My Boyfriend Loves Cross-Dressing & I Support Him

My boyfriend loves wearing skirts from time to time and even has an amazingly well-kept wig collection to accompany them. While it was mad to see him dressed as a woman at first, I got used to it pretty quickly. Cross-dressing makes him feel confident, so who am I to argue?

  1. He’s not gay, trans, or confused about his sexuality. The day I found out my boyfriend cross-dresses, I immediately sat down for a conversation with him to find out what was behind it. Was he confused about his sexuality or gender identity? Was I his beard to mask his true self? My head swirled with so many questions until he finally put them to rest. He held my hand and told me he was 100% straight and that his love of cross-dressing doesn’t change that. He’s just not phased by gender norms, and that’s a good thing.
  2. He doesn’t fit society’s ideal of masculinity and that’s OK. Men are often seen as weak if they aren’t traditionally “manly.” You have to be aggressive, physically imposing, love sports, and physically imposing. My boyfriend doesn’t fit any of those descriptions. He’s soft-spoken, hates picking fights, and doesn’t mind me taking charge—and he knows those things don’t make him any less of a man. He’s more confident living up to his own ideas of masculinity than become a walking stereotype.
  3. He doesn’t mind being called a girl. A lot of guys act like being a woman or even being seen as marginally feminine is a fate worse than death, but my boyfriend likes it when people say he acts like a girl. He grew up with two sisters and a strong-willed mother so he knows being called a girl isn’t an insult. In fact, whenever we would go out and he’s all dolled up, he enjoys it when he passes as female. He has fun being a girl, so why would he take offense being called one?
  4. He’s not afraid of his emotions. A lot of men are afraid to cry. They’re afraid to be labeled as weak for shedding a few tears, but my boyfriend finds crying freeing. He prefers to open up rather than bottling his emotions. He understands showing emotions is healthy, and we spend a lot of our days sitting down and talking about our feelings.
  5. He feels comfortable in women’s clothes and loves playing with fashion. My boyfriend dresses the way he likes and doesn’t care about other people’s opinions about it. When it comes to cross-dressing, he puts a lot of effort into not only looking good but feeling comfortable. He doesn’t only try to look like a fabulous woman, he wants to walk around knowing there won’t be blisters on his feet and he won’t be struggling to breathe in ridiculously tight clothes. It’s the same when he doesn’t cross-dress. He’s been able to create his own personal style and become confident in everything he wears as a man and a woman.
  6. Being someone else is refreshing. Sometimes we don’t like the skin we wear or we just want to try something else for a change, be someone else for a day just to see what it’s like on the other side. My boyfriend experiences that every day. He not only cross-dresses, he becomes someone else entirely. Dressing like a woman is like taking a break from his life. He’s a different person and it’s like hitting refresh once in a while.
  7. He loves himself, and why shouldn’t he? He’s not a narcissist, but he does embrace and appreciate everything that makes him who he is, and I envy him for it. He can look in the mirror without an ounce of self-hatred. In fact, he has self-esteem in spades. His insecurities never get the best of him. You can see his confidence whenever he walks down the street flaunting his look, and it’s amazing to see.
  8. Cross-dressing makes him feel beautiful. My boyfriend admits he loves putting on makeup because it makes him look pretty. He enjoys the work that makes him look beautiful—it’s the effort that makes it all worth it. He literally blushes whenever someone compliments his eyebrows or the winged eyeliner he worked so hard on.
  9. He doesn’t let other people get to him. I notice there are people who find my boyfriend’s cross-dressing unusual. They call him a “fag” or “tranny” behind his back or sometimes to his face. Whenever that happens, I’m always prepared to verbally detonate anyone who dares to speak to or about him this way, but he stays calm. He says that if he lets other people’s comments bother him, it would only make him miserable. He’s proud of who he is and trolls can’t change it. I have to say, I’m pretty proud of him too.
A freelance writer who mostly writes about Netflix shows, love, relationships, and ghostwrites for other sites. She's also a huge geek who would suddenly burst into a full on rant on why Bruce Banner should be your favorite character and why "Justice League" should be more appreciated.