‘My girlfriend gave me an ultimatum. ‘Either that has to go, or I do.’ I broke down in tears. I tried my hardest to stop, but the desire lingered on in secret.’: Male crossdresser outed at work details journey to ‘liberation’

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“Being normal is overrated. I spent the first 30 years of my life trying to be normal and it was just so…boring.

For all the ‘normal’ things about me, this was the one ‘weird’ thing about me. When I say ‘weird,’ I mean it was the kind of thing that turns people away from you. I’m weird because I’m partially colorblind, I don’t think cilantro tastes like soap, and I mimic other people’s voices (even accents) back to them without thinking. None of these are deal breakers, however. Yet, crossdressing is.  Or, at least, I thought it was.

I grew up in a conservative context – the American South during the 90s and early 2000s. I was part of a Southern Baptist Church, went to a Christian school, and, truthfully, I was about as culturally masculine as one could be. My dad taught me to shoot, shave, tie a tie, grill like a pro, and stand up for myself. My mom taught me how to treat women right, the importance of a clean living space, to always be truthful, to protect my little sister, and that details always matter. I played sports, ate plenty of red meat, liked cars, spent way too much time playing video games, and idolized action movie heroes. Cultural masculinity was not all great, though. I also learned to bury my feelings, not show weakness, pull myself up by my bootstraps, and to never cry. Any form of weakness was ‘feminine’ and strength was ‘masculine.’ These were the days when men were men and women were women; those lines were never to be crossed.

I grew up having a fascination with women’s clothing. I would borrow my sister’s or mom’s clothing when they were out, try them on, and put them back before they ever returned. There was a certain thrill to it: one I could neither understand, nor articulate. I would do this once every few months and that was enough for me. But it was still a secret – and it had to stay one.

A lot of fear comes with having a secret like that. What if my family finds out? What will they say? What will they assume? What will happen to me? The risk was too high. I had to be careful. As I got later into my teenage years, the desire was still there. It was clearly not some passing fad or ‘phase.’ I would find myself looking online at pictures of crossdressers and wishing I had the freedom to be them. I thought it would be so cool to get a makeover and have a girls’ day, but I never dared to admit it. Plenty of relationships reinforced that for me.

At the age of 23, I started dating a girl who I developed a serious relationship with. Around the time we were starting to discuss marriage, I felt like she needed to know. Sitting on her couch late one night, I broke down in tears and told her about my crossdressing. I told her I still didn’t understand it, but the desire was there. Quite frankly, she hated it. She gave me an ultimatum and essentially said, ‘Either that has to go, or I do.’ I, being young and in love, thought the choice was clear. I tried my hardest to stop, but the desire lingered on in secret. I knew it would become an issue in marriage. We did indeed get engaged, but, for reasons unrelated to my crossdressing, the engagement was broken off. I still felt it was part of the reason, however, so I sought to kill the desire. It disappeared for a while, but it never died. 

Courtesy of Samantha Lawrence

In my late 20s, I enrolled at a renowned Christian seminary to pursue my Master’s. Ironically, it was during this time I experienced the most growth and freedom in becoming Sami, my crossdressing persona. The first hurdle was squaring my crossdressing with my faith. I had to know if the Bible had anything to say about it. The only thing I could find was in Deuteronomy 22:5: ‘A woman must not wear men’s clothing, nor a man wear women’s clothing, for the Lord your God detests anyone who does this’ (NIV). Using the skills and tools I had been learning, I quickly found out this verse was not talking about me being more comfortable at home in a skirt, rather than athletic shorts. It is a warning to the nation of Israel against cultic practices in the Canaanite religion, prostitution, intended harm, and homosexuality.

I started looking beyond that. Could there be something sinful in my heart that was pointing me in this direction? The more questions I asked, the more they came back as ‘no.’ Could it be I was struggling with my gender identity or sexuality? Again, the answer was no. I am very happy and comfortable as a straight man. What I was left with was this: I wanted to express my feminine side in an unconventional manner and I had no convictions telling me I was in sin for doing so. But I wasn’t ready to pull the trigger yet. I created a throwaway account on Reddit, told my story, and pleaded for help. One person, who so happened to be a person I looked up to for their ridiculous confidence in crossdressing, reached out to me. She goes by the name of Scarlett (spoiler, she became one of my best friends). I remember the conversation vividly. Scarlett said to me, ‘Yeah, you could continue to suppress this and be content…or you could see what it’s all about, be happy, and potentially thrive.’ So, I finally gave in.

Courtesy of Samantha Lawrence

I nervously would go to department stores and would try on dresses. I would bury them under piles of jeans and large sweaters which I would take into the dressing rooms. It was exhilarating and terrifying at the same time. After all, what if somebody saw me and called me out on it? The shame cycle returned. I didn’t dare buy anything from the stores, I simply tried them on so I could find out my size. I turned to Amazon Prime Wardrobe so I could try on tons of styles and keep what I liked. I finally had clothing of my own. From there, I started buying shoes, then wigs, then makeup. It was so surreal that it was becoming a reality for me.  To put it bluntly, I’m a hairy individual. I had a full beard at the time. Not only did I want to shave my beard, but I also wanted to shave my legs, my arms, and my chest so I would be getting a more full experience. How would I explain that to people? Men being men, it was easy just to say, ‘I lost a bet’ and move on.

The first time I put the whole look together with outfits, shoes, makeup, shaved legs, etc. and saw myself in the mirror was indescribable. I got goosebumps all over and didn’t recognize the person I was looking at (mostly because the makeup was atrocious). The next 6 months or so were filled with firsts for me. I made real friends where I live (who have also become some of my best friends). I came out to a trusted female friend from back home who was more than excited for me. I got a professional makeover and went out in public for the first time, both in the same day. I met up with Scarlett and a few other crossdressers and we had a fun girls’ weekend together. Shortly after, I came out to my best friend and his wife, who were above and beyond accepting and loving. 

Courtesy of Samantha Lawrence
Courtesy of Samantha Lawrence

While all of this was happening, I also started my Instagram account. Originally, it was meant as an outlet for me. For the first time in my life, I felt beautiful and I was getting to live my dream, but I couldn’t show anybody that knew me. I wanted to share my story and my progress with the world and Instagram seemed to be the best way to do it. I wanted to find community. I was a little scared to do it, though. The questions returned. What if someone finds out? Even if I’m careful and never tell anyone who I am/where I live, what if somebody figures it out? I told myself that, to be able to find a crossdresser on Instagram, you’d have to be really looking for one, especially someone like me with basically no following. I pushed forward. 

Since starting my account, I have found community with people like me from all over the world. But something bugged me about the community: it was a glorified beauty pageant. We were silently competing with each other for followers, even if we didn’t realize it. We cloaked ourselves in falsehoods of photography tricks, photoshop, and filters, all in service of appearing ‘more feminine.’ We were more concerned about how we looked (or rather, how others thought we looked) than who we were. Having a year of Instagram under my belt, I think I better understand why now: fear.

We operate in the shadows out of fear. We objectify ourselves and allow others to objectify and fetishize us while we do nothing to change it. We don’t live our lives as we want. We rarely experience the freedom of being in public or around our loved ones, living a normal life. Certainly there are some societal strides of acceptance and normalization that need to be made, but the fact that I (and others like me) am called ‘brave’ for going out in public as Sami tells me something is askew. It doesn’t need to be a bold, courageous step for me to go out for drinks with my friends in a dress instead of jeans and a t-shirt. It’s just clothing. It should be a ‘live and let live’ mentality. Part of what I continue to try and do in the crossdressing community is to educate and help bring understanding. It is wise for us to know why people react the way they do, but it’s important for us to have a healthy kind of pride in ourselves – the kind of pride that is grounded in a fundamental understanding of who we are as human beings, not the kind of arrogant pride that demands respect and acceptance. I did a Pride Month miniseries of videos on my Instagram this year for this very reason.

Courtesy of Samantha Lawrence
Courtesy of Samantha Lawrence

About a month ago, I got hit with some very bad news. I had come out to a handful of people whom I trust and I was thrilled to no longer be hiding this part of myself with them. I got a text one morning from my best friend. It simply said, ‘Hey.’ Given that he never starts a conversation so simply, I knew something was up. He went on to tell me somebody at work had discovered Sami and was spreading it around. I work with about 300-400 people, most of them positionally lower than me, so this was a big deal. If somebody wanted to ruin me for whatever reason, they had gotten the best head start they would ever need. My heart sank down into my stomach.

My best friend said, ‘It may be time for you to have some conversations on your own terms. Maybe with your family.’ He was right. All that was going through my mind was that somebody was going to put me on blast on my Facebook and share the news with the world. Granted, I was making plans to come out to everyone by the end of the year, but you never want that control ripped away from you. I immediately got busy and didn’t let myself feel anything. I knew what had to be done: I had to get in front of it. Over the next 48 hours, I came out to basically everyone I cared about (except my parents, they deserve for that news to be delivered in person and they live on the other side of the country). It was mentally and emotionally draining. My worst fear had been realized and I was preparing myself for the fallout. It was a dark two days. 

Let me say up front that nobody deserves that treatment. When people have news to share, it should be up to them to share it. Please, if I can make one request of you today, don’t ever out anyone before they’re ready. It’s not fair to them. The mental and emotional distress I experienced is not something I would wish on anyone. I am one of the very lucky few who got an overwhelmingly positive response. The worst I got was indifference. My sister and I bonded in a brand new way; she’s going to meet Sami for the first time in person soon enough. My female friends were excited because they had something new to include me in. My male friends and my brothers were supportive, even if they didn’t understand. My colleagues at work were so happy for me. My boss was ecstatic and invited me to come to work as Sami whenever I wish. My core group of friends invited me to be Sami next time we’re all together. One of my best friends threw me a ‘coming out’ party this past weekend and I wept so many times over how happy and liberated I felt. I got hugs and encouraging words from so many people. My friend and I have launched a joint effort side project of building a professional photography portfolio for her and modeling portfolio for me. I’m currently developing a roadmap on what direction I want to take with the YouTube channel I just started. 

Courtesy of Samantha Lawrence

I’m no longer hiding. That was the real dream. Soon enough, I will make Sami publicly known on all of my social media platforms. If you ever come across me online or in person, feel free to drop by and say hello.

As I look back on all of this, it’s easy for me to wish I had accepted Sami when I was a teenager, but I think the course of my life would look very different right now if I had. As it stands right now, I’ve met an incredible group of people who love me no matter what I’m wearing that day. I have found a way to integrate Sami into all facets of my faith and walk with the Lord. I am continuing to try and foster community, inspire personal growth, and, overall, be a role model for people to look to as someone that they can trust, confide in, and see that someone has walked the path before them. I have found new purpose in life. I am in the process of applying to PhD programs because I want to continue researching theological considerations of transgenderism and mend the wounds that have come between the transgender community and the church. I have found that I don’t need to be afraid of Sami. On the contrary, she will help me change the world.”

Courtesy of Samantha Lawrence
Courtesy of Samantha Lawrence

This story was submitted to Love What Matters by Samantha Lawrence of Texas, USA. You can follow Samantha’s  journey on Instagram and YouTube. Submit your own story here and be sure to subscribe to our free email newsletter for our best stories, and YouTube for our best videos.

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