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It's amazing the things you remember from your childhood on important days of your life. Today I remember when my father died from pancreatic cancer when I was seven. I remember the funeral that followed and the sadness in my mother's eyes as we left the gravesite. He was fifty-two years old. My mother married my father when she was twenty-one and he was forty. Of cause everyone told her he was too old for her but my mother didn't care they were in love. It took five years for their love to bear fruit. My mother had been trying to have a baby since she and my father had first gotten married. When they finally resigned themselves to being childless I came along. Though I was a two and a half months premature and only weighed two pounds and three ounces I was a welcome sight to both of them. As a child I was never sickly though due to my premature status I never grew into the strapping young lad that my parents had hoped for. By the time I was sixteen I stood around five foot two and weight less than ninety pounds. This is not to say my mother was disappointed in me. No she was quite proud of me. I was an "A" student and captain of the debate team for my high school. I was also a good actor though the roles I could play were hampered by my small stature. My mother didn't coddle me at all. When I reached the age of fourteen I was put to work in the family restaurant that she and my father had started. At first I was a busboy cleaning up after our customers had left. I became a waiter at fifteen and then host at sixteen. The restaurant was quite successful in our small town, as everyone who lived in the town either came in to eat or ordered from our take out menu. Our home delivery service was a booming business employing several boys from the high school. On my seventeenth birthday I was given a new car from my mother. The next day the reason I was given the car was apparent. My mother pressed me into service taking deliveries. It really wasn't that bad as it got me out of the restaurant. Besides the tips I received were quite generous. Most of my work time I spent in the restaurant but several times a week I would have to run one or two deliveries. It was mostly when one of the other drivers didn't come in. Like on nights when there was a game at the high school. It was on one of these nights that I met Stan Franklin for the first time. Stan was not one of our local residents. He owned a large two story home about ten miles outside of town that he lived in on the weekends. During the week he would go back to the city and live there until the following Friday. I knew exactly where his house was, as my mother had pointed it out several times. She was quite proud of the fact that he would pay extra for one of her meals. We normally didn't deliver that far out because of the cost to the driver. Stan was the exception seeing he made it worth the driver's time with a generous tip. I remember vividly the night I first met Stan. I had just turned eighteen three weeks earlier. I was looking forward to graduation from high school in less than two months and going on to a college in the fall. On that night I had to deliver four other meals before I made it to his house. The drive up to the house was well lit and there was a light on the front porch. As I reached for the doorbell I saw my hand was shaking slightly from nervousness. When he open the door I was take aback by the size of the man. He stood six foot five with very broad shoulders. He had brown wavy hair and brown eyes. He was so huge I felt even smaller than I really was. He was younger than my mother by about ten years. Stan smiled down at me and said, "You're the owners son, Scott isn't." I can't tell you how thrilled I was. No one took notice of me before. I smiled back and said, "Yes Sir Mister Franklin I have your order." "My name it Stan not Mister Franklin," he told me as he took the package. After looking at the receipt he handed me a fifty-dollar bill and said, "Tell your mother she makes the best Italian food I ever tasted." As I tried to give him his change he waved me off saying, "You keep the change." I then thanked his as he closed the door. It wasn't that spectacular of a meeting but to me it was a memorable one. My second meeting came about a month later. I had an order for Stan that was the only one I made that night. When I arrived at his house instead of answering the door he asked who it was over an intercom. "It's Scott from Teresa's restaurant. I have your order," I told him through the intercom. "Boy that was fast. I just got out of the shower come on in and I'll be right down," he told me. Seeing the door was unlocked I opened it and stepped inside. I placed his order on the hall table and waited for him to come down. A few seconds later I heard what sounded like moaning coming from the room to my left. It sounded like a girl in pain. My curiosity got the better of me as I stepped up to the door where the moaning was coming from and looked inside. I looked into what appeared to be a sitting room with a large screen TV on one wall. On the TV I saw a naked girl lying on her back with another girl face down in the first girl's lap. The girl on her back was moaning as the other girl was licking her pussy. I've seen those adult movies on the premium channels we had on cable but those didn't show it in the detail that this movie did. In this movie I could see the girls tongue go into the other girls slit as she licked her. It wasn't until I felt the hand on my shoulder that I realized what I doing. I must have jumped ten feet in the air as Stan chuckled and said, "Calm down buddy." "Sorry Mister Franklin I shouldn't have been watching. I mean it was wrong for me to watch that sort of thing," I told him as my face started burning with embarrassment. Stan chuckled again and said, "Don't worry about it I watch it all the time. If you would like you can stay and see the whole movie." I could feel myself blush even deeper as I said, "No I have to get back to the restaurant. My mother wouldn't understand." "Okay buddy maybe next time," Stan told me as he put his hand on my shoulder. He steered me toward the door as he placed a fifty-dollar bill in my hand and said, "You could come back after work and watch. I'll be up till three or four in the morning." "I don't think that would be a good idea. I don't think my mother would like me being out that late," I told him. Stan squeezed my shoulder and said, "Maybe some other time then." He then walked me to the door. It wasn't until then I realized he was only wearing a pair of boxers and a short robe. Two weeks after this incident I was standing in the restaurant seating customers when Stan walked in. As far as I knew this was the first time he ever came to the restaurant. Stan smiled down at me and said, "A table for one if you please." As I walked him to he table he said, "I expected you to come back last week. I was disappointed you didn't." "I'm sorry. It's not easy for me to get away from my mother. I don't usually go out after we close," I told him. "You're a senior now aren't you," he asked as he took his seat. I nodded my head as I handed him the menu. Nothing more was said as I had other people to seat. After Stan finished his meal he was standing by the check out with my mother when she called me over and said, "Scott honey Mister Franklin said he knows a few professors at NYU and he thinks he can help you get in. I know your grades are good and your SAT's are outstanding but it never hurts to know some one that knows some one." I was shocked by what they were saying. First of all how did he know I wanted to go to NYU? That was my first choice and the one I hoped would except me. Before I could get over my surprise Stan said, "Why don't you bring over your application after you're through here and I'll go over it with you. On Monday I'll give it to my friends and put in a good word for you." "He can go now. I wouldn't want to inconvenience you," my mother told him. "Scott I'll see you in an hour or so. Teresa thank you for a wonderful meal as always." Stan told us just before he left. After Stan was gone my mother said, "Scott go home and change into something nice before you go over there. You want to make a good impression on Mr. Franklin. Don't over stay your welcome but don't run out on him either. We don't want him thinking we're using him." "Okay Mom but how did he know I wanted to go to NYU?" I asked. "I told him," my mother told me as if it made perfect sense. Then she explained. "He asked me if you were going to college and I told him you want to go to NYU. That is where you want to go isn't it?" I had no idea what was going on but I wasn't about to turn down an offer for help. So I went home and showered then put on a clean pair of khakis and a polo shirt before driving out to Stan's house. All the way to his house I wondered if he was serious about helping me get into NYU or was this just a ploy to get me away from my mother. I wouldn't mind seeing some more of the porn movie I had seen, but I wouldn't mine help getting into school either. I didn't even have to ring the doorbell this time as Stan open the door before I reached it. "Come on in Scott," he told me. Stan must have come home and showered too as his hair was wet and he was now wearing a pair of black pajama pants and a black silk robe. I could see his bare chest, as he didn't bother to belt the robe. Stan took the application from me and said, "I'll get us a couple of beers and we'll look these over." "You were serious about helping me?" I asked. "Of course I was, why else did you think I would want you over here." He asked. I could feel myself blush as I said, "I thought you might be giving me an excuse to watch some more of those tapes you have. Stan laughed and said, "Well the real reason was for the school but that doesn't mean we can't watch a few fuck flicks when we're done." Stan told me to go into the room with the TV while he went for the beers. When he came into the room he was carrying a glass of beer and a bottle. He sat the glass in front of me and took a swig from the bottle. After he sat on the sofa next to me he started going over the application. For the next half hour he made changes and asked me lots of question. He would take drinks from the bottle and he made sure I took drinks from the glass. When he was done he put the application into a leather folder. He finished off his beer and put his arm around my shoulder and said, "Well Scott as far as I can see you should have no problem getting in. I'll grease the wheels a little but mostly it will be your merit that gets you in." "Do you really think I can get in?" I asked and I'm sure my excitement was showing. Stan handed me my beer and said, "I have no doubt next September you'll be in class at NYU. Now drink up and I'll get us a few more beers before I put in a tape." I had only finished half my beer so far but seeing I didn't want to disappoint Stan I drained the glass in one drink. While Stan went for more beer I realized that the alcohol in the beer was starting to affect me. I could already feel my head was slightly dizzy. I knew this was from the fact that I never drank much before. I had wine at dinner with my mom quite often but never more than a small glass and even that would give me a slight buzzing in my head. I also knew I would have to drink the next beer slowly as I had to drive home. Once Stan came back from the kitchen he placed the beers on the coffee table and then when over to the TV. As he put a movie into the VCR he said, "This is the movie you saw last week I figured you would want to see the rest of it." After he sat down he handed my beer to me as he took a drink of his own. As I tilled the glass to my mouth Stan reached over me for the remote. As he did his shoulder hit the glass and dumped the glass of beer all over me. We both jumped up at the same time and Stan said, "I'm so sorry Scott. God you're soaked." "It's okay it was an accident. I'll go home so I can changed," I told him even though I didn't want to go. I was looking forward to watching the movie. "I don't think that's a good idea Scott," Stan told me. "I mean what if you get stopped you've already had one beer and you're covered in another one. One whiff and a cop would bust you for driving under the influence. Besides what would your mother think of me once she smells beer all over you." He was right of cause. My mother wouldn't understand about the beer and why I was drinking it. Besides that I can't afford to get stopped. But what else could I do. Stan came up with a plan that seemed to work. "I could wash your clothes and when they're dried you can put them back on. I'm sure I could find something you could wear while they're washing. You could take a shower in my room while I find you something and put your clothes in the washer." Stan told me. Seeing I really had no other recourse I followed Stan up to his bedroom. It was a nice room with dark rich furniture. He had a king-size bed and two dressers. There was another TV in his bedroom, even though it was a projection screen TV it wasn't as big as the one down stairs. His bathroom was quite large with a large shower and a large whirl pool tub. The counters were tiled, as was the floor. There were mirrors on each wall and all the fixtures looked like they were made of gold. As Stan started to close the door to the bathroom he said, "Take off your clothes and hand them out the door then get in the shower. I'll put your clothes in the washer and find you something to wear." It didn't take me long to shed my wet clothes and hand them out to Stan. It also didn't take me long to shower but Stan was back in the bathroom before I was done. Through the door of the shower I heard him say. "I left you something on the counter. It's not much but it's the only thing I have that will fit you. All my clothes will fall right off you." Once I heard the door close again I stepped out of the shower. I looked around for the clothes he left me and saw what looked like a black silk robe sitting on the counter. It looked a lot like the one Stan was wearing. Once I dried off I picked up the robe and found a pair of black satin underpants under it. I quickly put on the underpants but I thought I had put them on backwards, as there wasn't an opening in the front. After I check the back of the underpants I saw it didn't have an opening either. That's when I noticed that the waistband as well as the leg openings had a small band of lace. I knew then that the underpants I was wearing was really a girl's pair of panties. My mind spun with what was happening. I couldn't figure out what to do. Surly I couldn't let Stan see me wearing girl's panties. I mean what would he think of me. But then I realized he must have known what they were. He did bring them to me so he should known. With no other option left open to me I put the panties and the robe on and I open the door to the bathroom. As I did so I could feel my face heat up with embarrassment. I had a feeling that Stan was going to laugh at me for wearing girl's panties. Stan took one look at my face and said, "Sorry Scott they're all I had that could fit you. If I gave you a pair of my boxers they would have fallen off you and that would be more embarrassing." Seeing he was sorry made me feel better about my predicament. Stan and I went back down to his living room to watch the movie. Before he started it he got us two more beers and promised not to spill this one on me. I chuckled as he sat next to me on the couch and we started watching the movie. The movie we were watching had a lot of girl on girl sex in it. There were two guys in the movie that fucked a girl or two but mostly the movie was about what the girls did to each other. From the minute the movie started my dick became hard and stayed that way through out the movie. Obviously the movie must have gotten Stan excited as well. As he held his beer in his left hand his right hand would move down and squeeze his cock every once and a while. I'm not sure why I noticed this, but I couldn't help watching him, as he squeezed it. I also realized that Stan's dick was a lot bigger than mine was. Mine is only four inches long and about the size of a quarter thick. Stan's looked like it was twice as long and three times as thick. I think the beer had something to do with my wandering eyes. After getting doused with my second glass and the shower after I had lost the fuzzy feeling in my head. But now that I had a second beer in me that fuzzy feeling came back quickly. When the movie ended Stan replaced the movie with another one before going into the kitchen for more beer. As he walked around the living room I could see his erection pushing out the front of his pants. My own erection was pushing out the front of the panties I was wearing but in my sitting position it wasn't as obvious. I could also feel a wet spot formed on the panties right where the head of my dick was. I was thankful I had the robe on as it covered my excitement. When Stan sat back down next to me the movie had already started. On the screen we watched a guy and a girl kissing passionately and I could see their tongues going into each other's mouth. We watched that for a few seconds before Stan asked, "Scott have you ever kissed a girl like that or been kissed like that." I knew the beer was working on me when I chuckled. It sounded more like a giggle when I said, "No I haven't been that lucky yet. Every girl I've ever met wanted to be my friend but not my girlfriend." "Well don't feel bad, most girls want one thing. As soon as they get it they want to change it. But god loves them, because I sure do. There's nothing like having a cute girl in your arms while your kissing them." We watched the movie for another thirty minutes or so. This had almost all guy girl sex in it. I watched girls suck on really big cocks and I watched the same girls getting fucked by these well-endowed men. It was quite exciting to watch and I couldn't help reaching down and give myself a squeeze. Stan was squeezing himself more and more and once he saw me do it he said, "You know Scott if you want you can take out your dick and masturbate I won't mind." I chuckled nervously and said, "I couldn't do that I would be too embarrassed." Stan laughed before saying, "I'll tell you what I'll pull mine out and you can pull out yours. This way there's nothing to be embarrassed about." Stan didn't wait for me to agree he popped the snap on his pajamas reached inside and pulled out his cock. I knew Stan's cock was big but until he pulled it out I had no idea how big. He made mine look like a needle, as his seemed to reach half way up to the ceiling. After I stared at his cock for a minute or so Stan said, "Come on Scott it's your turn now." With out even thinking about it and with out taking my eyes off Stan's cock I pushed the panties I was wearing down and pulled out my much smaller dick. I watched as Stan's hand moved up and down the length of his cock and I stroked my smaller one to the same beat. How long I sat there starring at him I don't know but I was finally heard Stan say, "You know you can touch it if you like. I like having some one else's hand on my cock. It feels better than doing it by yourself." I was quite embarrassed that I was caught staring at his manhood but Stan didn't seem to mind. He just put his left arm around my shoulder and pulled me closer. His right hand came off his cock and it reached over and took my right hand off my dick. He then wrapped my hand around his cock. In my mind I was telling myself that I should stop this but I couldn't get my body to cooperate. My hand simply started to move up and down Stan's cock as if it had a mind of it's own. At the same time Stan's left arm had moved down and encircled my waist. The next second his left hand was stroking my dick. Just the mere touch of someone else's hand on my dick was too much for me. I instantly felt my orgasm start to build but Stan wasn't ready for that to happen. Stan pinched down on the base of my dick and my orgasm subsided. Once I had calmed down his fingers started moving once more. My hand never stopped its up and down strokes. Stan kept me on the edge of orgasm for a long time. Each time I thought he was going to let me cum he would pinch down on my dick till I calmed down once more. It was agony, but a sweet agony. Each time I was close to cuming my hand would move faster on Stan's cock but he would slow my hand and tell me to make the pleasure last. How long this lasted I don't know but when the movie ended Stan stopped it and turn toward me. He cupped the back of my head in his hand and pulled my head closer to his. Even before he kissed me I knew that's just what he was going to do. Even though my mind was screaming for me to stop this, my left hand moved up and encircled Stan's neck. When our lips touched for the first time I felt a small spark jump between us. It was like there was magic in his kiss. When his tongue entered my mouth I licked it with my own. Stan saw I wasn't about to stop him so his left arm came away from my waist and it pushed my shoulder so we were closer. His right hand moved down and an instant later the satin panties covered my dick once more. Stan right hand then cupped my balls as his thumb started to massage the underside of my dick through the satin panties. My orgasm came over me quickly and this time Stan didn't try to stop it. I saw sparks before my eyes at the same time it felt like my dick exploded. I pulled my mouth from Stan's and gasped a loud moan as my dick filled my panties with cum. A moment or two later I felt Stan's body become rigid as he groaned out an "oh god". The next instant I felt his cock become larger as my leg was hit by something very hot and wet. Once our orgasms abated our lips met once more and we kissed for several minutes. After a few minutes Stan pulled his lips from mine and looked down at my leg before saying, "It looks like I spilled on you again. Let me take you up upstairs and clean you up." My mind screamed for me once more to stop this but Stan didn't give me a chance to stop him. He slid his right hand under my legs and his left held my back. He then stood and picked me up and carried me to his bedroom. All I did was wrap my arms around his head and held on. Once in his bathroom Stan placed me on my feet and helped me remove my robe. He then started the shower before he went to his knees in front of me and pulled the panties off. He helped me in the shower and a moment later he was naked as he joined me. I'm not sure but this didn't seem to bother me. In fact it felt good having him scrub my body clean with a washcloth. He made sure to scrub every part of my body from my face to my toes, from my dick to my asshole. When he was done I did the same to him even his most intimate spots. When we were finished in the shower he dried me off then took me into the bedroom. I stood naked while he went to a dresser and pulled out a baby doll nightie and help me put it on. As he was pulling up the panties I told him I really should be going home. Stan stood and said, "No you'll sleep here tonight. You've had too much to drink and your too tired. I'll talk to your mother in the morning and I'll explain you fell asleep watching a movie and I thought it best to just leave you on the couch. Now hop into bed while I get some clothes on." As I got into bed Stan put on a clean pair of boxers before siding into bed next to me. If I had any trepidation about sleeping in the same bed as Stan it evaporated the instant his lips touched mine. We kissed for a few minutes before Stan placed my head on his chest and I fell asleep instantly. When the intimacies of the night before hits the cold light of day your perspective changes. What was good and natural becomes wrong and immoral. When I awoke in Stan's bed for the first time I was over come with guilt. I felt guilty for enjoying the things Stan and I did the night before. I also felt guilty for the wanting to do them again. I knew I couldn't do those things with Stan any longer. It wasn't right, two men aren't supposes to do those sort of things together. Thankfully I didn't have to face Stan when I first woke up. By the time I open my eyes he was gone. At the foot of the bed I had shared with Stan I found my own clothes. And though I had enjoyed the satins I had worn I was relieved to put on my own clothes once more. Just as I had finish dressing Stan came into the bedroom. He had a sad look on his face as he said, "I was just coming to wake you. Breakfast is ready." Just looking at him I was over come with guilt. I couldn't look him in the eye when I said, "I should be going. I know my mother must be worried about me." Another thing to feel guilty about. Stan came over to me and placed his hand on my shoulder and said, "I've already talked to your mother. She understands you were too tired to drive home and you slept on my sofa. Before you go I think we should talk, in fact I know we should. Now come along before breakfast gets cold. I followed Stan down stairs and sat down to breakfast with him. We sat and ate together and for awhile neither of us said anything. Just when I thought he was going to remain quiet for the entire meal Stan said, "I hope you know I enjoyed our time together last night. I would like it if you came back again tonight after you're done with work." Stan was silent after that and I know he was waiting for me to say something. I didn't want to hurt his feelings so I said, "I enjoyed it too but I'm afraid what other people would say if they found out." "First of all, no one is going to find out anything unless we tell them," Stan told me. "I am not going to tell anyone. What goes on behind these doors stays here. Also we didn't do anything wrong at least not in my eyes. You were acting the girl's part and I was acting the boy's part it was like a play." I knew that was pretty lame reasoning, but I could see where he was coming from. After all I was dressed up like a girl in the panties and the robe. Even the nightie I wore to bed bespoke of the female gender. But I couldn't deny I liked what we did and I would like to do it again. I mean he showed me so much attention, more than any one else ever did. I just couldn't come out and say it. I'm not sure if Stan understood this but his next sentence seemed to say he did. As he stood up he said, "Scott if you want to come back I'll be here waiting. Your restaurant closes at ten so I figure you can be here by eleven. If you're not here by midnight then I'll know your not coming." "What should I tell my mother?" I asked. "Well Scott it's time to be an adult. Tell your mother your coming over here and you may be home late. It's time to cut the apron strings." Stan told me as he showed me to the door. I knew Stan was right about my mother, but was he right about everything. I was after all a man even though I had worn panties the night before. My mind was telling me what we did was wrong but my body kept giving me a hard on every time I thought about the pervious night. When I got to the restaurant my mother asked me about my application and what Stan thought of my chances of getting in. She didn't even mention the fact that I had stayed out all night. I told her about the application, she told me to go to work as if I hadn't stayed out all night. All day my mind went back to the night before. Several times I was so caught up in my daydream that a customer had to tap me on the shoulder to get my attention. It was probably around six that night when I convinced myself I would be going back to Stan's. I knew I couldn't stay away. It was my mother who gave me the opening I needed to tell her I would be going over to Stan's that night. About nine thirty she came up to me and said, "Mr. Franklin want's to know if we could still deliver a pizza tonight. I've already let the other boys go home. Do you want to deliver it, if not I'll tell him we can't?" I wondered briefly if Stan was giving me a reason to come over. Then I though he had no idea who would be delivering his order. After I thought it over I said, "Tell him we'll get it there. I'll take it and I may spend a few hours with him." My mother smiled and said, "Okay honey if you do come home late be careful driving. If you don't think you can drive stay the night like last night." A half-hour later I was on my way to Stan's this time I didn't bother stopping at home as I had a suspicion that I would be once more in panties and a robe. I figured I could shower before I changed. When I arrived at his door Stan looked surprised it was me who was delivering his pizza. I also saw he was once more wearing the black pajama pants and the silk robe from the night before. When he looked for the bill I told him, "My Mom said this one was on the house because you are a good customer." "Well tell her thank you but I still owe you a tip for driving it out here." Stan told me as he picked up his wallet off the hall table. I waved him off and said, "That's okay I was coming out here anyway." The look on his face told him I surprised him. He recovered quickly by saying, "Would you like to change so I don't spill anything on you." This was a problem that bothering me all day. For some reason Stan wanted me to wear girl's clothes. I didn't mind it but I wanted to know why. So I said, "I will if you want me to but why do you want me to? Are you gay?" Stan chuckled and said, "No I'm not gay but I'm not straight either. I'm bisexual. I like girls, but I really like boys that look like girls. I like knowing they have something under their skirts they shouldn't have." This was something I never heard of. I've heard about gays and lesbians but I never heard about guys that like boys that dress like girls. So I had to ask, "So when I put on those panties yesterday I looked like a girl to you?" Stan knew I was catching on to his game so he said, "Well you have feminine qualities but you needed some make up and a few other things. I would have to say, I think after some practice you could make a wonderful girl if you want." I thought this over. I liked Stan a lot and he was being pretty nice to me. I also knew I didn't have much hope of attracting a girlfriend with my small statue. So I figured I give this a shot and see how it works out. I mean the sex we had the day before was pretty good and it could only get better. I just wasn't sure what I would be expected to do. I was still pretty na?ve when it came to sex. After thinking this over I looked up at Stan and said, "Do you have something you would like me to wear. I'd like to give this a try." The smile on Stan's face couldn't have been brighter. He took my hand and led me up the stairs and into his bedroom. As we entered I saw there was a pair of red panties and a red satin robe on the bed. This told me he had hoped I would come. Instead of telling me to put those on he walked over to the dresser that he had taken the nightie from the night before and started going through the draws. He first pulled out a pair of stockings then what I would later find out was called a chemise. He also pulled out a pair of panties that matched the white chemise and a white garter belt. He also pulled out a pair of white high heels from the closed. As he stood in front of the open closet he said, "There a few things in here you could wear on top of you outfit. Why don't you look them over and decide on something. I walked over to the closet and looked inside. There were several dresses as well as several robes and long nightgowns. There were also quite a few pairs of high-heeled shoes at the bottom of the closet. There were sweaters, blouses and skirts, but not a single pair of women's pants. After looking over the array of women's clothes I asked, "I gather I'm not the first boy you've had here. Do you fine boys willing to do this often?" Stan chuckled and said, "Not often enough but I have entertained a few sissy boys, no one locally until you. They usually came here with me from the city." "In that case do you have any makeup I could use?" I asked. Stan looked surprised as he asked, "Do you know how to but it on?" I smiled and said, "I've been in a few plays and I had to wear make up on stage, but I didn't have to make myself look like a girl. I've also watched my mother put on her makeup quite often as a child. I'll give it a try but I can't make any promises on how good I'll look." Stan walked over to what looked like a writing desk. He lifted the center and flipped up a mirror. In the space under the mirror was an array of cosmetics. He then said, "In the draws you will find more, but don't over do it. I want a pretty girl not a street whore." "I'll try my best now if you would give me some privacy I'll try an turn myself into a pretty girl for you," I told him. I was hoping that Stan would kiss me but instead he went toward the door and left the bedroom. Once Stan was gone I took a quick shower. When I was dry I sat at the makeup table and looked over the cosmetics. I really didn't know where to start, as every thing looked so foreign to me. In the end I decided to start on my eyes, as it was where my mother always seem to start. I picked up the mascara first and looked it over. I wasn't sure how to start but when I though of my mother my hands seem to know what to do. After almost poking myself in the eye I was able to get the brush on my eyelashes. I didn't put on too much, as it seemed like I didn't have on enough. When my eyelashes were slightly blacken I stopped and thought it was enough. I didn't try putting on eyeliner, as I was sure to mess it up. I then used a light brown eye shadow to darken my eyelids. I put a little blush on my cheeks then used a deep red lipstick on my lips. When I was done with the makeup I looked my face over. How feminine my face looked surprised me. I mean my face looked like any girls at school, though I wore less makeup than most of the girls at school wore. As far as my head went I looked like a girl except for my hair. My hair was another problem. It wasn't that long as I had just gotten a hair cut, and no matter what I tried to do with it, it still took on the shape of a boy's haircut. In the end I mousse it down and tried to fluff it up. After giving up on my hair I sprayed myself with a little perfume before moving over to the bed to get dressed. I took the panties first, but when I went to put them on I noticed that they didn't have a back to them. There was a thin strip of satin cloth that connected the triangular piece that would cover my dick and balls to the waistband in back. When I slid these on I realized that the strip of cloth was suppose to go between my butt cheeks. This really felt quite odd as the strip settled between my cheeks. I next put on the stockings. I knew how to put these on as I had watched my mother put on pantyhose hundreds of times in the past, well until I was about eight anyway. Stockings were actually easier as I only had to worry about one leg at a time. I wasn't really happy with them as they pulled on the hair of my legs and once they were on all the way the hairs made my legs itch. I guess that was why girls shaved their legs all the time. Once I had the stockings on I turned my attention to the garter belt. I had seen girls wearing these before on TV, but I never saw anyone put one on before. I couldn't even tell the front from the back. Getting it on was easy enough as it had a clasp like a bra but was it suppose to go in front or in back. I finally decided that the clasp was suppose to go in back as there was a tiny pink bow that was centered on the opposite side. I figured the bow should go in front. Next came the garter straps. At first they were too long and it took me some time to figure out how to shorten them. It also took me some time to figure how to attach the garters to the stockings. By the time I got the garters attached to the stockings and they were tight enough to pull on the stocking I had broken out in a sweat. Before putting on the chemise I went to the bathroom and wiped off with the towel I had used earlier. I them put on the white chemise and went to the closet to find a top. There were a few dresses I was sure would fit me, but I knew it was late. I couldn't see wearing one of those at this hour. For the same reason I didn't look at any of the skirts or sweaters. Instead I chose a white satin robe that seem to match what I was already wearing. Seeing the panties and the chemise was satin the robe seem to be perfect. I had save the heels for last for a reason. First of all I knew they wouldn't be easy to walk in and I wanted to get dressed before I tried them. They weren't really high, as the heel was only two and a half inches tall. They had straps that crisscrossed over my instep and a strap that went around my ankle. When I got both shoes on I stood for the first time. I was surprised that my balance was thrown off and I nearly fell over before I took a step. Once I got my balance right I took a step. This was hard too as I almost lost my balance again and fell over. Each step after that made me feel like I was going to twist my ankle. I had to walk around the room several times before I could get use to them. I wound up taking tiny steps and mostly walked on the balls of my feet. Once I could walk with out tripping I went over to a full-length mirror and looked myself over. My legs looked rather nice in the stockings though I could see the hairs on my legs. They actually looked like girl's legs. Seeing the rest of my body was covered in white satin I looked like a flat chested girl. The only thing that didn't look feminine was the way my dick pushed out the front of the panties. I had also noticed I had licked off the lipstick I had put on earlier. I went over to the makeup table and re-coated my lips. When I was done I went to put the lipstick back on the makeup table. Instead I dropped the tube into the pocket of my robe. I then went looking for Stan. I only had to walk down stair, which was not an easy task to find Stan. He must have heard me walking down the stairs as he came out of the dinning room just as I landed on the first floor. The smile on Stan's face made all the work I had gone though worth it. He also had a hungry look in his eyes, as he looked me over. For some reason I couldn't explain that look made me feel special. Stan took my hand in his and said, "God you're really beautiful dressed like that." I felt myself blush before asking. "Do you really think so? I know my makeup could be better." "With practice you could pass anywhere as a real girl." Stan told me before he gentle pulled my hand so I would follow him. Stan guided me into the dinning room and asked me to sit. He then pulled a chair over so he could sit directly in front of me. He took my hands in his and asked, "How does it feel to wear girl's clothes?" It only took me a second before I said, "I like it. I like how they feel though I don't care for how the stockings feel right now. If I get a chance to do this again I think I'd like to shave my legs first." Stan lifted my hands to his face and kissed my hands before saying, "I'm glad to hear you say that. I'm also glad you want to do it again. I don't think I could look at you again as a male and not see the girl that sits in front of me. You will always be a girl in my mind." I don't know why but what Stan just told me didn't bother me. I didn't mind that he would always think of me as a girl. With out thinking I said, "I always want to be a girl for you." By the look in Stan's eyes I could have sworn he was going to kiss me but instead he said, "You do realize what we're doing has nothing to do with me helping you with college. I mean I would help you get into NYU with out what we're doing together. I just don't want you thinking I'm using you." That thought never occurred to me and I told Stan as much. He then pulled me onto his lap and we kissed. It was the sweetest kiss we shared to that point and it was one I would remember always. When Stan stopped kissing me I said, "I'm not sure what you expect from me, sexually speaking. I've never been with anyone before and you may have to teach me." Stan kissed my cheek before saying, "I'll teach you everything you need to know on how to please a man. If that's what you really want. That means I don't want you saying we shouldn't be doing this to each other. I want a she-boy that wants to be a she-boy. Not a boy who only acts like a girl when it come to sex, I want you to be a girl all the time around me." I wasn't sure I wanted to be a girl all the time but I also knew I wanted to give it a try. I want to see how far we could take this. I knew my life, as a boy wasn't the best. I hated getting picked on by bigger boys in school and I hated the way girls treated me. They always treated me like a little brother. Mostly I hated being ignored by just about every one. It didn't take me long to think this through and I said, "I want you to teach me how to be a she-boy. I want to be a she-boy for you." Stan kissed me again though this time it was hard like he was over come with passion. This time his hand moved up and covered my flat breast. A few seconds later I felt his thumb and forefinger start to play with my male nipple. I was shock by how sensitive my nipple was. I couldn't stop the moan >from escaping my throat. We kissed passionately for several minutes then Stan stood me up and said, "Come on my beautiful sissy boy I want to show you a tape of what sissy's do for their lovers." Stan took me by the hand and walked me into the living room where the big screen TV was. As he started looking through tapes he said, "Why don't you go into the kitchen and get me a beer and a glass of wine for yourself. Girls shouldn't drink too much beer, as it's bad for your figure." As I went into the kitchen I could feel Stan's eyes follow me every step of the way. I liked knowing he was watching. I knew quite a bit about wines and when each should be drunk. I knew that a nice Merlot was good this late at night and it was rather low in calories, compared to other wines. After pouring myself a glass I opened a bottle of beer and went back into the living room. When I got back into the living room Stan was standing by the sofa waiting for me. While I was gone he had taken off his robe but left the pajama pants on. He took the wineglass and the bottle of beer from me and placed them on the coffee table. He then took me in his arms and kissed me. Sometime during the kiss he removed my robe, but I really don't remember it. We then sat on the sofa. Stan sat in the corner with me right along side him. There was no pretence that we were just going to watch the movie. Stan pulled me close and kept his arm around me as if he was afraid to lose me. When the movie started there was a man and a woman on the screen. They were in the middle of a kiss when the action started. It didn't take long for the girl to drop to her knees and after unbuckling the man's pants she started sucking his cock. The man wasn't hard when she started but in a few minutes his cock started to grow. The girl was quite good at giving head, as she didn't seem the least bit bothered by the man's huge cock. If I had to guess I would have to say he was at least as big as Stan was. I wasn't sure why we were watching this movie, as it reminded me of one we watched the day before. That was until the girl got off her knees and the guy went to his. As he pulled off the skirt she was wearing I saw there was something odd with her panties. As the guy pulled off her panties I realized what made them look so odd. The girl had a cock where she should have had a pussy. She looked just like a girl. She had long brown hair and full breasts just like a girl. The only difference was the cock and balls that hung from her pelvis. Even her legs looked like a real girl. As the guy in the movie started to suck the girl's cock Stan whispered in my ear. "Honey take out my cock and play with it. I don't want to cum but I like feeling your sweet little hand on my cock." I'm not even sure I though about doing it before my hand reached over and undid the snap on his pajamas. I then reached inside and grasped his manhood in my hand. Stan was already hard and it took a little persuasion to get it out of his pajamas. At the same time I couldn't take my eyes off the TV. As I slowly stroked Stan's cock I continued to watch as the guy sucked the girl's cock till it was as hard as his was. Once her cock was hard the guy turned the girl around and started kissing her bottom. It was then that Stan whispered, "Honey pull your feet onto the sofa so I can play with your sweet ass. I've thought about that beautiful ass for weeks now." I couldn't understand why Stan wanted to play with my ass. I mean we all know what comes out of there, but I wasn't going to deny him anything at this point. I pulled my legs up so I was practically lying on the sofa. Stan reached behind me and started massaging my cheeks. At the same time Stan leaned over and kissed my head. Even though I couldn't understand why anyone would want to touch my backside it didn't stop me from feeling the pleasure of his caress. I mean it felt odd but good to have his hand on my bottom. But what made me moan was when he slid his finger along the crack of my ass. I continued to stroke Stan's cock as a moaned escaped my lips each time his finger went up and down my crack. I could barely concentrate on the movie, as I wanted to close my eyes and relish in the pleasure of Stan's finger. But I really wanted to see what the two on the screen were going to do next. I watched the guy lick the girl's cheeks before he started licking the crack. I really couldn't imagine any one doing what he was doing. What really shocked me was when I saw the guy lick her asshole. I mean I could see him run his tongue around the hole like it was a pussy. At the same time Stan reached over to the end table next to him and picked up a bottle. On the label I saw the words super lube as it passed my head. A second or two later I felt Stan pull the strip of cloth from between my ass cheeks and then I felt something dripping on my ass hole. As I watched the guy stick his tongue up the girls ass hole I felt Stan push a finger up mine. At first there was a bit of pain but that quickly vanished as a moan escaped my lips. I was surprised by how good his finger felt as it slid inside me. Stan started fucking me with his finger and it was like nothing I ever felt before. I couldn't stop the moans and groans from coming out of my mouth, not that I thought about stopping them. I even rolled over to give Stan easier access to my ass. This brought Stan's cock only inches from my face. His cock looked so big and yet so beautiful this close and there was clear fluid leaking out the tip. I couldn't stop my self as I leaned over and kissed his beautiful head. My lips touched that clear fluid and my tongue quickly licked it off my lips. There was very little taste to the fluid though it was slick as oil. It had a manly taste though not unpleasant and I leaned over and kissed his cock once more. This time I made sure to get plenty of the fluid on my lips and again I licked my lips to taste the fluid. After smacking my lips I started licking the head of Stan's cock. I heard Stan moan before he said, "That's it honey lick my cock but keep you eye on the TV." I had to force myself to look at the TV as my tongue moved all over the head of Stan's cock. On the screen I watched as the guy who was now standing eased his cock between the girl's ass cheeks. A close up shot showed how the head of the guy's cock penetrated the girl's ass hole. The girl moaned deeply as she begged the guy to fuck her pussy. It was the first words I heard on the movie. At the same time I felt Stan slide a second finger into my ass. At first it felt tight. I really didn't care, as the only thing I cared about was what I was doing to Stan's cock and the pleasure of his fingers in my asshole. When Stan saw I was enjoying his finger fucking he added a third finger. At the same time I took the head of Stan's cock in my mouth for the first time. I didn't go too deep like they did in the movie, but it seem to please Stan as I heard him moan and I felt his cock lurch. His cock felt good in my mouth as I sealed my lips around the head. I sucked slightly and I felt some more of the clear fluid leave Stan's cock. I tried moving down his shaft like they did in the movie but his cock quickly filled my mouth. By this time I had forgotten all about the movie as I tried to suck my first cock. I could hear the girl asking to be fucked harder and I could hear grunts and groans coming from the TV, but I didn't care by this point. I only want to suck Stan's cock as he continued to finger fuck my ass. After a few minutes I felt Stan's hand on mine as he forced me to stroke his cock. Once I had the rhythm he wanted I felt his hand move to my head. His other hand never left my ass, as his fingers seem to go in deeper. I can't tell you how great this felt as I sucked my first cock and had my ass fucked at the same time. My mouth soon grew used to the thickness of Stan's cock and soon my lips were moving further down his shaft. It didn't take long before I could feel the head of his shaft touch the back of my throat and my lips slid easily up and down his shaft. I felt Stan's hand on my head as if he was guiding me in my first blowjob but he never forced me to go deeper than I wanted. At the same time I started humping the sofa as Stan continued to finger fuck me. I was beside myself with pleasure and I wanted to cum with Stan's fingers in me but I also wanted Stan to cum too. I wanted to make him cum. I didn't have long to wait as I heard Stan say in a gasp. "Oh god girl I'm going to cum. I'm going to fill your mouth with cum any second." I wasn't sure if this was a warning or a statement but I wasn't about to stop. A few seconds later I felt Stan become rigid and his cock became harder. A moment later I received my first load of man cum. It squirted out of his cock like a bullet out of a gun. It instantly filled my mouth and some squirted out the sides of my lips. I tried to swallow knowing guys loved it when the girl swallows. I couldn't even tell you what it tasted like except it was thick like egg yokes and hot like melted butter. I didn't have time to taste it fore as soon as I swallowed the first load the second one was filling my mouth. How many times he squired his love juice in my mouth I couldn't tell you as it was all I could do to keep it >from escaping my lips. It wasn't until he was drained that I could taste it. It was slightly bitter like a dark beer and slightly salty like beer. There was a slight metal taste to it though that didn't bother me. I actually found I like the taste and I knew this wouldn't be the last load of man cum I would drink. I continued to suck until Stan pulled my head off his over sensitive cock. Once my lips were free of his shriveling cock I saw there was some of his cum that had escaped my lips. I licked up all I could find and swallowed it down like it was manna from heaven. Once Stan's cock had shriveled into softness and I had cleaned up any cum I missed I realized I didn't get to cum with him. I was too preoccupied in my endeavor to bring my lover off. I also realized that the movie we were watching had ended and the TV screen was nothing but snow. I took the remote and turned off the TV then rested my head on my lover's tummy till he recovered from his orgasm. It only took a few minutes till I felt Stan stroke my head like he was petting a dog. I then heard him say, "You surprised me girl. I didn't think you would suck me off the first night." "I'm sorry should I have waited until you told me too?" I asked even though I knew the answer. Stan chuckled and said, "No you did just fine. Most first timers have to be talked in to sucking cock. The way you seem to take to it naturally tells me you really enjoyed doing it." "I did enjoy it Stan. As soon as you're ready I'll do it again. I especial like doing it with your fingers in my backside," I told him before I kissed his cock once more. Stan turned me over so he could look at my face before he said, "I think you could be just the girl I'm looking for." With that said he kissed me deeply. When we ended our kiss I asked, "What do you mean just the girl your looking for?" Stan caressed my side as he said, "I'm looking for a boy who is sweet and feminine and likes being a tranny. Most of my lovers don't want to go that far, They like dressing up but after they get out of bed they want to be boys again. I'm looking for a she-boy that wants to be a transsexual like the girl in the movie." I didn't say anything, as I wasn't sure I wanted to go that far. It was fun dressing up for Stan and I know I would anytime he asked me too. I also knew I liked sucking his cock and I loved having his finger up my ass, but I wasn't sure I wanted to be a girl all the time. If I had breasts then I would have to dress like a girl all the time. Besides how do you get breasts anyway? Stan must have understood my trepidation as he said, "Come on honey let's go up to the bedroom so I can return some of the pleasure you gave me." I stood up to let Stan up and as I did so I bent over to pick up the robe that I had worn earlier. As I did so I felt Stan's hands on my bottom and then I felt his lips on my cheeks. I knew then that he was going to fuck me when we got upstairs. I shivered from the thought of his big cock going into me. Stan must have known what was going through my mind. Stan stood up and hugged me to him before saying, "Relax honey I'm not going to take you tonight. The first time I make love to you that way I want it to be special. I want you to want it as much as I want it. I don't want you experiencing any pain with our lovemaking. I want you to remember it as a wonderful and loving experience." That really made me feel better. I turned in Stan's arms and kissed him. We then went upstairs to the bedroom. Once inside Stan took off his pants and lay on the bed. I went around to the other side and as I passed the makeup table I took a quick look at my face. I saw that the lipstick I had put on was now completely gone. It took the tube from my pocket and reapplied it to my lips. As I did so I heard Stan chuckle. When I asked his what was so funny he said, "Nothing sweetie. You just did what any self-respecting women would do. Now come here." I slipped off my robe and lay on the bed in Stan's arms. I don't know why I bothered putting on the lipstick seeing Stan had kissed it all off. We kissed for a long time before Stan moved down to my neck. He kissed and licked my neck before taking off my chemise. He then licked and sucked on my chest and even on my tiny nipples. I really enjoyed it when he sucked on my nipples. It made me want to have big breasts for him to suck on. He then moved down to my tummy, he licked and kissed it before moving down to my pelvis. At first I thought he was going to remove my panties but he just pulled them down and licked all around my dick. I was still quite hard, as I had been most of the night. I really didn't think he would suck my dick but Stan surprised me by taking my dick into his mouth. This was the first time I ever had any one do this and the feeling of his warm wet mouth was too much for me. I barely told him I was going to cum when I started squirting my sperm into his mouth. Stan didn't miss a beat as he sucked down all my juices and sucked on my dick for more. Seeing I just came I thought Stan would stop but he continued to suck me for another few minutes. I thought I would shrivel to nothingness but Stan kept my dick hard. Once he knew I wouldn't go soft he moved lower and started licking my balls. He lavished my balls for a few minutes before he turned me over on to my tummy. Stan licked and kissed the cheeks of my bottom till I thought he had touched ever inch of skin back there. He then started to lick the crack of my ass. I never knew anything could be so wonderful. Stan's tongue slipped into my crack and he moved up and down. Each time he changed directions he went a little deeper. I'm sure Stan knew the pleasure he was giving me as I whimpered on every pass. When I felt the strip of cloth being pulled from between my cheeks I knew Stan was going to lick my hole like the guy in the movie did. At first I was worried I wasn't clean enough back there, but the second his tongue touched my hole I didn't care any longer. Stan licked my hole for several minutes then I felt his tongue push at my hole as if he was trying to push it in me. That was what Stan was trying to do. As his tongue penetrated me the first time I squealed like a girl. It was amazing and stars popped before my eyes. I honestly felt like I was going to cum again. Stan tongue fucked my hole for a long time till his tongue grew tired and he had to stop. He then straddled my legs and his cock rested between my cheeks. To tell the truth if he wanted to push his cock into me at that point I wouldn't have stopped him. Stan merely humped my ass as he reached into the nightstand. He pulled out a transparent blue bottle and what looked like a small cock. He then moved back down and I felt cool liquid being poured on to my asshole. Once he worked the lubricant into my hole I felt something blunt at the entrance I though he had changed his mind about fucking me till I heard him say. "Relax baby I'm going to use this dildo on you to so you know what it feels like. I'm going to leave it in you so we can train your pussy. This way when we're ready to make love for the first time you'll only feel the pleasure and not the pain." I felt Stan work the dildo into me until I felt the head of it pass by my opening. It hurt a little but Stan was very gentle. Once the head was in I felt him push in a few more inches. He worked the dildo in and out for a few minutes then I felt him push it in a little more. I was surprised at how much I enjoyed the dildo. I thought it was a shame it wasn't Stan's cock that was fucking me. But I also knew I could never take Stan's cock I wasn't that big back there. Stan worked the dildo in and out of me for several minutes. Ever few minutes he would push more into me. Each time he pushed in more it felt like it was getting wider. When he push in the lasted of it I felt like I was open up a mile. When my hole closed around the base I thought he had pushed it in too far until I felt the wide flange that was still out side my hole. Once he had it in me he patted my bottom and asked if I was all right. "Yes," I said, "but I feel so full. Like I have to go to the bathroom." Stan kissed the nape of my neck and said, "You'll get use to it. Believe me this will help. Now turn over." I flipped over onto my back and Stan got between my legs. He then lifted my legs and put my feet over his shoulders. With his hard cock resting on my smaller one he squeezed my thighs together with his cock between them. He then started to thrust his cock between my thighs. At first I wasn't sure what he was doing but once his cock started rubbing against mine with only the thin satin panties between us I didn't care. His cock moved back and forth rapidly and in no time I was sinking into the blissful feeling of my impending orgasm. Stan wasn't far behind, as he started grunting each time he pushed forward. A few seconds later I was filling my panties once more. A moment or two later I felt hot thick ropes of Stan's cum land on my chest and stomach. Stan released my legs and they fell to his sides he then leaned over and kiss me passionately. When our kiss ended he said, "It looks like I made a mess of you again. Let's go hit the shower before bed." As Stan went to turn on the shower I removed what clothes I was still wearing, I then joined him in the shower where we kissed and hugged each other till the water turned cold. We dried each other off before going back into the bedroom. As Stan climbed into bed naked I went into the closet and put on a long sheath type nightgown. Once I was in bed we kissed then Stan placed my head on his chest where I fell asleep. When I woke up the next morning Stan was in bed with me. He was nibbling on my ear and I'm sure that's what woke me up. When he saw I was awake he said, "Time to get up love. Breakfast is ready and we need to talk before you leave. Now don't change and don't take out your butt plug unless you have to go to the bathroom. If you do, I want you to put it back in when you're done." Stan kissed me then left the room. Thankfully I didn't have to go the bathroom that way so I didn't need to take the butt plug out just yet. After peeing I washed my face and hands then went back into the bedroom. Just to let Stan know I was serious about being a girl for him I decided to put on some makeup. Like the night before I put on mascara and blush before coating my lips with a pale red lipstick. I then found some tan fuzzy slippers in the closet that went well with the tan nightgown I was wearing. I went down to the kitchen where I found Stan sitting at the table. I'm pretty sure he noticed that I had put on makeup as he smiled when he looked at my face. As I sat down next to him he leaned over and gave me a kiss on the cheek. We ate breakfast together and when we were done Stan said, "Do you have a name you like. A girl's name you would like to be called?" I thought about it for a few minutes, I remember a girl I knew in grammar school. Her name was Sara and she was the only girl that didn't treat me like I was her kid brother. I told this to Stan and he said, "From now on I'll call you Sara. Seeing the way you're dressed I can't call you Scott any longer." I actually blushed when he said this. Stan then reached below the table and came up with a bag. It was a plain brown bag like the ones you get at the grocery store. Stan placed the bag in front of me and said, "I want you to take this home with you. Inside you'll find several pairs of panties a new bottle of anal lube and another butt plug. I want you to wear the panties as often as you can with out getting into trouble. I don't want you wearing them when there a chance you will be found out. "As for the butt plug I want you to put it in as often as you can and when you think you can handle it I want you to switch to the larger one. This will prepare you for the first time I make love to you," Stan told me as he slid the bag closer to me. Stan then took a key out of his pocket and slid that over to me and said. I'm going to be gone for two weeks. I would like it if you would come by and check on things. While you're here I want you to dress as if I was here and stay that way until you leave. You can do what ever you like as long as you're dressed like a girl." I don't remember ever feeling as sad as I did at that moment. Stan must have seen the sadness in my eyes. He took my hand and said, "I'm sorry honey but I made these plans before we became lovers. I would cancel them and be here next week but I really can't. I do have a business to run. I have to leave shortly as I have to get back to the city and pack. Can you take care of the dishes if it's not a bother?" How could I possibly say any thing but yes?" Stan came over to me and kissed me deeply for a few minutes before he left the house. I stood at the window as I watched him drive away. The sadness I felt earlier became worse once his car was out of sight. After I consoled myself for a few minutes I went back to the dinning room and took the breakfast plat