Telling My Girlfriend

      My general rule of thumb is to avoid keeping secrets from your significant other, especially something as potentially significant as crossdressing. However, I understand there are sometimes reasons why maintaining those secrets make sense so I won’t say it’s an absolute rule, just one that I would strongly recommend following. There are also different degrees of crossdressing. If it’s a minor fetish that you might have, then the ramifications of not telling your significant other are quite different than if it’s a significant interest. For me, it definitely leans towards the latter.

      My dating history post-crossdressing has been very spotty. Looking back, I’m not sure if it negatively affected my ability to maintain a stable relationship, but I’m confident it didn’t help. The first real relationship after I discovered my interest in crossdressing was during my freshmen year in college with a girl named Amy¹. It was an extremely toxic relationship that unfortunately spanned the entirety of the school year culminating with her cheating on me with one of my friends. There isn’t much to say about that relationship aside from the fact that it destroyed my confidence. I made the mistake of putting her on a pedestal and as a result made every classic blunder in the book. Freshmen year was also the year where I started really building my girl closet, however in trying to keep a more masculine façade for her, I never contemplated telling her about the secret. These factors (along with many others) meant that when the relationship ended poorly it absolutely crushed me. For the next three years I fell in and out of multiple flings, but nothing ever progressed far enough to something that I considered relationship worthy. This wasn’t entirely a bad thing either as I was able to fill the gap with more “Janna'' time. It was around this time that I really started experimenting with my sexuality in relation to crossdressing. For those that followed me throughout my Tumblr years, that should be pretty self-evident by the content and frequency that I was posting. All this deviance peaked around the Summer of 2014 while I was in New Mexico for an internship. I was regularly positing to Tumblr, Reddit, 4Chan, maintained an active FetLife account and even started streaming a bit. On the more vanilla side, I also fell extremely hard for a friend that I started getting closer to at the end of the internship. The juxtaposition of the feelings I felt about her compared with the unhealthy level short-term attention I was trying to chase for my girl persona left me feeling really empty especially after the internship ended and I had to go back to Texas. It’s a bit unusual the level of impact those three and a half months in New Mexico had on me, but I guess that’s why the state’s nickname is the Land of Enchantment.

      Upon starting my fourth year at college, I decided to at least attempt to find a more normal relationship and basically fell straight into the first girl that showed interest in me. Bella and I were frankly an extremely poor fit and the only thing we seemed to share in common was that we were both extremely introverted. Also, maybe we both liked sports as we met from the flag football team I was captaining. There were also a ton of flags, but I pressed on anyway. In all honesty, this was most likely a rebound from what happened during the Summer, but I think I convinced myself that this was what I wanted. About two months after we started officially ‘‘dating”, I decided to tell her about my crossdressing habits. She had moved in with me at this point and with the size of my girl closet, it was getting really hard to convincingly say that all of the girls clothes, all of this lingerie, the toys were in fact not for me, but actually just leftovers from previous girls. Especially since the clothes seemed to multiple over the months.

      Working the topic into a conversation naturally is difficult. If you wait for the perfect moment to come, there’s a good chance that it might just never happen and before you know it, you’re in a stable, committed relationship hiding a potentially relationship breaking secret. Either that or you’re caught in the act and you’re unexpectedly forced to come out. With Bella, I decided just to sit her down one night after watching a movie in bed and told her I had something important to tell her. I don’t remember exactly what my plan was, but I wanted to put my best foot forward and decided to show her (what I thought was) my most convincing picture. The picture in question was me dressed up in a nurse outfit, the same outfit in fact as the one I wore out in public the first time. At which point, hoped either she would be super into it (every crossdresser’s dream right) or at least understanding about it and ask questions. Weirdly, I wasn’t that nervous as one, I admittedly didn’t think the relationship was going anywhere but two, I actually naively expected it to go smoothly. Up to this point, I had confided in a few close friends about crossdressing, showed them pictures and everything had gone well.

      Showing Bella the picture was about as far as the plan got. I told her, this was me sometimes and she … freaked … out. The ordeal started in my bedroom and after a few moments she ran out into the living room. I followed her out trying to console her, although of what, I wasn’t sure. After a while of that, she ran back into the bedroom and I decided to wait, partially to give her a few moments by herself and partially to collect my thoughts. Or more accurately, my thought as the only thing I was thinking was what the hell just happened. Eventually I gathered the courage to walk back into the bedroom and to my surprise she wasn’t there. I looked around the room, in the bathroom, and eventually found her balled up crying in my closet. I managed to get her back sitting in bed, and we started working through what happened. Bella eventually explained that she was shocked because she looked up to me and was expecting a masculine figure as her boyfriend. The idea of me dressed as a girl just didn’t fit into that pedestal image in her mind. I don’t remember what happened after, but it’s hard to imagine how the conversation could have gone worse. Eventually, I believe we must’ve made up because we stayed together for a few more months, but that relationship effectively died that night².

      Reflecting on my experiences with Amy and Bella, as hurtful as they were, it did teach me a few valuable lessons.

1. Don’t put your significant other on a pedestal. With Amy I was the one looking up, with Bella it was the other way around. Either way, it’s not healthy and it trashes self-confidence.
2. It affirmed my belief that telling my significant other about crossdressing was important. Hiding it with Amy was unhealthy and while it turned out badly with Bella, at least I found out early on that it was a deal-breaker.
3. The difficulty of talking about secrets like crossdressing is inversely proportionate to how invested you are in the relationship.

      I met Casey a couple of months after things ended with Bella and hit it off quickly. In contrast with all my other relationships, Casey was a lot less vanilla and so my collection of Janna related items quickly came into relevancy. I’ve always wonder how much she knew before I told her because it can’t be normal for a guy to own a closet full of sexy Halloween costumes and lingerie and have a drawer full of toys, but for the longest time she never questioned it. Soon, Casey was spending so much time over, that she had basically moved in, but we weren’t officially in a relationship because we were both going on dates with other people. I don’t remember how it came up, but eventually she did ask me why I had all the stuff and I came clean about it. She asked a few questions including the typical “Are you gay” one and once I assured her I wasn’t, that was pretty much it. She was understanding about it. No drama. At least not about my crossdressing. Irrelevant to the topic at hand, that relationship (and friendship) nosedived pretty quickly when I first grew jealous of the other guy she was dating and then finally torpedoed into the ground when I eventually chose the other girl I wa dating, Dianna, over her.

      For those that enjoy a little bit more drama, Dianna was one of Amy’s best friends before they had a falling out a few years after Amy and I split. This had nothing to do with why I was dating her, but there is some sort of irony buried in there. To keep this post relevant, I’ll fast forward nearly a year to the final semester of college. Dianna and I have been in an exclusive relationship for nearly half a year at this point and we were facing the question of what we were going to do post-college. I had accepted a job offer in San Francisco and she was most likely going to stay in Texas so if we stayed together, it was going to be long-distance. She was learning towards just ending it as she had poor experiences with long-distance relationships in the past. This freaked me out because I wanted more. The fact that I also hadn’t told her about “Janna’' was also weighing on my mind. I was scared to tell her both because of how much I liked her and because she was more on the vanilla side. If the conversation went as badly as it did with Bella, I knew I would have been absolutely devastated. However, I decided that if I was going to ask her to commit to a long-distance relationship, it would only be fair if she knew about everything and I chose to do it during our Spring Break road trip through New Mexico. To make sure I didn’t forget anything and as an encouragement in case I chickened out, I wrote everything down in a journal and stashed it in my luggage as we drove through the Land of Enchantment.

      I finally built up the courage to lay (almost) everything on the table on the return journey. In a dated motel room somewhere in Taos, I told her how I felt. I told her how much I wanted to stay together and about my crossdressing interests. I told her about Janna and to her benefit she maintained her composure as I broke down and sobbed through everything I wanted to say. I very rarely cry, but when I do, it gets ugly. She of course asked questions, “Why do you do i”, “How often do you dress up”, “Are you straight” but was very understanding about it all. I may have sugar-coated some of the answers I gave, because to this day she still claims I told her I only dress up “once or twice a month”. I think that might have been true when I gave the answer, but it’s certainly not true today as I probably spend more time in girl clothes than boy clothes now. Either way, the fact that she didn’t freak out was already a big win and even though it didn’t seem like she was enthused about my crossdressing interests, it also wasn’t something she was entirely closed off to.

      Four years later, Dianna and I are still together. I did have to ease her into some things like the existence of my Tumblr and Reddit accounts and the fact that I wasn’t completely straight, but I think that initial conversation was always the most difficult and certainly the scariest. Things haven’t always been smooth sailing and I want to make sure I don’t give off the impression that our relationship is absolutely perfect after I told her about liking to crossdress. The subject has been the topic of minor contentions over the years. She complains sometimes that I spend too much time in girl mode, and I’ve noted to her that I wished she was more open to exploring kinks (similarly she wishes I was more open to exploring new foods, but just like how she’s pretty vanilla when it comes to kinks, I like eating what I know I’ll like). I’ve also had issues adequately voicing my sexual interests especially regarding topics that conflict with the traditional image of a masculine straight guy. At the end of the day, it really is all about compromises and we’ve both had to give up on parts of our ideal image of a perfect relationship. That’s not to say I don’t often daydream about how awesome it would be if my significant other was super into makeup and already into very feminine guys. We could go shopping together, share clothes, slut it up at clubs and then just as quickly go back to a normal relationship. I mean, what crossdresser hasn’t wished for a cosplay girlfriend that will dress them up in cute clothes and do their makeup. Fortunately, some people get to live those dreams (looking at you Sneaky), but for the rest of us, sometimes you can’t have everything and that’s okay. The most important thing is just that your significant other understands what is important to you. They don’t even have to understand why (I’m fairly certain Dianna still doesn’t fully understand why I like crossdressing), just willing to accept you for who you are. Over the years, Dianna has come around bit by bit to my crossdressing hobby and has gone from merely tolerating it to sometimes indulging me. Originally it started small like being okay with me wearing girl clothes in bed or being fine with the content I was posting. Later when I moved to San Francisco, she went with me to my first (and second) Folsom Street Fair. Went with me to my first Anime Expo, although quite reluctantly and only when I agreed to also go to Universal Studios. She was also very encouraging and supportive when I finally decided to come out (about crossdressing) to my friends. And as for living the dream, every now and then she helps me do my makeup, goes clothes shopping with me and on rare occasions, buys me lingerie as random gifts. So I guess the dream is still alive and kicking.

As always, here’s a TL;DR:

1. Seriously considering telling your significant other about your kinks early on in your relationship. Especially if it is one that you actively indulge in. Hiding secrets is just unhealthy in the long run and the ramifications of it being a deal-breaker once the relationship is serious could be catastrophic.

   

2. Even if it’s no longer early in the relationship, I would still consider telling them. I didn’t tell my current girlfriend about my want to hook up with guys until a while into our relationship.
3. DO NOT cheat on your significant other. In the “sissy'' kink, cheating on your SO almost seems normalized. Not sure how much of this is fantasy vs actual action, but don’t do it. If you want an open or semi-open relationship, tell them and tell them why.
4. If you have a hard time articulating your thoughts in person, write them down in a journal or letter. Worst case, you can just hand them the letter.
5. Relationships are about compromise and you’re unlikely to get your ideal image of a relationship. Try to understand what’s important to them and hopefully they’ll likewise do the same for you.
6. In regard to telling your significant other about crossdressing, sometimes it will go sideways. Lets face it, it’s a bit weird and some people won’t be able to accept it. You may just have to take solace in the fact that they weren’t the person for you.

Footnotes