Marilyn

Although dressed in southern California casual attire, Catherine's fashion choice did not diminish her regal appearance and demeanor. She sat across the table at a chichi café on Santa Monica Blvd., explaining to me the nature of her exclusive matchmaking service that catered to the needs of wealthy sexually dominant women, looking very much like a member of royalty. Somehow it had come to her attention that I possessed the sensibilities and physical attributes that one of her clients preferred, so she was feeling me out regarding entering into a live-in relationship with that client, not necessarily based upon romance, in which I would be the submissive partner in an extremely kinky sexual lifestyle.

"Marilyn is a very successful producer who doesn't have much time to socialize and meet potential partners, especially ones that share her particular kinks. That's why she has hired me to scout out likely prospects."

Catherine removed a photograph from a large envelope lying on the table and handed it to me. It was a picture of an attractive forty-something woman of Chinese heritage, whose eyes conveyed intelligence, determination and mystery. Based on her physicality alone, she was definitely my type I noted.

"How does her personality compare to her beauty?" I inquired.

"Well, that depends upon what personality traits you find attractive," she replied, smiling slyly. "Overall she's very personable and funny, but she can be very forceful and demanding if circumstances require it, if you catch my drift."

I nodded to indicate that I did.

"What can you tell me about her special interests?"

"In general, she's quite the BDSM enthusiast. Within that context, she's looking for someone to mold into her ultimate sissy slave. Is that a hard limit for you?"

I tried my best not to react outwardly to her question, but inside I trembled slightly as I mulled the potential implications of "her ultimate sissy slave." I may live to regret this, I thought, even as the words No, that is not a hard limit for me left my mouth.

"Okay then," Catherine replied, "I'll set up a time for you and Marilyn to meet. If you hit it off, you'll need to put all your affairs in order so you can move in right away. I know she'll be eager to get started. This is something she's wanted to happen for a very long time."

 

***

 

Marilyn lived in a sprawling unpretentious home on a cul de sac in Brentwood, not far from the studio where she worked. Despite the unique underlying purpose of our meeting, our conversation flowed in a relaxed and civilized manner. The longer we chatted a chemistry emerged that made the decision to move forward relatively easy for both of us.

The photograph of Marilyn that Catherine showed me didn't do her justice. She was a vibrant, beautiful woman in her prime. To my delight, she was clearly pleased with my slender and androgynous body. Indeed, it wasn't long before she gave in to her desire to touch it.

With a beguiling smile on her face, Marilyn beckoned with her hand and implored me to sit beside her. Once seated as directed, she began stroking first my cheek and then my chest. Soon she unbuttoned my shirt before finally peeling it off my body. I was nearly overwhelmed with submissive arousal as she pinched both of my nipples while her tongue snaked down my throat in the most erotic French kiss I had ever experienced.

It wasn't long before I was standing naked while Marilyn circled around me inspecting every aspect of my body, making comments about her plans to enhance this or that feature of it. Standing there sans clothing, while she poked and prodded me and shared her vision for my future as her customized sissy, was exquisitely erotic and exhilarating. When she cupped my testicles in her hand and said "These will have to go" in an offhanded manner, my knees nearly buckled and a jolt of sexual tension caused my genitals to tingle as her words sank in.

While I was still processing that information, she traced a couple fingers along the length of my cock and remarked casually, "I think you will look much better with a pussy." It was somewhat surreal to even consider such a thing, but as I did the idea gained purchase and quickly I found myself embracing the thought of transitioning to a transsexual submissive to Marilyn.

 

***

 

I was indulging in a moment of vanity admiring the results of hormone therapy and the best plastic surgery that money can buy staring back at me from a full-length mirror. Only vague similarities to my former body remained on the naked svelte beauty with perfect 32-C breasts and come-hither pouty lips in that reflection. A permanent stainless steel collar and wrist and ankle cuffs accented my total transformation into Jodi, Marilyn's ultimate sissy slave. Jody was gone forever.

As I twisted my ass to view it in the mirror, evidence of Marilyn's morning ritual with the crop came into view. Neat lines of varying vintage stretched from the top of my butt cheeks to the bottom of my thighs. Just a glimpse of them triggered a submissive thrill in my loins. It also brought forth crystal clear memories of presenting my ass for punishment after orally servicing my mistress, her pungent nectar still smeared all over my face.

The doorbell rang and I stopped what I was doing and rushed to the door to welcome the first group of guests to a private dungeon party. None of the arriving guests were surprised by my nudity because protocol dictated all slaves attending were to be identified by their lack of clothes. Within the hour the party was in full swing and the doms and dommes attending were eager to start playing with the slaves volunteered by their owners for the enjoyment of guests. At this point Marilyn secured me blindfolded to a pillory that held my head at waist level and propped my rear end at a convenient height for fucking and whipping.

For the remainder of the party I was at the mercy of all comers. I was barely settled in when I felt strong masculine hands grip my head followed by a thick hard cock being forced down my throat. I was still getting used to the idea of having sex with men, despite the fact that I was now effectively a woman, so at first the presence of a cock in my mouth was not altogether pleasant. When a cock or dildo was suddenly rammed in my pussy and someone began fucking me in earnest, I became so lost in a state of thrall as I was being penetrated at both ends that it no longer mattered to me who or what was attached to the phallus in each of my orifices.

Toward the end of the party the fifth pussy of the evening was thrust into my face with the expectation that I service it. Despite not being able to see her, I immediately recognized it as Marilyn's and set about thanking her profusely with my lips and tongue for my current immersion into deliciously decadent sexual submission. About midway through my epic pussy worship someone very skilled with corporal punishment began exploring my body with a cane.

Initially the cane was dragged slowly along the contour of my ass and thighs. During this teasing foreplay my entire body began to quiver slightly in anticipation of what was to come. As I vacillated between dread and joy the unseen person in control of that cruel instrument periodically began interrupting its journey with light taps from the cane's tip on the areas of my body that would soon be targets for pain-inducing strokes. When the caning started in earnest, the blows were relatively light, but severe enough to cause pain and redden my flesh.

The first ones were delivered to the bottoms of my feet, the sensitivity of which made the strokes seem even more intense than they actually were. In a progression of increasingly harsh lashes, the cane languidly traversed up my thighs to my butt, leaving throbbing angry welts in its wake. The mystery administrator of my punishment orchestrated it such that I never exceeded my threshold for pain, but rather was able to welcome and actually enjoy it as I continued to pleasure Marilyn. Indeed, the wonderfully depraved D/s scenario reached its crescendo with the near-simultaneous orgasms of mistress and slave. Fade to black.