The Training of a Transsexual

THE TRAINING OF A TRANSSEXUAL…PART I

                                                                       BY MISS PISS

       Don’t call me Steven. My name is Stella. I’ve known all my life that in this male Caucasian body, I was all woman. Luckily, I was born with features feminine enough to pull off my true sex. I look like my mother. She was the most attractive woman in my neighborhood, and, without a doubt, a MILF. She had bright blue eyes that are inviting but piercing at the same time. Bouncy blonde hair and a face that reminded you of Marilyn Monroe. Toned, killer legs that could make any man, young or old, go weak at the knees. Beautifully wide hips that gave way to a round, firm ass that was to die for. A petite but voluptuous body, absolutely fuckable from head to toe. A voice as soft as a bird and as sharp as a whip. If I had my mother’s lush and supple 36B breasts and a vagina, I too would have been the object of every horny boy’s desire in my neighborhood. I praise God and my mother for giving me her genes. I worship her for making me who I am. As for my father, he has always been out of the picture. He has never given us anything, not even an ounce of care for our lives and our well-being. The only thing my father gave me was his big and thick, 8-inch monster dick. He was a heartless, stubborn man for all I know. I don’t understand why my mother slept with him. All I know is that I was her sweet little accident. I never desired to know anything about my father, but I will never forget the one thing that my mother told me about him: after I was born, he gave one look at me and said, “This boy is gay.” He signed the birth certificate and then left the hospital, abandoning me and my mother ever since. Was my father right? Was I destined to be gay? Well, yes, the bastard was half-right. I’ve been attracted to boys since I was six years old. At sixteen I felt a slight attraction to girls. Whether or not I was sexually attracted to them or envied them more for the fact that they had breasts and a vagina, the thing I solely wanted more than anything, was a puzzle that I barely made an effort to solve. But if there was one thing that I was 100% sexually attracted to about women was their clothing. Oh how I love women’s clothing.

       My beautiful, sexy mother, she might have been the slut of the neighborhood, using young boys from ages 14-19 as her sex slaves and older men as her masters, but nothing about her wardrobe was trashy. She was a classy whore. Her wardrobe was mainly vintage, remarkably unique and intensely erotic. She had any vintage outfit you could think of: flapper dresses, polka dot halter dresses, taffeta dresses, corseted tulle dresses, floral silk dresses, pencil skirts, wiggle skirts, satin blouses, garters, corsets, and bustiers. Anything vintage 1940’s-1950’s style, you named it, she had it, and made it entirely fresh and completely her own for every season. I swear, my mother looked so stylish, independent, and smart in these outfits that the sight of her gave me my first hard-on. More than anything, she was a model of how I wanted to represent myself as a woman: a classy, sassy, sexy hot mama.

        I’ve tried on girls clothing privately since I was eight, but I started trying on my mother’s clothes, shoes, underwear, and makeup before I went to college. I was eighteen. I remember it well. I was fully naked in my mother’s bathroom while she was away doing her errands. I curled my long hair Marilyn Monroe-style, applied raspberry red lipstick on my soft Angelina-Jolie lips, glazed my eyelashes with mascara, patted a little bit of blush on my cheeks, slipped on an apple red garter belt to my hips and a pair of black fishnet stockings, wore a sheer white thong that was strong enough to hold my massive dick, slid my feet into red T-strap heels, and put on my favorite outfit of my mothers, a red polka dot halter skirt, stuffing the top with a decent padding of tissue paper as I could put in without making it look obvious. For the first time I saw myself as a fully dressed woman, a true woman, a smitten image of my mother. In my reflection, I was my mother. I stared in the mirror for what seemed like eternity, admiring myself, feeling so damn hot and sensual. Most of all, I felt empowered. I was finally a woman on the outside and a woman within. That moment was when I called myself Stella. The name came to me like a prayer, and like a god, I embraced it. No surprise, my mother caught me wearing her clothes that day. She had the biggest smile on her face and nearly cried when she first saw me. She hugged me tight and said how beautiful I looked, how beautiful her daughter looked. I was touched. It was no secret or surprise to her that I was a transsexual; she probably suspected that since the day I was born. It was the fact that I finally let it out in front of her in her own clothes, making her realize that her biggest mistake having me with a dirty bastard like my father turned out to be the best choice she has ever made in her life. My mother lent me some of her vintage clothes, bought me some new ones, and has called me Stella ever since.

       Now, I won’t bore you with anymore details about my transformation from Steven the boy to Stella the woman. I won’t reveal anything about my sexual fantasies and my sexual past, not yet at least. Nor will I delve heavily into the fact that my main sexual experiences were from watching my mother have rough, wild sex with her boy slaves or being whipped, pissed on, slapped, and fucked senseless by her masters. I must say though, I masturbated for hours while peeping on them through the cracked door. I know, it’s sick to imagine my mother having sex let alone watching her doing it, but it became a dirty habit for as long as I could remember. It was because of her that I became obsessed with watching others have sex more than the thought of me having sex.

       Anyways, back to the story that I’m going to tell. I guess you could say that the moment I became a proud, slightly shy, but confident woman in the adult world, starting when I went to college, had changed my life. Or at least that is what you would think. But no, in fact, it wasn’t a surprise to anyone that I was a very feminine boy in girl’s clothing, had changed my name, and worked two jobs solely for the pursuit of making enough money to eventually go through the process of gaining sex reassignment surgery. Since I’ve always felt that my gender transition was complete, I never called myself a t-girl and get frustrated when I’m called that name. Of course, that’s not the worst name that I’ve been called. I could write a whole book about my struggles, but I won’t go there. I will tell you straight forwardly about the basics. Nobody in my family except my mother truly accepted me. I got beaten, abused, misunderstood, and in general, people had always found me weird the instant they looked at me as if I came out of some bizarre fairytale. I was used to this long before I even became Stella, so it never overwhelmed me. My life has always been full of conflict and confusion about my sexual identity, even to this day. It became the most normal and predictable part of it. For a long time I was in my own comfort shell, believing that my life would always follow the same pattern, my mind concentrating on the same mission, and my own high-heeled wearing feet marching on the same long and winding road. Six years ago, it all changed. It’s hard to believe that it was six years ago when my life made quite an unexpected, unpredictable turn, and perhaps changed who I was forever.

       --------------------

       I was a fresh college graduate with a BA in Business and Communications. My dream was to own a vintage clothing store, but of course, most dreams don’t exactly come true, especially for people like me. I was lucky to find a job that came close to it. I was a secretary for Vintage Boutique, a pretty chic and highly expensive vintage clothing store. Everything they sold there resembled me and my mother’s wardrobe. I loved my job. I could carry my name loud and proud and be myself. My clients loved me for it, and I was paid well. I still lived with my mother, who was still as hot, irresistible, and charming as ever at 42. I didn’t think of ever leaving her nest anytime soon until my BFF Isabelle came over to the house one day during the summer.

       Let me tell you, Isabelle is the closest woman that I could imagine myself making love to. She was a striking young woman. Isabelle was 5’5,” short coal black hair that reached down to her shoulders, sharp piercing green eyes, and such a cute, petite body. Her breasts were no more than a 32A, but it perfectly proportioned with her tiny frame. She had two piercings, one on her tongue and one on her bellybutton. She also flaunted a tattoo of a butterfly on the back of her neck and an angelic fairy on the small of her back. By looking at her, you could sense that those green eyes and her witty sense of humor suggested that she was a woman of raw, exciting sex. She always dressed spunky and goth-like, but she had the bubbliest personality. Ah, and her face, high cheekbones, skin that had a natural glow as if she bathed it in moonlight, and skinny lips that were as sensual and beautiful as a full-lipped woman. And her voice, oh that voice, it had a nice southern twang to it that made you feel warm and at home in her personality. Most of all, Isabelle was such a genuine, sweet girl. Guys always pursued her; she was definitely a big flirt with them. There was never a time when she didn’t have a boyfriend or didn’t frequently get laid. She was a tiger, a tidal wave, a sweet storm, a passionate lover, quite the feisty fucker. But at the end of the day, Isabelle was my goddess, my angel, my one and only true friend that accepted me for who I was and has always admired me for simply being Stella. I admired her as well. I admired her courage. She had lost her mother at age eleven. The poor lovely woman died in a car crash and was pregnant with a baby boy who was going to be named Dylan. She had such a close connection with her mother and had always wanted a brother, so the blow was double the excruciating pain. Her father had become a single parent ever since her death, raising Isabelle and her five sisters on his own. Despite the tragedy, Isabelle didn’t become a druggy or tried to commit suicide during her teenage years. She might have had some depression and was sometimes a little rebel, but she remained humble and embraced the memory of her mother and unborn brother, her family, and her friendships, especially ours. I can’t imagine what life would have been like if we had never known each other. We knew each other since high school, went to the same university, pursued the same degree, and graduated together side by side. After graduation, for some unforeseen reason, we lost contact for two years.

       When she came over to my house that summer day, I was absolutely thrilled. Not seeing her for two fucking years felt like forever; seeing her again after two years felt like we were only apart for five minutes. She hadn’t changed a bit, but there were a few things that were remarkably different. Her breasts augmented to the size of my mothers, a 36B, all natural. They looked juicy and produced a nice bounce when she walked. She stuck out her tongue at me playfully before she gave me a welcoming hug. She not only had one tongue piercing, but now flaunted four round, silver studs in each hole. Through her sea blue tank top I instantly noticed her perky, firm nipples. At first I thought either it was slightly chilly outside or if she had been playing with them before she arrived. To my surprise, she had a nipple piercing in each breast. My eyes were in awe. She giggled at me, knowing that despite how shy I was I couldn’t help but get a glimpse at her new sparkling beauties.

       After we embraced one another, we skipped into my room, laughing and cuddling. We lied down on my bed, drank some lemonade, listened to ABBA, and had a few tickle fights and poking wars. Yes, we were still kids at heart, the old times were back again, and our old memories were never left behind.

       “So Stella baby, how’s life going for you?” she asked once we settled down.

       “Life is wonderful,” I replied, my voice by then having a perfect ring and tone of femininity. “Still living here with mother obviously, but I couldn’t feel any happier.”

       She made that sweet, “I absolutely adore you” smile of hers that always made me feel complete. And those intense, bright green eyes, they plunged into my inner soul, hypnotizing me into her inner beauty.

       “You look so beautiful Stella,” she said warmly. “I missed you so much.”

       I blushed. I knew that I looked beautiful, but Isabelle made me feel the real thing.

       “You look quite gorgeous yourself, you horny, sexy thing. What man corrupted you into getting more piercings?” I chuckled, playfully teasing her left nipple through her shirt.

       “Hehe, want to see them?”

       “Of course!”

       She lifted up her shirt and showed me her piercings. Hard, rosy red nipples with simple, sparkling silver studs, oh how exotic and aesthetically pleasing they looked.

       “I love them!”

       “That’s not all…” she grinned.

       She lifted up her black skirt, revealing her lovely crotch to me. She wore sheer and seamless pink panties. Through them I could see a silver plated clit ring protruding against the fabric.

       “Oh god,” I gasped.

       “I knew you’d like it,” she winked.

       “I’m jealous…” I smirked. “Soo…who corrupted you into getting these?”

       “My girlfriend.”

       I was shocked at that statement. Of all the years I’ve known her, she has never told me that she was into girls, let alone even hinted that she was a bisexual. Isabelle told me everything, including every detail about her sex life. I was completely speechless.

       “What?” she giggled. “Cat got your tongue?”

       “Oh no! I’m just…well…I didn’t know that you’re into girls. Not that it’s a big deal, I’m just surprised. You always told me that you could never imagine yourself being sexual with a girl.”

       “Well,” she blushed. “After we graduated, I wanted to explore my sexuality deeper, expand my horizons, not only with men but with women as well. I had a threesome once with this cute redhead and my boyfriend during that time, a few months after we graduated. I can say that not only are threesomes triple the fun, but I love the smell, taste, and physique of a woman.”

       I grinned; my cock twitched. I always loved hearing Isabelle talk about her sexual adventures. She knew this. She was definitely not shy to entertain that fetish of mine. Even if what she did wasn’t my kind of sex, it always made me hot and horny imagining the wild, sexual beast in her devouring her prey. Secretly, my ultimate fantasy was to watch her have sex. But since that hadn’t happened, hearing about her sexcapades came close to the real thing. 

       “Tell me how you and your girlfriend met,” I beamed excitedly. “And tell me everything about the first time you two had sex.”

       “I almost forgot how horny of a bitch you are,” she chuckled. “Alright, I will tell you the story of how I met my girlfriend, Mia.”