Date: Tue, 26 Apr 2016 11:34:34 +0100 From: Iain Bell Subject: Scott Finds A Sissy - Chapter Two. SCOTT FINDS A SISSY – CH2. 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. Scott lay me on the bed and he took off his clothes, I watched as he undressed. When he was naked his dick was standing to attention and was so hard it was pointing to his navel. I moved to the side of the bed and undressed myself and lay in my panties and stockings. I moved to take my stockings and suspender off "Let me Lee." Scott moved and unclipped my stockings from the suspender belt and slowly rolled them down. "Beautiful shaved legs Lee, nice and smooth, he pulled down my panties and I lay naked my own dick harder than it ever has been before. Scott lay next to me and rubbed my skin all over "You are nice and smooth all over Lee, beautiful, really beautiful." He leant over and kissed me. "Now lay on your back." I moved and Scott got between my legs, he kissed me moving down towards my tits and licking and sucking on each one as he moved down my body. He reached my dick and took that in his mouth and licked all-round the head and shaft. I took in a deep breath and he looked up "Not yet baby, not yet." He licked my balls and got between my legs and lifted them over his shoulders. He took the lube he must have had in his bag. He squirted some on his fingers and applied it to my arse, it was cold as he rubbed it into the crack of my arse caressing my arse lips as he went. He leant down and kissed me as he inserted one finger in my arse, he was so calming I didn't feel a thing until he inserted a second finger. I closed my eyes as the discomfort was alarming. "Easy now baby, I won't hurt you, I am loosening you up." I opened my eyes and he was staring into mine. He was smiling and so easy going, I knew that he wouldn't hurt me deliberately. "I am sorry I am not experienced Scott, I was so scared at school and university from showing my hand and being labelled, I did nothing and got the reputation of being a nerd and a swot which is better than being labelled a queer and a pervert." "Hey baby, I don't care about that, just say to yourself that you have saved yourself for this moment. The moment when I take your virginity, the moment when I make love to you." Scott was so easy on me I didn't feel the third finger go in my arse until he started to move and swivel as he loosened my arse ready to take his dick. Scott pulled his fingers from my arse and put the head of his dick at my arse lips and gently pushed inside, the head plopped into my arse and he stayed put until I got used to something invading me. I smiled and nodded and he gently pushed inch by inch into my virgin arse. I was soon to feel his big balls banging at my arse lips and I knew he was filling me totally and fully. "That's it Lee, I am all the way inside you, how does it feel?" I started to cry "what's up baby am I hurting you?" "No you are not hurting me, it feels so nice, and you have been so gentle with me. Please fuck me Scott, make me your woman." Scott leant down and licked away my tears kissing me deeply and lovingly before starting to fuck me. I was moaning all the time now and starting to love the feeling of having a man's dick in my arse. Scott built up a good rhythm and was now fucking me quite hard, I yelled out some obscenity and shot my load of cum all over the both of us. "Oh fuck yeah baby." And Scott pushed into me one more time and stayed deep, I felt him shoot his load inside my arse. I felt every pulse of his dick filling my arse with his hot manly seed. Scott collapsed on top of me kissing me "Baby that was one hot fuck for a virgin. I hope that you liked it and will want more." "Scott that was one of the best feelings I have ever had. I feel." I stopped talking and thought for a moment or two "I feel like that I have died and gone to heaven, I want that feeling again and soon." "Let me recharge my batteries and I can fuck you again, lay by my side Lee and we can cuddle." I couldn't settle and we ended up spooning with Scott resting his dick in the crack of my arse, I snuggled loving the feeling of his body so close to mine. Scott put his hand over my chest and rubbed my chest I reached out and kissed his hand. "Do you have to go anywhere tomorrow?" "I have a couple of meetings as the board need to look for another CEO and I need to organise interviews etc. Apart from that no." "Okay, you're coming back here I hope?" "Of course if you want me too." "I do and I wouldn't want to disappoint my Dad." I turned and kissed him before turning back and snuggling close. "I could easily get used to snuggling you close." "Mmmm so could I, Lee." I must have fallen asleep as the next thing I knew was it was dark and I felt Scott was hard and his dick felt good against my arse, I pushed against it moaning. "You want some more Lee?" "Yes Scott, I do. Please fuck me again." I turned onto my back and Scott came on top of my and we kissed. He lifted my legs over his shoulders and I felt his hard dick at the entrance to my arse. I had leaked during my nap but I was still wet and needed only a little lube. He pushed inside and although I was uncomfortable as it hurt a little it felt great going into me once more. "You feel okay Lee?" I nodded and grinned at him. Scott leant down and kissed me "Do you like feeling me inside you, do you like my dick fucking your pussy?" "YES" I screamed out and pushed against him getting more of his dick into my arse. Scott started fucking and he fucked me hard, ramming in and out of me. Scott moaned and I felt him unload inside me again, I felt every shot of cum as he let loose in me. Scott leant down and kissed me "Thank you Lee for allowing me to fuck you again, I know that must have been a bit uncomfortable for you so soon after your first ever fuck." "It was, but I wanted and needed it. I think I am going to need you to fuck my arse often." "Lee, I will only be too happy to fuck you but it is not your arse any more, it is your boy pussy." And Scott kissed me lovingly and deeply. He pulled out and he went down the bed and kissed my boy pussy licking and taking his own cum from me. He moved up the bed and kissed me giving me his cum from my boy pussy, I took it in and swallowed it moaning all the time. "Yeah good sissy." And he snuggled me close again. We dozed off again with his half hard dick nestling in the crack to my boy pussy. I woke during the night twice to Scott entering me and fucking me hard depositing even more cum in my wet boy pussy. The next morning I got up and showered and cleaned myself whilst Scott laid in bed snoozing. I dressed in clean panties and put on my suspender belt and stockings and padded down stairs to make the coffee. Scott must have woken and smelt the coffee and he came up behind me and kissed the back of my neck. "Morning Lee." I turned and kissed him throwing my arms around his neck. "No regrets?" "No." "Good sissy." We drank our coffee "Lee have you ever gone further and dressed totally female?" "No, this is as much as I have ever done." "Would you like too?" "With you by my side, I think I can find the confidence and would like to try." Scott grinned "good sissy, I'll go shopping and get a load of things that I like and hopefully you will too. When I come back after work tonight you can have a practice and we can see what you think." Scott took his coffee and went upstairs and had a shower. He came back wearing a suit and ready for the office. "I think I prefer your body naked Scott." I giggled and kissed him. He returned the kiss. "Hold that thought until tonight." He kissed me again and left for work. I wondered what I was going to do today, I decided to do some research on the internet. I got to work and after a couple of hours I knew how to apply make-up, I found a couple of places that sold underwear including bra's and inserts that would give you good looking tits. One place was in London and I rang them and made an appointment for this afternoon. `Now what shall I wear' I thought to myself. I looked through everything and chose a pair of skin tight yellow skinny jeans with some simple white Converse and a white T shirt with a large belt. I looked in the mirror and liked what I saw and headed out. I made good time and arrived slightly early, I went in and told the guy behind the counter who I was. He smiled looked me up and down "you are one good looking sissy boy, I have a great body to work with." He put the" closed sign on the door and locked it. "We have all the time we need. Now strip off and let me see what you are wearing at this moment. I hesitated for a moment "come on sissy." I stripped off and he looked at me in my stockings and panties. "Very nice but we can do better." He rushed around the shop grabbing things "Have you thought about thong panties as your man can move the thong aside to fuck your boy pussy." I smiled and nodded. He came back with several sets for me and I selected a dozen I liked he grabbed a matching bra for one of the thong panties and put it on me and filled it with life like boobs. He stepped back and shook his head "no, far too small, I think this sissy needs to go larger." He got a larger bra and I managed to put it on myself and he inserted the tits. He stepped back "much better. Have a look in the mirror." "My goodness." I gasped as I looked in the mirror. "Do you think your man will like the look?" "I look like a slut, aren't the tits a bit large?" "No they are perfect, please trust me, he will fucking love them." For some reason I did trust him and nodded, he selected the matching bras for all the thong panties. "Now what about stockings?" He showed me lots and lots of them in various styles and I decided on 10 different pairs. He totted up the amount I owed and I paid up, I realised I was still naked and dressed back in my own things and left happy with my purchases, I just hoped that Scott liked them too. I made my way home and indoors, I just had to try on my new things. I dashed upstairs stripped off and put on the black fishnet stockings and the yellow thong panties and matching bra. I put the inserts in and walked round the house for a bit except I kept on staring at myself in the mirror and turning myself on. I worked on a few things, had a bite to eat and before I knew it time was marching on and I ran upstairs stripped again and douched my boy pussy ready for Scott. I dressed in the same things again and went downstairs I heard Scott walking up the gravel drive. I opened the door as he approached "fuck Lee, you look" he stopped looked me up and down and said "fuckable" he pushed me indoors and closed the door. He dropped all the bags he was carrying. He shoved his tongue in my throat and kissed me deeply. "I had no idea you had such things." "Actually I didn't I went out today and bought these and some other things, I wanted to surprise you." "Well you have managed it sissy." He dropped his trousers "Now suck my dick it needs your mouth right now." I dropped to my knees and took Scott into my mouth, I licked the head with my tongue causing him to moan I slowly went deeper taking half his manhood into my mouth until I felt myself start to gag, I wanted more and I wanted all of him this time, I swallowed through the gagging and suddenly I felt his balls hitting my mouth. "OMG sissy well done, oh fuck that feels good. ARGHHHH and he spasmed and shot his man cream deep into my throat. I pulled off and took a sharp breath. "I wanted to do that so much, I am glad I was able to take all of you." "Lee you are so fucking talented." And he kissed me "now I was to see you dressed in your new clothes." He carried all the bags upstairs for me and went back downstairs. I looked in them all, make-up, shoes, t shirts, blouses. Dresses, skirts. In fact everything a good sissy needed. As I had investigated make-up on the internet, I actually found putting it on fairly easy, I looked at myself and thought that I looked good. I looked through the things that Scott bought and chose a black leather mini skirt with a white see through blouse. You could see the yellow bra through the blouse. I looked through the bags of shoes and boots. They were all high heeled and finally selected a pair of long boots with a stiletto heel. I put them on, zipped them up and stood up. I nearly fell over a few times but I found that I could eventually walk in them after a bit of practice. I went downstairs very gingerly into the lounge where Scott was sitting on the settee. He took one look at me and gave me a wolf whistle. "You are fucking gorgeous Lee. What a transformation. He came over and gave me a peck on the lips." Stay right there I am going to shower and change out of this suit. Open a bottle of wine will you baby and bring it into the shower." Scott went upstairs and I opened a bottle of white wine and took that and two glasses upstairs and poured them. Scott jumped out of the shower his dick rock hard "See what you do to me Lee?" he dried himself and looked through his bag and pulled out some tight black skinny jeans and a Lacoste polo shirt. He went to pull on some boxer shorts. "No you don't Scott. I want you commando under your jeans." He smiled and nodded and dressed. "Now Lee, you know you look fucking beautiful don't you, how do you feel about going out for a meal?" I shook my head "Go on sissy, please go out with me on a date. I want to show you off." "I'm not sure Scott, everyone will know I am a bloke." "They won't, please believe me, you look better than some of the real girls in the office that throw themselves at me." I looked unsure and he could tell. "Tell you what, how's about I ring for a pizza and you can go to the door and if he thinks you are a girl then you go out on a date with me exactly as you are." "Erm, okay then." I said still very unsure. He got on the phone right away and ordered. 45 minutes later the front door went. "Go on then sissy." And he pushed me towards the door, I reluctantly opened the door. The guy looked at me up and down and smiled "Here's your pizza miss." I took it from him and smiled back and turned but not before looking back and blowing me a kiss. I closed the door, Scott came from the lounge and looked deep into my eyes "What did I tell you Lee." "He thought I was a girl." "Of course, I told you that you looked good. Now am I taking you out on a date or not, you did promise." I nodded reluctantly "Good sissy." Scott got on the phone and rang for a taxi which arrived right away. TO BE CONTINUED...