My current boyfriend is a transsexual man, and several of my friends are also trans.
Three that I know of. Two MtF, one of whom I knew before. They are both kind of whiny and sort of depressed (and the one I knew before was then, too). It’s hard to say if they’re happier, though, because that’s what I see and may be at odds with what they feel. One FtM, who seems pretty happy. Which is about what I’d expect. The two women worked for a hospital, one as a nurse (this could explain the discontent!) the other as some kind of health educator. The guy’s a lawyer.
Somebody I knew in college also transitioned, but I lost touch long before that happened.
I must say, I’m pretty sure there was a rock star before who transitioned, and whose voice didn’t really change all that much. I can’t believe they’re calling this person a MAJOR rock star. At least the other person–whose name I can’t think of, nor can I remember if said person ended up M or F–was somebody I’d heard of before, even if I can’t remember the name now.
There is one other. Didn’t know her well, but I encountered her a few times, and had no idea she used to be a guy until I read a news story about her.
I had a transgendered friend before I ever had a gay friend. George*, a friend I have known since I was in 7th grade, dropped off the face of the Earth for about two years and reemerged to the world as Susan. For reasons I don’t entirely understand, she decided to drop off the face of the Earth while she was transitioning. I won’t lie to you, it was somewhat difficult for me to process. We even treated one another differently when we met after she announced to everyone that she was a woman. For example, when we first met one another for lunch we hugged each other. Something that we never would have done had she still been George. The most upsetting part of it for me was when she told me George wasn’t a real person. While I understand where she was coming from I couldn’t help but think that I was friends with George for years and he sure seemed real to me.
However, she seems much happier today than she was in the past has a much sunnier disposition. I miss George but I’m happy for Susan.
I’m a trans man and have been taking care of support networks stuff for fellow trans folks for more than ten years, so I think I’ve known about a bajillion other trans folks of all stripes.
There is a trans man I knew and was kinda close friend with for years when he was presenting as a very fem girl. When he came out as trans, even for someone like me, it took a good bit of time, something like two years, before thinking of him as “he/him” in my head, though I never screwed up in public.
Does that mean “originally man, now a woman” or vice versa?
Originally woman, now man.
You can tell since he referred to him as “transguy” “boyfriend” and “him.”
I think vice versa, since Miller now refers to him as a guy and other FtMs.
Regards,
Shodan
In answer to the OP, not that I know of. Somebody I went to high school with and knew tangentially supposedly went MtF, but that was nothing more than a rumor I heard at our ten year reunion.
There appears to be more than a little controversy on the prevalence of transsexualism. So I am not sure whether to be surprised that I don’t know any IRL, or if this is how it usually is.
Regards,
Shodan
One of my university buds just came out a few months back as being MtF.
She thought that we all weren’t talking to her about it because we were skeeved out or unsupportive. Turns out we just didn’t care if she was a she or a he (except that we are all having a heck of a time with pronouns and using her new name). She is the same person and we treat her the same way.
Good gosh, how do you *do *it? I went on a message board once, thinking I could offer some advice or support–and it was so full of whiny, overly dramatic Emo teenagers that I had to skedaddle the hell out of there, feeling about 100 years old.
Yes, a large number of transwomen. Amazingly, no transmen that I know of.
Did you know them before or after they transitioned? Almost all them I knew or met after they transitioned. Over the years (decades nearly) I’ve found that almost all of them have compounding problems that make their lives hell, and I’ve tried to help out how I can, but I have problems of my own to deal with so my abilities and energy is limited.
How did it affect your relationship with that person? When I found out they were it made me feel protective towards them, knowing that to be TG/TS is considered in the US to be about the worst thing since vegan Muslim baby-rapists. Even on the incredibly liberal and “enlightened” SDMB I’ve seen an incredible outpouring of disdain, disgust, and hatred towards TG/TS individuals, and I’ve found a good acid test of whether a person is worth a shit as a human being is how they treat TG/TS persons. TG/TS folk have very few places where they can be allowed to just live their lives.
I have one (online) male friend who I’ll call E, who was FIB (female-identified at birth). When I first met E I only knew him as a young gay man who happened to be one of the most charming, articulate, and intelligent people I’ve ever encountered, even considering his young age: he’s a queer activist with a lot of very thought-provoking things to say. Later I found out about the FIB-thing and that he was planning to transition at some level, and while it took me a little while to process, I came out of it with the same feelings as Una: protectiveness and the desire to work towards a culture and society where no one gets crap about being TS/TG. (Honestly, what weirded me out more is finding out that E is the child of two very prominent people, so unfortunately he’s had to go through a lot of his struggles far more in the public eye than he should have, and delete blogs/LJs/etc. when assholes from the National Enquirer and Daily Mail get a hold of them.)
I’m sure I know other people who are transgender as well, even if I’m not aware of it. No skin off my nose, except that I try to watch my language and not make assumptions that are unwarranted.
Born female, now identifies as male.
Oh, I know who you’re talking about, and I lost touch with him a while ago due to the process you describe. Glad to hear he’s doing well.
I don’t know any transgendered person, nor would I probably know one if I met one. I have really bad gaydar, or transdar, whatever
Very cool that you know him too! I also lost touch last November but I kept his email and recently dropped him a line. I’ll PM you his blog info. (It would probably be perfectly OK to just post it here, since he’s come out publicly with who he is, but it still just doesn’t feel quite right.)
Yes, I did, I’ve lost contact with her now but a good few years ago a woman I’ll call her Ella was asking about clothes for tall women, so being about 6ft tall meself I gave her links to sites that sell clothes for tall women. We became pals.
I was chatting online with her for ages before I found out she used to be a guy called John.
I’d seen photos of her and would never have known if she hadn’t said anything!
I shall have to look her up on facebook, she was funky cool! 
I would no longer say I know her, as we had lost touch years before she transitioned. Of the people I worked with at that job, he was probably the one I got on the best with. I helped him with a project after he left and started free lancing. He had a worse tool fetish than me. Not that women can’t, but it seems such a stereotypical “guy thing.” My jaw hit the floor when I heard (reliably, and since confirmed) through the grape vine that he had transitioned…not over the process, but that I could have utterly no clue that this might be in his future. The one I knew would have been a good Doper candidate…there are enough clues above for her to figure out who I am. I’d be tickled to hear from her.
One of my best friends is trans and she revels in breaking gender norms while she works on her car and does other neat handyperson stuff. She’s awesome.
Is it dumb that I feel a little bit starstruck responding to you? 
Thanks, though. I remember your contributions and you played a big part in this feeling like a trans-friendly space at a time when I was desperately seeking those out.
Gawrsh! * blushes prettily * I do not like talking about my private life, and was actually “outed” here, but I do think it’s important to do so, because–like with gays–the more transgender people who are visibly out and about, the less weird and creepy and nuts we will seem to the public at large.