The Courtesan's Journal Ch. 1

I will begin with explaining that there is nothing extraordinary about me. I was born into a modestly wealthy family of a reasonable social class. Having lost my parents rather early in life, I was shipped off to my grandmother’s where an army of servants and sycophants could ensure my proper education.

In person, I am a tall woman with a dark look about me that has always ensued comparisons to gypsies or the fey. I am somewhat statuesque and have always maintained a wardrobe of jewel tones to highlight my coloring and figure. I matured rather earlier than most women; I have now learned and of course, am left to wonder if my early maturation had anything to do with the course of my life.

I am a courtesan. I make my living by providing pleasure to others. Arranging pleasure, in some instances. The lifespan of the professional-client relationship can be simple or complex, and neither has an accurate idea of how long it will endure. I have had clients come to my door swearing that this visit will be their first and last, only to become the most constant of regulars. Others come and make all sorts of promises about their longevity as my employer, and come only a few times. I have bragged in my more whimsical moments, that not a single client came only once. Double entandre intended.

My reign as a courtesan is rather different than most. As I mentioned above, I was born to wealth and title, using both to their most natural advantage. I have received a wonderful education, both in the classroom and boudoir. What I may have lacked in innocence or naivete, I tend to believe I have made up in tact and determination. None of these set me apart from my counterparts, of which there are many, other than the single solitary fact that my clientele is, and always has been, entirely female. Oh, there was one gentleman client, but when it is explained fully in context, I am sure most would agree that he belongs to a most special category of clients who were never lovers. That does happen, you know. Does that surprise you?

I remember the first time I learned that women could be responsible for their own pleasure. My Grandmother had been staying in London for the Season, leaving me in the capable hands of my new tutor. Eleanor was a woman of thirty, incredibly cultured and beautiful. She had traveled most of Europe and spoke several languages, which is presumably why my grandmother had hired her. Grandmother had also hoped that Eleanor’s worldly refinement would rub off on the very impressionable young woman that I was in my youth. Grandmother was correct in some fashion, as Eleanor most certainly rubbed off on me. Not exactly as expected, of course.

I had been lying in bed trying to fall asleep for hours before I decided to explore the house. Most of the servants had gone with Grandmother to London and so this rare opportunity was too good to resist. I was particularly interested in checking in on my new tutor, who had infatuated me from the first. Clad only in my nightgown, which was ridiculously childish for my age and figure, I made my way through the large country estate to the servants’ wing.

Creeping down the hallway, I was surprised to hear the sound of groans coming from Eleanor’s room. I opened the door a small way, just enough to see her beautiful body caught in the throes of passion, the fingers of both hands hidden between the folds of her cleft. She knelt on her bed in front of me, swaying and arching in passion. She finally climaxed and her naked body fell backward on to the bed, her legs open towards me. I was not so naïve as to be unfamiliar with the ways of sex. We did live in the country, giving me many opportunities to see animals mating. I had even watched an older cousin of mine on all fours in the barn, taking it from a stable hand in a most noisy fashion. My cousin had the same look and smell of passion as my dear tutor did that night.

I walked into the room, closing the door behind me, startling her. Being the fearless chit I have always been, I crossed to her bed and demanded that she show me how to do what she had just done or I would turn her over to the housekeeper. Instead of being upset, Eleanor seemed almost unsurprised to find me there. She sat up on her bed and watched my stubborn body tremble.

Eleanor smiled gently, spreading her legs even further apart.

“That won’t be necessary, Margaret. I’m sure we can come to an arrangement.” Eleanor let her hand trail down her breasts to her cleft. She opened the folds and lightly stroked the petals of her sex. “Have you ever touched yourself like this?”

“Yes,” I stared enraptured as her fingers disappeared into her vagina. “But not inside.”

“Oh, but inside is where it feels the nicest.”

“Can I do that?” I asked, watching as Eleanor continued to finger herself. My Grandmother, as women of her station had for eons, filled my head with all sorts of nonsense about sex. Most notable in these particular circumstances was the raising of my maidenhood to near biblical proportions and importance. I was firmly of the belief that were I to lose my virginity, Armageddon would surely occur.

“In a limited fashion, darling. Too strenuous application will take your precious virginity. I can teach you many other wonderful things.” She took the hem of my nightgown in her hands and raised it over my head. Naked, I stood before her, nipples hard and my cleft damp. I believe Eleanor chuckled at that point, but it might as well have been a purr, as those two intersect when coming from her throat.

“You have a beautiful body, Margaret,” she said. She reached behind my back and undid the ribbon holding my braid in place. Pulling my hair over my breasts, she ran the back of her hands over my full breasts. My body jumped as if I had been hit by lightening. I moaned, letting my eyes close and head fall back as she continued to fondle my breasts. After a time, Eleanor laughed and hugged me tightly.

“Margaret, what a delightful surprise! I thought I would just show you how to masturbate, but I have something much more wonderful in store for you.”

I shivered under her hands and swayed until she laid me down on the bed beside me. Eleanor pressed her body over mine, her breasts pushing against mine. She watched me carefully for several moments before she lowered her mouth to mine. I was such a shy thing, I did not realize that Eleanor meant to teach me more than the subtle art of masturbation; she was going to become my instructor in the art of female lovemaking.

I cannot recall how long she tongued my untrained mouth, but I do remember that at some point she licked down my neck to my breasts. The first stabs of her tongue over my nipple were enough to make me arch against her mouth. When she finally sucked on my breasts, pulling the nipple inside her mouth I cried out, overwhelmed with the feelings my untried body was experiencing.

Still sucking on my breasts, her hand placed mine on her breast. I was so terribly hesitant that first night that I could only think to flick my thumb over her breast. She responded by lowering her hand down my body until it rested on top of my thighs. A slight pressure was all that was required for me to move my legs apart. Her quick hand stole inside and gently touched my mons. I opened my legs wider; gasping at the sensations her hand was giving me.

She rubbed between my outer lips, which only made me strain harder against her hand. “Darling Margaret, you are drenched with passion!”

“Why is that?” I asked her, gasping.

“It means you like what I’m doing to you, that you are preparing yourself for me.”

“I don’t understand…” my confused words broke off as she stuck her finger inside me. My body arched against her violently. “More, oh please, more!”

“Margaret, you have such a strong veil, I could finger you for years and not take your virginity. Do you feel this?” She moved her finger inside me to indicate my hymen and explained the nature of a virgin’s hymen. She cautioned me that unless I was careful to stretch myself, I would have a most unpleasant deflowering. She explained to me about the parts of my sex, rubbing each part until I could tell the difference in each. Her forays deep into my canal to rub my sweet spot made me shake in her arms.

She added another finger to my moist passage, her thumb rubbing like crazy against my clitoris as her mouth sucked violently on my nipple. I could only withstand a minute or two of this until I felt my first orgasm claiming my body. Eleanor only chuckled while I screamed, arching wildly against her hand.

My dear Tutor gave me a few moments to catch my breath before she began again, this time she lay between my legs and secured her mouth to my cleft. Several moments of her quick tongue on my clitoris brought me to another orgasm. Again, she only gave me moments before she began again, this time sucking hard at my breasts while she rubbed them. Again, I came in her arms.

That night Eleanor taught me all the ways I could enjoy my body without breaking my tough little hymen. I received no sleep, and come the morning light I found myself lying under her, her breasts rubbing against my back as she thrust her mons against the curve of my behind. One of her hands was buried under my body, her fingers inside me as the other rolled my nipple between her forefinger and thumb. Her mouth was ruthless on my shoulder, biting me wonderfully. She paced me, withdrawing as I was on the verge of my orgasm several times before she rammed three fingers inside me, causing me to scream into the sweat-dampened bed sheets.

She gave me a few minutes to recover before pulling me off the bed.

“Do you hurt?” She asked, brushing my wild hair over my breasts. “I marked you nicely, Margaret. You must make sure to bathe alone or the maids will think you’ve been making love with the stable boys.” Her thumb brushed over a particularly dark love bruise on my breast and another on my shoulder.

I shook my head. My breasts felt wonderful, only my vagina ached and I told her so. She smiled and embraced me. “Come again, tonight. I’ve more to teach you. Your cunt will be fine after a quick bath.”

Eleanor, as it turned out, was telling the truth. A bath filled with oils set me to rights, so much so that I decided to try out my newfound skills on myself several times before I left the bath. I found that I liked the feel of water falling over my clit as well as the feel of my fingers inside me. I felt my hymen for myself, wondering at its resistance to my probing. I wrote all about my night with Eleanor in my journal and have often chuckled myself at the fact that this was the first entry I had ever made in the book. Each entry, of course, has been a continuation of that first one.

That next night, Eleanor taught me to pleasure her. How to kiss, to press, to fondle. She taught me the vocabulary for what we did, explaining that many women liked cursing, but others detested it. In the next few weeks, she taught me about lingerie and how to wear it for sex and how to seduce and be seduced. Later, she even arranged for gymnastic lessons for me, which made me wonderfully flexible and limber.

One night she opened a chest at the foot of her bed with a key and showed me all the toys and accruements of passion. Most could not be used on me, but some could and I found them delightful. After a careful set of cautioning, Eleanor placed a harness around her hips and set a round phallus to it. She laid me down on the bed, drawing my knees over her elbows. She placed the round phallus tip between my nether lips and rubbed it over them. I groaned and bit my lips in sexual agony. Her next trick was to place the phallus between these lips so that the tip rubbed my clitoris. She continued to thrust carefully, so that it did not enter my body. I came so hard that night; I ripped the bed sheets with my fingernails.

Another night, she placed the harness on me, this time with a larger phallus. This time I was able to mount my dear tutor, delighting in her hoarse screams. That night was a turning point in our relationship, as all vestiges of shyness were now gone.

There were more memorable nights of passion. Lessons about the proper use of her tools, lessons about eroticism and seduction. The courses on positions for phallus play were delightful and Eleanor explained how different positions made for different experiences and how to fix the harness to take the added pressure of many of them.

She even shared with me the story of her own deflowering. She was a penniless, but beautiful young woman being educated in a college on a generous scholarship from a distant relative. One of the limitations of the scholarship, however, is she was not housed with the rest of the students, but rather had to stay with the maids. She was surprised to find out that the maids were holding regular orgies in their cold quarters and one night, one of them seduced her after giving her some wine stolen from the kitchens.

Her first taste of passion was when one of the maids had the other girls hold Eleanor down as she brought her to orgasm with her mouth. Eleanor writhed and struggled half-heartedly, since she had desired to be brought into their games. Soon after that first night, a woman pushed her hand up into Eleanor’s body, breaking her hymen and fisted her to an orgasm, as another two maids sucked on her breasts and another french kissed her.

Some nights Eleanor would be awoken by fingers reaching into her vagina, in which she lifted her hips to receive until she whimpered in ecstasy. She would then fall asleep never knowing which of the girls had awakened her. Nights such as these were her favorites, and the maids made sure to approach her in her sleep often. Fingers were thrust into her vagina from behind if she slept on her stomach. Or if she were asleep on her back, she would keep her eyes closed so the maid making love to her would be anonymous. One night, Eleanor awoke to realize someone’s tongue was in her anus and their fingers in her vagina and a thumb applied to her clitoris. This continued for a while, and then the unknown lover began to thrust her finger into Eleanor’s her anus and vagina at the same time, while tonguing her clitoris until she climaxed.

The night before graduation, they tied her down while all of the maids took their turns bringing her to orgasm while she was blindfolded. In a single night, she was sucked, fingered, licked, fisted and mounted to repeated orgasms. The later occurring since one of the maids had found a somewhat phallus shaped statue in one of the rooms and mounted Eleanor with it until she passed out from the pleasure. She woke up alone, the phallus statue at her side, which she took with her. From that moment on, Eleanor had devoted herself to learning all the ways a woman could be pleasured.