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All The Little Dresses

"A pretty crossdresser finds the reasons for her dressing."

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Author's Notes

"A true story of personal growth"

Since my very first public appearance as a fledgling gurl at the very young age of sixteen, I have collected over two dozen little dresses. In high school, I was a long-haired somewhat pretty boy who was popular mostly with the girls. For whatever reason I had a feminine side that needed to be liberated and freed. I found secretive times to be dressed up in girls’ clothing. It was my ambition and obsessive goal to become a pretty, believable, cross-dressed female in my future.

At seventeen, I was fortunate to enter college with the perfect off-campus single-bedroom apartment. I had hoped for this privacy which was perfect for feeding the secret gurl in my heart and soul. I worked hard at every skill necessary to be very pretty and convincing and my naturally feminine features would go a long way in helping with my dreams.

In what would become regular weekend quests, I would visit alternative nightclubs in Boston, appearing in my tiny sexy dresses, sexy high heels, and in my impeccable makeup. At only 5’5” and 125 pounds, I had the body type to fit into body-clinging size four dresses. I easily had the courage to make myself smooth-shaven all over. I boldly continued to grow out my fully shoulder-length dirty blonde hair. In the mirror, I really did look like a very pretty and quite convincing girl!

With a cute little nose, pierced ears, bright red lipstick, well-defined make-up and almost scandalously short skirts and dresses, I attracted a lot of attention at the clubs. At first, I was afraid, and even often repulsed by lecherous, overtly forward men, causing me to retreat to making friends with the many cross-dressed and transgendered girls who frequented the two-night clubs that I would visit in Boston. It would take time before I felt comfortable talking to men at all.

I was both naïve and had well-founded trust issues in these bars. They truly resembled the dangerous Star Wars Bar at times! Occasionally I would thank men for the many drinks I was bought. I was even uncomfortable doing that in those first weeks out. Men seemed to want to be owed for the favor, making it quite a process for me. I also didn’t know if I even liked men, especially when dressed as a woman.

What college gurl didn’t like free drinks though! Being a sexy flirt was dangerous but kept the cost of going out down! Eventually, I became more comfortable with myself. I could be flirtatious and accepted that I was a teaser and not a pleaser. My feelings and my emotions were all over the place but would change. I admit it was much to my surprise.

Men always called me the sexiest gurl in the bar. It was flattering yet it wasn’t until I danced with a man that I had any whisper of what true attraction for a guy could be. The feeling of being held close and then the shocking first unexpected tender kiss made me realize that I might have another avenue to explore! I was smitten by the affection and the momentous feeling of being so feminine and vulnerable in a man’s arms. It literally took away my breath.

I was changing. By mid-winter, he was my boyfriend! He was mature, over twice my age, and treated me like gold.  He would take me back to his home and the sex was stunning. Being a girl in this man’s arms was a powerful and almost magical experience for me. I now knew why I dressed so attractively and provocatively!

Once I realized that my attraction for certain older men was genuine and real, I began to allow myself further explorations that I could have never even dreamed of. A little over a year later I met a man who would change most every assumption that I had about sexuality, who I was, and who I wanted to be. I had always feared truly being myself with a man. I had a strong, secretive need to be submissive and I knew that I found great joy in bringing pleasure to the right man. It fit my personal perception of the ideal female.

On one fateful summer night at the bar, I met William. He was handsome, well-dressed and incredulously funny. I have always been cautious and responsible, but I was instantly smitten with him. When he expressed a very sincere feeling of attractiveness and liking towards me, I was fawning over him. He was honest to a fault, explaining who he was and what he liked in a gurl like me. William was a shamelessly dominant man with a penchant for submissive gurls. I somehow just knew that I hoped and wanted that gurl to be me! He explained how he liked to bind, discipline, and treat a gurl, and most importantly, how he developed trust.

Having always secretly loved certain fetishes and sensual outfits, I was intrigued. My first boyfriend indulged me in one of my personal fetishes once. He bought me a naughty, lacy and sexy, maid’s outfit that I loved. He found it sexy too, but every time I wore it, I would soon find it being peeled off me! He found me very desirable in it, especially when I pretended to be his French maid! It was my first sensual role play and I just wish my boyfriend had treated me more often!

We agreed that on the following night William and I would meet at his suburban home. Even though William had been clear, little did I know just how much I would be indulged in role-play, sensuality, bondage, and more! Expectation one was that I show up to his door in a shamelessly revealing schoolgirl outfit. I had the perfect outfit for him, and my excitement was unmistakable. My want to be a submissive gurl for this dominant man was profound, real, and intense! In a way I felt that William would give me the opportunity to be the gurl I always wanted to be!

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Saturday evening was mind-blowing, intense, and exciting beyond my dreams. I showed up at his front door in my hot pink micro-mini skirt, teensy white and pink Chanel bikini top, and five-inch-high heeled pumps! William was delighted! The smile on my face and my curtsey to him said it all! I was ready to be naughty for him and I was more than willing to follow what he called Daddy’s Rules.

I was one hundred percent willing to listen, trust and obey. It takes a special man to get me to trust yet soon I acknowledged that William was now my Daddy, and that I was now his own gurl, property of him! I soon allowed myself to be locked and collared in pink leather and made naked in high heels and placed on my knees. With metal handcuffed hands locked behind me, I was more than ready. As Daddy presented his gift to me, I eagerly took every inch of his huge, thick, nine-inch manhood into my mouth and throat!

This scene was far from crazy to me. I never felt more alive, more stimulated, or more willing to please. The music of Daddy’s moans and the strain and thrill of swallowing him fully brought me surging joy and a focus that was rapturous and thrilling. My smooth hairless skin and hard throbbing cock seemed like opposites yet so right. I was pleasing Daddy and pleasing Daddy well!

There will soon be many lessons learned tonight. I would buy into each one of them. The most difficult would be steel urethral chastity. There was nothing ordinary about it. I refused to say no despite being half scared to death. Daddy used a lubricant to insert a three-inch, 3/16-inch-wide stainless-steel pin into my hard seven-inch dripping penis. He then threaded it onto a steel cage that enveloped my balls and cock, rendering me essentially useless as a male.

He then proceeded to fuck me in it while placing me on my back on the kitchen table! Still naked and in heels and collar, his entry was mind-blowing. Using lots of lubricant, he slowly pushed the biggest cock I’d ever taken into my insides and depths. I was in complete and total ecstasy! I blissfully interpreted my state to that of being a one hundred percent female. I was no longer male; I was a complete girl!

I thanked Daddy for every deep meaningful thrust! I was so turned on that when he came into his condom in my depths, I relaxed and orgasmed like a tornado. I screeched immediately though as the blockage of my genetic fluids from my chastity caused tremors in my male hood as my genetic fluids backed up into my bladder. It was a sensation I would avoid in the future. Another lesson learned! There is a clear reason for chastity!

Weekends became our life and place. The next Friday Night was even more unforgettable. Daddy wanted to capture my first breeding on film! In my collar and in sexy pink lingerie, stockings, garters and matching pink high heel sandals, I first showed the dual cameras my deep-throating skills. Next, on a long black leather futon, I was placed on my back. Daddy licked my bottom and most personal place as I panted and cooed in disbelief of the pleasure, he was bringing to me.

Next Daddy placed my high heels over his shoulders and centered his huge cock at my opening. His thrusts first hurt but the tears running down my face were those of pure joy and elation. For over twenty minutes I wailed in joyous submission as Daddy fucked me into a complete frenzy. “Oh, Daddy you’re the best!” I’d wail. “Oh, Daddy Thank You” I’d moan. “Who are you?” he’d ask. “I’m your property Daddy” I’d scream back. “I’m your Bitch Daddy” I’d squeal. The dynamic and circumstance was as obvious as can be. Ten minutes later it happened.

Daddy already knew me well enough to know how much my feeling his huge cock inside me felt. The next level was near, and he made sure the camera angles were just right. With a huge, deep groan and room-filling growl Daddy began his orgasm. I was already crazed but feeling the heat of his wildly ejaculating seed in my depths was just too much. My hard, spring-like, bouncing cock exploded onto my flat stomach and up to my chest. His thrusts were still so deep and impassioned that I saw stars.

When Daddy eased, I continued to explode. My body shook and my high-pitched wails of “Oh, God Daddy!” were desperate-sounding madness. I felt faint as if I would pass out as my body shuddered in pleasure-filled convulsions. I think I blacked out. I awoke to tender kisses and Daddy asking me if I was all right. I managed a weak smile.

“Oh, God! That was incredible, Daddy!” I blurted. “I love you, Daddy!” I blurted in a high-pitched screech.

To say this night was unforgettable is the purest truth. All caught on two video cameras as well! Some nights Daddy and I watch our first porno! I showed the camera my bottom and gaping opening, dripping with my Daddy’s breeding fluids! I did pass out during my orgasm and Daddy told me he loved me too! As incredulous as our relationship is, we still live our lives apart, but together on weekends. I am proudly owned, and Daddy says I’m ten times better than any man’s wife! I never thought I would express my female side so completely and with such delight.

Daddy is a truly special and unique man. He’s the first to say he’s not perfect, but I tend to strongly disagree with him on this one! We have been together for many months though we do now tend to go our own ways at times now. I’m still a dedicated college student, but I’m also a dedicated submissive to my wonderful and loving Daddy!

 

 

 

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Written by carichristi
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