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.
Thanx for your article Cindy! Very refreshing to rad this especially that I can relate to many thing you spoke about! Hugs!
You are so pretty
Beautiful reflection, Cindy. I and many other “confused men" share your story and your duality. –Lara
Thank you, Cindy. I appreciate your perspective. I am brand new at accepting my crossdressing and am conflicted at so many levels and in so many different areas. I too like to get dirty doing hard work. So, it’s really good to hear your perspective as a man and as a woman. You are beautiful, inside and out. Thanks again.
Renee
Thanks Renee. Crossdressing is something I have learned to accept as who I am. As I get older, I learn to be me and not really care what others think. I have a wife and kids so I take those into deep consideration before I act on something. I don’t want to embarrass them but as for any one else. I am who I am. And I’ll live my life in a way that makes me happy.
Love your story!!
Thanks Isabella
OMG, this story is my life. thanks for sharing.
You’re welcome Danielle. I think it is very similar to most men in the mid life who enjoy crossdressing
Love having a beard dressef
Love having beard dressed but shave it for my monthly Samantha weekend
There are times when I want to be passable and others where I like my beard and my makeup together. I think it’s a thing. Being a man with a feminine side isn’t so new and some people like it.
Hi Cindy,
The best sentence in your story that I enjoyed reading is:
“Just because I like dressing as a woman does not mean I like men."
That’s the bit that people don’t get. But when they do they will realise that it just as natural a desire for us as it is for women.
Thanks
Ger
That seems to be the hard part for most people to get past. I agree. I think it takes time before people learn that this is a thing and doesn’t mean a crossdressing man has to like men.
Thank you for your article. Your bio is very similar to mine and i’m sure many others. Never would I have imagined telling ANYONE up until I told my wife a few years ago. The guilt was too much. I agree society’s general tolerance and the wealth of information available for gender topics has made it “easier" to come-out. There are times I wish I was a teen in today’s environment. I would still be very resistant to tell anyone but at least I would know that I am neither alone nor feel that I am less of a person.… Read more »
Have you asked your wife if you can appear fully dressed en femme in front of her? Maybe she will say yes; the worst is no. as she already knows you CD. Maybe she wants you to take that step. Best wishes.
I’ve never outright asked her but she’s alluded to not being comfortable with it. She’s even made note of a few men on separate occasions she’s seen dressed in public and trying to pass. Her comments and general tone were not derogatory/dismissive but they were not supportive. Once, I wore something simple and sexy to bed and she simply turned to me and said “no”. I turned tail and changed. I guess I’ve been afraid to push it again. I’m still trying to assess my boundaries without alienating her to a point where she’s not accepting of it even in… Read more »
I’ve done the same thing Jamie and my wife just isn’t there yet. It takes time and a little home that she finds a friend to talk to that might come clean on enjoying some of this and make her feel a little better about playing around with it.
It takes time. Little by little doing things like that add up. Watching movies where it happens, see it out in public and pointing it out, trying to make appropriate comments that you think might go over well like, we should try that just to see, or disguising it as a role reversal evening after some drinking to lighten the Witt’s.
I used to do this and since coming out to her I’m cautious about commenting on women’s fashion in movies or in person. I sense that whenever i make a comment she thinks “he’s only saying that because he wants to wear it". Coincidentally 4+ years ago our neighbor (40 year old+/- husband) across the street started to grow his hair long and had “men’s earrings like some guys do. My wife would comment off handedly about how awful it looked. Shortly after we noticed he was occasionally wearing a skirt but otherwise men’s clothes and shoes. Fast forward to… Read more »
I have actually. Not fully decked out but she and I love to play video games. Not first person shooters but Mario brothers, Mario cart and games like guitar hero and dance dance revolution. It was during DDR that I semi dressed. I think she wanted to see how it felt. It was getting hot from dancing but we weren’t done so we went upstairs to change. I was looking for cooler shorts and she gave me her tube top. Doubles as a mini skirt. So I wore it the rest of the night. Was so liberating to do it… Read more »