Re-uniting, Coming out to Miss, Breaking up again, Re-re-uniting

Backstory
Soon after high school, when I was working my way through college, Miss and I had dated briefly. My immaturity was the reason we split up. But we did have some fun times, and I'll have to write about that down the road.

After we split up, we didn't have any contact at all. We both got married (to other people) and had kids. During that time I fantasized about her all the time. Weekly, daily... I was still in love with her. There were many times I remember fantasizing I was with her while I was having sex with my ex. Sometimes that's what it took for me to be able to climax.

This was long before social media sites existed (mid-to-late 1980's), so in my heart I knew I never was going to see her again. I had no friends or acquaintances that would have known where she was or how to contact her.

Miracle time
Around 2002 I had come across the classmates.com website. That site had gotten high school class rosters and made them available online. You could sign up as "yourself" and send email through the site to other people. I checked it out, and eventually I decided to try to contact her. I sent email through the site, but I never in a million years expected her to have found that site or signed up on it as this was really early in the Internet's growth. Plus I figured she was happily married and probably wouldn't be interested in me even if she wasn't. But a miracle did happen, and she emailed me back!

I Internet stalked her somehow, and got her approximate address. It looked like it could have been a housing track, so I definitely assumed she was happily married.

As I eventually found out yes, she had been married and had a child but had divorced. But now she had a boyfriend that was living with her and her daughter. I was still married.

I don't recall all the specific details of what happened back then, but via email we setup a phone call, we ended up talking on the phone, and that lead to a "let's meet in person."

The arrangement was for me to meet her at her office at lunch time. I was incredibly nervous, and the anticipation and excitement about actually seeing her in person was driving me crazy! I could not wait!

So we meet again
I arrived and went to the receptionist and said I was here to meet Miss (well, using her real name). A co-worker took me back to where she was.

When I first saw her I was scared that this was just going to be a "hi how ya been" kind of casual meetup. But our eyes met, I sensed something good but I couldn't tell you if it was inside me or something I sensed coming from her. We walked toward each other and ended up in a nice big tight hug! I died! I was in heaven! She wasn't rejecting me or holding me at arms length. Wheeeeeew!!!

So I felt hope that I could have her again, one day, even though we were both still attached. We continued to meet for lunch at her office regularly. It was so so nice! A second chance with the woman of my dreams!!!

After not too long she split up with her boyfriend, and I was able to visit her at her house.

Coming out
I was wearing pantyhose under my pants regularly, and had been doing so while visiting Miss at her office. At this point in time I had no conscious thoughts about being transgender. No gender dysphoria awareness. In fact, I was so naive at this point that I thought "shemales" were not actually real. They didn't exist, it was all doctored photographs. I didn't mentally connect Billy Jean King to gender transition at all. This was just back in 2002!

So here I am, on the verge of a dream come true finding Miss again. But inside I have stress about my cross dressing secret. If I told her would she reject me?

I sent her a porn picture of  a transgender girl in a cheerleader outfit. I don't remember what I was thinking when I sent it, but I did. She didn't react to it that I recall, but sometime later she said she wondered if I was trying to "tell her" something. I guess I was, but it wasn't conscious.

Eventually, while meeting her for lunch one day, I got the courage to confess. I did it because I didn't want to keep any secrets from her, and because I knew I could not stop enjoying wearing women's lingerie. I needed to know sooner than later if she would accept that about me or not. Well, she did accept me, and my cross dressing.

Miss Double downs!
Miss did far more than just accept my cross dressing. She took me to a whole new level of self-understanding about my gender identity. I don't think that was her goal, but that's what happened.

She encouraged my dressing up. I think one of the first things she did was to pick out a full outfit for me from her own wardrobe, including some cute panties with a strawberry print pattern, and had me try them on and wear them at her place. She bought me lingerie and we did photo shoots so I could see what I looked like. For my birthday she bought me my first dress! OMG that is the birthday gift I remember out of all I've ever received.

I was in heaven, and doing things I never imagined for myself. I was experiencing being able to fully dress like a woman, and I had the woman I loved completely accepting and supporting me with it. I was getting excited about life, and looking forward to the future, instead of just "marking time" in life with someone I should have left years earlier. But that's a whole different story.

Blowing it with Miss - so much for second chances
So I told my wife I was leaving. I packed my things and moved in with Miss. It was the hardest thing I had ever done, leaving my kids. In high school I had promised I would never abandon my kids like my father had me. And I had shared that sentiment with Miss back then too. Telling her that then, may have been the single most important thing that made it possible for us to be together today. Because she already knew about the promise I made to myself about my kids.

I was with Miss for little more than a day or two before I could not take the sadness and depression of leaving my kids. I was a sobbing, crying, broken wreck. I had to go back to them. I couldn't leave them, even though it was going to mean I would never have the woman I had already loved (in absentia) for 20 years. A woman that actually enjoyed me being feminine. The woman that was unlocking my real self, my real feminine self. My highest most personal (selfish?) dream was to be with her, but I had promised myself I would not leave my kids.

So I went back to my horrible married life. Sacrificing myself for my kids. Turning my back on the biggest dream of my life - Miss. It was not a choice, it was just what I, as a responsible parent, had to do.

I could never expect Miss to want to have anything to do with me again. This was the last shovel of dirt on the coffin. She had given up her boyfriend for me. I made promises to her and broke them.

She got back with her boyfriend and they married (I learned that a few years later). I was back in my unhappy marriage, "marking time" again. I probably thought that when the kids all move out I can end the marriage and go from there. But I knew Miss would not give me a third chance. She had moved on.

3 years go by: Re-re-uniting
I was living my miserable life, working long hours probably because that meant less time to have to spend interacting with my wife. I thought all the time of how I screwed up my 2nd chance with Miss. Any progress in me as far as gender dysphoria was concerned was also gone. Yes my wife knew of my cross dressing, but she wasn't interested in it. She just put up with it.

I was working at my desk at home on a Saturday morning. I get an instant message from Miss. My heart pounds jumping into hope again that Miss might still care and want me somehow. I message her back........

I'll have to work on the next chapter of our story in a future post, but yes we did get back together for a 3rd time!... But can you believe it, we also went to the brink of breaking up a third time a while later! Don't worry, we are totally good now - Whew!!!!