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The Diary of Mistress Penelope


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The more I got, the more I wanted, the more I needed to learn. I craved knowledge. I wanted to know what it was like to be a man dominated by a woman. I met a few masochists but only one sadist-- which was when I learned that ultimately I needed to be in control, and my own pain or torture did not get me off. They were very open about their aberrant or bizarre desires. I tried a variety of domination styles and sought only men who would let me be rough with them. Eventually I couldn't climax unless I was the one in control. I spent much time penning my conquests by flashlight beneath my covers, masturbating to vivid mental images of men I'd subdued and men I dreamed of dominating. It never occurred to me to have sex with another woman-- to that point, it was all about the men and exposing their intrinsic vulnerability. Until, of course, I met Penelope.

I met her on my way to support my friend Natalie's writing skills at a poetry café one night when I was sixteen. I could spot her from a mile away, nonchalantly smoking a cigarette, her jet-black hair tousled by the wind, set against her ivory skin. She gazed out into the distance with a mature, jaded look on her face. As I approached, I made out the finer details of her face-- high cheekbones, her lustrous ruby red lips. There was something so immaculate about her, untouchable, her every movement sensuous. I stirred with longing, surprising myself. Despite my early masturbation to naked images of women, I'd never been attracted to one in real life before.

She turned in my direction, her smoky gray eyes resembling a cat's. Unsure of how to act, I asked her for a cigarette, my fingers nearly trembling as I brought her already lit smoke to my lips, tasting chocolate and coffee on the tip of the filter where her lips had been. I felt my pulse rush inconceivably as we shared the cigarette in virtual silence, staring at each other. Then she tossed the remainder of the butt into the street and grabbed my hand, not waiting for me to respond before she propelled us both through the front doors of the café.

I eyed her delectable figure, her slim waist and round hips, adorned in tight jeans as she led us to a table. I felt like everyone was staring at her-- and who could blame them? She was impossibly gorgeous, her beauty starkly contrasting with the plainness of almost everyone else around her. But there was more, the way she seemed to simply belong there, her movements fluid and easy. There was almost an aura around her that glowed with her sensuousness.

When she sat us down in a darkened, secluded corner of the coffee house, I asked her who she was. As though she hadn't heard me, I watched her grab a notebook from her handbag and then she turned to head onstage. Her hand brushed against my arm, sending shivers throughout my body, as she sauntered to the stage, weaving her way through the crowd. For the next few minutes, everyone stopped to listen to Penelope's words, flowing playfully and meaningfully into each other, leaving us in a collective hypnosis. When she returned to me with a brilliant grin on her perfect lips, I asked in awe, who was she?

Penelope, she said with a shrug and a grin, as if the answer could be that simple. Who was I?

A------, I replied. It was a beautiful name, she replied with sincerity, full of personality. I hated it, I told her honestly, always had, always would.

This prompted a conversation, and before I knew it, Penelope and I had been talking for almost four straight hours, fuelled by caffeine. As the barista announced they were closing, Penelope and I went to her apartment, chatting the entire time. I felt light on my feet, uplifted, my brain full of wondrous words and thoughts and images. The stunning woman beside me seemed to have limitless capacity for knowledge.

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