I’ve been doing a lot of soul searching lately as to why I am the way I am. Here’s what I got so far.
I found out about sex at a very early age. The first time I remember being attracted to a girl was in 2nd grade. A friend of mine and I started fooling around with each other’s dicks when we were 9. We’d masturbate in front of each other. That progressed to masturbating each other. Which lead to blowing each other, then getting completely naked and humping each other and eventually when we were in our late teens, we began penetrating each other.
I never saw myself as gay while I was doing those things. When he’d suck my cock, I’d pretend he was a girl and when I’d fuck his ass, same thing. He did the same when the rolls were reversed as well.
I wanted a girlfriend but didn’t have the confidence to go get one, and this, I guess what you’d call gay sex was what was available.
I have two very different sides to me sexually now that I’m an adult. The first is bisexual. I absolutely adore women! But I also enjoy men as well. This bisexual me, is always a top when I’m with men though.
The other side of me is a cross dressing, cum swallowing whore. Putting it politely. I love to wear women’s clothing, not just lingerie either, I have an entire wardrobe for any occasion in my 2nd dresser. This side of me loves being fucked in the ass, swallowing cum and being treated like a woman. I’ve even named her Stephanie. That was the name my mother was going to give me if I had been born a girl.
My mother was that first woman I was attracted to back in 2nd grade. She wasn’t some knockout blonde bombshell or anything like that, in fact, she was overweight and mostly average looking if I can be honest.
This isn’t one of those bullshit stories where I start it off with “my mom and I were always very close.” Truthfully, my mom and I were pretty much normal. It was just us in the house, my dad left us when I was 6 and I never saw him again. I have an older sister but she’s 12 years older than I was and by the time I was 7, she was already out of the house and in college. With her out of the house I now had babysitters that would come over while mom was out on dates. Almost always a teenage girl from the neighborhood and whether they were cute or not I always fantasized about them.
Around the time my friend, Jayson, and I started exploring each other’s dicks, I also started being left home alone while my mom went to work. I’m an extremely curious person and when left alone I enjoy snooping thru peoples stuff to see what they’re hiding. I would snoop thru my moms dresser drawers and closet all the time.
The first time I found anything interesting was when I was 9 and I found her dildos/vibrators. She had 3: the first was just a normal looking dildo, maybe 6 or 7 inches and the second was similar just larger, maybe 10 or 11 inches. Both had suction cups on the bottom. Then she had a fairly standard looking vibrator. Next to them was an opened box of condoms.
At that age I began spying on my mom constantly. When she was in the shower, I’d try to sneak a peek if I could. When I heard the water shut off I’d open the bathroom door and say I had to pee just hoping I’d catch a glimpse of her naked. I would also wait until she fell asleep and I’d try to lift her nightgown and see what I could. I even hid in her closet while she was showering and peek at her getting dressed. It literally became an obsession of mine.
When I was 10, snooping thru her drawers was no longer enough. I for some reason began wearing her underwear and lingerie/nightgowns. Whatever I could find. I loved the feel of silk and lace on my skin. I even went as far as taking notice of which ones she wore the most and which she never wore. I took a couple she never wore and put them in my dresser drawer and would often sleep in them.
When I was 12, there was another kid that lived in the apartment above me, Jo, and him and I started exploring each other’s dicks as well. I eventually confessed to him my interest in wearing women’s clothes and to my surprise he thought it was cool. That’s when I began dressing up in whatever I could for him and I’d model it for him. My moms clothes were just a bit big on me though so Jo started sneaking stuff from his moms closet. Jo’s mom was much smaller than my mom and as it turned out, her clothes fit me rather comfortably.
I wasn’t getting any attention from girls and I wouldn’t until I turned 17 so most of my early teen years were me and boys. Jayson and I eventually started having anal sex when we were 16. He was openly gay by this point and very femme. He never even asked to penetrate me, it never came up. It was as if there was just an unspoken understanding that we had, I was the top and he was the bottom.
Jo, on the other hand, made me feel different. We continued to play dress up and he was just a super sweet guy that didn’t have a mean bone inside him. So when I’d dress up, he made me feel sexy and beautiful even though I wasn’t.. well sometimes I was.
I had never considered letting Jayson fuck me, but Jo, I wanted him inside me constantly!
This is where the split happened. I still don’t fully understand it, and I have no idea when I wake up which side of me I am. Sometimes I’m just me. A bisexual man. But on other days, I’m this beautiful woman (in my head) that just wants to be treated like a woman and the men that do that I’ll be a filthy whore for them. Very strange.. thanks for reading this. I’ll probably continue to write more of these as I search my soul. I have some crazy stories that’s for sure.
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