Well let's see, story time:)
Over the past few years, I had started exploring my sexuality more. This came about as a result of my our unsatisfying sex life. From the get go (Honeymoon) we had difficulty having sex. Well, I had difficulty having sex. I had a hard time keeping it up during sex and didn't understand why. I loved (still do of course!!) my wife and found her sexually attractive. We were both virgins as well. I chalked it up to being inexperienced at sex for a while but after things didn't really get better over some time, both of us began to wonder what was wrong. I went to a urologist who said everything was fine, I was told to relax, just let it happen, etc. Nothing really worked. I could, thankfully, bring her to orgasm in other ways but, intercourse was a constant frustration. That obviously led to my wife having some self esteem issues. She even told me to think about whatever or whoever I needed to think about during sex in order to stay hard. There were also the issues of learning to live with another person 24/7. Long story short, it was a VERY rough beginning to our marriage to the point where we both wondered if we were going to make it. We were also trying to get pregnant and ewre obviously NOT successful since I had such a hard time keeping it up during intercourse.
I did a lot of soul searching during this time, trying to figure out if I was straight or gay or what. Thankfully, I never chose to experiement with other people to try and find that out. I did however, come to the realization that I was Bisexual. This understanding put me in a much better head space obviously and led to me being able to have better intercourse with my wife. I think it was the result of me not having a hidden subconscious sexuality anymore. I understood who I was and accepted it. I didn't tell my wife yet however.
Now that I was mentally free to fully understand myself better, I started decided to start buying clothes that more fit with my new understanding of myself. I started to dress nicer (my wife always used to say that I had zero sense of style) and take care of my body better, working out more. I also began to get sexier male underwear for myself as well.
After a short time I began to naturally gravitate more towards cute looking male underwear (xdress .com has been instrumental). I got really into their panties, wearing them most days. My wife knew (I didn't even try to hide that from her) and was seemingly okay with it. After that, I started branching out into their babydolls and bras.
One afternoon, not too long after that, we were having a conversation about sex, and it turned to orgies, I think. Her, being totally grossed out by them. She asked how I felt about them and I told her, honestly, I would probably be all about it, trying to have as much fun as possible; hypothetically of course lol. She then asked me if guys were there, if I would mess around with them also - and yes, I think my wife probably thought I was secretly gay, probably before this conversation - I thought about it; honestly thinking about the enormity of that moment in our relationship, and told her that yes, I probably would. Much to my surprise, and my heart beating seemingly a million times a minute, she didn't freak out. She asked more questions...oral? anal? giving? receiving? We had an amazingly honest conversation and during that conversation I came out to my wife as a Bisexual man. And yes, I know I am Bisexual even though I have never slept with or even kissed another man. I simply AM.
Again, not too long after coming out to my wife as Bisexual, my bras and panties weren't enough for me and I found myself longingly looking at the women's clothing when we would go shopping. I started looking into crossdressing, what it is, what it means, what it doesn't mean, etc., and found myself feeling I should explore it more. I began wearing tinted lip balms and dropping hints to my wife about "oh how pretty that makeup looks", "oh her eye shadow is amazing", "omg, I love her brows!" and watching makeup youtube videos with her (she LOVES makeup and is fantastic at it) forget exactly we crossed that barrier about me wanting to try wearing some but that happened. I was also growing my hair longish at the time (she loves it long) and I would tease it up in different ways around the house.
Long story short, we were out shopping at Banana Republic for clothes last November during black friday weekend and as we were getting some new clothes, I asked her if she could but this cute little set of a plaid strappy top and some cute little shorts (from the women's side) she gave me permission and purchased them for me. Ever since then I've been all in, came out to her as a Crossdresser, and life has honestly never been better for us as I am not hiding anything from her and I can truly be myself with her.
She is okay with me Crossdressing inside the house but not okay with me telling others and going out as a woman. She doesn't want to deal with how people will view and judge her as the wife of a CD, and I understand and accept that.
So yeah, I think that is pretty much my story in a not so short nutshell:) If anyone has any questions, please feel free to ask!
