Chapter 3

Robert

I woke up around eight on Sunday morning and looked across at Sandra, still asleep. I got up to head to the bathroom, and when I returned, she was awake and looking at me with a smile on her face. She looked so peaceful, and I still couldn’t believe what a great night I had just had with her.

“Thanks for the lovely evening last night, Robert. I enjoyed myself, and if you would like to stick around, I can make you something for breakfast.”

I crawled on the bed over to her and gave her a good morning kiss.

“Please take a shower while I start breakfast, and there are spare toothbrushes in the vanity drawer if you want to brush your teeth.”

I smiled and said. “Sounds good to me.”

We both got up and embraced, and I went back to the bathroom.

When I got out and changed, I could smell bacon and eggs from the kitchen, so I wandered downstairs. Sandra was wearing a beautiful silk robe, and I immediately kissed her again. We chatted while she was making breakfast.

“Please help yourself to a coffee, and cream was on the table.”

“Did you want to do anything together today?”

She thought about it and said, “How would you like walking along the trails in the nearby state park? The leaves on the trees are changing color, and this looks like a great sunny day to go and see the fall colors. I can make us a few sandwiches so we can take lunch.”

“I will have to stop by my place to change into some outdoor wear.”

“That sounds like we have a plan; I can drop by your place if you give me the address once I have a lunch made for us.”

I agreed it was a great idea, so I wrote down my address, and she said she would come by to pick me up. I left Sandra’s place, returned home, and changed my hiking attire. My phone rang about an hour later, and Sandra said she was waiting out front and asked me to come down.

I walked out of my building, and Sandra was sitting in a little red Porsche 911 cabriolet. I gave her a big smile, got in beside her, and kissed her.

“This car is a nice ride, Sandra!”

She smiled and replied, “It’s my little toy since I love to go out for a drive on a sunny day with the top down.”

I won’t say that Sandra drove like a maniac, but she did like to accelerate hard and corner quickly. I smiled and called her a show-off, and we both laughed. She stayed off the Interstate, and we drove along the two-lane backroads until we entered the park. She found a parking spot and raised the top. We got out of the car, and she opened the frunk and removed a small backpack.

“I can carry that, Sandra.”

She smiled and handed it to me. The park had some very scenic views from its trails. Several reservoirs were there, and our trails were in the hills above them. The fall colors looked great, and there were many yellows, oranges, and reds.
We walked and chatted along the way. We found out that we both had kids, and they were around the same age and in college. We both had similar careers in computers, though I worked independently, and she worked for a large company. Both of us had been surprised by our divorces. I had just divorced a few months ago, and Sandra was divorced from her spouse for almost four years.

“Sandra, how is your ex doing?”

“I don’t know. We haven’t been in contact for a few years now. I called my ex’s parents, and they told me that they rarely contact them either, as their parents were not in favor of the divorce and had told them so.”

“My ex-wife changed her number, doesn’t talk to our kids, and seemed to have divorced herself from the entire family, though I wasn’t sure what we had done to deserve that treatment from her.”

“Well, there is one thing good that came out of my divorce,” she told me.

“What is that?”

“I met a great guy,” and she kissed me.

“And I feel I met a great girl. Sandra, I’m thankful we met,” I said and kissed her again. We stopped at a bench with a beautiful view, and I said, “How about lunch?”

She agreed, and we sat down and ate the sandwiches she made for us. She gave me a bottle of water and an apple as well. We admired the beautiful view overlooking the valley and the spectacular fall colors on the hillsides. We continued to walk the trails until around three and then started to walk back to the car. We made it back to the car around five, Sandra folded the top down, and we were on our way. As we were driving back to the city, she told me of a great little restaurant on the way home, and we decided to stop there for dinner.

It was in a small town. We parked the car and could get in for dinner without a reservation. The food was delightful, and we shared a bottle of wine with our meal. It was so enjoyable to talk to Sandra. I think I said this before, but she seemed knowledgeable about everything and always had an excellent opinion. I enjoyed this aspect of her, as she was funny, intelligent, and beautiful. She was everything I wanted in a woman. After dinner, we jumped into her little Porsche, and she drove me back to my place.

She said, “I enjoyed our day together, Robert, but there are some things I have to do for work tonight, so please call me next week, and we can make plans.”

I was in the same situation when I had thought about it, and I kissed Sandra goodnight and went up to my place.

Sandra

As I drove home, I kept thinking about Robert. "He was the first man I met who seemed genuinely interested in me. My next big problem was how to tell him about the transgender elephant in the room. How would this affect our relationship? Would it kill it like all my previous relationships? I didn’t know the answer to this question. When I got home, I looked it up on the web and found some interesting answers. I found the best one was to probe him a little and talk about transgender people, in general, to see how he felt about the idea. Find a quiet place to tell him about yourself and be honest if he seems receptive. I thought about it, and I knew I had to tell him the truth soon, or I would never be able to do so. What made things worse was Robert had said to me that he admired how honest and straightforward I was with him, and here I was lying about who I am."

I finished the project for work and decided to sleep on the matter, but I still gave myself a deadline to tell him the truth by the month’s end.

Telling Robert, I was trans could go either way. We could stay together, or he would be disgusted and leave me. The problem was I had no way of knowing, but given my track record, my relationship would soon be over. I was hoping it wouldn’t be the case this time, but I was zero for ten with boyfriends, as I had lost them all when I told them I was transgender. Their male egos made them leave, and I didn’t know if Robert was the same way.

Wednesday night came around, and Robert asked me if I wanted to go out with him for dinner. I agreed, and we met up at a local Italian chain that we both liked. I was there first, and Robert soon joined me. We had a great meal, and we were waiting for dessert. We were quickly served and were enjoying it. I looked at Robert and figured that now was as good a time as any.

“Robert, there is one thing I have to tell you about myself.”

He stopped eating, took a sip of his coffee, and said to me, “And what is that?”

“There is no easy way for me to say this, but I am a transgender woman and have been one since my divorce from my wife almost four years ago.”

He stopped and just stared at me, “But you are a woman?”

“Yes, I feel like a woman, but I am transgender and have had surgery to remove my boy bits.”

He sat back and looked at me. “Wow! I would have never have guessed it either. I just figured you were a tall woman.”

I thought, “He was still here and hasn’t run away. This relationship hasn’t gone down in flames yet, and things are hopeful.”

Robert continued, “I don’t know what to say after that, Sandra. To be honest with you, this news is quite a surprise, and now I can see why you asked me earlier about my opinion of transgender people. You are the first transgender woman I have met, and I am very fond of you.”

“I guess the question is, can my male ego get through this? To me, you are a woman, though I will have to work through my emotions now. You don’t fit the definition of a transgender person, you don’t look masculine, and you don’t have any boy bits.”

He looked at his dessert and took a couple more bites.

“I still think you are the perfect woman for me, despite this transgender thing. I am glad you told me before we got too far in our relationship. God, this is so weird for me. I like you, and this has thrown me for a loop.”

“As our relationship goes, could you let me think about this until the weekend? We can go out on Friday night. I need to stop and figure all this out, and I enjoy your company; it just feels so weird right now. I am sorry, but I have to go before saying anything stupid, but I will call you on Friday.” He pulled some bills out of his wallet and left them on the table, and then got up and left me in the restaurant.

“That went well,” I thought to myself, “Maybe I should take odds if Robert calls me or not on Friday.” I have been in this situation so many times before I didn’t even start crying, and I just got up and left as well.

I got home, and then the waterworks opened, and I started to cry. Maybe I should give up on men. It seemed that they couldn’t get over that I was once a man, even though I now looked like a woman in every detail. Sometimes life sucked. I just sobbed silently and turned on the TV.

Robert

“Jesus, what do I do now?” I thought to myself while driving home.
I drove home in a fog and didn’t know what to think since I had so many conflicting emotions. "Sandra told me she was once a man, and we had sex together, so does that make me gay?" I just figured I should sleep on this, and not knowing what else to do, and I just fell asleep.

When I woke up the following day, I realized that I needed more information. I called up my psychologist and asked if I could come in to talk about a relationship that was giving me conflicting emotions. She asked why and I told her my date told me she was a transgender woman, and she responded that she could see me at 3 pm.

We talked for an hour. I told the doctor everything I knew about Sandra. The doctor asked me how I felt about this woman before I knew she was transgender. I told her I thought she was great, and we were perfect for each other.

“So why do you feel that she is different now?”

“Well, she misrepresented herself, and she isn’t a real woman.”

“Well, she had you fooled, and you have seen her naked too.”

“I blushed and said yes, that’s true.”

“So why are you so upset now? She was honest with you; she didn’t have to say anything, as there is no law saying a transgender person must tell anyone. Why does this upset you?”

“I’m not gay, doctor.”

“Okay, but does she look or act like a man?”

“No.”

“So why are you worried? It sounds like she is a woman in all the ways that count, and you are afraid because she has a Y chromosome since it’s not apparent otherwise.”

“Maybe my friends will think I am gay.”

“Again, is there any need to say anything to them?”

“How about my kids?”

“Call them and talk to them. I don’t see a downside to this, Robert, and you are the only person who has a problem with this issue.”

“The only thing a transgender woman can’t give you is children. And you both already have kids. Is this a problem?”

“No.”

“So, think to yourself, this is a woman you like, and even though she was once a man, she seems to no longer resemble one or act like one. You told me she transitioned almost four years ago. She sounds like a woman to me, and you have to adjust your attitude towards her if you wish to continue your relationship.”

“Yes, Doctor.”

“Well, our session is over. All I can say is Sandra sounds like a fine woman, and you are lucky to be in a relationship with her. But you must realize that on your own, and I can’t do that for you.”

I left the psychologist’s office, and I was more confused than when I started the session. "It was up to me, she told me, and I had to come to terms with this." I called up my kids and arranged to have dinner with them at a nearby restaurant. I told them I needed to talk with both of them, and we agreed to meet up. I met my kids in the restaurant, and we ordered some drinks. I asked them,

“What do you know about transgender people?”

They both looked at me with a bit of surprise and said, “Trans people realize that they are the wrong physical gender to whom they identify in their mind, and it seems there isn’t a lot Transgender people can do other than become the gender they desire by changing their bodies.”

“Do you know anyone like that?”

They both told me they had met transgender students, both male, and female, in college, and it seems to be much more open now than it used to be.

“Well, kids, I am asking all of this because I recently met a woman that I enjoyed being with, and last week she told me she is transgender and transitioned into a woman almost four years ago.”

They both looked at me and said, “Wow! So do you want to marry her?”

I replied, “I wasn’t sure what I should do, including breaking up with her.”

“Dad, don’t be so uptight about this. It’s no longer a big deal unless you treat it like that.”

“I know, but it’s hard wrapping my head around this. I don’t know what I should do, part of me wants to fall madly in love with her, and another wants to run away from her.”

“Physically other than being on the tall side, she looks like a woman in every way; I mean, I have seen her naked, and -”

“TMI, Dad, we get it; she looks like a woman, not like a man. So, what’s the downside to all of this?”

“It just bothers me, and I don’t know why. I do love this woman, but I am unsure I can move past this transgender thing.”

“Well, Dad, all we can say is suck it up and get brave, and don’t believe that loving this woman affects your manhood in any way.”

“Yeah, I guess you are right about this; your old man is just being foolish again. Has either of you heard from your mother?”

They both shook their heads.

I wondered what was up with my ex-wife; it seemed she wanted to stay away from all of us. I have no way of contacting her. She never gave me a forwarding address or a phone number, and I thought we had a better relationship than that.

“Well, if she ever decides to call either of you, please let me know.”

I hugged my kids and said goodbye to them, and drove back to my condo. I had a lot to think about, but it only came down to one thing. "Could I date a transgender woman and not get so hung up about it?"

Sandra

Friday night rolled around, and I still hadn’t heard from Robert. I was hoping he would call, but it didn’t seem likely with my track record. I figured he had bolted like all the rest of the men I had met. It appeared their fragile male egos couldn’t withstand dating a trans woman. I felt, hey, it’s their loss. I have done everything to become the best woman I could be, and if it wasn’t enough for them, then so be it. Maybe I was destined to stay single. I hoped this wasn’t the case, but if the last four years had taught me anything, it was not to expect anything different from men.

At 7 pm, I still hadn’t heard from Robert, so I ordered a pizza and ate at home. I debated whether I should call him, and a text message appeared on my phone, and it was from Robert. I opened it up, and he apologized to me and asked me to give him another week, as he was still having conflicting issues that he was trying to resolve.

This text was a first for me. Robert was the first man who ever responded to me after telling them I was transgender. It wasn’t the message I was hoping for, but at least he was still working through his issues

Saturday came, and I cleaned my place, did the laundry, and then went for a drive on Saturday afternoon since it was a beautiful day for a ride with the top down. I stopped for a sandwich on the way home and thought, "At least I like my own company."
On Sunday, I finished up a project for work and watched a movie on cable. I wasn’t going to worry about Robert. I told him how I felt about him, and it was all up to him now whether he could accept me for who I am. Robert was the closest guy I ever had, which could have turned into a long-term relationship, and I figured maybe the next guy would accept me if he wasn’t the one.

Robert

The week went by quickly for me, and I was still constantly thinking about Sandra and what I should do about her. On Thursday evening, I went out for a couple of beers with an old colleague I first met on my first job out of college. We had kept in touch over the years, and I wanted to ask him what he thought regarding trans people.

Nick and I were knocking back a couple of beers, and I steered the conversation around to trans people, trying to gauge his feelings on the subject.

He looked at me and laughed. “Yes, I have known a few trannies over the years, though I suppose I shouldn’t call them that anymore. Why do you ask?”

“Well, I am in a quandary. I met a fantastic woman that checked all my boxes; I mean all of them. But then it turned out she is transgender, and it’s messed me up. I don’t know what I should do.”

Nick smiled and asked me, “Is she attractive?”

“Yes, she’s around six feet tall, has long honey blonde hair, bright green eyes, a slim build, and has very nice lips. She’s not huge in the breast department, but they look good on her.”

“Is she hot in bed?”
“Yes, very much.”

“Is she smart or a bimbo?”

“Smart. Probably smarter than me.”

“Does she have a job?”

“Yes, she probably makes more money than I do.”

“How is her personality? Is she high on the crazy scale?”

“No, she is rational and is very pleasant to be around.”

Nick intently stared hard at me. Then he reached over and smacked me on the side of my head.

“Ow! Why did you hit me?”

“Jesus! What the hell is the matter with you? Rob, you have found the perfect woman, and you don’t want to date her? Women like that are unicorns! So, she had a minor birth defect? Why are you letting that get in your way? I thought you were smarter than that.”

I rubbed my head. “Yes, I guess you have a point, and I have been looking at this the wrong way.”

Nick laughed and said, “Well, duh! Go after this girl; you will never find another woman like her. And if you are stupid enough not to go after her, give me her number. I know a hundred guys who would love to meet her.”

And with that, he ordered us another round.

I made it home late that night and crawled into bed

Sandra

It was getting towards the end of the week, and I still hadn’t heard from Robert. I was hoping he would call, I wasn’t holding my breath, but I was still hoping for the best. One more day and I might know for sure.

Well, Friday afternoon came, and I was finishing up at work, ready to go home for the weekend. My phone rang, and I looked at the display, and it was Robert.

“Hello?”

“Sandra, this is Robert. Are you able to talk now?”

“Yes, Robert, I am in my office, and the door is closed.”

“I first wanted to apologize for stringing you out for so long. It wasn’t fair for you.”

“Okay.”

“Look, we had a great time together, and I let this male ego thing get in the way of our relationship. I literally had to be smacked on the side of my head to realize this, but Sandra, maybe I shouldn’t be saying this so soon, but I like you a lot, and I won’t let a minor birth defect get in our way.”

I thought to myself, “Now that’s an interesting way to explain it; I will have to remember that one.”

“The point is, even though we have only known each other for a short while, I think I am falling in love with you, and I don’t want to lose you.”

I didn’t know what to say. “I never had a man call me back after telling them I was transgender.”

“Are you sure?”

“Yes, Sandra, I am sure. I wouldn’t be telling you if I wasn’t sure. I made reservations at The Florentine for 7 pm, and I will see you there, so please wear something nice. Goodbye, and I will see you tonight.”

Then Robert ended the call.

“The Florentine was the most expensive restaurant in town. I wonder how he even got reservations for the only Michelin 2 starred restaurant in the state?”

“Wow!" I was wearing a smile from ear to ear. "He just said he’s falling in love with me!”