Letters from Lily
I remember it vividly—the first time I met Tia. I remember the sweat on my body as I anxiously drove across the interstate toward my destination, a lavender butt plug nestled tightly inside me, encased in pale pink and white polkadotted hipster panties. Still living timidly under the guise of a straight boy, my appearance was otherwise rather disheveled—a pair of tan corduroy jeans and a t shirt covering my mostly hairless body, and a boyish curly crop of dirty blonde hair atop my head. Thin black framed glasses beset over my eyes, which could only watch as the highway disappeared behind me and white cotton ball clouds drifted across the blue sky. It was February. The frost was beginning to fade—the death of winter giving way to the cleansing showers of spring. And like the flowers, like the seasons themselves, I was changing—a subtle but monumental shift of my being unfolding as I inched closer and closer. The anticipation hung thick in the air as I teetered between unbridled excitement and paralyzing fear.
“Should I turn around?”
“What the hell am I doing?”
“What’s wrong with me?”
Questions rife with doubt and shame swirled about as I writhed quietly on my plug, feeling the warm sensations of pleasure emanating from the fullness within me. A gentle moan escaped my lips, curling into a soft smile. The subtle sensuality of the moment centered me—reminded me of my truest desires. Beneath the ragged threads of my constructed masculinity a profound longing was finally emerging from its dormant state.
You see, back then, I was not the woman I am today. No, I was but a fledgling, a blank canvas with a glint of vast potential—a fearful little girl wrapped in the clothes of a fearful little boy. I knew not who I truly was. I could not see the feminine essence within me just aching to spring forth like spring chrysanthemums.
The hotel was situated off one of the main roads, guarded by a long half circle of trees so the back of the building was invisible to passersby. By the time I pulled in, the sweat and anxiety had reached a fever pitch. I sat in my car, staring straight ahead at the innumerable windows dotting the front end of the Holiday Inn. The tides of the inner battle were quietly turning. Beyond the safety of my Lexus, there was no going back.
And still, with the fullness of my purple plug wiggling around in my little canal, I opened the door and got out of the car. Greeted by a soft wind rustling past the trees, I walked forward to my fate, subtly swishing my skinny ass and hips back and forth, my ears filled with the sound of blood surging through my throbbing heart. For a moment I stopped, an angry, fragile voice telling me to turn around. But the girl in me heard none of it. She knew exactly what she was doing, so I let her take the reigns. And she led me through a maze of hallways, past ice machines cackling as I passed by—until finally there I stood, my breath heavy as my heart, raising my shaking hand to knock on the door which seemed to tower and vault over me like tall shadows in an alleyway. And before the anxiety could take hold, the door was open. There before me stood Tia, entirely unlike the character in the photos—wearing black sweat pants and a comfortable t shirt—a burly man with rugged skin and a disarming smile. Standing in front of him, I felt small, my eyes hanging demurely towards the carpet, my body tingling with anticipation as he stepped aside. The point of no return had passed. I swallowed what little resistance there was and walked through the doorway—the sweet aroma of cosmetics greeting my nostrils. Breathing in the room with its red curtains and white floral couches, I swirled around to see Tim smiling at me and holding a thin shred of black lace panties. Something about his eyes drew me in—a sense of knowing—a fantastic vision playing out before him. Whatever was going to happen, I was in his hands now.
(To be continued)