Hey everyone. First post here. I googled how to tell my wife I'm transgender and ended up here. Sorry this is going to be long. First a little history. I remember being curious about "girly" things from about age 4. I wanted a baby doll and my parents indulged me. Her name was Christie. By the time I was 6 my parents had divorced and my mom had remarried. My stepfather did not like me acting or doing anything girly. I learned it was bad and tried to be a good little boy. When I was 10 we moved in with grandparents and my grandfather was like my stepdad on steroids when it came to "making a man out of me". My mom and stepdad divorced when I was 11 and we moved out of my grandparents' house when I was 12. Puberty hit and noticing the changes I and my peers were going through awoke my curiosity again. I took a few things out of my mom's closet that I knew she wouldn't miss and would dress up after school before she got home from work, always being very careful to have everything put away before she got home. At 14 I dressed as a girl for Halloween. My parents thought it was funny but otherwise didn't say anything. I continued dressing in secret all through high school but my sister was getting older and I would have to babysit her after school most days so it was difficult.
At 19 I decided it was time for this stupid crossdressing phase to end. It was time to be a grownup and this didn't fit. I'm sure my conservative, conformist family had a lot to do with this decision. I only had a couple of outfits and a bit of makeup so it wasn't a huge deal. If only we'd had the internet back then but c'est la vie. I didn't have a name for my female side back then but I put her in a box for almost two decades all the same.
A little over five years ago she climbed out of the box and said "remember me?" At first I was confused and angry. Who the hell did she think she was showing up after all this time like nothing had happened? I tried once again to deny her existence, to put her back in her box, maybe with a sturdier lid this time. But with age comes wisdom and I soon realized that wasn't going to work. Well now it was the 21st century and we had the internet, so I set out to find what it all meant. I bought some of my own clothes and makeup and started experimenting again. Although those photos make me cringe it was an important step. I decided that if I was going to do this, my female side needed a name. My mom once told me that if I had been a girl she would have named me Jennifer. So that's the name I chose.
A few months later I met the woman who would become my wife. I didn't think much of my female side at the time because I was still trying to figure out what was going on. Once things got serious I knew I had to tell her about this part of me. But it was almost Christmas so I said I'd do it after. Best laid plans and all that. We were at a family gathering at my aunt's house and I was showing her some pics I'd taken of my sister and nephew. She swiped back one too far and found a picture I thought I'd deleted. Thankfully we were on our way out the door at the time but she asked me on the way out to the car if I was a crossdresser. She had told me never to lie to her because her ex did all the time so I came clean. She thought I was joking at first but I will never forget the look that came across her face when she realized I was serious. It was a long car ride home and when we got to her house I thought she was going to tell me drop her off and never talk to her again. I wouldn't have held it against her. But she didn't. She asked me lots of questions that night. Was I gay? No. Did I want to become a woman? No (because at the time I really thought that). By the next morning we'd figured out what it meant for our relationship and it became a standard don't ask don't tell arrangement. By this time it was January 2014. I had come out to a very dear female friend about three months prior. I made arrangements to visit her and her husband in Los Angeles (I live in San Diego) at the end of the month. It was Jennifer's coming out party, her first time in public. I bought a new wig and some new clothes and spent two days in LA as Jennifer. We went to an art museum and then that night bar hopping in West Hollywood. This may have been the beginning of the end.
When I got back my girlfriend was curious and asked to see pics. Of course I obliged. Her reaction was mixed but she didn't run screaming. She had the same conservative whitebread upbringing as I did so it wasn't a surprise. She's also very concerned about what others think of her. This will be important later. I continued to build my wardrobe and confidence throughout 2014 but only got in public two more times. In November she moved in with me.
She went out with Jennifer for the first time in May of 2015. We went to my favorite gay/transgender bar and I could tell she was a bit unsettled by all the other trans girls that were there. A couple of my friends were there and I made the mistake of mostly talking to them and ignoring my girlfriend. She said lots of very not nice words to me on the way home and didn't go out with me again for a year and a half. I continued to go out maybe once every month or two by myself or with friends. By this time I had made a separate Facebook for Jennifer so I could meet friends locally. I did not hide this from my girlfriend. I made every effort to be transparent so she didn't think I was hiding anything.
2016 was a great year for Jennifer. I started seeing a therapist about my gender issues. I got out at least once a month and my presentation improved immensely. My girlfriend and I got married in December after having a long talk about whether I wanted to transition or not. I told her not right now but I couldn't make any promises about the future. She asked if that was a gamble she would have to take if she married me and I said we were both taking that gamble. Of course at that point I expected that "the future" wouldn't rear its ugly head for a few years. So we drove to Vegas and tied the knot.
In 2017 I started going out twice a month when schedule and finances permitted and it was also the year I became comfortable with going out in mainstream public as Jennifer. My wife had come a long way in her acceptance by now and was of the opinion that she loved me and if that meant she had to put up with Jennifer now and then that was OK. By the end of the year her red line was I won't be intimate with you as a woman and if you transition I'm leaving. I assured her I was 98% sure I didn't want to. Except that figure may have been a bit high because I'd already been thinking I needed more Jenn time. Now in 2018 my therapist has switched her schedule so that I see her on Saturday. Which means it's almost always Jenn who goes. Two weeks ago I spent the whole rest of the day as Jennifer and went to lunch and clothes shopping after my appointment. My wife was a bit irritated with me for this but she got over it. This past Saturday I came right home afterward and had to take everything off because we were going to meet friends. I mentioned to my wife that it makes me sad when my girl time only lasts a couple of hours. She didn't take it well. My therapist and I had discussed my need to be Jennifer more and I had told her that if I were single I'd be doing entire weekends by this point so that I could experience normal life as a woman, not just going out shopping or with friends. Seeing my wife's reaction I kind of dropped the subject but I've been thinking about it all weekend. <y therapist and I both agree that Jennifer needs to come out more but I don't know how to talk to my wife about it. She has been dealing with depression because she was unemployed for almost a year (she finally got a job last week). She has really bad anxiety and always assumes the worst. And the sad thing is that I think it's a lot more likely that transition is in my future than I did even a year ago. And I feel like a jerk for that. My wife has come so far in her acceptance of Jennifer, even going out with her multiple times in 2017, sometimes even during that day. And now I have to tell her that even all that isn't enough. I love her very much and if we can't be together because of this it will break my heart. And hers. I know I would be very sad but would eventually be able to move on. I'm not sure I can say the same about her. She tells me all the time that she's glad she found her happily ever after with me after kissing so many frogs and I think pulling that rug out from under her would destroy her.
If you're still reading, thanks. If I'd known this a year and a half ago I wouldn't have asked her to marry me. But I thought I was just a guy who needed to be a girl sometimes. Now it looks like I might be a woman pretending to be a man and it kills me that I may have to hurt my wife through no fault of her own. She always says that wants a husband and not a wife and that she's not a lesbian so I'm not hopeful she would decide to stick around. We don't have kids so at least that's not a worry but it's still not ideal.
