The last four months have been absolute hell. Ever since I was sucked back into this lifestyle, I've been feeling so lost and I'm worried my marriage is starting to suffer from it. I haven't told Kat yet, how could I? She fell madly in love with this guy with a beard, who, while I never had an overwhelming sense of masculinity, I always did my best to be as manly as I could. How can I crush that image in her eyes, of the man she married just over a year ago? And even if I could tell her, I couldn’t tell her when I first knew… a week before her birthday. I couldn’t tell her after her birthday, with Christmas just 2 weeks away. And of course I couldn’t tell her after the holidays, and break her heart just a month and a half before Valentine's Day.

But now it's February 17th and I'm out of excuses, since "I can't tell her before President's Day" doesn’t really hold up. I need to do something about this, and I need to do it soon. Yesterday, I told my mother, it was my second time coming out to her; as I came out back in 2002 before promptly climbing back into the closet. She, as expected, was overwhelmingly positive about it all; although I'm not sure she fully understands the entire concept. She will in time after a deeper conversation, but until then, everything is ok. I'll deal with my father when I'm more confident about who I am, I know he'll be accepting of things, but it's still awkward trying to talk to him about something so deeply personal.


I wrote Kat a letter; I spilled my heart into it, then erased half of it and rewrote it. It's saved in my email, but I'm not sure how to deliver it to her… or if I should. It has to be today, we're both off of work, and both of my parents are at work. It really is the perfect day to have such a deep conversation. But, is it a perfect day to potentially bring upon the end of my marriage? Is there ever such a time? Part of me didn't even know the extent of it yet… was I transgender? Was I just a crossdresser? Could I open up to her about me deepest feelings about myself when I wasn't even fully sure myself? Fuck it… it's time.

"Hey sweetie," I said, just barely a whisper. "I have something I need to share with you. I'm going to send you an email. It might not be easy to read, but please read the entire thing before you say anything. I see that look in your eyes, I promise you now that this is not a breakup letter. I love you so much, but I need to share this with you before I go mad." I hit send and debated if I should leave the room. Instead, I stayed put an as her phone beeped, I felt my heart stop. The silence was deafening.

Photo by Kaitlyn BakerUnsplash

Where do I start?

Please know that this doesn't have anything to do with our relationship and I don't want anything to ever have a negative effect on us. You have known that I am bisexual, but one thing that I never told you about is that when I was younger, I was interested in crossdressing for a while. I collected a bit of clothes that I had hidden in my room upstairs and dressed up when I was home alone. For a short while, I had gone to therapy, mostly because it was something that I had long felt that I needed, but also, I saw a therapist who had specialized in gender issues and I quickly ruled out that I was not interested in major life changes or anything like that, mainly because reading about transgender people, it's a very common issue for them to have trouble enjoying sex and feel very negatively towards their genitals.

I enjoyed dressing up but never got involved in it as a major lifestyle, mostly because I never felt I could pass, so I avoided going further out of embarrassment. When I got engaged to Missy and moved to NH, I got rid of everything that I owned and forced myself to forget about it for a very long time. On occasion, the idea would pop into my head, but I suppressed the urge to do anything. But recently, and I have no idea what triggered it; the urges have come back and stronger than ever. It started with just casually looking at clothes on some websites that I liked, but before I realized, I started googling about crossdresser information and support. I found a website that offered support and forums for crossdressers and created a profile. I posted a little about myself and started chatting with some other members who have had the same feelings and such. I've made some new friends who have offered me advice and support that I never thought I would have for this matter.

As amazing as the support has felt, the one thing that has eaten away at me is that it's a part of me I am terrified to share with you. I fear that it will make you feel very uncomfortable, that it could be the thing that finally makes you feel disgusted with me and destroy us. But it's growing so strongly in me that it wouldn't be fair to either of us for me to keep it a secret. This is part of why I asked you to not always work the same days as I do. I need time to myself to really figure things out and to be able to express, even alone, this part of myself. I decided to go to therapy again because I have been a bit down on myself for the last few months. I've been depressed about our financial trouble and being forced to live with my parents, just as you are. I'm very torn about a lot of matters that I do not want to cause any deep trouble in our marriage. Britney has helped me a lot over the month that I've been seeing her, but there is still a lot that I need to delve into. I've been able to talk about all of this with somebody real, who understands the emotional struggles and can help me find the path that best fits the journey that I need to make… that I hope you are still going to be making with me.

I feel like this is a part of me that I cannot keep this a secret any longer. I fear that if I didn't share this with you, if I didn’t express that there is this part of me that needs some release. I love you, with all the madness in my soul. I hope you don't find yourself feeling negatively towards me. I hope that you are ok with this and it might be something that we could share with each other in time. If not, I completely understand and we will handle things however necessary.

Photo by Kev CostelloUnsplash

I waited while she read the email; it felt like an hour had passed. Finally, Kat looked up from her phone with a mixed look of love, sadness and confusion in her eyes. She grabbed me by the hand and pulled me to her, as her arms wrapped around me, I could feel the tears beginning to form in her eyes.

"I don’t want to lose you," she whispered.

"I'm not going anywhere," I promised. "I'll be here as long as you'll have me."

"That's not what I mean; I don't want to lose YOU… I don't want to lose my husband."

Over the next few hours, words were shared, tears were shed. We both admitted our deepest fears for our future together, and in the end, Kat promised to keep an open mind, to see how things go as my journey progressed and to try and accept the new me that may be coming, whoever that turned out to be.


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