I feel very fortunate in the manner in which I have been able to experience my life as a crossdresser. As a five foot five and one hundred and twenty-eight-pound male I have been interested in femininity and in wearing female clothing for as long as my memory serves me. This inexplicable internal need was a confusing reality, but one that I felt that I had both an emotional and physical need to follow.
I began by exploring these emotions by secretively dressing up as a girl - in my mid-teens. These mysterious feelings affected me in many ways. I was on a search to discover what these powerful feelings meant. The mirror told me that I had already moved forward in both curiosity and actions.
By age sixteen, I had grown out my longish dirty blonde hair. I was blessed with fine facial features and I also discovered how to use make-up at a very young age. I practiced with it in private, guarded times. I first went out in public as my female persona while in high school! I did this while painstakingly evading the knowledge of my parents and family.
It’s crazy when I reflect on the fact that by age seventeen with both a driver’s license and the use of a car, I found myself driving to the very nearby city of Boston dressed as an overtly sexy female! I had been encouraged by both my reflection in the mirror and by an older male neighbor who befriended me. He had seen me walking the neighborhood dressed up as a girl. He would later tell me that that I looked quite convincing as a female.
Today I was grateful that he never took advantage of my innocence and gullibility. I think he wanted to have sex with me but he was a gentleman, something I would find to be very rare in the world of transgender. He even allowed me to dress in his home and loved to see me in sexy dresses. He wanted for me to model sexy underthings for him but I demurred. I was shy and afraid, but my instincts were at least somewhat decent!
I eventually learned about a place where transgender people went. It was a nightclub venue that I hoped to find some acceptance. It was a truly infamous place that I had heard my older cousins talk about. It was seedy and even rumored to be dangerous because at the time it was thought to be a bit of a drug haven. The attraction for me was that this club was a place where I could potentially be acknowledged as the girl I so loved to dress up and be.
When I finally got up the courage to go there after changing and making myself up in my car, it did not go smoothly, as one might say. Lecherous men made me feel like fresh meat in a wolf's den! Their forwardness had me fleeing in but minutes. Eventually though, I would return and adjust thanks in part - to my neighbor’s confidence in my appearance.
Little did I know that my desire to be overtly pretty and my lust for overtly sexy in mini dresses and heels would result in navigations that would be even more challenging. I realized that I was very afraid of many of these half-crazy men. Being seventeen years old had a lot of built-in naivetés. In time, however, my perspectives grew and I came to understand more about just who the girl in the dress was and who she wanted to be.
I made friends with a few of the transgender girls there. There were crossdressers, transsexuals, gay, straight, and in between folks that frequented the bar! There were also many transgender prostitutes, some of whom I found both funny and tragically unfortunate, due to the constant dangers of their trade.
I would do the things that many of the girls at the bar did. I would play pool, dance to the music, watch the drag shows and enjoy the girls I befriended. I did come to enjoy getting bought drinks. There was constant flattery from certain men. Two months later I danced with an older guy and found that his shocking touch and a surprising kiss would lead to far more than was ever on my personal radar! He would be my first.
While in my first semester of college, I had the suddenly wondrous freedom to dress as my feminine self in my own apartment every weekend. I realized in time that I was sometimes willing to dress myself up in an alluring way for a man - if I found him special. This was truly the new me and I must admit it became very exciting to me!
There were a couple of men I would do this for. It seemed daring and crazy, but it would become quite reasoned. I went from thinking of myself as purely heterosexual to finding that I was quite more. The sensual, sexual role of being a woman in a man’s arms became mind-blowing to me! My sensual, youthful, and alluring appearance helped me become rather popular with the guys. I felt pretty, desirable, and very lucky to have the attractiveness to become a popular gurl at the club.
In my first two years out on the town as Cari, I made a few male friends. Two were special, quality men. One of them I was honored to refer to as Daddy. His dominant nature drew me to him in a most powerful manner. I was taught the delights of submissive sensuality as a boy turned female with the caring guidance of this older, handsome, attentive yet resolute man.
It took a rare circumstance for me to find comfort as a female in a man’s arms, but this man brought out every feminine instinct in my heart and soul. I could now express that I have been a man’s whore as the girls at the bar would say. Fortunately for me, it was mostly a wonderful experience with the two special men who have both impressed me and have treated me very well.
I’ve always had a travel bug. Montreal, Canada became my favorite travel city for many reasons. My first ever trip when I got my license was to see this city. It’s gender friendly, sexy, and cosmopolitan. It has a huge gay village and people are accepting and far more tolerant than in the states. After my first visit, I became one hundred percent female when I traveled there. When I got time off of school I used my saved money to take gurly vacations there.
On a trip there recently I met a handsome man who flattered me greatly. He approached me early in the evening at the bar of a club I like to visit. Turns out that he was the owner of the night club. He ordered me free drinks and told me that I looked like one of his show girls! He asked if I would ever consider entertaining at his venue. I told him that I had done a couple of Drag shows in the past but I found it too nerve-racking and didn’t enjoy it.
He told me that one of his entertainers simply danced sensually in a bikini for a song in the show. I saw her that night sitting with him at his special table and I must admit that I was inspired! I wondered if I would be willing to do that and I soon found myself having a personal goal! I had always fantasized about being a sensual dancer, and the thought of doing so in a public venue excited me greatly also but terrified me at the same time!
The owners name was Phillip and he said I was very pretty and even beautiful. I do love a flatterer! I think I was convinced that I may want to give his offer a try in the future! I had a bit of experience as what one might call a private dancer! My recent Daddy had taught me to be quite the stripper for him!
Phillip and I stayed in touch and he kindly emailed me often. He was urging me to perform in the future at his Cabaret style Club! He wanted to take me for dinner! He had dozens of performers and I was truly flattered. It was an invitation that excited me beyond belief, and I must admit I was practicing in front of my mirror immediately after my trip!
I have fought shyness – when I dressed as a gurl. Being with men as a woman, ironically – I believe, helped to change that. Once I realized how mutually satisfying a sexual relationship could be, the shame turned to pride and happiness. Daddy also used to encourage me to dance for him. In but a bra and panties, I was inhibited and embarrassed initially, but his encouragement brought me even greater confidence! Due to his support, I developed a level of self-assurance about how I saw myself as an alluring and sexual being.
One of my favorite sexy gifts that Daddy bought me during our affair was a green stripper outfit. It was nothing but a web of body-hugging tiny straps that exposed lots of smooth skin! It also came with matching fingerless gloves and I would definitely call it a private, intimate, bedroom outfit!
The strapped fetish suit had but a small covering in the crotch area but exposed the cheeks of my entire derriere. The whole outfit was even more revealing than a teensy, thong bottomed bikini and purposefully didn’t even cover my cute boyish breasts! It left me being as close to being nude as a pretty girl or gurl could be!
Having watched some of the shows at the drag bars in Montreal, I thought that this extreme outfit might be the perfect end result of my potential strip tease style dance performance. When I had danced in it for Daddy, my inexperience showed! I had great difficulty keeping my seven-plus inches of maleness hidden for the female effect! It didn’t matter then, but it would look pretty bad in front of a large audience! Cabaret Mado is renowned as the place for Drag Shows and entertainment in Canada in the middle of famed St. Catherine’s Street. It was a high bar for a young nineteen-year-old!
My outfit needed special attention. The small crotch barely covered my almost always stimulated member. I had a plan to try using a new easily removable type of medical tape to hold it down there in place - should I use this in my performance number. I put this naughty outfit on and you might say I looked close to being naked. I looked at my reflection in the mirror and I looked so girly that it made me breathless!
I soon began to practice regularly in front of the mirrored wall in my bedroom. I found various music and the moment I found the song, it got my juices flowing! It was perfect in its energy and the last lyric “Got to have some love tonight” had just that sexual edge that I longed for! I wanted to be like the song implied and I was determined to live up to being Hot Stuff!
I knew that I could dance seductively at an amateurish level. The times I had done that with my Daddy always shall we say – ended well! Now however, I had a new goal and opportunity. Could I be an exotic entertainer? Could I be an erotic dancer? Could I overcome my shyness and apprehension? Could I do so in front of hundreds of people in the spotlight on a stage?
My routine was certainly a work in progress as I aspired to be outrageously sexy and girlish. The sway of my hips were seductive and my flowing arms caressed my body like I was in heat! With the music always in my head, I began to believe and even feel myself in this role. I felt the excitement and raw sensuality of my suggestively sexual appearance.
Being a very feminine stripper was this mysterious goal that I had only recently begun to fantasize about. Now I believed in my heart, that I had an aura, a mood and the realistic character of a sexy, beautiful female dancer. At five foot five inches tall and one hundred twenty-eight pounds, I can comfortably wear a size four or five dress. The mirror reflected my slim body, narrow waist and my sexy round bum, which screamed femininity to me in my near nakedness.
I decided I would definitely was going to travel to Montreal, I just wasn’t sure if it would include my budding performance. Every night I continued to practice knowing that I was invited by the owner for a week away from now. It was purposely during my week long college break. Would I dare do this? I was not motivated by money as he only implied I would get compensated. It didn’t matter as I was up for doing this as a personal challenge.
With three days to go before I would travel to Montreal, I began to feel more secure. After dozens more takes and practice sessions, I even nailed the bow and curtsy in the end! My confidence had soared, but my reflection was far different than the reality of being in front of as many as the three hundred person capacity of the nightclub. I was so excited and stimulated in so many different ways!
END OF PART ONE
