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!!!!

Results from http://bdsmtest.org/

I guess this is where I stand with this particular BDSM survey

== Results from http://bdsmtest.org/ ==
100% girl/boy
100% Degradation receiver
100% Submissive
99% Bondage receiver
96% Pet
93% Masochist
86% Slave
86% Primal (Prey)
83% Exhibitionist
80% Experimentalist
79% Brat
75% Voyeur
61% Ageplayer
25% Non-monogamist
22% Switch
7% Primal (Hunter)
4% Vanilla
0% Master/Mistress
0% Brat tamer
0% Sadist
0% Bondage giver
0% Dominant
0% Daddy/Mommy
0% Degradation giver
0% Owner
0% All-Rounder
See my results online at http://bdsmtest.org/result.php?id=752038

Gettin' Jiggy Wit It

We got CRAZY! Soooo crazy on the dance floor!

Last Saturday we made it back to the LGBT friendly club Hamburger Mary's for the first time in three or four months for Jamie Jameson's monthly TGirl Saturday dance party. Our summer schedule really different and crazy as far as little free weekend time and we just couldn't get a night free to make 'til now.

We got ready, with our usual preparations, with Miss doing both our nails very pretty as always :-D

My outfit was a black top, white and black skirt, black polka-dot thigh-high stockings  (my toes were painted red), 'featuring' black thong panties (LOL!), and the white tipped finger nails Miss had put on for me (there is a whole process to what she does there).

The top was a little different than the picture below and I wore different jewelry, but the rest of the outfit was the same.

I've gotten more confident going
out to the club in shorter skirts!

Oh, and I have to say that Miss was looking dynamite sexy herself, in a blue lightly sequined top with cutouts at the shoulders and ripped blue jeans - Yummy!!! 

It's a real thrill to be able to dress sexy and be out with Miss as girlfriends. I can't tell you how joyfully happy that makes me feel. I get a big dose of hope that I'll be full time one day :-D

We get to the club a little after 8 and park across the street. I actually like that better than parking in the garage behind the club as it's a lot more public and I just don't get enough "out in public" time while I'm en-femme.

We have our IDs checked at the entrance and are escorted to a table with a great view of the dance floor and the overall club. We order dinner which as always was just delicious (I had salmon with vegetables). Of course we also got going with Margarita's.... and we kept them coming.

While we are eating the music is going and people are starting to get out and dance. About 9:30 Jamie kicks off the party proper and introduces the featured dancers, and the dance floor starts to get more crowded. We both take turns using the restroom so we don't have to worry about loosing our table if we are both gone (but I'm sure we wouldn't have). No bathroom issues here - I've never been in the men's room at the club - hehehe!

After that Miss says she is ready to dance. I suggest that we get our picture taken first on the "Red Carpet" but she is insistent that now is the time to dance - so off we go!!!

So we are dancing with each other and having a great time. I think I'm better at dancing in heels than walking in them, but I don't think I had any major faux pas in the walking department - at least not that I can remember!

Here is where the 'Jiggy comes in. And that's almost a literal 'Jiggy, as I'm about to try and explain. 

A guy works his way towards us while we are dancing. He was very polite entirely by the way. He starts to dance next to us, so I think cool, I'll be friendly and dance a little bit with him. This is the 2nd or 3rd guy that I've ever danced with by the way. 

It was obvious that Miss and I were dancing together, and he also moved towards Miss and danced with her too. So basically the three of us were dancing together at one point. And he was so polite that he even asked if it was ok for him to dance between us, which we both said 'yes' of course.

So I am having a great time, we're all dancing together and he's taking turns with both of us. As he and I are dancing we start to get 'Jiggy! I mean REALLY JIGGGGGGY!!!! It's Dirty Dancing time. He starts to dance all sultry and sexy with the whole facial expression thing going on. I get into it and encourage it a little with how I'm dancing. He gets more confident and ups his game with me at this point. I'm thinking to myself - Oh my god, he's really turned on by this! My inner attention whore is both amazed & incredibly flattered, but also in disbelief!

Things continue to get more and more uninhibited. Did I mention that Miss and I are both pretty inebriated from all the alcohol we had been drinking? He dances closer to me, and I put those sexy nails that Miss did for me to good use. I teased his shoulder and back from behind with my nails while he was dancing with Miss. He has a button down shirt that is mostly unbuttoned. He backs into me a little and I reach around him and start to tease his bare chest. I'm thinking he's really enjoying this, don't you?

He switches back to dancing facing me. At this point Miss starts giving me the "thumbs up" sign so I know she is giving me the OK for what's going on, but I'm not really sure where her line is with as far how far this should go. So in "dance style/fashion", one of us (I don't remember who) starts to straddle the other's leg in that sexy dancing teasing/pelvis grinding way (but no contact at this point that I remember.) I am looking at Miss and she's still giving me "thumbs up" so I go with it and we are just going crazy. 

He turns back to dance with Miss and I can tell he's dancing close to her. He did that for a while, then he backed towards me and started to press his butt back into me as we danced. I'm going with this crazy moment still, pressing my pelvis back against him, teasing him with my nails. I'm lost in the moment (and the tequila) at this point but I'm still looking at Miss to see if I'm going too far or not for her, but she is smiling and all is good. 

Then our man starts to feel me up, running his hand up along the inside of one of my thighs to the top of my stockings. I'm thinking I hope I don't get aroused! Well, I'm letting this happen, in some kind of attention-whore-tequila-shock, so I just keep dancing and letting it play out because I have never been in this kind situation before. Not ever, not even as a guy. As a guy I never had the "guts" to dance with a girl and feel her up as I "knew" she would immediately reject me. But as a girl I have to confess that I was eating this attention up.

OK, so guess what, he eventually goes for the prize. Very gently he works his way all the way up my skirt and starts to fondle me along the sides of my thong and then underneath it. I am totally at a loss as to what to do. In (flattered/amazed?) disbelief! Other than a doctor, only one other time has a male touched my privates. That was a friend/fellow Cub Scout when I think I was 8 years old (but that's another story).

Eventually he turns to me and asks me if he can suck me off!!!! The first time he asked I just smiled not knowing what to say. Then he asked again and I kept smiling kindly and said I'm sorry and shook my head. 

What I didn't learn until later was that he was trying to get 'Jiggy with Miss too! He was trying to feel her up, but she doesn't have a 'Jiggy! He asked her if he could suck her off also! Going for the threesome? Miss told him she was sorry but she didn't have one of "those." Butt she did tell me she was flattered that he thought she was a trans person!

I came to my senses a bit, knowing this wasn't going to go any further (and not wanting it to), so Miss and I took our leave of the dance floor and headed up to the Red Carpet to get our pictures taken, and we left the club after that.

This was a wild experience let me tell you! Miss and I both had a great time. OMG!!!!

I hope 'our man' didn't feel lead on.