A Butterfly Emerges

The hard part was next, applying makeup. If I had ever learned anything by watching women it was that it’s better to use less makeup than too much. No use looking like either a prostitute or stereotypical transvestite. I gingerly applied the conservative eye shadow and blush. A moderate pink lipstick capped off my facial transition. I applied some very conservative false nails to my fingertips and lacquered them with a pink polish to match my lipstick.

Finally, I took the cute auburn wig and placed it on my head. I stepped in front of the mirror and was absolutely shocked at what I saw. Staring back at me was a very pretty young woman, passable in all respects. I clearly remember thinking, as a tear gently washed down my cheek, that this was the very first time that I had truly been happy and looked forward to an evening out.

My plans for my first foray into the world of womanhood were modest. I would go out for cocktails and dinner then return to my room. From there, who knew where my new life would lead.

I nervously shut the door to my room behind me as I stepped into the hotel corridor and made my way to the elevator. The elevator dinged, the door opened and I stepped into the elevator, joining a very handsome looking man. I stood in front of him, staring at the floor numbers, but I could feel his eyes looking me over.

I entered the hotel lounge amidst a huge happy hour crowd and noticed that the only seat available was at the bar. I breezily walked past tables of half-stewed stockbrokers and attorneys, ogled with each step that I took. I hopped up on the bar stool and seductively crossed my long legs, revealing just a hint of my stocking tops. I saw several jaws drop and the whispering started immediately. I clearly heard one drink-laden businessman tell his companion, “I’d like to take her for a ride.”

I ordered a cosmopolitan and teasingly sipped it down, leaving traces of my lipstick on the glass. Just as I finished, the handsome man that I had seen in the elevator walked up to me and asked if I would let him buy me another. “Of course,” I responded.