Learning to be a Girl

Learning to be a Girl

A Young Sexy Transvestite Learns About Life

By Cari Christi

Is there anything sexier than walking into a bar and seeing a petite, slim, sexy, young 18 year old blonde girl in a teensy black tight fitting dress, sensual high heels and an all American smile alluringly standing by the bar? I’d recently been “pursued” by a man named John for a number of weeks and that was his description and reaction to seeing me for the first time. I had been “that sexy young girl” out in night clubs for over a year. So often the “scene” was more about dodging lecherous men, pushing away eager young suitors, and avoiding the self-centered people that made the night life in certain Boston city clubs seem far scarier than even a Star Wars kind of bar.

What makes my persona rather different than most is the fact that I am told that I’m rather quite attractive and feminine in appearance. My reality while out in public places in my sexy tight little dresses is that I’m really a smooth shaven guy in a dress! My skillful make-up, use of elegant wigs, and my attention to all of the “details” makes me very passable in public, even in the transgender bars that I liked to frequent.

My somewhat elaborate and advanced appearance came as a result of hard work, “mysterious” desires and acquired skill. I’d been dressing like a girl since my early teens in secret and now that I had my first apartment prior to going to college I finally was able to let the girl inside me - be outside in the real world every weekend! I loved the excitement of the transgender, straight and even gay bar scene. I loved simply being dressed as a woman. I also enjoyed the energy of the clubs and had been lucky enough to make a few friends as well.

Being a rather short (5’5”) tall and a slim 130 pounds made dresses look almost completely natural on my smooth soft skinned body. Adding five inch high heels and in pretty long blonde hair extensions made for a rather sexy and believably female sight. Many evenings I would wear tight fitting waist cinchers and even corsets to bed to train my waist to quite small proportion. I was dedicated to the full “look” and paid attention to every detail I ever was able to learn about.

Given that I so enjoyed the lust of being super feminine, the tight fitting short dresses, nylon hose, teensy panties and long red fingernails became the norm for me. Even my long eyelashes were sometimes a spectacular but believable add on. I loved bright red lipstick matched to my bright red painted toe nails. I was as they say – a gal who was always dressed to the feminine extreme.

I was a bit of a man magnet – but up until now I had one hundred percent reverse polarization! I always pushed men away out of both habit and frustration. I believed strongly that I was a heterosexual crossdresser who just was crazed for female clothes and that extreme fem look I so loved. I found it both emotionally and even at times sexually satisfying as in a true type of sexual fetish. I did not expect things to ever change, but my feelings began to waver when John rather cleverly found some vulnerabilities in me that I never knew that I had.

On Friday and Saturday nights, I’d go out to my favorite club and meet my new friend John. He had been buying me drinks on a regular basis for virtually the entire winter. He was the first guy to ever get me to dance and I at least enjoyed the universal “concept” of girl dancing with guy. Dancing to me was both innocent and fun. All of the melodies played at the transgender club I frequented were lively, modern and loud. On the last Saturday night in April, I was with John on the dance floor enjoying some high energy dancing when suddenly the music changed. Apparently the DJ chose to play a very the atypically slow love song, the kind of which I had never heard in this night club before.

Surprised by the tenor of the song and before I could walk away, I found myself being held closely by John. At first I was startled, but it a strange way it seemed normal. I was dancing with this guy and being held close was not objectionable. Guys held girls when they danced and much to my surprise I found that close dancing was even pleasant. In an odd way I actually liked being snuggled and held tenderly by this much older and much taller man. As I found myself a bit more comfortable, I felt a strange sensation when John’s hands slowly and subtly slid lower to my derriere. I didn’t find myself in my usual panic. Normally a guy would have known clearly my feelings on that! One guy in the past had found my hand stinging him across their face for a similar thing!

The unusual sensation of feeling his hand on the edge of my short dress and stockings had a powerful yet delightful effect. Never would I have guessed I would feel stimulated by the apparent eroticism of being touched as a woman by the hand and fingers of a man. Having my thin, tight dress and silken stockings being gently caressed in such a tender manner had a magical electricity that caused my eyes to open wide. I suddenly realized that during this first slow dance of my feminine life, I felt incredibly female and yet I also felt so very vulnerable and perhaps even exposed. I felt so feminine in this man’s arms and without any conscious thought I instinctively held him closer.

John smiled, looked me in the eye and winked at me. I smiled back but suddenly I was getting kissed on the mouth! I was stunned yet his lips were so tender and felt so warm. I didn’t try to push him away. I being lit up in a strange sense of lust and feline emotion that I had never felt nor even considered to be possible in the past. When the song ended I was both blushing, flustered and a bit embarrassed. The edges of John’s lips had been reddened by my bright red lipstick. What had just happened was never on my personal radar. I had just reacted to a man like a woman would and I found myself in a panic, feeling naked, even ashamed and anxiously wanting and needing to flee.

The lights suddenly went on. That last dance signaled closing time. I rushed to the bar to find my coat as John tried to keep up. I was, disconcerted, mortified and even humiliated at my own actions and unexpected response to John’s affections. I fled to the door and John caught up to me on the street. He was kind and concerned. “Are you all right Cari?” He asked. “Yes”, I responded somewhat falsely. He insisted on walking me to my car where I thanked him and gave him my usual promise to “bump into him” at the club the following week.

For the drive home and for much of the rest of the week I tried at times to digest and make some sense of what just what had happened with John. I was actually quite distressed and troubled by how I had reacted to John’s touch. I was petrified that I may have sexual tendencies towards men when dressed as a woman - which I had always rejected and perhaps had repressed deeply over time. Still my denial couldn’t reject the reality of just how exciting and how enchanting and dream like that his touch and kiss had been.

At the bar the next Friday night, John pulled me aside to talk in private. He apologized to me for kissing me so unexpectedly. I accepted his apology and I nervously joked that I had gotten over it. A couple of free drinks later, I admitted to John that his kiss wasn’t all that bad. In fact after more drinks I admitted that I actually enjoyed it. John was thrilled in his quiet yet subtle way. He spilled to me that he had paid the DJ for the “slow” song played during our last dance! I laughed and commended his devilishness. I knew that he liked me a lot and I must admit his flattery and honesty made me feel more and more comfortable with him.

A few drinks later I was being asked out on a date by him. I had been asked out dozens of times by dozens of men in the last year and never once said yes. John convinced me that dinner would have no strings attached. He said he loved being with me and that dinner and drinks would be just for fun. In all the time I had been “out” in public, this time I felt positive about such a possibility. I managed a weak, almost embarrassing yes. John was thrilled and gave me a big, sincere genuine hug. He would pick me up at my apartment the next night at 7:00 P.M.

Saturday morning arrived and I awoke in a bit of a state of frenzy. I had all kinds of strange dreams and in one – I was being kissed by a man (It wasn’t John) and after the kiss I panicked and in fear – I decided to run. In the dream I ran and ran. I was scared but I was overtaken by my pursuer and I got caught. The man grabbed me, took hold of me and I got kissed again. Once “caught” I didn’t run. I just enjoyed the kiss and woke up with a painfully hard, stimulated erection! I couldn’t deny there was some sort of sexual connection in the dream and where I was at emotionally, yet I had never pondered to any great degree what all of this might mean. My reaction to that evening’s fateful kiss was mysterious and yet for whatever reason(s), strangely exciting.

Whether it was the dream or the thoughts of his kiss, I was more enthusiastic about my feminine side than ever but also more confused than ever. Even more crazy was that as a sixteen year old “boy” I had dated a couple of very pretty gals in high school. I remembered how excited I was about my first Prom date - but this seemed quite odd and extremely different. I had even been lucky enough to make it all the way home with my girl-friend quite a few times. Sex with her was awesome and unforgettable – yet here I was about to be going on a date as a boy-girl and sex was certainly out of the question. I was still in my mind a heterosexual guy who just loved “being a girl.”

What I did (at least) know was that I was going to go all out to look sexy and perfect for John on my first date as Cari. Much of my craving and desire to be appealing in appearance is due to my own perfectionism and my own personal vanity as a gal. I spent the day relaxing in a luxurious bubble bath, shaving my entire body perfectly silky and smooth. I even shaved my pubic area so I was a 100 percent shaven “female” except for seven inches of rather obvious maleness that so often during the day - was quite moved by the silky smooth feel of my own burgeoning and so real feeling femininity.

I began my feminine preparation by adding long feminine eye lashes. My blonde hair extensions blended beautifully with my sexy blonde bangs and my sensual eye shadow. I pierced my ears which I do periodically and added long sexy gold leaf earrings. Even my eye lashes were lightened with bleach white to match my blonde hair. I knew all of the tricks from my perfectly glued bright red nail extensions to my favorite matching shade of bright red lipstick. I often am stunned when I look at myself in the mirror and even when naked the rather largish 7 inch erect cock on the girl in the mirror seemed very out of place!

I tried on my favorite black dress. With a deep V neckline and thin spaghetti straps, exposing all of the skin above my breasts, I looked so sexy. The dress was so short and tight fitting that I had chills. My flat stomach and tiny waist was the body of a young slim girl. I added matching black 5” high heeled stiletto pumps and when I looked in the mirror I could not believe the stunningly feminine creature was me. What a creation! She was young, trim, stunning and even beautiful. I almost could not believe the reflection in the mirror was me.

Still two hours away, I was ultra-content with my good looks. I felt confident I would pass well at the restaurant with John at my side. I decided to try other dresses and outfits. At but seventeen I was already the owner of over 20 dresses, six wigs, all kinds of lingerie and more. I tried on a white dress that I’d worn out several times that drew many compliments. Frilly, short and ultra-feminine this dress would be perfect. With plenty of time I tried two of my red dresses on. Then my long black cocktail dress that made me look like a movie star. I tried on a pink negligee and a then an alluring frilly, sheer, black nighty that I sometime wear in private to bed. That mirror kept fooling me! I just could not believe that my reflection was not ALL female!

Suddenly the door-bell rang. I had been lost in the mirror’s lust and lost track of time. I live on the third floor of a three level brick front home and in but 5” black stilettos, French perfume and the tiny sheer black negligee I had just tried on I was not quite ready! I buzzed John in at the street level and decided I would ask him for a couple of minutes when he reached the door.

I opened the door peering from an angle to ask for some time not revealing my state of undress. John stood stunningly handsome in a dark suit and with flowers in hand as I explained while melted at is wonderful appearance. “I’m not quite ready, but come on in” I said – aware and genuinely embarrassed by my overtly exposed state and balking with a sincere apology. I smelled the scent of the beautiful roses and demurred while he smiled and looked me up and down.

I stood momentarily before him suddenly realizing the complete vulnerability of my circumstance. Had it been on purpose that I lost track of time or was this some kind of subliminal hope or desire on my part? It didn’t matter because his lips were soon on mine and the beautiful bouquet of roses was tossed by John onto the couch.

I felt like a little girl in his powerful arms as his hands went to my exposed derriere. I had this rush of need and lust without any conscious mental preparation I did just what any good girl in lust would do. I wanted to feel him against me. I wanted to be his girl. I helped him remove his shirt while I instinctually and submissively slipped to my knees!

I never even wondered or dared even think about what I was about to do. It seemed so natural and so right. I fumbled with his belt buckle and the fly on his pants. With his pants at his ankles I pulled down his shorts. Inches from my face was the biggest, hardest, most intimidating cock that I had ever seen. John was over nine inches long and had a huge thick mushroom shaped cock head. I was going to taste that monster regardless if I knew how to or not.

I began with my tongue as my girlfriend had done, but the rest would be pure instinct. Opening as wide as I could, I tasted the head of his magnificent manhood. I could have recoiled at such a challenge but I was suddenly a man’s sexy, bedroom outfit clad, girlfriend. I felt sexy like never before and my new found desire and need soon had me sucking him and taking almost three or four inches of him into my mouth and throat.

My lips and mouth was stretched to the limit as I looked up at John’s face. His eyes were closed and he was moaning. All the times I said no to a guy and now I had more control than I ever had over a man, yet I would soon have little or none! “Oh Cari” He moaned deeply. Soon I was being lifted. I was being carried into my own bedroom by a very large, handsome, completely naked man!

John placed me gently onto my bed on my back. When his mouth met mine feeling his manly, hard, naked body pressed against mine was pure heaven. My disbelief and wonder surged as he lifted my nighty to find his lips meeting my boyish soft breasts. He first suckled them gently causing me to feel such an astonishing feminine sensation that caused me to groan in blissful delight. Then my lover began to suck and knead my breasts with a rapturous fervor that had me feeling euphoric and filled with lustful need. If I didn’t feel completely female and feminine, John was sure making me feel enraptured, loved, and so much more!

I was so hard and stimulated that my seven inch terribly hard cock almost hurt. I soon found myself having my legs lifted and my whole body bent back. John kissed my inner thighs and seemed to ignore my 7 inches of what seemed to be very incongruous manhood. With my 5” inch stilettoes helplessly pointing to the ceiling my thighs and my sexy round bottom was being spread by his huge powerful hands.

I felt his warm tongue gently lick the area around my anal opening. He was teasing me with his tongue and he was searching incredibly close to my entrance. When his tongue found my button down there I truly thought I would lose my mind! Bent back and helpless but so willingly submitting, I could not have been more moved. Feeling his powerful tongue soon probing me and even penetrating my anal opening and rim was the most mind blowing feeling I had ever experienced. I was practically hyperventilating at the eroticism and wonder of the feeling of being kissed and licked down there in my most personal place!

I was so ready for what I knew was going to be inevitable. My hairless smooth perfumed body was his to take. I was now willing beyond and even eager to see what really being a girl would be like. The “Girls” at the club talked about being fucked in the ass and I knew without doubt that John had plans for me and the sexy bum many a man had wanted. The only problem I knew was going to be his incredulous size. I didn’t care in my needy, wanton state. John was Lubricating my bottom so thoroughly that I was relaxed as I’d ever been down there. I knew this man had skill. I was mad in exhorting these squealing and whining sounds and I was yelping “OH GOD” in high pitched shrill shrieks.

To say that I was willing and ready to explore the new experience of truly being a female to a man was totally truthful. I never even thought about protection because I had not consciously planned on having sex at all. The girls at the club always said they did, especially the hookers and those naughty “girls” who just loved a good fuck. Perhaps when I showed up at my door greeting John in a sheer nighty and heels I must have had some kind of plan that I was knowingly willing to admit to. Now I realized that what was about to happen was something that I really must have wanted deep in my repressed and inhibited mind.

How ironic was it that my first guy would be more the size of a stallion than a man? I was ready but as John pulled me to him I stole a peek at his cock and feared that getting something that size inside me might not at all be possible. Strangely I was so lathered, so needy and so worked up into a sexual frenzy that I so wanted to try! He took hold of my thighs and spread them. John centered himself onto my opening with my high heels on his shoulders. I was about to be skewered, if it was humanly possible.

John rubbed his cock against my opening. He pressed forward and he slid away. He rubbed my button again with his huge missile and again pushed forward. He felt like a fire hydrant. It would likely be impossible. He was just so big and oversized. Suddenly Jon pressed harder and with a hard, fast push I shrieked as I felt like I was being split in two. The pain was immense, sharp and I screamed like a girl being spanked!

John knew he was hurting me and paused. His cockhead was just inside me nut he felt more like a telephone pole. He pressed gently forward but the pain returned as I growled almost crying and whimpering in frustration. I wanted him but he was way too big. John held me tight and bent over and kissed me. His tongue swirled in my mouth as the passionate French kiss re-inflamed my passions. He rocked forward and back gently as he told me to take a few deep breaths.

I was willing to cooperate and did precisely what I was told. I did relax some and John’s slow, careful fuck strokes eased himself a little further into my insides. The pain was tolerable because I so wanted him inside me. I breathed deeply again and soon John’s gentle fuck strokes became more forceful and I in spite of feeling overwhelmed and realized my lover was now quite a ways inside me. When his lips met mine again I relaxed. I was being fucked and the pain was ebbing and even tolerable. Each fuck stroke found me unconsciously reacting to meet each thrust.

I was fortunate to have such a skillful lover as my first. John was making me feel better and at times even wondrous, even though he was far from all the way inside of my needy and overfilled ass. Now he had me as his. I was in need of each and every one of his thrusts. He went deeper and deeper and it began to feel astounding and wondrous. His fuck strokes were firm and yet gentle and I was astonished at the pleasure, sensuality and gratification his huge, thick cock was bringing to my entire essence!

As John’s fuck strokes quickened I found myself clinging to him for dear life. My hands and nails were passionately and almost desperately dug into his back and backside. He was bringing me joy with a man tool that was almost too enormous for such an act. Suddenly John surged deeper and deeper into me when I felt a dull and then sharper pain. I groaned and screeched. He was hurting me and John realized why. My prostate was being victimized by his hugeness and yet John had an answer for that!

John stopped momentarily and moved his cock in an almost twisting manner. He was gentle as he pushed further forward. Again I felt pain, but inexplicably it ebbed. I felt him even deeper inside of my most personal of places. He was now past and beyond my prostate and now his fuck strokes were smoother but now even more frenetic. Soon I heard slapping sounds in the room as John’s balls and pelvis were meeting my smooth, wiling derriere. John was completely and totally inside me. I felt a sense of joy, bliss and even rapture that I couldn’t even begin to explain.

Again John’s lips met mine. Now he had me pinned backwards beneath him, my ankles in his large strong hands. His fuck stroked were now furious and I was beyond overwhelmed in a mixture of pain, pleasure, exultation and confusion. I was being used completely for his pleasure and yet I was loving every fuck stroke in spite of being barely able to breathe. Having almost ten inches of hard, thick man meat pounding my never explored and deepest places was incredulously overpowering. I couldn’t believe my state and my fate. I was on complete overload and my senses were engulfed in the solitary act of being the receiver of his powerful, and prodigious manhood.

John whispered to me telling me how wonderful I felt. I think my eyes were crossed and I couldn’t even reply. So overpowered and so helpless, I could only hold on for dear life as he rode my body into an intense all-consuming madness. As the rapid machine gun like spanking sounds of my ass being pounded filled the room, suddenly John growled and groaned. I felt heat in a very deep place in my depths. Dizzied and weak I knew he was releasing his swimmers into my body in hot spewing spasm after spasm.

I was so moved and stunned by his release that suddenly I too lost all control. I began an orgasm that was so deep and so atomic that I saw stars, the moon and so much more. I was in orgasmic heaven and my body quaked and trembled for minute after minute. I groaned and squealed in confused rapture and joy as John continued his thrusts until the pleasure tremors and explosions came to a gentle, yet mind blowing end.

The intensity of my very anal and almost whole body orgasm left me stunned and yet feeling fulfilled like I’d never felt before. The irony of being so filled with “him” being so emotionally, spiritually and physically meaningful to me. Now I felt more female and more like a woman than ever had and I was near tears in the elation and thrill of how I had been treated. It was so hard to believe that what had just happened was so real because it was like a trip to heaven only it was in my own bedroom! A man like John and his huge cock was all that had been missing all this time!

John lay atop me motionless as he kissed my neck and then lips as our heaving breathless bodies slowly faded into bliss. “Are you all right Cari?” John asked. Feeling very close to my lover I responded honestly - “Oh yes darling” I replied. I had a broad smile and calling John darling put a big smile on his face as well. We hugged still literally pasted and stuck together from the perspiration and my own ejaculated sperm that had us almost glued together. After many wondrous kisses I felt his still hard cock move inside me. “Ooh you feel so good John” I said sincerely.

John’s fuck motions began again and each stroke was excruciating delight. Slowly I felt him again spreading and stretching my insides. I gasped in full appreciation of his skill and his talent as a lover. This stud was ready for more and I certainly was not objecting. I’d learn to ride him atop him and bring him pleasure while sitting and enthusiastically riding on top of his huge ballistic missile. We would make love for almost the entirety of the night.  John was an adept and gifted lover and my life would forever be changed. I was no longer a just a “teaser”. I had a lot of time to make up for – now that I had become a girl and a pleaser!

John and I were together constantly for many months as weekend lovers. John was open about being a married man and I believe that made me comfortable in my wonderful role as a man’s mistress. I did not have to worry about complications. Life could not have been better until six months later when he announced that he wanted to leave his wife for me. I had been so lost in the joy of simply being treated so completely as a woman sexually that I never imagined our arrangement or our mutual expectations could change so much.

Being loved and so often bred by him was always the most magical and powerfully sexual experience I could imagine. I was in love with his cock and with the whole idea of being a woman for a man. Being his mistress was a very real fantasy yet true reality - that I so valued and was in love with. I couldn’t live with the expectation that he wanted to be with me forever – especially when I lived and enjoyed being a male as during the week. I was trying to find a future through a college education and I loved my duality far more - in spite of the magic of our relationship.

I would never have unprotected sex in the future. I am lucky I didn’t get “pregnant” with a disease! I would attract and meet perhaps too many men during the next months. I would have some rather wild carnal experiences with a few of them. I at least found a place where being a female on the weekend and a guy during the week – really worked well for me. I am now exploring some rather kinky things with a couple of male friends – but that is a whole other story that someday I might share! Being a man’s mistress as a very pretty boy turned woman is an experience I will always savor and remember in only the most positive of ways! I am a very, very lucky “gal!”