I’ve been dressing up as a girl in dresses and going out in public for the past two years since entering college. My goal has always been to be as pretty and as believably female as possible, when I choose to dress up as a female. I am blessed with being short and slim with facial features that can make me very realistic in make-up. Blonde hair extensions, false eyelashes, and glue on nails complete a look that can be credibly convincing according to friends!

I have always tried to work my feminine appearance to what I would call the highest degree possible of myself. People tell me I often look quite believably female at times. This has helped me develop confidence in myself as Cari. I go out regularly as a woman to alternative nightclubs and I have become comfortable doing so in short skirts, dresses, and even very high sexy heels!

With a friend’s encouragement, I was talked into entering in an international transgender contest in Montreal, Canada. I have gotten help from friends who are make-up artists and who are skilled and have shared their talents with me. They have guided my abilities to be sexy and to be plausibly pretty.

Peter is a man who became a good friend of mine. I met him in my hometown of Boston at a place that I call “The Club.” It is a small but popular transgender and gay bar in the Park Square area of the city. I have been going there since I was seventeen years old.

I have known Peter for almost two years. He is a true gentleman and we respect each other very much. He is my closest male friend. He watches out for me in the sometimes dangerous environment of the transgender clubs. We do not and have not slept together and that helps make our friendship very real and very special.

Being a student in college allows me incredible freedoms on the weekends. I have the privacy of having my own apartment. This enables me to go out to the club dressed in “drag” as my alter ego, Cari. Peter has almost always been there as an encourager and confidence person for me. It would be he who would convince me to give a transgender beauty contest a try!

On a dare, Peter generously entered me in an International Transgender Pageant in Montreal, Canada. He has often flattered me by telling me that I’m beautiful. He somehow convinced me that I could compete ably in this international beauty contest for transgendered girls. I’ve dabbled just a bit in Lip Synch at the club but I am far from great at it. It would be necessary for the talent portion of the contest.

Before leaving for Montreal, Peter and I decided we could be comfortable sharing a hotel room and would do so for the weekend. His generosity is why I got the opportunity. The night of the contest he supportively helped me in every way. I am so appreciative of him!

The contest was more elaborate than I could have imagined. I would be one of sixteen competitors who were called contest finalists. Apparently, Peter had represented me as a past winner from Boston! Still, I felt I couldn’t back out on him.

There was to be a talent contest (lip synch or real singing) and a bathing suit contest. I was frankly terrified at the prospect of going in front of hundreds of people, but Peter was there for me supportively telling me that I would be more than just fine.

I bravely tried to do my best. As competitor number four, I managed to simulate the singing of Whitney Houston’s “Run to You” with microphone in hand. Dressed in a borrowed, stunning, tight fitting, white sequined gown, I did feel that I looked glamorous and alluring. I focused hard on my acting as a real singer, expressively simulating the beautiful words and melody of the song.

When it was over I was stunned that I got quite an ovation! It was a true thrill. I did almost trip in my gown while being escorted off the stage! The bathing suit competition was next and I went straight to the dressing room. I knew I was in trouble when I looked around.

I was up against some of the sexiest and most feline looking creatures in North America! That dressing room was filled with incredulously sexy gals! As I changed, seeing the competition around me made me much less confident.

I put on a pretty, gold colored, and lightly sequined, deep v necked one piece bathing suit. The result left me looking a little flat as they say. Without any enhancements, I looked like a more like a real young teen gal on the beach than a glamorous girl! I was the antithesis of glitziness as I looked more like a high school cheerleader!

I was to go fourth again, and the third contestant was an absolute knock out. Her bright red hair, beautiful smooth complexion, and stunningly perfect breasts and body were incredible. Many transgendered women are the products of skilled plastic surgeons and she most certainly must have been. She wore a stunning red bikini with a sexy thong back!

I always thought that Halley Berry had the most spectacular body on a woman that I had ever seen. This Asian stunner may have outdone even her! I couldn’t help but wonder if she had already had gender reversal surgery. I could never tuck and hide my masculinity into a thong as skimpy as hers! Real women never looked as good as she did! I felt rather intimidated but Peter’s encouragement still helped keep my spirits from melting.

I was announced and took a deep breath. I did my best sensual strut. I managed a rather sexy sway while nervously walking in my five-inch gold stiletto high heels to the first station on the stage. I suddenly heard some applause. This encouraged me to work my sexy, petite, girlish bum a bit more! Suddenly heartened, it seemed that I had at least a few fans in the audience.

I skeptically wondered if my good friend Peter had made offers of drinks to them or something! The crowd’s affirmation did cheer me. I began to feel buoyant and more poised, as my long blonde tresses flowed while I now stylishly strutted. I was emboldened and wiggled my shapely round bottom across the stage for all to see. After my circuit, I posed hands on hips and with a big, genuine smile.

I had done it and without a slip! I saw my reflection across the club in the mirrored wall. The shining queen’s crown I wore just added to the dramatic, sexy, charisma that I appeared to have and was now even feeling. It had been only a forty-five second strut around the large stage, but it left me feeling feminine, thrilled, breathless and even inspired!

Now I took my place posing and smiling on the stage in the long girly line up across the side of the stage. I watched each of the rest of the girls do their sexiest walks. There were truly many wow moments!

Most of these girls were stunning yet I felt good about the amount of applause that I had so generously received compared to some of them. Win, lose or draw, I was glad that my good friend Peter had encouraged me to at least compete with and against these very beautiful ladies!

Peter held my hand while the winners were announced. Peter and I agreed that the stunning red headed beauty who went third was who we felt would win. They would announce fourth through first. When I shockingly heard my name called up as the second place winner I was stunned. I jumped in the air and hugged Peter and grinned from ear to ear. I was beyond thrilled to go up and get my blue ribbon and unexpected monetary prize!

This was just crazy. To finish as runner-up meant that I was worthy of competing in a beauty pageant. It was an incredible thrill to come in second place to the most beautiful, plastic surgery created creature that I had ever seen on this earth! I wasn’t at all disappointed because I am all natural “guy” without hormones or implants or injections.

My pride was in doing so well naturally without surgical help! The incredible redhead won going away as they say. She deserved it and the sight of her getting her prize had the entire crowd on their feet applauding. I applauded her enthusiastically. I was far from her level of beauty and wonder, but it was an honor to finish second to her.

Peter bought me drinks and we celebrated. Suddenly I was feeling things and emotions for Peter that I had never felt before. Everything Peter had said and done for me was just so selfless and generous. I was never more appreciative of a friend. It was well after midnight and the club stayed open until three!

I found myself getting a bit tipsy and found myself practically hanging all over him. I so liked this big, friendly guy who was my buddy and my encourager. Because of him, I was a real life “pageant queen” and Peter had helped make me feel like a true winner. I felt very lucky to have such a friend and admirer. Now I was admiring him!

Peter had some photos of the two of us taken together. With his arm around my waist and my arm around his back and broad shoulders, we posed and both smiled genuinely. I felt so girlishly feminine and so charmed by his closeness. When I saw the pictures of us on his phone, something struck me deep in my heart and soul! I saw a handsome attractive Daddy type of guy with a pretty little girl who seemed very much in like!

I realized that I was appreciating my good friend in more ways than I ever had! Both the drinks and my new gratitude for my number one fan had me in quite a state. I gave him a big, joyous hug and winked at him. I was feeling so naughty and drawn to him. I found Peter to be very attractive and wondered why we were just friends.

I’ve always had an attraction for older, sexy, quality men. Peter was over twice my age. I’m nineteen and Peter is forty-one, so in spite of our age difference, he is quite attractive to me and is my type of guy. I think I’m a Daddy’s girl type of gal and it only took a bit of liquor to remind me of my little weakness for men like him!

He toasted me and I looked him in the eyes with a smile. In both gratitude and in my new strong attraction for him I found myself gently and seductively caressed him in his crotch! Peter’s wide smile made me grin as well. With a hug and deep moving kiss, we were soon off to the hotel room for more than we had both planned on!

Peter is a very large man at six foot one and about two hundred seventy pounds. I weigh less than half his weight and while walking hand and hand back to the car I felt so tiny and vulnerable. His incredulous masculinity has me fawning. I was smitten and wondered why I had never felt this attracted to him. He was all man and we already knew that I was ready for complete surrender to him!

The ride up the hotel elevator was an unforgettable frenzy of heated passion. I couldn’t take my lips off of his and his strong hands lifted me against him so that I was literally pressed against the elevator wall with my high heels around his back. He pressed his manhood against me and I wanted to be fucked by him right there!

Fortunately, he was the more sensible one. We somehow made it to the room and bed without breeding in the elevator! I tore at his belt and his zipper like a needy, wanton slut. He had me naked in but seconds and I couldn’t keep my eyes off his huge hard manhood!

Like a greedy child I had my mouth on his huge cockhead in but seconds. I love pleasing a man orally and the taste of cock is delicious, especially when I care for the man. I wanted to show him just how skilled I was. I had my mouth all the way down his over eight-inch thick shaft after but a couple of attempts.

With Peter on his back, I looked up at him with a smile in my eyes. His eyes were practically rolling back in his head and I proudly and enthusiastically went to work on him. My pretty red lips were practically kissing his balls and pelvis and Peter seemed like he was losing his mind with his groans and grunts of pleasure.

I must have been pretty good at pleasing him because his “Oh God” cries were becoming more and more frenetic. I kept up my deep throating as I felt my own hardness stir in the joy of this act I so enjoy. Peter was perhaps quite near and he had plans that I too was hoping for.

In but a few more moments he was nude and his huge hulking body was pressed atop me. With my legs bent backwards and my high heels pointing to the ceiling, our kiss ended only to find him kissing me in a much more intimate and personal place! Peter knew exactly what I wanted and needed!

Still wearing my queen’s crown, it must have been quite a strange sight. In my naked, compromised position I was bent backwards on my back under him. My manly lover’s tongue began to make my anus feel some the most heaven like sensations a gal can experience. My boy cock was throbbing from the stimulation.

His aftershave and my perfume together dizzied me. My smooth little lithe fem body was already shivering from his every lick and touch! Nothing stimulates me more than having my anus explored like Peter was doing. “Oh God Daddy!” I squealed. This was so much more than a simple Daddy-Girl fantasy!

To add further to my arousal he paused to gently suckle my soft boyish breasts. This only aroused me more, causing me to practically hyperventilate from the feline sensations shooting through my body. Being treated like a woman in this manner is closest to my perfect ideal. Peter then returned his searching tongue and lips to my opening. He was turning it into a wet, softening, slippery tunnel that was making me ready for so much more!

Knowing each other so well was perhaps the reason we had no need to discuss rationale for what was next. I was literally biting my lip so as to not to be weak and to beg. I needed him more than I’d ever needed anyone it seemed. Peter was overwhelming me even though I knew he would most certainly oblige.

When I thought I was too overwhelmed by his rousing erotic, pleasure tortures, he relented and knew it was time. He carefully pressed his huge, thick cock into me and it was truly incredulous. In spite of the discomfort, I was overcome with a mix of pleasure-pain that as one might say – leaves a gal speechless!

A man of his size is not easily entertained into a girl’s bottom, but I was beyond ready and in need. I was going to insure that it would! As his huge body and cock pressed into me the overwhelming conquest of my tight entrance was not so much an invasion as it was as a very welcome relief! My body was becoming his and I relaxed my sphincter for him. I was a very willing conquest.

As each thick inch moved deeper into my needy bottom I cooed and cried out in joyous yelps and whines as each solid thrust hit home. “Oh yes Daddy yes!” I squealed, as the man who was just my good friend had become so much more. Now my wondrous, monstrously hung lover was now searching my depths and my wails just encouraged him onward.

I was so moved by his huge cock and became aware in the realization that he was so skillful. His fuck strokes were firm and aggressive, yet each purposeful thrust truly frazzled me. He was fucking me hard and so very deeply.

His unyielding, steady pumping of my bottom was magical. I felt he was making love to me and not just simply fucking me. I was getting more and more crazed by his skill. Helplessly and completely his - being beneath this wonderful man, was a surrender I was finding to be so amazing and so very sweet.

Peter was such a real man, and now proving how magnificent he was as a lover. I was becoming so moved. He was orchestrating and controlling me while slowly bringing me higher and higher. I squealed lusty whine while I tensely held his back and ass. In lust and near madness, I wondered why I had not succumbed to this, marvelously talented man months or even years earlier.

I was practically singing. I was awash in the extraordinary delight and the hedonism of having my ass thrill from the wonder of ache, hurt, and torturous joy and ecstasy. I was encouraging each and every powerful thrust when I began to quiver and shudder.

When Daddy’s lips met mine I almost cried into his greedy, delicious mouth. This was a thrilling rapture that had me smitten beyond thoughts. The elation from the hurt and pleasure was elevating my perceptions into a state of bliss and confused delight. Feeling both dumbfounded and yet aroused beyond madness, I knew I would be a goner sooner than later!

As our lips met again, his searching tongue and his more rapid thrusts had me near to insanity. To me, there is no greater celebration of my femininity than engaging in this act with an attractive, physically gifted and loving man. This very special, tender, supportive man made it so much better. I knew how much he cared for me and now I knew how much I appreciated everything about him.

Peter suddenly paused. My shrieking had caused him to ask me if I was okay. “Oh Yes, Daddy!” I yelped inexplicably. My frenetic cries and almost orgasmic surging had caused him to fear that he might be hurting me. My reaction assured him that I was simply in a crazed state of enjoying frenetic, levels of physical and even emotional pleasure. Peter soon treated me to rapid fire thrusts that had me on my way to the moon!

I am a somewhat unique girl-boy who has the capacity for true anal orgasm. In spite of being completely overwhelmed by his locomotive like power, I knew I’d be arriving at that station ahead of schedule! My Daddy’s fuck strokes soothed my spirit and rocked my body. This was the perfect nourishment for my feline soul. The quivering and shuddering in my body was already beginning. Being the pleaser by nature that I am - I began to beg my lover to cum. I had a crazy want and need to have him fill me with his genetic fluids!

I must admit that I have been bred once or twice before. It is a dangerous practice. I did so – in the two trusting relationships I had experienced. Having been sexually active for two years now, I thought of myself as smart – but I wasn’t thinking clearly in my state of mind!

I also thought that allowing myself to be bred was never going to happen again in my life. I did know Peter well enough to know that he was safe and smart - yet we hadn’t even talked about such a thing happening. This whole love struck evening had been all so unexpected.

Suddenly Peter lifted me. I felt helpless as I found myself rolled over – but still impaled by him. Peter was on his back and I was now sitting atop him with his huge hydrant like cock deep in my bottom. Now I was even more excited. I was the active pleaser and my need based instincts kicked in. Peter was giving me control and I was thrilled to oblige him.

We were both smiling as I began to ride Peter’s magnificent manhood. In high pitched wails, I was groaning and growling. The joy of being in control of my lover’s pleasure was an even greater pleasure for me. I was in the perfect place and I so felt like a real girl.

I found my bottom grinding all the way down his shaft and bending forward and back to feel and squeeze every inch of his wondrous cock deep into my anus and sphincter. My own rigid over stimulated organ bounced upward and downward wildly in a blur, while slapping his stomach.

Peter met my down thrusts with powerful up thrusts and we became one in our rapid-fire sexual unison. He was incredulously powerful in his ascending fuck motions almost sending me flying. I shrieked while sitting down on him meeting his up thrusts. Each stroke found my anal opening meeting his huge balls. This was such joy for me. The wonder and amazing pleasures reverberating all over and deep inside my body - had me marveling and dizzied in lustful elation and bliss.

I couldn’t get over my cocks hardness and spring like bouncing as I rode him. I’ve heard the term “flopping” when a boy-girl rides a man - but this was springing! The intensity was incomprehensible and I knew I’d soon be a goner. My concern was not for my own orgasm, but instead for his. A girl should always wait for her Daddy!

In a panic I was too near to losing all control. I began to beg him to explode. “Oh cum Daddy, cum!” I shrieked. I needed his breeding fluids inside me to savor and delight in. I so wanted to feel his swimmers inside me. My good friend Peter was now my Daddy and I so wanted Daddy to complete me as his girl - with his seed!

Daddy gripped my waist and began an even more frantic, bold and vigorous assault on my bottom. His up thrusting had me almost flying off of his huge cock only to find myself completely impaled and seated upon his balls and on his belly. My body was shaking and trembling all over. Just when I thought our lovemaking could be no more frenetic he began to growl. He was coming and appreciative tears began to roll down my pretty face.

As I felt the heat of his breeding fluids filling my depths it was my turn to see stars and more. My brain, body, and cock all exploded into the throes of an orgasm that was as powerful and as special as any I had ever experienced. Feeling the hot shots of his sperm filling my bottom sent me into heaven. Spasm after spasm of orgasmic quakes had me shuddering and reeling. I just screamed and squealed in naughty, high pitched, shameless words of delight.

I fell atop him stunned, dazed and dumbfounded. I was happy, amazed and beyond astounded. We were stuck together by perspiration when Daddy pulled me forward. My body and soul melted while he kissed me deeply. His kiss suddenly caused eruptions of orgasmic magic deep inside me to reignite! These tremors and delight waves inexplicably just kept seeming to repeat themselves!

I was breathless and so amazed. I never imagined that lovemaking could be more intense or more meaningful. As the final pleasure flashed finally ebbed, we couldn’t help but express ourselves with deeply meaningful kisses. His cock was still hard and felt like it belonged inside me. I never wanted this moment to end!

The amazing things between us just again began to continue. He was once again getting aroused. Our coupling had become so mutual and so wonderful that we both knew that we were quite special. This would be a night in which years of mutual appreciation would be expressed in so many treasured ways!

Now it’s clear we will always be good friends. The benefits are in the value and joy that we both cherish and experience with each other, including what happened on this weekend! I never expected to win the pageant – but it’s safe to say that we both won big – and shall we say, going away!