, and
I found myself unable to speak.

"Well, M
iss Lewis," the headmaster said, "I am waiting."

The flame in the parting of my legs seemed to kindle itself into a conflagration. I made a little sobbing sound, I think, but I was still unable to say a word.

Mr. Hastings voice became a little kinder. "I imagine, Miss Lewis, that this will be your first time going under the cane. Is that so?"

"Yes,
Sir," I was finally able to reply.

"I understand how hard it can be for a new girl," he continued, "but I cannot allow that to impede my sense of duty to your family. I am afraid that I must require
you to request your punishment or to vacate my premises."

"Oh, no,
Sir," I cried. "Please, Sir, cane my bare bottom. I want to do better; I want to be good; it's just so—so difficult...."

"Let us take care of your chastisement first, Miss
Lewis," said Mr. Hastings. "Then we may discuss your difficulties."

He rose from his desk
and made his way around it towards me. He put his hands upon the shoulders of my blue school dress and led me to the punishment block, gently urging me to kneel upon it by the pressure of his hands. He raised my skirts, rolled them up and pinned them to my bodice so that they could not fall down, cover my rear and thus deprive him of the ability to administer just chastisement to my bare bottom.

Then he reached
around to the front of my waist to unbutton my drawers. I thought I would die with shame, but at the same time the delicious fire was still at play in the parts that he had uncovered.

"Twelve strokes, now, to help you understand the importance of concentrati
on." I had not been aware of his fetching his cane, but now I heard a whistling sound that I had never heard before—but which I had imagined many times. At the same time I heard the smack of the rattan striking my poor bottom and felt the searing line of pain across my flesh. Strangely, though, almost from the first moment the searing pain made its way forward to add to the fire of my wantonness. I held tightly to the corners of the block as I began to sob with the pain of the strokes falling, one after the other, upon my plump young bottom-cheeks.

Mr. Hastings laid the strokes on with great s
everity until I was crying out and the tears were streaming down my cheeks. "Oh, Sir, please... please," I was saying.

When the twelve
strokes had fallen, Mr. Hastings said, "Now, Miss Lewis, you will stay that way for the next ten minutes so that you can contemplate the want of concentration that led you to such an embarrassing and painful condition."

He put the cane away and sat down at his desk.
I kept crying for a little while as the stinging pain of my twelve welts faded into a sort of burning smart. Something else was happening, though, to my horror: that same burning smart was somehow multiplying the heat between my thighs, in my tender young private part, many, many times. The torment was no longer a torment of pain, but a struggle to keep myself from wriggling and clenching my bottom shamefully, as Mr. Hastings watched.

But w
hat I simply could
not
prevent was the way the liquor of my little pussy began to run onto my thighs, making me shift uncomfortably, desperate to hide the fact from Mr. Hastings. That shifting, though, lamentably aroused me even further, so that I had to utter a soft "Oh!"

"Miss Lewis?" asked
Mr. Hastings. "Are you well?"

"Oh,
Sir. Yes, I... yes, Sir."

He rose from the desk and I heard him rounding it, to come over to me in what seemed to b
e his great concern for my well being.

"Sir, please
... please don't look!"

"Don't look at what, Miss Lewis?"

"At... Oh, Mr. Hastings, what are you doing? Where are you touching me?"

"Shh Miss
Lewis. The young ladies of my establishment know how to please their headmaster. It always seems strange to a new girl, but I can assure you that soon enough it will feel lovely."

"Oh, Mr. Hastings—it already feels lovely."

"That's because you are so very, very naughty, Miss Lewis. Your parents sent you to my school for just that reason, and they have given me permission to help you in any way I see fit."

"Ah
... oh, goodness, oh, Sir..."

"I have found that this is the only way to help girls of your character
—girls who have a bright future but whose erotic proclivities are liable to cause disaster unless they should be taught about them. If girls like you are to be safe, Miss Lewis, it is very important that you be introduced to the vicissitudes of your wanton nature by an experienced man such as I. Now that you have had your first chastisement, it is time for me to begin your true initiation as a pupil at my school."

Mr. Hastings
tenderly stroked the bottom he had so lately disciplined. I moaned and sighed. "You have a very lovely bottom, Miss Lewis," he murmured. "There are many things that need to be done to it here in my house."

To my surprise and astonishment, he began to move his forefinger inward between the two parts of the posterior he was caressing.

"Oh!" I said.

"Be silent now, young lady," he said. "It is very important that you learn about this part of your anatomy. And it is important that I should inspect it minutely. You must learn to be a good girl, now."

"Oh, Sir, what are you doing? That part is..."

"Quiet, young lady," Mr. Hastings said
, sternly. He gave me a spank with his open hand on my right bottom-cheek. "Young ladies who are being inspected must be quiet."

But I couldn't help myself;
I let out a little shriek as I felt him urging his fingertip inside that very shameful opening.

"Silence, Miss Lewis, or I shall have to gag you. You will have this lesson whether you like it or not. You are a very naughty girl, and now you are learning what happens to naughty girls."

You get the idea. I lay back against the pillows, propped up in bed, as I let the book fall to the coverlet. I was home alone, as usual. If the past few weeks were anything to go by, George wouldn't get home until after I was asleep.
As professionals who always needed our sleep in order to be at our best in our professional lives, waking one another up for sex was something we had never done, so there was no prospect, even, of the pallid satisfaction that making love with George could provide. Despite the reluctance to which I have confessed above, nevertheless, once that reluctance was overcome, it provided during those years some respite from the fantasies I was now indulging with the help of this naughty book.

That kind of limited satisfaction, though, would not be happening tonight. This was my self-pollution calculus, and I engaged in it whenever I was about to step past the bounds of shame that, despite my inveterate habit of polluting myself nearly daily, nevertheless still held some embarrassment for me. Looking back, I can see that this calculus itself contained t
he seed of the fantasy that dominated my imaginary life. Just as Miss Lewis in the book I was reading longed to be punished for her wantonness, so did I go through mental contortions about my masturbation in the fantasy-hope that George would hold me accountable for it and might want to discipline me, as Mr. Hastings had to discipline Miss Lewis.

In any event, my hand found its way under my short nightgown and into my panties. I thought about Mr. Hastings and Miss Lewis. I thought about what Mr. Hastings might do with Miss Lewis after he had initiated her into the ways of the paternal headmaster. Truthfully, if you do seek out the genuine article, Mr. Hastings' character will u
sually do the kinds of things that I fantasized about—or if the headmaster doesn't, some other paternal figure eventually will. So I could simply have kept reading while I played with myself.

But I want to acquaint you with the
strange nature of my fantasy life, so that you can understand fully what happened that night—so let's say that I did stop reading, lie back against the pillows and let my hand find its way under the nightdress and then under the waistband of my panties, to bring the fingertips where I needed them the most. On the fantasy stage of my mind, Mr. Hastings did terrible things to Miss Lewis, and Miss Lewis loved them.

* * * * *

The headmaster's finger was in the schoolgirl's bottom, moving gently. The young lady was making less-than-ladylike sounds. "Sir! Is it not... ah... isn't it wicked?"

"Yes, Miss Lewis, it is indeed wicked." He added a second finger, which made Miss Lewis give a little sob of shame. "You are a wicked girl, though. Do you t
hink that I haven't watched you in the dormitory? Can you pretend that having my fingers here isn't just what you deserve?"

Now with his other hand
he began very lightly to tease the part of Miss Lewis that she played with in her dormitory bed at night when he was watching through his peephole—the part that seemed to be the root of all her wickedness.

"Oh, Sir
... how can you?"

"Answer me, Miss Lewis. Can you pretend that you aren't the kind of girl who should have a man's fingers in her bottom?"

It was monstrous, what I was subjecting poor Miss Lewis to at the hands (literally) of Mr. Hastings. Monstrous—except that it was exactly what I wished some authoritarian gentleman would do to me. Can it be monstrous if you want it done to you?

Monstrous or not, it was the core of my being—I could admit that to myself at a time like this, in the throes of self-directed, fantasy-elaborating passion, even if I couldn't admit it to myself when the orgasm had ebbed away from my relaxing muscles, and the shame and self-revulsion were upon me. I would have done anything to have someone who would tell me that I neede
d to have his fingers in my bottom, and who then would put them there while instructing me sternly, but patiently, in the ways of his pleasure.

* * * * *

"No, Sir. No! Oh... please—I'll be good—I promise!"

"It is too late for that, Miss Lewis. You are a naughty, wicked girl who is finally receiving what she deserves."

My mind fast-forwarded the fantasy. After he had made her come with his fingers inside her bottom, he had sent her back to class with the instruction that she was to come to his room that night at eight o'clock.

My fingertips slipped and slid along the furrow of my own loins. Oh how I wanted to be Miss Lewis! I put my left hand i
nside the neck of my nightdress and began to toy with my right nipple. I closed my eyes and sighed deeply.

* * * * *

"You are to call me Papa, now," said Mr. Hastings to Miss Lewis after he had met her at his door, picked her up and carried her to his bed for the first time.

"Yes, Papa."

What would Mr. Hastings do to her then, when she was in his bed? There was the thing he had prepared her for in his study. There was that. I resolutely refused to touch myself there. I thought about Mr. Hastings and then about George, and then about George as Mr. Hastings. Blushing even though I was alone, I thought about his cock.

I
n my fantasy, Mr. Hastings said quietly to Miss Lewis, "Lay yourself over this bolster now, young lady. I should like to see how my cane-marks are coming along."

Miss Lew
is was in her night shift—with no panties, of course, because panties haven't been invented yet. So easy to lift that thin cotton and expose the little bottom with the twelve purple stripes that still burned like fire as Mr. Hastings ran his finger along them.

"Lovely
... lovely. You will look at your bottom in the mirror every night, young lady, as a reminder of your punishment. Do you understand me?"

"Yes, Papa."

"You have been a bad girl, but with the help of my cane, you will learn to be a better one, will you not?" Standing behind her where she lay on the bed, bottom-up over the bolster, he held her whole backside in his hands, one cheek in each.

"Yes, Papa."

"This little bottom will feel my cane many times before you leave my establishment forever, but I promise you, you will be grateful one day that you were fortunate enough to have a headmaster who chastised you so severely on your bare bottom."

"Yes, Papa."

He stroked her bottom tenderly. She made submissive little sounds of the kind that daddies like to hear from their little girls. His fingers moved inwards, towards the little puckered bud at the center.

"Now it is time for your papa to enjoy you the way he likes best."

"What way is that, Papa?"

"Your papa is going to put something in here, and it will make him feel very good."

"Oh, please, Sir," said Miss Lewis, "couldn't I do something else? Something else to make my papa feel good?"

"Quiet, young lady," said Mr. Hastings. "This is what your papa likes to do to little girls, and he is going to do it to you."

* * * * *

I felt my flush of embarrassment at the fantasy spread down my chest and seem to cover my entire body. I could never seem to stop myself from it, this descent into the dark passage.

Now on my imagination-stage Mr. Hastings had undressed. Miss Lewis was lying over the bolster, waiting, clutching a pillow under her face with her hands at the corners. Her face was turned to the side so that she could see Mr. Hastings in all his middle-aged glory. The light was shamefully still on. No—the lamp was shamefully still lit. No electricity in those days.

"Sir?" asked Miss Lewis. "What is that thing?"

"Shh, Miss Lewis," he said. "Young ladies who are about to learn their lesson must not ask too many questions. That is my prick."

"Must it go inside me?" she asked.

"It must. I promise, though, that my young ladies learn to love the motions of my prick inside them."

This was getting out of hand, but I couldn't stop. I was so warm inside my panties that I
knew my orgasm was not far off. My legs wantonly spread, the gusset of my panties pulled aside, and my fingers moving quickly there, all assured it.

* * * * *

Mr. Hastings knelt on the bed behind Miss Lewis. In his hand he had a little vial of oil. He poured some onto his fingertips, and he began to work it into my bottom-hole. No, not mine—hers, Miss Lewis'. I would never let anyone... Who was I kidding? If George ever said...

The fingers felt so wrong and yet so wonderful
inside her bottom. Miss Lewis had never imagined... but now she was going to have Mr. Hastings' big, stiff prick in there. What would it feel like? She felt something warm and slippery pushing there at the little opening. It was soft, but it pushed firmly. She cried out in alarm.

"Quiet, girl," said Mr. Hastings. "I am going to fuck your bottom now." Miss Lewis' face grew hotter and hotter with shame. But there was something so lovel
y about having him there—about the way he'd had her call him "Papa." This was what her papa wanted, and she wanted him to have it, because he was so kind and good to her: teaching her to be a proper young lady.

* * * * *

What was wrong with me? This was always where it went. The little girl, used by her daddy for his pleasure without regard for her own. But paradoxically, it was that very fact that produced the greatest pleasure of all for the little girl.

* * * * *

Mr. Hastings drove inward, and Miss Lewis cried out, "Oh, Papa! It hurts!"

"Quiet, now, and let your Papa do his fucking."

Miss Lewis held tightly to the corners of the pillow. She didn't like it; she didn't like the big prick in her bottom going back and forth. But now she could tell that Mr. Hastings liked it very much indeed, for he had begun to murmur, "Good girl, good girl. Papa likes fucking your bottom." And somehow, strangely, that made her like it, even though she didn't like it.

I couldn't bear it; I had to touch myself there. I groaned as I brought my two middle fingers up against the little opening about which Miss Lewis was learning such a stern lesson. The fingers were already sli
ck to the point of slipperiness from their play between my pussy-lips. I tensed the aperture against the fingers and rubbed firmly with their tips while with my other hand I rubbed frantically at the very center of my arousal, scant inches away.

My fingertips entered there; I groaned again.

* * * * *

In my mind, Mr. Hastings held Miss Lewis' hips firm
ly, bringing her bottom cheeks—still bearing the twelve welts from his cane given earlier that day—against his own loins, then pressed them there so that she felt the sinewy muscles of his legs and their curly hairs. Then she felt his prick pulsating inside her and something warm coming out of it, into her most secret depths.

I was close
... so close. I pumped the fingers in my bottom in and out, imagining they were Mr. Hastings' cock. All the muscles there were starting to clench, and I was headed up that marvelous slope with the cliff at the top that you just throw yourself over and let your imagination soar out into space.

That was when George came in.