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Events in our lives can often change us in ways we never expect. In my case I certainly felt different as a young boy. I possessed very real, mysterious, unexplainable, emotions that I can describe only as feminine needs, in spite of being athletic and quite normal in appearance. These internal feline longings and desires were intense and drew me to all kinds of feminine things.

I knew that I loved to feel like and even look like a girl. In my youth I would secretly dress up like one though my family was mostly unaware of my secret. These were emotions that it seemed like I needed to hide and keep repressed. When I got older I knew that I wanted to find the freedom to discover what this all meant. I was very aware that my feminine side was a driving force in my heart. I’d secretly collected a large cache of feminine clothes knowing in my mind that my desires would somehow become more extreme.

I felt deeply that I needed to seek out the why in why I felt compelled to do this. I enjoyed all these feelings so much. I wanted to see if I could enjoy this delightful side of myself in a manner that was less clandestine. With little knowledge, I would soon seek to learn about these wants and desires without any particular plan or road map. I guessed that I should allow my instincts and my desires to guide my future explorations. Perhaps I could dress up as a female and allow my natural and even intense curiosity to take me where it would all go. I was certainly inexperienced and naïve.

Because I practiced cross dressed secretively throughout my youth, by age seventeen I had already become a very convincingly believable girl when I chose to transform myself into a female. I had spent hundreds of hours clandestinely experimenting with make-up. I was growing out my longish, full, blonde hair. I kept myself almost wispy thin at one hundred thirty pounds and my short stature at five feet five inches tall helped what I hoped could lead to my eventual believability as Cari, my feminine persona!

As my first year of college approached, my ever growing secret collection of sexy alluring dresses, high heels and accessories were my pride and joy. The question was whether I had the courage to become my feminine alter ego and to do so as I had fantasized, in public! I knew deep down in my soul that it was only a matter of time and opportunity. I suspected I had the both desire and the will to find the resources to make this fantasy a reality.

In August, prior to my freshman year in college, I moved into a quiet, reasonably priced one bedroom apartment in Boston for college. My family supported this because I worked a part time job - making me able to cover the rent. Even more purposefully, my true reason for getting the apartment wasn’t so much as for college as it was so I could explore my confusing yet excitingly motivating feminine side.

After but two full days of all out experimentation dressing up in my new place, I soon found myself shaving my body all over. The feeling of the hairless perfection of my lithe sexy body was euphoric and sensual beyond belief. Now I knew that I would be able to explore the world daringly dressed fully as a “girl” in public.

I would soon begin to discover things that I never could have imagined. The world of crossdressing was so new. The idea of multiple sexualities and the concept of transgender was amazingly complicated and yet it was all very fascinating to me. I needed to see what it would be like to be Cari the female side of myself in public!

What I was about to learn about myself would be well beyond anything I could have ever envisioned, even in my wildest and craziest of dreams. I was so enamored with my girl side. I felt more than able to pass as a girl – at least at night. Now it would be about courage and having the common sense to do this safely.

I was in my own personal heaven with my new independence and privacy. I had a reliable used car and easy access to downtown Boston. I was now suddenly free to be all of whomever I was. When I moved in, I realized just how much of an accumulated cache of female clothes that I had kept hidden back home. All these female garments almost equaled my male clothing in amount! Thankfully my new apartment had two closets. Perfect for the guy going to school and for the girl who hoped to go out in public on weekend nights!

By mid-August I had already twice daringly visited a rather notorious alternative bar in Boston as my femme self. I was even learning to drive with my high heels on in my car. I knew I would soon visit this scary but transgender accepting place again. In doing so I so wanted to be as pretty and as believably feminine as I could make myself up to be. I always hoped more than anything that I could even look beautiful as a girl.

Beauty and extreme femininity was always my ultimate goal for my look and my appearance. My curiosity and intense interest in all things female had given me both a good eye and an already mature skill set in make-up, hair, dresses, heels and more! Thankfully I am blessed with an almost perfectly feminine body with just some subtle muscular hints due to having actively participated in athletics in High School.

Now that I had successfully dieted myself down to a slim and trim one hundred twenty seven pounds I looked marvelous in my mirror! At five foot five inches of height, I had the right size and many basic physical traits that could enable me to become a passable and perhaps real looking gal.

My new second part time job – was at a wig and women’s clothing store in Boston. This store helped give me everything I needed to become the femme fatale that I hoped to be on the weekends. I practiced make-up in my quiet times at home in my apartment and loved doing cleaning and housework dressed as my pretty, feminine alter ego Cari.

My excitement gushed as now that I was on my own I could fully shave my entire body into pure smoothness and feline perfection. The feeling and sensation is indescribably erotic to me. One of my co-workers at the wig shop was also a transvestite. Stephanie was her name and she soon became an awesome and valued friend. She became my connection to the night time transgender world and to what I felt was almost an affliction for me!

Steph also told me about corset training, an effective way to narrow my waist. On her advice, I bought a strong, waist cinching boned corset from the store and immediately began wearing it. It had strong draw strings which I would pull and tie firmly to narrow my waist. I slept in this tight corset at night, and wore it as tightly as I could whenever I was home.

This practice worked effectively and in short time brought my waist down to a teensy almost wasp like twenty seven inches! I must admit that even when wearing the tightest of little dresses, my petite body now had a very convincingly girlish and even delicate shape. Remarkably when I practiced walking in high heels and a dress I appeared – at least to myself - to be almost one hundred percent female. At least I was smitten with her! I was definitely in love with my reflection and my feminine self!

There is a huge learning curve in make-up artistry, hair, wigs and feminine illusion. My knowledgeable friend Stephanie became my consultant and mentor. She skillfully made me up one Friday night at my apartment. We were both stunned when I added blonde hair extensions to my already longish blondish hair.

The reflection of myself in the mirror shocked me so much that I saw a very real young women in front of me! My artistically created feminine face and decidedly female appearance had me beside myself in excitement, disbelief, and even lust! I was genuinely pretty and when my friend Stephanie kindly said that I was actually not just believable - but beautiful, I wanted to believe her!

Stephanie was also very smart Gal. She understood the transgender scene well and intimated that there was a lot more for me to learn about what she called feminine life. She always kept telling me with a tone that sounded like a warning - that I was attractive to a fault. I never knew quite what her expression really involved. I would however come to understand a lot more about she meant a few months later!

Soon I began practicing and experimenting with my new make-up skills regularly, taking advantage of my spare time in late summer before my classes started. In late August I again returned to the alternative lifestyles bar where there were many transvestites, transgender gals, gay folks and straight people. In a teensy tight fitting dress, believable make up, and long blonde tresses, I always seemed to catch the attentions of many of the men in the bar.

I expected acceptance but I was shocked and frustrated that I now found myself being too often being literally ogled by some of the men there. This was not in any way what I had expected. I was learning the hard way. I just wanted to be out as me – Cari – and to be able to enjoy the female side of myself while in a sexy, alluring dress!

Soon Stephanie would become my wing woman there. The friendly and helpful bartender Johnny was also a huge help. Being new and naïve, I needed all the defenses I could get! Johnny would look out for me by warning me about the specific crazy and treacherous folks who attended this Star Wars like bar! This bar was notorious for almost every bad, dangerous and crazy practice imaginable. There were drugs and prostitutes of every kind imaginable, but at least I was accepted as a Trans girl there!

Fortunately with Stephanie’s help, I was also gaining confidence in my female appearance and fem persona. I was not attracted to the guys and I only occasionally talked with any of them. I was so often aghast and repulsed by how hard they came on to me and in such sexually forward and even rude ways that the girls were my safe haven. I truly sympathized with the plight of what a pretty, sexy woman has to go through!

Stephanie said my overtly sexy appearance was definitely made me look like - a high priced call girl! When you go out to a bar his one - like I always did in short, tight, skin exposed dresses, five inch high heels and sensual perfume, I should have known better! It showed how truly naïve I was - and in so many different ways.

I did love my extremely feminine call girlish appearance though. The teensy dresses, five-inch heels and bright red lipstick did make a rather stunning impression! Ironically I didn’t crave male attention in any way. I did like being noticed though. More than anything, I just loved looking sexy and feeling very, very female. I tried to ignore and even prevent the men’s shameless forwardness toward me yet the attentions at least made me feel attractive and wanted.

In September on the weekends, once college classes started, I’d visit the bar every Friday and Saturday night. My weekends as a woman were rather quite exciting to me in spite of the difficulty of avoiding the often overtly aggressive men. In spite, I felt incredibly feline and even erotic while sensual dressed as Cari. I was growing more comfortable in my high heels and teensy dresses!

I gradually began talking to a few guys who Stephanie and Johnny the bartender said were safe to talk to. I enjoyed the girls the most - even though a couple of them flatteringly came on to me! I was not in any way interested in sex. I felt strongly that I was a heterosexual crossdresser making me rather unusual for a very uncommon place!

One guy named Jack always came over to talk to me. He was older and smooth talking. He kindly bought me drinks, often all night long! Girls do love having drinks bought for them! On a subsequent Friday night - after much begging on his part, Jack convinced me to dance with him. I must admit fast dancing in a tight, body hugging, teensy skin revealing spaghetti strapped mini dress was perhaps too daring – But I did, however, feel very erotic and even hot in doing so!

Later that evening I even played pool with Jack. I so was beginning to feel like one of the girls here now. I’d seen some very sexy asses leaned over the edges of this pool table and now I was doing so. I think on one shot when I leaned over the table - my panties may have shown a bit. I did hear a leering whistle. I did enjoy interacting in a manner that a woman would. Unfortunately, I was far more of an unintentional and naughty seductress than I was even aware of.

Ironically in spite of my friend Stephanie’s hints, I didn’t fully understand what my appearance clearly said to the men in the bar! My new friend Jack did tell me that I was hot! He told me my ass was incredibly sexy and that I was the most beautiful girl in the bar. I took it all in as the usual flirting male flattery. I did enjoy hearing his compliments and his apparent adoration of me brought me what I would call a comforting satisfaction.

Jack met me the next night at the bar and once again generously bought me drink after drink. He easily persuaded me to dance again. I was now finding myself comfortable enough to enjoy a man’s company for the first time in my life. I rationalized that being a girl and having male company was rather normal in the world and especially in a bar like this.

Jack was also quite safe in my mind. Stephanie and Johnny both agreed. Each had told me that he was a good guy. Jack was twice my size, twice my age, and was also married. Jack was old enough to be my father and was the perfect person for a gal like me, to hang out, talk, dance and sip a few drinks with!

Late, just before closing, I was feeling tipsy and even quite happy with myself. Jack was his witty, funny and his quite likable self. Once again he asked me to dance and this time I whole-heartedly agreed. We began dancing when suddenly there was a change in the music. I had never heard a slow love song like this playing at this wild and crazy night club.

In seconds I was being drawn up against Jack by his powerful hands, in a slow and intimate dance! Before I knew it I was being held closely and gently cuddled by this man. In the past I would have immediately pushed any guy away. - I once even slapped a grossly inappropriate guy in the face! - Now though, I was neither repulsed nor being reactionary. He was married and this was as innocent as innocent could be!

I felt his warmth against me and I felt a sense of mysterious calmness. To my great surprise, I was comfortable and relaxed in his gentle embrace. Jack’s strong hand was on the lower arch of my back and I was aware that his touch, combined with the thin stretch fabric at my waist almost made me feel naked. His other hand was firmly holding me at the bottom of my derriere and gently touching my stocking beneath my teensy short dress.

The comfort I suddenly felt while being held while dancing was something I found more than confusing! Suddenly my heart and body felt so many conflicting sensations at once. I felt exposed, yet strangely stimulated. I felt appreciated and sensed a likeable and gentle warmth coming from my dance partner.

Jack is quite tall and quite fit. He’s one of those workout guys who runs and stays in good shape. I must admit he is a petty handsome guy. The little bit of grey in his hair on the sides makes him look refined. He looks like a guy who could make his wife proud. Being so much smaller made me feel tiny in his arms on top of the very new experience of being held by a man. This seemed rather awkward for me, especially at first!

Jack’s other hand then gently slid up to my lower bottom as we swayed in unison to this unique slow wedding reception like song. His touch was magical and I found it pleasing, even strangely erotic. I settled into his grasp in both comfort and a sense of astonishment that had my mind reeling in both confusion and yet also some kind of inexplicable delight.

After about a minute more of dancing, I realized that I was getting physically stimulated by his touch. I could even feel the hardness inside his pants against my flat stomach! Was this something natural or was it twisted and bizarre? Part of me wanted to run, but most of me wanted to stay right where I was.

I was finding that Jack’s touch was comforting yet as he pulled me closer it was becoming rather suggestive. There was a strangely sensual intensity to our coupling. Jack was gently drawing me to him and I was strangely not objecting. I held Jack close, enjoying the tenderness, yet again I was mystified by these new, conflicting and even sensual emotions that my body, heart and brain were experiencing.

It was so bizarre that I was being held by a man. In his arms I actually felt like I was a real woman. My feminine aura and heart found his affection and even his sincerity to be quite real. This all almost made some sense to me. I also felt his hardness once again as he pulled me more firmly against him. He was aroused and I somehow realized that though only briefly, I may have been responsible for his state!

When the music stopped I was suddenly surprised and even embarrassed by what I had felt. The lights abruptly went on as it was now closing time. I panicked, feeling both shameful of myself and even mortified by what I had allowed to happen. I had been sensually stimulated and moved by his touch and our closeness. I awkwardly fled his grasp in order to get my cover-up jacket behind the bar.

Jack soon followed and being the gentleman he always had been towards me, offered to walk me to my car. I wanted to say no but this had been our developing routine during a time when things could get a little unsafe and unruly outside the bar. He took my hand and led me out. I suddenly felt exposed yet his shielding and kind protection of me settled me for our walk.

“I’d love to take you out to dinner sometime soon Cari.” He said smoothly as we walked holding hands. It was not the first time he had asked. “Please, there will be no strings attached.” He said kindly. I was still in a confused sense of panic due to the sensations and emotions I had just experienced. I wanted to run and / or flee, but Jack had a kindness and protectiveness that kept me centered and on my feet.

My mind was spinning when we reached my car. Jack drew me close putting his hands around my waist. He looked into my eyes. When his lips came close, new baffling and inexplicable instincts drew my lips to his. The warmth of his kiss was dizzying. I found myself on my tiptoes in my high heels extending upward to meet his kiss. As perplexing as my reaction was, I was stunned, infatuated and electrified by his lips. I passively allowed his gently searching tongue into my mouth. He was warming my heart and my now completely confused feminine soul!

Jack stopped to look me in the eyes again. I was breathless, captivated and even smitten. He teased me by bringing himself closer. Curious and without thought, it was I who was drawn inexplicably to him for another kiss. Once again I found myself standing on my tiptoes to meet the lips of this tall and handsome man. I was taken and even captivated by the powerful, even mind-blowing enchantment of the moment. None of these emotions or feelings were ever on my personal radar!

My surging, unexplainable passions had me feeling like a love-struck teen. In my naïve innocence, I decided right then that I would dare to go to dinner with him. I wanted to learn more about being a woman. I suddenly wondered what it would like to be dating and perhaps even again kissing a man! I then got quite an enthusiastic hug and Jack suggested a plan for next weekend.

Jack said that he would pick me up at my apartment next Friday night. He wanted to take me to a special place and he would make reservations for the two of us. I was enchanted, confused but quite surprisingly willing. For the first time in my life I gave a man my cell phone number. I had never ever processed that I would ever do that! Jack then promised to call me on Wednesday night to get directions and my address from me.

I got into my car with my head spinning. My mind and soul seemed taken and fixated on the evening’s events as I drove back to my apartment. I was happy, thrilled and yet totally baffled by what had just happened. I was stunned that I had just given my personal phone number to a man. Even more mystifying was that I had agreed to a dinner date with a man.

My focus on the road was poor as my mind flashed back to what had just occurred. I had just been kissed by a man. Even worse, I had responded quite passionately to this man. What in the world was going on? I was suddenly nervous and anxious. Puzzled and perplexed, I fixated on wondering what had I just done. What seemed to be wrong with me?

When I got home I just crashed into bed. I slept in a sexy sheer nighty, while remaining in my make-up and feminine state. My dreams were consumed with erotic, mysterious tones. Even in my sleep, I was preoccupied with the fascination with the new passions I was fabricating and experiencing in my heart and soul. There were so many things I seemed confused about and behaviors that I had experimented with in the past suddenly came into my mind.

It was one in the morning but I could not sleep. Like a typical teen, I had true fascination with sexual things. I had sex with my senior year with my pretty cheerleader prom date as a male and so loved having her please me in both oral and more carnal ways. Interestingly I wondered why in the past I had purchased a vibrator, and two different sized dildos. I had admittedly played with them in my anus while dressed as my feminine self.

I never believed these things had any connection to anything more than simply being a powerful way to masturbate! Friday was just going to be a dinner date I mused. Having sex with a man as a woman was for the girls at the club and certainly not for me. I still believed that I was one hundred percent heterosexual. I never felt there was any connection to these past behaviors.

Monday at school I was back to my male self but my brain seemed riveted and immersed in the mesmerizing feline and even erotic sensations that I had experienced two days earlier. My thoughts raced and I couldn’t erase the reality that I had felt his hardness pressing against me while we were dancing. I think then I realized that Jack was no different from all those men in the bar. Asking a girl out meant that he definitely wanted to have sex with me!

Now Psychology class seemed far more relevant. I had always felt that I would never have sex with a man. Was I now in the process of rationalizing or was I repressing real urges or desires? Was I gay or was I destined to be something more than a simple heterosexual crossdresser? I just couldn’t go there. It was beyond what I could currently understand and comprehend.

I would have to be both smart and cautious on our no strings attached date! I now realized why Jack wanted to go out with me. Being married didn’t stop far too many men from wanting more! I now remembered his even mentioning something about being separated from his wife. How could I be a man’s girl friend?

As Wednesday approached I began to nervously look forward to Jack’s call. I did enjoy the interest Jack showed in me and the constant flattery that he brought on me. There was a strange comfort and anticipation in knowing that I’d been asked out on a simple date. For the first time, I would be getting myself dressed up for a date and I’d be dressing for Jack. It was exciting beyond words but to say I was nervous, guarded and cautious - would be the understatement of my young lifetime!

Wednesday eve the phone rang to the very minute that he promised. I felt like I knew he most definitely would call. Little things mean a lot in the development of trust. Hearing his smooth, friendly encouraging voice had my full attention. Jack heartened me by telling me how much he was looking forward to Friday’s dinner. He told me we had seven o’clock reservations. The restaurant he was taking me to was an elegant one in the Park Square area. After dinner, we could go to the club which was nearby where we could go for drinks.

His words calmed me and I felt assured that I was not in a position that would be awkward or where I might feel pressured. I shared my many fears with him including my worries about having a not completely feminine voice in a regular public setting. Jack said if I was that uncomfortable he could order for me. His protectiveness, kindness and insights gave me great confidence in him. He seemed to understand where I was coming from almost all the time!

He also told me how much he enjoyed our kisses and how moved he was by me. I had to be honest and blushing like a schoolgirl, had to admit I felt similarly. Here I was mysteriously admitting that there was possibly something between us. I was unintentionally confessing that it was possible that there might possibly be more than just friendship between us!

I almost felt a sense of romance in my heart. My honesty just seemed to slip out due to his sweet words and way. We spent over an hour talking. All the while I felt like an enthusiastic teenage girl with my nice handsome boyfriend on the other end of the phone! By the time we wished each other a good night, everything seemed right in the world – at least to me. My fears about our date were allayed by him and I was definitely feeling a strong comfort and even like for him!

Friday morning, I was so focused on the upcoming evening that I almost decided to skip all my classes. I did go reluctantly, but left early before my last class to give myself plenty of get ready time. I was so excited about what was about to be my very first date. I never got up dressed for a man before! I always dressed to please myself but tonight was definitely so very different.

I so love the transformation process in becoming Cari. Everything from my long bubble bath to shaving myself all over this time seemed exceedingly special and even rather quite erotic. Once I dried off, I added my long red fingernails and painted my toenails brightly to match them. My entire body looked perfectly all girl except for my seven and a half inches of masculinity that seemed by all of this to be stimulated and eternally hard!

I had purchased new blonde hair extensions at the shop that made my hair look all my own and mesmerizingly princess like. Adding eyelashes, dark eye shadows and drawing in my perfectly lined bright red lipstick - stunned even myself in the reflection in the mirror. I slid on a favorite frilly, sexy black mini dress and five-inch heels and I was truly in love.

When I get my look right I am completely amazed. Now my reflection just seemed so perfect. My look was so complete. I knew in my heart that I could do more than just pass a girl. I was convincingly pretty and almost model like in my mind. As long as I could keep my hardness under control in my panties, I was the perfect, hot and more than just plain attractive young girl! I looked a bit like a human Barbie doll in my lust-filled brain!

Jack was picking me up at six. I was all ready and it was two hours early! Still, I was frazzled with excitement. Something in me was changing. Why was I so excited to be going out on a date with a man? This morning I was all guy. This afternoon, I was all beautiful girl! But mysteriously, it seemed more had changed.

I wanted for him to be so pleased to see me. I wanted to be so special and so pretty and attractive for him! I wanted to be a man’s stunningly alluring girl! My make-up, dress, high heels, and perfume were all for being so perfect for him!

With two hours to spare, I decided to try on many of my different dresses and outfits. I tried on a favorite sexy little red dress. Then a dark blue tube type dress. I tried on a half dozen other dresses. I also tried on a favorite red bedroom camisole. It had red string ties at the waist and garters attached. In matching five-inch high heeled platform pumps, I was the essence of a centerfold like a pin-up girl in my sexual attractiveness.

I looked like a European Playboy Magazine model in the mirror. A bit exotic, yet still with that all-American cheerleader look. I was mesmerized. I was in love with that beautiful girl in the mirror.

Suddenly the doorbell rang. Startled and quite surprised, I looked at the clock. It was exactly six o’clock. I’d been so mesmerized by the sensual, hauntingly sexy woman reflected before me, that I had lost track of the time. I buzzed the door, allowing Jack to come up to the third-floor level and to my door. What would I do? I wasn’t ready and I needed to buy some time!

I heard his steps coming up the stairs and he was soon knocking on the door. “Hold On” Jack. “I’ll be right with you…” I said in a high pitched panicky voice through the crack in the slightly open door. I could see him holding roses. Impulsively I couldn’t let him wait in the corridor with my neighbor’s door nearby. Impulsively I decided to let him in. In a moment for the ages I truly had to wonder just what I had just done!

End Part One