Date: Wed, 20 Apr 2016 20:45:29 +0100 From: Iain Bell Subject: Scott Finds A Sissy Chapter One SCOTT FINDS A SISSY - Chapter One Please do remember that NIFTY is a free website for us writers and you the reader, it needs your help in keeping it free. Please use the donate button and give. Thank you. Please feel free to comment on this story as I love to hear feedback of all kinds as I find it invaluable in future writing. My tale starts eve of my 16th birthday. Both my parents were killed when they were going away for their 21st wedding anniversary. I was all alone in the world, both parents were orphans and I was an only child. My father was a well-respected member of the community and held a position as CEO of the main employer in our community. My mother although didn't work as she didn't need to but was on a lot of committees and did a lot of voluntary work, so I was always left alone and in some respects growing up I was a latch key kid. I was spoilt rotten and got almost anything and everything I ever wanted. I had just finished at university when the accident happened, they were flying over the Pacific when the plane was lost, the bodies were never found, so no funeral could be held but everyone wanted a memorial service, so Dad's personal assistant organised it for me. He came round to the house and took me through the final draft of the day and we chatted it through, I was happy with things he had organised and said as much to him. I noticed that he kept looking at me when he thought I wasn't looking. I turned and smiled at him. "You know Lee" he said looking into my eyes. "I haven't seen you since you came into work with your Dad when you were 10, you have turned out to be a very good looking young man." "Thank you Scott." "You're welcome Lee, I am sorry if I embarrassed you but you really are good looking I am just surprised that you haven't got a string of girls in tow." He said smiling "Or boys of course." Now I was embarrassed and I felt myself flush completely and for some reason I felt myself wanting to be totally honest. "Scott I've never really found anybody that I have wanted to get close to." "You're not telling me you are a virgin are you?" I went very red once more and nodded. Scott smiled and came over to me sitting on the settee and sat down next to me, he put his hand on my knee "Now don't worry Lee, leave everything to me and I don't mean just the memorial service." I don't know what made me do it, but I turned to him and kissed him on the cheek. He smiled and I flushed even more. "Now Lee I must go as I have a million and one things to deal with before tomorrow, have you sorted out what you are going to wear?" I looked down at myself, I was wearing light denim skin tight skinny jeans with a white t shirt cropped just above my belly button and flip flops. I looked up at Scott and shook my head. "Well although you look great in what you are wearing you cannot wear that." He took me by the hand and led me upstairs to my bedroom. He looked through all my clothes and sorted out a pair of black skinny trousers and some dress shoes with a white shirt and black tie, he even found some clean dress socks that I didn't know I owned! "Right that's you organised. Now I must dash and I'll see you tomorrow, do you want me to pick you up?" I nodded again "Okay see you at 10:30 sharp." He turned and left. I sat on the bed and looked at myself in the mirror on the opposite wall. I just stared at myself and I saw nothing, not the long blond hair that I loved (both my parent loved it and agreed when I announced at 6 years old that I never wanted it cut) not the Scandinavian cheekbones of my mother or the sparkling blue eyes of my German father. I just cried and cried and cried. I don't know how long for but the telephone rang and bought me to my senses. I didn't want to speak to anyone so I let the answerphone take it. "Lee this is Mr Briggs of Briggs, Briggs and Stephenson, your parent's solicitors. I need you to come and see me as I need to go through the will with you, I'll see you at the memorial service and we can take it from there." I went back downstairs and made myself a bite to eat, I wasn't particularly hungry but I thought I ought to eat something otherwise I would faint. I sorted out something and had a beer also, well it wasn't as if anyone was going to tell me off! I watched a bit of television whilst I ate before crashing out and trying to get some sleep. I showered and dressed in the things that Scott laid out for me, I wasn't really with it and I felt that I was going through the motions. Scott arrived on time and knocked on the door as I opened it. "You scrub up well." He said trying to lighten the sombre moment. I smiled, closed the door and got into his car. I asked Scott if he could take me to the solicitors after the service, he agreed and said that he would be glad too. The service went well and was well attended the Church was packed with all my parents friends and colleagues, I hardly know most of them but they all consoled me and hoped I would be okay. Scott stayed with me the whole time and at one point took my hand and squeezed it which gave me a strange feeling and as I turned and look at him he smiled and it seemed to be calming. After the service Scott took me to the solicitors and Mr Briggs took me through the will, not surprisingly apart from a legacy for Scott everything else was mine. The house I was living in, the apartment in Beverly Hills, the villa in the south of France and the flat in Park Lane where Dad would spend time when he had to go into London. According to Mr Briggs I was a wealthy man. Scott drove me home and took me indoors "Scott are you doing anything for the rest of the day, I don't want to be left alone at the moment." "Of course Lee, anything for you." "Thanks, I'm going to change." I went upstairs and started to undress. I heard Scott climbing the stairs and I knew I wanted him to see me so I turned and hesitated and as he came into the room I pulled down my trousers and took them off. I heard Scott gasp as he saw me in pink frilly panties and stockings underneath the trousers. "Oh my God." I turned and went red even though I knew he was going to see me. "I had no idea Lee. I hope you don't mind me saying so but you look fantastic." "Thanks. Now you know why I am a virgin, I have never found anybody to accept me as I am." "Well, I fucking love the look on you and you are one good looking sissy boy." Lee sat on the bed "Come and sit next to me Lee." I sat down next to him in just the panties and stockings. He caressed my stockinged leg and saw my dick rise to attention inside the pink panties. He looked up and me and leant in for and a kiss pushing me down on the bed. He shoved his tongue into my throat and I returned the favour giving him mine, we made love with our tongues as I felt him get hard inside his suit trousers. I moaned as I knew it was me who made his dick get hard. I pushed him away and pulled his trousers down. I smiled and moved down his body and took the head of his dick into my mouth, I had never sucked on a dick before and wasn't sure what it would be like. As I licked I felt him start to leak pre-cum and as I had licked my own so I knew I would like it. I looked up at Scott who had his eyes closed and a huge smile on his face, I knew than I was doing something right. I took more into my mouth until half of him was in my mouth before I started to gag. He heard me gag "steady Lee. Take your time you are doing a great job for a first time." I looked at him and he was nodding and smiling. I looked down again and started sucking all I could, it was only half of his dick but clearly he was enjoying my mouth. "I'm going to shoot Lee." And he did just that. He shot all his cum into my mouth, I had no choice but to swallow and as I did so I felt myself cum inside my panties with a moan. "I was going to ask if you enjoyed that Lee but I can tell you did, my leg is getting wet." He said looking into my eyes grinning. I grinned back and nodded. "Good sissy. I think you and I are going to get to know each other quite well. He pulled me up to his face and kissed me again. "Enjoy that Lee." "Yes, it was wonderful, I know now what I have been missing." "Not yet you don't Lee." I looked at him frowning. "You are novice aren't you?" Again I went red. "I've told you Lee for a first time you are doing great, will you let me take your cherry?" I smiled at Scott knowing exactly what he was referring to. "Yes please Scott." "I can't wait Lee, but it will have too, I need to get back to the office and deal with a few things. But I will come back tonight if you want me too and stay over but only if you want me too." I pushed him back down and gave him my tongue. "Does that answer your question Scott?" "I'll see you later then." Scott dressed and left me alone on the bed grinning to myself, I smiled to myself for the first time in ages. I then felt guilty about sucking Scott's dick on the day of Mum and Dad's memorial and started to cry. I managed to get myself out of moping and thought again about what I did to Scott and got instantly hard again. I dashed to my laptop and read all I could about anal sex and what to do. After a couple of hours I was prepared, I found some more panties and pulled on the stockings and some jeans and a t shirt and waited for Scott. The front door went and I jumped up and opened it smiling "Well hello Lee, pleased to see me then?" I opened the door further and pulled him in, he had a bag with him and I grabbed it and dropped it to the floor closing the door. I reached in and kissed him giving him my tongue. "Mmmm I guess you are." He said grinning as he kissed me again. "Can we go indoors, although it is nice kissing in the hallway, we will be more comfortable on the settee." Scott pulled me into the lounge and onto the settee. "Now that's better. First off I need to give you this." It was a letter addressed to me and the envelope was a date, it was written on the day I was 12. "Open it Lee." It was a hand written letter from my Dad, I recognised the handwriting. I read it aloud. `Lee if you are reading this it means that both Mom and I are dead. Please know that I love you more than you will ever know and I know what you are going through right now. Both Mum and I were orphans as you know, so we are both aware of the feelings you have right now. Hopefully this letter was handed to you by Scott my P.A. I want you to get to know him, he will be a real friend to you. I know you wear stockings and panties under your clothing and I also know that Scott is a sissy boy lover.' "My God he knew." Scott said aloud "fuck he knew all about me and I thought I was discreet. Fuck." I continued with the letter. `You are a sissy yourself even if you do not really understand your feelings right now, Scott will help you explore yourself and become what you really are.' And it was signed your ever loving Dad. "My God my Dad knew all the time about me wearing panties and stockings, and he did nothing about it." "More to the point Lee he knew I was a sissy lover and didn't say, he just accepted it." We looked into each other's eyes, your Dad was a great boss and I shall miss him dearly, he was the best boss I have ever worked for. I think he wanted us to get together, how can you and I not follow his instructions?" I smiled and kissed Scott on the mouth giving him my tongue "take me to bed." And I smiled and he picked me up in his arms and carried me upstairs. TO BE CONTINUED...