New here-my story

I've always been a big masturbater and never thought it was a major issue until recently. Thought it was a normal thing which it is, although I would do it sometimes multiple times a day for a few hours pretty much killing all my free time after work until I go to bed and I would do it to a lot of crazy things like shemale porn, crossdresser porn, even gay porn once in a while. I have also messed around with crossdressing and when I needed more, I drove to another town where no one would know me and walked around dressed as a woman. The worst though would have to be, the sexual encounters I had. One was a date with a transsexual who still had her penis which I had inside me briefly. I knew it wasn't something I wanted once it had occurred so I ended that there. There is also a crossdresser who lives in the town by me, who's now on hormones to become a woman that I had dress me up and we gave each other oral. However, I still consider myself a heterosexual guy who loves women. I desire a beautiful woman in my life and by my side. A couple years back, I was dating this really great girl and we had a really awesome relationship going, but I felt like something was missing. I would go on the computer late at night when she was sleeping and looking at a lot of this porn and shemale stuff. She broke up with me a few months later and told me she had no feelings for me anymore and gave me a variety of reasons, but not this. It's quite possible she went on my computer and saw this stuff and that's what caused it. She's since met another guy and is happy and they're engaged. I want the same thing. I want to marry a beautiful woman and build a family but I don't want this crap getting in the way because it's not me. I was bullied and picked on a lot growing up and I think I turned to masturbation and these sexual thoughts as a escape from the real world. I live alone now and half the time I'm in isolation. My social skills suck. I mean if someone engages me in a conversation I can talk, sometimes briefly as I'm in a rush to get out of there and move onto the next thing so I can free up my time to jerk off later. But I can't approach someone and start a conversation. Very rarely, so I'm stuck dealing with the online dating. When in reality, I really am quite the catch. I'm a good looking guy that's athletic and in great shape. I have a good job with the postal service and have a nice little apartment for now. So a lot of things in my life are positive. Except the porn/masturbation/fantasies. I want to beat this so bad but every time I start I relapse so quick. I also wonder, would this be causing my anxiety because if I don't jack off for a few days, I get even more anxious because I'm thinking of it. Almost feels like my body is screwed and I can never get out of this hell. Really don't want to go see a shrink and get put on medication but could I do this on my own, without the aid of medicine or doctors? Or am I already screwed and have to settle on a lonely life with a lot of emptiness? I think the first step might be just deleting all this crap I have on my computer, especially the ones of me dressed as a girl and mainly the one with me with a penis in my mouth which I had taken just so I could beat off to it later not because I enjoyed what I was doing. Also get rid of the women's clothes and shoes I acquired over the years. Did that once before when I met my ex, then started buying this stuff again and stashing it in my old bedroom at my parents house so she never saw it. Another really bad thing I've started doing lately is calling Payless Shoe Source or Victoria's Secret and pretending I want to order women's shoes and I masturbate over the phone with the agent. I know, really fucked up, but I somehow get off to this and it's really embrassing and pathetic. Regardless, this is gonna be a long journey and I don't know if I could do it. Knowing my luck, I'll probably wind up crashing tonight.
Anyone going through what I am?

I don't think any of this is pathetic and you have at least identified that this is no longer serving you.  Did you start out cross dressing and all of that or is this porn escalation into riskier things?  It could be part of your actual sexual identity or it could be part of porn addiction.  Only you can decide and the best way to do that is to abstain from porn and masturbation and see what happens to your sexual tendencies.  You really need to make a commitment to change if this is truly what you want.

What needs are being served by this addiction?
-Security and certainty
-variety and uncertainty (emotionally)
-connection and love
-growth
-contribution

You can meet these basic needs through something destructive, like an addiction, or you can meet them healthily through relationships, worthwhile work etc.  It sounds like you want to get your needs met through a real loving relationship but something is missing (possibly the emotional variety) so you revert back to your old ways because it's easier to get your needs met this way.  A real relationship is a risk.  There are also risky problems and safe problems.  Porn addiction is a safe problem because although it's a problem for you it feels "safe".  A relationship is a risky problem because it requires effort and thinking outside yourself.

Just something to think about

I think that it is mostly an escape from reality. I was bullied at a young age and as an only child had a lot of alone time. The dressing first started with my moms clothes and shoes then I bought my own years later. I'm almost totally sure that I am straight as I have only been with genetic girls or men dressed as women. As I am posting this I feel ashamed of myself and feel as though I screwed up in life. Often times I feel as though I am not good enough. I'm always quiet and avoid social contact unless it's initiated or with close friends or family. I'll sometimes seclude myself from them so I could pleasure myself for hours at a time. Then I have feelings of regret. Wish I could spend more time with family, enjoy life and find someone special to have fun and grow with. But the anxiety and this addiction overwhelm me. I was good last night. Went out and ran after work then did chores around the house to keep me busy. Don't know how today will go.

I wonder. Can I reboot? Or do I need to see a specialist? Or is it too late and I'm fucked as far as bringing a great girl into my twisted world?

It's very hard for me to explain over the internet on a forum but you are right it is an escape from reality.  The reality is your depression and lonliness.

I definitely think you should see a professional because I think you have a lot of issues that go deeper than the porn addiction (heck we all do!).  Why not throw out a life line to someone who can really help you