This is a multiparty story from my childhood. It contains primarily bi/gay activity, as well as crossdressing and coming-of-age discovery. There are several chapters to follow, in which oral and anal sex eventually occur. I am grateful for my early experiences and would not change a thing. This is my first attempt at writing a story so I welcome constructive Feedback and questions. I enjoyed writing it!
The Early Origins of Jamie's Transformation Chapter 1
To hear my mother tell it, I was always "softer" than other boys. That was the word I remember her using when we talked about it. I was "softer." It was not a word I minded. It sounded nice to me. I liked the idea of being "soft."
I wasn't "sissy-acting" as some might imagine it. Other boys saw me as a boy, as did my teachers and other parents. In the first five or six years of my life, no one thought anything else. I was small for my age and my features were a bit more delicate, maybe, than other boys. I was certainly far less aggressive. Not rough-and-tumble like my friends. I was quiet and shy by nature. Mom described me as "sweet by nature."
I never thought of myself as anything other than what I was; a boy. I just knew that other boys were different in some way, and it was a way I admired. I liked that other boys were more aggressive. I suppose I was attracted to them in the way a girl might have beenÑattracted to their swagger, their energetic action and, even at that young age, a sort of bravado. I never felt looked down on by the boys I knew, but there was sort of a natural tendency for my friends to be protective toward me. They knew, instinctively, that I was not the one to stand up to a bully or to assert any sort of dominance over others.
My best friend at the time, a boy named Robert, stepped in more than once when other boys were taking advantage of me in some situationÑsome game or otherÑand I remember him saying, "Jamie isn't like you guys. Stop trying to push him around." I liked the feeling of him stepping in that way. Rather than feeling embarrassed by my own weakness, I remember feeling proud that there was a boy who would stand up for me that way. It seemed to me that was how things ought to be.
I don't remember much before the age of five or six, as I said. I do remember those things. Later discussions with my mother confirmed much of what I thought and felt about the way I was at that age.
I certainly don't remember sexual feelings then. At least not clearly. I remember a few times feeling something more than simple friendship for certain boys. A pit-of-the-stomach sort of warm feeling when certain boys would look at me or speak to me. I remember feeling something like that toward Robert as well. He was two years older than I.
I grew up without a father and without siblings. It was always just my mother and me. She was not a terribly social person, a homebody who rarely went out with men. She had a few female friends that she would see but not many. The two people we saw the most of was my Aunt Susan and my cousin Jenny. Like Robert, Beth was two years older than me. I remember being extremely jealous when she stayed with us for a few days once and I felt like she and Robert were better friends with each other than with me. If it was true at all, it would only have been natural. They were the same age.
But I didn't like feeling that he liked Jenny more than he did me. And I didn't like feeling that she liked him more than me. I was a kid, and like most kids, I wanted to be the center of attention.
My mother and I spent a lot of time with my aunt and cousin. They lived outside of the small town we were in, about a twenty-minute drive away. Me, my mom, my aunt, and my cousin. That was my family. A family of females with no male influence at all, for the most part. And I felt completely safe and comfortable in that world. Loved, and known. Supported and encouraged. I was a happy kid.
When I was 5 or so, at my cousin's house, she dressed me up in some of her older clothes that were more my size so we could be like "sisters." We were just playing, and she didn't have any kind of devious motive. To me, it was fun. When my mom and aunt saw me, my mom told me I didn't have to let Jenny dress me that way if I didn't want to. But I said it was fun and so she and my aunt just let us be.
She actually told me that I was pretty and "should have been a girl." I remember feeling proud that she said I was pretty. She was around 7 and I was only 5 but I still remember vaguely how it felt looking at myself in the mirror in a dress and with my hair fixed in a more girly way. Any kid playing dress up wants to really look convincingly like the character they are dressing as. I looked in that mirror and saw, not a boy in a dress, but a girl. I spent the day that wayÉ enjoying the play of being Jenny's "sister."
After that, I told my mom I liked Jenny's pretty underwear way better than how my underwear looked. According to what she's told me, I just kept bugging her about it until she started buying me panties and, eventually, that was the only underwear I had. No other boys knew what my underwear looked like, and my mother said probably it was best that I didn't talk to other boys about it. She said most boys are taught that panties are only for girls. So, I didn't ever talk about it. I just remember having a drawer full of panties. Some were fairly plain. Just briefs in pastel colors, for example. But they didn't have the ribbed "fly" that boy's undies hadÑwhich I thought looked ugly.
Jenny dressed me many times after that first time. Not every time we were there, but often. And my mom and aunt Susan would go along with our play. I remember them saying things like "You girls clean up, now, we need to go soon." Or telling Jenny to "Élet your sister have a turn." Things like that just became normal. It was a fun game that I looked forward to. My aunt even bought a few dresses in my size, so I didn't have to wear Jenny's old things.
I don't remember the first time a man saw me dressed that way, but Jenny and I played outside together when I was dressed as her "sister," so I'm sure some men or boys did see us. They wouldn't have known I was a boy under that dress.
I do remember one time, at home, a man my mom knew had stopped by our place to fix our bathroom faucet and, as was usual sometimes, I was just wearing undies around the house. I wandered into the bathroom to watch him work, and he saw my panties and asked, "You don't have a sister, do you Jamie?" I said no, and I was very aware that he was staring at my panties rather than looking at my face. My mom came in and shooed me off, telling me to let the man work.
Later, after he'd gone, she sat me down and talked about how it might not be a good idea to walk around in my undies when men come over. I thought it was a strange request at the time, since I had been that way when my aunt was around. I asked why and she just said that it might make the man uncomfortable. I didn't understand, but since so few men ever came over, I didn't question it. I was probably not yet 7 at the time. I was pretty much unaware of sex or of the idea that people got aroused.
I learned about that soon after, though.
I wore panties pretty much up until I went into Jr. High. At that point, I would have PE class and she told me other boys might say things to me if they saw me that way, so she got me boxers. I hated them. I wore panties otherwise.
But up until that, at age 11 or so,