How I Became Vanessa Ch. 01byvanessa_brown©
I was a man before becoming Vanessa, and my name was Mike. I was heterosexual and I was going out with my first "serious" girl friend for two years when all this started. I was still living with my mother who had been divorced for a decade before getting remarried. Her new husband moved to our place with a beautiful daughter named Elena who was only 18. I was a handsome 22 year old blond boy, quite feminine in my features and certainly very shy with girls because of this very reason. My girlfriend, July, was actually my first one, and she did the first step towards me. I was not really in love with her although she was an attractive brunette, and her gothic style was not really my cup of tea, but I thought I could not attract anybody else sexier. So I stayed two years with her, developing strange fantasies. As she was not as feminine as I would have liked her to be, I started to buy her sexy lingerie.
But July rarely put it on: _"Come on Mike, that's not my style! I don't like this girly stuff, if it turns you on that much, why don't you put it on yourself?"
And so I did and we made love like two lesbians. Later, we repeated the same kink adding a dildo that July pushed in my ass while she was sucking me. But it was nearly the end of our relationship as I grew a little bit more confident and cheated on her with other girls to reassure myself that I still was heterosexual.
Obviously I wasn't. Men didn't arouse me but the mere idea of getting cross dressed and dominated by some anonymous cocks drove me wild. July dumped me and I stayed alone for a long time. I continued to dress up by myself, using make up, shaving my entire body, wearing the sluttiest outfits (fishnet body stockings, latex legging, thigh highs...) and the sexiest wigs. I even bought a big black dildo very realistic to practice on my ass or in my mouth, dreaming that a magic spell would make it alive, spurting cum in my bowels and in my throat.
By that time, I was 24 and my step sister Elena was 20. I was more and more attracted by her: she was a beautiful blonde with big tits and long legs and the face of an angel. I was watching her under the shower through a hole in the wall and I had no idea that she did exactly the same while I was myself in the shower. Nothing happened for a while as the situation was too taboo to dare making a step toward each other. Elena told me later that she had discovered my secret while watching me in the bathroom getting cross dressed. She had been shocked at first but became quickly aroused by the sexy view of my convincingly slutty appearance. She masturbated watching me while I was fucking myself with the dildo under the shower. Then, one day, I was watching her getting undressed in the bathroom, she was so gorgeous: she slowly put a black corset with garter belt, black seamed stockings, high heels, a black choker necklace and started to rub a dildo against her clitoris.
She sucked it, moaning like a whore and then slid it in her ass, whispering my name: _"Oh...mmmm, Mike, I would like so much to be fucked by you!"
On the other side of the wall, I could not help but ejaculating, licking my own cum as if possessed. I was on the edge of knocking at the bathroom door to fuck her when my mother came home. Nothing happened this day, but the bomb was set to explode very soon...
I was very saddened by the way my relationship with July ended and I regretted her a lot. I hadn't seen her for 6 months when I saw her in the street waiting for somebody at a bus stop. She was gorgeous, she did not dress as a Goth anymore, she wore a tight white top, a grey pleaded miniskirt, showing the top of her thigh highs and a pair of tight black knee boots: exactly what I liked and what she had always refuse to wear when she was going out with me. Her hair was longer, jaw length, and still gothic black. I was consumed with desire and walked in her direction when the bus arrived and her new boyfriend came out: it was John, a guy she knew before me and that she had dated for a couple of weeks but refused to sleep with him because his cock was supposedly too big...
I followed them back to their place, a small apartment downtown and I had no trouble entering the building and watching them through the staircase: In front of their door, John started to take off her skirt, revealing her beautiful ass and the sexy g-string she was wearing. They kissed and she kneeled down, unzipping his pants and freeing a 9 inch cock which must have been at least 2, 5 inch in diameter! She could barely take it in her mouth! She was groaning of pleasure when he exploded what seemed like buckets of cum in her mouth. I could not believe it: she had always refused me to swallow my cum and now she was doing it with another guy who had the biggest cock I had ever seen! They entered their apartment, leaving their door open in the rush. I sneaked in admiring John's cock already hard again, now fucking July's ass (another delight she had always refused me!) I was in shock, dead with jealousy but with whom? Was I jealous of her or jealous of him? I was so confused...July raised her head and saw me; she shouted with anger and ran after me in the stairs of the building, not even taking the time to put something on.
She caught me before the ground floor, took me by the wrist and shouted at me: _"What the fuck are you doing here? Are you spying on me you pathetic little sissy?"
I fumbled a few words...her face was dripping with cum...She was so gorgeous... I kissed her, plunging my tongue in her mouth, tasting John's semen. She was outraged and slapped me twice.
_"You fucking pervert! I should have guessed when you asked me to fuck your ass with my dildo, you're just a fag! With your pathetic little dick, how could I've wasted two years of my life with you!"
She calmed down and then she looked at me with the most perverted and twisted gaze I ever saw on her face: _"If you don't want me to reveal everything to your mother, you'll have to do what I want."
I nodded in agreement.
_"You're going to put up some of your kinky stuff and come back here tonight. I want you to taste a real cock and to swallow some cum directly from the stem."
_"July, I can't do that, it's just a fantasy, I'll never dare to do it for real, besides men don't really arouse me, it's just that..."
_"Shut up! You'll learn how to love men; I can assure you of that! See you tonight or else, your mum is gonna discover what kind of twisted little sissy she has raised."
I went back home and cried a little, although the situation aroused me and I thought I could have sex with her again during the evening. I was glad to be blackmailed; it was the only thing I needed to make the final step to achieve my fantasy. Besides, with an ex-girl friend as a teacher, it couldn't be better.