A Man and His Breasts -or- How I Got Boobs

  As far back as I can remember, I wanted to be a girl. My earliest memories are of watching my Mom putting on her makeup for Church. I loved watching as she applied blush, shadow, mascara and my favorite, lipstick! My Mother was a beautiful woman, she dressed well, always wore makeup and kept her nails perfect. The other things I adored were her high heels. They made her look so pretty and I wanted to wear them so badly I ached. When I was old enough to wash myself for bedtime, probably 4 or 5, I started trying out some of Mom's makeup. By some, I mean ALL of her lipstick! Mascara and eye shadow were difficult to apply and hard to clean up. Besides, I LOVE lipstick! Mom had lots of tubes of it and I would take one with me when I went to clean up. At first, I couldn't get it right, but I slowly got better. It was kinda hard to clean up, but I was careful. At least, I thought I was. One day, after trying a bright red lipstick, I missed a bit when I cleaned up. I came out of the bath, put on my PJs and asked Mom for a snack. She said sure and asked me what I wanted. When she looked at me, she immediately asked what was on my face. Nothing, I said. Then she stepped closer to look and stepped back. "That's lipstick!" she said. "How did that get there?" she asked. After pretending to misunderstand, a tactic I used all my life to buy a few seconds to think up a story, she repeated herself. "How did lipstick get on your lips?" I was in a panic as I said "I don't know." This was probably my first, but definately not last, real jam I had gotten into and my escape mechanisms were not yet developed very well. Just then my Dad came up the stairs, looked at me and Mom and asked what was going on. My Mom told him she caught me wearing her lipstick. My Dad turned to me, "Are you a girl?" he asked. "No" I squeaked. "Well only girls wear lipstick, so you MUST be a girl. Are you sure?" He turned to Mom and said, "Why don't you and Scotti go to the store and buy a dress for her to wear to school tomorrow? Would you like that, Scotti?" Me eyes burned with tears as I screamed "No, I'm NOT a girl" and ran to my room, sobbing. I lay on my bed crying, scared they would dress me up like a girl ad take me to school like that. It would be so humiliating and everybody would be laughing at me. It was then it happenned. My little wiener had become stiff as a board! I didn't know what was happenning to me! It was twice as long as usual and as rigid as a steel rod. I didn't know what to do. Was I going to die? flashed through my mind. And then it started to go down. I could here my Mom approaching my room, so I pulled a blanket over my body. She came in and talked to me. She told me I wasn't going to school in a dress and that my Dad was just trying to scare me. She put me to bed and it was never mentioned again. I stopped messing with her makeup and life went on. After a couple of weeks, the urge came back, stronger than before. I loved everything about makeup, her high heels and even perfume. I used her makeup more carefully and not as often as I did. I think my Mom knew I was using it. She and I became closer and she coddled me somewhat. She died of cancer when I was 12 years old. At the time I needed her most. I was crushed and went into a shell. I lay in my bed, sleeping. My Dad had to travel for his job and was often gone for days and even weeks. My brothers were 14 and 6 at the time and my Dad would leave us to take care of ourselves when he had to be gone. He left us money, food and washed all our clothes before leaving and we were just fine. He called every night at 6:00 and made sure everything was O.K. At this time, my brothers went somewhere, I can't remember where, but the bottom line was I would be alone at home all day long, at least until 7 PM. After they were picked up, I went to my Mom and Dad's room. Her closet was untouched as were her dresser and makeup table. I looked through the dresses on hangers, her shoes and bouses. The dresser was full of bras and panties. Also, somethings I wasn't sure of that turned out to be 3 corset and garter sets, black, white and red. There were stockings and panty hose in many colors and styles. And in the back, under some sleepwear, was a long, slim box. I pulled it out and opened it. To my shock, it was a foot long, rubber penis! It was a dildo, but I didn't know that at the time. I put it back in the box and buried it where it was. Moving on, her makeup table was well stocked and even included dozens of bottles of nail polish in every color you can imagine! By the time I regained my senses, it was 10 AM. I didn't think about crossdressing at first. I wanted to try the high heels most of all and using ALL the cosmetics she use to wear. I got a pair of 4" heels and found they fit perfect! I was only 12 and my feet and whole body was still that of a young pre-teen.  I tried the heels on and although they fit well, there was no way I could walk in them! I couldn't manage 2 steps in any direction. After almost breaking an ankle, I took them off and put them back, telling myself I would never be able walk in them. I could not understand HOW women walk so gracefully in heels even higher than these. I wrote it off as impossible and didn't think about them for a while. Next, it was her dresser. Her panties fit me nicely and there were more colors and styles than I knew existed. I pick a pair of pretty pink panties and black panty hose. I retrieved a pair of 1 inch heel mule slippers to wear so I wouldn't damage the stockings. I wasn't very graceful, but I could walk in them and besides, they are really cute! I had almost no body hair, with a little light fuzz on my arms. First, I slid the panties on, loving the sensation as the silk cupped my small, hairless cock. It goes without saying that by now my cock was as big and hard as it had ever been. But when I carefully slid my slim legs into the black panty hose, I was on the verge of climax. I didn't touch my penis because I was so excited. An older boy had told me about 'cumming', but I had not yet orgasmed. All I had to do was stroke my penis, he had told me. Just keep on stroking it until you get a REALLY good feeling and your cum will spurt out, all by itself. You'll know it when it happens, he said. My little noodle, even at the biggest it's ever been, was only 4" long and not thick at all. I assumed that was about average. I would find out what assuming did for me a bit later. 

                                               The end opf part 1