Feminine Fate Fulfilled Ch. 01

I would like to thank my friend Georgia Alice for her help with naming the characters.

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THE BEGINNING

Apparently appearance can determine fate, at least it turned out to be true in my case. In order to explain my point I first need to describe myself with the necessary details. So let me start again.

Hello, my name is Oliver and I am an eighteen year old guy. I have never been the most masculine of boys to say the least, but even now with my birthday taking place six months ago I was still sometimes confused for a girl by strangers. At 175 centimetres I was on the short side of average, but I did not complain. What had bothered me were my hips and buttocks; seriously, they were girly. I did not possess a JLo booty, but had visibly wider hips and fuller buttocks. This was an issue because I had hard times buying pants and eventually had no choice but to buy tight but stretchable ones. My legs were kinda girly as well although that was not necessarily a bad thing - they were long, slender and I have even heard from girls that they would love to have such sexy legs. My torso was not overly manly either, I was slender but not a wimp. I had tried to gain some muscles and had been doing all kinds of sports since early teens, but all I managed to accomplish was a toned slim body, something you would expect from a female fitness instructor. With the general lack of body hair I kind of looked like a flat chested athletic girl. To be honest my hidden inner narcist sometimes urged me to admire my own naked body, especially the lower parts, in the mirror.

My face was described by girls as "incredibly cute", they meant it as a compliment, but I saw my own face as rather androgynous. I also had fabulous hair, I understood perfectly well that keeping my blonde hair long made me look even more girly, but I loved it nevertheless. My hair was naturally light, thick, slightly wavy and healthy. The girls envied me even more because of that than because of my legs.

The one thing perfectly manly about my body was my penis of which I was rather proud. In a flaccid state it looked average, but when it got fully erect it was twenty one centimetres long and four thick. I had not yet had a chance to satisfy a girl with it though.

My looks were not a problem at school, it was a good facility with no bullies whatsoever; although friendly jokes about my "phat ass" were quite common. I was relatively popular with girls and even had a girlfriend for the last three months. Her name was Dani and she was a real stunner.

She was of the same height as I, had a slim athletic body but with all the proper curves; her breasts were a nice firm C-cups. She had a pretty face surrounded by long wavy auburn hair.

I said that we were of the same height which was true, but often Dani seemed taller than me because she loved high heels. That was not an issue for either of us, although she joked from time to time that my long slender legs would look as sexy as hers in a pair of high heels.

We were both just eighteen and still virgins, after being together for three months we have not done more than just make out. Although all the kissing and touching was hot, I felt that Dani was even more eager to grope my butt than I was hers. She was an adventurous and easygoing person, but did not want to give away her virginity too easily; I respected that and did not push the issue too hard.

Another important woman in my life was my sister Emily. She was twenty one and as far as looks go was a sexier version of me with C-cup breasts. Even her hair was identical, so from behind we could be, and were, easily mistaken.

We lived together in an apartment left to us by our parents, who had built a house in the suburbs.

Emily was a wonderful supportive person, but just like Dani sometimes had crazy ideas. Maybe because of that trait of her character her relationships with men never lasted too long or simply she had not yet found one who could see deeper into her. She had been together with her current boyfriend Max for around three months. He often visited us and I could hear their nocturnal activity, but they did not seem to have any plans of moving in together.

Things were moving along slowly and steadily, both at school and in my private life. It was two weeks before Halloween that Dani came out with a crazy idea. Although when I think of it from a perspective was it really that crazy or just a somewhat natural consequence of matters? She wanted me to dress up as a girl for the Halloween party that we were going to. I was hesitant, but then she told Emily about the idea and my sister loved it. I was outnumbered so any resistance was futile. So with two weeks ahead of us the preparations began. The girls did not want me to just put on a dress and lipstick, they wanted me to look and act like a sexy girl, from head to toe.

THE TRAINING

The preparations were thorough, beginning with the shaving of body hair which did not take as much time as one could fear. I had little body hair overall and in some of the areas that I did have it, like armpits, I shaved it regularly for hygiene reasons; I was left with just the crotch. The girls insisted on waxing my legs nevertheless, it was mildly painful with how little hair there was, although the change was noticeable to the touch. Dani caressed my legs in front of Emily and confirmed the results.

During the waxing I had been dressed in nothing but a pair of cotton panties that my sister had decided to lend me before we bought something specifically for me.

When my body was eventually smooth came the time for dressing. Having similar measurements as my sister came in really handy, we had all the necessary clothes at hand. It also turned out that Emily and Dani had nearly identical measurements as well; for me it meant that my clothing pool doubled, but the girls informed me that I would have to buy my own lingerie as soon as possible.

The first outfit that I put on was pretty basic - sheer pantyhose, mini skirt and a tight feminine shirt. Under the shirt I had a plain bra, we used pantyhose to fill the C sized cups.

I did not get to see myself until the girls finished my makeup and hair. When they finally placed a mirror in front of my face I could not recognize myself; there was a sexy girl looking back at me. I was vaguely aware that makeup could do wonders, but I had never imagined these wonders on myself. And, mind you, that was not a thick layer of plaster with my entire face redrawn. No, I was informed by the girls that they simply enhanced my natural beauty and brought it out into the prominence. That is not a compliment a man might want to hear from women, but at that point it made me glad, even proud to a certain point. My inner narcist was coming out of the closet; I had always enjoyed being pretty, so why should I not embrace being sexy?

Before I stood up from the chair Dani put on a pair of eight centimetre heels on my feet. She informed me that they were just a training pair and I would have to learn to walk in thirteen centimetre heels. At first I was slightly afraid of losing balance, but it soon turned out that walking in such heels was pretty easy. I had a feeling though that the additional five centimetres would make a significant difference. But I was not supposed to just walk, my ultimate goal was to look feminine and sexy and high heels were just one of many steps towards it.

The following two weeks were crazy but in a fun kind of way. United by a common goal Dani and Emily quickly became friends and I was their rookie girlfriend who needed guidance. We spent almost the entire time after school together (college in the case of Emily), we went shopping several times and I had to model numerous clothes in front of the girls. Just a few days ago I would have expected such an experience to be embarrassing, but it was pure fun. I spent nearly all of my free time in feminine clothes practising walking, mannerism and talking. My natural voice was not overly manly or low pitched, but there was nothing girly to it either; I did however have a minor acting talent and with enough practice and focus I could pull off a husky femme fatale like voice. I could not maintain it the entire time, but long enough to be passable.

There were two important details about my appearance that needed to be taken care of - breasts or rather the lack thereof and my genitals. Stuffing the bra with pantyhose might have sufficed initially but for the main play I needed something better. Breast pads were good for the "training" but for the party we bought a special pair that was supposed to be glued to my chest. They were incredibly realistic to the touch and the girls made fun of me when I played with my new boobs after having them glued for the first time; I joined the laughter.

As for the crotch the keyword is "tucking". I was amazed to realise that it was actually possible to make my penis "disappear" and it was not even uncomfortable. It required some effort, a bit of tape and well fitting panties (not a G-string). The only issue was going to the toilet, because the penis needed to be freed and later the whole tucking process had to be redone. But girls take their time in the toilet anyway, right?

Max was at first a bit jealous that Emily spent so much time with Dani and me, but my sister knew how to apeace him and soon he was a part time member of our crazy gang; two times he even joined us on our shopping trip. More than once he was a spectator during my lessons and I got a feeling that he admired my body as much as he did Emily's. But overall Max was a really nice and fun guy, we have not became friends already, but it was pretty clear that given time such a relationship was possible.

My female character also received a name; at first we though about the most straight choice - Olivia, but decided that it was too obvious. I was playing someone else, most importantly someone new, not just my old plain self in a skirt, so I needed a genuine name. After multiple suggestions I ended up being Sylvia. Dani came up with this name but I loved it the moment I heard it; I wanted to be Sylvia for the party.

One does not learn how to become a woman in a fortnight, no matter how competent the teachers are and how much enthusiasm is put into the process. But I managed to put in a decent act, my natural assets were not even the main factor; they did not influence my overall femininity as much as one would expect, but they did increase my attractiveness to men. As we paraded in short skirts, high heels and fancy pantyhose (Max obviously in male clothes) I noticed that I was getting as much attention as Dani and Emily. Being checked out by men was a novelty to me, but since it all happened while I was holding my girlfriend's hand I considered it all just a fun game.

I was fully confident that I could pull off the act of being a woman during the Halloween party. And speaking of the party we had picked costumes for ourselves - all four of us would be dressed as police officers. Max was a regular cop, but "we girls" were the naughty ones that sadly never patrol the streets. Our costumes consisted of a short tight blue dress, a black belt, fishnet pantyhose, high heeled sandals (on a thirteen centimetre heel as was promised) and a hat. To be honest, without that hat, some fake police insignia on the dress and a baton and cuffs attached to the belt it would have been just a sexy blue dress. But the details were suggestive enough for us to be called policewomen. Although there were other... details more suggestive, in a completely different way.

THE PARTY

The party itself took place at a rented hall and was more or less a close company enterprise, all those participating chipped in. The four of us took a taxi to get there, Max had a car but obviously we would all be drinking alcohol, so there would be no driver for the return trip.

There was not a main theme for the costumes, but everyone came dressed nevertheless. As we got inside we met my best friend Eric and his girlfriend Sarah, they were Pocahontas (naughty version) and John Smith. They recognized Emily and Dani, but needed several seconds to tell who I was, and that was more by deduction than recognition. They were shocked but amazed, both checked me out from head to toe and I even had to turn around so they could admire my "entire costume".

Sarah and Eric were a unique pair, Eric was a fun guy who flirted with all the girls, checked them out whenever he had a chance and made sexual jokes, but he never cheated on Sarah. She accepted his character with all its traits and was a rather entertaining person herself.

After the lengthy greeting we went to say hello to others and got some drinks. There were many superheros, some Disney princesses (all of them naughty), several characters from computer games, Conan, Red Sonja and others.

I knew most of the people at the party, but no-one was able to recognize me, some even failed to do so after a short chat; that made me proud of my acting skills. I would have never imagined that it could be so much fun. Of course everyone eventually learnt my true identity, but remained in the role of Sylvia and they called me by that name. The girls did not spare the compliments and even some of the guys continued to check me out even though they knew that I was a man.

The party went as such parties usually go - there was drinking, dancing, eating and talking. I can hold my liquor reasonably well, but I tried to limit it nevertheless, because I was afraid that being drunk would spoil my act. It did not spoil my fun in the least though; Dani and I were having a wonderful time together.

There were many sexy girls in revealing outfits, but we might have been the most popular pair, maybe because we were the only "lesbian" couple. We did not shy away from entertaining the guests, we danced sensually on the floor and even performed a steamy kiss in front of the audience. Dani reached her hand behind my back and grabbed my buttock, she then moved her palm downwards and forward as if pulling my leg. I immediately understood her intentions, raised my leg and wrapped it around her legs. We continued to make out until we run out of breath. Our audience rewarded us with a loud cheer.

The three girls and I might have been drinking lightly, but Max and Eric were not. Thankfully they had not gotten smashed, but quite quickly they got rather "relaxed". For Eric it mostly meant more aggressive flirting and erotic jokes being told in a louder voice. I received some attention from him as well, he complimented my looks a few times, pinched my ass twice and even slapped it when I was bending forward to reach something. By then I was already engulfed in my role and reacted in a flirty manner.

At one point when the entire company was drunk enough someone suggested a game - the boys would get blindfolded and would have to recognize their girlfriends just by touching their legs. Of course there would always be few other girls as decoys and as you might have already guessed I was to be one of them. It was Dani who came up with the idea of me participating which should not be a surprise either. That was a competition for the sake of the entertainment, so the prizes were not as important, but certain rules were made.

The boys could not touch the girls above the level of the skirt and they could not tickle or pinch them to force any sounds from them. If a guy guessed correctly the pair had to perform a steamy kiss not unlike the one Dani and I had. If he guessed incorrectly he would have to dance sensually with the girl he picked; there was no lack of volunteers. The rulemakers have missed an important detail though - girls wore different kinds of legwear and no-one said anything about taking it off. It should be easy to tell that legs in fishnets (like mine) did not belong to someone's girlfriend, if hers were bare. But maybe everyone was simply drunk enough not to care.

The first contestants were Zack and Carrie. She was a petite girl who trained gymnastics; she was dressed as Cammy White from Street Fighter, had sheer tan pantyhose with "camo" patterns and a green thong leotard; he was Ken.

We all got onto a long table, so the guys could stand while... well while touching our legs. Carrie was standing as the third in the row, with Emily being first and I second. Blindfolded Zack was led in front of my sister, he placed his palms on her calves for a second then moved them away. It seemed that he was sober enough to tell fishnet pantyhose from sheer ones. He stepped to the side and placed his palms on my calves, again it lasted only for a moment, but nevertheless it was a novelty for me. His touch was not overly erotic but it was not a manly slap on the back either. A tiny spark of something I could not fully comprehend yet lit up inside of me. Zack sidestepped again, touched Carrie's calves, moved his hands to her knees and announced that it was her.

Their "victory kiss" was not as hot as Dani's and mine, but they deserved a cheer from the audience nevertheless and received a genuine one.

Next to go were Conan and Sonia, they were called by those names throughout the entire night. She had bare legs and was standing as the last of five girls. I was there as well, number four, the only one in fishnets.

Conan was not as subtle as Zack, he placed his hands directly on the first girl's thighs. He moved his palms up and down a bit and even groped her thighs a little before shaking his head and proceeding to the next girl. He got equally touchy with all three before he reached me. I was pretty confident that Conan was not so drunk that he could not realise I was wearing fishnets, but he repeated the same routine as with the other girls, after all he was not aware that he was touching a guy; he caressed and groped my thighs for a while before proceeding to Sonia. The tiny spark inside of me was now burning lighter, I still was not sure what it meant, but I realised that I had enjoyed being touched like that.

Conan spent a lot more time at Sonia's legs, he groped and caressed them whole and from her expression I could tell she was enjoying it, even though he was doing it just for the show; eventually he recognized his girlfriend. Their kiss was fierce, they were both all over one another's bodies and seemed to be completely oblivious of the audience. They were both fit enough to look somewhat convincing as their characters and since their outfits did not cover much we got to see a lot of flesh on flesh action, all hot and sweaty. But the game was not over yet.

Next ones were Sarah and Eric or Pocahontas and John Smith. She also had bare legs and basically whole were on display since her version of the dress covered little below the buttocks.

I was once again among the decoys, pole position this time, Sarah was standing right next to me. Eric placed his palms on my ankles and began to slowly progress upward, but he was not just sliding them, he was thoroughly caressing every inch of my fishnet covered skin. As he reached my knees he spoke:

"I have doubts. I don't think this is my Pocahontas, but I better be meticulous so I won't end up with the wrong girl."

The audience reacted with a giggle, since it was obvious that Eric was just playing. That lengthy statement basically meant that he knew who I was NOT and wanted to make a show. But that was not just a random Conan, but my close friend. I was seriously wondering if he would do that if he knew that it was I, not Emily or Dani.

There was a lot more flesh on that part of my legs and Eric wanted to appreciate every spot, he was gentle, only occasionally softly squeezing my flesh. He reached the hem of my dress and drew a line with his finger on my thigh along the fabric. Instead of stopping he proceeded upwards hiking my dress slightly and then shoving his palms underneath, one went on the inside of my left thigh, the other to the back on my right buttock. He caresed them for a while, then finally removed his hands. I was breathing harder by then and I was sure my face was red. Eric spoke again: