Date: Mon, 6 Nov 2017 12:03:54 +0000 (UTC) From: Ronald Shearing Subject: Starting with Simone Part 8 TG Starting with Simone - Part 8 Nifty / transgender / teen Legal stuff. This story is fiction and is intended for mature readers only. If it is not legal to read this story in your jurisdiction, or if you are not over the age of 18, or I just realized in some places, 21, please close this page now. If you haven't done already, please read Parts 1 through 7. For those of you who have been travelling along the storyline with me, my warmest thanks for sticking with me this far. If you enjoy accessing erotic literature on nifty, please donate to nifty at http://donate.nifty.org/donate.html. Nifty is run for us by volunteer(s) whose dedication is admirable and should be supported by all our community. I am always delighted to receive feedback. Feel free to email me at Ronald DOT Shearing AT yahoo DOT com. I look back now at the Summer of 2004 with very fond memories. I see that it ultimately affected my life in a good way, a very good way, but I still have difficulty understanding and coming to terms with a lot of the emotional turmoil I was going through at that time in my life. I'd started the summer straight as straight could be, a normal 16-year-old priapic boy with a girlfriend I felt sure I was going to fuck sooner rather than later. By the end of that summer I had changed. I had dumped my girlfriend without us doing the act. There had been a truly unexpected intense burst of explosive sexual activity. And I met my "true love". My sexual orientation became mixed. Certainly, regular straight people would not call my sexual orientation, either then or now, "normal". But I realized then that my deepest desires involved transvestites, transsexuals. Chicks with dicks if I'm being open about it. It was a sexual awakening, in the true sense of the word. It was actually who I was, who I AM, sexually. Simone just unlocked the door. Well, smashed the door open with a great big ax. My "true love" had been Simone, who'd turned out to be the trans alter-ego of my nerdy class mate, Simon. I look back now and find it hard to imagine Simon at all, I can't even picture him. Simone lingered in my dreams for years afterwards. It is Simone. Only Simone. I am still massively physically attracted to females, or should I say feminine looking people. Shemales. Transsexuals. Transgendered. Transvestites. Even convincing cross dressers. Gay sex, I guess what people would define as regular gay sex, doesn't hold much attraction to me. After that summer with Simone, I dabbled, heck I guess one liaison that summer was technically "regular" gay sex. But without the feminine side being part of it in any way, it just didn't turn me on. I tried but it simply didn't work for me. Before I got married, I took special joy in meeting with what seemed to be attractive women with a little surprise when we got into the bedroom. To the extent that as I reached my early 20s I tuned out of the hetero scene completely and focused on bars and clubs that were part of a certain "other" scene, where I knew I could get what I needed. The internet was my savior. If I'd had to seek it all out myself, I really wouldn't have known where to start. I'd probably have had to move to Brazil or someplace. Thailand. Fuck knows. Back in the summer of 2004 I also discovered just how sexual I found the act of smoking to be. Feminine smoking of course. I'm not a smoker myself. Some pot at college and an occasional after dinner cigar aside. From time to time I'll find myself carrying a cigar so I can lounge in smoking areas of bars and clubs surreptitiously getting hard as I watch a sexy female enjoying a cigarette. Perfection is watching a sexy trannie or shemale smoking, nothing beats that in my eyes. Especially as a prelude to a fuck. Although since I've married, I've calmed down a lot. My wife does turn me on when she smokes, and she's known that for quite a long time and indulges me, especially if we're staying in a hotel that has smoking rooms. On trips, we always book smoking rooms. The first time we met she was smoking. And we'd fucked soon after. I didn't have to introduce that into our relationship, it was there from the start. Back to 2004. Simone and I had shared an intense experience together that summer. As we acted out our romance in private, for me secrecy was key. I'd have died if any of my school mates had thought I was a "fag". We didn't know it at the time but the pressures of our secret affair would eventually lead to it flaring out. For Simone and I, our love was a flame so intense it couldn't burn forever. It wouldn't even last the year. There was no one thing that caused us to split up. It was a combination of things over a period of months. There was an incident where one night I stayed out all night with Simone at Carla's place. I'd been ambiguous in what I told mom about my plans before going out. Eventually getting me on my cell, Mom woke me out of a deep post-coital sleep in Simone's arms at 4am and really lost the place, telling me if I wasn't home in 20 minutes she was calling the cops. I had to get Carla to risk a DUI to get me home. Simone was upset, the sex that night had been great, but Simone really wanted me to sleep all night with her. Like we really lived together as a couple. The row with mom when I got home lasted an hour-and-a-half. Mom was so stressed she was chain smoking Marlboro lights. I hadn't seen mom smoke in years, she'd quit when I was about 10. She accused me of being a sexual pervert. I look back now and I think she'd just used that phrase as in her eyes, normal 16-year-old-boys who constantly thought of pussy and stayed out late and fucked girls were perverts. Maybe it was just the first phrase that came into her head. But the comment totally spooked me. Did she know about Simone? And I thought for a few seconds that Janice, Mrs. Blount, had told mom about the fuck a few weeks prior. And maybe shown her compromising pictures of Simone and me. Me sucking Simone's cock. I was terrified mom would find out the truth. Since dad had left I'd deliberately made an effort to make sure I didn't give mom any problems. Now I could see myself letting her down in the most spectacular fashion. Going back to school was also difficult. Some of my friends made fun of my new "friendship" with Simon. It wasn't like I could totally ignore Simon at school. My other friends on the soccer team, I'd switched to soccer when it became apparent that a no-glove slap-hitter with a 220 average wasn't going to get much playing time on the baseball team, routinely referred to Simon as a "fag" and I guess I wasn't bold or mature enough to stick up for him. It really twisted my feelings inside, and it also made me do a lot of internal soul-searching. Was I a "fag"? What if people found out? Or was I just a pussy who should stick up for the person he loved but was too scared to react? It was a lot of pressure for a teenager to handle, and my grades suffered, so much so mom was called in for a meeting with the vice- principal before the Holiday season. Simone, I think, could sense a that things were not right. She tried to persuade me to go out with her and Carla often. I'd decline. As a girl, Simone could pass for 21, and Carla had got Simone a fake ID from an ex- boyfriend who worked at the DMV in Hauppauge. Me? I was clearly a 16-year- old boy. True, I'd started to sprout some fluffy brown facial hair, but no way was anybody going to serve me in a bar. The one time I gave in, I was laughed out of the bar we were visiting, and it hurt my feelings badly to be humiliated not only in front of Simone, but also in front of Carla, who had become a deep friend to me. I was embarrassed. The end came I think as a combination of two situations. The first situation was called "Marie". Marie Bettencourt had lived in our town as a young girl, I remembered her vaguely from middle school. Around age 14 her dad, who worked for an International Investment Bank, had been posted for 2 years to Paris, France. Her dad was now back working in the City, and the family had moved back into their home about 3 streets over from mine. Marie had two younger sisters. Marie had a sophisticated air about her, mysterious even, like a foreign film star. It came out later her grand mom was actually French, I hadn't known that at the time. Marie had blossomed when she was away, had become very pretty. Medium length dark shiny hair, a beautiful pert nose and thin but perfectly shaped lips. A very toned body, with tits that drew many admiring glances and comments from the boys at school. No doubt about it she was hot. She also smoked these weirdly scented foreign cigarettes, I found out later she'd get them at this specialist place near Ronkonkoma. I can still remember the aroma when she smoked. She had come back with a slight French touch to her accent, and I found her totally exotic. I also thought she was out of my league. Way out of my league. Much to my surprise, one day Marie asked me if I could help her on a Math problem and she in return would help me with my French. Could I go round hers after school. When I got there I'd hardly got in the door before she started kissing me. Nothing sexual developed that afternoon, it was more of an "age appropriate" first-date make out on the couch, a LOT of kissing. I enjoyed it and we started dating. I agonized over what to tell Simone and I found myself taking the easy option of saying nothing. Within 2 weeks it was clear at school that Marie and I were an item and Simone was greatly upset. I hated myself for doing this to Simone. On the next occasion Simone and I met at Carla's, Simone had clearly been drinking (a three-quarters empty bottle of Rose wine was on the table) and it looked like she'd smoked two packs of Marlboros, you could cut the smoky air in Carla's living room with a knife. We had our first proper row, our first lovers' tiff. We quickly made up and Simone gave herself to me and I fucked her as intensely as I had ever done, and after I'd come I gently sucked Simone to completion taking all of Simone's come in my mouth and swallowing it. I had felt so bad I had even considered letting Simone fuck me, have her take my virginity, but with her dick as it was, not fully active after the wine, the idea quickly left my head, and I ended up glad I hadn't made the offer. A week or two later, Marie and I had sex for the first time when her parents were out at some work event (Marie's mom also worked at the same bank as her dad). In the aftermath of our lovemaking I lay next to Marie as she smoked and could think only of Simone. The funny thing I realize now, is that in appearance, Marie closely resembled "natural Simone", when Simone dressed as a normal girl. But unlike Simone, Marie had an ample rounded pair of breasts. Then again Marie didn't have a beautiful thin cock. Thinking deeply about it, I felt that Simone was actually prettier than Marie. But I was totally confused. Like I was two people in one body. Situation two was called "Janice". I was spinning the Marie/Simone relationships like a circus act spins plates on sticks, realizing that it would not take much for all my plates to fall crashing to the ground, smashing into small pieces I could never put together again. One night around 7:30pm I got a text. It's from Simone. "Emergency. Mom out. Come over in 30 minutes" I'm thinking what to reply, I hadn't spent any time at all in the Blount's house since Simon's mom, Janice, had fucked me. Before I can reply, another buzz, "if you don't come over we are done". I quickly replied, "see you in 29 minutes :-)" I let myself into the Blounts the back-porch way. I was surprised to see Simone sitting on the couch, not Simon. Casually dressed, neutrally dressed, light gray sweat shirt and tight jeans. Like a girl who'd just got herself ready for a trip to the mall. Minimal make up on, only obvious around Simone's eyes, and the gorgeous messy hair look I had grown to love. Simone firmly crushed out her Marlboro on the ashtray on the table in front of her, but didn't get up. It looked like she might have been crying, it was hard to tell as Simone's eye makeup looked so well done. I decided she had been crying. "Ronnie, I'm going to ask you a question. Give me a truthful answer. I've always thought we'd stay true. I'd stay true to you. You'd stay true to me. I get the Marie thing. I don't like it but I can live with it." Simone lit another Marlboro. I'm not getting where this is leading. I'm puzzled, really, I am not at all sure at what is coming. "OK, but Simone, ..." I'm jarred by the sudden loudness of Simone's scream, "QUIEEETTT!". I fall silent immediately. "Ronnie, did you fuck my mom?" My mouth fell open. "Don't even fucking answer", and with a quick movement off of the couch, Simone stormed upstairs. I started to follow upstairs, but it hit me. What the fuck can I actually say? Simone's mom had taken advantage of me, much as John Pierre, with Simone's mom's help, had taken advantage of Simone. But to me, my germinating 16-year-old emotional intelligence could not process that. To me, boys, or men, took advantage of girls. Not the other way round. Mrs. Blount seemed to have given me a choice, after getting me hard, she'd laid back seductively, it seemed to me that she'd given me the choice of jumping on top of her and fucking her, or not. That's what my confused 16-year-old mind thought. I reflexively blamed myself, and in my shame, I felt I couldn't go to Simone's room to explain. I walked out of the Blount house for the last time. As I walked across back to my house all I could hear in my head was Simone's voice saying, "stay true". I continued my relationship with Marie until we both headed for college. Different colleges. Plus, Marie took a long trip to Europe, so we agreed amicably to split. I still thought of Simone. I secretly craved for Simone's cock. Mrs. Blount found herself a new long-term boyfriend about a year after Simone and I broke up. "Mr. Jones", I knew him as, still don't know his first name. He and Janice once came over to our house for dinner with mom, and I was terrified when I walked in on them at the table. It was almost a relief when I heard Mrs. Blount was remarrying and that her and Simon were moving with Mr. Jones to Westchester. Not a million miles away, but far enough away that I could feel my secret was safe. I managed to have one last conversation with Simon. I caught him one day on the back porch of his house shortly before the move. I tried to explain my feelings for Simone. Simon calmly told me that he'd be living as Simone as soon as he could. Carla was going to lend him the cash he needed for the boob job on his 18th Birthday. Carla's surgeon friend was doing them a special deal. I winced a little as I considered how the discount might have been negotiated. Simone told me she was going to stay true to herself. She hoped I would stay true to myself, at least in time come to accept myself for what I was. I yearned so much inside for Simone, but I just couldn't pluck up the courage to ask for one final meeting with "Simone". A few weeks later the Blounts moved. Later, in college I'd date mainly girls, but inside I really wanted the love of a trans person. I had a spectacular unexpected liaison with a dorm mate who turned out to be a secret dresser. I guess accidentally leaving my laptop open with shemale porn links active on it didn't turn out as bad as I'd imagined. After our first coming together, we'd occasionally arrange clandestine dates, but it ended in a sudden manner when we were caught by a cop in an embarrassing situation in my car. Luckily the cop was prepared to let us off with a warning. But what my trannie girlfriend had to do to satisfy the cop that a warning was the correct punishment on this occasion spooked her, pretty much for good, and we never had a liaison again. It didn't help any that the cop had made me watch and jerk off while he satisfied himself in my girlfriend's ass. I'd go occasionally to gay bars, only once getting lucky in a trans sense. I'd usually attract some attention when I was out, at that time I still had the "boyish good looks" I was often told I had. When a guy approached me, 99 times out of a hundred my explanations of only being into trannies would result in a quick end to the conversation, but one night I got lucky when the guy hitting on me happily told me he dressed and had a full wardrobe at home. He showed me some pictures on his cell phone. It was clearly him, and I went back to his place and fucked and sucked the night away. We met a few times after that, once even managing a threesome with some older CD he'd gotten in touch with online. The CD was the obvious type, blonde wig, black rubber and way too much makeup, but she chain-smoked Marlboros and had a decent figure for a 45-year-old. She also liked having two cocks in her ass at the same time. I guess I could tell a few tales of my college years. Maybe another time. After college I got a job at a brokers in the City, decent salary, and good job prospects if I was prepared to work hard. My sexual liaisons were mainly arranged online during this time, but I did become a regular at a special club night for "Those who dress and those who admire", every Thursday night at a rooftop bar on East 48th. I had a major setback around this time when mom was diagnosed with breast cancer, and passed away not 6 months later. As an only child, I got the inheritance. I remember seeing my estranged dad at the funeral, but I didn't even want to talk to him. We exchanged sympathetic platitudes and I haven't seen him since. I sold the old house on Long Island, which help set me up with an apartment in the upper 50s that I would no way have been able to afford otherwise. I progressed well at my job. Nobody there knew my secret. Like I said before, I had my Thursday night routine at my favorite club. One Thursday, as Winter 2014 started to show its face in earnest, proved to be a pivotal moment in my life. The club was normally a regular rooftop joint, dimly lit boutique chic, but every Thursday a members' club dedicated to the transgendered and their admirers hired it out. Admirers, like me, paid 2 grand a year membership. "Ladies" were able to get a free membership if approved by a fellow member. Ladies could also take a paid membership for half the admirer rate. I'd found out about the club online one evening browsing the web for some action, and signed up that night. For a year or so I'd been a regular, and had got to know some of the admirers around my age, and had also managed around a dozen liaisons with "lady" members. The club was reached only by elevator. Security was subtle but effective. The club itself was split into two main areas, one more of a bar scene with tables and booths, the other a small dancefloor for those who liked to dance. There was an outside square balcony smoking area with an outlook towards the east river. I'd keep an eye on the smoking area normally. And I'd always make sure I brought a cigar with me, just in case. Music wise, it was "modern lounge" mainly, nothing too crazy. Occasionally a regular would plug his or her sounds in to the system, it was that kind of place, relaxed and welcoming. I felt really comfortable there. I'd put the average age of the admirers around 30, 35, some obviously rich guys older than that. I was one of the younger regulars. There was no written dress code, but the clientele had self-regulated on a "dress to impress" dress code. I'd usually wear a casual suit with an open neck shirt, or if I'd come straight from the office, about 7 blocks down on Madison, I'd roll up in my work clothes, sometimes keeping my necktie on, sometimes not. I was batting 500 necktie on or necktie off, so I was never quite sure whether to keep it on or not. There were occasionally natural women there, I guessed wives or girlfriends of regulars, but the place attracted what I considered to be the best of the transgendered scene in NYC. There was even one time a very well known Italian trans pornstar showed up. I thought about hitting on her, but she seemed to be the guest of a couple of the older guys so I decided not to try. Some of the older guys did not seem to have regular day jobs, if you know what I mean. They even provided the security, so I knew better than to fuck with them or their "guests". Most of the girls who frequented the club were major league hot, but that Thursday night I saw someone who took my breath away. As she walked towards the section of the bar where I was standing nursing a Scotch (Janice had been right, Single Malts are divine) I, along with every guy in the vicinity stared as this blonde goddess came closer. Dressed simply in a tight black and gold patterned dress which accentuated her extra-large enhanced boobs, with a classic platinum blonde hairstyle, I was stunned when she walked straight towards me and smiled. "Wanna buy me a drink?" she said as she looked me straight in the eye. "Sure, what would you like?" I tried to calmly reply. There were occasions when professional shemales showed up at the club. And there had been times when I gladly paid, when it was subtly inserted into conversations that the girl I was talking to was "working" that night. I'd hand over the 200 dollars (that seemed to be the going rate) when we got back to mine, or if I'd take a cab to their place. I was wondering now if this girl was on duty, or if I'd just lucked out. "Gin tonic", the girl replied, in a voice deep enough to know I wasn't being hit on by a natural girl. I ordered her drink, plus a Glenlivet 18 refill for myself. Fiddling around in her purse, she motioned to a free two-seat booth to my left. "Let's sit over there". I admired her succulent ass as she slowly stepped in the direction of the booth. As I sat down, I was able to fully take in the stunning beauty of what I hoped was going to be that night's fuck. My first thoughts were that someone who looks this good is definitely a hooker. Firstly, a little on myself. At that time in my life, late twenties, I was only a couple of pounds over my ideal weight. But I was self-conscious that I looked slightly older than I was, mainly due to the fact I'd inherited from mom an early tendency to gray hair. When people were being nice to me, they told me I looked distinguished. I hadn't gotten to the stage I was so uncomfortable I'd gone as far as applying hair dye. So, I wondered if the girl in front of me thought I was one of the older millionaire types. I was never ever the truly self-confident type. Except when I was drunk, and as I was only on my second Glenlivet, that was not the case so far that night. As we crossed the floor to the free booth, pretty much every admirer in the bar had stopped what they were doing and glanced over. This girl was special. We sat down. I stared at the girl across the table from me now. She had golden brown skin, a very sultry look. I wasn't quite able to pin the look. Hispanic, maybe mixed race, difficult to tell and the bleached blonde hair didn't help making identification any easier. "I'm Ronald", I said as I took a sip of my Scotch. "I don't think we've met". Sipping on her gin through a pink straw which almost matched her bright pink lipstick, the stunning girl opposite me replied. "Trixie" I smiled. "Well, I might be Trixie tonight, or I might be Ellie". I must have looked confused. "If I'm working, like with those older guys", Trixie, or was it Ellie? continued, "I'm Trixie. If I'm having fun it's Ellie". Trixie removed a golden colored pack of cigarettes from her purse, along with what looked like an expensive lighter. I could see the cigarette brand, Davidoff Gold. "I joined the club a couple of months ago. I've seen you here a couple of times", Trixie/Ellie continued, "Never had an opportunity to talk. Tonight, I thought I'd make the effort to get to know you". I thought I'd have remembered seeing a girl this hot, but I wasn't too bothered. She was sitting across from me now, and I was pretty sure we'd be fucking later on, it was just a case of whether my wallet would be 200 bucks lighter in the morning. "OK, Ronald, tonight with you, I'm Ellie". I smiled a thank you to Ellie, who smiled back. I signaled to a waitress for 2 more drinks. Ellie's iPhone buzzed. Ellie looked at the screen. "Ooops. Said I'd meet a friend here, she's not been here before. She's arrived, having a smoke out on the balcony, I'll be back in five minutes. Keep my seat warm". Ellie picked up her cigarettes and lighter and headed in the direction of the smoking area. I couldn't take my eyes off her swaying ass tightly wrapped in the black and gold mini-dress. Wow, I thought to myself, I've landed on my feet tonight. While Ellie was out smoking the two fresh drinks arrived at the table. A few minutes later, I could see Ellie approaching, at her side there was another VERY attractive dark-haired girl. Even from a distance I could see that Ellie's friend had a fantastic figure. Ellie and her friend approached the table. I stood up to give my place to Ellie's friend. Then time stood still. "Simone", I gasped. "Hi Ronnie", Simone replied with a smile, "Long time no see". To be continued.