The first trans person I met was Vanessa, my ex-gf's workmate in a yogurt shop in a shopping center. This was back in 1990. Vanessa was about 18 and living full time. I was a few years older but had been privately thinking about transition for a long time, and was feeling a lot of dysphoria that year. Up to this point I hadn't told a soul about my situation, although I came close to broaching the subject in an unsent letter to my girlfriend the year before. I presented publicly for the first time as a woman that summer (in daylight, that is, not counting the times I went out when I was 14 and 15 at night), but I had such a bad experience with it, it made me want to give up (which I did...for the next 4 years). Ended up crying on a park bench; I felt I would never pass and could never just feel like I could live as a normal woman. And then a few weeks later my sister found my wig and called me a "pervert". Anyway, while all that was happening, my girlfriend worked at this yogurt shop and sometimes I would meet up with her after work. A few occasions they both ended work at the same time and so I had some social interaction with Vanessa, but not too much. I knew she was trans from my girlfriend; her gender situation was known at work, and there were some things about her like her voice that could be interpreted as relevant. I remember wishing I could ask Vanessa about her transition, but 1) I never had any time alone with her, 2) She would have just told my girlfriend I asked about it, 3) It would have been rude, and 4) I just didn't have the guts.
My girlfriend had mixed feelings about Vanessa. She said that Vanessa had an attitude and was immature, but at the same time fun to talk with. The word she always used to describe her was "sassy". I had the distinct impression that she did not see Vanessa really as female, but still somehow as a sassy gay male. And then she got suspicious by how much I kept asking about Vanessa. Vanessa also wasn't the only TS my ex-girlfriend knew. A few years before I came out to my ex-girlfriend, I would see a woman on the bus that I wondered if she was trans. She was very passable but I had some intuition. Then one day my girlfriend pointed her out to me (I remember she was wearing a baby-doll dress), and she told me that she had gone to her high school, and was once male but gradually transitioned to female as a teen.
Then in 1994, I finally came to the point where I needed to begin transition, and took the very difficult step of coming out to my girlfriend. She already had strong suspicions because I had done a test RLE to see if I could pass, and she tore through my belongings to find evidence on me. So when I initially told her about my gender dysphoria in late September, she thought it meant I was a crossdresser, even though I did explain the difference to her (for a long time after that she didn't see much difference between crossdressers and TSs). And when I showed her in person what I looked like as female in November, she immediately compared me to Vanessa: "You seem really sassy now." But soon it became clear to me that she didn't understand that I needed to transition, so I discussed my dysphoria again and explained that I was TS, and her immediate reaction was: "What?! You want to be like Vanessa?" Then by December, I was told that I had to choose between staying with her or being Traci, so I chose to delay my transition again because I was not emotionally ready to break up (we had been together since 1987). But things came to a head less than a year later when I started therapy. During that time when I put off transition, my girlfriend and I would see TSs on the daytime talk shows, and she would often criticize them as "sassy". That made me wonder if she was comparing them to her old workmate. Also during that time, I would often see Vanessa working at Tower Records. Again I longed to ask her about transition (I hadn't ever met another TS before), but I knew it would have been totally inappropriate, so I never did.
The first TS I met whom I was open about my situation with was the head of the local support group, whom I met for the first time on November 1, 1995. She had been transitioning for three years. I went over to her apartment and we talked about my personal situation, how to improve my voice, the practical difficulties and realities of transitioning, and about the support group itself. Then the next day, about an hour before I went to my therapist appointment, I logged into Susan's Place chat at my university computer lab. Nothing much was going on for twenty minutes, until someone logged in who was also from my same state! She asked me if it was true I was living here, and I told her what university I was at. Then she wrote, "My God, I'm at the university too -- you're not that beautiful girl sitting next to me in the computer lab?!" I wasn't presenting female anyway, but I asked her which lab and it turned out to be the other one on campus. So we arranged to meet at the student services building just after my therapist appointment. She said she would be wearing a shirt with a monkey on it. After my appointment, I went downstairs and there she was, my new friend. She was 16 years post op, and was stealth, but we sat down and talked for almost an hour about my life, her experiences, and my plans for the future. And so this was the first friend I made who was trans -- and I wouldn't have met her if I hadn't come to Susan's Place to chat an hour and a half earlier!