The Courtesan's Journal Ch. 3

When my grandmother was revived, I was quickly dispatched to a boarding school for young women. Little did any of us know that all her plans were for naught, as I was surprised to find Eleanor was the new Head Mistress of the school, having known where Grandmother planned to send me from her first day a my Tutor. Her glorious hair was pulled back sharply from her face and the dour garments the school required her to wear made her really quite intimidating. In her eyes, however, was the same sparkle of wit and passion that I had come to adore. I believe that first morning at the school was when I fell in love with her.

I later learned that several of the maids had tearfully admitted that they too were my lovers, which caused my grandmother to have a severe heart attack, which left her weakened. If I had felt anything for that cold, cruel woman before that, I certainly felt a tiny twinge of guilt then. I tried to reason that at least I was a man and hadn’t left the maids pregnant and so my grandmother should at least be thankful for that.

Being the headmistress was a wonderful position for Eleanor. She had been able to get several large new toys, several of which were mechanical. My favorite was a machine that vibrated a small wand. Eleanor had several attachments for this, which she plugged onto the machine and set it going on my clitoris or even just inside my vagina. I experienced orgasms at every level of its intensity and used it often when alone.

One very memorable night when all the girls were gone for the holidays, Eleanor gave me alcohol for the first time. (I of course had not been invited home, as my grandmother was afraid I would continue seducing her servants.) We lay around drinking; lying naked together on her bed, taking turns masturbating for the other. I adored watching Eleanor use phalluses on herself and could barely wait for my turn to masturbate. After some time, she stopped me and called for a new lesson.

She strapped me to the bed on my stomach, the vibrating machine’s wand between my legs at my clitoris and proceeded to turn it on low. The steady vibration was driving me crazy and I was completely surprised by a well-lubricated fingertip being placed against my little rose. Eleanor gently pushed until she gained entrance, soothing me with words of instruction. I bore down on her finger and was able to take her entire finger into my virginal rose. She gently moved within me for a few moments before withdrawing. I was very surprised when she went to do it again, this time with a very thin phallus. She explained that I would enjoy it and so once again, I bore down and the slim phallus entered me. She turned the machine medium and then to high, causing great wracking spasms of my body as she moved the lubricate phallus in and out of my rose. When I was at the very brink of orgasm, she thrust the phallus into me violently, causing me to scream as I came.

I reciprocated for her later that night, using a new harness that allowed for two phalluses, one for her vagina and another for her rose. The vibration machine whined at her clitoris and her screams of pleasure were fantastic. In later experiments, Eleanor strapped the thin phallus to her harness and gently inserted it into my rose, pressing down with her hips in a thrusting manner, while simultaneously fingering my vagina as the vibration machine buzzed away at my clitoris. Although I had violent orgasms when she did this, they were so intense I rarely requested the combination and so Eleanor saved it for very rare occasions.

Eleanor instructed me in the fine art of discerning a woman’s preference. Within my second year there, I was seducing the cream of London’s finest young women with an almost alarming pace. Close to half of the student body would ultimately find themselves in my bed, many I merely pleasured but on several occasions I deflowered my fellow classmates after their repeated demands and bribes. I soon learned that if I allowed my attention to wander away from my lovers, they would soon shower me with gifts. The gifts allowed me to create my own collection of sexual toys and accessories and I was always amused by their insistence that money could overcome my feigned reticence to take their virginity.

Most of the young women who were my lovers were as casual as I was about sex. A few were not, although all realized I could not be had by only one woman. I would lie in their arms, harness still affixed to my hips, phallus still moist with their wetness and listen to them praise my beauty and stamina. Some would offer me greater allowances with their bodies if I would only be their lover. Some would masturbate me to orgasm, then themselves, asking nothing of me but to witness their deeds. Others promised me gold in exchange for fidelity. These were always the most laughable, since I had long since realized that as soon as I trained one girl in the arts of love she would be off finding another girl to teach them to!

After seducing each new student, I would go to Eleanor who kept incredibly specific notes on each woman. Our book provided me with the specific nature of each woman’s likes and dislikes in bed. The recitation and note taking would enflame us both so much, that we always ended up tangled on Eleanor’s sheets, pleasuring each other until dawn. Years later, it and others like it would be provide a charming reminder and refresher course when they came to me as clients. At present, I have several dozens of these books, with which I shall do with them I hardly feign to know.

The day I received word that my grandmother had passed away, I went to Eleanor and asked her to take my virginity. I explained that without my grandmother’s determination, I would not marry, having been secured a very nice fortune at her death, most notably several properties. Eleanor was delighted and strapped on a beautiful new phallus for the task. She made sure to bring me to orgasm several times, before setting me up with the vibration machine to my clitoris, set to medium.

The first time I felt my vagina invaded by the smooth width of the phallus, my eyes flew open in shock at the pleasure of it. Eleanor thrust against my hymen gently, getting nowhere and causing me great discomfort. The width of the phallus filled me wonderfully and I moaned from the pleasure of it. She removed it to add oil to it and again flexed her hips, sending it into my tight little passage.

It took several extremely hard thrusts to penetrate my hymen and I screamed in agony and ecstasy both as I came. Eleanor, of course, knew no mercy and continued thrusting into my wounded vagina until I came again, this time raising my hips to her thrusts. I screamed her name and fell exhausted to her bed, Eleanor's name on my very satisfied lips.