Just hoping to get people to read my wall of text and give some advice

Hi everyone, I really need to dump and get some advice and I have no one in real life I can talk to about this.

I am a mid-twenties male who has just kinda gone with the flow on my identity and sexuality. Took what society expected of me and walked with it, it was the easiest way to do things. I have had people question me about my sexuality my entire life, mainly if I was gay or not. I have always just brushed it off with a joke, but it makes you wonder after it turns out your entire extended family, and most of the people you have met have assumed you were gay until you said you weren't. Maybe everyone else sees something I don't.

Thing of it is, I have been curious about what my life would be like as a woman for a long time now, but I don't know if I am dissatisfied with my gender or sexuality. I am someone who enjoys learning, and gaining new experiences and perspectives, and I think I mainly just want to know what it's like to be a member of the other half of the human race.

I'm not really sure when or why I started wondering what being a woman would be like, but I have been having these thoughts for so long, maybe it's more then curiosity? To be honest, I'm not sure why I am writing this, think I just want to get it out of my head and give me a reason to slack off.

My earliest memory of 'transgender-y' thoughts start with me pretending to be a girl online in an MMO in my early teens. This transitioned into reading various transgender fan fics and webcomics online all through my teenage years out of curiosity with the act I was partaking in. Kept playing through a series of different MMOs throughout my teens, 90% of the time I faked a female persona.

It was a lot of fun and I greatly enjoyed pretending to be anyone else besides the awkward teen I was, but it was always tainted at the core by virtue of it being a massive lie. I would always end up quitting due to the effort of maintaining the other life separate from my real life friends who would join me in playing the game, or just in disgust at myself at tricking people and move to the next MMO.

I wouldn't say I have been lonely or anti-social in my life, I have always had a few close friends, and can be outgoing and sociable particularly now that I am a little older and experienced; but I do land more in the 'nerdy loner' then anything else, and like many of my brethren, spent most of my teenage years jealous of the fact that being a girl seemed like an easy way to get attention.

Leaving my teens, I kept up with most of the webcomics mostly out of habit, and haven't played the MMOs for a long while. What replaced them though, was I started going to erotic roleplay chat rooms and pretending to be a woman. During the MMO phase, I never let anything sexual come up, so I am not sure where the push to move in this direction came from. I have continued with this up to this point in my life, usually pushing it away as something weird, creepy, and a waste of time after a session of it; then falling back into it like a bad habit a few weekends later.

To be honest, it's more fun, but a lot scarier, when I can just experience an in-depth or romantic conversation "as a girl". For example, roleplaying games like the Mass Effect series where you can essentially direct a romance; I always play through as a female character and it really really strikes something in me. That might be good writing more then anything though.

I have never had anything anyone would refer to as a romantic or sexual relationship with either gender, due to being somewhat shy and terrified of rejection just like everyone else in my teens, and post high-school I got a crappy job barely able to pay the rent and food which left me depressed and not wanting to be out and about a lot, and after finally getting out of that I went to college and unleashed my workaholic, leaving me too focused on good grades and internships to ask people out. I am still in college, and part of what makes me want to write this is the fact that all this confusion is distracting me and eating away at my work ethic. Back to the point, this lack of relationship and sexual experience leaves me feeling like I have no ability to discern if I am happy or unhappy with any part of my gender or sexuality.

I don't know what this all means, if I fake being a girl online just because I like the attention it gets me, if there is some part of me that prefers the idea of being female, or because I want the attention of men.

I have never cross-dressed, but this isn't the first time this confusion has reared it's head, and each time it does I start investigating LGBT related stuff, and the subject comes up and I think “Well, maybe I should, it would be a new experience at the very least”. I can't imagine what it would get me though, in my experience there is never any big "movie moment" where I look at myself in the mirror and suddenly everything clicks in real life.

I have experienced a lot of depression and general unhappiness in my life, and a severe lack of self-esteem and self recognition of any accomplishments I might have to my name, which I have always chalked up to my perfectionist streak. If I'm not amazing at it first tilt, I suck at life apparently; but I feel like I largely have that under control these days, having taught myself to step back and rationally consider why I might be having difficulties, and then forcing myself forward in the face of failure.

I am just rambling now, but I still feel empty and unhappy sometimes, which I usually chalk up to stress, because I love my work and I love learning about it. But I guess I feel like I need to start exploring other avenues as to why I might be unhappy, and my sexuality, or lack there of so far, seems like a place to start.

Thanks for reading my massive wall of text if you managed to get this far. I think I am really just hoping for someone else to at the very least say, “Yeah, I am crazy like you, don't have any answers, but we are in it together eh?”