The Courtesan's Journal Ch. 6

Some of my clients were most puzzling, like the duchess who loved pain. One woman only wanted to have me watch her masturbate, others wanted to watch me masturbate before them. Some wanted to seduce me, which really amused me.

The intricate scenarios they enlisted to ‘seduce me’ were quite refreshing. I would receive a written set of instructions, giving me advice on what clothes to wear, what name to register under at a hotel, how to respond to a set of lines.

One, who was most satisfactory, was a woman who ‘hired’ me to be her female companion on short vacations. Once the train was in motion and we were securely locked in her private train, she would change into male clothes. From then on, I was to pretend my client was a man, which brought out a hereto-undiscovered part of my profession. Acting. She would run her fingers through my hair, gently unpinning it as I pretended to be a terrified bride on her wedding night.

She wore a phallus strapped under her breaches and some nights she would take the fantasy to its longest form. Those nights it could take hours before she gently pressed the phallus into my ‘virgin’ passage, as I shuddered in ‘horror’ and wept my fate or moan in ecstasy, depending on her wishes. Other nights she would press me onto my back or belly and take me roughly, with few if any preliminaries.

A few special nights she would order me to strip and dance for her, dressed as a harem girl. These were always interesting, since my training did not include this form of dancing and the waltz tutor Eleanor hired had probably never even considered this style of dancing. Each evening was a little bit different than the last, and although her needs were simple enough, they could be rather exotic, too. Unlike many of my dominant lovers, she did not wish to watch me masturbate and forbade me to do it during these trips. If I wished to have sex, I went to her and asked for it. Depending on her mood, she would either comply with abandon or a theatrical nonchalance that made me crazed with desire.

The first of these exchanges was arranged with such complete attention to detail that I rather thought it was like a military engagement. Her letter had been very succinct and very specific. I was to meet her at the train station, dressed in white from head to toe, ready to be the scared innocent bride she desired.

She took care of all the arrangements and it was not long before we were safely ensconced in her rail car. She excused herself for a half an hour, coming back dressed as a well-heeled gentleman of the ton. I had slipped entirely into the character she had provided for me, and so was sitting on the lone bunk, pretending to be apprehensive. In truth, I was very excited and of course, very curious as to this new client of mine.

She sat down on the bed next to me and ran her hand over my hair. Murmuring affectionate endearments, she lowered her mouth to mine. Her kiss was very gentle and I had no sooner thought this was going to be a long night then she began to cup my breast. I drew away in mock horror, pressing my hands over my chest. She chuckled, sounding rather masculine. It took only moments before she leant over me, pressing me backwards onto the mattress. She explained that what was going to happen was natural and she would love me all the more for my acceptance and willingness.

I relaxed against her taller frame, running my hands over the foreign male garments she wore. Her mouth plundered mine as she moved her body against me. I raised my hips several times toward her hips, only to pull back and feign surprise. I may have been working under the guise of an innocent, but my experienced body was clamoring for more. The thoroughness of this client was unparalleled, and I was always amazed at her ability to live the role she had created for herself.

We continued on this vein until I lay naked under her, her mouth sucking delightfully at my breasts while I protested half-heartedly. When her mouth finally lowered to caress between my legs, I gasped and protested again. A few extraordinary movements of her tongue over my nether lips and I forgot the charade. Her arms held my hips tightly as she seduced me with her mouth. I shuddered, arching against her ministrations. It was not long before I came, crying out loud.

She gave me only a few moments to catch my breath before she moved up my body until our hips were even. She kissed me again, telling me how much she loved my body, my response. When the phallus she wore began to press against me, I let my eyes fly open in exaggerated horror. The wicked smile of delight turned suddenly gentle again, as she assured me all would be well.

I bucked obediently as she began to enter me, trying to hold back my natural enthusiasm. I even twisted against her, as if to forestall her entry. It took several minutes until the phallus was firmly inside me as I numbly threw my head from side to side. Her gentle hands caught my head so she could kiss away my reticence. I fought her for some time, before growing quiet again. At this point, she slowly pulled her hips back, then forward again. I gasped at the delicious sensation, forgetting again my role.

Her mouth moved tenderly over mine as she continued her thrusts. It took almost a half an hour before my orgasm came, as if my body remembered the role better than my mind did.

Afterward, I curled up in her arms, allowing her to placate me with romantic poetry. Depending on her mood, we would continue with the ‘honeymoon’ or try a different version the next night. Either way, my handsome client was more than interesting. Despite the many times we recreated her fantasy, it never grew old. Nor was she ever discovered to be a woman. I often wonder what incident in her life had helped mold this scenario for her and of course, if my awkward attempts at acting fully satisfied her tastes.