I think you should get back to working out. I think it'll help you with a lot of things. Self esteem and confidence for one. Being self conscious isn't good. I say work on it. You can do it.
As for being trans, I have some trans friends who are non-op or pre-op and had success on OK Cupid. As long as you disclose you should be fine. There will be weirdos who pm you but there will also be decent surprisingly open-minded men on the site.
Self esteem and having confidence are important. Keep at it!
I want to get active again, and wish I wasn't struggling with it so much. Just a few years ago, I'd get up at 5, go for a jog, do my morning yoga, walk to and from work, be on my feet all day at work, then do P90 before bed. I got out of those habits after quitting that job, and haven't recovered.
I have some serious self-esteem issues dating back to grade school, and transition has helped a lot with those issues in some pretty unexpected ways. Basically, I now think pre-transition me was pretty cute, which I never felt back then, which made me realize that a lot of my feelings of unattractiveness that I have are in my head. Even then, every day is an exercise in unlearning negative thought patterns. Some days(certainly more than ever before) I feel good about how I look, but stuff like my avoidance of cameras shows that I'm not where I want to be, either.
EDIT:
Whaaa.... really
How did you last this long? Genuinely curious
My body ran on testosterone for 26 years, and I didn't really need to enjoy it to do it. Once I started hormone therapy, my buttons were different, and while masturbating felt
way better than before, I suddenly felt like I didn't know what I was doing anymore, so it got a lot harder. At this point, I just... stopped. Over the next couple of years, I masturbated only a handful of times.
The thing is, I knew I needed to be masturbating, even though I wasn't. When you have a penis and your body isn't producing testosterone, things can, uh, atrophy unless you're actually using what you've got. I decided that I needed to masturbate at least weekly, which meant that I needed to start having fun. I did some research and picked out a vibrator and an anal toy, and everything is soooo much better lol. Multiple orgasms aren't uncommon(and each one feels better than they ever did before). I usually masturbate every 3-4 days now, which is a frequency I'm pretty happy with.