Becoming Daddy’s Girl   Leave a comment

Becoming Daddy’s Girl

By Cari Christi

After a year of having become a somewhat accomplished crossdresser, visiting the transvestite bar on weekend nights had become almost the norm for me. Only a month past my eighteenth birthday, I was both a “regular” and yet still one of the youngest people there. I was often told by men that I was the cutest, the prettiest, and the sexiest “little girl” in the bar.

I loved the recognition of being seen as being quite feminine, petite and being suggestively sensual. One night as I got comfortable on the bar stool I crossed my exposed smooth stocking covered legs and reflected on how it seemed so hard to believe how much had changed in the year since I first walked into this same scary Star Wars like bar dressed overtly in a teensy scandalous black dress, teased blonde wig and five inch high heels.

That first night (at age 17) was terrifying as more than a couple of the lusty naughty old half drunken men tried to corrupt me. Assuming I was a hooker, they had me fleeing from the bar in but a few minutes of my arrival. After that negative and quite scary experience I knew I had to develop more courage, resolve and confidence if I wanted to be out in public as “Cari.” I had to protect myself from the many sleazy characters at this club that catered to transgender, gay, straight and bisexual folks.

What helped me most was my developing friendship with the bartender. He helped me understand the madness of the club’s environment as my naiveté was quite natural due to my youth and lack of experience. “Johnny” also liked how I tipped and helped by always telling me who it was safe to talk to and with whom it was not.

Johnny was my official protector there and even introduced me to a nice older man with whom I shyly developed a friendship. In time it grew to a bit more and after almost a year it was on my first date as a “gal” with him – that my life unexpectedly changed far more than I ever would have dreamed or wanted.

At the time I felt so guilty for surrendering to a man. I did not realize how powerful it was to be female in the arms of a man. I actually came to enjoy being this man’s “girlfriend” for a few weeks, but my surrender signaled the beginning of how I came to change and evolve into a new view of my femininity in the future.

As an attractively dressed 5’5” 130 pound slim, blonde and femininely made up and perfumed gal – I was fortunate or “unlucky” (depending on one’s point of view) to be constantly ogled and approached by men and even the occasional woman. Now that I was no longer the complete virginal innocent, I was now at least swimming a little more comfortably in this club’s dubious ocean filled with everything from minnows to sharks!

I naturally began fantasizing about scenarios that were more erotic and more feminine in nature. I pushed the feminine envelope in my dress and behavior but I was still a “shy girl”. I was not particularly overt about my sexuality because I was still a little in denial of my first affair. I had a girl friend of mine that I befriended at the club who loved bondage and discipline. At the time it seemed far too extreme but at least fascinating to me. People at a club like this seemed to love all kinds of kinky things and I must admit I was at least quite curious.

In my personal fantasy world I found Lingerie models and French Maids to be just a couple of many ideals I thought were ultra – feline. When a casual conversation with a man at the bar that “Johnny” endorsed went to a discussion of my own personal fantasies – I found myself being bought many a drink by him. Suddenly I was more than willing to share what was perhaps far too much with him.

Roger was a unique man and perhaps the most popular male character at the bar. At almost six and a half feet tall he was very manly, quite comical and very outgoing. He looked like and was built like a professional football player and had a natural way of owning a room.

When Roger arrived at the bar it was always like it was when the party started. His humor and generosity was always on full display. All the girls flocked to him and he bought many a round for the girls and even the entire bar. He was unique in so many ways – especially in a place where there was far more desperation than charity and more frustration than kindness.

I was always flattered when he showed an interest in me but it wasn’t until one of my girl-friends told me that was quite smitten by me that I would never have known otherwise. I loved it when he bought me drinks and joked with me. He was genuinely funny and articulate. He was also a very successful broker in the investment industry. I always seemed drawn to class and elegance and he was unique in the Jacques Ocean!

Roger well was over twice my age and literally more than twice my size. I found myself being drawn to him in ways I had never before had understood. In some ways he was like a Father figure to me and others he was both a protector and friend. He would walk me to my car at the end of many a night. When our discussions eventually led to my fantasies on that crazy night – I spilled more in my inebriated state than I have ever admitted to anyone ever.

Another first for me was handing him my address along with my cell phone number that very night. Though I was at college here in Boston on weekdays, I lived in the city and was all guy during the week. Dressing up was a hobby and a love – but not a way of life for me except on the weekend.

Perhaps thanks to the bartender’s advice I found myself trusting him implicitly. I never had trusted anyone this completely, even the man with whom I had first became a “girlfriend” to. I admitted I would look forward to meeting him at the bar the next week and we planned to do so.

On Wednesday when I got back from class, there was a package waiting at the door of my apartment. I couldn’t figure out where it came from but it was marked “urgent”. It also had my female name on it and I was embarrassed about that! It had come via UPS and was apparently from a woman’s clothing store. Inside I found a small red plaid skirt, a short sexy semi sheer white blouse, white stockings, a black bra, and a garter belt! There was a card in an envelope and I kind of knew who was responsible for my gift even before opening it!

The “schoolgirl” outfit was one of the fantasies we had both talked about. I was shaking in nervousness and a strange excitement as I tried to open the note. It was short and simple. “Hi Cari – I believe in helping people’s fantasies come true. Do you dare?” – Love “Daddy” PS I’ll call you soon.

So many emotions hit me at the same time. I was stunned, happy, scared, excited, aroused and afraid I had been far too honest. I found the sensual items so irresistible – I had to see if these items fit. I grabbed a pair of my five inch white high heels and got immediately dressed.

As I tried on the dress and the blouse they fit perfectly. Suddenly I recalled more of our late night conversation. Plied with a half dozen free drinks I’d spilled everything from my waist size to my dress size to him when he had asked. He had a plan even then. I was embarrassed yet actually quite flattered by it all.

The feel of female clothing was the powerful aphrodisiac that was probably responsible for my first dressing as a girl as a child. I was smitten and in the mirror I looked so hot and naughty. Even without make – up and one of my many wigs I looked incredulously female and decadently hot.­ My smooth, slim, completely shaven body looked great in clothes like this! Just the idea of being this tempting young school girlish creature made me crazy with lust – yet was I that naughty and bold to ever dare to wear this alluring “tease outfit” for a man?

At 6:30 the phone rang and I purposely answered the phone with a quite soft and sexy feminine voice. I had jokingly entered his number into my phone identified as Daddy and seeing the word “Daddy” come up on my phone lit me into the fantasy almost immediately. My voice was super feminine and I swooned when he told me how much he enjoyed meeting me and that he likes me very much. He asked if I still planned on meet him Saturday and I let him know how enthused I was.

I think he wanted me to be the one to mention “the package”. Finally, after a few fun minutes of small talk, I told him to guess what came in the mail for me. He simply asked me if I liked it. In lots of words I told him how much I LOVED the outfit. When he asked “Would you wear it for me?”- I was almost afraid to answer. I was never more torn. I didn’t want to be a “slut” – yet this nice man was reminding me about the kind of “opportunity” that I had fantasized about!

In a combination of lust, emotion and doubt – I blurted out “I would like that.” I didn’t know if I REALLY meant it but at least half of my soul NEEDED to wear that outfit for him. It was the exciting chance I had dreamed of ONLY if I had the true courage to explore my dreams.

He invited me over to his house Friday Night! He told me that my “Daddy” would love to see his little girl knock on his door all dressed up pretty and sexy in the outfit for him. Suddenly this was all so real. My heart raced and yet my cock hardened! I couldn’t believe that at 7:00 PM on Friday night – This guy who was willing to be “My Daddy” was expecting to see “his girl” knocking on his door in a naughty school girl outfit that left little if anything to the imagination of any man. Could I dare do as I was being asked? Daddy said he would be waiting right at the door for me with a big smile!

Friday at college was an emotional disaster. I didn’t hear either of my professors lectures because my mind was torn up in conflict. I knew I would go home and get dressed in that delicious outfit – but would I dare do it for him? I would definitely get all dressed up…..

At home I made myself up to perfection. My longer length two tone blonde wig made my face seem so sexy and yet innocent. The look was as perfect as was the outfit. My short blouse revealed my flat stomach and naturally narrow waist. The skirt revealed my smooth sexy legs in complete and my smooth round ass could be seen with ease. I just had to add a tight stretch set of panties to cover my bulging 7 plus inch male-hood! The garters and white stockings were in full view. This outfit had almost way too much purpose! It was worth much more than a thousand words!

I never felt hotter and more sensual as I thought of myself showing up like I was dressed at his front door. Could I dare do it? I knew “Daddy” was hoping his little girl would! Men like nothing more than a very good and well behaved girl!

I took many deep breaths knowing it would take about twenty minutes to drive to his suburban home. I decided I would dare try to do it! I would leave early to give myself time to think – and if I decided to courageously knock on the door – I’d at least be there on time. I walked to my car in the cool evening breeze covered up by a light knee length trench coat. I slipped off my high white five inch sandal style heels to insure my driving safety.

After a twenty minute drive, I found the huge almost mansion like home while scouting the distance from the circular driveway to the front entrance. It was only a small number of steps but at Seven PM it would still be prior to sunset and darkness was still far away.

I knew Daddy wanted to see “his naughty school girl’ arrive and parade for him looking so naughty all the way to his elegant front door. As my excitement grew so did my trepidation. There were neighbors across the street and I could easily be seen. Suddenly after a look in the mirror I winked at myself! I knew I wanted to do it! The next time I swung by the house I took a deep breath and drove right into the circular driveway and then parked as close to the front as I could.

I looked out the car windows and realized I didn’t have but a dozen or so steps and just 5 stairs before I could do as asked. I removed my coat, adjusted my skirt and checked my reflection in the rear view mirror. My excitement surged and after another deep breath I opened the door. I nearly fell as I exited my car!

I steadied myself in my 5” high heels and walked quickly to and up the stairs. I felt naked and so exposed on the front porch and wasted little time knocking on the door. I heard a voice – “Just a minute” and as I stood I realized just how truly exposed I was. I looked down at my legs and high heels. I could see my panties bulging! I was here dressed in complete naughtiness for him. What a naughty slut I thought! I guess I was more than ready to be Daddy’s little girl!

It seemed like forever before he opened the door. I think he wanted to remind me just how sexy and exposed I was out there. Standing on his doorstep dressed like such a shameless seductress only heightened my excitement but my insecurity as well. When the door finally opened I realized that his smile was what made me feel so comfortable with him.

I got a huge hug and kiss and suddenly everything seemed all right in the world. In his arms I felt tiny and little girl like. I had already surrendered myself dressed like a sexy and wanton school girl in the most revealing outfit that I had ever worn out in public. I felt a little proud, a little embarrassed, very sexy, and suddenly very accepted for the shamefully naughty girl who I had become. I had done this all for him!

Hearing that Daddy was very happy with “his girl” only made my comfort and happiness surge as he took me by the hand and welcomed me into his elegant home. It was huge and perfectly decorated and he took my hand and walked me to a large mirror on the wall of the large cool living room. As my ridiculously high heels clicked on the hardwood floor I felt wondrous to have surrendered myself to the comfortable trust of this friendly and seemingly caring and quite handsome older man.

I came knew that I was quite emotionally prepared to surrender myself sexually to Daddy and we both knew it. In my drunken honesty a week earlier I had already confessed and admitted my want for various feline surrender fantasies and I was already in almost a state of complete comfort in our role play. Now I felt so sexy and coddled because my “Daddy” seemed very pleased with his “little girl.”

In the mirror I saw my reflection as I felt so tiny and vulnerable next to him. We both smiled broadly at my teensy plaid mini skirt and skin revealing “outfit”. He told me how pretty I was and that I looked just like a high school girl – only much hotter! When Daddy told me I needed a spanking for being dressed in so naughty a way I felt a bit confused at first. He by the hand to the couch and had me lay on his lap on the couch. Now it seemed to make all the sense in the world to me. I was a “naughty girl” dressed like a seductive school girl – and I knew I deserved a spanking from my Daddy!

Daddy pulled down my panties. As I got a few coy and gentle spanks to my naked bottom I found myself lighting up in excitement. For the first time in my life I was thrilled with what felt like was complete surrender. As Daddy’s firm spanks got a bit more severe I found my cock straining in my panties. I was more than enjoying the heat my bottom was getting from my Daddy’s huge hand! All the time Daddy checked in with his little girl making sure it did not hurt too much but also getting me to admit to him that I was indeed a naughty girl!

When Daddy asked I told Daddy I promised that I would be a good girl for him. I had accepted completely Daddy’s suggestion that naughty girls deserved a good spanking and the fact that I was getting very aroused only convinced me Daddy knew exactly what his girl needed!

The kisses after he heated my bottom had me swooning and feeling like a little girl who had fallen in love. Daddy told me he had another present for me. I was thrilled and excited and when I learned that it was a sexy black bustier. It was boned, covered and edged in silk lace. When Daddy stripped me naked he slid it onto me and tightened the laces in the back. My waist was so spectacularly narrowed and in the mirror I looked so breathlessly feminine that I never wanted more to be made love to in my young life.

Just one of the many things I loved about Daddy was that he treated me like I was a delicate little flower. He also kindly allowed me to decide on many things at first especially in regard to sexuality. He asked me if I would like to suck his cock. I would reply eagerly with “Yes Daddy” like an innocent girl yet with lots of enthusiasm. I wanted so much to please him and I did my best. Being not the most experienced gal in the world – did not stop me from being pretty good at being a pleasure girl!

Though Daddy was only my second guy, I did seem to end up with guys with huge cocks. Daddy was so well endowed it was incredulous. I went to my knees for him while fearing that his eight inch monster cock was so thick that I had real doubts about my ability to succeed. His cock head was huge and mushroom like and just the act of getting it into my mouth was quite a feat! In spite, I never felt more ready and willing to please and I found a way to take him almost fully and very deeply into my very willing mouth and throat. I was so pleased to hear Daddy’s moans and the many compliments he gave to his good girl! It just made me more and more willing and even enthused to please him!

As I looked up at my Daddy’s face I knew just how right my “role” was. Even though I was half choked and in a bit of duress with his size, seeing his face and hearing his moans of pleasure had my cock swollen and hard as a rock. I never was aware at how much sucking a man’s cock could excite me but I was in heaven in my role and the knowledge that my Daddy was enjoying his girl’s actions and behavior quite clearly. He was as hard as I was greatly enjoying my girlish enthusiasm. He lifted me fearing I would make him go off in my mouth!

Daddy’s bedroom had a full walled mirror next to the bed and for me being able to glance and see me as a stunning and attractive girl in a man’s arms only added to the celebration of my role. Using lubricant and a condom Daddy wanted to start our lovemaking by mercifully having his little girl sit on top of him. It took considerable relaxation techniques on my part to get his huge cockhead inside me. My sphincter strained but once inside me I worked with a great deal of struggle to accept inch after inch until I began to ride my Daddy with genuine and lustful enthusiasm.

Even better was seeing our reflection in the mirror. Having left the lights on was such a great idea. Daddy and his little girl could see the love dance taking place atop his bed. I was so smitten with what I believed to be a beautiful blonde 100% “GIRL” with a teensy wasp like waist riding atop a huge man’s thick cock that I forgot that my dripping, pulsing cock was bouncing frenetically atop his stomach! I could clearly see his huge cock disappearing then re-appearing from my backside.

I was never more turned on by sex or a scene more vividly moving. After perhaps only five minutes of lusty enthusiastic cock riding I was getting crazed in lust and sexual heat. I was finally letting go as a woman. My screams and screeches were becoming so high pitched and so frantic and frenzied. Feeling a big, hard appreciative man so deep inside my girlish body frenzied me beyond belief. It was only natural that my lover responded in complete. Grabbing my tight fitting bustier at the waist he cooperated fully in pulling his girl up and down along his monster shaft so furiously that his little girl was soon a goner!

There are orgasms and there are incredulous mind blowing nuclear anal orgasms. Mine was certainly the latter. Never had I orgasmed simply from anal penetration and never had I felt shivers, quivers and warmth consume my body literally from my toes to my head. I saw stars and felt glorious sensations so pleasurable and powerful that all I could do was fall forward to his face as eruption after eruption overwhelmed me as never before. Breathlessly I cried out with each pulsing eruption until the quivering and full body pleasure waves gradually subsided. I could not believe the splendor and power of what had happened to my entire essence. I covered hi belly with spurt after uncontrollable spurt of my sperm.

Suddenly Daddy began groaning and thrusting wildly and I was so thrilled that I fully and enthusiastically cooperated in meeting each and every powerful up thrust with a synchronistic down thrust. In moments I could feel the heat and warmth inside me in spite of the insulation of the latex that kept my bottom from being filled with his love fluids. Daddy was coming and I was every bit as thrilled as he. To say we were both moved was an understatement of epic proportion.

We kissed and hugged for what seemed like hours completely satiated by our lusty lovemaking. Daddy whispered wondrously naughty compliments in his girl’s ear. Our dialogue was so mutually complimentary that it was truly fun and filled with many an enthusiastic “Oh Yes Daddy!” comment – that was almost comical in nature coming from my bright red lips. There would be many more hours of praise and commendations including quite a bit more Daddy-girl love in his bedroom on this wondrous night!

Daddy and “his little girl” soon became not only “a couple” but also the confluence of what seemed to be the ideal balance of fantasy made reality. He and I so loved to find those things that we both fantasized about and it seemed he always found a way to make happen. Next I was a French Maid. The minimalistic lacy, sizzling, erotically sensual Maid outfits he bought for me were sexy beyond belief.

“His Maid” would later help host a party and serve drinks and food in six inch high heels to Daddy’s guests. At that party I would “serve” “My Daddy” in some very public and sexual ways proving to all that I was Daddy’s good little girl. The people form the club came to know us as in our roles. I was always proud to be “his” in public and I respectfully called him Daddy at the club soon after our first night together. I was no longer ashamed to be a man’s girl!

Two weeks later Daddy helped make another incredulous mutual fantasy came true. In an elegant, rented Vermont Ski Chalet, we celebrated our simulated “honeymoon” together as both ”Husband and Wife!” I was literally carried over the threshold “by my husband” in a sensational sexy white lace mini wedding dress, which I wore for the entire trip to Vermont while in the car. The sexual energy and anticipation during the 3 hour ride had me doing things a couple of truckers may have viewed in the car! I even got kisses from him at a gas station in front of many clapping people who assumed it was our true reality!

All of the splendidly white lace lingerie bought by Daddy for the occasion saw lots of use! That weekend we even celebrated our mock wedding by something very real. I was willingly and completely bred for the first time by my “Husband” and though I didn’t get “pregnant” – being “bred” was just a true highlight of our fantasy and reality life that I will always truly cherish! It was one of the most wondrously intimate, enjoyable, and gratifying experiences in my life! Feeling a man empty every drop of his breeding fluids into me was more than just spiritual. It was a dream come true.

Daddy and I were together as a “couple” for well over a year. The fantasy scenarios grew comfortably and in ways that were always mutually gratifying. We did some wildly daring and exciting things in our “Daddy’s little girl” relationship. His influences forever shaped my view of femininity and the joy of being a transvestite and “girl”. To experience “love” in both a literal and a true fantasy sense as we did was mind blowing and wonderful beyond explanation. As fantasy friends we were both lovers and in reality we were in love in many, many ways.

Because of the success of my passionate and exciting experiences with “Daddy”, I would continue to explore the joys of fantasy and reality. I must admit that in many ways I feel like one of the most fortunate and luckiest people on earth! At times I really both believe that I am and feel that I am female. Being able to live life as both a male and as a female is an awesome and humbling gift that just keeps on giving! “Thanks Daddy – and you do know that I love you very much Daddy!”

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Posted November 21, 2015 by missjames64 in A how to post, Author Cari Christi, New Life

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