As a man who enjoys crossdressing on a regular basis, I can easily say I made the same mistake that most other men do. Not telling our SOs. We grow up knowing that we like women’s clothing. Everyone likes different aspects of it and everyone has different reasons as to why. But we also grew up in an era where this was highly unacceptable and kids got picked on for it, even if looking feminine was unintentional, such as wearing tight pants because we could not afford new ones or a “girly” color as part of our outfit. The crossdressers of my age saw that, or were a victim of it, and made sure they kept that aspect of their life hidden. Even with people I love very much, I could not be open. I didn’t tell my mom, my friends; I did not tell my SO, who I ended up marrying and with whom I shared many other secrets. By that time, I was “built” to keep my crossdressing hidden. Many times I’d try to put it away and think “it’s just a phase.” But the reality is it’s not a phase; it’s a permanent part of my life. It’s something I enjoy doing. I can’t pinpoint why I like it, but the point is, it’s there.
But this is why I hid it. It’s not that I didn’t trust my SO, even though that is what it seems like. Society brought us up that way in the 20th century. Nowadays, in my kids’ era, crossdressing is pretty acceptable among the right group of people. Finding resources is easier due to the internet, and people are not as closeted as they once were. More people find it acceptable as society, today in the 21st century, mostly allows people to be who they want to be. I see guys wearing sports bras at the amusement park, and guys with beards wearing makeup as a style, which I myself have tried and like. Tight clothing has become a thing of the past as being a women’s style only. I was recently able to buy a pair of stretchy tight pants at the store, in the men’s section. Sometimes I wish I had been born about 20 years later because these things are more acceptable now. It would have been a lot easier to communicate it to my SO, but then if I was born 20 years later I would not have met the woman I am so dearly in love with and will hopefully live the rest of my life. She makes me happy and I cannot see a future without her.
Eventually, my SO became aware of my crossdressing and out of respect for her, I now have my own clothing and my own makeup. I do not dress in front of her, as she is not yet ready to see me. A couple years into it, and she is still processing. I felt it was very important to let her know that betrayal of trust is the last thing I wanted. I have no intention of leaving. Just because I like dressing as a woman does not mean I like men. I am very much attracted to women. I enjoy being a guy, and taking on the role of the protector and the strong father, even though I might be wearing a pair of panties underneath it all or dressed in full role reversal in the bedroom.
And on a late night walk, I pity the fool who thinks he is going to harass a couple ladies walking together.
Hi Cindy, I just joined the site today. It seems many of us have similar stories. My wife, of 49 years, has never known my secret. No one has. I have bought clothes while traveling for work, and thrown them away before leaving for home. And, never worn them outside if the hotel room. Well…. Ok. I have worn panties, under my suit. But, not for long, it’s always that hospital emergency room issue in my mind….. I have never felt gay, and always been attracted to women. Infact, my secret desire is to have a sexual encounter with a… Read more »
Oh yeah…. Erika? I too had a long law enforcement career……
Those who are troubled about whether to be honest with a companion might find it useful to see the Tim Burton Movie ED WOOD, based on the true story of an an enthusiastic crossdresser in the 1950s who is remembered today as perhaps the most amateurish in Hollywood history. Wood’s best known picture is GLEN OR GLENDA, in which he plays both parts. (Both movies are available online.) ED WOOD is a very funny comedy, with Johnny Depp in the title role and a great cast including Bill Murray and Martin Landau (who won an Oscar for it). There is… Read more »
I dropped a word in the post above. Make that “the most amateurish director in Hollywood history."
Great article Cindy !!!
It’s so reassuring to hear my story as shared by another person. Thank you so much for sharing your emotions.
These are all great views and well expressed. I still think that I have found a happy medium in my “management" of my gender fluidity. Fear the “Pink Fog". It takes discipline, and more and more these days given the dangerous fire storm that social media can create. Evidence…it’s not about cross dressing but this week in Ottawa we have a case of a longtime member and former minister of both provincial and federal losing it all on social media. His Willy spoke to him louder than his noggin and he las been dismissed and his family shamed. Something to… Read more »
Hi Cindy, I’m in the closet CD and am petrified of coming out. After reading your post I’m thinking and I mean JUST THINKING bout coming out. I worry so much about what others will think or do. If I had a CD girlfriend to encourage and show me the way I think I could do it. Thats why I came to this site, to hopefully find a friend to help. All the other sites seem to be just for sex,sex,sex.and as we all know there’s more to this lifestyle than sex. I’m in Richmond,VA area so would greatly appreciate… Read more »
I’m reading though a lot of articles because I’m finding myself in the same boat as you. I am proud and happy to be a man, but also very into women’s things ever since I was a kid. I can’t help it, it feels so good but the feelings are scary and conflicting. I have partially told my fiance, she knows that I wear panties, but not about the dresses. I want to share it with her, to have her at least know that I do and that I like to and that it doesn’t make me any less of… Read more »
Thank you for sharing Cindy. Not sure the terminology is right, but I like to tell myself I was “smart enough" to tell my gf very early on(it was scary) she was, and is awesome with it. I hope your SO’s processing is still moving in the direction of acceptance towards you. In the meantime enjoy it within your boundaries and the role reversal part. I know I do
I don’t know what to think, but gratefully, I don’t have to. I may think that my brand of crossdressing is less ridiculous than Cindy’s, but that’s OK. Most of the things we choose to do in life have a sense of the ridiculous in their variations. The point is that we should have the choice to pursue endeavors that fulfill our needs while not harming others or impeding their abilities to pursue their needs. Morality is not about some abstract list of rights and wrongs. It is about charity, kindness, and genuine empathy.
Bless you,
FAM
The ongoing normalization of crossdressing seems to be taking some of the thrill, alla playing hooky, out…Mais oui?