3 comments/ 104715 views/ 12 favorites How I Became Vanessa Ch. 01 By: vanessa_brown PART I: 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. How I Became Vanessa Ch. 02 Hello dear readers, I strongly encourage you to read the first chapter of this story to fully grasp the sudden changes which affected my life. I dressed up with a very tight black long sleeves top and a black mini-skirt. I added a choker necklace like the one Elena used to wear. I chose a pair of black fence net thigh highs to show my beautiful legs and stiletto high heels. I also chose to wear my shorter blonde wig (jaw-length) and some heavy make up. I didn't know I wasn't alone. I was starting to prepare my ass with some lubricant and to squeeze my big black dildo in when Elena came out of her room, walking sexily towards me, wearing the same outfit that I saw her wearing in the bathroom and also a pair of long black gloves that she had borrowed from my secret drawer. Before I had any time to protest or to say anything, she kneeled down and sucked my cock bursting with desire. Feeling her lips on my prick was overwhelmingly good: it was the exquisite materialization of my secret dream for my step sister. How many times did I dream about this delicious instant while masturbating or while I was peeping at her under the shower? And now, it was for real! There was some sort of lustful agreement in the gazes we exchanged. No words were spoken. Her blowjob was mesmerizing. She took charge of the dildo in my ass, provoking very quickly a blast of my cum on her face and in her hot mouth. She slowly stood up and swapped the sperm in my mouth. I couldn't believe it: I had been just blown by my beautiful step sister before becoming a sex slave of my ex girl friend! We kissed passionately and we discussed a lot about our mutual attraction and also about the shower teasing when my cock hardened again and I fucked her sensually on her bed. She asked me to shove my cock into her ass as she wanted absolutely to know what I felt before. I was surprised to discover that she was nowhere a virgin... While I was sliding my thin dick in her anus, she told me that she had a boyfriend who was bisexual and she wanted to introduce him to me. I agreed. Then I told her about my appointment with July: it excited her. She asked me to tell her everything about it afterwards: she would wait for me in my bed. How convenient that my mother was away with her husband for a couple of weeks! I went out, walking fast in the streets as boys were cat calling me at every corner. I don't think most of them realized I was a man and it was really exciting to be so desirable. I arrived at July's place and knocked at her door. _"Hi sissy, wow, you look so damn slutty! You're so beautiful; John is going to like that!" I entered and saw John on the couch, wearing nothing else but a boxer. July was dressed in a fishnet body stocking and thigh high boots. She served us a couple of drinks. I felt the gaze of John laying on me insistently and I saw the huge bulge forming between his legs. July said: _"Time to start Vanessa, it's going to be your new name now, the slutty Vanessa, cock craver and total whore...kneel down and blow him!" I kneeled down, my face at the level of John's crotch and released the huge cock from his boxer which bumped heavily on my forehead. I opened slowly my mouth and licked the tip of the prick and the entire shaft. Then I took it in my mouth. It was so huge! But I was used to such big sizes as my dildo was pretty big too. It felt so much better than a dildo: this warmth and this odor of sex were intoxicating. I didn't want to show her I was enjoying it, partly because I was ashamed of it and also because I wanted her to think that her revenge was working and that she was being successful in humiliating me. Maybe she would leave me alone after that: I was rather afraid to become her sex slave forever and suffer the constant blackmailing power she would have upon me. Unfortunately, I couldn't help moaning softly with pleasure. July laughed and said: _"Don't tell me I'm forcing you to do it, you obviously enjoy every minute of it!" She pushed me and sucked John. She ordered me to be on all four and to get prepared for my first anal. I took away my skirt and my g-string. John was behind me and with the help of July's saliva; he entered my ass in a couple of thrust. I was screaming of intense pleasure when July got in 69 under me and sucked my cock while spreading my ass cheeks to allow John to go deeper. His pounding as well as her sucking started to accelerate. He had no mercy for my ass and she used me like a sex doll. Still in 69, I exploded in her mouth as I was licking her juices and then John withdrew from my ass, came in front of me and shot his cum in my mouth. I swallowed most of it and took the rest on the face. July came to me and swapped my own cum in my mouth, we played with all the semen, kissing each other perversely for a while with this huge quantity of cum. I came back home, promising her to be back. To be continued... How I Became Vanessa Ch. 03 Hello dear readers, I strongly encourage you to read the previous two chapters of this story to fully grasp the sudden changes which affected my life. * At home, Elena was waiting for me but she wasn't alone, her boyfriend was there too. He was a tall black guy named Jeff. I told them all the things that happened at July's, blushing as Jeff was watching me with desire. Elena hadn't changed her sexy outfit and her beautiful face leaned towards Jeff's crotch uncovering his 10 inch cock which was even thicker than John's. She started to suck it hungrily, encouraging me to join her which I did without hesitation. I couldn't believe how fast everything was happening and how easily I was metamorphosing in a total slut. I guess it was my true nature. We had very kinky sex this evening. Then I confessed to them that the last step for me would be to achieve my most secret fantasy: to perform a gang bang. Jeff had a lot of friends who would be willing to do it for me. I proposed Elena to invite July and John as well. She thought it was a great idea. The next Saturday evening, I was dressed up with a black latex outfit: long gloves, thigh highs, mini skirt and top, with platform high heels, my usual choker and my black hair wig of medium length. I wore a white gloss and white eye shade to contrast with all this black rubber and I looked really like a gorgeous porn star. To make it really fun, Elena and July decided to dress exactly like me. We looked like three bitches, two black haired and one blonde, ready for ultimate sex. John had joined Jeff and his friends (3 of them) and we went out in a swinging club. All the men were obviously staring at us when Jeff let the entire room know about my desire for a gang bang, asking anybody who wanted to join to feel free to do so. Then, we went in the next room which was ready for extreme sex: stools, hand cuffs, ropes, everything was here to hold us captives in the case we finally chickened out. Elena and July started to lick each other, watching me getting all the attention from a dozen of guys. All these cocks, so many of them black, almost all of them quite big, made me salivating. I was overwhelmed with lust and sucked them all franticly, winning some cheers from all of them. I was moaning like a whore, I was finally fully Vanessa, the total slut. I drank their cum, I spread it on my face. I offered my ass to all of them, sometimes getting a double sodomy. By then, Elena and July had joined the orgy and swallowed as much as me. We frequently turned to each other, licking each other's face, swapping cum. It drove the men totally insane! This night I decided to become Vanessa forever and stay with my two slutty friends for more kinky stuff, no matter the consequences. I would not dress up as a man anymore, I would take hormones to grow boobs and let my hair reach a feminine length. I decided to tell it to everybody, including my mum and nobody would ever make me change my mind. I was thinking about all of that when the last blasts covered our faces and when I started licking the semen drooling from Elena's butt with July's help. It was a total scandal when I told my mother everything about my new aspirations. Obviously, I never said anything about my step sister Elena; that would have to remain a secret. After a while, my mother accepted the fact that I would never become a real man: seeing me dressed up as a slut everyday certainly helped her to understand the situation. She finally made peace with me and even started to give me some suggestions. My outfits were way too sluty for her taste but she taught me how to perfect my make up and to buy some clothes in stores. People didn't even notice I was a man, they probably thought my mother was going shopping at the mall with her two daughters (Elena came always with us). I'm so turned on when I think about all the times Elena and I went to the Mall's restrooms to have a quick fuck, licking each other while my waiting mother didn't even suspect it...Most of the time, I came quickly in Elena's mouth and she swapped it in mine and kissed me passionately afterwards. Once, my mother thought Elena had some crusted sugar on the side of her lips from the ice cream she just ate, not suspecting that she had just finished to blow me in the restroom. It excited me tremendously then and it still does now. I had taken hormones for a couple of months and now I had nice medium boobs that I preferred to keep at a reasonable size. My body hair was much slower to grow back, I had plucked correctly my eye brows (although they were naturally thin and I still wanted to keep a certain thickness to them: I've always thought girls with kind of thick eyebrows looked sluttier). My hair grew down to jaw length, I didn't need any wig anymore and at that time, I had dyed it in a Venetian blonde color. My hips widened a little and so did my ass (which was way too skinny before). I looked really cute. When I went out with Elena and her black boyfriend Jeff, every male was envying him for the two bisexual sluts who accompanied him. I was 24 and Elena turned 20. For a couple of years, we had this secret relationship and we dated many men, organizing some orgies or some gang bangs very frequently. We still went out with my ex girl friend July and her future husband John (read the previous chapters for more details about our relationship). I moved out of my mother's apartment and started to rent one closer to John and July's. My mother thought that my job's salary as a secretary was enough to pay for it, and it was quite true, but the extra I did as an escort in a transgender club helped me to live a more comfortable life. Not knowing anything about my sex life, my mother agreed to let Elena be my roommate: she moved with me and so did her boyfriend Jeff. At last, it allowed us to have threesomes on a daily basis. One Saturday morning, I decided to include in my weekly routine a little bit of biking. I was a little bit concerned about the outfit I would have to wear because I never wanted to get an operation and to get rid of my cock: it was way too good to cum in Elena's mouth and to fuck her while Jeff was fucking me, and even if I loved being a woman and being treated as such, I still enjoyed sex as a man, or more exactly as a woman with a man's organ. I was the perfect dyke in a way. So I was a little embarrassed about wearing some spandex short, but after putting a black one on my body, rearranging my cock in it, I realized that the bulge wasn't really noticeable. I found the matching top very complimenting for my chest. Then, one morning, dressed up in this beautifully tight outfit, I went biking by the lake. My hair was held by a black band which allowed the sportsmen to admire my feminine angel face. I found the saddle of the bike very uncomfortable, I liked to feel it between my ass cheeks but after a while, my ass was a little sore. Two black guys were biking just behind me for half an hour, certainly staring at my butt when I decided to take a break. They stopped next to me and asked me if everything was ok. I smiled at them invitingly, pushing my bike on the side and disappearing in the bushes. They followed me; I found quickly a quiet place, turned towards them, kneeled down and caressed their bulges. They laughed at me, not believing the kind of slut they had just found: -You love big black cocks honey, don't you? You can't help but begging us for some dark meat... -You have no idea how much I love it and how I need it, but I don't think I'll be able to give you anything else than a blowjob, my ass is hurting from the bike... -You're not the one to decide about that, honey! They slipped out of their spandex shorts, freeing two gigantic cocks of 10 and 12 inches and at least 3 inches of diameter. Their balls were heavy and full of cum, I couldn't resist and throw myself on them, devouring their pricks, covering them with saliva and moaning like a whore. They took away my top and caressed my boobs and my face with their big wet black dicks. - Shit you're a real fucking whore; you sure know how to blow! Show us your nice ass. I executed myself: one of them continued to penetrate my mouth while the other took off my black spandex short. He was going to spread my g-string on the side of my cheeks to penetrate my ass when he discovered my hanging little cock. -I can't believe it man! This girl is a fucking sissy! -What are you talking about? -She's a transsexual! They looked at me angrily; I begged them not to hurt me -You're gonna pay for this trick, there is no way your ass is going to escape from the most painful fuck you'll ever have. -Well, I don't think me being a woman would have changed anything anyway... -Shut up whore! He slapped me and took me by the neck, shoving his cock deep in my throat. The other one used is saliva as a lubricant and entered my ass violently. I screamed as I couldn't bare the intense pain but the fucking became more and more pleasurable and I moved my ass backwards to meet his cock at each thrust, spreading my ass cheeks to take him deeper. The one in my mouth spurted his cum deep in my throat and I swallowed avidly what seemed like a gallon of sperm while the other came balls deep in my ass. I couldn't believe my ass was able to take his 12 inches all the way and his warm ejaculation in my womb drove me wild. We rested for a while and then, I started to rub their dicks once again and it didn't take long to get them as hard as before. They couldn't believe I was begging for more. One of them took a pill from his back pack and forced me to swallow it. It was a kind of drug that helped me to relax my ass muscles and that made me even hornier. Then, I understood they both wanted to fuck my ass at the same time, I wanted to escape from this madness but the drug made me drowsy and unable to defend myself, I just had enough power to reach for a tube of lubricant in my own back pack and literally empty it in and on my crack. They made me seat on one of them, guiding his dick in my ass while the other started to rub his prick next to it and push it slowly inside me at the same time. My ass spread up to 5 or 6 inches to accept these two giants: I couldn't scream, I was just moaning feebly under the effect of the powerful drug and looking back at this crazy experience, I can't believe I didn't pass out, but I'm sure it was the tube of lubricant that literally saved my ass! They fucked my butt quicker and quicker, mercilessly, calling me with all the dirtiest names, licking my boobs, pulling my hair as if I was the cheapest whore ever. Finally, they took their big cocks out and came abundantly on my face, covering it with their warm semen. I barely opened my mouth and slid my tongue out to receive some of the offering. It didn't stop ejaculating and I swallowed again a lot of it, licking also my lips and gathering the cum that had dripped on my boobs with my finger and sucking it clean afterwards. I put my clothes back on, they left and I passed out. A cop woke me up an hour later. He asked me what happened but I kept my mouth shut as I didn't particularly regret it. He drove me back home. In the car, he proposed me to take one of his tissue to clean the cum from my face. I realized that he was staring at my legs and also my boobs; I smiled and told him to stop the car. He did it, as if bewitched by my smile, and I leaned towards his crotch, unzipped his pants, popped his dick out of his boxer and sucked it with hunger. I could easily deepthroat his 7 inches cock and made him cum quickly in my mouth while he was gently caressing my neck. He was mesmerized. He asked me for my phone number and I gave it to him before he finally dropped me home. I decided, this Saturday biking experience had definitely to become a routine!