At the ripe old age of 10 I was walking home from school and saw the most incredible thing. At least, at the time, I thought it was pretty incredible. The whole incident began by me hearing a 15 year old boy quietly talking to himself in a patio in a vacant house. He was saying, "Come on, come on, oh yeah, I know your coming out of there". He got my attention and I admit I was curious.
I couldn’t see who he was talking to and he was standing with his back toward me. He turned around and what I saw caused me to become very interested. I squatted down behind a small bush, I didn’t make any noise and I don’t think he saw me. As I squatted I could clearly see him. My mouth was uncontrollably dropped open and I began to drool! No body had ever done that to me before.
I stayed behind my little bush and watched him. My breath was ragged and fast, my blood pounded in my head and my heart was beating a mile a minute. I couldn’t believe just looking at a boy’s private part could make me react this way! He sat down on a dead tree in the “garden” of the patio pulling on his cock with some varied rhythm. His cock was absolutely beautiful. It was way bigger than mine and white as can be. All the time he kept stroking and talking, stroking and talking. He had his eyes closed so I'm sure he didn't know I was watching him. I was actually staring at his hard-on and my drool ran uncivilly down the front of my shirt!
All at once, he said, “Oh God, yes!”
He closed his eyes tight, smiled up to no-one, and let out a big sigh of relief. I watched in great surprise as he shot all kinds of white stuff out onto the ground. He shot then paused, then discharged some more, then paused and discharged still more. His cream was every where! He slowed jacking off and finally stopped. His cock was still stiff and he flexed it. More white stuff seeped out of the head. From where I was hiding I couldn't tell much more than that but I could see his huge prick very easily. It was enormous and standing straight up. He took out a smoke and lit it up.
When his cock got soft he put it back in his jeans. When he passed me he looked surprised as he looked down at me, I didn't dare move, he was much bigger than I was, and he asked what did I see? I looked directly into his bulging crotch and told him I saw nothing. He said, “That’s good, little boy!” as he lit another cigarette and walked away. When he was gone I went into the patio to see the creamy stuff on the ground for myself. I stuck my finger in it and it felt sticky. It had no odor and it had no taste. Yes, I licked it off my finger! I left the patio and went home.
I never played with myself before but after what I saw I was anxious to give it a try. Later that night I tried it in my bed. I made certain my covers were up around my neck and took my shorts down. I put my tiny penis between my thumb and index finger and began to jack off. As I ejaculated on myself I must have made some happy sounds because my brother caught me doing it and told my mother. I got into a lot of trouble that night. She made me sit in a corner for a week after school rather than let me go out to play. During this time I just kept envisioning Jimmy, I could see him really clear especially the joy he showed when he finished. I now knew that same feeling.
Maybe the woods was the place to go. I'd check that out after I was off restriction.
I talked about jacking off with my friends at school in the play yard, but they weren't interested. Obviously they hadn’t done that yet. So my desire to do it just got worse. Then one day I found myself in the woods alone. I got the nerve to take my tiny dick out and began playing with it. I finally got myself hard but I was still kind of small. Another boy showed up and asked me what was I doing, I told him. He laughed at me. He told me I was doing it wrong. I didn't know there was a right way! He told me to kneel down and watch him, and learn. I did as he told me. He took his cock out and showed it to me with pride, it was much bigger than mine, and I was fully erect and he wasn't even hard yet. I was trans-fixed on it. Hypnotized almost.
He began to pull on it real slow and all the time he was telling me how he did it, slow at first and then getting faster and faster, until he was ready to "shoot". I knew exactly what he was talking about, but I asked him to explain it to me. He said he'd do better than that, he’d show me. I kept watching him move his hand along the shaft of his cock, up and down, going faster then going slow. Then he told me to move in real close and I'd see some creamy white stuff come out of the little hole in the end of his dick. He said I needed to be real close, I moved in. And he "shot"!
My immediate response was to block it but it was warm and kind of salty and it happened so fast! It had no real feel on my face and only a strange and unfamiliar taste but it was not offensive. All my sensations were searching for these things but I couldn’t find any so I took it. It smelled strong of musk, but it was not unpleasant. I was just kneeling in front of him and what I couldn’t get into my mouth was a cum mess all over my face. He finally said "I'm sorry.", but he was laughing at the same time.
As I watched him drip semen from his erect penis he asked me how it felt spurting onto my face? I told him what I felt. I added it was kind of slippery, too. I may have even told him I liked it. As it made it’s way to my lips he told me to lick it. I saw no reason why I shouldn’t, so I did. I only tasted a tiny bit of it and it tasted like chicken fat. He told me to use my finger to wipe it all into my mouth, he watched me do it. Then he said, “Ya know what? You should walk home with me.” I did.
Once we got to his house he told me to wait in the kitchen, he then got some magazines from his mother’s bedroom and showed them to me. They were filled with full page color pictures of women sucking men's cock. He said his mother hid them. He said it was no big thing and anybody could do that if they wanted. He told me it didn't matter if the person sucking wasn't a women or not, he said, “You just have to want to do it, that's all.” Then he asked me, “Would you like to do that with me?” I told him maybe. I said it was getting late and I had to go home. He said I could take a magazine with me, but I'd have to come back tomorrow and give it back. Maybe we could look at them again, together. I said that was OK with me, I tucked the magazine under my shirt and I left.
On the way home I stopped and looked at the magazine. The women were all made up and looked pretty, sexy I thought. They wore pretty underwear. They looked nice all dressed up in skimpy but pretty panties, garter belts, really high heels, shinny bras and seamed nylon stockings. Very sexy, yet very feminine. What they were doing with the men looked quite natural. Most of the women looked as if they were actually enjoying themselves. The men weren't visible, except for their dicks, so I didn’t really see much of them except for their huge hard ons, which were gigantic! Strangely enough, seeing their penis was very attractive to me and I felt a wetness in my underpants.
The women were shown in either full close up facial shots, or full length pictures from different angles. I’m guessing they were posed that way so you could see what they were doing and learn how they did it. The whole magazine seemed like a “How to” manual. I don’t think I’ll ever get over how natural it seemed to see women with their mouths filled with men’s hard ons. I found myself desiring the white cream the men would shoot. It wasn’t shown in the magazine but it was clearly a craving in my mind!
Jimmy told me to take the magazine to the bathroom for a long visit. He told me to go there and jack off in the toilet. He said that way I wouldn't get caught by my brother. He was right. I shot out some stuff, but not near as much as he did. It wasn't strong smelling but it felt great! I couldn't wait to tell him about it. The next day I went to his house and we talked about my bathroom experience. He said not to worry about the amount I shot because I’d make lots more of it the more I did it. He also said it would get stronger smelling too. He recommend that I jack off in my empty hand so I could lick it up. He said I should tell him if I liked doing that.
Then we sat on the couch and he told me to show him how I did it. I eagerly pulled my pants down and pulled my tiny dick out when he stopped me and told me to use his cock. He took his pants down and took it out, I couldn’t take my eyes off of it. When he took it out and told me to put it in my hands, I just did. I began talking my way through it and began using his cock to show him. Then I realized what he was doing! He was teaching me. He told me to move my hand slow then fast, grab it soft then hard, do the length then “wash” the dick head. He smiled and said, “Damn. You don’t need much practice because you’re already pretty good at it.” I felt good about that and said I would practice on him any time he wanted, I told him how he was much bigger than me anyway. He just smiled and said nothing. His cock became so big and so hard I wanted to cry! Soon he told me it was coming, this time I was disappointed but ready. I picked up a nearby magazine and held it in front of his dick and said he could shoot on it!
He told me to take the magazine out of the way and just open my mouth. He said I was a naturally queer bitch. I was kind of surprised but did what he said. He inserted his dick head into my mouth and told me to be still. He was jerking himself off now, my hands were on the sofa positioned just out side of his legs. His hand was going very fast along the shaft of his cock. I held his whole dick head and suddenly, I could taste his semen. He kept telling me to swallow it and I did my best. I took almost all of it, it wasn't bad at all. It tasted just like chicken fat but a little salty, otherwise it was warm and OK.
He said I did good for a little boy and lifted me up off my knees. He gave me a cigarette and I choked on it. We both smoked. When I was leaving his house to go home he told me he liked me a lot. He smiled and said. “Maybe you could be just like those women in the magazines, we could have a lot of nasty fun!” I looked at the ground and told him, “I’m sorry I’m not a real woman for you but if I was I would be pleased to be yours and I just know we would have lots of fun.” He put his arm around me and told me not to worry, maybe we could just pretend. I said that would be good for me, but I also told him I didn't know how we could do that. He just smiled and said he'd think of a way.
I was so young I had no idea what he was asking of me, I didn't see where he was leading me. At the time it was just something new I wanted, he was just some guy who was teaching me. I was a very good student, eager to learn and even more eager to please. I was fully accepting that I was becoming a woman, his woman. Sexually speaking, I made up my mind I was going to be a woman for the rest of my life. I would often go to him and do my best to prove it.
He introduced me to an older man named Ralph one day, and said Ralph liked little boys a lot but he looked gruff. Jimmy said I didn’t have to be afraid of him, though. When I was introduced I wasn’t afraid of this man at all because he was a friend of my family’s! He worked for my father! We had a few days of play which turned into a few overnight weekends and had much fun. He would tickle me and touch me in my private places and tell me to touch him. I would stop playing and remind him that touching was not part of our game. He asked if I was insulted or embarrassed by his touching me, or my touching him, and I said I was not offended and only mildly embarrassed. We laughed. Soon we began to play in our underwear and we touched each other more and more. For the most part, I welcomed him touching me and I especially liked touching him.
One day, he sat me on his couch and told me he was going to do something special for me and that I should close my eyes. I got very excited and did as he told me and then told him I was ready! I felt him sit next to me on the couch and he put his hand on my thigh and kissed me full on the mouth. I opened my eyes because I felt his beard stubble scrape my face. He kissed me for a long time and he didn’t use his tongue. I got such a strong and wonderful feeling I began to like it and closed my eyes and responded. It was so strange, the only way I can think of to describe it was that I think I may have melted! I never got that feeling from any other man since and I loved him for doing that for me.
He said it was time I become his little woman, that’s when my cross dressing began.
I wanted to tell Jimmy how wonderful it had become for Ralph and me but Jimmy didn't show up for school for the rest of that year. I didn't know where he went so I asked his folks. They said he was visiting some relative in Oregon. An older friend of mine, who was also a very good friend of Jimmy’s and knew quite a bit about him and his history with me, told me he thought Jimmy was sent to juvenile hall for being beyond parental control and cutting school. I never saw him or Jimmy again.
I began to see Ralph more and more, I liked him. He bought all my foundations and make-up, my panties, my camisoles, my dresses and slips, even my heels and stockings, everything. He let me be feminine and taught me how to look like a woman which felt great. He began to take photos of me, I never looked so good! I can’t explain it but I wanted to go beyond just looks with him. Sex finally was in season. We graduated and more than just a few pictures became extremely graphic and very compromising. I enjoyed being a part of his photographs.
But it was my wanting photos of us that would bring us into court!