For as long as my memory serves me, I’ve had a powerful desire to look and feel feminine. Despite being all boy, my challenge in exploring and fulfilling my desires would be quite a test in an often-intolerant world. My reality was that I had to choose to pursue these strong, mysterious desires in secret. I knew I had to balance familial and societal realities. I knew that friends and family would find my fetish like desires too different. It was my needs and natural want to experience my feminine side, that drove my exploration onward.
I was incredibly opportunistic and clever in acquiring a stash of make-up and feminine clothing by the time I was a freshman in high school. By my junior year, I had already courageously explored the world in public dressed like a girl. I believed - in my heart - that I passed as a female while taking a walk in a Boston neighborhood, when I had an opportunity to apartment sit.
By age seventeen, I was off to college and thrilled to have the opportunity to find a small one-bedroom apartment. For the first time I could be discreet. I could finally explore opportunities to become the girl of my feminine dreams. To accomplish this, I needed to be both ingenious and earn enough money to become the weekend female I so desired to be.
I took the perfect part time job. I had often visited a Boston wig, dress and accessories shop. I heard they had an opening, and I was hired because I had already learned about almost every item the store sold. I naturally knew about make-up and believably feminine hair.
The shop catered to women but almost equally to transvestites and crossdressers. I would make many a friend while working there. I could also try on wigs and high heels there - so my purchases were worthwhile and of the best quality for myself.
I had already acquired a significant collection of feminine things in the past two years while at home. Now in my apartment, for the first time I chose to shave every inch of my slim body completely smooth. After a full week of practicing make-up, dressing and walking around in heels I was buoyant. Before my college classes began, I felt that the mirror told me that I might be ready. My reflection had me thrilled beyond belief. I was excited and very willing to try some very daring exploration.
I so loved the intensely feminine feeling of my smooth-shaven, soft, perfumed, quite lithe body. My light brown, blonde streaked, auburn hair was shoulder length and feline. At only five foot five inches of height and merely a hundred and twenty-six pounds, I looked great in almost any dress. Being short made me even more believable while wearing high heels that were anywhere from four to six inches in height.
Using my recently bought blonde hair extensions and in my realistically feminine make-up and my girlish clothes, I believed that I could pass as a gal in public. Though I was scared and fearful, I was determined. The strong desire to be Cari in public kept me from staying back in my apartment. Now having some confidence, every Friday and Saturday Night, I would go out in public, dressed to the nines. I’d daringly go out to a transgender bar in downtown Boston.
Going out dressed as a girl to a bar was incredibly terrifying and intimidating at first. The sight of me - a uniquely pretty, young, sexy, believably feminine gurl in teensy dresses and alluring high heels, was a rather eye-catching spectacle to most. I don’t understand why I was never carded, but I must have looked older than seventeen to the door men. When I’d sit cross legged in a mini dress at the bar, I was literally like flypaper. Most of the men were unfortunately brutally forward and even often relentless, in my pursuit. Frankly, I was scared to death at times and the bartender who I would generously tip became my protector. As a result, I usually retreated to the company of the girls who were like me at the other end of the bar.
It wasn’t long before my sexy, sensual short dresses and elegantly feminine looks soon had me labeled as the ultimate tease in the club. Despite my no touch and tease only reputation, I was constantly chased, ogled, and pursued by dozens of sleazy, forwardly shameless, and seemingly thoughtless men.
The first few weeks out in public as Cari was a trial of tolerance. It was so difficult learning how to deal with every kind of human being. I didn’t know the real why behind my dressing as a girl, but I knew how much I loved how much being a girl made me feel. I felt sexy, and even aroused by my own appearance at times. I didn’t dress for anyone but for my own pleasure and my own personal delight.
As much as I did actually feel flattered by the attention that I got from men, I related better to the friendliness and understanding of the girls. Some of the gals even hit on me with seriousness and humor, but I found their ways far less threatening. The girls thought I looked incredible, and I was thrilled to get so much positive feedback about how convincing I looked like a gal!
Still, I loved being called pretty and even beautiful. I was often offered drinks by men. I was beginning to believe that I was very attractive. Being constantly told that I was sexually desirable, and alluring made me feel both deliciously feminine and delightfully sensual at the same time. If only those pestering guys would relent. I simply wanted to enjoy being the flirty, teasing girl that I so loved to be!
One Friday night, I was approached by an older, handsome and well-spoken man. He was funny and warm. He was - for a change - a guy who didn’t turn me off. He made me laugh with his sharp wit and quick, sarcastic sense of humor. My girl-friend Stephanie had previously shared that he was very fond of me, so I was careful to keep my distance.
He kindly bought me many drinks over the next few weeks. His doting nature and his generosity was gradually earning my trust. I began to feel a sense of friendship and confidence in him. He would meet me at the bar every Friday and Saturday night. When I would arrive, he’d always have a drink and a saved seat ready at the bar for me.
It was very new to me to be able to talk casually, and even speak jokingly with a man in this dangerous, wildly awkward environment. Jack was unique, patient and seemed very different from the other men I’d met. He would even thoughtfully walk me to my car each night after the bar closed.
Jack would hold my hand to make me feel safe when we were walking by people on the sidewalk or street. That made me feel feminine, safe, cared for and protected. I realized that his company made me feel so much more comfortable in the crazy Star Wars like bar I visited each weekend.
To me up until now, the simple feel of feminine things and being a gurl was more than enough of a reward for me. Now I had a male friend and my girlfriends at the bar were buzzing about it. I think they thought we were more than just friends because we seemed so compatible and cozy at times.
I had no sexual intentions, nor any willingness to seek more from Jack. He had asked me out to dinner several times, and my friends Robyn, Stephanie, and the Bartender Johnny, thought I was crazy to be so resistant. I resisted strongly, believing that I wasn’t gay or even bisexual. I was attracted to women, though.
The next Friday night, we had a great time talking together. We played pool and I lost to Jack a lot more than I won. Jack plied me with many a drink while we played as he usually did. I loved listening to his jokes and his observations of the very unique patrons at this alternative bar.
I innocently and naively enjoyed Jack’s company. I had accepted him as a friend and protector. That night, feeling brave and tipsy, I even said yes to dancing together a few times. Near closing time, he shocked and surprised me by taking me by the hand for a slow dance.
In all my times at the bar, I never even heard a slow love song playing, less been asked to dance during one. I soon found myself being held closely against him in my teensy mini skirt, silk stockings, and five-inch-high heel pumps. There was something surprisingly comforting but very different happening during our dance.
Jack was well over six feet tall. I felt very tiny and indescribably vulnerable in his arms. I was astonished by the pleasurable feelings from his closeness and touch. There seemed to be a unique warmth in being held against a man while dressed completely as a woman. Feeling his hands on me, separated only by thin silky material, made me shiver!
This had me swooning in confusion, yet I was gradually melting into his arms. As one strong hand grasped my waist tightly, the other hand gently found my bottom. I was breathlessly moved by the intimacy I felt from him. He gently drew me even closer, as I was stunned and shocked by the affection I was feeling.
I suddenly felt erotic flashes from his alluring touch and gentle caresses! I was honestly enjoying being a girl in a man’s arms on the dancefloor. As the music stopped, he kissed me deeply on the lips. I was reeling, stunned, and at the same time mesmerized. The dramatic delight of this intimacy and his tender embrace had me melting yet terrified.
For the first time as a gal, I felt stimulated by the presence and touch of another person. As his kiss became more intimate, I felt his tongue swirling gently into my mouth. I unconsciously reacted naturally by responding in kind. I was being French kissed by a man, and I did not push him away.
I was experiencing emotions and sensations that were astonishingly pleasurable. I must admit that I was staggered by my response. I could not fathom my unexpectedly willing reaction to him. Seconds later when I realized what I had just succumbed to, I scrambled away from him, just as the lights went on -signaling closing time.
Jack found me collecting my coat from the bartender. I was embarrassed and confused. I wanted to run or flee. More than anything, I was very aware that my own male-hood was hard as a rock. Our dance and a bit more had made me stimulated beyond belief! It is hard to walk in a dress and heels when one’s gurl cock is so hard and trying to escape a girl’s panties!
I had never reacted to a man in this way. I was dismayed and very much mystified. Jack could tell that something was not right by the horrified look on my face. He may not have known, but I was completely dumbfounded. I was more than embarrassed by my response and my extremely unexpected physical and emotional reaction to him!
I was moved by all of this, yet my responses had not make any sense in my heart or brain. I relented and allowed Jack - who I had accepted as my protector - to take my hand. He walked me to my car. All during our walk, he was tactfully trying to convince me to go to dinner with him the following week. I was still hard and walked awkwardly in my teensy dress and very high heels. I couldn’t wrap my head around such an idea.
I had never seriously considered going on a date with a man. I was obviously just a pretty, elaborately made up, boy in a sexy dress, makeup, and heels. Tonight had been crazy. I had been kissed by a man. I had felt something far greater than I could have ever imagined. Jack’s persistence in asking me out was overwhelming me.
Jack looked me in the eyes and asked if he could call me on Monday night. In the hope of saying good night with the opportunity to escape, I demurred by saying yes. We had never talked on the phone though I had given him my number if he promised not to call me during the week. I was not comfortable enough with my persona to take a call from a man while dressed as a guy.
Jack then boldly asked me if he could kiss me good night. I felt like I was being pushed but I submissively surrendered by saying yes. I felt so feminine when his tender kiss took me to a place I had never dared even consider. Suddenly I had become a very vulnerable, responsive girl. I was so mesmerized and so moved by the simplicity of his sensual lips on my own red lips, that I was breathless. I was unconsciously allowing him to stimulate and arouse me!
I did not push him away as our tongues once again met. Intense, feline lustful emotions filled my heart and soul. I had no understanding as to why I was reacting like this with a man. I felt passionate surges that were dizzying and intense as his hand drew my bottom against him. I instinctively drew myself closer to him.
Now closely against his pelvis, I felt something huge and hard between us. He was moved like I was and yet, at least momentarily, I was not afraid. The girls at the bar thought he was sexy. I did find him warm and doting, but his kiss was making me crazy. This did not make any sense to me.
My bottom was round and feminine and the feel of this man’s hands on my teensy body-hugging mini dress dizzied me beyond words. His hands and fingers gently caressed my body causing stirring new, erotic feelings that I could not comprehend. Each touch made me yearn for the why in what I was experiencing. His lips, tongue and hold had me helplessly absorbed in an almost forbidden passion. For the first time in my life, I truly felt completely like a woman. I was being held and excited in an intimate and yet captivating embrace, far beyond what I had ever comprehended!
I realized that I was standing on my toes against him in my high heels. I felt amazingly feminine and yet now dizzied beyond words. My soul was aroused and moved by this completely unexpected emotion. I felt simply like a real woman in the arms of a handsome and loving guy. Was this why I was a smooth shaven, perfumed pretty boy-girl?
Once again, I found myself flummoxed and thrown completely out of my element and experience. I pushed back from our locked lips gently. I was both stunned and confused. My flight instinct caused me to finally blurt out a response. “Call me Monday.” I said half breathlessly. I was still quite floored by my actions and willing reactions.
My confusion and need to regroup was in high gear! I needed to escape and to get back to my apartment safely. My mind was spinning from tonight’s events. As I drove home, I was both dazed yet amazed. I drove carefully having drank more alcohol than I should have. I need to regroup and think.
I got home stripped off my dress and heels. I put on a sexy black negligee. I went to bed feeling more like a woman and a female than I had ever felt in my young life. I couldn’t sleep. My mind raced recalling my feelings in his arms and embrace. I couldn’t keep my hands off my smooth, lithe body. His kisses had filled my mind with both wonder and fear. What was I? Was I gay? Was I bisexual? Was I just a girl when in a man’s arms? I was unnerved yet obsessed with tonight’s mind-blowing events.
My hand rubbed my ever-so-stimulated seven-inch cock. In my sheer black negligee, I was smitten about the wonder of being a girl and the eroticism of having being kissed by a man. Feeling haunted and yet sensual beyond my dreams, I shuddered into a powerful orgasm. The idea of being held AND kissed by a man, was perhaps something I had better come to understand sooner, rather than later!
Monday during my Psychology class, I was in a haze. I was still lost in the memory of Saturday night. Knowing that Jack would be calling tonight, was also weighing heavily on my mind. Had I been naïve about myself for all this time as a transvestite? Did I dress and look like an attractive gal for the purpose of attracting men?
Ironically, Psychology class was about the concept of denial, which suddenly had great meaning. Had I been repressing and purposefully rejecting my emotions and feelings? Was I just a whore in waiting as my friend Stephanie would joke? Did all girls like me eventually succumb to a man sexually? Deep down inside, I doubted it—denial—but I knew that I really wasn’t sure at all.
I went home early from class, unable to stay focused. I bathed, shaving my body elegantly smooth, in a luxuriously soapy bubble bath. Just thinking about what it must have looked like to see me standing on my tippy toes with Jack's hands on my waist and bum embracing me in a deep kiss. That must have been an incredulous sight! I was finding my maleness to be responding and expanding as I recalled the scene.
I envisioned myself in my teensy little minidress and stockings, made up to the nines and in a man’s arms. I unexpectedly had outlandish thoughts running wildly through my mind. Did I want more from Jack? Was my behavior simply girlish? Was I ready to dare to find out?
Suddenly I realized how naïve I had really been. Jack most certainly wanted more from me. I had clearly felt his hardness against me when we embraced. I realized that Jack had been pursuing me not just from day one – but for months.
Now it was becoming clearer that my answer tonight to Jack about dinner would be perhaps the most important decision of my young life as Cari! Half asleep in the joy of the warm bath I closed my eyes. My friend Stephany’s words kept coming back to haunt me. She used to joke that I was wasting time just going out to the bars.
“You are the most fuckable girl in the bar, girl,” she would often say! “You need a man to make you a woman - she would joke! Her words now seemed wise and even perceptive. But was I that kind of girl? Denial, according to my Psychology professor, was a very powerful force! My mind kept thinking about the crazy feelings that I felt while in Jack’s arms Saturday night. His warmth and attentions made me feel very feminine indeed. It just felt so good. I was struck by the moment. At the time it had felt even wondrously natural.
I felt I was watching the late-night scene where I was standing on my toes in my high heels while he held my narrow waist and curvy bottom in our embrace. I felt feminine and female beyond words. My soul was touched by feeling like a real woman in the arms of a handsome and loving guy. Was this why I was a smooth shaven, perfumed pretty boy-girl?