For the most part, my relationship with my family is less than cordial…we talk sometimes on holidays but there is little love or trust among us. When some of my tendencies came to light, there was a lot of bad blood and harsh conversations that led to a very strained relationship. Years have softened the blow somewhat, but its almost impossible to regain trust and affection once it has been abused and destroyed so completely.

Unfortunately my family is heavy on my mind tonight as I sit across from the lady I love. Sharon is a couple of inches taller than me, which means she also towers over most guys when she wears heels. Her hair is a dark red color and comes down past her shoulders when she wears it down. Her eyes are a bright green, and have an alertness that shows her intelligence. Her body is in excellent condition, but still has all the luscious curves a man like me dreams of. Anyone who judges a woman on a strict physical appearance scale would probably give her something in the range of an eight…but in my mind she is at least a twelve on a scale of ten. In other words, she is completely out of my league. But even more important in my mind is what you don’t see…her intellect, her spirit, her personality. Who she is is so much deeper than just the enticing smiles she gives or the graceful movement as she walks…its also how she can make anyone feel like they are the most important person in the world.

Yes, she is completely out of my league, but I have come to love and trust her more than anyone in my life. It is finally time, and I am more nervous than I had ever been before. I find myself looking into the eyes of the woman I love more than anything terrified of her response. I didn’t go the cheesy restaurant scene or the way overboard public announcement type scenario. I didn’t want to bully her into anything or force a response due to overly dramatic settings. Instead I went for simplicity. A well cooked meal (yes I am a good cook) in my apartment with a bit of music playing and pleasant talk. And after we both contentedly sighed and moved into the living room, I got down on one knee and asked the question.

Her expression quickly cycled through several emotions. I could read the excitement, joy, desire and then finally doubt as she processed my proposal. She didn’t say anything for a minute, then another and I felt it dragging on…and somehow I knew she would deny me. Finally she spoke.

“No, not until you tell me.” She wasn’t cruel in her response, but she was quite firm.

“Tell you what?” I asked.

She looked at me and with a hint of anger replied. “You know what. You have a big secret that you are scared of me finding out, and until I know what it is there is no way I can marry you.”

I held back a sigh, as I felt our relationship heading towards a catastrophic end. I had tried to share my secret in the past with other girlfriends and every time it ended things. Sometimes it was a rapid implosion where I never got past the basic explanation, other times it devolved more slowly until I was treated as less than a man…as if my habits made me unequal or undeserving of respect. I mentally sorted through my options.

I could lie. But that would shatter any bonds of trust between us. And either now or in the inevitable future where she found out, she would vilify me for not being honest with her.

I could end things now and hopefully maintain my dignity.

Or I could tell her everything, and pray that my judgment of her character was not flawed.

Fearing the worst, but praying that just once God would have a little mercy on me I did the bravest thing I had done in years. I told her everything.

Finally, after a long, emotional conversation I had myself and all my secrets laid bare before her. I had given her all the weapons she needed to destroy me mentally, socially and financially…and now I was literally at her mercy.

She looked at me, and I could not understand the emotions I was seeing. I did my best to prepare myself for annihilation, but after a bit she said something no other woman had said to me. “I want to meet her before I decide. Next weekend we will have another date where you introduce me to her. It’s my turn to cook.”

——-

The best description for my feelings is shock. When Daniel told me of his penchant for dressing as a woman, my expectations were pretty low as to the final product. I was expecting a man in a dress to show up for our date, instead here was a sexy goddess who I would have never recognized on the streets. She (there is no way to even think of her any other way) was to all outward observation completely feminine from the long, jet black wig…right down to the sexy black heels on her feet. Everything was put in place perfectly, and I realized that there was no way this was just an occasional dressing out. Every movement, every action, everything she did portrayed a femininity that overruled my recognition of her as my Daniel.

I had to push down my inner lesbian and keep myself from dragging her directly to the bedroom. We had things to discuss and I couldn’t go distracting myself just yet.

After a few awkward minutes of dancing around the elephant in the room I finally blurted out, “Are you gay?” If her immediate and definitive “NO” was not enough, the slightly disgusted look on her face tipped the scales. We talked for a while and eventually I became as relaxed with her feminine persona as I was with his male one. As the discussion went on I came to understand that were the option available she would probably have transitioned, but due to financial and social reasons she never went that route.

It was only after we had been talking for several minutes that I realized I wasn’t sure how to address her. I think the question caught her a bit off guard, but she also seemed faintly pleased that I cared enough to ask. I was expecting one of the more obvious names like Danielle or Dani, but she told me she goes by Diane while en femme.

We spent the evening talking about a wide variety of things, from our secret hopes and dreams…to our deepest desires. I admitted to her that I was in fact bisexual, while it had never been an actual secret it wasn’t something I advertised on a daily basis either. She told me about the rejection of her family and how badly it hurt her.

Eventually we managed to get to the heart of the matter. There were a few things that we needed to deal with if we were going to make it as a couple.

First, Diane was (from my perspective) unable to truly embrace and enjoy being a woman. While she had the look down to a tee, she still felt uncomfortable and unreal. I had to calm my inner kitten as I imagined all the delicious ways I could bring her out of her shell. I decided then and there wherever things went with Daniel, I would do my best to remain friends with her and help her realize her potential.

The second thing I noted, was Daniel didn’t want to be treated as or viewed as less than a real man. When he dressed like a man, he acted like a man and wanted to be treated as a man. Of course, at least in my mind, he was the biggest offender in breaking that rule…he failed to see himself as a “Real” man and often did things to sabotage himself. I would definitely have to push him in his Daniel persona, or convince him to be Diane full time (yum). Either way, he definitely needed some pointers on what makes a “Real” man as I find his demeanor far more appealing than the other “Real” men I have known…

——
Examples.

My first “Real” man was my father, and his manliness was asserted by coming home drunk and beating his wife and daughter on a regular basis. As ashamed as I am to admit it, the happiest day in my young life was when he died from a stress induced heart attack when I was thirteen. Maybe the fact that he died while beating my mother so bad she required weeks of hospitalization was enough to salve any grief I might have known otherwise.

——

My second “Real” man was this nice, sweet basketball player at my school. He wooed me for weeks, telling me all the sweet little things that made me melt inside. It didn’t take him long to convince me (with my lowly self opinion at that time) that he loved me. I didn’t just give my virginity to him, I threw it at him with reckless abandon. Three days later he broke up with me.

The weeks that followed were nearly as horrifying as things had been when my father was still alive and kicking (sometimes literally). The biggest difference was that this time it was all psychological abuse. The rumors started almost immediately about how I was a slut who would have sex with anyone. My so called friends dropped me faster than you could say go. Guys started groping me in the hallway when I walked by, while girls sneered at me and called me names (which I will not repeat here). All at the same time my ex-crush was being lauded as a stud and had everyone treating him like he was some type of hero. Imagine, at the same time I was being vilified, he was being worshiped for the exact same act. I didn’t take it well when I overheard him bragging to his friends about me.

I learned three things from that relationship. One, the only person who I should allow to validate my existence is me…flattery is nice and all, but it just doesn’t beat self esteem. Two, if you are going to punch someone in the face, at least get training first so you don’t break your hand. And finally, people are shit. That is people in general, not specific people (who can sometimes be decent), but people as a group are just shitty. In less than a week I went from being in love and having the best experience of my life, to being a social outcast and having my heart crushed.

——

I met my third “Real” man some years later in college, although to be clear, he was actually a she. She was a very pretty woman, even though she did her best to downplay it by wearing men’s clothing and keeping her head shaved close. In the beginning things were nice.

She was aggressive and took the initiative in our relationship…while I was more passive and just went with things. In her eyes I was the only girl in the relationship and she made sure I knew it. Over time she became more oppressive and controlling, eventually getting to the point where she started telling me a woman’s place and a woman’s role. I went along with things for a long while, I guess on some level I enjoy being in the submissive role with women…but eventually she pushed too far. I don’t even remember why she slapped me and called me her bitch, I do know that she ended up with a hospital visit while I got 100 hours of community service and a mandatory anger management class (apparently my knowledge of martial arts made things a bit more serious.)

The biggest take-away I had from this relationship is that submissive does not mean doormat. While I enjoyed the submissive role with her, I was not a victim and would never submit to abuse. To me submissive does not mean weak, stupid or otherwise self degrading…it means that I will when it suits me (and only then) give control of aspects of my life (especially sexual) to another person with the understanding that there are limits on both sides as to how far that extends.

——

Over the years I had many relationships. Some ended in friendships, some ended badly, and some just ended. Eventually I just came to the conclusion that I should enjoy the good times and not get too caught up on forever with anyone. Oddly I found that my relationships with women always tended to have me in the submissive role (which I enjoyed), but my relationships with men were always best when I took charge and ran things.

——

My last memorable “Real” man was the new good ole boy supervisor, Jimmy (don’t call me James) they brought in at my last job.

I had been working at the firm for several years, and the team I was leading was one of the most productive in the company. When my boss opted for retirement, we were told that they would be taking applications for the position in a few weeks. Imagine my surprise when less than a week later they brought in Jimmy. While he had no experience in management or the job in general, he oozed charm and confidence (which was apparently enough). Obviously, the applications process was just another one of those talking points where they tell you something to distract you from what is really going on.

I wasn’t happy with the turn of events, but I also decided to at least give him a chance (it wasn’t his fault upper management was full of assholes). Over the next few weeks I quickly began to see where things were headed. He would take advice (not necessarily good) from the men on the team while practically ignoring anything any of the senior women would offer. When he wanted something from my team, instead of coming to me he would go to one of my male subordinates and ask them…or have them relay his instructions to me. Seeing where things were heading, I did the only smart thing for someone in my position to do…I began to document everything.

When he gave a new project to Michael, one of my subordinates without any collaboration from me…documented. When he excluded me from attending any of the project related meetings and calls…documented. When the project failed spectacularly due to easily rectified mistakes…documented. When I got called in to his office and officially reprimanded for said failed project…documented (and recorded on my phone).

I set up an appointment with his boss to discuss things, imagine my consternation when I walked in to find Jimmy sitting there as well. The meeting quickly turned into another dressing down and a potential demotion if I didn’t “straighten out”. Of course that meeting was documented and recorded too.

If things had only been bad on a professional level I might have just left it alone and found a new job. But that was only the beginning of the problem. While Jimmy was friendly with all the guys, he had a tendency to be over friendly with myself and the rest of the ladies in the office. He had a habit of getting just a little bit to close, looming into the personal space of the women. Every now and again he would “accidentally” brush against my ass or press up against me momentarily. He would often make loud offensive jokes about women or talk about his wild sexual encounters with the guys.

For me it came to a head when I came across one of the female analysts crying in the parking lot because she had been let go…apparently they needed to downsize our overworked staff two days after she had declined a date with him. Finally fed up, I went to the Human Resources manager and filed a complaint citing all the various issues that had been happening in our division lately. I told them everything that had happened, but I intentionally failed to provide them with the excessive levels of documentation I had been keeping (just in case). It turns out that was actually a very wise decision.

Imagine my surprise when I was met at the office doors the next day by security with a box with my stuff sloppily tossed in it. Apparently due to the failure of that project and my inability to work well with others I was being let go. Just like that after 5 years, walked out the door for a failure that wasn’t mine.

Apparently that anger management class helped me out because I didn’t punch anyone. I didn’t cut anyones tires or commit any other offense that while gratifying would have made things worse. What I did do was find the meanest, most fearsome sexual harassment attorney in the area and give her every shred of documentation I had from the last couple of months showing all the professional and sexual related instances. She of course took the case on the spot.

By the time the suit had been filed, the dragon lady (as I thought of her) had amassed through her own internal investigators, much more additional information that surprised even me. One, Jimmy had been recently fired from another position for sexual harassment. Two, Jimmy’s boss was also his uncle. And finally, the project they had been working on was actually part of a scam concocted by Jimmy and his uncle to steal nearly a half a million dollars from clients of the company.

Needless to say I received a very rapid and very generous settlement as long as I signed a non-disclosure agreement to keep my mouth shut about the details (especially the stealing from clients) of the case. The funniest thing about that was the fact that while I couldn’t disclose said information to the press and what not, I was still legally bound to testify under subpoena. Ironically, the analyst who’s firing had given me that final push decided to sue as well, and apparently she did NOT want a settlement. In the end I got my day in court after all…who says you can’t have your cake and eat it too.

I guess in a way, that was the best “Real” man experience I ever had. Now I am moderately wealthy and can choose what I want to do with my life.

——

Pondering on all of the time I had wasted with the perceived “Real” men was what decided me in the end. Daniel was polite, gentle, generous and honest…all traits that I personally find quite attractive in a man. In addition he was slightly submissive, in that he would generally go with whatever I wanted with a smile on his face. Overall, in my mind he was the perfect man (for me) and far more attractive than any of those so-called alpha types. I could easily see myself with him for the long haul, and I also could see myself having so much fun with Diane (assuming I could get her to let her wild side out).

It happened so easily and naturally I didn’t even realize I had made the choice, before I pulled her to me and gave her what was easily the hottest kiss we had ever shared. When I pulled away, gasping for breath, I absently noted that she looked so hot with that expression on her face and her lipstick smeared from our heated exchange.

I looked her in the eyes and told her what was on my mind.

“Yes, I will marry you on three conditions.”

She looked at me expectantly.

“First, I am the only one wearing a dress at our wedding!”

She blushed, and nodded.

“Second, you have to tell me where you got those shoes!”

She nodded again.

“And third…”

I grabbed Diane’s hand and led her to the bedroom, on the bed was one of those sexy maid outfits that has no practical purpose but to tantalize and tease. I felt her hand tense when she saw the outfit, and looked to see an expression filled with doubt and a touch of anger.

“You want me to wear that?” She said hesitantly.

“No silly, thats my outfit…if you want we can get you something in leather though.”

Her smile and the way she began to shift uncomfortably in her dress was all the answer I needed to know I had found the perfect partner.