SM Bondage Feminization Experience by Sub D

An Afternoon with Mistress Cassy

She had me at “I’m Mistress Cassy.” I first met her at an adult fetish party where we both participated in a kinky “parlor game.” The brief encounter was enough motivation for me to seek out this enchanting creature a few days later. After finding her informative website and exchanging several emails, we arranged a rendezvous at her well-appointed residence in Center City, Philadelphia.

Before we met, Mistress Cassy asked me about my interests, previous experience, and any limits or boundaries I might have. On this basis, she suggested a three-pronged session (SM, bondage, and feminization) that was customized just for me.

Dressed in a stunning outfit and flashing a disarming smile, Mistress Cassy welcomed me at her door and ushered me into her residence. After exchanging a few pleasantries, I immediately knew that I wanted more than the one-hour session we had arranged. I was very pleased that Mistress was willing and able to adjust her appointment scheduling to accommodate my request for a longer session. An hour later, I was so glad that I had asked.

Mistress instructed me to disrobe to reveal the sissy garb I had worn, at her request, under my standard boy clothes. I had feared that an accident enroute might result in exposing my “secret” sissy outfit. My anxiety was, however, a small price to pay for Mistress Cassy’s approval –- not only of my wardrobe selection but also of my willingness to wear it enroute.

Mistress completed my ensemble by fitting me with a pair of wickedly high heeled shoes and affixing my blonde bimbo wig. She finished my slutty look by outlining my pouty lips and applying a generous coating of ruby red lipstick to render them suitably plump for the central role they would play during our session.

Ready for play, Mistress guided me to her milking table, where she positioned me on my hands and knees for her inspection. Meeting her standards for cleanliness and “easy access,” I was directed to lie on my stomach, blindfolded, and fitted with sound-blocking earphones. What ensued was a variety of touches and textures that can best be described as tantalizing. They became progressively “bold” and increasingly arousing. Using a variety of gentle lubes, heated lotions, and probing toys of various sizes and shapes, Mistress “explored” my man pussy. Her probing included a delightfully challenging game, which Mistress introduced with a devilishly seductive whisper: “How many fingers can you take?”

Temporarily halting our table play, Mistress escorted me to the room-length, floor- to-ceiling window that not only overlooked the busy city street below but also allowed an unobstructed view of the multi-story office building across the street. Mistress fastened a huge dildo onto the glass and instructed me to show her what my pretty lips could do -- but not before she had opened the shuttered blinds to provide a clear view for pedestrians below and for office workers across the way. It was both exhilarating and humiliating as I sucked the massive cock, with Mistress describing how the office workers were surely giggling with delight at this unexpected X-rated matinee during their usual ho-hum coffee break.

Back on her milking table –- this time on my back -- our play time quickly became more intimate. Mistress remembered what I had told her about my perky and extremely erogenous nipples, and so she applied suction cups to render them longer, harder, and even more sensitive. Soon, she straddled my face, her soft smooth thighs pressing against me, and her sweet juices every so close...all that was needed now were a few rhythmic strokes from Mistress to produce the most explosive orgasm I have ever experienced. Convulsing in blissful submission, Mistress covered me with a warm, soft blanket until I recovered.

Given Mistress Cassy’s exquisite attention to detail and her carefully planned sequence of different activities, I wasn’t surprised that the entire experience was one of a lifetime. I hesitate to give Mistress Cassy my highest recommendation though -- only because I would (selfishly) rather keep her all to myself.