As she was leaving my counter, I called out to her and I said, “Hey, if there’s anything else I can do to help here’s my card.”
I gave her my business card; wrote down my cell number on the back and told her, “Don’t hesitate to text or call me, if you need anything.”
I watched as she walked away from my desk, forms in hand and I was screaming inside for her to come back and talk further. But I was at work. This wasn’t a social meeting and I surely couldn’t chase a shemale out of the office in hopes she would want to talk to me anymore. As she walked through the double glass doors of our office and turned the corner, I saw her walk away and I had to get back to work.
I thought about her for the rest of the day. And truthfully over the next few days, I had hoped she would have come back into my office. Called or even texted me, but as the days passed. I heard nothing. I was disappointed because I will tell you, I went way above and beyond trying to make sure she knew I was there to help her. Give her some inside tips and tricks and was hoping, she knew I had an interest in her change. I just had hoped she would take advantage of my friendliness and openness in trying to help her and reach out. But by the start of the next week, I still hadn’t heard anything and just went about my life.
However, late Tuesday evening I got a text alert on my phone while I was driving home. I don’t know if some of the readers will remember, but the first generation of flip-phones, which had the capability of texting, had small screens, that were hard to read and even harder to reply to, so it waited until I got home. Once home, I realized it was a number I had not programmed in. In opening the message, I read; “Hey Tim, this is Jillian. I met you last week looking to change my birth certificate information. I hope you remember me. I submitted all the paperwork today by mail, I hope it goes through. But I wanted to thank you for all the information, the tips, and for being so kind to me at the counter. It was very comforting, that you didn’t judge me”
I about shit myself. Seriously, I was like; holy fuck she texted me. I wanted to blast out a long message back, but I had to be smart about this. I knew I couldn’t come right out and hit on her, or be like some drooling retard who was like, “I love shemales.” I had to be smart. I sat and thought about it for a while and finally composed the best response I could.
I wrote, “Jillian, I hope all the information I provided will work for you, and I hope the State approves your changes. I have had several people come in amid their transitions, and I am very supportive of your lifestyle and who you feel you need to be. I give you credit for the change; I know it’s not easy. If there’s anything else you need or need someone to talk to about anything, I am here. Don’t be shy.”
I figured that was the best I could say without coming off as someone who wanted to fuck her. I had to be professional, honest, and compassionate, yet leave the door open for any further communication. After hitting send and knowing it went through, my heart was thumping in my chest. I felt like I had violated the rules at work. As if I had overstepped my boundaries and I hoped I didn’t come off like some sissy-ass dork who was being forward or playing games. But I had sent it, so even if it appeared that way, there was nothing I could do about it now.
Her response came back in a while later and was phrased as simply as “Thank you. I appreciate it. And I will.”
I couldn’t tell you how badly I wanted to keep texting her. How many questions I had for her. How many things I wanted to ask her. Such examples would have been. How long as you lived as a woman? Do you have breasts? Do you date men? Are you dating anyone right now? Could I take you to dinner? The list was endless, but I surely wasn’t going to push my luck, or have her call and file a complaint against me, since I was making these texts personal, instead of business-like.
I waited and wondered for days until she texted me again. During this message, she asked; “Tim, since you said you have had others ask for the same birth certificate changes, do you know if they were successful? Now I’ll be the first to admit, I never had anyone come to my counter and ask me to change sex on a birth certificate. I’ve had requests for changes such as date or time, the spelling of a name, weight, or race. So, I had to play this right.
My answer to her was; “Jillian, I am unsure. Once the paperwork is filed, I won’t be advised if the changes were approved or not. I just provide the forms needed to make the change, not whether the change actually occurs.”
This time our conversation went a bit further. She asked me, how long have you worked there? Did I like my job? Does the State pay well, etc.? And I asked her a bit about herself, in the general aspect, where she worked, where she went to school, etc…
But as the days progressed and as we began texting more often, I slowly began asking more personal questions of her. And I believed she was just as interested in getting to know me more as well. It got to the point that most evenings we were texting and opening up more about ourselves and our hobbies, interests, likes and dislikes, and life in general. I finally mustered up the courage to ask if I could inquire about many of her physical aspects, during her transition. Justifying to her that I was supportive and very curious about how it went. Jillian was very open to discussing her transition from a man to a woman, so I got my chance to finally ask what I had been wanting.
In the short version, she had been transitioning since after college. She knew she liked men more than women and always felt like she was a woman. She worked as a nurse in an assisted living community and was still living at home. After saving enough money, she had breast augmentation, but still could not afford the hormone therapy (new at that time), but she grew her hair out, had friends who helped her pick out clothing, and learned how to do make-up and MOST IMPORTANTLY, she wasn’t dating anyone at that time.
I did boldly ask her out for dinner, via text, something I still regret, but since we were moving along so well in our conversations, I took a chance. And, we agreed to meet. And that’s where our brief, but exciting relationship started.
Our first date was set for Friday night, 7:00 P.M. at an Italian restaurant we had chosen. I arrived on time and was seated. She was 45 minutes late. As I waited, she began texting me. The first text I got was; Tim, I’m sorry. I’m running late. I’m waiting for my parents to get home. I’ll be there shortly.”
The second a bit later; “Sorry, I was getting into my car and ripped my dress, I had to go back in and change. I’ll be there in a bit.”
About 30 minutes later, the third message; “I’m on my way but traffic is jammed. Please wait for me.”
Even the waiter had come to my table a few times, almost teasing me being sarcastic in his tone, asking me; “Is your date still coming?”