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.

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I have enjoyed cross dressing since I was about 7 years old. I like a little of both worlds. I enjoy makeup, both with and without a beard, I enjoy wearing a thong every day. I keep my body hair short or shaved and my nails longer. I have feminine characteristics like wearing makeup weather I am cross dressing or not. I like red lipstick but most of the time I wear a nude color lipstick throughout the day. I wear concealer on occasion and a little eyeliner. I like traditionally women's type clothing like wearing a T back tank top and yoga style pants. I like the feel of a bra and I enjoy spaghetti strap tops. Even thought I like these feminine items, I like being a man as well. I like having muscles and being strong. I like to get dirty under the hood of a car and go camping. And sometimes, I like mixing both such as I mentioned above. Having a beard with red lipstick on is sexy. Most of the winter, I have a full beard and I still wear concealer.

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Cassandra Rossdale
1 year ago

Thanx for your article Cindy! Very refreshing to rad this especially that I can relate to many thing you spoke about! Hugs!

bill stckman
Lady
bill stckman (@baseball184)
1 year ago

You are so pretty

https://images.crossdresserheaven.com/7mjKzxo-RsH54RL7/w:auto/h:auto/q:75/https://www.crossdresserheaven.com/wp-content/uploads/2019/11/woman-gray-1.jpg
Member
Lara Cross
1 year ago

Beautiful reflection, Cindy. I and many other “confused men” share your story and your duality. –Lara

Renee Rose
Lady
Member
Renee Rose (@reneeh)
11 months ago

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

Isabella Hart
Isabella Hart (@isabella1934)
10 months ago

Love your story!!

Danielle Wayne
Duchess
Active Member
Danielle Wayne (@daniellegrl)
9 months ago

OMG, this story is my life. thanks for sharing.

Samantha Red
Lady
Samantha Red (@bgserge)
6 months ago

Love having a beard dressef

Samantha Red
Lady
Samantha Red (@bgserge)
6 months ago

Love having beard dressed but shave it for my monthly Samantha weekend

Ger Hayden
Lady
Member
Ger Hayden (@gerhayden)
3 months ago

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

Jamie Taal
Duchess
Active Member
Jamie Taal (@jamietaal)
2 months ago

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 »

Marlene Roberts
Lady
Member
Marlene Roberts (@marleneroberts)
2 months ago
Reply to  Jamie Taal

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.

Jamie Taal
Duchess
Active Member
Jamie Taal (@jamietaal)
2 months ago

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 »

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