As a petite, pretty, and now fairly confident young transvestite, I feel fortunate to have discovered so many things about myself. I am proud to have a slim, smooth and well-exercised shape. I have longish streaked blonde hair and my goal is to always develop and improve my feminine elegance.
My friends tell me I possess a very strong believability in my appearance as a young woman. I think it is due to the constant experimentation and hours of practice that I joyfully spend in front of my mirrors. I have over two dozen size three through seven dresses. People seem to always say that I look great in them!
My personal pride and my well-practiced self-assurance help to make my ventures in public a very positive and exciting experience for me. I have spent well over a year dressing as Cari out in public. I spend almost every weekend with enough confidence to be seen as a young woman in specific bars and nightclubs in my home city of Boston, each Friday and Saturday night.
At eighteen years of age, I am perhaps a bit ahead of most gals in experiencing the transgender world. I used to find that I was shocked to feel that there were times that I found myself mysteriously attracted to certain guys. It took a long time for me to explore these conflicting yet powerful feelings.
A lot happened in this first year out as a lady in public. I was constantly ogled and chased by all types of guys while naively dressed way too alluringly than I should have been. My friends told me I often looked like an elegant but almost blatant-looking call girl. I was addicted to extreme femininity as my look, simply because of how good it simply made me feel.
I found myself often talking to older, somewhat elegant, well-spoken men. They seemed less aggressive and more of the type of guy that I felt most comfortable spending time with. It was both confusing and often very exciting to experience and try to deal with these new feelings. I was always overly cautious and found myself staying in safe, non-sexual situations at all times.
I was now going to college full time while working thirty hours a week. I lived off campus, having the ultimate freedom for a dedicated crossdresser. I did however always make sure that my school always came first. The busy, hectic nature of the full learning/working week almost always inspired my relaxation on the weekend.
My second priority was that I had to fill the need to feed my true hobby and passion – which was dressing up as a woman. The transgender world is far from an idyllic or perfect place. Fantasies are often best left as just that. The dangers are too real. However, I just loved everything about dressing up as a girl. I took the risks and became acutely aware.
I learned, even in my mid-teens, to use great caution. I was aware that too many people that I have met have major difficulty with many aspects of the “LGBT” community. I was aware of girls like me that met violence and sadly more. In many ways, I was foolish to venture out in public dressed, but it was a need I couldn’t deny.
As a result, sorting out genuine and trustworthy people is just plain difficult to do. Drugs and prostitution make the environment almost toxic at times as well. It is really not as glamorous an environment as it may seem to those who have never experienced it.
One night, though, along came a quite handsome, smooth-talking nice, and almost normal guy! He got my attention because he was elegant and refined. He was very much older than me. I liked him but my fear caused me to have to meet him at the club several weeks in a row before I developed trust in him.
During that time, he bought me dozens of drinks. We danced together at times and we became kind of an unofficial couple. He and the bartender at the club we frequented convinced me that the idea of our dating could be “normal and innocent.” Eventually, I gave in. My naiveté and curiosity led to us having a nice dinner date. Being escorted, made me feel so very feminine, so happy and almost normal in my role as a girl.
After dinner, we had drinks back at the club. Things suddenly turned in a much-unexpected direction. My first kiss from a man moved me beyond anything I ever imagined. It soon led to drinks at his home and the eventual loss of my panties and more!
Suddenly I - the pretty boy in dresses - had a boyfriend! In the next six months, I learned that pleasing a man was every bit as sexually and emotionally rewarding as being pleased by one. I’d gone over to the other side yet I viewed myself as simply a heterosexual girl, who was dating a hetero guy.
I found being a man’s girlfriend and lover was a far better experience than I could have ever dreamed! I loved everything about being submissive and being a pleaser for a man. Being made love to by a man validated my feminine persona and inner woman more than anything on the planet.
As good as my life was in the role of being a man’s mistress, it soon became very complicated. He was married which was perfect for me but our difficulties began when he wanted so much more. Ironically, I was shocked to learn that this meant that he wanted to leave his wife for me!
This was just way too intense for me. In spite of how attracted I was to him and how very much I loved being his exclusive lover, I felt we needed to part as a couple. Unfortunately, dodging him began to drive me crazy. He began to show up whenever I went out to the clubs. I had to reject him constantly and I needed a change and a break from the Boston dating and transgender scene.
My getaway plan was to take a week-long trip to gender friendly Montreal, Canada during my college spring break. It was a five-hour drive but for me yet it is a perfect escape. I’d been to Montreal as a kid on trips and twice with college friends. I had also gone once for a long weekend as Cari and it had been the best vacation of my life.
The only problem with a crossdresser’s getaway to Canada is customs. It is very weird - if stopped - to explain my wigs, high heels and dresses in my luggage at the border! My friends suggested telling the border agents that I did drag shows for a hobby.
A friend of mine did shows with a transgender charity and fundraising group. I borrowed their business card to show my membership. Since I have volunteered and done some lip-synching shows at times myself.
Fortunately I had no problems this time at the border. It’s always easier going into Canada. Logistics aside, I finally got into my hotel room and made the full stunning transformation into my favorite alter-ego Cari.
Finally, my almost six weeks of winter frustrations were coming to an end. I find peace in Montreal for many reasons. This is the most non-judgmental city I know. Sensuality is valued and I’ve never experienced a more open and accepting culture.
Montreal is both a sophisticated and cosmopolitan. French women are usually slim, well made up, wear high heels and love to look very attractive. They dress impeccably and almost always in elegant feminine clothing. Getting dressed to the nines here is normal!
Perhaps best of all is that the LGBT community here is front and center and even celebrated! Many French men think a “girl with something extra” is a gift from heaven! There is just no place like Montreal that I have ever heard of. I’d been asked out many times by some very attractive men on my previous trip there. I rejected them due to my prior inexperience and safety fears.
Montreal immediately presented me with a scary situation that I will never forget. It was a circumstance that could have been one of the biggest mistakes of my young life. When I arrived, I got all dolled up early. In setting daylight I decided to walk from my car to the club the long way, to enjoy the warm, spring night air while in my sexiest mode of dress.
I loved how I found myself very comfortable out in public here. Walking through the busy city streets caused me to be half lost in the arousal of being so femininely and attractively dressed. I so loved walking in my five-inch high heels anyway. Now strutting along the sidewalk downtown on St. Catherine’s Street was pure joy.
I was thrilled by my daring and naughtiness wearing but a teensy, upper thigh length, white skin tight, V-necked spandex mini dress. It was just another of the many borderline hookers like dresses that my friends suggested were a bit over the top for a girl who was in no way a call girl! I loved attention as a sexy girl but now I felt so free to be me in this city.
This cute little mini dress just screamed for people to look at me and even stare at me. It. I’d describe it as scandalously feminine. It is perhaps way too revealing of my soft smooth skin. I was enraptured with myself knowing that I looked incredibly petite and slim and so much like a quite sexy call girl wearing it.
Suddenly as I walked strutting in my high heels, a lot went wrong. I looked up to see no less the thirty parked motorcycles and their edgy looking drivers standing immediately by the sidewalk ahead of me. Oh my God was all I could think. What should I do now - I fretted.
Dozens of these rough looking bikers were standing on the very sidewalk on which I was walking. I contemplated a quick U-turn but felt it would have made me stand out even more. I quivered in sudden fear. I thought briefly about running, but my white leather, five inch high heels would prevent that!
My impulses and indecision told me to just keep moving. Now with my heart in my throat, I sauntered carefully trying to make my wiggle and my erotic hooker like walk and appearance - less exaggerated. In my outfit, that was pretty impossible! I looked down at the sidewalk fearful, yet being careful strutting in my very high heels.
Now I was even afraid to look up. I heard a comment in French. I glanced sideways and I realized that I was getting cat calls from the bikers. I was shocked that they seemed complimentary! I was not being threatened or scorned. Many of the leather-clad bikers were genuinely smiling at me! Even though I looked more the part of a Montreal streetwalker, they approved of me with whistles and cat calls!
With a deep breath, I finally realized I was indeed safe! Suddenly my confidence surged as I walked onward and away from them. Thrilled by my safe escape and daring, I even wiggled my round derriere in an overtly sexy manner before I turned back at them and smiled. This is just one of many reasons why I truly love this wondrous city! In other cities, I could possibly be dead!
In Montreal, I can dare to be myself far beyond what I ever would in my home town of Boston. I had not felt this free in what seemed to be ages. In Boston, people know most everyone, especially in the smaller closed environment of the two transgender clubs I frequent in Boston. Here it was completely different and no one even knew my name.
Now I was feeling even more-sexy and even sexually aroused. I felt horny and my manner of dressing made that indelibly clear. The teensy white minimal spandex mini dress left nothing to the imagination. It exposed my shoulders, upper breasts and literally every inch of my legs. It was almost like having a body clinging little stretch towel wrapped around me after coming out of the shower with only a couple of straps to hold it up!
I gleefully entered Le Pyramid Lounge on St. Laurent Street and went to the bar. I felt like every eye was on me and I loved it. I sat and before I could order a drink one was being sent to me!
Being happy hour the bonus was two for one as well! I thanked the man across the bar with a long distance toast. For some reason, the drinks both went down a little too easily and I was soon sent two more. Soon another round was being bought for me as well.
I easily downed the four quick drinks in minutes. I knew I shouldn’t drink so much on an empty stomach. As quickly as I finished the fourth, more were soon at the bar at my barstool! If I wasn’t careful I would be losing personal control but already the events of the night soon were becoming a blur. The man who bought me the drinks invited me to another club. I let him take me by the hand.
oOo
The next morning I woke up in my hotel room bed in a quite confused and blurry daze. I had a dull headache and I had to pee in the worst way. Slowly as I awoke, I realized that I was very hung over. Last night had been something very different and more than odd, to say the least.
I quickly realized that I was still wearing my skimpy dress. I was still even in my high heels! This was not good. What kind of night must I have had? Slowly things began to come back to me that I didn’t think could be possible or real. My night could not have been as bizarre as I had just thought. It just had to be a dream!
Getting up from under the covers was a struggle in my high heels. I kicked them off under the covers and went to the bathroom. I then realized my panties were gone. Little did I know that there would be more signs of an evening that I would perhaps be best to forget and certainly not recall!
I got a drink of water for my hangover and took two aspirins. Slowly things were coming back to me some. As I sat to pee like the girl I was dressed as, I felt a sore spot on my bottom.
When done, I went over to the mirror. I lifted my dress exposing my bum. On my right ass cheek, there was a bright red mark. A closer look clarified my confusion. It was quite unmistakably a handprint! My naked bottom had quite a spank mark. Suddenly I realized the crazy dream I thought I had last night was perhaps not a dream at all!
What had happened last night? I slowly took off my dress and heels in desperate need of a shower. Where were my panties? I looked in my bed and found nothing. My mouth and throat felt a bit sore. As my awareness began to increase, the blurry events of last night were staring in return - in spite of my aching, hungover, still slightly spinning head.
Before showering, I decided to sit down and try my best to recall the events of this last night. I know I had left my room headed to a favorite Transgender Night Club on Rue St. Laurent. I remembered the joy of walking half naked in my naughty dress and high heels in the cool August evening air. I then remembered the bikers and I smiled to myself about how bold I had been.
Then I did also remember meeting the guy who had bought me several drinks during Happy Hour. I recalled that I had gotten literally double the drinks and drank at least six. That was apparently the beginning of what my head and body were now paying for.
In frustration and in my desire to look even more feminine, I had been starving myself and dieting. Having eaten so little before drinking so much had turned into a formula that was not a good one. At five foot five inches and one hundred thirty pounds, I had very little body weight to absorb alcohol! I’d lost even a couple more pounds recently and my slim smooth body was not up to the task of keeping myself steady.
I then remembered that the man suggesting we go to another club. It seemed like a good idea because the club on St. Laurent was very quiet on a Monday night and didn’t even begin to get busy until midnight. I think I drove him in my car – or at least I must have. That was terrible judgment!
I rarely give control away of my safety ever. I find Montreal is such a safe haven as a transvestite. Unfortunately, I was allowing myself to lose complete control and awareness of my surroundings. I also seemed to be doing this quite unconsciously.
My weeks of starving myself down to model-like thinness and my skipping both lunch and dinner didn’t help. I had lost control in a way that I never, ever wanted to let happen. I then remembered how strange the night began in this up-scale gay club on St. Catherine’s Street.
We had gone to a large complex called The Sky Club which is a huge multi-level club facility in the middle of the famous Gay Village. The club offers everything from dancing to drag shows, even including nude dancers of every kind. It is a busy often wild place with mood changes depending on the room area of the club that one chooses to visit.
The club is home to every type of person. There are rooms for all types. There are areas frequented by Lesbians or for Gay men. There are multiple dance halls and even areas that serve food. I recall vaguely being at a high table on a stool, talking to the man who bought me drink after drink back at the cabaret club. That’s when things truly began spinning out of control.
Then I recalled how it had all began. I remebered it like I was still there! Now I was seeing the entire night inmy mind. Almost like a movie, I felt like I was now watching what I had failed to see and do!
oOo
When I leaned forward on my bar stool I had felt a brushing against my derriere and at first thought it incidental. I was drunk, horny and feeling naughty. I was getting a little frustrated with the man I was with. He didn’t seem in any hurry to take me back to my hotel. I was already over the edge and in sexual want and need!