Chapter 1: What I remember

All I know is what I have been told about my early life. I am the youngest in my family of seven children and the only boy. My sisters are about 18 months apart and are Margaret, Catherine, Ann, Sara, Mary and Joan, my name is Matt, short for Matthew. I was born in 1966. I grew up in a small, middle class southern town. When I could remember, I remember I did not have a father. My mother did not talk about my father just that he left, and that was that. My family was my sisters, my mother and her sister. My mother worked as the administrator of a small hospital where we lived. She provided well for our family. My aunt worked in real estate and helped to pay the utility bills and provide for some of the extras that a family needed.

As a boy my first memory was standing in the bathtub. I must have been four years old, my youngest sister Joan was around six. We were standing in the tube waiting for the bubble bath to bubble up. I was standing there naked with my wee-wee showing. I remember seeing my wee-wee causing me to noticed I had one and Joan did not have a wee-wee. Noticing the difference, I asked my mommy why. She told my I was a boy and boys had wee-wees and girls did not. That is all she said on the subject. I tucked my wee-wee between my legs trying to look like Joan. I told my mommy that I was a girl, Joan giggled, mommy laughed and so did I. I did the tucking trick a lot. When I was naked and one of my sisters could see me, I would tuck and pretend to be a girl. I wanted to be like them. All my sisters got a big laugh out of my tucking trick.

They would say, "Oh I see your wee-wee." I would turn around tuck my wee-wee between my legs and then show that I was like them. I would say, "Look I am a girl" and I would prance round rivaling my sister.

My next memory was my Aunt yelling at me for leaving the toilet set up. I do not remember who taught me to pee standing up like most boys. Like most boys, I did not pay attention where the pee was going and sometime missed the pot. I did not remember ever told to put the lid down after every use. I guess one morning my aunt went to the bathroom and sat on the porcelain rim understandably she was upset. To preserve the peace in the house, my mommy told me to always to sit down to pee. She thought this would be the best way to make sure that it did not happen again. That little advise was surly useful because I did not have to worry about leaving the toilet seat up, I still do not know what the big deal about the toilet seat. Half the time it is up or halt it is down, I have to lift it up to pee, it is just as easy to have her lower it to pee. Today when I go to a public rest room, I use the stalls and not the urinal.

Sunday was laundry day, and I remember watching my mother fold all the clothes of my five sisters. I remember seeing white panties, pink panties, white bra and some colorful bra and panties that belong to my aunt. When my mother was not watching I would fall into the fresh out of the dryer clothing and felt the warmth surrounding me the smell of clean clothes. I would feel the silky touch of my aunt's undergarments. The warmth of the clothes felt like when my mother would hold me in her arms, and I felt safe and secure.

My family was large leading to some challenges growing up. Every year our clothes passed to the next younger child, from one sister to sister to me. For the first years of my life, what I got was Joan's clothing, panties, her girl jeans and tee shirts in pink, purple or green. From an early age, I wore hand-me-down girl's underwear. I was so young I did know the difference in the underwear. From that time I sat down to pee not need the opening that boys underwear had. The panties were the standard white cotton panties with bows. Some of the panties were pink dyed from being washed with something red. Wearing pink girls' panties was never an issue in kindergarten. No one noticed, if someone did, I do not remember anyone making an issue.

Because my family was all females except for me they were not modest in front of me. The bathroom door remained open unless when one of the girls was getting ready for a date. My older sisters would spend hours in the bathroom making the rest of us wait until they were pretty for their date. Therefore, I have visions of my sisters in various state of dressed and undressed and grew up seeing my sisters' pre and post publicly. I started to notice my sisters' breasts when I started the first grade, my oldest sister Margaret was fifteen. I was walking down the hall the door to the bathroom was open, naturally, and I looked in. Margaret my oldest sister was standing in front of the mirror looking at her breasts. I watched as she put on her bra, backwards and twisted it around slipping her arms through the straps and adjusting each breast. I remembered each year before the start of the school the big event would be one of my sisters would be given her first training bra. Ann who was about 12 received her first training bra. It was a big deal for Ann resulting in her giggling all-day. I remember thinking that when I was older, I too would receive a training bra also.

I remember having long curly hair like my sisters. Before going to school it was all shaved off making me look like a boy for the first time. I cried that night because I missed my shoulder length hair that made me look like my sisters, now I did not look like them ... When I was in first grade Margaret my oldest sister was starting to use make up. I would sit there watching her take this brush and put it on the eyes and that tube on her lips and would see my sister transformed into a young beautiful woman. She would play a game with me and put lipstick on me, and I would go around the house displaying to my sisters that I was like Margaret and making faces and sticking my tongue out. Margaret once did my entire face, and I looked like a raggedy Andy doll with bright red cheeks. My sisters, mother and auntie all laughed at my outlandish make up.

As a boy, I did not realize there were two genders. There was no man around the house. I did not know to stand like a man to pee but sat like my sisters. I laughed like them in a girly giggle. I pranced round like them walking and swaying my hips. I hid my wee-wee from my sister's site because I wanted to be like them. I adored my older sisters and wanted to be look them, walk like them, talk like them.

I had long curly hair when I was young. In our early family portraits, you could not tell I was a boy. As in life, everything changes. Prior I started first grade my mother took me to the barbershop and had cut off my curls. I cried that night because I did not look like my sisters. When I started first grade I was still wearing Joan's hand-me-down panties and girl jeans, which zipped differently the other boy's jeans. I was not aware of the different in how girl's jeans and boy jeans fasten. My feet were bigger than my sisters, and with no hand me downs to fit my mother had to buy me boy's shoes.

I remember when Mary got her first period and how embarrassed she was to have stained her panties. I overheard mommy tell Mary this was normal with and women will bleed. Mommy said it was a curse, but it allowed you someday to be a mother, so it is worth the trouble. Mary was coached how to use a pad and told to carry pads when it was her time of the month. I now realized why my sisters carried purses.

When I was in first grade at playtime I did what was comfortable, playing with girls. I played hopscotch, did the jump rope, and the hand clapping and chanting with the girls. I had the chance to play softball, tag, or other boy's games, but I preferred to sit with the girls and watch. When I did play softball, I toss the ball like a sissy and everyone laughed. The older I grew the more aware I became and how different I was from the other boys. I did not talk like a them; I did not walk like a them. My clothing was different the other boys. I remember telling my mother when I was in third grade that I was differed from the other boys because I was not dressed like them. My mother took me out shopping for my first boy jeans, but I still wore girl's panties.

Going into the fourth grade, I was teased by the boys for playing with girls. It did not take me long to understand it was better not to play the girls. I was uncomfortable playing on the boys. I still felt like a girl inside but had to learn to pretend to be a boy. When I pretend to be a boy the teasing was reduced. Starting the fourth grade, I found my best friend, Billy an older boy who repeated a grade, so he was a year older. Billy's reading was not good causing him to have to repeat the fourth grade. He was new at our school, and I was alone; we became friends. I was ten and Billy was 11 and half. Another reason we became friends, Billy protected me from the others because the way I talked and acted. I helped Billy to read. What I did was to read to him, so he could answer the questions in class the next day. Every day-after school we would spend time playing in the woods in an undeveloped part of town. We found a pond and sat there in the early spring reading about history and science. The first day in the woods, Billy said he needed to take a leak; I did not know what this meant as Billy stood up and walked to a tree. He was in plain sight, and I watched him pee on the tree. I never saw man or boy do that before, and it is something I remember to this day. Billy asked me if I needed to take a leak, I said no. The next-day Billy took a leak and asked me if I had to take a leak. This time I decided to do what Billy did. It was a great feeling to stand and pees like a man. It feeling was wonderful. We both stood there pissing on the same tree, our streams crossing. Billy bet me he could pee higher on the tree than me. Billy won because he was taller than I was.

It was when I was standing next to Billy peeing, Billy noted that my underpants were pink and did not have the opening where you would slide your wee-wee through to pee. I lowered my panties, holding them below my balls to pee. When we finished, peeing Billy asked to see my underpants and not know why, but without hesitation, I dropped my jeans to reveal my panties with lace around the legs and the waist. Billy showed me his underwear, for the first time I realized there is a difference. I joked with Billy and said that if he wanted I could give him a pair of panties, and he could look like me. We both laugh over the joke. The next-day Billy gave me a paper bag with some of his old underwear. I was excited to receive boy underpants and pleased to be dressed like him. I had five boy underpants which I wore during the week and had to wear pink girl's panties on the weekend.

Billy noted that I tossed the ball like my sisters. One day down by the pond, he bought two gloves and a baseball. We spent the afternoon playing catch; it was not long that I had a good arm throwing the ball.

In the woods, we did guy things; played cowboy and Indians, cop and robbers and army. I made sure that we did our reading assignments, so Billy would not get in trouble at school. We even skinny-dipped in the pond where the water was cold. When we got out of the water, I remember that our wee-wee, and balls would shrink. I did notice that Billy's cock and balls were larger than mine. Then as we lie beneath the sun drying off allow our wee-wee to return to normal size. Billy being about 18 months older than me was taller than I was. He started to have some pubic hair start growing on the top and sides of his wee-wee.

Being older Billy had and a sex discussion with his father, and he shared some of the sex details with me. I did not understand all that he told me, especially about how the wee-wee would slip inside the girl and nine months later; she has a baby. Billy had an older brother and no sisters. I told Billy all I knew about my sisters, how I saw them naked and knew that they had a period every month. Between the two of us, we had a good understand the difference between a girl and a boy.

I was in the fifth grade, eleven years old when I woke up and thought I had wet the bed because I was wet between my legs and there was a wet spot on the sheet. I must have woken my mother up; she came to see what happen. She helped to clean me and change the sheets. I was embarrassed to ask my mother what happen and went back to sleep. The next night it happens again, and I asked my mother what was happening. She said I was growing up and that my body was changing. She said I had a wet dream. I got the sex speech that Billy had told me a year early. He left the part out about wet dreams. My mother had some advice for me. I needed to play with my wee-wee to make it squirt. Once I squirted I would feel claim and sleep without a wet dream. I tried that a few times, but it took a longtime to squirt.

The next morning at breakfast, I told my mother it took a longtime to squirt. My aunt was standing there and reached under her skirt, pulled off her black lace panties and tossed them to me. Her panties were warm, smelled of perfume and were silky with lace and bows. She said to rub this on your wee-wee, and I would come faster. I put the panties in my draw with my hand-me-down panties, next to my boy underwear and now my first pair of woman panties. My mother just looked at her sister with a look like, "why did you do that."

I thought of my aunt's panties all-day and could not wait to go to bed. That night as I lie on my bed, I wrapped my wee-wee in the silky panties and started to stroke my little wee-wee. It was an amazing feeling, much better than with my hand. In five minutes, I exploded in the panties keeping the mess contained and not wetting the sheets. The next morning I washed the panties out and hung them up in the shower just like my sisters. When I arrived home after school, I went into the bathroom to recover my frottage, but it was not there. I thought that one of my sisters took my panties, I was angry. I went to my room, open my drawer to find the panties folded, and place next to my other panties and there was a second pair just like the fist but black.

I went to bed early just so I could squirt and feel so relaxed. I had loads of squirt in the panties. Instead of waiting to wash them in the morning, I did it that night. The next morning they were dry, returning to my drawer.

If the weather was bad, we went to Billy's house or to the library. It was a few days after my first wet dream, I told Billy about it. I told him what my mother told me to do. Billy got a smiled telling me he had been rubbing off for more than a year. He asked if I wanted to see his brothers rub off magazines. I said sure. We went to his brother room and under the bed were several magazines such as Hustler. The pictures were pornographic and graphic. I now could see what a pussy looked like. Until, I saw my sister's pussy was a slit and their pubic hair. Now I saw everything in detail. We sat upon the floor looking at every picture and every advertisement for sex.

Billy was rubbing his crotch looking through the photos; I was aware I was hard and felt the need to rub my wee-wee. I had seen Billy's cock many times in the woods when we pissed or when swimming. Billy said, "You have a wee-wee because you are small. I have a cock because I am big." I felt to embarrass because he kept referring to my wee-wee as small wee-wee or little wee-wee. We sat looking through the magazine commenting on the size of these breasts and looking at their pussy. Billy unzipped his pants pulling out his cock. I was surprise; Billy's cock was erect and huge. It was three times as large as mine and thick. I measure my wee-wee once, and it was one inch when I was ten, two inches when I was eleven. One day I hoped to be as large as Billy. I did not mean to stare, but I found his cock being amazing. I noticed the tip of his cock was bright pink. He said he was "circumcised." Billy said that some boys had the extra skin that slides over the end of their cock. And they were "uncut." He said that Jewish boys when they are thirteen, would have the extra skin would be cut off. We looked at each other and said "ohooooo" at the same time. I took out my little wee-wee, felt a little ashamed but Billy said that in a year, I would be as big as him. As we looked at the pictures, Billy rubbed his cock, I rubbed my wee-wee. I watched Billy touching his cock; I would do the same with my wee-wee. I was playing copycat to his every move. He started to squirt. He squirted a long squirt of white liquid a good three feet landed on my arm. It felt warm, wet and was sticky gooey. The next squirt was off to one side and landed on my leg; the third squirt did not go as far and landed on my foot. The sight of seeing Billy squirt was so erotic that I squirt also. My liquid shot all over the hustler magazine, causing Billy to say "shit." He jumped up and found some tissues cleaning up the mess. The one picture was ruined; Billy tore it out of the magazine. He gave it to me and told me to toss it out on my way home. We cleaned up the room, our mess and went to Billy's room. We did not say much about what we did in his brother's room. I read to him the next day's reading assignment.

That night I reached inside my pocket and pulled out the hustler picture that I was to toss. I had panties and a picture to help me rub off. I could squirt quickly. At first, it had taken me over a 15 min to squirt. Now with the photo and panties, I could squirt into my silken panties in two minutes.

The weather was bad the next day as we ended at Billy's house and in his brother room looking at the rub off magazines. This time one magazine called SheMale and had a photo of a woman with cocks. This was confusing to me. Billy said some people were neither men nor woman but were SheMale. The pictures were exciting and still confusing. The SheMale did not have a slit like a woman just a cock and balls with big breasts. Billy started to rub his cock. I started to rub mine. I notice that his cock was all shiny and that some white fluid was dripping out of his pee hole. He said it was pre-cum, and that he used it to make his cock slick. Being younger, I did not have any pre-cum yet. Sensing that I needed something to help my wee-wee slick; Billy said I could have some of his. He moved closer as I held out my hand. Billy squeezed a drop or two of pre-cum out of his cock. I rubbed it on the head of my cock. With a few stokes, I started to squirt. Today I had a tissue so did not create a mess as I did the day before. The touch of Billy's pre-cum in my hand, and making my cock slick was sensuous. Billy giving me his pre-cum was something special. With his pre-cum, I could shoot. I connected Billy's pre-cum with my squirting. After I squirted quickly, Billy continues to rub sitting direct across from me. I did not think I was in the line of fire until he exploded, this time squirt was not on my leg, or arm. The first squirt hit my face; it was warm, wet and gooey. The second squirt was on my chin and neck. The third squirt on my chest. I was a surprise at how quick it happened. Billy was watching to see my reaction. Billy said he did not mean to squirt on my face and smiled. I remember the look in his eyes; it was the look of pleasure or satisfaction having hit my face. I smiled back with a look of acceptance and giggle like a girl. In a strange way, I felt I should be the one to receive Billy's squirt. We were the best friend and having him squirt his load on me was just a benefit of our friendship.

It was the weekend; all my boy underwear was dirty. I could wear my pink cotton panties or could try on my silk panties. I selected the black lace panties. They felt sensuous touching my wee-wee, my wee-wee sliding up and down inside my panties; my wee-wee was semi erect all the time. I knew I was aroused all the time and knew if I touch my wee-wee I would squirt quickly and would be rewarded with that pleasurable feeling. It was Saturday, I had finished my chores. I hurried over to Billy's house, so we could play again.

Billy greeted me with a big smile upon his face; we got a couple of Cokes out of the refrigerator and sat in the den. We were watching TV, nothing special, flicking the channel seeing if there was anything interesting to watch. It was Saturday and many cartoons but nothing interesting. Billy asked, "What do you want to do?'

I was hoping that we would go to his brother's room but did not want to suggest that quickly so said, "I do not know. What you want to do?"

Billy seemed to be hastate to suggest that we go into his brother room. When we were not in his brother's room looking through the magazines and playing with our cocks, Billy did not talk about what we did. It was as he was a different guy. When we were in his brother room and looking through the magazines, we always were rubbing. He would joke with me, would tell me fantasies about how it would feel to slide his cock in a real pussy. He would tease me and said, "Matt you have a tiny wee-wee it would never slide into a pussy. You are going to have to use your hand until you have a real cock."

I would laugh and say, "Oh Yea." This time when we started to rub our cocks I took off my pants to show Billy my black lace panties. He just stared at them and said, "Cool, cool, so cool." He even reached out and touched my panties to feel how smooth they were. I was sure this was the first time he every saw woman panties before, I smiled and was a little excited about showing off my secret. Billy looked at me dressed in black lace panties and asked me to take everything off but the panties. I had a white and thin body, not a boy shape but more on the feminine side. He said, "Matt you look very sexy; I want to come on you again."

I protested by saying, "Oh, that is yucky."

Billy replied, "Come on your little pussy; you can wipe it off. I want to see how far I can shoot and hit a target. Smile you are my target."

I could tell that Billy was not going to take no for an answer. His squirt would not be on my face long. I could wipe his cream off my face. It was something for me, I could not say no. Besides, I did not know why, but I wanted to see him squirt again. I wanted to watch him play with his cock and then wanted to see him squirt. I agreed, "OK, but only this one time, and I will wipe it off, OK."