Date: Thu, 26 Oct 2017 18:51:48 +0000 (UTC) From: Ronald Shearing Subject: Starting with Simone Part 4 TG Starting with Simone - Part 4 Nifty / transgender / teen Legal stuff. This story is fiction and is 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, please close this page now. Please note, I am always happy to receive feedback at the email address in the header. If you like my story or want to apply (hopefully constructive) criticism or make suggestions for improving later installments, email me at Ronald DOT Shearing AT yahoo DOT com. If you've read parts 1 through 3 you'll already know these tales include more than a passing reference to smoking fetishism. But just in case, if this is a problem for you, please don't read any further. Lastly, as always in my preambles, I mention that if you enjoy accessing erotic literature on nifty, please do donate to nifty at http://donate.nifty.org/donate.html. Without nifty, we would not have such a great place to share such exciting stories. Having left Simone and Carla asleep upstairs in the Blount home, I'd got back to my own home mid-morning Saturday in quite a nervous state. The night before, not only had I had my first experiences of being blown by two girls simultaneously, not only had my first experience of handling the cunt end of a DP, shit, I then realized, my first time actually shafting a REAL girl, I was also experiencing a should-have-been predictable down side of under-age drinking, my first hangover. I'd woken up on the Blount's couch to find a short note beside me. It reminded me I had a lot of thinking to do. It read simply, "4 to 4:30 this afternoon by Sbarro at the mall food court. If I don't see you I know why." There was also noted down a link to a file sharing website and a temporary login and password. With an instruction, "Log in after 2pm. File store you want will be called SCR_18June". The note was signed off simply with an "S". That could have been Simone, my beautiful teen trans companion. Or it could have been Simon, my nerdy classmate. You see I'd fallen big time for what I'd originally thought was Simon's sexy cousin Simone, only to find that the absolute fuck doll I was lusting after was a very expertly transformed feminine version of nerdy Simon. I'd gone in eyes open, well, balls deep actually. And I could not get Simone out of my head. I think I might even have been in love. I must have been I thought, otherwise how would I have taken such absolute delight in sucking Simone's she-cock. I wasn't even gay, I kept telling myself. At the end of the prior night's sexual acrobatics, Simone had told me that if I genuinely wanted to carry on with the affair, I'd have to bring Simon into the equation. I wasn't sure how we were going to do this, but that was what the 4 o'clock sit down was going to clear up. Assuming I went. With my head throbbing, I was still 100% unsure what I was going to do. When I got home, luckily mom had already left for her Saturday morning spin class, so after downing what felt like a quart of orange juice, I slowly climbed upstairs to my bed, setting the alarm on my cell for 2pm. This would give me time to get ready for my mall trip, assuming I plucked up the courage to go. And it would also give me time to check out the files Simone was uploading to the file share site. I had a pretty good idea of what was going to be there, and I was more than curious to look at the photos we'd taken the night before. At 2pm my phone buzzed annoyingly, and I probably would have turned off the alarm and kept on sleeping but for my urgent need to take a shit. As I evacuated my bowels I noticed I had a horrible taste in my mouth and I laughed inwardly as I speculated whether the taste was the after effect of the pizza or whether it was the cunt juice Simone's girlfriend Carla had violently squirted copious amounts of into my mouth. Once I'd washed, and cleaned my teeth, that was it, I was up now. I had a quick scan downstairs. Mom still out, no doubt shopping. I remembered the note. Website. Pictures. I realized I was still unsure about the meet with Simon at 4pm. Which was now a little more than an hour and three quarters away. I sat down at the desktop PC in my room, navigated to the URL Simone had specified, then nervously entered the temp login and password. After changing my temporary password to something "memorable" at the prompt, I was in. Very basic HTML site, a lot of ads at the top of the screen, then one single blue underlined directory, "SCR_18June". I clicked on it and in a second there popped up a long blue list of filenames, all prefixed with a random set of letters and numbers, all with a jpg extension. I opened the first file, then clicked my way through. The first five were of Carla, "making love to the camera", as Simone had snapped her. In all the pictures, Carla was smoking her Marlboro hard, and it really did strike then me how much smoking turned me on. There was one close-up shot of Carla pulling her cunt lips apart with her fingers, the lit cigarette clearly in view, that really got me going. The Carla smoking shots had got my droopy cock perked up slightly. The next half dozen pictures made my heart skip a beat. They showed Simone's beautiful face up close to my own hard cock, the last three showing her gripping my rod tightly, Marlboro between her fingers trailing a jet of smoke upwards. In my favorite picture of this subset, the last one, Simone was smiling at the camera as she held my dick. The lit cigarette was poised an inch or two to the side of Simone's smiling lips. This one looked more natural than the staged "pout and look sexy" poses of the others. It struck me again just how stunningly beautiful Simone was. I started to feel slightly emotional at the next set. Various shots of Simone and me kissing each other like two lovers without a care in the world. In half of the pictures Simone clearly held her cigarette in her hand, either rested on my shoulder, or between the fingers of the hand squeezing my face close to hers. In these shots, the upper part of the sheer black body suit I'd chosen for Simone contrasted wonderfully with the light skin exposed on her neck, shoulders and upper arm. Clicking on, there followed a set of real girl Carla and me making out, which I skipped through quickly, until I got the close-up shot of my cock, the tip ever so slightly jammed in the PVC garter belt Carla had been wearing. The thought suddenly crossed my mind I had a nice-looking cock, I'd seen plenty as an avid teen watcher of online porno. The shots of me sucking Carla's tits stiffened my dick a little more, a reaction to how pleasured Carla's face looked in the pictures as I chewed on her pierced nipples. I thought to myself how, despite the fact Carla was not exactly "supermodel" shape, she was one very sensual woman. Woman, not girl, she was clearly a real grown up woman. Though I still felt she was nowhere near as beautiful as Simone. My breath stopped suddenly, as I opened the next pic. In perfect focus, me sucking Simone's beautiful she-cock. In each shot that followed I had my eyes closed and I looked as if I was in ecstasy. The horniest showed the whole head of Simone's cock on the tip of my lips. Carla had taken a lot of shots of my oral action. In some, Simone's "Brazilian" pubic strip and clean-shaven balls were clear, along with the garter belt and straps. Another favorite of this set; Carla must have had backed away to the coffee table, so only the dark hair on the back of my head was visible between Simone's stocking legs. Simone's gorgeous face was clearly in view, her eyes tightly shut, her jaw clamped in a look of sheer pleasure. Without a second thought I hit the download button. It occurred to me the folders might only be temporary so I flipped the back button and downloaded all the pictures of Simone and myself, plus my cock close-up and the best tit sucking shot with Carla. Scrolling forward, I reached the cream-pie photos of Carla's gaping cunt and visibly distended asshole. I smiled as I realized that my cum from Carla's cunt hole had dribbled downwards and formed a gooey union of Simone's and my seed where Simone's cum had slowly oozed out of Carla's butthole. I was pretty much all the way hard now. The last few pictures were the "selfies" Simone had shot as she drained my softening dick of any last remnants of my cum. All I could see was the contentment in Simone's eyes in the couple of shots her eyes were open. Butterflies in my stomach. I made up my mind. I wasn't going to jerk off. I was going to the mall. I clicked download on the last set of pictures, then logged out of the file sharing site. I headed for the shower. I arrived at the mall around 3:20pm. It was a fairly quick walk from home if I took the short-cut under the highway. When I entered the mall I initially made a move for the Comic Book and Baseball Card store near the Food Court in the basement level. I looked around inside for a few minutes. I remembered there was a Sports bar just before the communal food hall seating area which had a TV facing outwards on what the Sports bar classed as a "Terrace". I walked over and caught the end of a wild Cubs walk off win as their batter doubled in 2 runners with 1 out in the bottom of the 9th. On the screen, all I could now see was a jumping mass of celebrating white uniforms at home plate. I still felt nervous, so I again ducked into the Comic Book store. I thumbed through a few issues of The Punisher. I'd seen a pirate of the recent Punisher movie and it was my favorite comic book at the time. I looked at my watch, then double checked on my cellphone. 4:01pm. The moment of truth. I headed out of the Comic Book store, and walked tentatively back towards the Food Court and the corner where Sbarro was located. The area wasn't too busy. Tired and hungry shoppers were easily identifiable by their multitude of shopping bags. I noticed a slight figure at a table on their own facing away from me. Shortish brown hair, gray hooded sweatshirt. I circled round, and as I thought, it was Simon. I approached the table and sat down directly opposite Simon. "Hi", I said, nervously. "Hi", Simon replied. I smiled. That seemed to put Simon at ease a little. "I had to come, ...", I started to say "Did you get the pictures? ... ", Simon said at the same time. We both went silent. "Sorry," I said. "Look, I saw the pictures. That's not why I'm here though. I'm 16 and I'm mixed up. I feel strongly for you Simone ..." "I can't be Simone 24/7 Ronnie!", Simone firmly but quietly interrupted. "Not yet, anyway". I touched Simon's hand for a second, then pulled back as I realized other people might be looking. "Where do we go from here?" I asked. "I really want to know" "So do I", Simon responded, then repeated, "So do I'. Simon continued, "Let's get a coffee, maybe it will clear my head." We got up from our seats and walked over to a coffee counter. Simon ordered a Skinny Latte, I got an Americano. I insisted on paying. We picked our cups up and headed to a table in as quiet a corner we could find, at the side furthest away from Sbarro and the other food outlets. The whole Food Hall area was starting to fill up with late afternoon shoppers. Simon took a sip of his Latte, then started talking. "I've kind of known since I was about 12 I wanted to live like a girl. You probably don't remember but I used to wear my hair long. Mom loved it, in fact she wouldn't let me get it cut for about 18 months. Even when I cried at night and told her jerks like you were calling me a sissy at school". I felt compelled to interrupt, "No way Simon. Never once did I call you a sissy". "No, you just fucking ignored me, even though you lived across the street". My mood dropped slightly. I thought back 4 years. I'd been massively into my Little League baseball team at the time, and I'd had a circle of friends exclusively related to my sporting passion. I felt I hadn't deliberately ignored Simon, but it was like we had nothing in common back then, and our only social interactions had either been at neighborly gatherings, like 4TH July when my mom and dad would throw a firework cook out, or the occasional classmate's birthday party. I'd remembered having the hots for Wendy, Simon's sister, but that, I had to admit, was that. Simon, I inwardly acknowledged, I guess I had always thought of Simon as the quiet guy who had the hot sister. Simon took another sip of his Latte and continued. "I started to feel you and all the other boys our age only had eyes for Wendy. I felt like I was invisible. I was jealous. I was angry. I thought if I'd been a girl I would have been getting attention like Wendy. Mom was always telling me what a pretty boy I was. So, I secretly started wearing Wendy's clothes. I started by taking her dirty clothes out of the laundry basket. Mom didn't notice. Wendy certainly didn't, that bitch never ever did anything to help around the house. I'd put them on dirty, then I'd just "be" in the clothes for a few hours. Then I'd take them off and return them to the laundry basket when I was done". I was silent, I just looked across my coffee at Simon as he went on. "When I was 13 I had my first orgasm. It was when I was wearing a soiled pair of Wendy's panties and one of her trainer bras. I'd stolen the bra from a pile of Wendy's old stuff that was going to the dump. Wendy's tits had already outgrown it. I was thinking of a boy I really liked. I rubbed my hands over the front of the panties until I shot inside them. It took me a few seconds to understand what had happened". Simon finished the last of his Latte. "When Wendy started smoking with her friends at school, I saw how sexy she looked, so, I started sneaking cigarettes from mom. She hadn't switched to menthols at that time. I found the act of smoking so sensual. It got so I couldn't have a smoke without jerking off. It even got so for a few months I couldn't jerk off without smoking a cigarette. Mom luckily didn't cotton on. She'd already accepted that Wendy was a smoker and let Wendy smoke in the house, it wasn't too hard to cover my tracks." Simon was playing with his coffee cup nervously. "Last summer was when things started to develop sexually. As I said, I'd started stashing clothes Wendy was throwing out, and I'd been gradually building up a make-up collection. Mom had bought me a digital camera for my birthday. I knew mom had a big lingerie collection in her walk in. After dad had left, mom had been quickly back in the saddle, I'd gotten used to the occasional "friend" visiting. I knew she had special outfits for her "gentleman friends". She didn't really hide it. Mom had joined some online dating sites, and some adult chatrooms. She wasn't good with computers. One time she even asked me to get rid of some pop ups covering her screen, and it was easy for me to see she had been hooking up with men online. She had two open chats and I could clearly see what was being discussed. A few days later I logged onto the PC, and decided to explore. I went through the browser history and accessed mom's dating profile on a couple of the websites she'd been using. She was so fucking useless with the internet, she'd kept herself logged in. Her photo galleries left little to the imagination, and it also showed me there were lots of sexy things I could borrow from her wardrobe upstairs." Simon paused. I was enthralled, but I was alert enough to ask Simon to go on. "One Friday evening mom and Wendy went out to a movie. I took the decision to get myself dolled up and do a self-photo shoot. I made myself up as good as I could at the time. I was probably a mess, but I guess no worse than some of the trailer trash sluts I've seen since on bar crawls with Carla. My hair was still long and looked quite feminine in a kind of "bad hair day" way. I was squeezed into a black age 14 pair of Wendy's panties I'd stolen and kept, and one of Wendy's bras. It was a black sports bra that fitted my chest tightly, it bumped a little and kind of hid the fact I was tit-less. I took some shots on timer on my camera. They were OK. Then I remembered that Wendy's college laptop had a webcam. I logged into that and took some photos using the built-in camera. I started browsing. I knew mom's credit card details by heart, so I spontaneously decided to sign up to a contact site. I thought what the fuck, let's use a site mom uses. I chose the local area contact site, handling the 5 boroughs and surrounding areas. I must have secretly known I wanted to meet someone. But my plans that evening were for some chat, and maybe some mutual masturbation." Another pause from Simon as he gathered his thoughts. The stuff I was hearing, I now had Simone firmly in my mind, not Simon. Simone. "I did this all on Wendy's laptop. It took me about 20 minutes all-in to get set up. I chose the profile name SimoneSexy, it's still live. I snapped a face pic with my lips pouting like a teen whore to use as my profile pic. When I got into the site, I decided to enter 2 chatrooms, "Meet tonight" and "Cam action". Before long my incoming chat request alert icon was flashing and beeping like crazy. I thought to myself, not even that slut Wendy would get hit on like I was being hit on". Simon looked over at the No Smoking sign. "I could do with a smoke. Fuck, forget it". Simon swirled the index finger of his left hand on the chrome top of the table we were sat at. "Anyway, I got hit on by one guy on both rooms. Username "Leven50". I accepted the cam request. I can see him. He can see me. "Leven50" was an older guy, he was wearing shades and a Jets cap, otherwise he was naked. We got chatting. Next thing, I lit a Marlboro, just out of habit, he hadn't asked me to or anything. Right away, "Leven50" is grunting. He stands up and all that's on camera now is his fist frantically pounding his fat cock. While he's doing this, he's telling me he loves whores who smoke. This gets me hard, I put the cigarette in my mouth, I free my cock from Wendy's tight panties and keeping it low and out of sight of the cam I start jerking like crazy. Well. Next thing I know Mom and Wendy walk in, I tense automatically and shoot a long thick load onto the keyboard of Wendy's laptop. As the laptop tilts forward on the desk all I hear (and mom and Wendy hear it too) is "Leven50" shouting "COCK! You've got a COCK! Come over here right now and fuck my ass!" Just before the laptop fell off the desk, I used my free hand, the one not round my still twitching cock, and I skillfully stopped it falling to the floor. I flipped the laptop lid shut in one movement. That's when mom and Wendy start to freak out". As Simon stopped talking, I took a deep intake of breath. Then I realize that listening to Simone's story (yes, Simone's story) has got me VERY hard. "Talk about shitting in the soup", Simon sighed. "Wendy went absolutely ballistic, Mom was kind of quiet at first. Wendy started to scream at me. She was calling me a dirty faggot pervert who only wanted to fuck her life up because I was jealous she was a girl and popular, and I was just little sissy fag who copied everything she did. Thing was, she was mostly correct. She told mom I smoked. I didn't say anything back, which annoyed Wendy even more. Wendy moved to hit me, and that's when mom stepped in, telling Wendy to calm the fuck down and to go out onto the back porch for a cigarette and a time-out. Wendy did what mom asked. Mom turned to me, told me to go to the kitchen and clean up Wendy's computer, then announced a family meeting in the living room in 15 minutes. Mom told me firmly to take Wendy's shit off and clean myself up before I came back into the living room. She then walked off lighting a Newport as she headed out to join Wendy to smoke on the porch". Simon paused again. Thoughtfully. It looked like he was re-living that night. "Let's get another coffee", I suggested, "then we can carry on talking". Simon smiled nervously and we headed back to the coffee counter. After getting more coffee, we sat back down at our quiet corner table. I was the first to speak. "Family meeting. This is when they told you that you needed therapy?' "This was the FIRST time they told me I needed therapy, actually". Simon carried on speaking. "It seemed Wendy had calmed down a little. She just sat staring at me through clenched teeth. Mom gave Wendy a cigarette, lit it, then lit one of her own. I was surprised when she handed it to me. Mom then lit another cigarette for herself. Mom told us we were all grown-ups and needed to act like it from now on. Mom was pretty good in the circumstances, I realize now. She told me I was wrong to steal Wendy's clothes. She then gave me 10 minutes of bullshit about me being a confused young man, coming to terms with changes in my body, needing to socialize more, get a girlfriend. It finished with her ordering me to get my hair cut in the morning. In fact, she drove me to the barber's herself the next day." Simon again paused for a few seconds, gathering his thoughts. "That wasn't the end of it. Over the next week, I convinced mom I was just experimenting, going through a phase, yadda yadda. The fact I'd just dumbly agreed to getting my hair cut helped. After that night I got caught, I worked hard to keep my tendency well hidden. I never dressed when Wendy was home from college, even if she went out. Only if Mom had said she was staying out all night, did I contemplate dressing. And only then when the urge got so strong I had to give in. I was lucky in the times I chose. Never once did Mom come home unexpectedly. I'd even take chances dressing during the day if I knew mom was going to an exercise class, or a lady's lunch, or yoga. Like the day you caught me." My heart skipped a beat. "The clothes you wear now, that's where Carla comes in?", I ventured. "Carla!", Simon laughed. "Now there's a story. No, not all my clothes come from Carla. A lot do. With Wendy away at college I think mom secretly turns a blind eye. I'm pretty sure she knows I still dress. But Carla, well, meeting Carla was really mom's idea." What the fuck. Simon almost laughed at the puzzled expression on my face. "Mom had been pestering me for months about getting a girlfriend, a date", Simon continued. "Eventually she said one night after dinner that she had a friend coming round. About 8pm, mom then suddenly remembers some urgent appointment, and said she needed to drive to pick something up from a friend's place. Right away I'm thinking, bullshit. Mom told me to let her friend in. 10 minutes later the doorbell goes. In walks Carla. Before we've even got into the living room she's French kissing me, grabbing my balls and cock through my jeans. Carla stops briefly just to order me to take her to my room. We get up there, Carla takes her coat off, and she's rocking a slut look in nothing but a red garter belt and red stockings. Before I know it Carla's nearly ripped my jeans off and is sucking my dick. Carla knew something was not right as I couldn't get fully hard, so she broke off and lit us both a Marlboro." Simon pauses again and mentions once more how he needs a cigarette. But he carries on. "We're lying there smoking. Carla lets me know that mom arranged for her to come over, and "make a man of me". She explained mom and her had had some fun with a couple of guys a few weeks before. They'd hooked up online, arranged a meet, and after the 4-way, mom had told Carla the story of my cross dressing and showed Carla the online profile I'd made. Carla thought I looked cute, and was delighted when mom suggested that she "fuck me straight". So here I was, me and Carla in my bed. Carla then told me to relax, we had all night as she knew mom would be having fun with the 2 guys from a few weeks ago and staying over. Part of the "arrangement". It was then that she smiled mischievously and suggested she put some make-up on me. I was stunned, but I couldn't agree fast enough. I looked in the mirror when Carla was done and even with my short hair I thought I looked so hot. It was like a professional make-up artist had done my face. I was fully hard now. Noticing this, Carla pushed me back onto the bed on my back, mounted me, stuffed my rigid cock into her cunt hole, and took my virginity. As we lay sharing a Marlboro in the aftermath of our coupling, Carla promised to be my special friend. She said she'd help me dress right, but that it would be our secret. It worked well until mom realized a couple of months ago that Carla and me didn't exactly have a normal boy-girl gig going on like she thought." Simon stopped talking. "Sorry Ronnie, I need to smoke. It's not exactly classy but give me 5 minutes in the men's room". Simon stepped quickly towards the men's room. I saw the door swing closed behind him. I thought for about 30 seconds, then made my mind up. I headed towards the men's room. When I opened the door it was clear Simon wasn't the only person who knew the men's room was a secret smoking spot, as the smell of stale tobacco was clear in the air. An older man brushed passed me on the way out as I walked in. Nobody pissing at the urinals. Three stalls, two with doors ajar, the third furthest from the door was shut. As I approached I could clearly smell the tobacco smoke coming out of a freshly lit Marlboro. Glancing around one last time I tapped on the door and quietly said Simon's name. "It's me, it's Ronnie". A few seconds later Simon opened the door and I slipped in quietly as Simon sat back on the lowered toilet seat. I put the lock back in the door. Simon put the Marlboro to his lips and slowly inhaled never breaking eye contact. We said nothing. I unzipped my pants, and my achingly erect cock slipped out, my balls still jammed inside, caught in my boxers. Simon leaned forward and I closed my eyes. This is Simone I told myself, this is Simone. We both stayed totally silent. With my eyes closed all I could see in my mind's eye was Simone sucking my cock. Naturally, Simon was as expert at sucking dick as Simone was. Simon/Simone rhythmically gave me head like an expert, pausing only once to take a final drag on the Marlboro before crushing it out on the metallic lid of the toilet tissue holder. Seconds later, and with a stifled groan escaping my mouth that sounded more like a squeak, my cum flooded into Simon/Simone's mouth. The orgasm hit me all the way down the inside of my thighs. I involuntarily tensed, digging my toes into the soles of my trainers as my intense orgasm gradually subsided. When I opened my eyes again, Simon/Simone had swallowed all my cum. Making sure we heard no noise from outside our cubicle, we quickly and quietly left the men's room. "Let's head home" said Simon. "we can talk some more on the way". We headed for the path that went under the highway. Simon/Simone continued to open his/her heart to me. "Ronnie, when I'm 18 I'm getting my tits done. Carla's got a surgeon acquaintance. Fuck buddy I guess. We've already discussed it. I'm going to live as a girl as soon as I can." "Simone, really. As a girl?", I started. "The whole sex-change thing?", I asked nervously. "No Ronnie, the cock is staying. I'm into fucking as much as I like getting fucked. One day maybe you'll let me make love to you. I wouldn't fuck you Ronnie, but I dream of making love to you". I glanced away nervously, I still wasn't sure about taking Simone's cock up my ass. "Anyway", Simon continued, "In a little under two years, I'll really be Simone. No more Simon. This is the life I want to live. My future, living with no fear as Simone". Without thinking, I blurted out, "Simone, I want to be with you forever". While my sexual experiences the last two weeks probably eclipsed what some men get in a lifetime, I was still really an innocent lovelorn teen at heart. "Let's see how it goes, Ronnie. But I do like you a lot. I've had crush on you since I was about 12" Simon suddenly confessed. I stopped in amazement, then blushed. "Your first ...". "Yes", Simone said, breaking me off mid-sentence, "It was you I was thinking of when I came for the first time in my life". We'd reached the start of the roadway to our houses. Simon turned sideways to me. "Monday, mom's going to Aunt Michelle's in Connecticut. She'll be leaving around 11am, after the traffic has calmed down. I'll text when I'm ready". We said a quick goodbye, then split directions and headed to our respective houses. I felt sad we were parting, even though Monday was only a couple of days away. I couldn't deny it at all anymore. I had fallen for Simone hard. To be continued