My First Time
A True Story -
By Cari Christi
Me at the young age of 16 just before going out en-femme for the first time "in public". I visted a bar! I was over and under dressed in this very skimpy, short, teasingly sexy, black silk prom dress! How do you spell  I had a steep learning curve coming as they say!
The "urge" or the "need" (to dress as a female) was a driving force in my life as a young teen. In spite of being a good athlete and pretty successful in school and most anything I tried - I always had this fascination and compulsion with wearing womens clothing and "looking" like a girl. It was always seeking private time to dress and practice. Being very resouceful, I had all kinds of collected female things by the time I was sixteen (hidden) in my families basement. When I got my drivers liscence it fostered even greater independence possibilities for me - and just before my seventeenth birthday I hatched a plan to go out in public - dressed as a sexy woman! I was a pretty "clever" and working part time had helped me gather and save for the resources I needed. I even had a "female ID that I had made by a person I knew through work. My biggest expenditure was for my first real "wig" - which I am wearing in this photo. I got a motel room to prepare in - paying cash and hatched my well thought out plan on a Saturday night in June.

It was indescribable how wonderful it was to spend the afternoon shaving my whole body, preparing myself in make-up and trying on my collected clothes. I had done myself up with "the works" - false eyelashes, clip earrings, braceletts, necklaces, silken panties, a g-string, black silk stockings, 4' sandalled high heels and a spectacular black silk "prom dress" that I had made disappear from my pretty girl friends closet! I felt that I looked really good - from the above photo - I think I looked quite sexy - in almost a call girlish way. To me I felt 4" black heels and my outfit were just feminine. I think the woman of the fifties - Marilyn Monroe etc. were a part of me. Little did I know how my overtly sexy appearance would get me in a lot of trouble in the next few hours!

It took me over an hour to even venture outside my motel room. I was scared silly! It was still light out and I was so afraid that I would be "read" as a guy, that I was a bundle of nerves. It wasn't until the sun went down and I knew "the coast was clear" before I almost jumped into my car quite clumsily in my high sandalled heels. Driving was like learning anew in heels. I wondered how safe I was - once almost getting my heels caught on the Gas pedal! My plan was to drive to Jaques - a place that I had heard about from my friends and relatives. Stories of men in dresses on the sidewalks and in the bar intrigued me and I was convinced that it was the only place a "girl" like me could go to. I was even more afraid when I parked in the Downtown Boston neighborhood in which Jaques was located. I was only about 50 yards from the bar but it seemed like miles in heels!

After several attempts to deal with my nervousness I kept getting out of my car but then ducked back in - as there were people on the street at most times. I was so afraid to be seen in this neighborhood when I suddenly saw a "hooker" walk up the street in my direction. She was wearing thigh high boots and white hot pants and only a bra like top. At closer look I realized that the hooker was a guy! His legs gave him away - and I feared my own would give me away in the same way. My black stockings might help though - I thought. But my confidence was ebbing rapidly. I had to go - or "never" fulfill my plan. Finally - I suppose inspired that if a shemale hooker could walk these streets - I could make it as far as the bar! I took the deep breath and off I finally went.

Amazingly I suddenly felt like a great weight was lifted from me. The sound of my clicking high heels echoing from the walls of the brownstone buildings sounded like music. I felt suddenly sexy and I think I even walked with a coy sway of the hips, trying to feel the part of woman. At the door I peered in and walked toward the bar as the door was open due to the warmth of the June night. I sat at the only open barstool as a man to my left grunted and asked the bartender to get me a drink! I ordered a scotch on the rocks - a bit strong for a sixteen year old and quite against the law as well. I suppose they figured anyone dumb enough to be in a Transgender bar HAD to be of age!

My first "time out" went rapidly down hill! The man who bough me the scotch bought me a second and put his hand on my exposed, stockinged thigh! I was shocked! I froze in fear. Did he think I was a woman? I was suddenly tense and even angry. I wanted to tell him to stop but I couldn't. Nothing would even squeek from my mouth! The guy to my right put his hand in my crotch! Suddenly both were pawing me and reaching for "between my legs"! I clamped my thighs so tightly together that there was no way they could go any further when the man to my left began feeling up my bottom! This was all far too much. I grabbed my pocketbook from the bar and fled like a deer being chased by a lion. My car was my refuge. The drive back to the motel was a blur. "What in the hell just happenned?" I wondered. It would be quite a while before I would dare be so bold!

NEXT
Next - I go "out" and become "Cari" soon known to become Jaques (bar's) prettiest and most untouchable tease! Yet I would be moved by a very special...
HOME