I had just turned 19, I was a feminine type guy with virtually no body hair or facial hair, or at least so little that I felt compelled to shave it off because it looked so pathetic. I also had a skinny waste that curved down to a big girly ass and thighs.
I looked a lot like my older sister, she was shaped like me but with a nice set of tits and long black hair with cute bangs. All the guys loved her. I remember hearing stories about her circulating through school. She had done things like have sex with teachers and get fucked by half the varsity football team in one night..
From a young age I remember guys picking on me about my big butt and I hated it. I wanted to be manly but I just couldn't hide my feminine features, no matter how hard I tried. I would try to do workouts to lose my big butt and frustratingly it only got bigger.
I was a good looking guy but was just way too shy to ever make moves on girls. I also had no guy friends, so by default I had turned into a nerdy introverted type - even though I wasn't friends with the nerds either.
I finally dated a girl briefly when I was 18. She couldn't get my dick hard even after playing with it and sucking it. She ended up spreading the news that I had a tiny dick that didn't get hard and that I was gay. Kids are mean and the rumors and subsequent bullying was tough on me in my senior year of high school.
This all led to me questioning my sexuality and having gay thoughts. I started watching a lot of gay and sissy porn. I stole a dildo from my sister (she had a lot of them) and I'd take it into the shower with me and soap it up good then slowly put it into my ass. I was secretly turning gay and becoming obsessed with cock.
The porn I watched made me fall in love with masculine men who had big cocks, specifically daddy types. I wanted to play with an older guy but I didn't really know how to make it happen, also I was scared that everyone in my hometown would find out if I did. So I suppressed my urges and kept that side of me secret. I dove deep into daddy/boy porn and fantasized about letting an older guy fuck me and make me his bitch.
I jerked my little dick so many times, fantasizing about big cocks and being a slut for an older guy. It was all I could think about and all I cared about. It was the only thought that made my little dick get hard anymore. And I increasingly found myself playing with my ass hole and putting the dildo in me every time I masturbated.
The summer after I graduated high school I was sent to live with my uncle, the oldest brother of my single mom. My mom just wanted me out of the house and I had no job, so getting an apartment or finding a roommate would have been impossible and I was planning on taking some time to decide what I wanted to do before I went off to college.
My uncle who I barely knew lived in a very rural area, I was reluctant to go but I really had no friends or social life in my hometown anyway. So I looked at it like a chance for a new start.
I'd be lying if I said I didn't think about hooking up with my uncle from the very first time I found out I was moving there. It seemed like a far fetched fantasy though and that the likelihood was probably really low. So although it was a fantasy of mine, it didn't seem realistic. I pictured me being his little live in girlfriend, wearing skimpy clothes around his house and letting him fuck me whenever he wants.
Since I had grown up in a house with just an older sister and a single mom, I was very feminine in my demeanor and behavior. As I had delved deeper into the gay sissy porn, I had slowly started to shift my wardrobe to tighter fitting pants and leggings, as well as skimpy booty shorts like my sister would wear. I hadn't been wearing these clothes to school yet but I had worn them around the house and in front of my sister and mom a lot, my sister would comment on my big butt and how she was jealous of it. She had a big butt too but she still envied mine.
I started wearing exclusively tighter fitting and skimpy clothes at my uncles house. I looked at it like an opportunity to be what I wanted to be and thought worst case scenario if he doesn't like it he can send me back to live with my mom. Best case scenario I hoped to seduce him with my girly body. I even wore panties I stole from my sister sometimes, if I was feeling horny enough.
There were many times I caught him checking me out. Other times he caught me checking him out or staring at his crotch.
I hadn't grown up with a man in the house, so I had no idea how to act around one. I was very timid and subservient to my uncle. I treated him with a tremendous amount of respect and gratitude.
Needless to say my uncle picked up on my feminine energy, he treated me in what I would describe as a very daughterly way, rather than a son or nephew. As we got more comfortable together he started to treat me more like his little girlfriend or something. He would take me on long drives and put his arm around me if I was cold. We would sit really close on the couch, almost cuddling but not quite, and it felt so good. He was such a big strong masculine man, as manly as they come, I never thought that he was actually attracted to me.. I'm not really sure what I thought at that point. I figured my gay fantasies were just leading me to believe something more was happening when really it was nothing gay.
